# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Raubenheimer, Helgard' _publ_contact_author_email hgr@sun.ac.za _publ_section_title ; Fischer-type tungsten acyl (carbeniate), carbene and carbyne complexes bearing C5-attached thiazolyl substituents: interaction with gold(I) fragments ; loop_ _publ_author_name S.Cronje H.Raubenheimer C.Strasser # Attachment '- CCDC710165.CIF' data_Compound-1b _database_code_depnum_ccdc_archive 'CCDC 710165' _audit_creation_method SHELXL-97 _chemical_name_systematic ;Tetramethylammonium pentacarbonyl[(2-phenylthiazol-5- yl)carbonyl]tungstate(1-) ; _chemical_name_common 'Tetramethylammonium pentacarbonyl((2-phenylthiazol-5- yl)carbonyl)tungstate(1-)' _chemical_melting_point 397 _chemical_formula_moiety 'C15 H6 N O6 S W, C4 H12 N' _chemical_formula_sum 'C19 H18 N2 O6 S W' _chemical_formula_weight 586.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_int_tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 12.602(1) _cell_length_b 19.3023(15) _cell_length_c 34.983(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 8509.6(12) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7986 _cell_measurement_theta_min 2.254 _cell_measurement_theta_max 26.400 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.830 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4544 _exptl_absorpt_coefficient_mu 5.565 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.548 _exptl_absorpt_correction_T_max 0.855 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 47050 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.40 _reflns_number_total 8711 _reflns_number_gt 7556 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material X-Seed _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^)+(0.0296P)^2^+3.7475P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8711 _refine_ls_number_parameters 531 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0309 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0572 _refine_ls_wR_factor_gt 0.0547 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 W1A W 0.011409(11) 0.208837(7) 0.103075(4) 0.01706(4) Uani 1 1 d . . . W1B W 0.434735(10) 0.405628(7) 0.201842(4) 0.01523(4) Uani 1 1 d . . . S1A S -0.07556(7) 0.37774(4) 0.00176(2) 0.01839(17) Uani 1 1 d . . . S1B S 0.81652(6) 0.42533(4) 0.17304(2) 0.01699(17) Uani 1 1 d . . . O1A O -0.0210(2) 0.23475(13) 0.01625(7) 0.0268(6) Uani 1 1 d . . . O1B O 0.6514(2) 0.32941(12) 0.19254(7) 0.0277(6) Uani 1 1 d . . . N1A N -0.1243(2) 0.44670(14) 0.06221(8) 0.0213(6) Uani 1 1 d . . . N1B N 0.7516(2) 0.54605(13) 0.15241(8) 0.0186(6) Uani 1 1 d . . . C1A C -0.0242(3) 0.26421(18) 0.04790(9) 0.0182(7) Uani 1 1 d . . . C1B C 0.6072(3) 0.38680(16) 0.18914(9) 0.0173(7) Uani 1 1 d . . . O2A O 0.0537(2) 0.12753(13) 0.17959(7) 0.0281(6) Uani 1 1 d . . . O2B O 0.19574(19) 0.42505(13) 0.22772(7) 0.0279(6) Uani 1 1 d . . . C2A C 0.0393(3) 0.15673(18) 0.15124(10) 0.0212(7) Uani 1 1 d . . . C2B C 0.2823(3) 0.41811(17) 0.21823(9) 0.0205(7) Uani 1 1 d . . . O3A O 0.1094(2) 0.33856(14) 0.14680(7) 0.0359(7) Uani 1 1 d . . . O3B O 0.50875(19) 0.53709(12) 0.24976(7) 0.0242(6) Uani 1 1 d . . . N3A N 0.0784(2) 0.14200(15) -0.05640(8) 0.0193(6) Uani 1 1 d . . . N3B N 0.7240(2) 0.17457(14) 0.23755(8) 0.0194(6) Uani 1 1 d . . . C3A C 0.0700(3) 0.29393(18) 0.13042(10) 0.0230(8) Uani 1 1 d . . . C3B C 0.4811(3) 0.49042(18) 0.23241(9) 0.0174(7) Uani 1 1 d . . . O4A O -0.2322(2) 0.24050(15) 0.11798(8) 0.0383(7) Uani 1 1 d . . . O4B O 0.39586(19) 0.49182(13) 0.12560(7) 0.0261(6) Uani 1 1 d . . . C4A C -0.1432(3) 0.22889(19) 0.11436(10) 0.0259(8) Uani 1 1 d . . . C4B C 0.4105(3) 0.46210(18) 0.15360(10) 0.0200(7) Uani 1 1 d . . . O5A O -0.0544(2) 0.06531(14) 0.06513(8) 0.0367(7) Uani 1 1 d . . . O5B O 0.3762(3) 0.27301(15) 0.15247(8) 0.0491(9) Uani 1 1 d . . . C5A C -0.0331(3) 0.11786(19) 0.07834(10) 0.0242(8) Uani 1 1 d . . . C5B C 0.3979(3) 0.32069(19) 0.17035(10) 0.0265(8) Uani 1 1 d . . . O6A O 0.2375(2) 0.19107(15) 0.06401(8) 0.0393(7) Uani 1 1 d . . . O6B O 0.4871(2) 0.30963(13) 0.27329(7) 0.0283(6) Uani 1 1 d . . . C6A C 0.1578(3) 0.19628(18) 0.07915(10) 0.0270(8) Uani 1 1 d . . . C6B C 0.4676(3) 0.34495(18) 0.24805(10) 0.0200(7) Uani 1 1 d . . . C10A C -0.0581(2) 0.33832(17) 0.04571(9) 0.0164(7) Uani 1 1 d . . . C10B C 0.6818(3) 0.44310(16) 0.17622(9) 0.0159(7) Uani 1 1 d . . . C11A C -0.0880(3) 0.38345(17) 0.07356(10) 0.0193(7) Uani 1 1 d . . . H11A H -0.0837 0.3714 0.0998 0.023 Uiso 1 1 calc R . . C11B C 0.6645(3) 0.50866(16) 0.16407(9) 0.0171(7) Uani 1 1 d . . . H11B H 0.5952 0.5280 0.1636 0.021 Uiso 1 1 calc R . . C12A C -0.1219(3) 0.45122(17) 0.02468(10) 0.0201(7) Uani 1 1 d . . . C12B C 0.8377(3) 0.50849(16) 0.15578(9) 0.0151(7) Uani 1 1 d . . . C13A C -0.1589(3) 0.51277(17) 0.00391(10) 0.0224(8) Uani 1 1 d . . . C13B C 0.9447(3) 0.53349(17) 0.14635(9) 0.0164(7) Uani 1 1 d . . . C14A C -0.1499(3) 0.5177(2) -0.03567(11) 0.0297(9) Uani 1 1 d . . . H14A H -0.1200 0.4805 -0.0498 0.036 Uiso 1 1 calc R . . C14B C 1.0349(3) 0.49927(19) 0.15925(10) 0.0218(8) Uani 1 1 d . . . H14B H 1.0279 0.4584 0.1742 0.026 Uiso 1 1 calc R . . C15A C -0.1847(3) 0.5771(2) -0.05450(13) 0.0373(10) Uani 1 1 d . . . H15A H -0.1778 0.5808 -0.0815 0.045 Uiso 1 1 calc R . . C15B C 1.1346(3) 0.5244(2) 0.15047(10) 0.0298(9) Uani 1 1 d . . . H15B H 1.1957 0.5008 0.1596 0.036 Uiso 1 1 calc R . . C16A C -0.2293(3) 0.6306(2) -0.03389(15) 0.0430(12) Uani 1 1 d . . . H16A H -0.2533 0.6709 -0.0468 0.052 Uiso 1 1 calc R . . C16B C 1.1464(3) 0.5831(2) 0.12860(11) 0.0304(9) Uani 1 1 d . . . H16B H 1.2153 0.5999 0.1227 0.037 Uiso 1 1 calc R . . C17A C -0.2392(3) 0.6259(2) 0.00534(14) 0.0387(10) Uani 1 1 d . . . H17A H -0.2698 0.6631 0.0193 0.046 Uiso 1 1 calc R . . C17B C 1.0571(3) 0.6178(2) 0.11522(11) 0.0281(9) Uani 1 1 d . . . H17B H 1.0648 0.6583 0.1000 0.034 Uiso 1 1 calc R . . C18A C -0.2047(3) 0.56730(19) 0.02421(12) 0.0294(9) Uani 1 1 d . . . H18A H -0.2123 0.5641 0.0512 0.035 Uiso 1 1 calc R . . C18B C 0.9565(3) 0.59304(17) 0.12417(10) 0.0217(8) Uani 1 1 d . . . H18B H 0.8955 0.6168 0.1151 0.026 Uiso 1 1 calc R . . C20A C -0.0008(3) 0.1919(3) -0.07097(12) 0.0443(12) Uani 1 1 d . . . H20A H 0.0335 0.2241 -0.0888 0.066 Uiso 1 1 calc R . . H20B H -0.0311 0.2179 -0.0495 0.066 Uiso 1 1 calc R . . H20C H -0.0574 0.1668 -0.0843 0.066 Uiso 1 1 calc R . . C20B C 0.7320(3) 0.22919(18) 0.26755(10) 0.0273(8) Uani 1 1 d . . . H20D H 0.8047 0.2307 0.2775 0.041 Uiso 1 1 calc R . . H20E H 0.6828 0.2185 0.2884 0.041 Uiso 1 1 calc R . . H20F H 0.7137 0.2743 0.2565 0.041 Uiso 1 1 calc R . . C21A C 0.1625(3) 0.1797(2) -0.03569(12) 0.0423(11) Uani 1 1 d . . . H21A H 0.2158 0.1468 -0.0264 0.063 Uiso 1 1 calc R . . H21B H 0.1313 0.2044 -0.0139 0.063 Uiso 1 1 calc R . . H21C H 0.1962 0.2131 -0.0529 0.063 Uiso 1 1 calc R . . C21B C 0.6138(3) 0.17435(18) 0.22137(10) 0.0235(8) Uani 1 1 d . . . H21D H 0.5992 0.2193 0.2094 0.035 Uiso 1 1 calc R . . H21E H 0.5626 0.1661 0.2419 0.035 Uiso 1 1 calc R . . H21F H 0.6078 0.1376 0.2022 0.035 Uiso 1 1 calc R . . C22A C 0.0248(4) 0.0930(2) -0.02943(14) 0.0464(12) Uani 1 1 d . . . H22A H -0.0306 0.0674 -0.0431 0.070 Uiso 1 1 calc R . . H22B H -0.0073 0.1193 -0.0084 0.070 Uiso 1 1 calc R . . H22C H 0.0771 0.0604 -0.0191 0.070 Uiso 1 1 calc R . . C22B C 0.8003(3) 0.19006(19) 0.20589(10) 0.0265(8) Uani 1 1 d . . . H22D H 0.7840 0.2356 0.1950 0.040 Uiso 1 1 calc R . . H22E H 0.7939 0.1545 0.1860 0.040 Uiso 1 1 calc R . . H22F H 0.8728 0.1902 0.2160 0.040 Uiso 1 1 calc R . . C23A C 0.1253(3) 0.1027(2) -0.08891(10) 0.0294(9) Uani 1 1 d . . . H23A H 0.1612 0.1349 -0.1063 0.044 Uiso 1 1 calc R . . H23B H 0.0689 0.0784 -0.1027 0.044 Uiso 1 1 calc R . . H23C H 0.1767 0.0690 -0.0791 0.044 Uiso 1 1 calc R . . C23B C 0.7482(3) 0.10482(18) 0.25450(10) 0.0263(8) Uani 1 1 d . . . H23D