# 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_Hphpya _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 N3 P' _chemical_formula_weight 355.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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' 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 11.7579(2) _cell_length_b 7.7009(1) _cell_length_c 20.4790(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.190(2) _cell_angle_gamma 90.00 _cell_volume 1825.05(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7692 _cell_measurement_theta_min 3.8240 _cell_measurement_theta_max 62.7210 _exptl_crystal_description 'transparent prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 1.400 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7660 _exptl_absorpt_correction_T_max 0.9666 _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1399 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10978 _diffrn_reflns_av_R_equivalents 0.0590 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.05 _diffrn_reflns_theta_max 62.77 _reflns_number_total 2920 _reflns_number_gt 2759 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlisPro, Agilent Technologies' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies' _computing_data_reduction 'CrysAlisPro, Agilent Technologies' _computing_structure_solution 'SIR92 (Giacovazzo et al., 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'WinGX (Farrugia, 2012)' _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^)+(0.0625P)^2^+0.2634P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0028(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2920 _refine_ls_number_parameters 239 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0384 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.1038 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 -0.00294(15) 0.2721(2) 0.51623(9) 0.0357(4) Uani 1 1 d . . . H1 H 0.0594 0.2823 0.5525 0.043 Uiso 1 1 calc R . . C2 C -0.11183(15) 0.3315(3) 0.52251(10) 0.0449(4) Uani 1 1 d . . . H2 H -0.1236 0.3822 0.5631 0.054 Uiso 1 1 calc R . . C3 C -0.20316(14) 0.3177(2) 0.47022(10) 0.0440(5) Uani 1 1 d . . . H3 H -0.2776 0.3585 0.4747 0.053 Uiso 1 1 calc R . . C4 C -0.18565(15) 0.2439(2) 0.41122(10) 0.0422(4) Uani 1 1 d . . . H4 H -0.2482 0.2343 0.3750 0.051 Uiso 1 1 calc R . . C5 C -0.07708(14) 0.1840(2) 0.40484(9) 0.0362(4) Uani 1 1 d . . . H5 H -0.0659 0.1330 0.3642 0.043 Uiso 1 1 calc R . . C6 C 0.01568(13) 0.19744(18) 0.45708(7) 0.0265(3) Uani 1 1 d . . . C7 C 0.13269(12) 0.13237(17) 0.45197(7) 0.0235(3) Uani 1 1 d . . . C8 C 0.15870(13) 0.0515(2) 0.39525(7) 0.0300(4) Uani 1 1 d . . . H8 H 0.1018 0.0377 0.3564 0.036 Uiso 1 1 calc R . . C9 C 0.26944(13) -0.0070(2) 0.39789(7) 0.0294(4) Uani 1 1 d . . . H9 H 0.2874 -0.0656 0.3602 0.035 Uiso 1 1 calc R . . C10 C 0.32089(12) 0.09609(18) 0.50229(7) 0.0226(3) Uani 1 1 d . . . C11 C 0.52784(13) 0.32933(19) 0.64613(7) 0.0253(3) Uani 1 1 d . . . C12 C 0.60430(13) 0.31093(19) 0.70586(7) 0.0282(3) Uani 1 1 d . . . H12 H 0.5838 0.2399 0.7399 0.034 Uiso 1 1 calc R . . C13 C 0.71029(14) 0.3954(2) 0.71626(8) 0.0349(4) Uani 1 1 d . . . H13 H 0.7620 0.3810 0.7571 0.042 Uiso 1 1 calc R . . C14 C 0.74109(15) 0.5004(2) 0.66749(9) 0.0400(4) Uani 1 1 d . . . H14 H 0.8144 0.5560 0.6743 0.048 Uiso 1 1 calc R . . C15 C 0.66457(16) 0.5239(2) 0.60870(9) 0.0418(4) Uani 1 1 d . . . H15 H 0.6846 0.5978 0.5754 0.050 Uiso 1 1 calc R . . C16 C 0.55857(15) 0.4398(2) 0.59827(8) 0.0347(4) Uani 1 1 d . . . H16 H 0.5062 0.4579 0.5579 0.042 Uiso 1 1 calc R . . C17 C 0.40856(12) 0.04498(19) 0.68862(7) 0.0264(3) Uani 1 1 d . . . C18 C 0.36078(15) 0.0639(2) 0.74576(8) 0.0353(4) Uani 1 1 d . . . H18 H 0.3181 0.1657 0.7517 0.042 Uiso 1 1 calc R . . C19 C 0.37490(17) -0.0645(2) 0.79415(9) 0.0444(4) Uani 1 1 d . . . H19 H 0.3426 -0.0497 0.8332 0.053 Uiso 1 1 calc R . . C20 C 0.43581(16) -0.2137(2) 0.78561(9) 0.0407(4) Uani 1 1 d . . . H20 H 0.4455 -0.3016 0.8187 0.049 Uiso 1 1 calc R . . C21 C 0.48290(15) -0.2347(2) 0.72844(9) 0.0361(4) Uani 1 1 d . . . H21 H 0.5243 -0.3376 0.7223 0.043 Uiso 1 1 calc R . . C22 C 0.46960(13) -0.1060(2) 0.68051(8) 0.0309(4) Uani 1 1 d . . . H22 H 0.5024 -0.1209 0.6417 0.037 Uiso 1 1 calc R . . N1 N 0.21506(10) 0.15435(15) 0.50534(6) 0.0239(3) Uani 1 1 d . . . N2 N 0.35356(10) 0.01357(16) 0.45033(6) 0.0255(3) Uani 1 1 d . . . N3 N 0.40610(11) 0.12250(17) 0.55604(6) 0.0288(3) Uani 1 1 d D . . H3N H 0.4731(13) 0.084(2) 0.5516(9) 0.035 Uiso 1 1 d D . . P1 P 0.38553(3) 0.22281(5) 0.627796(17) 0.02584(17) 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 0.0275(8) 0.0442(10) 0.0364(10) 0.0027(7) 0.0083(7) 0.0051(7) C2 0.0351(9) 0.0521(11) 0.0513(11) 0.0042(9) 0.0182(8) 0.0122(8) C3 0.0247(8) 0.0441(10) 0.0657(12) 0.0152(9) 0.0148(8) 0.0079(7) C4 0.0234(8) 0.0452(10) 0.0551(12) 0.0089(8) -0.0014(8) 0.0002(7) C5 0.0250(8) 0.0394(9) 0.0426(10) 0.0026(7) 0.0015(7) 0.0006(6) C6 0.0228(7) 0.0247(7) 0.0321(8) 0.0075(6) 0.0053(6) -0.0008(6) C7 0.0216(7) 0.0238(7) 0.0251(7) 0.0052(5) 0.0041(6) -0.0026(5) C8 0.0260(8) 0.0387(9) 0.0239(7) -0.0020(6) 0.0004(6) -0.0024(6) C9 0.0292(8) 0.0371(9) 0.0222(7) -0.0053(6) 0.0054(6) -0.0002(6) C10 0.0219(7) 0.0256(7) 0.0209(7) 0.0018(5) 0.0053(6) 0.0010(5) C11 0.0279(7) 0.0243(7) 0.0240(7) -0.0030(6) 0.0052(6) 0.0057(6) C12 0.0316(8) 0.0291(8) 0.0228(7) -0.0020(6) 0.0022(6) 0.0016(6) C13 0.0340(9) 0.0371(9) 0.0319(9) -0.0097(6) 0.0012(7) -0.0017(7) C14 0.0386(9) 0.0367(9) 0.0472(10) -0.0140(7) 0.0142(8) -0.0108(7) C15 0.0558(11) 0.0335(9) 0.0397(10) 0.0012(7) 0.0185(9) -0.0083(8) C16 0.0439(9) 0.0344(9) 0.0251(8) 0.0028(6) 0.0046(7) 0.0020(7) C17 0.0213(7) 0.0315(8) 0.0264(7) -0.0053(6) 0.0042(6) -0.0036(6) C18 0.0419(9) 0.0327(8) 0.0355(9) -0.0025(7) 0.0185(7) 0.0020(7) C19 0.0598(11) 0.0399(10) 0.0404(10) 0.0040(7) 0.0280(9) -0.0003(8) C20 0.0481(10) 0.0326(9) 0.0433(10) 0.0074(7) 0.0135(8) -0.0028(7) C21 0.0337(9) 0.0306(8) 0.0443(10) -0.0011(7) 0.0079(8) 0.0017(6) C22 0.0254(7) 0.0371(9) 0.0311(8) -0.0053(6) 0.0077(6) 0.0015(6) N1 0.0217(6) 0.0281(7) 0.0222(6) 0.0015(5) 0.0048(5) 0.0014(5) N2 0.0235(6) 0.0314(7) 0.0220(6) -0.0018(5) 0.0050(5) 0.0017(5) N3 0.0200(6) 0.0439(8) 0.0219(7) -0.0062(5) 0.0028(5) 0.0078(5) P1 0.0228(2) 0.0345(3) 0.0204(3) -0.00369(14) 0.00410(16) 0.00609(14) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.387(2) . ? C1 C6 1.392(2) . ? C1 H1 0.9500 . ? C2 C3 1.380(3) . ? C2 H2 0.9500 . ? C3 C4 1.383(3) . ? C3 H3 0.9500 . ? C4 C5 1.385(2) . ? C4 H4 0.9500 . ? C5 C6 1.390(2) . ? C5 H5 0.9500 . ? C6 C7 1.485(2) . ? C7 N1 1.3367(19) . ? C7 C8 1.398(2) . ? C8 C9 1.370(2) . ? C8 H8 0.9500 . ? C9 N2 1.3344(19) . ? C9 H9 0.9500 . ? C10 N1 1.3345(18) . ? C10 N2 1.3522(18) . ? C10 N3 1.3661(18) . ? C11 C12 1.391(2) . ? C11 C16 1.393(2) . ? C11 P1 1.8416(15) . ? C12 C13 1.389(2) . ? C12 H12 0.9500 . ? C13 C14 1.382(2) . ? C13 H13 0.9500 . ? C14 C15 1.381(3) . ? C14 H14 0.9500 . ? C15 C16 1.387(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.392(2) . ? C17 C18 1.392(2) . ? C17 P1 1.8388(15) . ? C18 C19 1.389(2) . ? C18 H18 0.9500 . ? C19 C20 1.381(3) . ? C19 H19 0.9500 . ? C20 C21 1.390(3) . ? C20 H20 0.9500 . ? C21 C22 1.384(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? N3 P1 1.7148(12) . ? N3 H3N 0.863(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 C2 C1 C6 120.44(16) . . ? C2 C1 H1 119.8 . . ? C6 C1 H1 119.8 . . ? C3 C2 C1 120.45(17) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.61(15) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C4 C5 120.08(17) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.88(16) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 118.53(14) . . ? C5 C6 C7 122.07(14) . . ? C1 C6 C7 119.39(14) . . ? N1 C7 C8 120.14(13) . . ? N1 C7 C6 116.48(13) . . ? C8 C7 C6 123.38(13) . . ? C9 C8 C7 117.36(13) . . ? C9 C8 H8 121.3 . . ? C7 C8 H8 121.3 . . ? N2 C9 C8 123.83(13) . . ? N2 C9 H9 118.1 . . ? C8 C9 H9 118.1 . . ? N1 C10 N2 126.29(13) . . ? N1 C10 N3 117.99(12) . . ? N2 C10 N3 