# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jason Lynam' _publ_contact_author_email JML12@YORK.AC.UK loop_ _publ_author_name J.Lynam L.D.Dingwall T.D.Nixon A.C.Whitwood # Attachment '3thf2.cif' data_jml0724a _database_code_depnum_ccdc_archive 'CCDC 710808' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 Au Cl N2 O2 P, 2(C4 H8 O)' _chemical_formula_sum 'C24 H29 Au Cl N2 O4 P' _chemical_formula_weight 672.88 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' P P 0.1023 0.0942 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 32.515(4) _cell_length_b 11.4439(13) _cell_length_c 13.4243(15) _cell_angle_alpha 90.00 _cell_angle_beta 91.298(3) _cell_angle_gamma 90.00 _cell_volume 4993.9(10) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5018 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 28.26 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2640 _exptl_absorpt_coefficient_mu 6.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.499 _exptl_absorpt_correction_T_max 0.833 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24075 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0336 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.30 _reflns_number_total 6188 _reflns_number_gt 5279 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. THF were poorly defined due to multiple positions whihc could not be resolved. This led to large ADP for all heavy atoms of both THF molecules and the need to restrain the bond lengths (C-C 1.54 A, C-O 1.44 A) and to restrain ther ADP to be approximately isotropic (ISOR 0.05). ; _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^)+(0.0426P)^2^+32.3220P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6188 _refine_ls_number_parameters 306 _refine_ls_number_restraints 70 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0333 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0806 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.326055(5) 0.653285(15) 0.037614(11) 0.01777(6) Uani 1 1 d . . . C1 C 0.37140(14) 0.4930(4) 0.2101(3) 0.0200(9) Uani 1 1 d . . . C2 C 0.40972(15) 0.5010(5) 0.1577(3) 0.0242(10) Uani 1 1 d . . . C3 C 0.44598(15) 0.5265(6) 0.3182(3) 0.0325(13) Uani 1 1 d . . . C4 C 0.37278(15) 0.5014(5) 0.3112(3) 0.0234(10) Uani 1 1 d . . . H4 H 0.3479 0.4964 0.3466 0.028 Uiso 1 1 calc R . . C5 C 0.32621(14) 0.3573(4) 0.0611(3) 0.0196(9) Uani 1 1 d . . . C6 C 0.35143(18) 0.2639(5) 0.0877(4) 0.0326(12) Uani 1 1 d . . . H6 H 0.3698 0.2701 0.1436 0.039 Uiso 1 1 calc R . . C7 C 0.3497(2) 0.1619(5) 0.0327(5) 0.0421(15) Uani 1 1 d . . . H7 H 0.3670 0.0980 0.0507 0.050 Uiso 1 1 calc R . . C8 C 0.3227(2) 0.1523(5) -0.0489(4) 0.0416(15) Uani 1 1 d . . . H8 H 0.3214 0.0818 -0.0863 0.050 Uiso 1 1 calc R . . C9 C 0.29799(19) 0.2448(5) -0.0752(4) 0.0353(13) Uani 1 1 d . . . H9 H 0.2796 0.2379 -0.1309 0.042 Uiso 1 1 calc R . . C10 C 0.29962(16) 0.3486(4) -0.0213(4) 0.0254(10) Uani 1 1 d . . . H10 H 0.2827 0.4129 -0.0405 0.030 Uiso 1 1 calc R . . C11 C 0.28311(13) 0.4794(4) 0.2152(3) 0.0177(9) Uani 1 1 d . . . C12 C 0.28112(15) 0.3875(4) 0.2830(3) 0.0210(9) Uani 1 1 d . . . H12 H 0.3024 0.3307 0.2860 0.025 Uiso 1 1 calc R . . C13 C 0.24809(15) 0.3789(4) 0.3462(3) 0.0217(9) Uani 1 1 d . . . H13 H 0.2472 0.3172 0.3935 0.026 Uiso 1 1 calc R . . C14 C 0.21653(15) 0.4597(5) 0.3405(4) 0.0275(10) Uani 1 1 d . . . H14 H 0.1938 0.4532 0.3834 0.033 Uiso 1 1 calc R . . C15 C 0.21809(17) 0.5498(5) 0.2725(4) 0.0384(14) Uani 1 1 d . . . H15 H 0.1963 0.6049 0.2682 0.046 Uiso 1 1 calc R . . C16 C 0.25161(16) 0.5603(5) 0.2101(4) 0.0301(11) Uani 1 1 d . . . H16 H 0.2528 0.6232 0.1640 0.036 Uiso 1 1 calc R . . Cl1 Cl 0.33137(4) 0.81969(11) -0.05610(9) 0.0284(3) Uani 1 1 d . . . N1 N 0.44488(13) 0.5187(5) 0.2162(3) 0.0341(12) Uani 1 1 d . . . H1 H 0.469(2) 0.542(6) 0.195(5) 0.05(2) Uiso 1 1 d . . . N2 N 0.40862(13) 0.5166(4) 0.3625(3) 0.0282(10) Uani 1 1 d . . . H2 H 0.4082(17) 0.510(5) 0.426(4) 0.026(14) Uiso 1 1 d . . . O1 O 0.41254(11) 0.4962(4) 0.0665(2) 0.0306(9) Uani 1 1 d . . . O2 O 0.47790(11) 0.5424(5) 0.3661(2) 0.0485(13) Uani 1 1 d . . . P1 P 0.32584(3) 0.49259(10) 0.13184(8) 0.0167(2) Uani 1 1 d . . . C17 C 0.1030(5) 0.4532(11) 0.3161(12) 0.144(6) Uani 1 1 d DU . . H17A H 0.1302 0.4807 0.3412 0.173 Uiso 1 1 calc R . . H17B H 0.0847 0.4498 0.3740 0.173 Uiso 1 1 calc R . . C18 C 0.0859(8) 0.5453(14) 0.2441(16) 0.313(16) Uani 1 1 d DU . . H18A H 0.1073 0.5927 0.2121 0.375 Uiso 1 1 calc R . . H18B H 0.0646 0.5960 0.2733 0.375 Uiso 1 1 calc R . . C19 C 0.0681(7) 0.4480(15) 0.1767(15) 0.232(12) Uani 1 1 d DU . . H19A H 0.0807 0.4556 0.1106 0.279 Uiso 1 1 calc R . . H19B H 0.0383 0.4626 0.1672 0.279 Uiso 1 1 calc R . . C20 C 0.0736(5) 0.3204(15) 0.2111(12) 0.204(11) Uani 1 1 d DU . . H20A H 0.0490 0.2907 0.2450 0.245 Uiso 1 1 calc R . . H20B H 0.0804 0.2679 0.1552 0.245 Uiso 1 1 calc R . . O3 O 0.1080(4) 0.3357(10) 0.2795(10) 0.175(5) Uani 1 1 d DU . . C21 C 0.5005(7) 0.234(5) 0.3465(19) 0.47(3) Uani 1 1 d DU . . H21A H 0.5148 0.2911 0.3039 0.569 Uiso 1 1 calc R . . H21B H 0.5023 0.1564 0.3144 0.569 Uiso 1 1 calc R . . C22 C 0.5224(5) 0.229(2) 0.4490(16) 0.220(11) Uani 1 1 d DU . . H22A H 0.5318 0.3075 0.4716 0.263 Uiso 1 1 calc R . . H22B H 0.5459 0.1744 0.4499 0.263 Uiso 1 1 calc R . . C23 C 0.4863(5) 0.1836(17) 0.5104(16) 0.229(11) Uani 1 1 d DU . . H23A H 0.4846 0.0973 0.5085 0.274 Uiso 1 1 calc R . . H23B H 0.4884 0.2100 0.5805 0.274 Uiso 1 1 calc R . . C24 C 0.4495(6) 0.2401(18) 0.4552(11) 0.198(9) Uani 1 1 d DU . . H24A H 0.4256 0.1864 0.4574 0.237 Uiso 1 1 calc R . . H24B H 0.4419 0.3130 0.4901 0.237 Uiso 1 1 calc R . . O4 O 0.4579(8) 0.2669(16) 0.3527(12) 0.335(13) Uani 1 1 d DU . . 