H 0.7422 0.0692 0.2347 0.040 Uiso 1 1 calc R . . H23E H 0.6978 0.0949 0.2751 0.040 Uiso 1 1 calc R . . H23F H 0.8206 0.1049 0.2648 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 W1A 0.01853(8) 0.01660(8) 0.01606(8) 0.00108(5) 0.00004(5) 0.00171(5) W1B 0.01435(7) 0.01492(7) 0.01644(7) -0.00053(5) 0.00275(5) -0.00147(5) S1A 0.0184(4) 0.0205(4) 0.0162(4) 0.0013(3) 0.0004(3) 0.0013(3) S1B 0.0151(4) 0.0160(4) 0.0199(4) 0.0020(3) 0.0029(3) 0.0024(3) O1A 0.0369(15) 0.0230(13) 0.0204(13) -0.0028(11) 0.0028(12) 0.0058(12) O1B 0.0270(14) 0.0145(12) 0.0416(15) 0.0042(11) 0.0125(12) 0.0037(11) N1A 0.0183(15) 0.0215(15) 0.0240(16) -0.0015(12) -0.0005(13) 0.0026(12) N1B 0.0165(14) 0.0161(14) 0.0232(15) -0.0006(11) 0.0014(12) 0.0007(12) C1A 0.0141(16) 0.0211(17) 0.0195(18) -0.0008(14) 0.0035(14) 0.0023(14) C1B 0.0196(17) 0.0162(17) 0.0161(16) 0.0018(13) 0.0005(14) -0.0018(14) O2A 0.0344(15) 0.0251(14) 0.0249(14) 0.0060(11) -0.0077(12) -0.0029(12) O2B 0.0178(13) 0.0403(15) 0.0257(14) 0.0050(11) 0.0026(11) 0.0016(12) C2A 0.0204(18) 0.0181(17) 0.025(2) -0.0008(15) -0.0022(15) -0.0016(14) C2B 0.0221(19) 0.0231(18) 0.0162(17) 0.0026(13) 0.0015(15) -0.0013(15) O3A 0.0487(18) 0.0266(15) 0.0323(15) -0.0026(12) -0.0064(14) -0.0026(13) O3B 0.0264(14) 0.0199(13) 0.0262(13) -0.0046(11) -0.0024(11) 0.0029(10) N3A 0.0166(14) 0.0261(16) 0.0153(14) -0.0036(12) 0.0011(12) 0.0018(12) N3B 0.0181(14) 0.0157(14) 0.0243(15) -0.0012(12) 0.0027(12) -0.0008(12) C3A 0.030(2) 0.0223(19) 0.0166(17) 0.0015(14) 0.0008(15) 0.0058(16) C3B 0.0142(17) 0.0209(18) 0.0171(17) 0.0011(14) 0.0024(13) 0.0044(14) O4A 0.0230(15) 0.0530(19) 0.0389(16) 0.0144(14) 0.0077(13) 0.0106(14) O4B 0.0195(13) 0.0353(15) 0.0235(14) 0.0087(11) 0.0018(11) 0.0001(11) C4A 0.029(2) 0.0253(19) 0.0231(19) 0.0088(15) 0.0019(16) 0.0034(16) C4B 0.0119(16) 0.0236(18) 0.0246(19) -0.0034(15) 0.0015(14) -0.0004(14) O5A 0.0480(18) 0.0247(15) 0.0375(16) -0.0043(13) -0.0141(14) -0.0014(13) O5B 0.075(2) 0.0355(16) 0.0365(17) -0.0135(14) 0.0227(17) -0.0272(16) C5A 0.0266(19) 0.026(2) 0.0200(18) 0.0045(15) -0.0085(16) 0.0027(16) C5B 0.034(2) 0.026(2) 0.0194(18) 0.0000(15) 0.0109(16) -0.0086(17) O6A 0.0288(16) 0.0495(18) 0.0397(17) 0.0112(14) 0.0103(14) 0.0165(14) O6B 0.0286(15) 0.0276(14) 0.0286(15) 0.0079(12) 0.0041(12) 0.0029(11) C6A 0.031(2) 0.0232(19) 0.026(2) 0.0062(15) -0.0021(17) 0.0102(16) C6B 0.0170(17) 0.0186(17) 0.0245(19) -0.0001(15) 0.0030(14) -0.0003(14) C10A 0.0123(16) 0.0206(17) 0.0162(16) 0.0002(13) -0.0006(13) -0.0014(13) C10B 0.0149(16) 0.0173(17) 0.0154(16) -0.0041(13) 0.0011(13) 0.0013(13) C11A 0.0177(17) 0.0220(18) 0.0180(17) -0.0018(14) -0.0011(14) 0.0020(14) C11B 0.0116(15) 0.0176(17) 0.0223(17) -0.0031(13) -0.0002(13) -0.0006(13) C12A 0.0155(17) 0.0198(17) 0.0251(18) -0.0008(14) 0.0017(15) -0.0003(14) C12B 0.0187(17) 0.0125(15) 0.0139(16) -0.0034(12) 0.0002(13) 0.0008(13) C13A 0.0148(17) 0.0195(18) 0.033(2) 0.0061(15) -0.0022(15) -0.0051(14) C13B 0.0171(17) 0.0180(17) 0.0142(16) -0.0026(13) 0.0009(13) -0.0008(13) C14A 0.0226(19) 0.028(2) 0.038(2) 0.0095(17) -0.0029(17) -0.0047(16) C14B 0.0197(17) 0.028(2) 0.0180(17) 0.0042(14) 0.0039(14) 0.0027(15) C15A 0.029(2) 0.037(2) 0.045(3) 0.0174(19) -0.008(2) -0.0057(19) C15B 0.0155(18) 0.042(2) 0.032(2) 0.0085(17) 0.0014(16) -0.0002(17) C16A 0.019(2) 0.028(2) 0.082(4) 0.027(2) -0.010(2) -0.0040(17) C16B 0.0161(18) 0.038(2) 0.037(2) 0.0079(17) 0.0039(17) -0.0047(16) C17A 0.023(2) 0.023(2) 0.070(3) 0.006(2) -0.003(2) 0.0010(17) C17B 0.028(2) 0.026(2) 0.031(2) 0.0097(16) 0.0041(17) -0.0048(16) C18A 0.0194(19) 0.0230(19) 0.046(2) 0.0061(17) 0.0021(18) -0.0021(16) C18B 0.0151(17) 0.0208(18) 0.029(2) 0.0038(15) 0.0001(15) 0.0004(14) C20A 0.043(3) 0.067(3) 0.023(2) 0.000(2) -0.0056(19) 0.028(2) C20B 0.030(2) 0.0262(19) 0.0259(19) -0.0116(16) 0.0044(17) -0.0068(16) C21A 0.022(2) 0.065(3) 0.040(2) -0.029(2) 0.0023(19) -0.009(2) C21B 0.0224(18) 0.0200(18) 0.028(2) 0.0009(15) -0.0001(16) -0.0017(15) C22A 0.062(3) 0.025(2) 0.052(3) -0.005(2) 0.030(3) -0.003(2) C22B 0.025(2) 0.027(2) 0.028(2) 0.0000(15) 0.0100(16) -0.0027(16) C23A 0.0207(19) 0.040(2) 0.027(2) -0.0154(17) 0.0022(16) 0.0030(17) C23B 0.026(2) 0.025(2) 0.028(2) 0.0061(15) 0.0063(16) 0.0062(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 W1A C2A 1.994(4) . ? W1A C4A 2.025(4) . ? W1A C5A 2.037(4) . ? W1A C3A 2.039(4) . ? W1A C6A 2.040(4) . ? W1A C1A 2.251(3) . ? W1B C2B 2.019(4) . ? W1B C5B 2.029(4) . ? W1B C4B 2.032(4) . ? W1B C6B 2.039(4) . ? W1B C3B 2.040(3) . ? W1B C1B 2.248(3) . ? S1A C10A 1.730(3) . ? S1A C12A 1.731(3) . ? S1B C10B 1.735(3) . ? S1B C12B 1.735(3) . ? O1A C1A 1.245(4) . ? O1B C1B 1.246(4) . ? N1A C12A 1.316(4) . ? N1A C11A 1.363(4) . ? N1B C12B 1.311(4) . ? N1B C11B 1.375(4) . ? C1A C10A 1.495(5) . ? C1B C10B 1.507(4) . ? O2A C2A 1.155(4) . ? O2B C2B 1.148(4) . ? O3A C3A 1.148(4) . ? O3B C3B 1.141(4) . ? N3A C21A 1.476(4) . ? N3A C20A 1.478(5) . ? N3A C23A 1.489(4) . ? N3A C22A 1.497(5) . ? N3B C20B 1.491(4) . ? N3B C22B 1.497(4) . ? N3B C21B 1.499(4) . ? N3B C23B 1.502(4) . ? O4A C4A 1.151(4) . ? O4B C4B 1.150(4) . ? O5A C5A 1.146(4) . ? O5B C5B 1.146(4) . ? O6A C6A 1.140(4) . ? O6B C6B 1.142(4) . ? C10A C11A 1.360(5) . ? C10B C11B 1.353(4) . ? C11A H11A 0.9500 . ? C11B H11B 0.9500 . ? C12A C13A 1.468(5) . ? C12B C13B 1.470(4) . ? C13A C14A 1.392(5) . ? C13A C18A 1.395(5) . ? C13B C14B 1.390(5) . ? C13B C18B 1.395(5) . ? C14A C15A 1.394(5) . ? C14A H14A 0.9500 . ? C14B C15B 1.382(5) . ? C14B H14B 0.9500 . ? C15A C16A 1.378(6) . ? C15A H15A 0.9500 . ? C15B C16B 1.376(5) . ? C15B H15B 0.9500 . ? C16A C17A 1.381(6) . ? C16A H16A 0.9500 . ? C16B C17B 1.391(5) . ? C16B H16B 0.9500 . ? C17A C18A 1.380(5) . ? C17A H17A 0.9500 . ? C17B C18B 1.391(5) . ? C17B H17B 0.9500 . ? C18A H18A 0.9500 . ? C18B H18B 0.9500 . ? C20A H20A 0.9800 . ? C20A H20B 0.9800 . ? C20A H20C 0.9800 . ? C20B H20D 0.9800 . ? C20B H20E 0.9800 . ? C20B H20F 0.9800 . ? C21A H21A 0.9800 . ? C21A H21B 0.9800 . ? C21A H21C 0.9800 . ? C21B H21D 0.9800 . ? C21B H21E 0.9800 . ? C21B H21F 0.9800 . ? C22A H22A 0.9800 . ? C22A H22B 0.9800 . ? C22A H22C 0.9800 . ? C22B H22D 0.9800 . ? C22B H22E 0.9800 . ? C22B H22F 0.9800 . ? 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 C2A W1A C4A 95.82(14) . . ? C2A W1A C5A 88.44(14) . . ? C4A W1A C5A 89.00(15) . . ? C2A W1A C3A 86.90(14) . . ? C4A W1A C3A 95.92(15) . . ? C5A W1A C3A 173.54(14) . . ? C2A W1A C6A 97.32(14) . . ? C4A W1A C6A 166.53(14) . . ? C5A W1A C6A 88.40(15) . . ? C3A W1A C6A 87.75(15) . . ? C2A W1A C1A 177.74(13) . . ? C4A W1A C1A 83.37(13) . . ? C5A W1A C1A 89.43(13) . . ? C3A W1A C1A 95.28(13) . . ? C6A W1A C1A 83.39(13) . . ? C2B W1B C5B 91.88(14) . . ? C2B W1B C4B 91.66(13) . . ? C5B W1B C4B 87.02(14) . . ? C2B W1B C6B 92.09(13) . . ? C5B W1B C6B 90.74(14) . . ? C4B W1B C6B 175.69(13) . . ? C2B W1B C3B 91.58(13) . . ? C5B W1B C3B 176.53(14) . . ? C4B W1B C3B 92.75(13) . . ? C6B W1B C3B 89.27(13) . . ? C2B W1B C1B 174.42(12) . . ? C5B W1B C1B 89.05(14) . . ? C4B W1B C1B 93.89(12) . . ? C6B W1B C1B 82.39(13) . . ? C3B W1B C1B 87.52(12) . . ? C10A S1A C12A 89.52(16) . . ? C10B S1B C12B 89.41(15) . . ? C12A N1A C11A 110.0(3) . . ? C12B N1B C11B 110.1(3) . . ? O1A C1A C10A 113.6(3) . . ? O1A C1A W1A 122.6(2) . . ? C10A C1A W1A 123.7(2) . . ? O1B C1B C10B 113.0(3) . . ? O1B C1B W1B 123.9(2) . . ? C10B C1B W1B 123.1(2) . . ? O2A C2A W1A 178.3(3) . . ? O2B C2B W1B 179.7(3) . . ? C21A N3A C20A 109.4(3) . . ? C21A N3A C23A 110.0(3) . . ? C20A N3A C23A 109.7(3) . . ? C21A N3A C22A 109.0(3) . . ? C20A N3A C22A 108.9(3) . . ? C23A N3A C22A 109.8(3) . . ? C20B N3B C22B 109.6(3) . . ? C20B N3B C21B 109.3(3) . . ? C22B N3B C21B 108.4(3) . . ? C20B N3B C23B 110.0(3) . . ? C22B N3B C23B 109.9(3) . . ? C21B N3B C23B 109.6(3) . . ? O3A C3A W1A 174.6(3) . . ? O3B C3B W1B 