115.73(12) . . ? C12 C11 C16 118.24(14) . . ? C12 C11 P1 123.80(12) . . ? C16 C11 P1 117.91(11) . . ? C13 C12 C11 120.65(15) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.40(15) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.54(15) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.13(15) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.97(15) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C22 C17 C18 118.76(14) . . ? C22 C17 P1 123.96(12) . . ? C18 C17 P1 117.28(12) . . ? C19 C18 C17 120.64(15) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 120.09(16) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 119.74(16) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C22 C21 C20 120.13(15) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C17 120.63(15) . . ? C21 C22 H22 119.7 . . ? C17 C22 H22 119.7 . . ? C10 N1 C7 117.77(12) . . ? C9 N2 C10 114.57(12) . . ? C10 N3 P1 124.26(10) . . ? C10 N3 H3N 114.6(12) . . ? P1 N3 H3N 121.1(12) . . ? N3 P1 C17 102.64(7) . . ? N3 P1 C11 96.58(6) . . ? C17 P1 C11 100.03(6) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 62.77 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.225 _refine_diff_density_min -0.362 _refine_diff_density_rms 0.047 _database_code_depnum_ccdc_archive 'CCDC 960836' ####################################################################### # # 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_1 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H17 Au Cl N2 P' _chemical_formula_sum 'C21 H17 Au Cl N2 P' _chemical_formula_weight 560.75 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' P P 0.1023 0.0942 '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' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/a' _space_group_name_Hall '-P 2yab' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.5763(5) _cell_length_b 12.1434(5) _cell_length_c 14.4334(6) _cell_angle_alpha 90.00 _cell_angle_beta 107.456(3) _cell_angle_gamma 90.00 _cell_volume 1935.55(14) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 13748 _cell_measurement_theta_min 1.68 _cell_measurement_theta_max 29.59 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.239 _exptl_crystal_size_mid 0.185 _exptl_crystal_size_min 0.092 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.924 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 7.828 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.1875 _exptl_absorpt_correction_T_max 0.4152 _exptl_absorpt_process_details 'STOE X-RED & X-SHAPE' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10018 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.49 _reflns_number_total 3506 _reflns_number_gt 3033 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA, PLATON (A.L.Spek, 2005)' _computing_data_reduction 'STOE X-RED, PLATON (A.L.Spek, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 3.2g' _computing_publication_material 'OLEX 2, Microsoft Word' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^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 3506 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0574 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au -0.00903(2) 0.45960(2) 0.23447(2) 0.02653(7) Uani 1 1 d . . . . . Cl1 Cl 0.15212(13) 0.56443(10) 0.22963(12) 0.0506(3) Uani 1 1 d . . . . . P1 P -0.17739(10) 0.36460(9) 0.22541(8) 0.0245(2) Uani 1 1 d . . . . . N1 N -0.1088(4) 0.5393(3) 0.4018(3) 0.0303(8) Uani 1 1 d . . . . . N2 N -0.0170(4) 0.6094(3) 0.4456(3) 0.0341(9) Uani 1 1 d . . . . . H2 H 0.0460 0.5910 0.4947 0.041 Uiso 1 1 calc R U . . . C1 C -0.3078(4) 0.4541(4) 0.2153(3) 0.0267(9) Uani 1 1 d . . . . . C2 C -0.4208(4) 0.4252(4) 0.1501(4) 0.0367(11) Uani 1 1 d . . . . . H2A H -0.4285 0.3571 0.1164 0.044 Uiso 1 1 calc R U . . . C3 C -0.5203(5) 0.4926(5) 0.1338(4) 0.0470(13) Uani 1 1 d . . . . . H3 H -0.5955 0.4716 0.0891 0.056 Uiso 1 1 calc R U . . . C4 C -0.5094(5) 0.5921(5) 0.1835(5) 0.0483(13) Uani 1 1 d . . . . . H4 H -0.5777 0.6390 0.1735 0.058 Uiso 1 1 calc R U . . . C5 C -0.4004(4) 0.6225(4) 0.2469(4) 0.0362(10) Uani 1 1 d . . . . . H5 H -0.3944 0.6911 0.2795 0.043 Uiso 1 1 calc R U . . . C6 C -0.2980(4) 0.5561(3) 0.2651(3) 0.0269(9) Uani 1 1 d . . . . . C7 C -0.1848(4) 0.5996(3) 0.3321(3) 0.0275(9) Uani 1 1 d . . . . . C8 C -0.1405(5) 0.7074(4) 0.3316(4) 0.0372(11) Uani 1 1 d . . . . . H8 H -0.1771 0.7658 0.2891 0.045 Uiso 1 1 calc R U . . . C9 C -0.0338(5) 0.7104(4) 0.4050(4) 0.0377(11) Uani 1 1 d . . . . . H9 H 0.0186 0.7720 0.4239 0.045 Uiso 1 1 calc R U . . . C10 C -0.1746(4) 0.2652(3) 0.3204(3) 0.0271(9) Uani 1 1 d . . . . . C11 C -0.0976(5) 0.1747(4) 0.3313(4) 0.0384(11) Uani 1 1 d . . . . . H11 H -0.0408 0.1710 0.2957 0.046 Uiso 1 1 calc R U . . . C12 C -0.1038(6) 0.0901(4) 0.3940(4) 0.0502(15) Uani 1 1 d . . . . . H12 H -0.0525 0.0278 0.4000 0.060 Uiso 1 1 calc R U . . . C13 C -0.1843(6) 0.0960(4) 0.4480(4) 0.0479(14) Uani 1 1 d . . . . . H13 H -0.1887 0.0375 0.4905 0.057 Uiso 1 1 calc R U . . . C14 C -0.2573(5) 0.1858(5) 0.4401(4) 0.0487(14) Uani 1 1 d . . . . . H14 H -0.3109 0.1904 0.4786 0.058 Uiso 1 1 calc R U . . . C15 C -0.2541(5) 0.2710(4) 0.3761(4) 0.0372(11) Uani 1 1 d . . . . . H15 H -0.3061 0.3328 0.3705 0.045 Uiso 1 1 calc R U . . . C16 C -0.2196(4) 0.2798(3) 0.1165(3) 0.0266(9) Uani 1 1 d . . . . . C17 C -0.2990(4) 0.1906(4) 0.1067(4) 0.0330(10) Uani 1 1 d . . . . . H17 H -0.3287 0.1709 0.1590 0.040 Uiso 1 1 calc R U . . . C18 C -0.3345(5) 0.1311(4) 0.0210(4) 0.0406(11) Uani 1 1 d . . . . . H18 H -0.3901 0.0719 0.0141 0.049 Uiso 1 1 calc R U . . . C19 C -0.2893(5) 0.1575(4) -0.0546(4) 0.0417(12) Uani 1 1 d . . . . . H19 H -0.3136 0.1163 -0.1133 0.050 Uiso 1 1 calc R U . . . C20 C -0.2088(5) 0.2436(4) -0.0450(4) 0.0407(12) Uani 1 1 d . . . . . H20 H -0.1768 0.2608 -0.0967 0.049 Uiso 1 1 calc R U . . . C21 C -0.1744(4) 0.3054(4) 0.0401(3) 0.0318(10) Uani 1 1 d . . . . . H21 H -0.1199 0.3653 0.0459 0.038 Uiso 1 1 calc R U . . . 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 Au1 0.02276(10) 0.02535(10) 0.03101(11) -0.00226(7) 0.00735(6) -0.00207(7) Cl1 0.0352(7) 0.0373(6) 0.0801(11) 0.0021(6) 0.0187(6) -0.0110(5) P1 0.0234(5) 0.0263(5) 0.0239(6) -0.0017(4) 0.0071(4) -0.0016(4) N1 0.031(2) 0.0312(18) 0.026(2) -0.0010(16) 0.0053(15) 0.0025(16) N2 0.032(2) 0.036(2) 0.029(2) -0.0040(16) 0.0024(16) -0.0003(17) C1 0.027(2) 0.030(2) 0.024(2) 0.0026(17) 0.0083(17) -0.0005(18) C2 0.027(2) 0.038(2) 0.042(3) -0.007(2) 0.005(2) -0.0039(19) C3 0.025(3) 0.059(3) 0.052(4) -0.004(3) 0.003(2) 0.000(2) C4 0.034(3) 0.051(3) 0.059(4) 0.007(3) 0.014(2) 0.013(2) C5 0.033(3) 0.037(2) 0.038(3) -0.002(2) 0.010(2) 0.007(2) C6 0.029(2) 0.029(2) 0.022(2) 0.0033(16) 0.0076(17) 0.0012(18) C7 0.030(2) 0.031(2) 0.022(2) -0.0021(17) 0.0084(17) 0.0036(18) C8 0.046(3) 0.030(2) 0.033(3) 0.0019(19) 0.007(2) 0.002(2) C9 0.041(3) 0.033(2) 0.035(3) -0.003(2) 0.005(2) -0.006(2) C10 0.027(2) 0.027(2) 0.025(2) -0.0008(16) 0.0048(17) -0.0035(17) C11 0.038(3) 0.044(3) 0.029(3) 0.003(2) 0.005(2) 0.008(2) C12 0.073(4) 0.034(3) 0.035(3) 0.003(2) 0.003(3) 0.009(3) C13 0.054(3) 0.044(3) 0.037(3) 0.011(2) 0.000(2) -0.013(3) C14 0.042(3) 0.068(4) 0.037(3) 0.011(3) 0.014(2) -0.010(3) C15 0.033(3) 0.045(3) 0.036(3) 0.005(2) 0.014(2) 0.000(2) C16 0.027(2) 0.027(2) 0.024(2) 0.0003(16) 0.0051(17) 0.0024(17) C17 0.031(2) 0.035(2) 0.036(3) -0.0043(19) 0.013(2) -0.0103(19) C18 0.038(3) 0.035(2) 0.046(3) -0.013(2) 0.009(2) -0.007(2) C19 0.049(3) 0.043(3) 0.029(3) -0.012(2) 0.005(2) 0.005(2) C20 0.051(3) 0.047(3) 0.026(3) -0.001(2) 0.013(2) 0.002(2) C21 0.032(2) 0.032(2) 0.032(3) -0.0011(18) 0.0115(19) -0.0039(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 P1 2.2347(11) . ? Au1 Cl1 2.2768(13) . ? P1 C16 1.820(4) . ? P1 C10 1.820(4) . ? P1 C1 1.830(5) . ? N1 C7 1.339(6) . ? N1 N2 1.360(5) . ? N2 C9 1.347(6) . ? N2 H2 0.8800 . ? C1 C2 1.408(6) . ? C1 C6 1.419(6) . ? C2 C3 1.375(7) . ? C2 H2A 0.9500 . ? C3 C4 1.391(8) . ? C3 H3 0.9500 . ? C4 C5 1.368(8) . ? C4 H4 0.9500 . ? C5 C6 1.392(6) . ? C5 H5 0.9500 . ? C6 C7 1.474(6) . ? C7 C8 1.406(7) . ? C8 C9 1.366(7) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.394(7) . ? C10 C15 1.394(7) . ? C11 C12 1.385(8) . ? C11 H11 0.9500 . ? C12 C13 1.384(9) . ? C12 H12 0.9500 . ? C13 C14 1.364(8) . ? C13 H13 0.9500 . ? C14 C15 1.394(7) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C21 1.390(6) . ? C16 C17 1.400(6) . ? C17 C18 1.385(7) . ? C17 H17 0.9500 . ? C18 C19 1.382(8) . ? C18 H18 0.9500 . ? C19 C20 1.380(8) . ? C19 H19 0.9500 . ? C20 C21 1.391(7) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? 