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 0.02270(10) 0.01887(10) 0.01175(9) 0.00105(6) 0.00066(6) -0.00185(7) C1 0.019(2) 0.032(3) 0.0092(18) 0.0028(17) 0.0001(15) -0.0011(18) C2 0.023(2) 0.039(3) 0.0104(19) 0.0031(18) -0.0022(16) -0.001(2) C3 0.022(2) 0.065(4) 0.011(2) 0.000(2) -0.0002(17) 0.004(2) C4 0.021(2) 0.036(3) 0.013(2) 0.0020(18) 0.0021(16) 0.001(2) C5 0.026(2) 0.020(2) 0.0132(19) 0.0020(16) 0.0047(17) -0.0035(18) C6 0.044(3) 0.033(3) 0.020(2) 0.003(2) -0.002(2) 0.010(2) C7 0.062(4) 0.026(3) 0.038(3) 0.002(2) 0.007(3) 0.010(3) C8 0.066(4) 0.029(3) 0.030(3) -0.009(2) 0.009(3) -0.003(3) C9 0.051(3) 0.033(3) 0.021(2) -0.006(2) -0.001(2) -0.016(3) C10 0.032(3) 0.025(3) 0.019(2) 0.0021(18) -0.0029(19) -0.005(2) C11 0.019(2) 0.021(2) 0.0129(18) 0.0000(16) -0.0020(15) -0.0032(17) C12 0.026(2) 0.017(2) 0.019(2) -0.0039(17) -0.0006(18) 0.0005(18) C13 0.028(2) 0.020(2) 0.018(2) 0.0026(17) 0.0023(18) -0.0050(18) C14 0.023(2) 0.031(3) 0.029(2) 0.006(2) 0.0076(19) -0.002(2) C15 0.029(3) 0.043(3) 0.044(3) 0.020(3) 0.012(2) 0.014(3) C16 0.029(3) 0.029(3) 0.032(3) 0.013(2) 0.008(2) 0.009(2) Cl1 0.0449(7) 0.0200(6) 0.0205(5) 0.0040(4) 0.0018(5) -0.0039(5) N1 0.018(2) 0.077(4) 0.0082(17) 0.0010(19) 0.0005(15) -0.004(2) N2 0.023(2) 0.054(3) 0.0074(17) 0.0004(17) -0.0002(15) 0.0001(19) O1 0.0252(18) 0.059(3) 0.0070(14) 0.0010(15) 0.0009(12) -0.0021(17) O2 0.0225(19) 0.111(4) 0.0121(16) -0.003(2) -0.0029(14) -0.001(2) P1 0.0192(5) 0.0208(6) 0.0102(4) 0.0011(4) 0.0002(4) -0.0005(4) C17 0.176(15) 0.111(11) 0.142(13) -0.014(10) -0.076(11) -0.008(10) C18 0.28(3) 0.46(4) 0.20(2) 0.01(3) -0.09(2) -0.17(3) C19 0.20(2) 0.22(2) 0.27(2) -0.14(2) -0.072(18) 0.006(17) C20 0.173(16) 0.210(18) 0.23(2) -0.151(16) 0.066(14) -0.119(15) O3 0.202(13) 0.128(9) 0.190(12) 0.008(8) -0.086(10) -0.013(8) C21 0.52(5) 0.42(4) 0.49(5) -0.16(4) 0.06(4) 0.03(4) C22 0.112(12) 0.26(2) 0.29(2) -0.15(2) 0.094(15) -0.077(14) C23 0.146(17) 0.124(14) 0.42(3) -0.046(19) 0.01(2) 0.017(13) C24 0.23(2) 0.169(18) 0.202(19) -0.039(15) 0.111(17) 0.020(16) O4 0.56(3) 0.193(15) 0.260(17) -0.004(13) 0.29(2) 0.091(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 P1 2.2321(11) . ? Au1 Cl1 2.2910(12) . ? C1 C4 1.360(6) . ? C1 C2 1.447(6) . ? C1 P1 1.796(4) . ? C2 O1 1.232(5) . ? C2 N1 1.387(6) . ? C3 O2 1.222(6) . ? C3 N2 1.369(6) . ? C3 N1 1.371(6) . ? C4 N2 1.351(6) . ? C4 H4 0.9500 . ? C5 C6 1.389(7) . ? C5 C10 1.392(6) . ? C5 P1 1.817(5) . ? C6 C7 1.381(8) . ? C6 H6 0.9500 . ? C7 C8 1.393(9) . ? C7 H7 0.9500 . ? C8 C9 1.370(9) . ? C8 H8 0.9500 . ? C9 C10 1.392(7) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.381(7) . ? C11 C12 1.394(6) . ? C11 P1 1.810(5) . ? C12 C13 1.387(7) . ? C12 H12 0.9500 . ? C13 C14 1.383(7) . ? C13 H13 0.9500 . ? C14 C15 1.379(7) . ? C14 H14 0.9500 . ? C15 C16 1.395(7) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N1 H1 0.87(7) . ? N2 H2 0.85(6) . ? C17 O3 1.442(18) . ? C17 C18 1.53(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.54(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.54(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 O3 1.44(2) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 O4 1.44(4) . ? C21 C22 1.54(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.54(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.54(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 O4 1.44(2) . ? C24 H24A 0.9900 . ? C24 H24B 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 175.74(5) . . ? C4 C1 C2 118.1(4) . . ? C4 C1 P1 126.3(4) . . ? C2 C1 P1 115.1(3) . . ? O1 C2 N1 119.4(4) . . ? O1 C2 C1 124.4(4) . . ? N1 C2 C1 116.2(4) . . ? O2 C3 N2 122.4(4) . . ? O2 C3 N1 122.5(5) . . ? N2 C3 N1 115.1(4) . . ? N2 C4 C1 121.7(4) . . ? N2 C4 H4 119.1 . . ? C1 C4 H4 119.1 . . ? C6 C5 C10 120.2(5) . . ? C6 C5 P1 122.1(4) . . ? C10 C5 P1 117.7(4) . . ? C7 C6 C5 119.7(5) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C6 C7 C8 120.3(6) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 119.8(5) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 120.7(5) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C5 C10 C9 119.3(5) . . ? C5 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C16 C11 C12 119.5(4) . . ? C16 C11 P1 119.5(3) . . ? C12 C11 P1 121.0(4) . . ? C13 C12 C11 120.1(4) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 120.2(4) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 119.9(5) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.2(5) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C11 C16 C15 120.1(5) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C3 N1 C2 125.3(4) . . ? C3 N1 H1 108(5) . . ? C2 N1 H1 126(5) . . ? C4 N2 C3 123.6(4) . . ? C4 N2 H2 118(4) . . ? C3 N2 H2 118(4) . . ? C1 P1 C11 105.87(19) . . ? C1 P1 C5 107.0(2) . . ? C11 P1 C5 105.4(2) . . ? C1 P1 Au1 108.41(16) . . ? C11 P1 Au1 115.56(15) . . ? C5 P1 Au1 113.94(15) . . ? O3 C17 C18 118.0(13) . . ? O3 C17 H17A 107.8 . . ? C18 C17 H17A 107.8 . . ? O3 C17 H17B 107.8 . . ? C18 C17 H17B 107.8 . . ? H17A C17 H17B 107.1 . . ? C17 C18 C19 89.9(12) . . ? C17 C18 H18A 113.7 . . ? C19 C18 H18A 113.7 . . ? C17 C18 H18B 113.7 . . ? C19 C18 H18B 113.7 . . ? H18A C18 H18B 110.9 . . ? C18 C19 C20 118.0(13) . . ? C18 C19 H19A 107.8 . . ? C20 C19 H19A 107.8 . . ? C18 C19 H19B 107.8 . . ? C20 C19 H19B 107.8 . . ? H19A C19 H19B 107.1 . . ? O3 C20 C19 99.2(11) . . ? O3 C20 H20A 111.9 . . ? C19 C20 H20A 111.9 . . ? O3 C20 H20B 111.9 . . ? C19 C20 H20B 111.9 . . ? H20A C20 H20B 109.6 . . ? C20 O3 C17 103.8(11) . . ? O4 C21 C22 113(2) . . ? O4 C21 H21A 109.1 . . ? C22 C21 H21A 109.1 . . ? O4 C21 H21B 109.1 . . ? C22 C21 H21B 109.1 . . ? H21A C21 H21B 107.8 . . ? C21 C22 C23 98.5(19) . . ? C21 C22 H22A 112.1 . . ? C23 C22 H22A 112.1 . . ? C21 C22 H22B 112.1 . . ? C23 C22 H22B 112.1 . . ? H22A C22 H22B 109.7 . . ? C24 C23 C22 101.2(16) . . ? C24 C23 H23A 111.5 . . ? C22 C23 H23A 111.5 . . ? C24 C23 H23B 111.5 . . ? C22 C23 H23B 111.5 . . ? H23A C23 H23B 109.3 . . ? O4 C24 C23 112.8(17) . . ? O4 C24 H24A 109.0 . . ? C23 C24 H24A 109.0 . . ? O4 C24 H24B 109.0 . . ? C23 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? C21 O4 C24 102(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 C4 C1 C2 O1 -179.1(5) . . . . ? P1 C1 C2 O1 -7.1(7) . . . . ? C4 C1 C2 N1 -1.1(7) . . . . ? P1 C1 C2 N1 170.9(4) . . . . ? C2 C1 C4 N2 0.0(8) . . . . ? P1 C1 C4 N2 -171.0(4) . . . . ? C10 C5 C6 C7 -0.6(8) . . . . ? P1 C5 C6 C7 178.4(4) . . . . ? C5 C6 C7 C8 -0.3(9) . . . . ? C6 C7 C8 C9 0.5(10) . . . . ? C7 C8 C9 C10 0.1(9) . . . . ? C6 C5 C10 C9 1.3(7) . . . . ? P1 C5 C10 C9 -177.7(4) . . . . ? C8 C9 C10 C5 -1.0(8) . . . . ? C16 C11 C12 C13 -1.2(7) . . . . ? P1 C11 C12 C13 -179.9(3) . . . . ? C11 C12 C13 C14 1.5(7) . . . . ? C12 C13 C14 C15 -0.6(8) . . . . ? C13 C14 C15 C16 -0.6(9) . . . . ? C12 C11 C16 C15 0.0(8) . . . . ? P1 C11 C16 C15 178.7(5) . . . . ? C14 C15 C16 C11 0.9(9) . . . . ? O2 C3 N1 C2 -179.9(6) . . . . ? N2 C3 N1 C2 -0.6(9) . . . . ? O1 C2 N1 C3 179.6(6) . . . . ? C1 C2 N1 C3 1.4(9) . . . . ? C1 C4 N2 C3 1.0(9) . . . . ? O2 C3 N2 C4 178.6(6) . . . . ? N1 C3 N2 C4 -0.6(9) . . . . ? C4 C1 P1 C11 -9.8(5) . . . . ? C2 C1 P1 C11 179.0(4) . . . . ? C4 C1 P1 C5 -121.9(5) . . . . ? C2 C1 P1 C5 66.9(4) . . . . ? C4 C1 P1 Au1 114.8(5) . . . . ? C2 C1 P1 Au1 -56.5(4) . . . . ? C16 C11 P1 C1 126.1(4) . . . . ? C12 C11 P1 C1 -55.2(4) . . . . ? C16 C11 P1 C5 -120.7(4) . . . . ? C12 C11 P1 C5 58.0(4) . . . . ? C16 C11 P1 Au1 6.1(4) . . . . ? C12 C11 P1 Au1 -175.2(3) . . . . ? C6 C5 P1 C1 16.0(5) . . . . ? C10 C5 P1 C1 -165.0(4) . . . . ? C6 C5 P1 C11 -96.4(4) . . . . ? C10 C5 P1 C11 82.6(4) . . . . ? C6 C5 P1 Au1 135.8(4) . . . . ? C10 C5 P1 Au1 -45.2(4) . . . . ? O3 C17 C18 C19 20(3) . . . . ? C17 C18 C19 C20 2(3) . . . . ? C18 C19 C20 O3 -21(3) . . . . ? C19 C20 O3 C17 29.8(18) . . . . ? C18 C17 O3 C20 -35(2) . . . . ? O4 C21 C22 C23 35(4) . . . . ? C21 C22 C23 C24 -33(3) . . . . ? C22 C23 C24 O4 25(2) . . . . ? C22 C21 O4 C24 -21(4) . . . . ? C23 C24 O4 C21 -4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.87(7) 1.94(8) 2.779(6) 162(7) 2_655 N2 H2 O1 0.85(6) 1.89(6) 2.743(5) 174(6) 6_566 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.082 _refine_diff_density_min -1.328 _refine_diff_density_rms 0.164 data_jml0729m _database_code_depnum_ccdc_archive 'CCDC 711932' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 Au Cl N2 O2 P, 0.5(C7H8)' _chemical_formula_sum 'C19.50 H17 Au Cl N2 O2 P' _chemical_formula_weight 574.74 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 32.581(3) _cell_length_b 11.6052(9) _cell_length_c 13.3809(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.9430(10) _cell_angle_gamma 90.00 _cell_volume 5056.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5329 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 28.22 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2200 _exptl_absorpt_coefficient_mu 6.001 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.542 _exptl_absorpt_correction_T_max 0.741 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25083 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 28.30 _reflns_number_total 6275 _reflns_number_gt 5195 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The toluene of crystallisation was disordered over two sites (related by a centre of inversion) and also in the position of the methyl group. The latter was modelled in two positions of relatve occupancy 58:42. The phenyl ring of the toiluene was restrained to be flat (FLAT 0.02) and the C-CH3 bond length restrained to be 1.52 angstroms. There was additional disordered solvent present which was treated using the SQUEEZE algorithm, see below. ; _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^)+(0.0796P)^2^+13.7207P] 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 6275 _refine_ls_number_parameters 241 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1248 _refine_ls_wR_factor_gt 0.1217 _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.675461(6) 0.649945(19) 0.460493(14) 0.02160(9) Uani 1 1 d . . . C1 C 0.62936(16) 0.4844(6) 0.2916(4) 0.0261(12) Uani 1 1 d . . . C2 C 0.59165(18) 0.4894(7) 0.3445(4) 0.0346(15) Uani 1 1 d . . . C3 C 0.5536(2) 0.4866(10) 0.1831(5) 0.059(3) Uani 1 1 d . . . C4 C 0.62741(18) 0.4859(7) 0.1901(4) 0.0339(15) Uani 1 1 d . . . H4 H 0.6522 0.4850 0.1548 0.041 Uiso 1 1 calc R . . C5 C 0.6763(2) 0.3593(5) 0.4408(5) 0.0276(13) Uani 1 1 d . . . C6 C 0.7024(2) 0.3529(6) 0.5265(5) 0.0379(16) Uani 1 1 d . . . H6 H 0.7186 0.4178 0.5457 0.045 Uiso 1 1 calc R . . C7 C 0.7047(3) 0.2523(8) 0.5839(6) 0.053(2) Uani 1 1 d . . . H7 H 0.7218 0.2487 0.6428 0.064 Uiso 1 1 calc R . . C8 C 0.6817(3) 0.1590(7) 0.5532(7) 0.057(3) Uani 1 1 d . . . H8 H 0.6836 0.0895 0.5906 0.068 Uiso 1 1 calc R . . C9 C 0.6556(3) 0.1635(7) 0.4681(7) 0.055(2) Uani 1 1 d . . . H9 H 0.6396 0.0983 0.4490 0.066 Uiso 1 1 calc R . . C10 C 0.6534(3) 0.2619(7) 0.4128(5) 0.0470(18) Uani 1 1 d . . . H10 H 0.6360 0.2645 0.3545 0.056 Uiso 1 1 calc R . . C11 C 0.71834(16) 0.4774(5) 0.2859(4) 0.0205(10) Uani 1 1 d . . . C12 C 0.72026(19) 0.3861(5) 0.2178(4) 0.0283(12) Uani 1 1 d . . . H12 H 0.6986 0.3315 0.2126 0.034 Uiso 1 1 calc R . . C13 C 0.75383(19) 0.3760(5) 0.1584(4) 0.0244(11) Uani 1 1 d . . . H13 H 0.7551 0.3136 0.1127 0.029 Uiso 1 1 calc R . . C14 C 0.78566(18) 