178.6(3) . . ? O4A C4A W1A 175.1(3) . . ? O4B C4B W1B 177.5(3) . . ? O5A C5A W1A 177.0(3) . . ? O5B C5B W1B 179.4(4) . . ? O6A C6A W1A 176.2(3) . . ? O6B C6B W1B 178.2(3) . . ? C11A C10A C1A 130.9(3) . . ? C11A C10A S1A 108.6(2) . . ? C1A C10A S1A 120.2(2) . . ? C11B C10B C1B 131.9(3) . . ? C11B C10B S1B 108.8(2) . . ? C1B C10B S1B 119.2(2) . . ? C10A C11A N1A 117.3(3) . . ? C10A C11A H11A 121.4 . . ? N1A C11A H11A 121.4 . . ? C10B C11B N1B 117.1(3) . . ? C10B C11B H11B 121.4 . . ? N1B C11B H11B 121.4 . . ? N1A C12A C13A 122.7(3) . . ? N1A C12A S1A 114.6(3) . . ? C13A C12A S1A 122.7(3) . . ? N1B C12B C13B 123.9(3) . . ? N1B C12B S1B 114.6(2) . . ? C13B C12B S1B 121.5(2) . . ? C14A C13A C18A 119.2(3) . . ? C14A C13A C12A 121.4(3) . . ? C18A C13A C12A 119.3(3) . . ? C14B C13B C18B 119.0(3) . . ? C14B C13B C12B 121.4(3) . . ? C18B C13B C12B 119.6(3) . . ? C13A C14A C15A 120.0(4) . . ? C13A C14A H14A 120.0 . . ? C15A C14A H14A 120.0 . . ? C15B C14B C13B 120.3(3) . . ? C15B C14B H14B 119.8 . . ? C13B C14B H14B 119.8 . . ? C16A C15A C14A 119.8(4) . . ? C16A C15A H15A 120.1 . . ? C14A C15A H15A 120.1 . . ? C16B C15B C14B 120.7(4) . . ? C16B C15B H15B 119.6 . . ? C14B C15B H15B 119.6 . . ? C15A C16A C17A 120.6(4) . . ? C15A C16A H16A 119.7 . . ? C17A C16A H16A 119.7 . . ? C15B C16B C17B 119.8(3) . . ? C15B C16B H16B 120.1 . . ? C17B C16B H16B 120.1 . . ? C18A C17A C16A 120.0(4) . . ? C18A C17A H17A 120.0 . . ? C16A C17A H17A 120.0 . . ? C18B C17B C16B 119.7(3) . . ? C18B C17B H17B 120.1 . . ? C16B C17B H17B 120.1 . . ? C17A C18A C13A 120.4(4) . . ? C17A C18A H18A 119.8 . . ? C13A C18A H18A 119.8 . . ? C17B C18B C13B 120.4(3) . . ? C17B C18B H18B 119.8 . . ? C13B C18B H18B 119.8 . . ? N3A C20A H20A 109.5 . . ? N3A C20A H20B 109.5 . . ? H20A C20A H20B 109.5 . . ? N3A C20A H20C 109.5 . . ? H20A C20A H20C 109.5 . . ? H20B C20A H20C 109.5 . . ? N3B C20B H20D 109.5 . . ? N3B C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? N3B C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? N3A C21A H21A 109.5 . . ? N3A C21A H21B 109.5 . . ? H21A C21A H21B 109.5 . . ? N3A C21A H21C 109.5 . . ? H21A C21A H21C 109.5 . . ? H21B C21A H21C 109.5 . . ? N3B C21B H21D 109.5 . . ? N3B C21B H21E 109.5 . . ? H21D C21B H21E 109.5 . . ? N3B C21B H21F 109.5 . . ? H21D C21B H21F 109.5 . . ? H21E C21B H21F 109.5 . . ? N3A C22A H22A 109.5 . . ? N3A C22A H22B 109.5 . . ? H22A C22A H22B 109.5 . . ? N3A C22A H22C 109.5 . . ? H22A C22A H22C 109.5 . . ? H22B C22A H22C 109.5 . . ? N3B C22B H22D 109.5 . . ? N3B C22B H22E 109.5 . . ? H22D C22B H22E 109.5 . . ? N3B C22B H22F 109.5 . . ? H22D C22B H22F 109.5 . . ? H22E C22B H22F 109.5 . . ? N3A C23A H23A 109.5 . . ? N3A C23A H23B 109.5 . . ? H23A C23A H23B 109.5 . . ? N3A C23A H23C 109.5 . . ? H23A C23A H23C 109.5 . . ? H23B C23A H23C 109.5 . . ? N3B C23B H23D 109.5 . . ? N3B C23B H23E 109.5 . . ? H23D C23B H23E 109.5 . . ? N3B C23B H23F 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 C4A W1A C1A O1A -115.0(3) . . . . ? C5A W1A C1A O1A -26.0(3) . . . . ? C3A W1A C1A O1A 149.6(3) . . . . ? C6A W1A C1A O1A 62.5(3) . . . . ? C4A W1A C1A C10A 62.3(3) . . . . ? C5A W1A C1A C10A 151.4(3) . . . . ? C3A W1A C1A C10A -33.0(3) . . . . ? C6A W1A C1A C10A -120.1(3) . . . . ? C5B W1B C1B O1B -48.0(3) . . . . ? C4B W1B C1B O1B -135.0(3) . . . . ? C6B W1B C1B O1B 42.8(3) . . . . ? C3B W1B C1B O1B 132.4(3) . . . . ? C5B W1B C1B C10B 133.1(3) . . . . ? C4B W1B C1B C10B 46.1(3) . . . . ? C6B W1B C1B C10B -136.1(3) . . . . ? C3B W1B C1B C10B -46.5(3) . . . . ? O1A C1A C10A C11A 167.5(3) . . . . ? W1A C1A C10A C11A -10.1(5) . . . . ? O1A C1A C10A S1A -6.5(4) . . . . ? W1A C1A C10A S1A 175.93(16) . . . . ? C12A S1A C10A C11A -0.2(3) . . . . ? C12A S1A C10A C1A 175.0(3) . . . . ? O1B C1B C10B C11B 169.3(3) . . . . ? W1B C1B C10B C11B -11.7(5) . . . . ? O1B C1B C10B S1B -7.1(4) . . . . ? W1B C1B C10B S1B 171.92(16) . . . . ? C12B S1B C10B C11B 0.3(2) . . . . ? C12B S1B C10B C1B 177.5(3) . . . . ? C1A C10A C11A N1A -174.1(3) . . . . ? S1A C10A C11A N1A 0.4(4) . . . . ? C12A N1A C11A C10A -0.5(4) . . . . ? C1B C10B C11B N1B -176.8(3) . . . . ? S1B C10B C11B N1B -0.2(4) . . . . ? C12B N1B C11B C10B -0.2(4) . . . . ? C11A N1A C12A C13A 178.4(3) . . . . ? C11A N1A C12A S1A 0.3(4) . . . . ? C10A S1A C12A N1A -0.1(3) . . . . ? C10A S1A C12A C13A -178.2(3) . . . . ? C11B N1B C12B C13B -178.9(3) . . . . ? C11B N1B C12B S1B 0.4(3) . . . . ? C10B S1B C12B N1B -0.5(3) . . . . ? C10B S1B C12B C13B 178.9(3) . . . . ? N1A C12A C13A C14A 176.3(3) . . . . ? S1A C12A C13A C14A -5.7(5) . . . . ? N1A C12A C13A C18A -4.2(5) . . . . ? S1A C12A C13A C18A 173.8(3) . . . . ? N1B C12B C13B C14B 163.4(3) . . . . ? S1B C12B C13B C14B -16.0(4) . . . . ? N1B C12B C13B C18B -16.3(5) . . . . ? S1B C12B C13B C18B 164.4(3) . . . . ? C18A C13A C14A C15A 1.2(5) . . . . ? C12A C13A C14A C15A -179.3(3) . . . . ? C18B C13B C14B C15B 0.6(5) . . . . ? C12B C13B C14B C15B -179.0(3) . . . . ? C13A C14A C15A C16A -0.9(6) . . . . ? C13B C14B C15B C16B -0.6(6) . . . . ? C14A C15A C16A C17A 0.4(6) . . . . ? C14B C15B C16B C17B 0.2(6) . . . . ? C15A C16A C17A C18A -0.2(6) . . . . ? C15B C16B C17B C18B 0.2(6) . . . . ? C16A C17A C18A C13A 0.6(6) . . . . ? C14A C13A C18A C17A -1.0(5) . . . . ? C12A C13A C18A C17A 179.5(3) . . . . ? C16B C17B C18B C13B -0.2(6) . . . . ? C14B C13B C18B C17B -0.2(5) . . . . ? C12B C13B C18B C17B 179.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.606 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.120 #===END # Attachment '- CCDC710167.CIF' data_Compound-2 _database_code_depnum_ccdc_archive 'CCDC 710167' _audit_creation_method SHELXL-97 _chemical_name_systematic ;pentacarbonyl-2\k^5^C-[\m-(2-phenylthiazol-5-yl)carbonyl- 1\kC:2\kO](triphenylphosphane-1\kP)goldtungsten pentane solvate ; _chemical_name_common ; pentacarbonyl-2kappa$5!C-(mu-(2-phenylthiazol-5-yl)carbonyl- 1kappaC:2kappaO)(triphenylphosphane-1kappaP)goldtungsten pentane solvate ; _chemical_melting_point 363 _chemical_formula_moiety 'C33 H21 Au N O6 P S W, C5 H12' _chemical_formula_sum 'C38 H33 Au N O6 P S W' _chemical_formula_weight 1043.5 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.5111(7) _cell_length_b 12.0437(8) _cell_length_c 13.8342(9) _cell_angle_alpha 100.005(1) _cell_angle_beta 102.850(1) _cell_angle_gamma 94.026(1) _cell_volume 1829.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6760 _cell_measurement_theta_min 2.529 _cell_measurement_theta_max 26.399 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.894 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 7.293 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.462 _exptl_absorpt_correction_T_max 0.598 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19796 _diffrn_reflns_av_R_equivalents 0.0346 _diffrn_reflns_av_sigmaI/netI 0.0434 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _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 1.73 _diffrn_reflns_theta_max 26.42 _reflns_number_total 7474 _reflns_number_gt 6485 _reflns_threshold_expression >2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 2001)' _computing_publication_material X-Seed _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. The geometry of the pentane molecule refined unsatisfactorily and was renstrained using SADI commands for the CH~3~---CH~2~ and CH~2~---CH~2~ bonds, respectively. ; _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^)+(0.0309P)^2^+11.7778P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7474 _refine_ls_number_parameters 444 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0397 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0870 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.075 _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 0.31470(2) 0.65777(2) 0.352182(19) 0.01894(8) Uani 