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 P1 Au1 Cl1 174.34(5) . . ? C16 P1 C10 102.4(2) . . ? C16 P1 C1 105.5(2) . . ? C10 P1 C1 106.3(2) . . ? C16 P1 Au1 110.25(15) . . ? C10 P1 Au1 118.70(15) . . ? C1 P1 Au1 112.47(15) . . ? C7 N1 N2 104.6(3) . . ? C9 N2 N1 112.2(4) . . ? C9 N2 H2 123.9 . . ? N1 N2 H2 123.9 . . ? C2 C1 C6 118.3(4) . . ? C2 C1 P1 118.9(3) . . ? C6 C1 P1 122.6(3) . . ? C3 C2 C1 121.9(5) . . ? C3 C2 H2A 119.1 . . ? C1 C2 H2A 119.1 . . ? C2 C3 C4 119.2(5) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 120.1(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 122.2(5) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 118.4(4) . . ? C5 C6 C7 117.1(4) . . ? C1 C6 C7 124.4(4) . . ? N1 C7 C8 110.8(4) . . ? N1 C7 C6 123.5(4) . . ? C8 C7 C6 125.7(4) . . ? C9 C8 C7 105.5(4) . . ? C9 C8 H8 127.3 . . ? C7 C8 H8 127.3 . . ? N2 C9 C8 107.0(4) . . ? N2 C9 H9 126.5 . . ? C8 C9 H9 126.5 . . ? C11 C10 C15 119.0(4) . . ? C11 C10 P1 118.3(4) . . ? C15 C10 P1 122.4(4) . . ? C12 C11 C10 120.1(5) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 120.4(5) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 119.9(5) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.6(5) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 119.9(5) . . ? C14 C15 H15 120.1 . . ? C10 C15 H15 120.1 . . ? C21 C16 C17 119.0(4) . . ? C21 C16 P1 119.4(3) . . ? C17 C16 P1 121.5(3) . . ? C18 C17 C16 120.2(5) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C19 C18 C17 120.2(5) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 120.0(5) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 120.3(5) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C16 C21 C20 120.2(4) . . ? C16 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 1.213 _refine_diff_density_min -2.332 _refine_diff_density_rms 0.140 _database_code_depnum_ccdc_archive 'CCDC 960837' ####################################################################### # # 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_3 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H17 Au Cl N4 P, C H2 Cl2' _chemical_formula_sum 'C22 H19 Au Cl3 N4 P' _chemical_formula_weight 673.70 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0659(4) _cell_length_b 11.2041(4) _cell_length_c 11.2375(4) _cell_angle_alpha 87.414(3) _cell_angle_beta 71.501(3) _cell_angle_gamma 82.113(3) _cell_volume 1190.51(8) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 21074 _cell_measurement_theta_min 1.84 _cell_measurement_theta_max 29.57 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.409 _exptl_crystal_size_mid 0.241 _exptl_crystal_size_min 0.126 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.879 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 6.600 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.1280 _exptl_absorpt_correction_T_max 0.4683 _exptl_absorpt_process_details 'STOE X-RED & X-SHAPE' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11647 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4397 _reflns_number_gt 4260 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA, PLATON (A.L.Spek, 2005)' _computing_data_reduction 'STOE X-RED, PLATON (A.L.Spek, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 3.2g' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0261P)^2^+0.5304P] 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 4397 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0206 _refine_ls_R_factor_gt 0.0197 _refine_ls_wR_factor_ref 0.0490 _refine_ls_wR_factor_gt 0.0486 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.78760(2) 0.17728(2) 0.09280(2) 0.03124(5) Uani 1 1 d . . . . . Cl1 Cl 0.77885(11) 0.34175(9) -0.03212(10) 0.0631(3) Uani 1 1 d . . . . . Cl2 Cl 0.59750(10) 0.53280(9) 0.81565(8) 0.0535(2) Uani 1 1 d . . . . . Cl3 Cl 0.64720(15) 0.77873(10) 0.73246(12) 0.0749(3) Uani 1 1 d . . . . . P1 P 0.78694(7) 0.02041(6) 0.22122(6) 0.02554(13) Uani 1 1 d . . . . . N1 N 0.6566(2) 0.0373(2) 0.3601(2) 0.0289(5) Uani 1 1 d . . . . . H1 H 0.6051 -0.0215 0.3890 0.035 Uiso 1 1 calc R U . . . N2 N 0.5114(2) 0.1563(2) 0.5282(2) 0.0292(5) Uani 1 1 d . . . . . N3 N 0.7252(2) 0.2186(2) 0.3889(2) 0.0269(4) Uani 1 1 d . . . . . N4 N 0.7767(3) 0.5132(2) 0.4669(2) 0.0363(5) Uani 1 1 d . . . . . C1 C 0.9500(3) -0.0205(2) 0.2574(3) 0.0298(5) Uani 1 1 d . . . . . C2 C 1.0744(3) 0.0142(3) 0.1768(3) 0.0365(6) Uani 1 1 d . . . . . H2 H 1.0731 0.0620 0.1051 0.044 Uiso 1 1 calc R U . . . C3 C 1.2020(3) -0.0212(4) 0.2013(3) 0.0502(8) Uani 1 1 d . . . . . H3 H 1.2879 0.0005 0.1450 0.060 Uiso 1 1 calc R U . . . C4 C 1.2025(4) -0.0878(4) 0.3076(4) 0.0550(9) Uani 1 1 d . . . . . H4 H 1.2891 -0.1117 0.3244 0.066 Uiso 1 1 calc R U . . . C5 C 1.0782(4) -0.1198(3) 0.3897(4) 0.0515(8) Uani 1 1 d . . . . . H5 H 1.0790 -0.1641 0.4636 0.062 Uiso 1 1 calc R U . . . C6 C 0.9524(4) -0.0872(3) 0.3639(3) 0.0390(7) Uani 1 1 d . . . . . H6 H 0.8671 -0.1106 0.4196 0.047 Uiso 1 1 calc R U . . . C7 C 0.7474(3) -0.1149(3) 0.1627(2) 0.0285(5) Uani 1 1 d . . . . . C8 C 0.8400(3) -0.2212(3) 0.1425(3) 0.0343(6) Uani 1 1 d . . . . . H8 H 0.9264 -0.2258 0.1609 0.041 Uiso 1 1 calc R U . . . C9 C 0.8055(4) -0.3216(3) 0.0947(3) 0.0439(8) Uani 1 1 d . . . . . H9 H 0.8686 -0.3945 0.0804 0.053 Uiso 1 1 calc R U . . . C10 C 0.6799(4) -0.3149(3) 0.0682(3) 0.0460(8) Uani 1 1 d . . . . . H10 H 0.6560 -0.3838 0.0371 0.055 Uiso 1 1 calc R U . . . C11 C 0.5888(4) -0.2085(3) 0.0866(3) 0.0449(8) Uani 1 1 d . . . . . H11 H 0.5030 -0.2043 0.0673 0.054 Uiso 1 1 calc R U . . . C12 C 0.6216(3) -0.1077(3) 0.1332(3) 0.0371(6) Uani 1 1 d . . . . . H12 H 0.5592 -0.0344 0.1449 0.045 Uiso 1 1 calc R U . . . C13 C 0.6294(3) 0.1415(2) 0.4291(2) 0.0264(5) Uani 1 1 d . . . . . C14 C 0.4859(3) 0.2624(3) 0.5876(2) 0.0316(6) Uani 1 1 d . . . . . H14 H 0.4030 0.2777 0.6577 0.038 Uiso 1 1 calc R U . . . C15 C 0.5750(3) 0.3506(3) 0.5514(3) 0.0327(6) Uani 1 1 d . . . . . H15 H 0.5536 0.4258 0.5935 0.039 Uiso 1 1 calc R U . . . C16 C 0.6968(3) 0.3237(2) 0.4506(2) 0.0269(5) Uani 1 1 d . . . . . C17 C 0.8047(3) 0.4084(3) 0.4047(3) 0.0297(5) Uani 1 1 d . . . . . C18 C 0.9262(3) 0.3770(3) 0.3054(3) 0.0401(7) Uani 1 1 d . . . . . H18 H 0.9419 0.3018 0.2641 0.048 Uiso 1 1 calc R U . . . C19 C 1.0251(3) 0.4582(3) 0.2673(3) 0.0450(7) Uani 1 1 d . . . . . H19 H 1.1089 0.4399 0.1985 0.054 Uiso 1 1 calc R U . . . C20 C 0.9994(4) 0.5650(3) 0.3307(3) 0.0427(7) Uani 1 1 d . . . . . H20 H 1.0657 0.6214 0.3080 0.051 Uiso 1 1 calc R U . . . C21 C 0.8749(4) 0.5887(3) 0.4286(3) 0.0437(7) Uani 1 1 d . . . . . H21 H 0.8576 0.6631 0.4715 0.052 Uiso 1 1 calc R U . . . C22 C 0.5571(4) 0.6565(3) 0.7250(3) 0.0504(8) Uani 1 1 d . . . . . H22A H 0.4540 0.6829 0.7552 0.061 Uiso 1 1 calc R U . . . H22B H 0.5826 0.6309 0.6365 0.061 Uiso 1 1 calc R U . . . 