0.4544(6) 0.1636(5) 0.0331(13) Uani 1 1 d . . . H14 H 0.8086 0.4459 0.1223 0.040 Uiso 1 1 calc R . . C15 C 0.7836(2) 0.5468(7) 0.2308(5) 0.0424(17) Uani 1 1 d . . . H15 H 0.8051 0.6021 0.2352 0.051 Uiso 1 1 calc R . . C16 C 0.7496(2) 0.5567(6) 0.2915(5) 0.0349(14) Uani 1 1 d . . . H16 H 0.7481 0.6192 0.3370 0.042 Uiso 1 1 calc R . . Cl1 Cl 0.67019(5) 0.81511(14) 0.55274(10) 0.0311(3) Uani 1 1 d . . . N1 N 0.55635(17) 0.4907(7) 0.2860(4) 0.054(2) Uani 1 1 d . . . H1 H 0.5331 0.4946 0.3173 0.065 Uiso 1 1 calc R . . N2 N 0.59078(15) 0.4886(7) 0.1376(4) 0.0459(17) Uani 1 1 d . . . H2 H 0.5910 0.4917 0.0719 0.069 Uiso 1 1 calc R . . O1 O 0.59008(14) 0.4908(5) 0.4353(3) 0.0456(13) Uani 1 1 d . . . O2 O 0.52148(15) 0.4834(7) 0.1342(3) 0.075(2) Uani 1 1 d . . . P1 P 0.67582(4) 0.49006(13) 0.36853(10) 0.0219(3) Uani 1 1 d . . . C17 C 0.3952(6) 0.7716(12) 0.2431(14) 0.060(4) Uiso 0.50 1 d PD A . H17 H 0.3661 0.7790 0.2420 0.072 Uiso 0.50 1 calc PR . . C18 C 0.4187(7) 0.7585(12) 0.3341(17) 0.078(6) Uiso 0.50 1 d PD . . H18 H 0.4043 0.7566 0.3947 0.093 Uiso 0.50 1 calc PR A . C19A C 0.4629(7) 0.7479(13) 0.3407(17) 0.077(6) Uiso 0.29(4) 1 d PD A -1 C19B C 0.4629(7) 0.7479(13) 0.3407(17) 0.077(6) Uiso 0.21(4) 1 d PD A -2 H19B H 0.4776 0.7388 0.4028 0.093 Uiso 0.21(4) 1 calc PR A -2 C20 C 0.4820(7) 0.7519(14) 0.252(2) 0.079(6) Uiso 0.50 1 d PD A -2 H20 H 0.5111 0.7460 0.2552 0.095 Uiso 0.50 1 calc PR A -2 C21A C 0.4635(9) 0.7638(17) 0.154(2) 0.111(9) Uiso 0.29(4) 1 d PD A -2 H21A H 0.4786 0.7658 0.0942 0.134 Uiso 0.29(4) 1 calc PR A -2 C21B C 0.4635(9) 0.7638(17) 0.154(2) 0.111(9) Uiso 0.21(4) 1 d PD A -1 C22 C 0.4173(8) 0.7729(15) 0.156(2) 0.093(7) Uiso 0.50 1 d PD . . H22 H 0.4025 0.7800 0.0938 0.112 Uiso 0.50 1 calc PR A . C23A C 0.4808(17) 0.735(2) 0.447(2) 0.11(2) Uiso 0.29(4) 1 d PD A -1 H23A H 0.4822 0.6525 0.4635 0.172 Uiso 0.29(4) 1 d PR A -1 H23B H 0.4624 0.7737 0.4922 0.172 Uiso 0.29(4) 1 d PR A -1 H23C H 0.5082 0.7687 0.4533 0.172 Uiso 0.29(4) 1 d PR A -1 C23B C 0.477(4) 0.770(3) 0.046(4) 0.20(6) Uiso 0.21(4) 1 d PD A -1 H23D H 0.5024 0.8151 0.0514 0.294 Uiso 0.21(4) 1 d PR A -1 H23E H 0.4580 0.8049 -0.0030 0.294 Uiso 0.21(4) 1 d PR A -1 H23F H 0.4836 0.6910 0.0251 0.294 Uiso 0.21(4) 1 d PR A -1 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 0.02306(13) 0.03060(14) 0.01103(12) -0.00243(7) -0.00085(8) 0.00097(8) C1 0.019(3) 0.052(4) 0.007(2) -0.003(2) -0.0010(18) -0.005(2) C2 0.021(3) 0.072(5) 0.011(2) -0.006(3) 0.002(2) -0.005(3) C3 0.024(3) 0.143(9) 0.012(3) -0.008(4) 0.000(2) 0.000(4) C4 0.020(3) 0.075(5) 0.007(2) -0.006(3) -0.0001(19) -0.006(3) C5 0.040(4) 0.025(3) 0.018(3) -0.002(2) 0.008(2) 0.001(2) C6 0.044(4) 0.049(4) 0.020(3) 0.000(3) -0.002(3) 0.018(3) C7 0.070(5) 0.056(5) 0.034(4) 0.014(3) 0.005(4) 0.028(4) C8 0.082(7) 0.036(4) 0.054(5) 0.014(3) 0.033(5) 0.017(4) C9 0.073(6) 0.042(4) 0.053(5) -0.005(3) 0.035(5) -0.014(4) C10 0.063(5) 0.054(5) 0.024(3) -0.005(3) 0.002(3) -0.019(4) C11 0.021(2) 0.030(3) 0.010(2) -0.0025(19) -0.0027(18) 0.001(2) C12 0.032(3) 0.030(3) 0.023(3) 0.003(2) -0.002(2) 0.003(2) C13 0.034(3) 0.023(3) 0.016(2) -0.002(2) -0.001(2) 0.006(2) C14 0.024(3) 0.040(3) 0.035(3) -0.008(3) 0.008(2) 0.000(3) C15 0.034(3) 0.052(4) 0.042(4) -0.024(3) 0.015(3) -0.020(3) C16 0.038(3) 0.039(3) 0.029(3) -0.022(3) 0.007(3) -0.005(3) Cl1 0.0426(8) 0.0315(7) 0.0192(6) -0.0031(6) -0.0001(6) 0.0072(6) N1 0.022(3) 0.129(6) 0.010(2) -0.011(3) 0.0019(19) -0.007(3) N2 0.020(2) 0.110(6) 0.008(2) -0.005(3) -0.0004(18) -0.009(3) O1 0.030(2) 0.097(4) 0.0102(18) -0.012(2) -0.0020(16) -0.007(2) O2 0.025(2) 0.186(8) 0.012(2) -0.015(3) -0.0030(18) 0.000(3) P1 0.0222(7) 0.0339(8) 0.0094(5) -0.0036(5) -0.0009(5) -0.0017(6) _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 2.2267(14) . ? Au1 Cl1 2.2894(15) . ? C1 C4 1.357(7) . ? C1 C2 1.440(7) . ? C1 P1 1.802(5) . ? C2 O1 1.217(7) . ? C2 N1 1.369(7) . ? C3 O2 1.216(8) . ? C3 N2 1.374(8) . ? C3 N1 1.378(8) . ? C4 N2 1.365(7) . ? C4 H4 0.9500 . ? C5 C10 1.399(9) . ? C5 C6 1.405(9) . ? C5 P1 1.798(6) . ? C6 C7 1.399(10) . ? C6 H6 0.9500 . ? C7 C8 1.372(13) . ? C7 H7 0.9500 . ? C8 C9 1.398(14) . ? C8 H8 0.9500 . ? C9 C10 1.361(11) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.372(8) . ? C11 C12 1.399(8) . ? C11 P1 1.808(5) . ? C12 C13 1.379(8) . ? C12 H12 0.9500 . ? C13 C14 1.379(9) . ? C13 H13 0.9500 . ? C14 C15 1.403(9) . ? C14 H14 0.9500 . ? C15 C16 1.401(9) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? C17 C22 1.39(3) . ? C17 C18 1.42(3) . ? C17 H17 0.9500 . ? C18 C19A 1.45(3) . ? C18 H18 0.9500 . ? C19A C23A 1.522(5) . ? C20 C21A 1.43(4) . ? C20 H20 0.9500 . ? C21A C22 1.51(4) . ? C21A H21A 0.9500 . ? C22 H22 0.9500 . ? C23A H23A 0.9800 . ? C23A H23B 0.9800 . ? C23A H23C 0.9800 . ? C23B H23D 0.9800 . ? C23B H23E 0.9800 . ? C23B H23F 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 P1 Au1 Cl1 175.94(5) . . ? C4 C1 C2 118.7(5) . . ? C4 C1 P1 125.5(4) . . ? C2 C1 P1 115.6(4) . . ? O1 C2 N1 120.5(5) . . ? O1 C2 C1 123.8(5) . . ? N1 C2 C1 115.7(5) . . ? O2 C3 N2 121.2(6) . . ? O2 C3 N1 124.4(6) . . ? N2 C3 N1 114.5(6) . . ? C1 C4 N2 121.7(5) . . ? C1 C4 H4 119.1 . . ? N2 C4 H4 119.1 . . ? C10 C5 C6 118.5(6) . . ? C10 C5 P1 122.9(5) . . ? C6 C5 P1 118.5(5) . . ? C7 C6 C5 120.9(7) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C8 C7 C6 118.3(8) . . ? C8 C7 H7 120.8 . . ? C6 C7 H7 120.8 . . ? C7 C8 C9 121.7(7) . . ? C7 C8 H8 119.2 . . ? C9 C8 H8 119.2 . . ? C10 C9 C8 119.6(8) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C5 120.9(7) . . ? C9 C10 H10 119.5 . . ? C5 C10 H10 119.5 . . ? C16 C11 C12 119.6(5) . . ? C16 C11 P1 119.6(4) . . ? C12 C11 P1 120.8(4) . . ? C13 C12 C11 