1 1 d . . . W1 W 0.58591(2) 0.61859(2) 0.22099(2) 0.02605(9) Uani 1 1 d . . . S1 S 0.17095(15) 0.40425(14) 0.04475(13) 0.0230(3) Uani 1 1 d . . . P1 P 0.29536(14) 0.76046(14) 0.50321(13) 0.0182(3) Uani 1 1 d . . . O1 O 0.3964(4) 0.5452(4) 0.1739(4) 0.0258(11) Uani 1 1 d . . . O2 O 0.8553(5) 0.7143(6) 0.2682(4) 0.0449(15) Uani 1 1 d . . . O3 O 0.6432(5) 0.5756(5) 0.4450(4) 0.0352(12) Uani 1 1 d . . . O4 O 0.5374(5) 0.8707(5) 0.3003(4) 0.0363(13) Uani 1 1 d . . . O5 O 0.5694(5) 0.6820(6) 0.0056(4) 0.0499(16) Uani 1 1 d . . . O6 O 0.6628(5) 0.3744(6) 0.1505(5) 0.0496(16) Uani 1 1 d . . . N1 N -0.0075(5) 0.4324(5) 0.1269(4) 0.0243(12) Uani 1 1 d . . . C1 C 0.3109(6) 0.5579(6) 0.2150(5) 0.0229(14) Uani 1 1 d . . . C2 C 0.7546(7) 0.6792(7) 0.2505(6) 0.0322(17) Uani 1 1 d . . . C3 C 0.6163(6) 0.5886(6) 0.3628(6) 0.0300(16) Uani 1 1 d . . . C4 C 0.5499(6) 0.7777(7) 0.2716(6) 0.0293(16) Uani 1 1 d . . . C5 C 0.5705(6) 0.6564(7) 0.0805(6) 0.0315(17) Uani 1 1 d . . . C6 C 0.6325(7) 0.4607(7) 0.1749(6) 0.0353(18) Uani 1 1 d . . . C10 C 0.1952(6) 0.4946(5) 0.1608(5) 0.0195(13) Uani 1 1 d . . . C11 C 0.0896(6) 0.4971(6) 0.1900(5) 0.0223(14) Uani 1 1 d . . . H11 H 0.0845 0.5424 0.2521 0.027 Uiso 1 1 calc R . . C12 C 0.0210(6) 0.3770(5) 0.0465(5) 0.0202(14) Uani 1 1 d . . . C13 C -0.0663(6) 0.3006(6) -0.0340(5) 0.0223(14) Uani 1 1 d . . . C14 C -0.0366(6) 0.2496(6) -0.1224(5) 0.0274(15) Uani 1 1 d . . . H14 H 0.0418 0.2654 -0.1316 0.033 Uiso 1 1 calc R . . C15 C -0.1221(7) 0.1754(6) -0.1974(5) 0.0301(16) Uani 1 1 d . . . H15 H -0.1017 0.1408 -0.2576 0.036 Uiso 1 1 calc R . . C16 C -0.2359(7) 0.1520(7) -0.1848(6) 0.0359(18) Uani 1 1 d . . . H16 H -0.2936 0.1007 -0.2358 0.043 Uiso 1 1 calc R . . C17 C -0.2663(7) 0.2035(7) -0.0971(6) 0.0315(17) Uani 1 1 d . . . H17 H -0.3451 0.1881 -0.0886 0.038 Uiso 1 1 calc R . . C18 C -0.1821(6) 0.2768(6) -0.0226(5) 0.0283(16) Uani 1 1 d . . . H18 H -0.2033 0.3114 0.0373 0.034 Uiso 1 1 calc R . . C21 C 0.3293(12) 1.0189(13) 0.9296(10) 0.096(4) Uani 1 1 d D . . H21A H 0.2996 1.0193 0.9907 0.144 Uiso 1 1 calc R . . H21B H 0.3987 1.0764 0.9441 0.144 Uiso 1 1 calc R . . H21C H 0.3533 0.9439 0.9076 0.144 Uiso 1 1 calc R . . C22 C 0.2327(11) 1.0447(12) 0.8479(10) 0.085(4) Uani 1 1 d D . . H22A H 0.2126 1.1217 0.8718 0.103 Uiso 1 1 calc R . . H22B H 0.2675 1.0489 0.7891 0.103 Uiso 1 1 calc R . . C23 C 0.1187(12) 0.9693(11) 0.8102(15) 0.113(6) Uani 1 1 d D . . H23A H 0.0668 1.0011 0.7570 0.136 Uiso 1 1 calc R . . H23B H 0.1365 0.8946 0.7777 0.136 Uiso 1 1 calc R . . C24 C 0.0509(12) 0.9506(10) 0.8833(11) 0.094(5) Uani 1 1 d D . . H24A H 0.0328 1.0243 0.9177 0.113 Uiso 1 1 calc R . . H24B H 0.0990 0.9141 0.9351 0.113 Uiso 1 1 calc R . . C25 C -0.0691(10) 0.8729(9) 0.8295(11) 0.082(4) Uani 1 1 d D . . H25A H -0.1101 0.9026 0.7710 0.123 Uiso 1 1 calc R . . H25B H -0.1208 0.8720 0.8769 0.123 Uiso 1 1 calc R . . H25C H -0.0514 0.7956 0.8069 0.123 Uiso 1 1 calc R . . C111 C 0.4213(6) 0.7668(6) 0.6111(5) 0.0231(14) Uani 1 1 d . . . C112 C 0.4404(6) 0.8511(6) 0.6963(6) 0.0297(16) Uani 1 1 d . . . H112 H 0.3887 0.9091 0.6983 0.036 Uiso 1 1 calc R . . C113 C 0.5343(7) 0.8519(7) 0.7791(6) 0.0366(19) Uani 1 1 d . . . H113 H 0.5471 0.9097 0.8379 0.044 Uiso 1 1 calc R . . C114 C 0.6090(8) 0.7667(8) 0.7745(7) 0.046(2) Uani 1 1 d . . . H114 H 0.6739 0.7664 0.8305 0.055 Uiso 1 1 calc R . . C115 C 0.5907(7) 0.6836(7) 0.6907(7) 0.039(2) Uani 1 1 d . . . H115 H 0.6425 0.6257 0.6889 0.047 Uiso 1 1 calc R . . C116 C 0.4966(6) 0.6828(6) 0.6079(6) 0.0315(17) Uani 1 1 d . . . H116 H 0.4843 0.6247 0.5494 0.038 Uiso 1 1 calc R . . C121 C 0.2693(5) 0.9066(5) 0.4973(5) 0.0184(13) Uani 1 1 d . . . C122 C 0.1824(6) 0.9589(6) 0.5378(5) 0.0269(15) Uani 1 1 d . . . H122 H 0.1354 0.9191 0.5720 0.032 Uiso 1 1 calc R . . C123 C 0.1646(7) 1.0696(6) 0.5282(6) 0.0340(18) Uani 1 1 d . . . H123 H 0.1056 1.1059 0.5561 0.041 Uiso 1 1 calc R . . C124 C 0.2325(6) 1.1268(6) 0.4781(6) 0.0309(17) Uani 1 1 d . . . H124 H 0.2192 1.2022 0.4708 0.037 Uiso 1 1 calc R . . C125 C 0.3192(6) 1.0758(6) 0.4385(5) 0.0277(16) Uani 1 1 d . . . H125 H 0.3657 1.1158 0.4041 0.033 Uiso 1 1 calc R . . C126 C 0.3388(6) 0.9657(5) 0.4489(5) 0.0208(14) Uani 1 1 d . . . H126 H 0.4000 0.9308 0.4229 0.025 Uiso 1 1 calc R . . C131 C 0.1643(5) 0.7011(5) 0.5372(5) 0.0195(13) Uani 1 1 d . . . C132 C 0.0571(6) 0.6814(6) 0.4664(5) 0.0250(15) Uani 1 1 d . . . H132 H 0.0532 0.6954 0.4004 0.030 Uiso 1 1 calc R . . C133 C -0.0474(6) 0.6403(6) 0.4920(6) 0.0279(16) Uani 1 1 d . . . H133 H -0.1223 0.6283 0.4438 0.033 Uiso 1 1 calc R . . C134 C -0.0406(6) 0.6177(6) 0.5871(6) 0.0292(16) Uani 1 1 d . . . H134 H -0.1112 0.5900 0.6043 0.035 Uiso 1 1 calc R . . C135 C 0.0675(7) 0.6347(6) 0.6575(6) 0.0314(17) Uani 1 1 d . . . H135 H 0.0719 0.6179 0.7228 0.038 Uiso 1 1 calc R . . C136 C 0.1705(6) 0.6766(6) 0.6325(5) 0.0273(15) Uani 1 1 d . . . H136 H 0.2453 0.6886 0.6809 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.01681(13) 0.01632(13) 0.02511(14) 0.00397(10) 0.00785(10) 0.00244(9) W1 0.01838(15) 0.03233(17) 0.02676(16) 0.00259(12) 0.00680(12) 0.00166(12) S1 0.0202(8) 0.0246(9) 0.0257(9) 0.0041(7) 0.0084(7) 0.0041(7) P1 0.0143(8) 0.0166(8) 0.0242(9) 0.0054(7) 0.0051(7) 0.0005(6) O1 0.020(2) 0.026(3) 0.030(3) 0.000(2) 0.007(2) 0.003(2) O2 0.022(3) 0.074(4) 0.040(3) 0.017(3) 0.009(2) -0.002(3) O3 0.028(3) 0.042(3) 0.035(3) 0.009(3) 0.006(2) -0.001(2) O4 0.031(3) 0.034(3) 0.043(3) 0.003(3) 0.013(3) 0.000(2) O5 0.044(4) 0.075(5) 0.031(3) 0.013(3) 0.008(3) 0.007(3) O6 0.045(4) 0.057(4) 0.047(4) 0.003(3) 0.011(3) 0.022(3) N1 0.027(3) 0.025(3) 0.025(3) 0.008(2) 0.011(2) 0.002(2) C1 0.022(3) 0.021(3) 0.028(4) 0.007(3) 0.007(3) 0.006(3) C2 0.026(4) 0.047(5) 0.026(4) 0.010(3) 0.009(3) 0.001(3) C3 0.025(4) 0.028(4) 0.037(4) 0.003(3) 0.012(3) 0.000(3) C4 0.021(4) 0.037(4) 0.030(4) 0.006(3) 0.007(3) 0.003(3) C5 0.021(4) 0.043(5) 0.030(4) 0.007(3) 0.006(3) 0.002(3) C6 0.028(4) 0.044(5) 0.035(4) 0.002(4) 0.009(3) 0.018(4) C10 0.022(3) 0.015(3) 0.024(3) 0.008(3) 0.007(3) 0.006(3) C11 0.025(4) 0.022(3) 0.024(3) 0.006(3) 0.011(3) 0.006(3) C12 0.021(3) 0.021(3) 0.022(3) 0.012(3) 0.005(3) 0.004(3) C13 0.024(3) 0.024(3) 0.024(3) 0.013(3) 0.009(3) 0.008(3) C14 0.025(4) 0.029(4) 0.027(4) 0.009(3) 0.001(3) 0.005(3) C15 0.037(4) 0.030(4) 0.022(4) 0.005(3) 0.003(3) 0.011(3) C16 0.032(4) 0.033(4) 0.033(4) 0.007(3) -0.010(3) 0.002(3) C17 0.024(4) 0.040(4) 0.031(4) 0.012(3) 0.005(3) 0.004(3) C18 0.024(4) 0.034(4) 0.027(4) 0.006(3) 0.004(3) 0.004(3) C21 0.083(10) 0.105(11) 0.094(10) 0.034(9) -0.003(8) 0.009(8) C22 0.066(8) 0.106(11) 0.090(10) 0.029(8) 0.022(7) 0.018(8) C23 0.094(11) 0.062(8) 0.213(19) 0.021(10) 0.094(12) 0.029(8) C24 0.105(11) 0.056(7) 0.123(12) 0.041(8) 0.009(9) 0.022(7) C25 0.057(7) 0.057(7) 0.138(12) 0.042(8) 0.017(7) 0.007(6) C111 0.018(3) 0.025(4) 0.027(4) 0.014(3) 0.003(3) -0.002(3) C112 0.024(4) 0.029(4) 0.036(4) 0.007(3) 0.007(3) 0.001(3) C113 0.027(4) 0.047(5) 0.032(4) 0.012(4) -0.001(3) -0.007(4) C114 0.033(5) 0.066(6) 0.039(5) 0.031(5) -0.004(4) 0.002(4) C115 0.025(4) 0.046(5) 0.053(5) 0.033(4) 0.004(4) 0.011(4) C116 0.029(4) 0.025(4) 0.043(5) 0.015(3) 0.008(3) 0.001(3) C121 0.015(3) 0.018(3) 0.020(3) 0.002(3) 0.002(3) -0.001(2) C122 0.023(4) 0.027(4) 0.034(4) 0.011(3) 0.010(3) 0.006(3) C123 0.025(4) 0.028(4) 0.050(5) 0.003(3) 0.011(4) 0.009(3) C124 0.025(4) 0.022(4) 0.043(4) 0.006(3) 0.003(3) -0.001(3) C125 0.028(4) 0.024(4) 0.030(4) 0.007(3) 0.005(3) -0.006(3) C126 0.019(3) 0.022(3) 0.019(3) 0.002(3) 0.002(3) 0.000(3) C131 0.015(3) 0.015(3) 0.029(4) 0.007(3) 0.004(3) 0.003(2) C132 0.026(4) 0.021(3) 0.031(4) 0.002(3) 0.015(3) 0.008(3) C133 0.022(4) 0.021(3) 0.042(4) 0.005(3) 0.011(3) 0.005(3) C134 0.020(4) 0.026(4) 0.044(4) 0.004(3) 0.019(3) -0.001(3) C135 0.030(4) 0.037(4) 0.031(4) 0.010(3) 0.015(3) -0.003(3) C136 