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 Au1 0.03157(7) 0.02937(7) 0.02785(7) 0.00593(4) -0.00362(5) -0.00295(5) Cl1 0.0608(5) 0.0496(5) 0.0579(5) 0.0295(4) 0.0011(4) 0.0072(4) Cl2 0.0544(5) 0.0658(6) 0.0465(4) 0.0028(4) -0.0226(4) -0.0135(4) Cl3 0.1090(9) 0.0513(6) 0.0748(7) -0.0078(5) -0.0463(7) -0.0013(6) P1 0.0269(3) 0.0251(3) 0.0232(3) 0.0012(2) -0.0050(2) -0.0058(3) N1 0.0322(11) 0.0247(11) 0.0264(11) 0.0003(9) -0.0024(9) -0.0086(9) N2 0.0296(11) 0.0302(12) 0.0258(11) 0.0005(9) -0.0043(9) -0.0080(9) N3 0.0286(11) 0.0252(11) 0.0268(10) 0.0016(8) -0.0074(9) -0.0070(9) N4 0.0403(13) 0.0302(13) 0.0371(13) 0.0002(10) -0.0073(11) -0.0117(11) C1 0.0326(14) 0.0279(13) 0.0307(13) -0.0025(10) -0.0111(11) -0.0059(11) C2 0.0324(14) 0.0418(17) 0.0337(14) -0.0029(12) -0.0063(12) -0.0077(13) C3 0.0293(15) 0.066(2) 0.054(2) -0.0092(17) -0.0089(14) -0.0083(15) C4 0.0449(19) 0.063(2) 0.065(2) -0.0080(19) -0.0317(18) 0.0012(17) C5 0.061(2) 0.051(2) 0.052(2) 0.0058(16) -0.0340(18) -0.0054(17) C6 0.0450(17) 0.0354(16) 0.0392(16) 0.0074(13) -0.0156(13) -0.0111(14) C7 0.0317(13) 0.0314(14) 0.0208(11) 0.0005(10) -0.0047(10) -0.0077(11) C8 0.0369(15) 0.0329(15) 0.0315(13) -0.0036(11) -0.0087(11) -0.0036(12) C9 0.0517(19) 0.0382(19) 0.0389(18) -0.0102(14) -0.0092(15) -0.0054(16) C10 0.058(2) 0.0452(19) 0.0366(16) -0.0097(13) -0.0113(14) -0.0192(17) C11 0.0462(18) 0.056(2) 0.0393(16) -0.0042(14) -0.0189(14) -0.0144(16) C12 0.0384(15) 0.0396(17) 0.0346(14) 0.0003(12) -0.0126(12) -0.0065(13) C13 0.0290(12) 0.0270(13) 0.0241(12) 0.0029(10) -0.0090(10) -0.0059(10) C14 0.0339(14) 0.0335(15) 0.0234(12) -0.0010(11) -0.0027(11) -0.0058(12) C15 0.0367(14) 0.0304(14) 0.0291(13) -0.0043(11) -0.0058(11) -0.0069(12) C16 0.0308(13) 0.0264(13) 0.0246(12) 0.0038(9) -0.0098(10) -0.0064(11) C17 0.0316(13) 0.0289(14) 0.0299(13) 0.0033(11) -0.0099(11) -0.0088(11) C18 0.0401(16) 0.0369(16) 0.0407(16) -0.0047(13) -0.0056(13) -0.0122(13) C19 0.0373(16) 0.0479(19) 0.0459(17) 0.0033(14) -0.0035(13) -0.0171(15) C20 0.0483(18) 0.0388(17) 0.0463(17) 0.0106(14) -0.0164(14) -0.0231(15) C21 0.0531(19) 0.0337(16) 0.0465(17) 0.0005(13) -0.0139(15) -0.0175(15) C22 0.0478(19) 0.059(2) 0.0444(18) -0.0116(16) -0.0201(15) 0.0096(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 P1 2.2225(10) . ? Au1 Cl1 2.2748(11) . ? Cl2 C22 1.762(4) . ? Cl3 C22 1.762(4) . ? P1 N1 1.689(2) . ? P1 C1 1.808(3) . ? P1 C7 1.820(3) . ? N1 C13 1.378(3) . ? N1 H1 0.8800 . ? N2 C14 1.342(4) . ? N2 C13 1.343(4) . ? N3 C13 1.341(3) . ? N3 C16 1.343(4) . ? N4 C21 1.343(4) . ? N4 C17 1.343(4) . ? C1 C2 1.387(4) . ? C1 C6 1.387(4) . ? C2 C3 1.399(5) . ? C2 H2 0.9500 . ? C3 C4 1.380(6) . ? C3 H3 0.9500 . ? C4 C5 1.381(6) . ? C4 H4 0.9500 . ? C5 C6 1.384(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.388(4) . ? C7 C12 1.398(4) . ? C8 C9 1.398(4) . ? C8 H8 0.9500 . ? C9 C10 1.380(5) . ? C9 H9 0.9500 . ? C10 C11 1.381(5) . ? C10 H10 0.9500 . ? C11 C12 1.386(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C14 C15 1.386(4) . ? C14 H14 0.9500 . ? C15 C16 1.388(4) . ? C15 H15 0.9500 . ? C16 C17 1.493(4) . ? C17 C18 1.384(4) . ? C18 C19 1.395(4) . ? C18 H18 0.9500 . ? C19 C20 1.371(5) . ? C19 H19 0.9500 . ? C20 C21 1.383(5) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? 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 P1 Au1 Cl1 177.35(3) . . ? N1 P1 C1 106.47(12) . . ? N1 P1 C7 100.56(12) . . ? C1 P1 C7 106.77(13) . . ? N1 P1 Au1 114.05(9) . . ? C1 P1 Au1 114.64(10) . . ? C7 P1 Au1 113.13(9) . . ? C13 N1 P1 121.10(18) . . ? C13 N1 H1 119.4 . . ? P1 N1 H1 119.4 . . ? C14 N2 C13 115.2(2) . . ? C13 N3 C16 116.6(2) . . ? C21 N4 C17 116.4(3) . . ? C2 C1 C6 119.6(3) . . ? C2 C1 P1 119.5(2) . . ? C6 C1 P1 120.9(2) . . ? C1 C2 C3 119.9(3) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.5(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 120.4(3) . . ? C5 C6 H6 119.8 . . ? C1 C6 H6 119.8 . . ? C8 C7 C12 120.1(3) . . ? C8 C7 P1 122.0(2) . . ? C12 C7 P1 117.8(2) . . ? C7 C8 C9 119.5(3) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 C8 120.2(3) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.2(3) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 119.4(3) . . ? C11 C12 H12 120.3 . . ? C7 C12 H12 120.3 . . ? N3 C13 N2 126.6(2) . . ? N3 C13 N1 115.6(2) . . ? N2 C13 N1 117.7(2) . . ? N2 C14 C15 123.1(3) . . ? N2 C14 H14 118.5 . . ? C15 C14 H14 118.5 . . ? C14 C15 C16 116.8(3) . . ? C14 C15 H15 121.6 . . ? C16 C15 H15 121.6 . . ? N3 C16 C15 121.6(2) . . ? N3 C16 C17 115.9(2) . . ? C15 C16 C17 122.5(2) . . ? N4 C17 C18 123.5(3) . . ? N4 C17 C16 115.9(2) . . ? C18 C17 C16 120.6(3) . . ? C17 C18 C19 118.6(3) . . ? C17 C18 H18 120.7 . . ? C19 C18 H18 120.7 . . ? C20 C19 C18 118.8(3) . . ? C20 C19 H19 120.6 . . ? C18 C19 H19 120.6 . . ? C19 C20 C21 118.5(3) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? N4 C21 C20 124.2(3) . . ? N4 C21 H21 117.9 . . ? C20 C21 H21 117.9 . . ? Cl2 C22 Cl3 112.30(18) . . ? Cl2 C22 H22A 109.1 . . ? Cl3 C22 H22A 109.1 . . ? Cl2 C22 H22B 109.1 . . ? Cl3 C22 H22B 109.1 . . ? H22A C22 H22B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.145 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.080 _database_code_depnum_ccdc_archive 'CCDC 960838' ####################################################################### # # 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_4 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H18 Au Cl N3 P' _chemical_formula_sum 'C22 H18 Au Cl N3 P' _chemical_formula_weight 587.78 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8010(4) _cell_length_b 11.0375(4) _cell_length_c 11.7633(5) _cell_angle_alpha 74.503(3) _cell_angle_beta 71.796(3) _cell_angle_gamma 77.520(3) _cell_volume 1035.01(8) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 19116 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 29.61 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.371 _exptl_crystal_size_mid 0.209 _exptl_crystal_size_min 0.127 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.886 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 7.326 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.2530 _exptl_absorpt_correction_T_max 0.4661 _exptl_absorpt_process_details 'STOE X-RED & X-SHAPE' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12718 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 29.16 _reflns_number_total 5472 _reflns_number_gt 5203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA, PLATON (A.L.Spek, 2005)' _computing_data_reduction 'STOE X-RED, PLATON (A.L.Spek, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 3.2g' _computing_publication_material 'OLEX 2, Microsoft Word' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.8487P] 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 5472 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0253 _refine_ls_R_factor_gt 0.0236 _refine_ls_wR_factor_ref 0.0613 _refine_ls_wR_factor_gt 0.0605 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.27310(2) 0.87459(2) 0.60140(2) 0.03052(4) Uani 1 1 d . . . . . Cl1 Cl 0.21723(11) 0.76029(9) 0.48733(9) 0.04677(19) Uani 1 1 d . . . . . P1 P 0.31465(9) 0.98333(7) 0.72084(7) 0.02732(13) Uani 1 1 d . . . . . N1 N 0.1847(3) 0.9609(2) 0.8639(2) 0.0311(5) Uani 1 1 d . . . . . H1 H 0.1364 1.0265 0.8973 0.037 Uiso 1 1 calc R U . . . N2 N 0.0232(3) 0.8300(2) 1.0230(2) 0.0347(5) Uani 1 1 d . . . . . N3 N 0.2623(3) 0.7450(2) 0.8864(2) 0.0310(5) Uani 1 1 d . . . . . C1 C 0.2663(4) 1.1542(3) 0.6713(3) 0.0294(5) Uani 1 1 d . . . . . C2 C 0.3708(4) 1.2385(3) 0.6582(3) 0.0378(6) Uani 1 1 d . . . . . H2 H 0.4730 1.2074 0.6744 0.045 Uiso 1 1 calc R U . . . C3 C 0.3245(5) 1.3695(3) 0.6207(4) 0.0448(8) Uani 1 1 d . . . . . H3 H 0.3955 1.4274 0.6114 0.054 Uiso 1 1 calc R U . . . C4 C 0.1758(5) 1.4143(3) 0.5975(3) 0.0448(8) Uani 1 1 d . . . . . H4 H 0.1439 1.5032 0.5739 0.054 Uiso 1 1 calc R U . . . C5 C 0.0728(5) 1.3308(3) 0.6084(4) 0.0441(8) Uani 1 1 d . . . . . H5 H -0.0291 1.3625 0.5917 0.053 Uiso 1 1 calc R U . . . C6 C 0.1184(4) 1.1995(3) 0.6439(3) 0.0382(6) Uani 1 1 d . . . . . H6 H 0.0491 1.1419 0.6493 0.046 Uiso 1 1 calc R U . . . C7 C 0.5175(3) 0.9503(3) 0.7392(3) 0.0301(5) Uani 1 1 d . . . . . C8 C 0.6386(4) 0.8798(3) 0.6632(3) 0.0358(6) Uani 1 1 d . . . . . H8 H 0.6139 0.8501 0.6032 0.043 Uiso 1 1 calc R U . . . C9 C 0.7949(4) 0.8535(4) 0.6755(4) 0.0471(8) Uani 1 1 d . . . . . H9 H 0.8775 0.8062 0.6236 0.057 Uiso 1 1 calc R U . . . C10 C 0.8304(5) 0.8962(4) 0.7639(4) 0.0498(8) Uani 1 1 d . . . . . H10 H 0.9371 0.8767 0.7730 0.060 Uiso 1 1 calc R U . . . C11 C 0.7112(5) 0.9671(4) 0.8394(3) 0.0458(8) Uani 1 1 d . . . . . H11 H 0.7366 0.9977 0.8985 0.055 