119.6(6) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 121.7(6) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 119.0(6) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 119.3(6) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C11 C16 C15 120.9(5) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C2 N1 C3 126.6(5) . . ? C2 N1 H1 116.7 . . ? C3 N1 H1 116.7 . . ? C4 N2 C3 122.6(5) . . ? C4 N2 H2 118.7 . . ? C3 N2 H2 118.7 . . ? C5 P1 C1 105.6(3) . . ? C5 P1 C11 105.5(3) . . ? C1 P1 C11 107.1(2) . . ? C5 P1 Au1 114.0(2) . . ? C1 P1 Au1 109.0(2) . . ? C11 P1 Au1 115.11(18) . . ? C22 C17 C18 116(2) . . ? C22 C17 H17 122.0 . . ? C18 C17 H17 122.0 . . ? C17 C18 C19A 125(2) . . ? C17 C18 H18 117.7 . . ? C19A C18 H18 117.7 . . ? C18 C19A C23A 114(3) . . ? C21A C20 H20 116.1 . . ? C20 C21A C22 112(3) . . ? C20 C21A H21A 123.8 . . ? C22 C21A H21A 123.8 . . ? C17 C22 C21A 124(2) . . ? C17 C22 H22 118.0 . . ? C21A C22 H22 118.0 . . ? C19A C23A H23A 109.0 . . ? C19A C23A H23B 108.0 . . ? H23A C23A H23B 109.5 . . ? C19A C23A H23C 111.3 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? H23D C23B H23E 109.5 . . ? H23D C23B H23F 109.5 . . ? H23E C23B H23F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 C1 C2 O1 -178.5(7) . . . . ? P1 C1 C2 O1 -4.0(10) . . . . ? C4 C1 C2 N1 2.5(11) . . . . ? P1 C1 C2 N1 177.0(6) . . . . ? C2 C1 C4 N2 -1.9(11) . . . . ? P1 C1 C4 N2 -175.8(6) . . . . ? C10 C5 C6 C7 -1.3(10) . . . . ? P1 C5 C6 C7 -178.4(6) . . . . ? C5 C6 C7 C8 1.5(11) . . . . ? C6 C7 C8 C9 -1.6(12) . . . . ? C7 C8 C9 C10 1.3(13) . . . . ? C8 C9 C10 C5 -1.0(12) . . . . ? C6 C5 C10 C9 1.0(11) . . . . ? P1 C5 C10 C9 178.0(6) . . . . ? C16 C11 C12 C13 1.1(9) . . . . ? P1 C11 C12 C13 -177.5(4) . . . . ? C11 C12 C13 C14 -0.5(9) . . . . ? C12 C13 C14 C15 -0.3(10) . . . . ? C13 C14 C15 C16 0.5(11) . . . . ? C12 C11 C16 C15 -0.8(10) . . . . ? P1 C11 C16 C15 177.7(6) . . . . ? C14 C15 C16 C11 0.0(11) . . . . ? O1 C2 N1 C3 -178.4(9) . . . . ? C1 C2 N1 C3 0.7(13) . . . . ? O2 C3 N1 C2 176.9(10) . . . . ? N2 C3 N1 C2 -4.2(15) . . . . ? C1 C4 N2 C3 -1.9(13) . . . . ? O2 C3 N2 C4 -176.4(9) . . . . ? N1 C3 N2 C4 4.8(14) . . . . ? C10 C5 P1 C1 20.4(6) . . . . ? C6 C5 P1 C1 -162.6(5) . . . . ? C10 C5 P1 C11 -92.8(6) . . . . ? C6 C5 P1 C11 84.2(5) . . . . ? C10 C5 P1 Au1 140.0(5) . . . . ? C6 C5 P1 Au1 -43.0(6) . . . . ? C4 C1 P1 C5 -120.0(6) . . . . ? C2 C1 P1 C5 66.0(6) . . . . ? C4 C1 P1 C11 -7.9(7) . . . . ? C2 C1 P1 C11 178.0(5) . . . . ? C4 C1 P1 Au1 117.2(6) . . . . ? C2 C1 P1 Au1 -56.9(6) . . . . ? C16 C11 P1 C5 -119.4(5) . . . . ? C12 C11 P1 C5 59.1(5) . . . . ? C16 C11 P1 C1 128.4(5) . . . . ? C12 C11 P1 C1 -53.0(5) . . . . ? C16 C11 P1 Au1 7.1(6) . . . . ? C12 C11 P1 Au1 -174.4(4) . . . . ? C22 C17 C18 C19A 0.6(5) . . . . ? C17 C18 C19A C23A -179.9(5) . . . . ? C18 C17 C22 C21A -1.2(11) . . . . ? C20 C21A C22 C17 0.9(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O2 0.88 1.92 2.786(7) 169.0 2_655 N2 H2 O1 0.88 1.84 2.716(6) 175.8 6_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.957 _refine_diff_density_min -2.051 _refine_diff_density_rms 0.227 # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.439 488 219 ' ' 2 0.000 0.500 0.745 488 219 ' ' _platon_squeeze_details ; ; # Attachment '3vac.cif' data_jml0727m _database_code_depnum_ccdc_archive 'CCDC 711933' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 Au Cl N2 O2 P, O' _chemical_formula_sum 'C16 H13 Au Cl N2 O3 P' _chemical_formula_weight 544.67 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/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 32.580(7) _cell_length_b 11.448(3) _cell_length_c 13.397(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.195(4) _cell_angle_gamma 90.00 _cell_volume 4995.7(19) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5112 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 28.26 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 6.072 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.338 _exptl_absorpt_correction_T_max 0.690 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23748 _diffrn_reflns_av_R_equivalents 0.0503 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.31 _reflns_number_total 6195 _reflns_number_gt 4933 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. O3 is believed to be the oxygen of a THF or water; the remainder of the atoms bonded to the oxygen and additional solvent was disordered. The disordered solvent was accounted for by using the SQUEEZE algorithm, see below. ; _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^)+(0.0774P)^2^+119.6950P] 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 6195 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0756 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.1641 _refine_ls_wR_factor_gt 0.1582 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 Au1 Au 0.326383(11) 0.65341(3) 0.03742(2) 0.02603(12) Uani 1 1 d . . . C1 C 0.3715(3) 0.4923(8) 0.2101(5) 0.0268(18) Uani 1 1 d . . . C2 C 0.4101(3) 0.4978(11) 0.1566(7) 0.042(3) Uani 1 1 d . . . C3 C 0.4461(3) 0.5245(14) 0.3186(7) 0.055(4) Uani 1 1 d . . . C4 C 0.3728(3) 0.5002(10) 0.3106(6) 0.038(2) Uani 1 1 d . . . H4 H 0.3480 0.4944 0.3462 0.046 Uiso 1 1 calc R . . C5 C 0.2834(3) 0.4792(7) 0.2145(6) 0.0253(17) Uani 1 1 d . . . C6 C 0.2815(3) 0.3905(7) 0.2827(6) 0.0278(19) Uani 1 1 d . . . H6 H 0.3034 0.3359 0.2874 0.033 Uiso 1 1 calc R . . C7 C 0.2479(3) 0.3782(8) 0.3461(6) 0.0289(18) Uani 1 1 d . . . H7 H 0.2469 0.3147 0.3916 0.035 Uiso 1 1 calc R . . C8 C 0.2171(3) 0.4567(9) 0.3420(7) 0.037(2) Uani 1 1 d . . . H8 H 0.1949 0.4511 0.3867 0.045 Uiso 1 1 calc R . . C9 C 0.2180(3) 0.5467(11) 