0.024(4) 0.031(4) 0.028(4) 0.009(3) 0.008(3) -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 C1 2.053(7) . ? Au1 P1 2.3005(17) . ? W1 C2 1.953(7) . ? W1 C3 2.015(8) . ? W1 C4 2.027(8) . ? W1 C5 2.045(8) . ? W1 C6 2.045(8) . ? W1 O1 2.205(5) . ? S1 C10 1.729(7) . ? S1 C12 1.740(7) . ? P1 C131 1.813(7) . ? P1 C121 1.819(7) . ? P1 C111 1.821(7) . ? O1 C1 1.247(8) . ? O2 C2 1.162(9) . ? O3 C3 1.152(9) . ? O4 C4 1.152(9) . ? O5 C5 1.130(9) . ? O6 C6 1.140(9) . ? N1 C12 1.314(9) . ? N1 C11 1.351(9) . ? C1 C10 1.460(9) . ? C10 C11 1.365(9) . ? C11 H11 0.9500 . ? C12 C13 1.453(9) . ? C13 C18 1.393(9) . ? C13 C14 1.395(10) . ? C14 C15 1.394(10) . ? C14 H14 0.9500 . ? C15 C16 1.376(11) . ? C15 H15 0.9500 . ? C16 C17 1.392(11) . ? C16 H16 0.9500 . ? C17 C18 1.379(10) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C21 C22 1.491(14) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.477(15) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.445(15) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.567(14) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C111 C116 1.380(10) . ? C111 C112 1.381(10) . ? C112 C113 1.387(10) . ? C112 H112 0.9500 . ? C113 C114 1.387(12) . ? C113 H113 0.9500 . ? C114 C115 1.359(13) . ? C114 H114 0.9500 . ? C115 C116 1.388(11) . ? C115 H115 0.9500 . ? C116 H116 0.9500 . ? C121 C126 1.385(9) . ? C121 C122 1.388(9) . ? C122 C123 1.388(10) . ? C122 H122 0.9500 . ? C123 C124 1.377(11) . ? C123 H123 0.9500 . ? C124 C125 1.374(10) . ? C124 H124 0.9500 . ? C125 C126 1.387(9) . ? C125 H125 0.9500 . ? C126 H126 0.9500 . ? C131 C132 1.371(9) . ? C131 C136 1.388(9) . ? C132 C133 1.408(10) . ? C132 H132 0.9500 . ? C133 C134 1.375(10) . ? C133 H133 0.9500 . ? C134 C135 1.378(10) . ? C134 H134 0.9500 . ? C135 C136 1.393(10) . ? C135 H135 0.9500 . ? C136 H136 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 C1 Au1 P1 173.08(19) . . ? C2 W1 C3 87.9(3) . . ? C2 W1 C4 87.8(3) . . ? C3 W1 C4 90.1(3) . . ? C2 W1 C5 87.0(3) . . ? C3 W1 C5 174.8(3) . . ? C4 W1 C5 89.1(3) . . ? C2 W1 C6 89.0(3) . . ? C3 W1 C6 88.5(3) . . ? C4 W1 C6 176.6(3) . . ? C5 W1 C6 92.0(3) . . ? C2 W1 O1 175.0(2) . . ? C3 W1 O1 96.4(2) . . ? C4 W1 O1 94.8(2) . . ? C5 W1 O1 88.8(2) . . ? C6 W1 O1 88.4(3) . . ? C10 S1 C12 89.2(3) . . ? C131 P1 C121 104.5(3) . . ? C131 P1 C111 106.3(3) . . ? C121 P1 C111 106.3(3) . . ? C131 P1 Au1 110.1(2) . . ? C121 P1 Au1 113.1(2) . . ? C111 P1 Au1 115.7(2) . . ? C1 O1 W1 132.1(4) . . ? C12 N1 C11 110.6(6) . . ? O1 C1 C10 117.1(6) . . ? O1 C1 Au1 127.1(5) . . ? C10 C1 Au1 115.8(5) . . ? O2 C2 W1 179.4(7) . . ? O3 C3 W1 174.3(6) . . ? O4 C4 W1 175.2(6) . . ? O5 C5 W1 175.2(7) . . ? O6 C6 W1 177.4(7) . . ? C11 C10 C1 127.3(6) . . ? C11 C10 S1 108.7(5) . . ? C1 C10 S1 124.0(5) . . ? N1 C11 C10 117.2(6) . . ? N1 C11 H11 121.4 . . ? C10 C11 H11 121.4 . . ? N1 C12 C13 122.3(6) . . ? N1 C12 S1 114.2(5) . . ? C13 C12 S1 123.4(5) . . ? C18 C13 C14 119.0(7) . . ? C18 C13 C12 119.5(6) . . ? C14 C13 C12 121.5(6) . . ? C15 C14 C13 120.0(7) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C14 120.4(7) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 119.8(7) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C18 C17 C16 120.0(7) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C13 120.7(7) . . ? C17 C18 H18 119.6 . . ? C13 C18 H18 119.6 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 C21 120.4(13) . . ? C23 C22 H22A 107.2 . . ? C21 C22 H22A 107.2 . . ? C23 C22 H22B 107.2 . . ? C21 C22 H22B 107.2 . . ? H22A C22 H22B 106.9 . . ? C24 C23 C22 117.2(15) . . ? C24 C23 H23A 108.0 . . ? C22 C23 H23A 108.0 . . ? C24 C23 H23B 108.0 . . ? C22 C23 H23B 108.0 . . ? H23A C23 H23B 107.2 . . ? C23 C24 C25 110.1(13) . . ? C23 C24 H24A 109.6 . . ? C25 C24 H24A 109.6 . . ? C23 C24 H24B 109.6 . . ? C25 C24 H24B 109.6 . . ? H24A C24 H24B 108.2 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C116 C111 C112 119.8(7) . . ? C116 C111 P1 118.6(6) . . ? C112 C111 P1 121.6(5) . . ? C111 C112 C113 120.7(7) . . ? C111 C112 H112 119.7 . . ? C113 C112 H112 119.7 . . ? C112 C113 C114 118.7(8) . . ? C112 C113 H113 120.6 . . ? C114 C113 H113 120.6 . . ? C115 C114 C113 120.8(7) . . ? C115 C114 H114 119.6 . . ? C113 C114 H114 119.6 . . ? C114 C115 C116 120.5(8) . . ? C114 C115 H115 119.8 . . ? C116 C115 H115 119.8 . . ? C111 C116 C115 119.6(8) . . ? C111 C116 H116 120.2 . . ? C115 C116 H116 120.2 . . ? C126 C121 C122 119.9(6) . . ? C126 C121 P1 117.6(5) . . ? C122 C121 P1 122.5(5) . . ? C121 C122 C123 119.6(7) . . ? C121 C122 H122 120.2 . . ? C123 C122 H122 120.2 . . ? C124 C123 C122 120.0(7) . . ? C124 C123 H123 120.0 . . ? C122 C123 H123 120.0 . . ? C125 C124 C123 120.5(7) . . ? C125 C124 H124 119.7 . . ? C123 C124 H124 119.7 . . ? C124 C125 C126 119.9(7) . . ? C124 C125 H125 120.0 . . ? C126 C125 H125 120.0 . . ? C121 C126 C125 119.9(6) . . ? C121 C126 H126 120.0 . . ? C125 C126 H126 120.0 . . ? C132 C131 C136 120.0(6) . . ? C132 C131 P1 118.4(5) . . ? C136 C131 P1 121.6(5) . . ? C131 C132 C133 119.7(7) . . ? C131 C132 H132 120.1 . . ? C133 C132 H132 120.1 . . ? C134 C133 C132 119.8(7) . . ? C134 C133 H133 120.1 . . ? C132 C133 H133 120.1 . . ? C133 C134 C135 120.6(7) . . ? C133 C134 H134 119.7 . . ? C135 C134 H134 119.7 . . ? C134 C135 C136 119.6(7) . . ? C134 C135 H135 120.2 . . ? C136 C135 H135 120.2 . . ? C131 C136 C135 120.3(7) . . ? C131 C136 H136 119.9 . . ? C135 C136 H136 119.9 . . ? 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 C3 W1 O1 C1 47.9(6) . . . . ? C4 W1 O1 C1 -42.6(6) . . . . ? C5 W1 O1 C1 -131.7(6) . . . . ? C6 W1 O1 C1 136.2(6) . . . . ? W1 O1 C1 C10 179.9(4) . . . . ? W1 O1 C1 Au1 -0.7(9) . . . . ? O1 C1 C10 C11 -178.6(6) . . . . ? Au1 C1 C10 C11 1.9(9) . . . . ? O1 C1 C10 S1 0.2(9) . . . . ? Au1 C1 C10 S1 -179.3(3) . . . . ? C12 S1 C10 C11 -0.5(5) . . . . ? C12 S1 C10 C1 -179.4(6) . . . . ? C12 N1 C11 C10 0.4(8) . . . . ? C1 C10 C11 N1 179.0(6) . . . . ? S1 C10 C11 N1 0.2(7) . . . . ? C11 N1 C12 C13 179.8(6) . . . . ? C11 N1 C12 S1 -0.7(7) . . . . ? C10 S1 C12 N1 0.7(5) . . . . ? C10 S1 C12 C13 -179.9(6) . . . . ? N1 C12 C13 C18 -5.8(10) . . . . ? S1 C12 C13 C18 174.8(5) . . . . ? N1 C12 C13 C14 174.8(6) . . . . ? S1 C12 C13 C14 -4.6(9) . . . . ? C18 C13 C14 C15 -0.4(10) . . . . ? C12 C13 C14 C15 179.0(6) . . . . ? C13 C14 C15 C16 -0.1(10) . . . . ? C14 C15 C16 C17 0.7(11) . . . . ? C15 C16 C17 C18 -0.8(11) . . . . ? C16 C17 C18 C13 0.3(11) . . . . ? C14 C13 C18 C17 0.3(10) . . . . ? C12 C13 C18 C17 -179.2(6) . . . . ? C21 C22 C23 C24 57.5(18) . . . . ? C22 C23 C24 C25 177.7(11) . . . . ? C131 P1 C111 C116 99.8(6) . . . . ? C121 P1 C111 C116 -149.2(5) . . . . ? Au1 P1 C111 C116 -22.8(6) . . . . ? C131 P1 C111 C112 -78.1(6) . . . . ? C121 P1 C111 C112 32.8(6) . . . . ? Au1 P1 C111 C112 159.2(5) . . . . ? C116 C111 C112 C113 -0.3(11) . . . . ? P1 C111 C112 C113 177.6(6) . . . . ? C111 C112 C113 C114 0.3(11) . . . . ? C112 C113 C114 C115 -0.3(12) . . . . ? C113 C114 C115 C116 0.2(13) . . . . ? C112 C111 C116 C115 0.3(11) . . . . ? P1 C111 C116 C115 -177.7(6) . . . . ? C114 C115 C116 C111 -0.2(12) . . . . ? C131 P1 C121 C126 -164.3(5) . . . . ? C111 P1 C121 C126 83.5(6) . . . . ? Au1 P1 C121 C126 -44.5(5) . . . . ? C131 P1 C121 C122 14.9(6) . . . . ? C111 P1 C121 C122 -97.3(6) . . . . ? Au1 P1 C121 C122 134.7(5) . . . . ? C126 C121 C122 C123 1.1(10) . . . . ? P1 C121 C122 C123 -178.1(6) . . . . ? C121 C122 C123 C124 0.3(11) . . . . ? C122 C123 C124 C125 -0.9(12) . . . . ? C123 C124 C125 C126 0.0(11) . . . . ? C122 C121 C126 C125 -1.9(10) . . . . ? P1 C121 C126 C125 177.3(5) . . . . ? C124 C125 C126 C121 1.4(10) . . . . ? C121 P1 C131 C132 71.1(6) . . . . ? C111 P1 C131 C132 -176.6(5) . . . . ? Au1 P1 C131 C132 -50.6(5) . . . . ? C121 P1 C131 C136 -108.2(6) . . . . ? C111 P1 C131 C136 4.0(6) . . . . ? Au1 