Uiso 1 1 calc R U . . . C12 C 0.5538(4) 0.9930(3) 0.8273(3) 0.0374(6) Uani 1 1 d . . . . . H12 H 0.4712 1.0400 0.8795 0.045 Uiso 1 1 calc R U . . . C13 C 0.1553(4) 0.8402(3) 0.9274(3) 0.0300(5) Uani 1 1 d . . . . . C14 C -0.0041(4) 0.7104(3) 1.0776(3) 0.0392(7) Uani 1 1 d . . . . . H14 H -0.0977 0.6974 1.1443 0.047 Uiso 1 1 calc R U . . . C15 C 0.0979(4) 0.6051(3) 1.0412(3) 0.0382(7) Uani 1 1 d . . . . . H15 H 0.0746 0.5215 1.0807 0.046 Uiso 1 1 calc R U . . . C16 C 0.2362(4) 0.6260(3) 0.9443(3) 0.0310(5) Uani 1 1 d . . . . . C17 C 0.3620(4) 0.5230(3) 0.8995(3) 0.0348(6) Uani 1 1 d . . . . . C18 C 0.3677(5) 0.3974(3) 0.9667(3) 0.0425(7) Uani 1 1 d . . . . . H18 H 0.2865 0.3753 1.0409 0.051 Uiso 1 1 calc R U . . . C19 C 0.4918(5) 0.3053(3) 0.9251(4) 0.0461(8) Uani 1 1 d . . . . . H19 H 0.4954 0.2205 0.9717 0.055 Uiso 1 1 calc R U . . . C20 C 0.6096(5) 0.3344(3) 0.8180(4) 0.0480(8) Uani 1 1 d . . . . . H20 H 0.6939 0.2702 0.7904 0.058 Uiso 1 1 calc R U . . . C21 C 0.6043(5) 0.4586(4) 0.7500(4) 0.0536(10) Uani 1 1 d . . . . . H21 H 0.6853 0.4796 0.6755 0.064 Uiso 1 1 calc R U . . . C22 C 0.4817(5) 0.5519(3) 0.7906(3) 0.0448(8) Uani 1 1 d . . . . . H22 H 0.4791 0.6366 0.7436 0.054 Uiso 1 1 calc R U . . . 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 Au1 0.02888(6) 0.03195(6) 0.03186(7) -0.01046(4) -0.00618(4) -0.00528(4) Cl1 0.0402(4) 0.0569(5) 0.0528(5) -0.0285(4) -0.0066(3) -0.0150(3) P1 0.0260(3) 0.0281(3) 0.0268(3) -0.0069(2) -0.0051(3) -0.0034(2) N1 0.0314(12) 0.0293(11) 0.0289(11) -0.0079(9) -0.0026(9) -0.0028(9) N2 0.0350(13) 0.0336(12) 0.0323(12) -0.0094(10) -0.0011(10) -0.0073(10) N3 0.0313(12) 0.0293(11) 0.0310(12) -0.0071(9) -0.0056(9) -0.0048(9) C1 0.0313(13) 0.0283(12) 0.0272(12) -0.0053(9) -0.0067(10) -0.0043(10) C2 0.0322(14) 0.0356(14) 0.0431(17) -0.0027(12) -0.0086(12) -0.0095(11) C3 0.0467(19) 0.0338(15) 0.052(2) -0.0018(13) -0.0107(15) -0.0144(13) C4 0.059(2) 0.0304(14) 0.0434(18) -0.0012(12) -0.0191(16) -0.0044(13) C5 0.0490(19) 0.0346(15) 0.053(2) -0.0045(13) -0.0272(16) 0.0000(13) C6 0.0411(16) 0.0319(14) 0.0461(17) -0.0087(12) -0.0195(14) -0.0024(12) C7 0.0277(13) 0.0313(12) 0.0281(12) -0.0047(10) -0.0046(10) -0.0039(10) C8 0.0299(14) 0.0406(15) 0.0346(14) -0.0102(12) -0.0058(11) -0.0023(11) C9 0.0286(15) 0.058(2) 0.049(2) -0.0157(16) -0.0053(14) 0.0022(14) C10 0.0309(16) 0.063(2) 0.055(2) -0.0079(17) -0.0159(15) -0.0056(14) C11 0.0433(18) 0.059(2) 0.0398(17) -0.0079(15) -0.0184(15) -0.0103(15) C12 0.0349(15) 0.0422(15) 0.0350(15) -0.0089(12) -0.0091(12) -0.0052(12) C13 0.0307(13) 0.0302(12) 0.0291(13) -0.0072(10) -0.0069(10) -0.0053(10) C14 0.0407(16) 0.0390(15) 0.0338(15) -0.0078(12) 0.0012(12) -0.0139(12) C15 0.0427(17) 0.0307(13) 0.0365(15) -0.0049(11) -0.0019(13) -0.0117(12) C16 0.0357(14) 0.0293(12) 0.0289(13) -0.0078(10) -0.0083(11) -0.0052(10) C17 0.0392(15) 0.0302(13) 0.0367(15) -0.0107(11) -0.0112(12) -0.0023(11) C18 0.0492(19) 0.0313(14) 0.0453(18) -0.0079(13) -0.0101(15) -0.0068(13) C19 0.057(2) 0.0285(14) 0.053(2) -0.0070(13) -0.0214(17) -0.0012(13) C20 0.052(2) 0.0374(16) 0.056(2) -0.0156(15) -0.0189(17) 0.0047(14) C21 0.054(2) 0.0430(18) 0.049(2) -0.0112(15) 0.0002(17) 0.0046(16) C22 0.0482(19) 0.0335(14) 0.0435(18) -0.0077(13) -0.0037(15) -0.0007(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 P1 2.2271(9) . ? Au1 Cl1 2.2845(10) . ? P1 N1 1.702(3) . ? P1 C7 1.813(3) . ? P1 C1 1.816(3) . ? N1 C13 1.377(4) . ? N1 H1 0.8800 . ? N2 C14 1.342(4) . ? N2 C13 1.342(4) . ? N3 C13 1.336(4) . ? N3 C16 1.340(4) . ? C1 C2 1.392(4) . ? C1 C6 1.394(4) . ? C2 C3 1.403(5) . ? C2 H2 0.9500 . ? C3 C4 1.379(6) . ? C3 H3 0.9500 . ? C4 C5 1.383(5) . ? C4 H4 0.9500 . ? C5 C6 1.402(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.389(4) . ? C7 C8 1.399(4) . ? C8 C9 1.388(5) . ? C8 H8 0.9500 . ? C9 C10 1.389(6) . ? C9 H9 0.9500 . ? C10 C11 1.392(6) . ? C10 H10 0.9500 . ? C11 C12 1.397(5) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C14 C15 1.384(5) . ? C14 H14 0.9500 . ? C15 C16 1.396(4) . ? C15 H15 0.9500 . ? C16 C17 1.486(4) . ? C17 C22 1.392(5) . ? C17 C18 1.400(4) . ? C18 C19 1.385(5) . ? C18 H18 0.9500 . ? C19 C20 1.370(6) . ? C19 H19 0.9500 . ? C20 C21 1.390(5) . ? C20 H20 0.9500 . ? C21 C22 1.383(5) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? 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 P1 Au1 Cl1 176.72(3) . . ? N1 P1 C7 107.15(14) . . ? N1 P1 C1 99.91(13) . . ? C7 P1 C1 107.69(14) . . ? N1 P1 Au1 112.81(10) . . ? C7 P1 Au1 114.81(10) . . ? C1 P1 Au1 113.25(10) . . ? C13 N1 P1 120.1(2) . . ? C13 N1 H1 120.0 . . ? P1 N1 H1 120.0 . . ? C14 N2 C13 114.7(3) . . ? C13 N3 C16 117.8(3) . . ? C2 C1 C6 120.1(3) . . ? C2 C1 P1 122.9(2) . . ? C6 C1 P1 117.0(2) . . ? C1 C2 C3 119.7(3) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.0(3) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.5(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 120.2(3) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 119.5(3) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C12 C7 C8 120.0(3) . . ? C12 C7 P1 121.2(2) . . ? C8 C7 P1 118.8(2) . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 120.0(3) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C11 120.7(3) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C12 119.3(3) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C7 C12 C11 120.3(3) . . ? C7 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? N3 C13 N2 126.8(3) . . ? N3 C13 N1 115.9(3) . . ? N2 C13 N1 117.3(3) . . ? N2 C14 C15 123.0(3) . . ? N2 C14 H14 118.5 . . ? C15 C14 H14 118.5 . . ? C14 C15 C16 117.7(3) . . ? C14 C15 H15 121.2 . . ? C16 C15 H15 121.2 . . ? N3 C16 C15 119.9(3) . . ? N3 C16 C17 116.1(3) . . ? C15 C16 C17 124.0(3) . . ? C22 C17 C18 118.6(3) . . ? C22 C17 C16 119.6(3) . . ? C18 C17 C16 121.7(3) . . ? C19 C18 C17 119.9(3) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 121.2(3) . . ? C20 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? C19 C20 C21 119.3(3) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C22 C21 C20 120.2(4) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C17 120.7(3) . . ? C21 C22 H22 119.7 . . ? C17 C22 H22 119.7 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 29.16 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.892 _refine_diff_density_min -1.075 _refine_diff_density_rms 0.099 _database_code_depnum_ccdc_archive 'CCDC 960839' ####################################################################### # # 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_5 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C42 H34 Au N4 P2, 3(C H Cl3), Cl O4' _chemical_formula_sum 'C45 H37 Au Cl10 N4 O4 P2' _chemical_formula_weight 1311.19 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9679(3) _cell_length_b 13.2655(3) _cell_length_c 18.0039(5) _cell_angle_alpha 91.400(2) _cell_angle_beta 99.377(2) _cell_angle_gamma 103.517(2) _cell_volume 2507.54(12) _cell_formula_units_Z 2 _cell_measurement_reflns_used 56756 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 25.50 _cell_measurement_theta_min 2.30 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.429 _exptl_crystal_size_mid 0.203 _exptl_crystal_size_min 0.038 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.737 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1292 _exptl_absorpt_coefficient_mu 3.577 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_max 0.8780 _exptl_absorpt_correction_T_min 0.3650 _shelx_estimated_absorpt_T_min 0.309 _shelx_estimated_absorpt_T_max 0.876 _exptl_absorpt_process_details 'STOE X-RED & X-SHAPE' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source ? _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean 6.67 _diffrn_reflns_number 59074 _diffrn_reflns_av_unetI/netI 0.0379 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.298 _diffrn_reflns_theta_max 26.129 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 9883 _reflns_number_gt 8535 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'STOE