0.2713(9) 0.050(3) Uani 1 1 d . . . H9 H 0.1957 0.5997 0.2653 0.060 Uiso 1 1 calc R . . C10 C 0.2516(3) 0.5588(9) 0.2099(7) 0.037(2) Uani 1 1 d . . . H10 H 0.2527 0.6223 0.1643 0.045 Uiso 1 1 calc R . . C11 C 0.3264(3) 0.3570(7) 0.0600(6) 0.0249(17) Uani 1 1 d . . . C12 C 0.3522(4) 0.2618(10) 0.0864(8) 0.049(3) Uani 1 1 d . . . H12 H 0.3710 0.2676 0.1414 0.059 Uiso 1 1 calc R . . C13 C 0.3497(5) 0.1624(10) 0.0316(10) 0.057(3) Uani 1 1 d . . . H13 H 0.3667 0.0980 0.0498 0.068 Uiso 1 1 calc R . . C14 C 0.3231(5) 0.1514(11) -0.0505(9) 0.059(4) Uani 1 1 d . . . H14 H 0.3221 0.0813 -0.0883 0.071 Uiso 1 1 calc R . . C15 C 0.2982(4) 0.2440(11) -0.0755(8) 0.051(3) Uani 1 1 d . . . H15 H 0.2796 0.2371 -0.1309 0.061 Uiso 1 1 calc R . . C16 C 0.2995(3) 0.3470(9) -0.0220(7) 0.034(2) Uani 1 1 d . . . H16 H 0.2823 0.4106 -0.0408 0.041 Uiso 1 1 calc R . . Cl1 Cl 0.33158(9) 0.8199(2) -0.05692(16) 0.0380(5) Uani 1 1 d . . . N1 N 0.4444(3) 0.5163(11) 0.2159(6) 0.056(3) Uani 1 1 d . . . H1 H 0.4678 0.5238 0.1850 0.067 Uiso 1 1 calc R . . N2 N 0.4087(3) 0.5163(10) 0.3624(5) 0.047(3) Uani 1 1 d . . . H2 H 0.4078 0.5218 0.4278 0.057 Uiso 1 1 calc R . . O1 O 0.4128(2) 0.4955(8) 0.0658(5) 0.050(2) Uani 1 1 d . . . O2 O 0.4778(2) 0.5373(12) 0.3660(5) 0.082(4) Uani 1 1 d . . . P1 P 0.32602(7) 0.4924(2) 0.13162(14) 0.0241(4) Uani 1 1 d . . . O3 O 0.4359(2) 0.8656(6) 0.3147(4) 0.0316(14) 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 Au1 0.0331(2) 0.03170(19) 0.01318(16) 0.00186(12) -0.00262(11) -0.00124(14) C1 0.037(5) 0.034(5) 0.009(3) 0.004(3) -0.004(3) -0.006(4) C2 0.031(5) 0.077(8) 0.017(4) 0.001(4) -0.002(3) 0.003(5) C3 0.034(6) 0.114(11) 0.017(4) 0.017(5) -0.002(4) -0.006(6) C4 0.028(5) 0.070(7) 0.017(4) 0.004(4) 0.000(3) -0.003(5) C5 0.030(4) 0.029(4) 0.018(3) -0.001(3) -0.003(3) -0.001(3) C6 0.047(5) 0.009(3) 0.026(4) -0.014(3) -0.007(4) 0.003(3) C7 0.036(5) 0.031(4) 0.020(4) 0.004(3) -0.006(3) -0.006(4) C8 0.032(5) 0.044(6) 0.036(5) 0.006(4) 0.007(4) -0.001(4) C9 0.037(6) 0.058(7) 0.057(7) 0.036(6) 0.010(5) 0.014(5) C10 0.040(5) 0.036(5) 0.035(5) 0.017(4) 0.006(4) 0.008(4) C11 0.038(5) 0.020(4) 0.017(3) 0.003(3) 0.002(3) 0.001(3) C12 0.067(8) 0.046(6) 0.035(5) 0.006(5) -0.005(5) 0.013(6) C13 0.087(10) 0.036(6) 0.048(7) 0.006(5) 0.011(6) 0.006(6) C14 0.096(11) 0.044(7) 0.039(6) -0.018(5) 0.017(6) -0.019(7) C15 0.067(8) 0.053(7) 0.032(5) -0.007(5) -0.003(5) -0.026(6) C16 0.037(5) 0.044(6) 0.022(4) 0.005(4) -0.007(4) -0.009(4) Cl1 0.0575(15) 0.0343(12) 0.0221(10) 0.0038(8) -0.0011(9) -0.0036(10) N1 0.027(4) 0.127(10) 0.013(3) 0.005(5) -0.002(3) -0.003(5) N2 0.030(4) 0.102(8) 0.009(3) -0.004(4) -0.010(3) 0.006(5) O1 0.037(4) 0.102(7) 0.010(3) 0.001(3) -0.002(3) 0.002(4) O2 0.030(4) 0.200(13) 0.016(3) 0.001(5) -0.007(3) -0.001(6) P1 0.0292(11) 0.0325(11) 0.0104(8) -0.0001(8) -0.0037(7) 0.0008(9) O3 0.031(3) 0.053(4) 0.010(2) -0.011(2) -0.004(2) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 P1 2.234(2) . ? Au1 Cl1 2.295(2) . ? C1 C4 1.350(11) . ? C1 C2 1.462(13) . ? C1 P1 1.798(9) . ? C2 O1 1.221(11) . ? C2 N1 1.374(12) . ? C3 O2 1.209(13) . ? C3 N2 1.368(13) . ? C3 N1 1.379(12) . ? C4 N2 1.359(12) . ? C4 H4 0.9500 . ? C5 C6 1.368(12) . ? C5 C10 1.379(13) . ? C5 P1 1.804(9) . ? C6 C7 1.406(13) . ? C6 H6 0.9500 . ? C7 C8 1.348(14) . ? C7 H7 0.9500 . ? C8 C9 1.401(14) . ? C8 H8 0.9500 . ? C9 C10 1.389(14) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.394(12) . ? C11 C12 1.417(14) . ? C11 P1 1.823(8) . ? C12 C13 1.356(17) . ? C12 H12 0.9500 . ? C13 C14 1.39(2) . ? C13 H13 0.9500 . ? C14 C15 1.37(2) . ? C14 H14 0.9500 . ? C15 C16 1.380(15) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N1 H1 0.8800 . ? N2 H2 0.8800 . ? 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 176.00(9) . . ? C4 C1 C2 118.4(8) . . ? C4 C1 P1 126.4(7) . . ? C2 C1 P1 114.9(6) . . ? O1 C2 N1 120.3(9) . . ? O1 C2 C1 124.6(9) . . ? N1 C2 C1 114.9(8) . . ? O2 C3 N2 122.9(9) . . ? O2 C3 N1 123.3(10) . . ? N2 C3 N1 113.9(9) . . ? C1 C4 N2 121.9(9) . . ? C1 C4 H4 119.0 . . ? N2 C4 H4 119.0 . . ? C6 C5 C10 118.5(8) . . ? C6 C5 P1 121.3(7) . . ? C10 C5 P1 120.3(7) . . ? C5 C6 C7 121.6(8) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C8 C7 C6 119.8(8) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 119.4(9) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 120.2(10) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C5 C10 C9 120.4(9) . . ? C5 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C16 C11 C12 119.6(9) . . ? C16 C11 P1 118.3(7) . . ? C12 C11 P1 122.2(7) . . ? C13 C12 C11 118.8(11) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C12 C13 C14 122.2(12) . . ? C12 C13 H13 118.9 . . ? C14 C13 H13 118.9 . . ? C15 C14 C13 118.6(10) . . ? C15 C14 H14 120.7 . . ? C13 C14 H14 120.7 . . ? C14 C15 C16 121.4(11) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C15 C16 C11 119.5(10) . . ? C15 C16 H16 120.3 . . ? C11 C16 H16 120.3 . . ? C2 N1 C3 127.1(9) . . ? C2 N1 H1 116.4 . . ? C3 N1 H1 116.4 . . ? C4 N2 C3 123.7(8) . . ? C4 N2 H2 118.1 . . ? C3 N2 H2 118.1 . . ? C1 P1 C5 106.0(4) . . ? C1 P1 C11 107.0(4) . . ? C5 P1 C11 105.5(4) . . ? C1 P1 Au1 108.5(3) . . ? C5 P1 Au1 115.5(3) . . ? C11 P1 Au1 113.8(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 C4 C1 C2 O1 -177.5(12) . . . . ? P1 C1 C2 O1 -4.4(16) . . . . ? C4 C1 C2 N1 -2.9(16) . . . . ? P1 C1 C2 N1 170.2(9) . . . . ? C2 C1 C4 N2 1.9(17) . . . . ? P1 C1 C4 N2 -170.3(9) . . . . ? C10 C5 C6 C7 1.1(13) . . . . ? P1 C5 C6 C7 -178.6(6) . . . . ? C5 C6 C7 C8 -1.7(13) . . . . ? C6 C7 C8 C9 2.9(15) . . . . ? C7 C8 C9 C10 -3.7(18) . . . . ? C6 C5 C10 C9 -1.8(15) . . . . ? P1 C5 C10 C9 177.8(9) . . . . ? C8 