P1 C131 C136 130.1(5) . . . . ? C136 C131 C132 C133 2.3(10) . . . . ? P1 C131 C132 C133 -177.1(5) . . . . ? C131 C132 C133 C134 -1.5(10) . . . . ? C132 C133 C134 C135 -0.1(11) . . . . ? C133 C134 C135 C136 0.9(11) . . . . ? C132 C131 C136 C135 -1.5(10) . . . . ? P1 C131 C136 C135 177.8(6) . . . . ? C134 C135 C136 C131 -0.1(11) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 3.713 _refine_diff_density_min -1.101 _refine_diff_density_rms 0.174 #===END # Attachment '- CIF.CIF' data_Compound-1a _database_code_depnum_ccdc_archive 'CCDC 744822' _audit_creation_method SHELXL-97 _chemical_name_systematic ;tetramethylammonium pentacarbonyl{[2-(1-piperidinyl)thiazol- 5-yl]carbonyl}tungstate(1-) ; _chemical_name_common ;{[2-(1-piperidinyl)thiophen-5-yl]carbonyl}pentacarbonyl- tungstate(-I) tetramethylammonium salt ; _chemical_melting_point 418 _chemical_formula_moiety 'C14 H11 N2 O6 S W, C4 H12 N' _chemical_formula_sum 'C18 H23 N3 O6 S W' _chemical_formula_weight 593.30 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_int_tables_number 15 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 22.688(4) _cell_length_b 9.0983(15) _cell_length_c 21.294(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.674(2) _cell_angle_gamma 90.00 _cell_volume 4390.7(12) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7210 _cell_measurement_theta_min 2.565 _cell_measurement_theta_max 26.421 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.795 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2320 _exptl_absorpt_coefficient_mu 5.395 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.314 _exptl_absorpt_correction_T_max 0.497 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12017 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 26.42 _reflns_number_total 4456 _reflns_number_gt 4102 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)' _computing_publication_material X-Seed _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^)+(0.0687P)^2^+2.0417P] 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 4456 _refine_ls_number_parameters 266 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 W1 W 0.103346(6) 0.27625(2) 0.843944(7) 0.01431(10) Uani 1 1 d . . . S1 S 0.25443(4) 0.65280(12) 0.89449(5) 0.0158(2) Uani 1 1 d . . . O1 O 0.16250(14) 0.5706(4) 0.80964(15) 0.0315(8) Uani 1 1 d . . . O3 O 0.0931(2) 0.2709(4) 0.99218(19) 0.0302(9) Uani 1 1 d . . . O4 O 0.21413(13) 0.0613(4) 0.85100(15) 0.0278(8) Uani 1 1 d . . . O2 O 0.00483(16) 0.0332(5) 0.82941(17) 0.0316(9) Uani 1 1 d . . . O5 O 0.1152(2) 0.2772(4) 0.6958(2) 0.0349(10) Uani 1 1 d . . . O6 O 0.00717(16) 0.5294(4) 0.82760(16) 0.0337(9) Uani 1 1 d . . . N1 N 0.28155(15) 0.4625(4) 0.98220(16) 0.0166(8) Uani 1 1 d . . . N2 N 0.34508(15) 0.6689(4) 0.98061(16) 0.0170(7) Uani 1 1 d . . . N3 N 0.13317(17) 0.7960(4) 0.68720(18) 0.0157(8) Uani 1 1 d . . . C1 C 0.16559(19) 0.4690(5) 0.8491(2) 0.0173(9) Uani 1 1 d . . . C3 C 0.0971(2) 0.2745(5) 0.9392(3) 0.0197(11) Uani 1 1 d . . . C4 C 0.17320(19) 0.1365(5) 0.8498(2) 0.0190(9) Uani 1 1 d . . . C2 C 0.0418(2) 0.1205(6) 0.8345(2) 0.0195(9) Uani 1 1 d . . . C5 C 0.1113(2) 0.2782(5) 0.7488(3) 0.0229(11) Uani 1 1 d . . . C6 C 0.0414(2) 0.4361(6) 0.8338(2) 0.0208(10) Uani 1 1 d . . . C10 C 0.21284(17) 0.4904(5) 0.89763(18) 0.0153(8) Uani 1 1 d . . . C11 C 0.23444(16) 0.4075(5) 0.94703(18) 0.0150(8) Uani 1 1 d . . . H11 H 0.2175 0.3152 0.9566 0.018 Uiso 1 1 calc R . . C12 C 0.29706(16) 0.5911(5) 0.95946(18) 0.0156(8) Uani 1 1 d . . . C13 C 0.37308(18) 0.6306(5) 1.0417(2) 0.0205(9) Uani 1 1 d . . . H13B H 0.3686 0.5239 1.0492 0.025 Uiso 1 1 calc R . . H13A H 0.3532 0.6838 1.0753 0.025 Uiso 1 1 calc R . . C14 C 0.4383(2) 0.6703(6) 1.0441(2) 0.0263(10) Uani 1 1 d . . . H14B H 0.4593 0.6065 1.0148 0.032 Uiso 1 1 calc R . . H14A H 0.4555 0.6535 1.0871 0.032 Uiso 1 1 calc R . . C15 C 0.4463(2) 0.8312(6) 1.0259(2) 0.0265(10) Uani 1 1 d . . . H15A H 0.4276 0.8954 1.0568 0.032 Uiso 1 1 calc R . . H15B H 0.4889 0.8552 1.0264 0.032 Uiso 1 1 calc R . . C16 C 0.41853(19) 0.8585(6) 0.9607(2) 0.0234(10) Uani 1 1 d . . . H16A H 0.4233 0.9631 0.9494 0.028 Uiso 1 1 calc R . . H16B H 0.4388 0.7980 0.9296 0.028 Uiso 1 1 calc R . . C17 C 0.35363(19) 0.8198(5) 0.9590(2) 0.0178(9) Uani 1 1 d . . . H17A H 0.3326 0.8885 0.9862 0.021 Uiso 1 1 calc R . . H17B H 0.3368 0.8303 0.9155 0.021 Uiso 1 1 calc R . . C20 C 0.19039(19) 0.8454(6) 0.7166(2) 0.0262(10) Uani 1 1 d . . . H20A H 0.2211 0.8383 0.6859 0.039 Uiso 1 1 calc R . . H20B H 0.2009 0.7830 0.7529 0.039 Uiso 1 1 calc R . . H20C H 0.1869 0.9477 0.7304 0.039 Uiso 1 1 calc R . . C21 C 0.0863(2) 0.8082(6) 0.7349(2) 0.0247(10) Uani 1 1 d . . . H21A H 0.0837 0.9103 0.7492 0.037 Uiso 1 1 calc R . . H21B H 0.0965 0.7444 0.7709 0.037 Uiso 1 1 calc R . . H21C H 0.0481 0.7778 0.7156 0.037 Uiso 1 1 calc R . . C22 C 0.1385(2) 0.6407(5) 0.6660(2) 0.0247(10) Uani 1 1 d . . . H22A H 0.1004 0.6074 0.6475 0.037 Uiso 1 1 calc R . . H22B H 0.1499 0.5784 0.7020 0.037 Uiso 1 1 calc R . . H22C H 0.1685 0.6342 0.6345 0.037 Uiso 1 1 calc R . . C23 C 0.11646(19) 0.8921(6) 0.6320(2) 0.0245(10) Uani 1 1 d . . . H23A H 0.1454 0.8804 0.5997 0.037 Uiso 1 1 calc R . . H23B H 0.1157 0.9950 0.6456 0.037 Uiso 1 1 calc R . . H23C H 0.0773 0.8639 0.6147 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 W1 0.01248(13) 0.01910(16) 0.01183(14) -0.00016(6) 0.00567(8) -0.00120(6) S1 0.0151(5) 0.0172(5) 0.0154(5) 0.0016(4) 0.0037(4) -0.0013(4) O1 0.0306(17) 0.033(2) 0.0301(18) 0.0159(16) -0.0076(14) -0.0095(16) O3 0.037(2) 0.038(2) 0.016(2) 0.0029(14) 0.0101(17) 0.0083(16) O4 0.0198(16) 0.035(2) 0.0295(18) -0.0037(16) 0.0086(13) 0.0035(15) O2 0.0248(18) 0.037(2) 0.033(2) 0.0001(17) 0.0028(15) -0.0108(17) O5 0.053(3) 0.036(3) 0.016(2) 0.0007(14) 0.0078(19) -0.0010(17) O6 0.0288(18) 0.041(2) 0.031(2) -0.0007(17) 0.0019(15) 0.0150(18) N1 0.0130(16) 0.022(2) 0.0153(17) -0.0011(15) 0.0050(13) 0.0001(15) N2 0.0159(17) 0.021(2) 0.0144(17) 0.0031(15) 0.0019(13) -0.0021(15) N3 0.0153(18) 0.019(2) 0.0132(19) 0.0018(14) 0.0074(14) 0.0009(14) C1 0.016(2) 0.021(2) 0.014(2) 0.0002(17) 0.0044(16) 0.0016(18) C3 0.014(2) 0.023(3) 0.022(3) 0.0027(18) 0.007(2) 0.0052(17) C4 0.016(2) 0.022(2) 0.020(2) -0.0044(18) 0.0054(17) -0.0049(19) C2 0.016(2) 0.021(2) 0.022(2) 0.0019(19) 0.0053(17) -0.0035(19) C5 0.020(3) 0.026(3) 0.023(3) 0.0004(18) 0.003(2) -0.0010(18) C6 0.020(2) 0.027(3) 0.015(2) 0.0015(19) 0.0002(17) -0.003(2) C10 0.0152(19) 0.019(2) 0.0124(19) -0.0024(16) 0.0082(15) -0.0030(16) C11 0.0135(18) 0.017(2) 0.016(2) -0.0001(16) 0.0085(15) -0.0005(16) C12 0.0141(19) 0.020(2) 0.0132(19) 0.0008(17) 0.0075(15) 0.0040(16) C13 0.016(2) 0.023(2) 0.023(2) 0.0030(19) 0.0011(17) -0.0006(18) C14 0.017(2) 0.029(3) 0.032(3) 0.004(2) -0.0004(19) -0.002(2) C15 0.021(2) 0.032(3) 0.027(3) -0.002(2) -0.0010(19) -0.007(2) C16 0.020(2) 0.031(3) 0.020(2) 0.000(2) 0.0073(17) -0.005(2) C17 0.018(2) 0.020(2) 0.016(2) -0.0010(18) 0.0058(16) -0.0021(18) C20 0.023(2) 0.034(3) 0.023(2) 0.005(2) 0.0058(18) -0.005(2) C21 0.022(2) 0.036(3) 0.017(2) 0.008(2) 0.0150(19) 0.005(2) C22 0.025(2) 0.020(2) 0.029(3) -0.004(2) 0.0043(19) -0.0005(19) C23 0.026(2) 0.030(3) 0.018(2) 0.005(2) 0.0116(18) 0.002(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 W1 C2 1.994(5) . ? W1 C6 2.027(5) . ? W1 C4 2.031(5) . ? W1 C3 2.040(6) . ? W1 C5 2.042(6) . ? W1 C1 2.251(5) . ? S1 C12 1.743(4) . ? S1 C10 1.756(4) . ? O1 C1 1.248(5) . ? O3 C3 1.137(7) . ? O4 C4 1.152(6) . ? O2 C2 1.156(6) . ? O5 C5 1.136(7) . ? O6 C6 1.154(6) . ? N1 C12 1.320(6) . ? N1 C11 1.371(5) . ? N2 C12 1.358(5) . ? N2 C13 1.462(5) . ? N2 C17 1.464(6) . ? N3 C20 1.484(6) . ? N3 C22 1.490(6) . ? N3 C23 1.499(6) . ? N3 C21 1.509(5) . ? C1 C10 1.467(6) . ? C10 C11 1.367(6) . ? C11 H11 0.9500 . ? C13 C14 1.521(6) . ? C13 H13B 0.9900 . ? C13 