X-AREA' _computing_cell_refinement 'STOE X-AREA, PLATON (A.L.Spek, 2005)' _computing_data_reduction 'STOE X-RED, PLATON (A.L.Spek, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'Diamond 3.2g' _computing_publication_material ? _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0808P)^2^+5.1675P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 9883 _refine_ls_number_parameters 614 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0464 _refine_ls_wR_factor_ref 0.1239 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.53314(2) 0.75154(2) 0.75066(2) 0.02595(9) Uani 1 1 d . . . . . Cl1A Cl 0.12346(19) 0.31605(17) 0.52118(13) 0.0284(5) Uani 0.6 1 d D . P A 1 Cl1B Cl 1.0792(4) 1.0053(3) 0.9264(3) 0.0418(9) Uani 0.4 1 d D . P B 2 Cl2 Cl 0.1709(2) 0.79262(18) 0.71456(13) 0.0633(5) Uani 1 1 d . . . . . Cl3 Cl -0.0245(3) 0.6525(3) 0.77398(19) 0.1044(11) Uani 1 1 d . . . . . Cl4 Cl 0.1517(2) 0.57220(19) 0.70026(15) 0.0700(6) Uani 1 1 d . . . . . Cl5A Cl 0.0854(3) 0.6818(3) 0.28343(19) 0.0585(7) Uiso 0.65 1 d . . P C 1 Cl5B Cl 0.1094(9) 0.6007(7) 0.2336(5) 0.093(2) Uiso 0.35 1 d . . P D 2 Cl6A Cl 0.3185(3) 0.7046(3) 0.2219(2) 0.0553(8) Uiso 0.65 1 d . . P C 1 Cl6B Cl 0.3420(5) 0.7448(5) 0.2291(3) 0.0434(12) Uiso 0.35 1 d . . P D 2 Cl7A Cl 0.0980(4) 0.7466(3) 0.1290(2) 0.0672(8) Uiso 0.65 1 d . . P C 1 Cl7B Cl 0.0955(6) 0.7937(5) 0.1672(4) 0.0634(14) Uiso 0.35 1 d . . P D 2 Cl8A Cl 1.1948(4) 1.1293(4) 0.9175(3) 0.0738(11) Uiso 0.6 1 d D . P E 1 Cl8B Cl 0.0505(6) 0.3227(5) 0.6159(3) 0.0662(13) Uiso 0.4 1 d D . P F 2 Cl9A Cl 1.1431(7) 0.9176(6) 0.8991(4) 0.123(2) Uiso 0.6 1 d D . P E 1 Cl9B Cl 0.1401(6) 0.2558(5) 0.4870(4) 0.0736(15) Uiso 0.4 1 d D . P F 2 Cl10 Cl 0.9874(9) 1.0304(8) 0.8035(5) 0.154(3) Uiso 0.6 1 d D . P E 1 Cl11 Cl 0.0517(5) 0.4432(4) 0.4858(3) 0.0646(13) Uiso 0.4 1 d D . P F 2 P1 P 0.52093(13) 0.63997(11) 0.84662(8) 0.0252(3) Uani 1 1 d . . . . . P2 P 0.53713(14) 0.86533(11) 0.65587(8) 0.0256(3) Uani 1 1 d . . . . . O1A O -0.0028(7) 0.3099(10) 0.5353(9) 0.087(4) Uani 0.6 1 d D U P A 1 O1B O 1.1936(13) 1.0731(17) 0.9112(12) 0.100(3) Uani 0.4 1 d D . P B 2 O2A O 0.2032(7) 0.4198(4) 0.5384(5) 0.048(2) Uani 0.6 1 d D . P A 1 O2B O 1.110(2) 0.9443(14) 0.9888(9) 0.100(3) Uani 0.4 1 d D . P B 2 O3A O 0.1161(13) 0.2938(9) 0.4415(3) 0.078(3) Uani 0.6 1 d D . P A 1 O3B O 1.041(2) 0.9318(12) 0.8613(7) 0.100(3) Uani 0.4 1 d D . P B 2 O4A O 0.1822(7) 0.2422(5) 0.5604(4) 0.0450(19) Uani 0.6 1 d D . P A 1 O4B O 0.9729(13) 1.0435(15) 0.9422(11) 0.100(3) Uani 0.4 1 d D . P B 2 N1 N 0.4390(6) 0.4840(4) 0.6209(3) 0.0356(11) Uani 1 1 d . . . . . H1 H 0.3592 0.4524 0.6032 0.043 Uiso 1 1 calc R U . . . N2 N 0.5263(6) 0.5261(4) 0.5784(3) 0.0385(12) Uani 1 1 d . . . . . N3 N 0.6417(6) 1.0022(5) 0.8066(3) 0.0488(15) Uani 1 1 d . . . . . N4 N 0.6876(7) 0.9873(5) 0.8794(4) 0.0525(16) Uani 1 1 d . . . . . H4 H 0.7683 0.9904 0.8965 0.063 Uiso 1 1 calc R U . . . C1 C 0.4206(5) 0.5100(5) 0.8214(3) 0.0292(11) Uani 1 1 d . . . . . C2 C 0.3416(6) 0.4639(5) 0.8711(3) 0.0362(13) Uani 1 1 d . . . . . C3 C 0.2570(7) 0.3690(6) 0.8528(4) 0.0460(16) Uani 1 1 d . . . . . C4 C 0.2513(7) 0.3160(5) 0.7852(4) 0.0448(16) Uani 1 1 d . . . . . C5 C 0.3302(6) 0.3592(5) 0.7350(4) 0.0358(13) Uani 1 1 d . . . . . C6 C 0.4144(5) 0.4561(4) 0.7515(3) 0.0272(11) Uani 1 1 d . . . . . C7 C 0.4924(6) 0.4977(4) 0.6944(3) 0.0291(12) Uani 1 1 d . . . . . C8 C 0.6193(6) 0.5491(5) 0.6994(4) 0.0361(13) Uani 1 1 d . . . . . C9 C 0.6345(7) 0.5647(5) 0.6250(4) 0.0398(15) Uani 1 1 d . . . . . C10 C 0.4548(6) 0.6893(4) 0.9222(3) 0.0314(12) Uani 1 1 d . . . . . C11 C 0.3393(8) 0.7153(7) 0.9050(4) 0.054(2) Uani 1 1 d . . . . . C12 C 0.2882(11) 0.7548(9) 0.9610(6) 0.076(3) Uani 1 1 d . . . . . C13 C 0.3527(10) 0.7713(6) 1.0337(5) 0.061(2) Uani 1 1 d . . . . . C14 C 0.4674(9) 0.7469(6) 1.0514(4) 0.054(2) Uani 1 1 d . . . . . C15 C 0.5199(7) 0.7064(5) 0.9958(4) 0.0391(14) Uani 1 1 d . . . . . C16 C 0.6750(5) 0.6242(5) 0.8912(3) 0.0285(11) Uani 1 1 d . . . . . C17 C 0.6919(6) 0.5279(5) 0.9143(4) 0.0359(13) Uani 1 1 d . . . . . C18 C 0.8088(7) 0.5195(6) 0.9527(5) 0.0476(17) Uani 1 1 d . . . . . C19 C 0.9076(7) 0.6061(7) 0.9682(5) 0.058(2) Uani 1 1 d . . . . . C20 C 0.8927(7) 0.7013(6) 0.9448(6) 0.060(2) Uani 1 1 d . . . . . C21 C 0.7760(6) 0.7106(5) 0.9063(4) 0.0439(16) Uani 1 1 d . . . . . C22 C 0.4361(5) 0.9548(4) 0.6647(3) 0.0264(11) Uani 1 1 d . . . . . C23 C 0.3530(6) 0.9706(5) 0.6003(3) 0.0298(12) Uani 1 1 d . . . . . C24 C 0.2660(6) 1.0311(5) 0.6056(4) 0.0335(13) Uani 1 1 d . . . . . C25 C 0.2612(6) 1.0748(5) 0.6756(4) 0.0373(14) Uani 1 1 d . . . . . C26 C 0.3431(6) 1.0601(5) 0.7390(4) 0.0354(13) Uani 1 1 d . . . . . C27 C 0.4323(5) 1.0007(4) 0.7347(3) 0.0297(12) Uani 1 1 d . . . . . C28 C 0.5168(6) 0.9898(4) 0.8047(3) 0.0317(12) Uani 1 1 d . . . . . C29 C 0.4837(8) 0.9689(6) 0.8757(4) 0.0529(19) Uani 1 1 d . . . . . C30 C 0.5990(9) 0.9680(6) 0.9214(4) 0.054(2) Uani 1 1 d . . . . . C31 C 0.6909(6) 0.9414(4) 0.6421(3) 0.0297(12) Uani 1 1 d . . . . . C32 C 0.7941(7) 0.8968(6) 0.6515(5) 0.0519(19) Uani 1 1 d . . . . . C33 C 0.9079(7) 0.9489(7) 0.6309(7) 0.070(3) Uani 1 1 d . . . . . C34 C 0.9191(6) 1.0463(5) 0.6032(5) 0.0447(16) Uani 1 1 d . . . . . C35 C 0.8166(6) 1.0911(5) 0.5947(4) 0.0343(13) Uani 1 1 d . . . . . C36 C 0.7026(6) 1.0390(5) 0.6136(4) 0.0337(13) Uani 1 1 d . . . . . C37 C 0.4704(5) 0.7928(4) 0.5652(3) 0.0273(11) Uani 1 1 d . . . . . C38 C 0.5331(6) 0.8045(5) 0.5039(4) 0.0358(13) Uani 1 1 d . . . . . C39 C 0.4781(7) 0.7493(5) 0.4364(4) 0.0415(15) Uani 1 1 d . . . . . C40 C 0.3600(7) 0.6816(5) 0.4289(4) 0.0404(15) Uani 1 1 d . . . . . C41 C 0.2978(7) 0.6676(6) 0.4899(4) 0.0446(15) Uani 1 1 d . . . . . C42 C 0.3524(6) 0.7227(5) 0.5580(4) 0.0385(14) Uani 1 1 d . . . . . C43 C 0.0645(7) 0.6682(8) 0.7006(5) 0.058(2) Uani 1 1 d . . . . . C44A C 0.1843(15) 0.7550(14) 0.2244(10) 0.051(4) Uiso 0.65 1 d . . P C 1 H44A H 0.2123 0.8293 0.2443 0.062 Uiso 0.65 1 calc R U P C 1 C44B C 0.181(3) 0.734(3) 0.239(2) 0.055(9) Uiso 0.35 1 d . . P D 2 H44B H 0.1785 0.7649 0.2898 0.066 Uiso 0.35 1 calc R U P D 2 C45B C 0.1334(9) 0.3651(6) 0.5421(4) 0.052(5) Uiso 0.4 1 d D . P F 2 H45B H 0.2216 0.4059 0.5635 0.062 Uiso 0.4 1 calc R U P F 2 C45A C 1.0658(6) 1.0200(4) 0.8954(6) 0.054(4) Uiso 0.6 1 d D . P E 1 H45A H 1.0069 1.0141 0.9328 0.065 Uiso 0.6 1 calc R U P E 1 H2 H 0.3466 0.4982 0.9182 0.044 Uiso 1 1 d . U . . . H3 H 0.2020 0.3394 0.8863 0.055 Uiso 1 1 d . U . . . H4A H 0.1936 0.2506 0.7725 0.055 Uiso 1 1 d . U . . . H5 H 0.3268 0.3204 0.6890 0.043 Uiso 1 1 d . U . . . H8 H 0.6816 0.5686 0.7438 0.044 Uiso 1 1 d . U . . . H9 H 0.7113 0.5986 0.6088 0.048 Uiso 1 1 d . U . . . H11 H 0.2948 0.7059 0.8540 0.066 Uiso 1 1 d . U . . . H12 H 0.2084 0.7724 0.9489 0.088 Uiso 1 1 d . U . . . H13 H 0.3182 0.7997 1.0717 0.074 Uiso 1 1 d . U . . . H14 H 0.5101 0.7575 1.1022 0.064 Uiso 1 1 d . U . . . H15 H 0.6002 0.6894 1.0081 0.046 Uiso 1 1 d . U . . . H17 H 0.6230 0.4677 0.9035 0.041 Uiso 1 1 d . U . . . H18 H 0.8209 0.4547 0.9694 0.059 Uiso 1 1 d . U . . . H19 H 0.9878 0.6011 0.9947 0.068 Uiso 1 1 d . U . . . H20 H 0.9631 0.7601 0.9554 0.072 Uiso 1 1 d . U . . . H21 H 0.7656 0.7763 0.8904 0.055 Uiso 1 1 d . U . . . H23 H 0.3564 0.9402 0.5528 0.037 Uiso 1 1 d . U . . . H24 H 0.2102 1.0418 0.5616 0.040 Uiso 1 1 d . U . . . H25 H 0.2017 1.1155 0.6796 0.046 Uiso 1 1 d . U . . . H26 H 0.3391 1.0911 0.7861 0.043 Uiso 1 1 d . U . . . H29 H 0.4018 0.9568 0.8894 0.065 Uiso 1 1 d . U . . . H30 H 0.6106 0.9559 0.9737 0.067 Uiso 1 1 d . U . . . H32 H 0.7879 0.8309 0.6721 0.061 Uiso 1 1 d . U . . . H33 H 0.9772 0.9166 0.6337 0.084 Uiso 1 1 d . U . . . H34 H 0.9984 1.0843 0.5924 0.055 Uiso 1 1 d . U . . . H35 H 0.8249 1.1579 0.5755 0.041 Uiso 1 1 d . U . . . H36 H 0.6321 1.0697 0.6068 0.041 Uiso 1 1 d . U . . . H38 H 0.6138 0.8517 0.5083 0.043 Uiso 1 1 d . U . . . H39 H 0.5221 0.7575 0.3950 0.048 Uiso 1 1 d . U . . . H40 H 0.3215 0.6442 0.3819 0.051 Uiso 1 1 d . U . . . H41 H 0.2167 0.6196 0.4857 0.053 Uiso 1 1 d . U . . . H42 H 0.3095 0.7133 0.6001 0.048 Uiso 1 1 d . U . . . H43 H 0.0063 0.6636 0.6513 0.067 Uiso 1 1 d . U . . . 