C9 C10 C5 3.1(19) . . . . ? C16 C11 C12 C13 -0.9(16) . . . . ? P1 C11 C12 C13 177.6(9) . . . . ? C11 C12 C13 C14 1(2) . . . . ? C12 C13 C14 C15 -1(2) . . . . ? C13 C14 C15 C16 0.8(19) . . . . ? C14 C15 C16 C11 -0.7(17) . . . . ? C12 C11 C16 C15 0.8(14) . . . . ? P1 C11 C16 C15 -177.8(8) . . . . ? O1 C2 N1 C3 178.1(14) . . . . ? C1 C2 N1 C3 3(2) . . . . ? O2 C3 N1 C2 177.6(15) . . . . ? N2 C3 N1 C2 -2(2) . . . . ? C1 C4 N2 C3 -0.8(19) . . . . ? O2 C3 N2 C4 -179.0(15) . . . . ? N1 C3 N2 C4 1(2) . . . . ? C4 C1 P1 C5 -9.8(10) . . . . ? C2 C1 P1 C5 177.8(8) . . . . ? C4 C1 P1 C11 -122.0(9) . . . . ? C2 C1 P1 C11 65.5(8) . . . . ? C4 C1 P1 Au1 114.8(9) . . . . ? C2 C1 P1 Au1 -57.7(8) . . . . ? C6 C5 P1 C1 -53.7(8) . . . . ? C10 C5 P1 C1 126.7(8) . . . . ? C6 C5 P1 C11 59.6(8) . . . . ? C10 C5 P1 C11 -120.0(8) . . . . ? C6 C5 P1 Au1 -173.8(6) . . . . ? C10 C5 P1 Au1 6.6(9) . . . . ? C16 C11 P1 C1 -166.0(7) . . . . ? C12 C11 P1 C1 15.5(9) . . . . ? C16 C11 P1 C5 81.4(8) . . . . ? C12 C11 P1 C5 -97.2(9) . . . . ? C16 C11 P1 Au1 -46.2(8) . . . . ? C12 C11 P1 Au1 135.3(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.88 1.86 2.729(9) 168 6_566 N1 H1 O2 0.88 1.92 2.793(12) 173 2_655 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 4.230 _refine_diff_density_min -2.859 _refine_diff_density_rms 0.263 # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.188 802 245 ' ' 2 0.000 0.500 0.882 803 245 ' ' 3 0.355 0.190 0.761 6 2 ' ' 4 0.645 0.190 0.739 6 3 ' ' 5 0.145 0.310 0.239 6 2 ' ' 6 0.855 0.310 0.261 6 1 ' ' 7 0.145 0.690 0.739 6 3 ' ' 8 0.855 0.690 0.761 6 2 ' ' 9 0.355 0.810 0.261 6 1 ' ' 10 0.645 0.810 0.239 6 2 ' ' _platon_squeeze_details ; ; # Attachment '4.cif' data_jml0735m _database_code_depnum_ccdc_archive 'CCDC 711934' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 Au Br N2 O2 P' _chemical_formula_sum 'C16 H13 Au Br N2 O2 P' _chemical_formula_weight 573.13 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 32.641(2) _cell_length_b 11.6174(7) _cell_length_c 13.4569(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.6150(10) _cell_angle_gamma 90.00 _cell_volume 5100.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5423 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 28.20 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2144 _exptl_absorpt_coefficient_mu 7.404 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.497 _exptl_absorpt_correction_T_max 0.801 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25693 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -43 _diffrn_reflns_limit_h_max 43 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 28.27 _reflns_number_total 6313 _reflns_number_gt 5566 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. There was a large amount of disordered solvent for which a satisfactory model could not be derived. Therefore the SQUEEZE algorithm was used to model this solvent (see below). ; _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^)+(0.0324P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6313 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0250 _refine_ls_R_factor_gt 0.0223 _refine_ls_wR_factor_ref 0.0587 _refine_ls_wR_factor_gt 0.0580 _refine_ls_goodness_of_fit_ref 0.984 _refine_ls_restrained_S_all 0.984 _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 Au1 Au 0.327235(3) 0.349005(8) 0.038589(6) 0.02218(4) Uani 1 1 d . . . Br1 Br 0.335513(10) 0.17717(2) -0.05835(2) 0.03461(7) Uani 1 1 d . . . C1 C 0.37184(8) 0.5086(2) 0.21056(17) 0.0237(5) Uani 1 1 d . . . C2 C 0.41004(8) 0.4999(3) 0.15748(18) 0.0288(6) Uani 1 1 d . . . C3 C 0.44633(9) 0.4772(3) 0.31822(19) 0.0389(7) Uani 1 1 d . . . C4 C 0.37341(8) 0.5020(2) 0.31063(18) 0.0278(6) Uani 1 1 d . . . H4 H 0.3487 0.5079 0.3459 0.033 Uiso 1 1 calc R . . C5 C 0.28384(8) 0.5199(2) 0.21520(17) 0.0218(5) Uani 1 1 d . . . C6 C 0.25279(9) 0.4385(3) 0.2122(2) 0.0355(7) Uani 1 1 d . . . H6 H 0.2540 0.3758 0.1671 0.043 Uiso 1 1 calc R . . C7 C 0.22005(10) 0.4483(3) 0.2748(2) 0.0470(9) Uani 1 1 d . . . H7 H 0.1989 0.3921 0.2720 0.056 Uiso 1 1 calc R . . C8 C 0.21771(9) 0.5381(3) 0.3411(2) 0.0341(6) Uani 1 1 d . . . H8 H 0.1953 0.5436 0.3844 0.041 Uiso 1 1 calc R . . C9 C 0.24838(9) 0.6205(2) 0.34383(19) 0.0263(5) Uani 1 1 d . . . H9 H 0.2471 0.6828 0.3893 0.032 Uiso 1 1 calc R . . C10 C 0.28089(8) 0.6124(2) 0.28081(18) 0.0249(5) Uani 1 1 d . . . H10 H 0.3014 0.6703 0.2821 0.030 Uiso 1 1 calc R . . C11 C 0.32589(8) 0.6403(2) 0.0618(2) 0.0234(5) Uani 1 1 d . . . C12 C 0.35052(10) 0.7345(2) 0.0892(2) 0.0348(6) Uani 1 1 d . . . H12 H 0.3689 0.7290 0.1451 0.042 Uiso 1 1 calc R . . C13 C 0.34805(13) 0.8354(3) 0.0348(3) 0.0471(9) Uani 1 1 d . . . H13 H 0.3650 0.8991 0.0529 0.057 Uiso 1 1 calc R . . C14 C 0.32085(14) 0.8440(3) -0.0465(3) 0.0488(10) Uani 1 1 d . . . H14 H 0.3187 0.9140 -0.0827 0.059 Uiso 1 1 calc R . . C15 C 0.29718(11) 0.7512(3) -0.0741(2) 0.0420(8) Uani 1 1 d . . . H15 H 0.2791 0.7571 -0.1304 0.050 Uiso 1 1 calc R . . C16 C 0.29935(10) 0.6486(2) -0.0209(2) 0.0309(6) Uani 1 1 d . . . H16 H 0.2829 0.5847 -0.0408 0.037 Uiso 1 1 calc R . . N1 N 0.44481(8) 0.4847(3) 0.21612(16) 0.0401(7) Uani 1 1 d . . . H1 H 0.4686(11) 0.470(3) 0.187(3) 0.046(10) Uiso 1 1 d . . . N2 N 0.40918(7) 0.4875(2) 0.36236(16) 0.0337(6) Uani 1 1 d . . . H2 H 0.4115(11) 0.481(3) 0.417(3) 0.048(11) Uiso 1 1 d . . . O1 O 0.41225(6) 0.50349(19) 0.06688(12) 0.0356(5) Uani 1 1 d . . . O2 O 0.47792(6) 0.4617(3) 0.36547(15) 0.0564(7) Uani 1 1 d . . . P1 P 0.32610(2) 0.50796(5) 0.13218(4) 0.02046(13) 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 Au1 0.02750(7) 0.02313(6) 0.01583(6) -0.00108(3) -0.00066(4) 0.00183(4) Br1 0.0527(2) 