H13A 0.9900 . ? C14 C15 1.528(7) . ? C14 H14B 0.9900 . ? C14 H14A 0.9900 . ? C15 C16 1.518(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.513(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 C2 W1 C6 91.1(2) . . ? C2 W1 C4 95.9(2) . . ? C6 W1 C4 172.22(18) . . ? C2 W1 C3 90.8(2) . . ? C6 W1 C3 91.81(18) . . ? C4 W1 C3 91.44(18) . . ? C2 W1 C5 90.0(2) . . ? C6 W1 C5 88.88(19) . . ? C4 W1 C5 87.78(19) . . ? C3 W1 C5 178.96(17) . . ? C2 W1 C1 173.60(17) . . ? C6 W1 C1 82.9(2) . . ? C4 W1 C1 89.93(17) . . ? C3 W1 C1 91.75(18) . . ? C5 W1 C1 87.56(18) . . ? C12 S1 C10 88.8(2) . . ? C12 N1 C11 109.7(4) . . ? C12 N2 C13 118.6(4) . . ? C12 N2 C17 120.0(3) . . ? C13 N2 C17 116.4(4) . . ? C20 N3 C22 109.5(4) . . ? C20 N3 C23 109.7(3) . . ? C22 N3 C23 109.7(4) . . ? C20 N3 C21 108.9(4) . . ? C22 N3 C21 110.1(4) . . ? C23 N3 C21 108.9(3) . . ? O1 C1 C10 113.1(4) . . ? O1 C1 W1 121.9(3) . . ? C10 C1 W1 125.0(3) . . ? O3 C3 W1 178.7(5) . . ? O4 C4 W1 176.7(4) . . ? O2 C2 W1 178.0(4) . . ? O5 C5 W1 178.9(5) . . ? O6 C6 W1 178.3(4) . . ? C11 C10 C1 133.9(4) . . ? C11 C10 S1 108.6(3) . . ? C1 C10 S1 117.5(3) . . ? C10 C11 N1 117.5(4) . . ? C10 C11 H11 121.3 . . ? N1 C11 H11 121.3 . . ? N1 C12 N2 124.3(4) . . ? N1 C12 S1 115.4(3) . . ? N2 C12 S1 120.1(3) . . ? N2 C13 C14 110.8(4) . . ? N2 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? N2 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? H13B C13 H13A 108.1 . . ? C13 C14 C15 110.3(4) . . ? C13 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? H14B C14 H14A 108.1 . . ? C16 C15 C14 109.8(4) . . ? C16 C15 H15A 109.7 . . ? C14 C15 H15A 109.7 . . ? C16 C15 H15B 109.7 . . ? C14 C15 H15B 109.7 . . ? H15A C15 H15B 108.2 . . ? C17 C16 C15 110.3(4) . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16B 109.6 . . ? C15 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? N2 C17 C16 110.7(4) . . ? N2 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N3 C23 H23A 109.5 . . ? N3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 C6 W1 C1 O1 -48.8(4) . . . . ? C4 W1 C1 O1 128.1(4) . . . . ? C3 W1 C1 O1 -140.4(4) . . . . ? C5 W1 C1 O1 40.4(4) . . . . ? C6 W1 C1 C10 130.8(4) . . . . ? C4 W1 C1 C10 -52.2(4) . . . . ? C3 W1 C1 C10 39.2(4) . . . . ? C5 W1 C1 C10 -140.0(4) . . . . ? O1 C1 C10 C11 -176.0(4) . . . . ? W1 C1 C10 C11 4.4(7) . . . . ? O1 C1 C10 S1 2.2(5) . . . . ? W1 C1 C10 S1 -177.5(2) . . . . ? C12 S1 C10 C11 0.6(3) . . . . ? C12 S1 C10 C1 -178.0(3) . . . . ? C1 C10 C11 N1 177.9(4) . . . . ? S1 C10 C11 N1 -0.4(4) . . . . ? C12 N1 C11 C10 -0.2(5) . . . . ? C11 N1 C12 N2 -174.5(4) . . . . ? C11 N1 C12 S1 0.7(4) . . . . ? C13 N2 C12 N1 -16.6(6) . . . . ? C17 N2 C12 N1 -170.8(4) . . . . ? C13 N2 C12 S1 168.4(3) . . . . ? C17 N2 C12 S1 14.2(5) . . . . ? C10 S1 C12 N1 -0.8(3) . . . . ? C10 S1 C12 N2 174.7(3) . . . . ? C12 N2 C13 C14 152.6(4) . . . . ? C17 N2 C13 C14 -52.3(5) . . . . ? N2 C13 C14 C15 53.3(5) . . . . ? C13 C14 C15 C16 -57.7(5) . . . . ? C14 C15 C16 C17 58.4(5) . . . . ? C12 N2 C17 C16 -152.3(4) . . . . ? C13 N2 C17 C16 52.9(5) . . . . ? C15 C16 C17 N2 -54.6(5) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 3.448 _refine_diff_density_min -3.509 _refine_diff_density_rms 0.240 #===END data_Compound-3b _database_code_depnum_ccdc_archive 'CCDC 744823' _audit_creation_method SHELXL-97 _chemical_name_systematic Pentacarbonyl[methoxy(2-phenylthiazol-5-yl)methylidene]tungsten _chemical_name_common '[Methoxy(2-phenylthiazol-5-yl)carbene]pentacarbonyltungsten(0)' _chemical_melting_point ? _chemical_formula_moiety 'C16 H9 N O6 S W' _chemical_formula_sum 'C16 H9 N O6 S W' _chemical_formula_weight 527.15 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c c n' _symmetry_space_group_name_Hall '-P 2ab 2ac' _symmetry_int_tables_number 56 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 17.336(2) _cell_length_b 26.055(3) _cell_length_c 7.4114(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3347.5(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6608 _cell_measurement_theta_min 2.349 _cell_measurement_theta_max 26.344 _exptl_crystal_description needle _exptl_crystal_colour 'dark orange' _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.092 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 7.059 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.468 _exptl_absorpt_correction_T_max 0.806 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17901 _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 26.39 _reflns_number_total 3425 _reflns_number_gt 3009 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)' _computing_publication_material X-Seed _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^)+(0.0336P)^2^+8.0471P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3425 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0697 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _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 W1 W 0.392068(10) 0.383510(7) 0.28419(3) 0.01286(8) Uani 1 1 d . . . S1 S 0.60935(6) 0.26806(5) 0.18990(15) 0.0138(2) Uani 1 1 d . . . O1 O 0.57466(18) 0.36983(12) 0.2322(4) 0.0150(7) Uani 1 1 d . . . O2 O 0.2243(2) 0.43167(16) 0.2858(6) 0.0371(10) Uani 1 1 d . . . O3 O 0.4240(2) 0.46591(14) -0.0223(5) 0.0291(9) Uani 1 1 d . . . O4 O 0.4400(2) 0.46430(13) 0.5849(5) 0.0245(8) Uani 1 1 d . . . O5 O 0.33772(19) 0.31183(14) 0.6081(5) 0.0249(8) Uani 1 1 d . . . O6 O 0.32895(19) 0.30183(13) 0.0006(5) 0.0247(8) Uani 1 1 d . . . N1 N 0.5018(2) 0.20474(16) 0.2784(5) 0.0163(8) Uani 1 1 d . . . C1 C 0.5063(3) 0.34792(19) 0.2586(6) 0.0130(9) Uani 1 1 d . . . C2 C 0.2844(3) 0.4140(2) 0.2872(7) 0.0208(11) Uani 1 1 d . . . C3 C 0.4152(3) 0.43506(18) 0.0848(7) 0.0168(10) Uani 1 1 d . . . C4 C 0.4248(3) 0.43507(18) 0.4769(7) 0.0180(10) Uani 1 1 d . . . C5 C 0.3598(3) 0.33632(18) 0.4929(6) 0.0167(10) Uani 1 1 d . . . C6 C 0.3532(2) 0.33073(18) 0.0994(6) 0.0152(10) Uani 1 1 d . . . C7 C 0.5827(3) 0.42510(18) 0.2265(7) 0.0201(11) Uani 1 1 d . . . H7A H 0.6369 0.4341 0.2063 0.030 Uiso 1 1 calc R . . H7B H 0.5654 0.4398 0.3414 0.030 Uiso 1 1 calc R . . H7C H 0.5511 0.4389 0.1281 0.030 Uiso 1 1 calc R . . C10 C 0.5201(3) 0.29314(18) 0.2541(6) 0.0141(10) Uani 1 1 d . . . C11 C 0.4726(3) 0.25277(18) 0.2953(6) 0.0156(9) Uani 1 1 d . . . H11 H 0.4210 0.2582 0.3343 0.019 Uiso 1 1 calc R . . C12 C 0.5740(3) 0.20644(18) 0.2204(6) 0.0144(9) Uani 1 1 d . . . C13 C 0.6196(2) 0.16070(18) 0.1845(6) 0.0136(9) Uani 1 1 d . . . C14 C 0.5899(3) 0.11303(19) 0.2327(7) 0.0197(11) Uani 1 1 d . . . H14 H 0.5408 0.1107 0.2890 0.024 Uiso 1 1 calc R . . C15 C 0.6327(3) 0.06866(19) 0.1979(7) 0.0217(11) Uani 1 1 d . . . H15 H 0.6126 0.0361 0.2309 0.026 Uiso 1 1 calc R . . C16 C 0.7044(3) 0.07204(19) 0.1154(7) 0.0230(11) Uani 1 1 d . . . H16 H 0.7332 0.0418 0.0917 0.028 Uiso 1 1 calc R . . C17 C 0.7338(3) 0.11943(18) 0.0677(7) 0.0204(10) Uani 1 1 d . . . H17 H 0.7828 0.1216 0.0108 0.025 Uiso 1 1 calc R . . C18 C 0.6921(2) 0.16373(18) 0.1023(6) 0.0156(10) Uani 1 1 d . . . H18 H 0.7128 0.1962 0.0702 0.019 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 W1 0.01102(11) 0.01420(12) 0.01335(12) -0.00027(7) 0.00085(7) 0.00178(7) S1 0.0118(5) 0.0156(6) 0.0139(6) 0.0007(4) 0.0021(4) 0.0005(4) O1 0.0117(15) 0.0131(16) 0.0203(18) 0.0013(13) 0.0033(13) 0.0004(13) O2 0.019(2) 0.045(3) 0.047(3) -0.004(2) -0.0019(18) 0.0159(18) O3 0.034(2) 0.027(2) 0.026(2) 0.0085(17) -0.0059(17) -0.0069(16) O4 0.031(2) 0.0228(19) 0.0199(19) -0.0077(15) 0.0044(16) -0.0035(15) O5 0.0207(18) 0.032(2) 0.022(2) 0.0088(16) 0.0021(15) -0.0004(15) O6 0.0175(17) 0.031(2) 0.025(2) -0.0089(16) 0.0002(15) -0.0001(15) N1 0.0121(18) 0.020(2) 0.017(2) 0.0016(16) 0.0015(16) 0.0013(16) C1 0.014(2) 0.018(2) 0.007(2) 0.0010(17) -0.0020(16) -0.0020(18) C2 0.022(3) 0.021(3) 0.019(3) -0.004(2) 0.000(2) 