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 Au1 0.03041(12) 0.02556(12) 0.02294(12) 0.00754(8) 0.00411(8) 0.00862(8) Cl1A 0.0227(10) 0.0269(11) 0.0336(11) 0.0079(10) 0.0019(8) 0.0035(8) Cl1B 0.038(2) 0.048(2) 0.041(2) 0.0057(18) -0.0037(17) 0.0207(18) Cl2 0.0575(11) 0.0691(13) 0.0696(13) 0.0210(11) 0.0177(10) 0.0214(10) Cl3 0.0622(14) 0.142(3) 0.102(2) -0.007(2) 0.0471(15) -0.0110(16) Cl4 0.0752(14) 0.0654(13) 0.0769(15) 0.0210(11) 0.0243(12) 0.0222(11) P1 0.0289(7) 0.0252(7) 0.0218(6) 0.0067(5) 0.0033(5) 0.0076(5) P2 0.0309(7) 0.0252(7) 0.0239(7) 0.0078(5) 0.0066(6) 0.0111(6) O1A 0.051(5) 0.088(7) 0.145(10) 0.050(7) 0.055(6) 0.029(5) O1B 0.119(9) 0.084(7) 0.082(7) 0.029(6) -0.011(6) 0.008(6) O2A 0.039(4) 0.028(4) 0.063(5) 0.012(4) -0.015(4) -0.007(3) O2B 0.119(9) 0.084(7) 0.082(7) 0.029(6) -0.011(6) 0.008(6) O3A 0.110(9) 0.081(7) 0.029(5) 0.007(5) -0.007(5) 0.009(6) O3B 0.119(9) 0.084(7) 0.082(7) 0.029(6) -0.011(6) 0.008(6) O4A 0.048(4) 0.033(4) 0.050(5) 0.012(3) -0.011(4) 0.014(3) O4B 0.119(9) 0.084(7) 0.082(7) 0.029(6) -0.011(6) 0.008(6) N1 0.048(3) 0.038(3) 0.027(3) 0.006(2) 0.010(2) 0.019(2) N2 0.057(3) 0.036(3) 0.029(3) 0.007(2) 0.013(2) 0.020(3) N3 0.040(3) 0.068(4) 0.040(3) 0.009(3) -0.004(3) 0.023(3) N4 0.059(4) 0.052(4) 0.044(3) 0.003(3) -0.015(3) 0.025(3) C1 0.030(3) 0.032(3) 0.025(3) 0.006(2) 0.000(2) 0.009(2) C2 0.039(3) 0.041(3) 0.026(3) 0.002(3) 0.008(2) 0.004(3) C3 0.047(4) 0.048(4) 0.038(4) 0.000(3) 0.019(3) -0.004(3) C4 0.045(4) 0.038(3) 0.046(4) -0.008(3) 0.015(3) -0.005(3) C5 0.036(3) 0.039(3) 0.033(3) -0.001(3) 0.009(3) 0.007(3) C6 0.028(3) 0.032(3) 0.023(3) 0.005(2) 0.002(2) 0.010(2) C7 0.037(3) 0.027(3) 0.028(3) 0.004(2) 0.009(2) 0.013(2) C8 0.042(3) 0.032(3) 0.038(3) 0.005(3) 0.018(3) 0.006(3) C9 0.053(4) 0.028(3) 0.041(4) 0.002(3) 0.021(3) 0.005(3) C10 0.043(3) 0.023(3) 0.029(3) 0.004(2) 0.010(3) 0.009(2) C11 0.057(4) 0.083(6) 0.038(4) 0.018(4) 0.015(3) 0.042(4) C12 0.094(7) 0.099(7) 0.070(6) 0.033(5) 0.041(6) 0.069(6) C13 0.104(7) 0.044(4) 0.055(5) 0.012(4) 0.045(5) 0.037(4) C14 0.081(6) 0.039(4) 0.038(4) -0.006(3) 0.019(4) 0.003(4) C15 0.050(4) 0.037(3) 0.027(3) 0.001(3) 0.006(3) 0.005(3) C16 0.029(3) 0.032(3) 0.024(3) 0.005(2) 0.005(2) 0.007(2) C17 0.036(3) 0.031(3) 0.041(3) 0.006(3) 0.004(3) 0.010(3) C18 0.043(4) 0.046(4) 0.060(5) 0.019(3) 0.007(3) 0.021(3) C19 0.033(3) 0.070(5) 0.072(5) 0.019(4) -0.002(3) 0.020(4) C20 0.035(4) 0.047(4) 0.087(6) 0.011(4) -0.006(4) 0.000(3) C21 0.033(3) 0.034(3) 0.060(4) 0.012(3) 0.001(3) 0.004(3) C22 0.027(3) 0.025(3) 0.028(3) 0.006(2) 0.006(2) 0.008(2) C23 0.034(3) 0.031(3) 0.028(3) 0.009(2) 0.007(2) 0.013(2) C24 0.035(3) 0.033(3) 0.036(3) 0.006(2) 0.003(2) 0.015(3) C25 0.032(3) 0.035(3) 0.048(4) 0.001(3) 0.007(3) 0.013(3) C26 0.037(3) 0.037(3) 0.035(3) -0.003(3) 0.008(3) 0.013(3) C27 0.030(3) 0.029(3) 0.030(3) 0.006(2) 0.007(2) 0.007(2) C28 0.039(3) 0.027(3) 0.029(3) 0.002(2) 0.002(2) 0.009(2) C29 0.069(5) 0.051(4) 0.037(4) 0.003(3) 0.016(4) 0.006(4) C30 0.088(6) 0.038(4) 0.028(3) -0.001(3) -0.011(4) 0.012(4) C31 0.032(3) 0.027(3) 0.031(3) 0.006(2) 0.005(2) 0.010(2) C32 0.037(3) 0.037(4) 0.086(6) 0.028(4) 0.010(4) 0.017(3) C33 0.032(4) 0.051(5) 0.133(9) 0.036(5) 0.018(4) 0.020(3) C34 0.029(3) 0.036(3) 0.067(5) 0.015(3) 0.009(3) 0.002(3) C35 0.039(3) 0.028(3) 0.036(3) 0.008(2) 0.005(3) 0.007(2) C36 0.033(3) 0.031(3) 0.039(3) 0.009(3) 0.006(3) 0.013(2) C37 0.034(3) 0.025(3) 0.027(3) 0.007(2) 0.005(2) 0.015(2) C38 0.045(3) 0.031(3) 0.034(3) 0.006(2) 0.013(3) 0.011(3) C39 0.059(4) 0.037(3) 0.035(3) 0.002(3) 0.016(3) 0.018(3) C40 0.056(4) 0.034(3) 0.033(3) 0.001(3) -0.001(3) 0.022(3) C41 0.044(4) 0.041(4) 0.045(4) 0.001(3) 0.000(3) 0.009(3) C42 0.033(3) 0.047(4) 0.036(3) 0.007(3) 0.009(3) 0.010(3) C43 0.041(4) 0.085(6) 0.047(4) 0.011(4) 0.002(3) 0.016(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 P1 2.3023(14) . ? Au1 P2 2.3049(14) . ? Cl1A O1A 1.433(5) . ? Cl1A O4A 1.432(4) . ? Cl1A O3A 1.443(5) . ? Cl1A O2A 1.443(4) . ? Cl1B O1B 1.434(5) . ? Cl1B O4B 1.439(5) . ? Cl1B O2B 1.442(5) . ? Cl1B O3B 1.448(5) . ? Cl2 C43 1.770(10) . ? Cl3 C43 1.755(9) . ? Cl4 C43 1.763(9) . ? Cl5A C44A 1.784(18) . ? Cl5B C44B 1.75(3) . ? Cl6A C44A 1.760(17) . ? Cl6B C44B 1.77(3) . ? Cl7A C44A 1.807(17) . ? Cl7B C44B 1.79(3) . ? Cl8A C45A 1.758(2) . ? Cl8B C45B 1.760(2) . ? Cl9A C45A 1.758(2) . ? Cl9B C45B 1.760(2) . ? Cl10 C45A 1.760(2) . ? Cl11 C45B 1.760(2) . ? Cl11 Cl11 2.183(11) 2_566 ? P1 C16 1.810(6) . ? P1 C1 1.817(6) . ? P1 C10 1.818(6) . ? P2 C31 1.810(6) . ? P2 C22 1.824(5) . ? P2 C37 1.825(6) . ? O2B O4B 1.68(3) 2_777 ? O4B O2B 1.68(3) 2_777 ? N1 C7 1.347(8) . ? N1 N2 1.350(8) . ? N1 H1 0.8800 . ? N2 C9 1.321(10) . ? N3 C28 1.336(8) . ? N3 N4 1.362(8) . ? N4 C30 1.309(12) . ? N4 H4 0.8800 . ? C1 C2 1.399(8) . ? C1 C6 1.415(8) . ? C2 C3 1.375(10) . ? C2 H2 0.941(6) . ? C3 C4 1.375(10) . ? C3 H3 0.950(6) . ? C4 C5 1.394(9) . ? C4 H4A 0.944(7) . ? C5 C6 1.389(9) . ? C5 H5 0.955(6) . ? C6 C7 1.479(8) . ? C7 C8 1.386(9) . ? C8 C9 1.393(9) . ? C8 H8 0.949(7) . ? C9 H9 0.952(6) . ? C10 C11 1.378(10) . ? C10 C15 1.386(9) . ? C11 C12 1.380(12) . ? C11 H11 0.957(8) . ? C12 C13 1.368(15) . ? C12 H12 0.951(9) . ? C13 C14 1.361(13) . ? C13 H13 0.944(7) . ? C14 C15 1.388(10) . ? C14 H14 0.948(8) . ? C15 H15 0.953(7) . ? C16 C21 1.382(9) . ? C16 C17 1.395(8) . ? C17 C18 1.385(9) . ? C17 H17 0.954(6) . ? C18 C19 1.370(12) . ? C18 H18 0.948(7) . ? C19 C20 1.379(12) . ? C19 H19 0.948(7) . ? C20 C21 1.387(10) . ? C20 H20 0.950(7) . ? C21 H21 0.950(7) . ? C22 C27 1.398(8) . ? C22 C23 1.405(8) . ? C23 C24 1.395(8) . ? C23 H23 0.947(6) . ? C24 C25 1.388(9) . ? C24 H24 0.953(6) . ? C25 C26 1.381(9) . ? C25 H25 0.950(6) . ? C26 C27 1.402(8) . ? C26 H26 0.946(6) . ? C27 C28 1.470(8) . ? C28 C29 1.401(10) . ? C29 C30 1.395(12) . ? C29 H29 0.949(8) . ? C30 H30 0.952(7) . ? C31 C32 1.384(9) . ? C31 C36 1.391(8) . ? C32 C33 1.390(11) . ? C32 H32 0.950(7) . ? C33 C34 1.383(11) . ? C33 H33 0.952(7) . ? C34 C35 1.379(9) . ? C34 H34 0.950(6) . ? C35 C36 1.379(9) . ? C35 H35 0.949(6) . ? C36 H36 0.947(6) . ? C37 C38 1.387(8) . ? C37 C42 1.389(9) . ? C38 C39 1.374(10) . ? C38 H38 0.947(7) . ? C39 C40 1.377(11) . ? C39 H39 0.947(7) . ? C40 C41 1.377(10) . ? C40 H40 0.952(7) . ? C41 C42 1.382(10) . ? C41 H41 0.956(7) . ? C42 H42 0.952(6) . ? C43 H43 0.998(8) . ? C44A H44A 1.0000 . ? C44B H44B 1.0000 . ? C45B H45B 1.0000 . ? C45A H45A 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 P1 Au1 P2 177.36(5) . . ? O1A Cl1A O4A 112.9(6) . . ? O1A Cl1A O3A 108.2(8) . . ? O4A Cl1A O3A 107.4(6) . . ? O1A Cl1A O2A 111.5(7) . . ? O4A Cl1A O2A 110.5(5) . . ? O3A Cl1A O2A 106.1(6) . . ? O1B Cl1B O4B 122.3(14) . . ? O1B Cl1B O2B 109.5(13) . . ? O4B Cl1B O2B 105.6(13) . . ? O1B Cl1B O3B 103.1(14) . . ? O4B Cl1B O3B 110.6(14) . . ? O2B Cl1B O3B 104.6(12) . . ? C45B Cl11 Cl11 131.8(5) . 2_566 ? C16 P1 C1 106.5(3) . . ? C16 P1 C10 105.0(3) . . ? C1 P1 C10 104.3(3) . . ? C16 P1 Au1 113.01(19) . . ? C1 P1 Au1 116.02(19) . . ? C10 P1 Au1 111.04(19) . . ? C31 P2 C22 107.7(3) . . ? C31 P2 C37 104.0(3) . . ? C22 P2 C37 105.0(3) . . ? C31 P2 Au1 117.64(19) . . ? C22 P2 Au1 112.18(18) . . ? C37 P2 Au1 109.39(18) . . ? Cl1B O2B O4B 111.5(16) . 2_777 ? Cl1B O4B O2B 142.1(14) . 