0.02526(13) 0.02588(14) -0.00424(10) 0.00102(13) 0.00585(12) C1 0.0213(13) 0.0356(14) 0.0139(11) -0.0018(10) -0.0015(9) 0.0021(10) C2 0.0245(14) 0.0486(17) 0.0131(11) -0.0014(10) -0.0005(10) 0.0007(12) C3 0.0272(15) 0.076(2) 0.0134(12) -0.0024(13) 0.0000(11) -0.0029(14) C4 0.0259(14) 0.0419(16) 0.0156(11) -0.0036(10) 0.0004(10) 0.0003(11) C5 0.0226(13) 0.0256(12) 0.0171(11) 0.0000(9) -0.0017(9) 0.0005(10) C6 0.0370(16) 0.0338(15) 0.0362(15) -0.0145(12) 0.0087(12) -0.0105(13) C7 0.0384(18) 0.056(2) 0.0474(19) -0.0229(16) 0.0138(15) -0.0198(16) C8 0.0262(15) 0.0454(17) 0.0308(14) -0.0053(12) 0.0043(11) 0.0008(12) C9 0.0314(15) 0.0263(12) 0.0214(12) 0.0004(10) 0.0024(11) 0.0053(11) C10 0.0277(14) 0.0246(12) 0.0224(12) -0.0001(10) 0.0002(10) -0.0025(11) C11 0.0284(15) 0.0243(13) 0.0174(11) 0.0015(9) 0.0014(10) 0.0032(10) C12 0.0417(18) 0.0330(15) 0.0295(14) -0.0014(12) -0.0026(12) -0.0092(13) C13 0.064(3) 0.0347(18) 0.044(2) 0.0013(13) 0.0103(17) -0.0118(15) C14 0.079(3) 0.0344(18) 0.0340(18) 0.0111(12) 0.0133(18) 0.0093(16) C15 0.054(2) 0.0441(18) 0.0274(15) 0.0075(13) -0.0033(14) 0.0146(15) C16 0.0377(17) 0.0332(15) 0.0216(13) -0.0010(10) -0.0056(12) 0.0069(11) N1 0.0212(13) 0.086(2) 0.0128(11) -0.0022(11) -0.0009(9) 0.0034(13) N2 0.0229(12) 0.0699(18) 0.0082(10) 0.0008(10) -0.0022(9) 0.0002(11) O1 0.0300(11) 0.0667(14) 0.0099(8) -0.0012(8) -0.0012(7) 0.0014(10) O2 0.0239(11) 0.128(2) 0.0165(10) 0.0040(12) -0.0043(8) -0.0010(12) P1 0.0222(3) 0.0251(3) 0.0139(3) -0.0011(2) -0.0017(2) 0.0008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 P1 2.2361(6) . ? Au1 Br1 2.4041(3) . ? C1 C4 1.348(3) . ? C1 C2 1.458(4) . ? C1 P1 1.803(3) . ? C2 O1 1.224(3) . ? C2 N1 1.375(3) . ? C3 O2 1.210(3) . ? C3 N2 1.370(4) . ? C3 N1 1.376(3) . ? C4 N2 1.353(3) . ? C4 H4 0.9500 . ? C5 C6 1.386(4) . ? C5 C10 1.396(3) . ? C5 P1 1.805(3) . ? C6 C7 1.384(4) . ? C6 H6 0.9500 . ? C7 C8 1.376(4) . ? C7 H7 0.9500 . ? C8 C9 1.385(4) . ? C8 H8 0.9500 . ? C9 C10 1.380(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C16 1.394(4) . ? C11 C12 1.401(4) . ? C11 P1 1.806(3) . ? C12 C13 1.384(4) . ? C12 H12 0.9500 . ? C13 C14 1.393(6) . ? C13 H13 0.9500 . ? C14 C15 1.371(5) . ? C14 H14 0.9500 . ? C15 C16 1.391(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N1 H1 0.90(3) . ? N2 H2 0.74(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag P1 Au1 Br1 174.409(19) . . ? C4 C1 C2 118.5(2) . . ? C4 C1 P1 126.3(2) . . ? C2 C1 P1 114.74(17) . . ? O1 C2 N1 120.3(2) . . ? O1 C2 C1 124.1(2) . . ? N1 C2 C1 115.5(2) . . ? O2 C3 N2 122.5(2) . . ? O2 C3 N1 122.7(3) . . ? N2 C3 N1 114.8(2) . . ? C1 C4 N2 121.9(2) . . ? C1 C4 H4 119.0 . . ? N2 C4 H4 119.0 . . ? C6 C5 C10 118.7(2) . . ? C6 C5 P1 120.03(19) . . ? C10 C5 P1 121.2(2) . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 121.0(3) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 119.2(3) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 120.3(3) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C5 120.6(2) . . ? C9 C10 H10 119.7 . . ? C5 C10 H10 119.7 . . ? C16 C11 C12 119.7(2) . . ? C16 C11 P1 118.1(2) . . ? C12 C11 P1 122.2(2) . . ? C13 C12 C11 119.9(3) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.1(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 119.9(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.9(3) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C11 119.4(3) . . ? C15 C16 H16 120.3 . . ? C11 C16 H16 120.3 . . ? C2 N1 C3 125.9(2) . . ? C2 N1 H1 119(2) . . ? C3 N1 H1 115(2) . . ? C4 N2 C3 123.3(2) . . ? C4 N2 H2 126(3) . . ? C3 N2 H2 111(3) . . ? C1 P1 C5 105.80(11) . . ? C1 P1 C11 107.12(12) . . ? C5 P1 C11 105.53(12) . . ? C1 P1 Au1 107.82(9) . . ? C5 P1 Au1 115.93(8) . . ? C11 P1 Au1 114.03(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 C4 C1 C2 O1 179.2(3) . . . . ? P1 C1 C2 O1 7.1(4) . . . . ? C4 C1 C2 N1 0.5(4) . . . . ? P1 C1 C2 N1 -171.6(2) . . . . ? C2 C1 C4 N2 -0.2(4) . . . . ? P1 C1 C4 N2 170.9(2) . . . . ? C10 C5 C6 C7 -1.3(4) . . . . ? P1 C5 C6 C7 -179.1(3) . . . . ? C5 C6 C7 C8 -0.2(5) . . . . ? C6 C7 C8 C9 0.9(5) . . . . ? C7 C8 C9 C10 0.0(4) . . . . ? C8 C9 C10 C5 -1.5(4) . . . . ? C6 C5 C10 C9 2.2(4) . . . . ? P1 C5 C10 C9 180.0(2) . . . . ? C16 C11 C12 C13 0.7(5) . . . . ? P1 C11 C12 C13 -177.6(3) . . . . ? C11 C12 C13 C14 0.7(5) . . . . ? C12 C13 C14 C15 -1.6(6) . . . . ? C13 C14 C15 C16 1.2(5) . . . . ? C14 C15 C16 C11 0.2(5) . . . . ? C12 C11 C16 C15 -1.1(4) . . . . ? P1 C11 C16 C15 177.2(2) . . . . ? O1 C2 N1 C3 -178.8(3) . . . . ? C1 C2 N1 C3 0.0(5) . . . . ? O2 C3 N1 C2 178.6(3) . . . . ? N2 C3 N1 C2 -0.7(5) . . . . ? C1 C4 N2 C3 -0.6(5) . . . . ? O2 C3 N2 C4 -178.3(3) . . . . ? N1 C3 N2 C4 1.0(5) . . . . ? C4 C1 P1 C5 8.8(3) . . . . ? C2 C1 P1 C5 -179.8(2) . . . . ? C4 C1 P1 C11 121.0(3) . . . . ? C2 C1 P1 C11 -67.6(2) . . . . ? C4 C1 P1 Au1 -115.8(2) . . . . ? C2 C1 P1 Au1 55.6(2) . . . . ? C6 C5 P1 C1 -124.8(2) . . . . ? C10 C5 P1 C1 57.4(2) . . . . ? C6 C5 P1 C11 121.8(2) . . . . ? C10 C5 P1 C11 -55.9(2) . . . . ? C6 C5 P1 Au1 -5.4(3) . . . . ? C10 C5 P1 Au1 176.82(18) . . . . ? C16 C11 P1 C1 164.8(2) . . . . ? C12 C11 P1 C1 -17.0(3) . . . . ? C16 C11 P1 C5 -82.8(2) . . . . ? C12 C11 P1 C5 95.4(3) . . . . ? C16 C11 P1 Au1 45.5(2) . . . . ? C12 C11 P1 Au1 -136.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.74(4) 2.02(4) 2.753(3) 168(4) 6_566 N1 H1 O2 0.90(3) 1.90(4) 2.792(3) 170(3) 2_655 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.824 _refine_diff_density_min -0.929 _refine_diff_density_rms 0.119 # SQUEEZE RESULTS # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.252 1011 525 ' ' 2 0.000 0.500 0.442 1011 524 ' ' _platon_squeeze_details ; ;