2_777 ? C7 N1 N2 109.8(5) . . ? C7 N1 H1 125.1 . . ? N2 N1 H1 125.1 . . ? C9 N2 N1 107.2(5) . . ? C28 N3 N4 104.1(6) . . ? C30 N4 N3 113.0(6) . . ? C30 N4 H4 123.5 . . ? N3 N4 H4 123.5 . . ? C2 C1 C6 118.8(5) . . ? C2 C1 P1 118.7(5) . . ? C6 C1 P1 122.4(4) . . ? C3 C2 C1 121.4(6) . . ? C3 C2 H2 119.0(6) . . ? C1 C2 H2 119.5(6) . . ? C2 C3 C4 119.9(6) . . ? C2 C3 H3 120.7(7) . . ? C4 C3 H3 119.4(7) . . ? C3 C4 C5 119.9(6) . . ? C3 C4 H4A 120.2(7) . . ? C5 C4 H4A 119.9(7) . . ? C6 C5 C4 121.2(6) . . ? C6 C5 H5 120.1(6) . . ? C4 C5 H5 118.8(6) . . ? C5 C6 C1 118.7(5) . . ? C5 C6 C7 117.8(5) . . ? C1 C6 C7 123.5(5) . . ? N1 C7 C8 107.9(5) . . ? N1 C7 C6 119.2(5) . . ? C8 C7 C6 132.8(6) . . ? C7 C8 C9 104.4(6) . . ? C7 C8 H8 127.5(6) . . ? C9 C8 H8 128.0(6) . . ? N2 C9 C8 110.7(6) . . ? N2 C9 H9 123.6(7) . . ? C8 C9 H9 125.7(7) . . ? C11 C10 C15 119.0(6) . . ? C11 C10 P1 119.0(5) . . ? C15 C10 P1 122.0(5) . . ? C10 C11 C12 120.1(8) . . ? C10 C11 H11 119.7(7) . . ? C12 C11 H11 120.2(8) . . ? C13 C12 C11 120.6(8) . . ? C13 C12 H12 119.6(9) . . ? C11 C12 H12 119.7(10) . . ? C14 C13 C12 119.9(7) . . ? C14 C13 H13 119.7(10) . . ? C12 C13 H13 120.3(10) . . ? C13 C14 C15 120.2(7) . . ? C13 C14 H14 118.9(8) . . ? C15 C14 H14 120.9(9) . . ? C10 C15 C14 120.1(7) . . ? C10 C15 H15 119.6(6) . . ? C14 C15 H15 120.4(7) . . ? C21 C16 C17 119.5(6) . . ? C21 C16 P1 119.0(5) . . ? C17 C16 P1 121.4(5) . . ? C18 C17 C16 120.2(6) . . ? C18 C17 H17 119.7(6) . . ? C16 C17 H17 120.1(6) . . ? C19 C18 C17 119.6(6) . . ? C19 C18 H18 119.5(7) . . ? C17 C18 H18 120.9(7) . . ? C18 C19 C20 120.8(7) . . ? C18 C19 H19 120.2(8) . . ? C20 C19 H19 119.0(8) . . ? C19 C20 C21 120.0(7) . . ? C19 C20 H20 119.3(8) . . ? C21 C20 H20 120.8(8) . . ? C16 C21 C20 119.9(6) . . ? C16 C21 H21 120.1(6) . . ? C20 C21 H21 120.0(7) . . ? C27 C22 C23 119.7(5) . . ? C27 C22 P2 121.4(4) . . ? C23 C22 P2 118.7(4) . . ? C24 C23 C22 120.7(5) . . ? C24 C23 H23 119.7(6) . . ? C22 C23 H23 119.6(5) . . ? C25 C24 C23 119.2(6) . . ? C25 C24 H24 120.5(6) . . ? C23 C24 H24 120.3(6) . . ? C26 C25 C24 120.4(5) . . ? C26 C25 H25 120.0(6) . . ? C24 C25 H25 119.6(6) . . ? C25 C26 C27 121.3(6) . . ? C25 C26 H26 119.2(6) . . ? C27 C26 H26 119.5(6) . . ? C22 C27 C26 118.7(5) . . ? C22 C27 C28 123.5(5) . . ? C26 C27 C28 117.9(5) . . ? N3 C28 C29 111.5(6) . . ? N3 C28 C27 120.9(5) . . ? C29 C28 C27 127.6(6) . . ? C30 C29 C28 103.9(7) . . ? C30 C29 H29 127.9(8) . . ? C28 C29 H29 128.3(8) . . ? N4 C30 C29 107.5(6) . . ? N4 C30 H30 126.6(9) . . ? C29 C30 H30 125.9(10) . . ? C32 C31 C36 119.7(6) . . ? C32 C31 P2 119.4(5) . . ? C36 C31 P2 120.5(4) . . ? C31 C32 C33 119.8(6) . . ? C31 C32 H32 120.5(7) . . ? C33 C32 H32 119.7(7) . . ? C34 C33 C32 120.1(6) . . ? C34 C33 H33 119.6(8) . . ? C32 C33 H33 120.2(8) . . ? C35 C34 C33 119.9(6) . . ? C35 C34 H34 119.6(7) . . ? C33 C34 H34 120.4(7) . . ? C34 C35 C36 120.3(6) . . ? C34 C35 H35 119.4(6) . . ? C36 C35 H35 120.2(6) . . ? C35 C36 C31 120.1(5) . . ? C35 C36 H36 119.8(6) . . ? C31 C36 H36 120.1(6) . . ? C38 C37 C42 119.1(6) . . ? C38 C37 P2 122.5(5) . . ? C42 C37 P2 118.4(4) . . ? C39 C38 C37 120.4(6) . . ? C39 C38 H38 119.8(6) . . ? C37 C38 H38 119.8(6) . . ? C38 C39 C40 120.3(6) . . ? C38 C39 H39 119.7(7) . . ? C40 C39 H39 120.0(7) . . ? C39 C40 C41 119.8(6) . . ? C39 C40 H40 120.2(7) . . ? C41 C40 H40 120.0(7) . . ? C40 C41 C42 120.3(7) . . ? C40 C41 H41 120.6(7) . . ? C42 C41 H41 119.2(7) . . ? C41 C42 C37 120.0(6) . . ? C41 C42 H42 120.4(7) . . ? C37 C42 H42 119.6(6) . . ? Cl3 C43 Cl4 110.6(5) . . ? Cl3 C43 Cl2 108.4(5) . . ? Cl4 C43 Cl2 109.5(4) . . ? Cl3 C43 H43 109.6(6) . . ? Cl4 C43 H43 109.7(7) . . ? Cl2 C43 H43 109.0(7) . . ? Cl6A C44A Cl5A 110.1(10) . . ? Cl6A C44A Cl7A 107.8(9) . . ? Cl5A C44A Cl7A 110.2(9) . . ? Cl6A C44A H44A 109.6 . . ? Cl5A C44A H44A 109.6 . . ? Cl7A C44A H44A 109.6 . . ? Cl5B C44B Cl6B 106.5(17) . . ? Cl5B C44B Cl7B 108.9(17) . . ? Cl6B C44B Cl7B 113.1(19) . . ? Cl5B C44B H44B 109.4 . . ? Cl6B C44B H44B 109.4 . . ? Cl7B C44B H44B 109.4 . . ? Cl8B C45B Cl9B 108.8(5) . . ? Cl8B C45B Cl11 109.1(5) . . ? Cl9B C45B Cl11 109.4(5) . . ? Cl8B C45B H45B 109.8 . . ? Cl9B C45B H45B 109.8 . . ? Cl11 C45B H45B 109.8 . . ? Cl8A C45A Cl9A 102.0(5) . . ? Cl8A C45A Cl10 107.6(6) . . ? Cl9A C45A Cl10 111.7(7) . . ? Cl8A C45A H45A 111.7 . . ? Cl9A C45A H45A 111.7 . . ? Cl10 C45A H45A 111.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1B Cl1B O2B O4B 125.3(18) . . . 2_777 ? O4B Cl1B O2B O4B -8(2) . . . 2_777 ? O3B Cl1B O2B O4B -124.9(17) . . . 2_777 ? O1B Cl1B O4B O2B -114(3) . . . 2_777 ? O2B Cl1B O4B O2B 12(3) . . . 2_777 ? O3B Cl1B O4B O2B 125(3) . . . 2_777 ? C7 N1 N2 C9 0.8(7) . . . . ? C28 N3 N4 C30 -0.6(8) . . . . ? C16 P1 C1 C2 95.1(5) . . . . ? C10 P1 C1 C2 -15.6(5) . . . . ? Au1 P1 C1 C2 -138.1(4) . . . . ? C16 P1 C1 C6 -88.4(5) . . . . ? C10 P1 C1 C6 160.8(5) . . . . ? Au1 P1 C1 C6 38.3(5) . . . . ? C6 C1 C2 C3 -1.3(10) . . . . ? P1 C1 C2 C3 175.3(6) . . . . ? C1 C2 C3 C4 1.7(12) . . . . ? C2 C3 C4 C5 -0.7(12) . . . . ? C3 C4 C5 C6 -0.7(11) . . . . ? C4 C5 C6 C1 1.1(9) . . . . ? C4 C5 C6 C7 -178.4(6) . . . . ? C2 C1 C6 C5 -0.2(8) . . . . ? P1 C1 C6 C5 -176.6(5) . . . . ? C2 C1 C6 C7 179.4(6) . . . . ? P1 C1 C6 C7 2.9(8) . . . . ? N2 N1 C7 C8 -0.9(7) . . . . ? N2 N1 C7 C6 -179.1(5) . . . . ? C5 C6 C7 N1 39.9(8) . . . . ? C1 C6 C7 N1 -139.6(6) . . . . ? C5 C6 C7 C8 -137.7(7) . . . . ? C1 C6 C7 C8 42.8(10) . . . . ? N1 C7 C8 C9 0.6(7) . . . . ? C6 C7 C8 C9 178.4(6) . . . . ? N1 N2 C9 C8 -0.5(7) . . . . ? C7 C8 C9 N2 -0.1(7) . . . . ? C16 P1 C10 C11 176.3(6) . . . . ? C1 P1 C10 C11 -71.9(6) . . . . ? Au1 P1 C10 C11 53.8(6) . . . . ? C16 P1 C10 C15 -0.5(6) . . . . ? C1 P1 C10 C15 111.4(5) . . . . ? Au1 P1 C10 C15 -122.9(5) . . . . ? C15 C10 C11 C12 -1.8(13) . . . . ? P1 C10 C11 C12 -178.7(8) . . . . ? C10 C11 C12 C13 1.7(16) . . . . ? C11 C12 C13 C14 -1.1(16) . . . . ? C12 C13 C14 C15 0.6(13) . . . . ? C11 C10 C15 C14 1.4(10) . . . . ? P1 C10 C15 C14 178.2(5) . . . . ? C13 C14 C15 C10 -0.8(11) . . . . ? C1 P1 C16 C21 170.5(5) . . . . ? C10 P1 C16 C21 -79.2(6) . . . . ? Au1 P1 C16 C21 42.0(6) . . . . ? C1 P1 C16 C17 -13.0(6) . . . . ? C10 P1 C16 C17 97.3(5) . . . . ? Au1 P1 C16 C17 -141.5(5) . . . . ? C21 C16 C17 C18 0.7(10) . . . . ? P1 C16 C17 C18 -175.7(5) . . . . ? C16 C17 C18 C19 0.2(12) . . . . ? C17 C18 C19 C20 -1.1(14) . . . . ? C18 C19 C20 C21 1.1(15) . . . . ? C17 C16 C21 C20 -0.7(11) . . . . ? P1 C16 C21 C20 175.8(7) . . . . ? C19 C20 C21 C16 -0.2(14) . . . . ? C31 P2 C22 C27 -89.3(5) . . . . ? C37 P2 C22 C27 160.4(5) . . . . ? Au1 P2 C22 C27 41.7(5) . . . . ? C31 P2 C22 C23 96.1(5) . . . . ? C37 P2 C22 C23 -14.3(5) . . . . ? Au1 P2 C22 C23 -133.0(4) . . . . ? C27 C22 C23 C24 -0.4(9) . . . . ? P2 C22 C23 C24 174.3(5) . . . . ? C22 C23 C24 C25 -0.7(9) . . . . ? C23 C24 C25 C26 1.1(10) . . . . ? C24 C25 C26 C27 -0.3(10) . . . . ? C23 C22 C27 C26 1.2(8) . . . . ? P2 C22 C27 C26 -173.4(5) . . . . ? C23 C22 C27 C28 -179.0(6) . . . . ? P2 C22 C27 C28 6.4(8) . . . . ? C25 C26 C27 C22 -0.9(9) . . . . ? C25 C26 C27 C28 179.3(6) . . . . ? N4 N3 C28 C29 0.9(8) . . . . ? N4 N3 C28 C27 179.5(6) . . . . ? C22 C27 C28 N3 46.2(9) . . . . ? C26 C27 C28 N3 -134.0(6) . . . . ? C22 C27 C28 C29 -135.4(7) . . . . ? C26 C27 C28 C29 44.4(9) . . . . ? N3 C28 C29 C30 -0.8(8) . . . . ? C27 C28 C29 C30 -179.4(6) . . . . ? N3 N4 C30 C29 0.1(9) . . . . ? C28 C29 C30 N4 0.4(8) . . . . ? C22 P2 C31 C32 164.8(6) . . . . ? C37 P2 C31 C32 -84.2(6) . . . . ? Au1 P2 C31 C32 36.9(7) . . . . ? C22 P2 C31 C36 -23.0(6) . . . . ? C37 P2 C31 C36 88.1(5) . . . . ? Au1 P2 C31 C36 -150.9(4) . . . . ? C36 C31 C32 C33 -1.4(13) . . . . ? P2 C31 C32 C33 170.9(8) . . . . ? C31 C32 C33 C34 2.0(16) . . . . ? C32 C33 C34 C35 -1.2(15) . . . . ? C33 C34 C35 C36 -0.2(12) . . . . ? C34 C35 C36 C31 0.8(10) . . . . ? C32 C31 C36 C35 0.0(10) . . . . ? P2 C31 C36 C35 -172.2(5) . . . . ? C31 P2 C37 C38 -2.0(5) . . . . ? C22 P2 C37 C38 111.0(5) . . . . ? Au1 P2 C37 C38 -128.4(4) . . . . ? C31 P2 C37 C42 177.6(5) . . . . ? C22 P2 C37 C42 -69.4(5) . . . . ? Au1 P2 C37 C42 51.1(5) . . . . ? C42 C37 C38 C39 1.5(9) . . . . ? P2 C37 C38 C39 -179.0(5) . . . . ? C37 C38 C39 C40 -0.1(10) . . . . ? C38 C39 C40 C41 -1.3(10) . . . . ? C39 C40 C41 C42 1.2(10) . . . . ? C40 C41 C42 C37 0.2(10) . . . . ? C38 C37 C42 C41 -1.5(9) . . . . ? P2 C37 C42 C41 178.9(5) . . . . ? Cl11 Cl11 C45B Cl8B 37.3(10) 2_566 . . . ? Cl11 Cl11 C45B Cl9B 156.2(6) 2_566 . . . ? _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.759 _refine_diff_density_min -1.627 _refine_diff_density_rms 0.176 _database_code_depnum_ccdc_archive 'CCDC 960840'