0.003(2) C3 0.015(2) 0.018(3) 0.017(2) -0.003(2) -0.0012(19) 0.0008(19) C4 0.014(2) 0.017(3) 0.023(3) 0.006(2) 0.002(2) 0.0029(19) C5 0.012(2) 0.020(3) 0.018(3) -0.0037(19) -0.0014(19) 0.0012(18) C6 0.011(2) 0.018(3) 0.017(2) -0.0011(19) 0.0045(18) 0.0042(19) C7 0.021(2) 0.013(2) 0.027(3) -0.001(2) 0.004(2) -0.0087(19) C10 0.011(2) 0.021(3) 0.010(2) -0.0009(18) 0.0007(16) -0.0012(18) C11 0.013(2) 0.017(2) 0.017(2) 0.0011(18) 0.0028(18) 0.0016(19) C12 0.018(2) 0.015(2) 0.010(2) 0.0001(18) -0.0033(18) -0.0019(18) C13 0.015(2) 0.019(3) 0.006(2) -0.0017(17) -0.0055(17) 0.0005(18) C14 0.017(2) 0.024(3) 0.018(3) 0.000(2) 0.000(2) 0.0014(19) C15 0.024(3) 0.014(3) 0.027(3) -0.002(2) -0.004(2) -0.004(2) C16 0.021(2) 0.018(3) 0.030(3) -0.006(2) -0.009(2) 0.008(2) C17 0.016(2) 0.026(3) 0.020(3) -0.002(2) 0.000(2) 0.0037(19) C18 0.015(2) 0.017(2) 0.014(2) 0.0041(18) -0.0037(18) 0.0018(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 W1 C2 2.029(5) . ? W1 C3 2.037(5) . ? W1 C4 2.041(5) . ? W1 C5 2.053(5) . ? W1 C6 2.055(5) . ? W1 C1 2.195(5) . ? S1 C12 1.733(5) . ? S1 C10 1.746(5) . ? O1 C1 1.330(5) . ? O1 C7 1.447(5) . ? O2 C2 1.138(6) . ? O3 C3 1.140(6) . ? O4 C4 1.136(6) . ? O5 C5 1.133(6) . ? O6 C6 1.131(5) . ? N1 C12 1.323(6) . ? N1 C11 1.356(6) . ? C1 C10 1.447(7) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C10 C11 1.370(7) . ? C11 H11 0.9500 . ? C12 C13 1.455(7) . ? C13 C14 1.391(7) . ? C13 C18 1.399(6) . ? C14 C15 1.397(7) . ? C14 H14 0.9500 . ? C15 C16 1.389(7) . ? C15 H15 0.9500 . ? C16 C17 1.382(7) . ? C16 H16 0.9500 . ? C17 C18 1.386(6) . ? C17 H17 0.9500 . ? C18 H18 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 C2 W1 C3 86.1(2) . . ? C2 W1 C4 89.43(19) . . ? C3 W1 C4 91.08(19) . . ? C2 W1 C5 88.61(19) . . ? C3 W1 C5 174.25(18) . . ? C4 W1 C5 86.71(19) . . ? C2 W1 C6 88.13(18) . . ? C3 W1 C6 91.29(19) . . ? C4 W1 C6 176.48(17) . . ? C5 W1 C6 90.69(18) . . ? C2 W1 C1 175.22(18) . . ? C3 W1 C1 92.19(17) . . ? C4 W1 C1 95.04(17) . . ? C5 W1 C1 93.30(17) . . ? C6 W1 C1 87.47(16) . . ? C12 S1 C10 89.9(2) . . ? C1 O1 C7 121.1(4) . . ? C12 N1 C11 110.6(4) . . ? O1 C1 C10 105.8(4) . . ? O1 C1 W1 129.4(3) . . ? C10 C1 W1 124.6(3) . . ? O2 C2 W1 178.6(5) . . ? O3 C3 W1 175.2(4) . . ? O4 C4 W1 177.3(4) . . ? O5 C5 W1 175.7(4) . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O6 C6 W1 177.3(4) . . ? C11 C10 C1 130.7(4) . . ? C11 C10 S1 107.8(3) . . ? C1 C10 S1 121.4(3) . . ? N1 C11 C10 117.6(4) . . ? N1 C11 H11 121.2 . . ? C10 C11 H11 121.2 . . ? N1 C12 C13 123.1(4) . . ? N1 C12 S1 114.1(4) . . ? C13 C12 S1 122.9(4) . . ? C14 C13 C18 119.6(4) . . ? C14 C13 C12 118.9(4) . . ? C18 C13 C12 121.4(4) . . ? C13 C14 C15 119.7(5) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C16 C15 C14 120.3(5) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 120.0(4) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.3(5) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 120.2(4) . . ? C17 C18 H18 119.9 . . ? C13 C18 H18 119.9 . . ? 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 C7 O1 C1 C10 179.4(4) . . . . ? C7 O1 C1 W1 3.7(6) . . . . ? C3 W1 C1 O1 40.1(4) . . . . ? C4 W1 C1 O1 -51.1(4) . . . . ? C5 W1 C1 O1 -138.1(4) . . . . ? C6 W1 C1 O1 131.3(4) . . . . ? C3 W1 C1 C10 -134.7(4) . . . . ? C4 W1 C1 C10 134.0(4) . . . . ? C5 W1 C1 C10 47.0(4) . . . . ? C6 W1 C1 C10 -43.5(4) . . . . ? O1 C1 C10 C11 170.9(5) . . . . ? W1 C1 C10 C11 -13.2(7) . . . . ? O1 C1 C10 S1 -8.6(5) . . . . ? W1 C1 C10 S1 167.3(2) . . . . ? C12 S1 C10 C11 1.0(3) . . . . ? C12 S1 C10 C1 -179.4(4) . . . . ? C12 N1 C11 C10 -0.8(6) . . . . ? C1 C10 C11 N1 -179.9(4) . . . . ? S1 C10 C11 N1 -0.4(5) . . . . ? C11 N1 C12 C13 -178.1(4) . . . . ? C11 N1 C12 S1 1.6(5) . . . . ? C10 S1 C12 N1 -1.5(4) . . . . ? C10 S1 C12 C13 178.2(4) . . . . ? N1 C12 C13 C14 -7.8(7) . . . . ? S1 C12 C13 C14 172.5(4) . . . . ? N1 C12 C13 C18 172.0(4) . . . . ? S1 C12 C13 C18 -7.7(6) . . . . ? C18 C13 C14 C15 -0.3(7) . . . . ? C12 C13 C14 C15 179.5(4) . . . . ? C13 C14 C15 C16 -0.1(8) . . . . ? C14 C15 C16 C17 0.1(8) . . . . ? C15 C16 C17 C18 0.2(8) . . . . ? C16 C17 C18 C13 -0.6(7) . . . . ? C14 C13 C18 C17 0.6(7) . . . . ? C12 C13 C18 C17 -179.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.371 _refine_diff_density_min -1.309 _refine_diff_density_rms 0.155 #===END data_Compound-4 _database_code_depnum_ccdc_archive 'CCDC 744824' _audit_creation_method SHELXL-97 _chemical_name_systematic ;cocrystallisate of pentacarbonyl{hydroxy[2-(1-piperidyl)thiazol- 5-yl]methylidene}tungsten and tetramethylammonium pentacarbonyl{[2-(1-piperidyl)thiazol-5-yl]carbonyl}tungstate(1-) bis-trichloromethane solvate ; _chemical_name_common ; cocrystallisate of pentacarbonyl(hydroxy(2-(1- piperidyl)thiazol-5- yl)methylidene)tungsten and tetramethylammonium pentacarbonyl((2-(1- piperidyl)thiazol-5-yl)carbonyl)tungstate(1-) bis- trichloromethane solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 N2 O6 S W, C14 H11 N2 O6 S W, C4 H12 N, 2(C H Cl3)' _chemical_formula_sum 'C34 H37 Cl6 N5 O12 S2 W2' _chemical_formula_weight 1352.2 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_int_tables_number 15 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 26.273(7) _cell_length_b 11.491(3) _cell_length_c 16.925(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.940(4) _cell_angle_gamma 90.00 _cell_volume 4740(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2833 _cell_measurement_theta_min 2.507 _cell_measurement_theta_max 25.157 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.895 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2616 _exptl_absorpt_coefficient_mu 5.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.576 _exptl_absorpt_correction_T_max 0.949 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13592 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.0685 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 27.18 _reflns_number_total 5220 _reflns_number_gt 4051 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)' _computing_publication_material X-Seed _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^)+(0.0687P)^2^] 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 5220 _refine_ls_number_parameters 290 _refine_ls_number_restraints 6 # SADI restraints for C---N bonds involving N3, C20, C21, C22, C23 _refine_ls_R_factor_all 0.0731 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1245 _refine_ls_wR_factor_gt 0.1153 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 W1 W 0.547343(12) 0.76785(3) 0.622768(18) 0.02154(11) Uani 1 1 d . . . Cl1 Cl 0.77449(11) 0.9610(2) 0.74971(16) 0.0561(7) Uani 1 1 d . . . Cl2 Cl 0.82050(16) 0.7366(3) 0.7421(3) 0.0954(13) Uani 1 1 d . . . Cl3 Cl 0.87407(9) 0.8882(2) 0.88412(16) 0.0507(6) Uani 1 1 d . . . S1 S 0.65549(7) 0.59172(17) 0.89969(11) 0.0243(4) Uani 1 1 d . . . O1 O 0.54953(19) 0.6224(5) 0.7828(3) 0.0245(11) Uani 1 1 d . . . H1 H 0.5164 0.6270 0.7504 0.029 Uiso 0.50 1 calc PR . . O4 O 0.6428(3) 0.6666(6) 0.5713(4) 0.0464(16) Uani 1 1 d . . . O3 O 0.6182(3) 0.9865(6) 0.7153(4) 0.0469(16) Uani 1 1 d . . . O2 O 0.5035(3) 0.8908(5) 0.4430(3) 0.0462(16) Uani 1 1 d . . . O5 O 0.4496(2) 0.8944(5) 0.6551(3) 0.0324(13) Uani 1 1 d . . . O6 O 0.4712(2) 0.5476(6) 0.5521(4) 0.0438(16) Uani 1 1 d . . . N1 N 0.7314(3) 0.6980(6) 0.8627(4) 0.0254(14) Uani 1 1 d . . . N2 N 0.7640(3) 0.5980(6) 0.9920(4) 0.0267(14) Uani 1 1 d . . . N3 N 0.5000 0.7147(8) 0.2500 0.035(2) Uani 1 2 d SD . . C1 C 0.5792(3) 0.6773(7) 0.7496(4) 0.0220(15) Uani 1 1 d . . . C4 C 0.6081(3) 0.7005(7) 0.5916(5) 0.0308(18) Uani 1 1 d . . . C3 C 0.5932(3) 0.9072(8) 0.6804(5) 0.0322(19) Uani 1 1 d . . . C2 C 0.5197(3) 0.8471(7) 0.5085(5) 0.0310(19) Uani 1 1 d . . . C5 C 0.4846(3) 0.8460(7) 0.6452(5) 0.0268(17) Uani 1 1 d . . . C6 C 0.4992(3) 0.6264(7) 0.5766(5) 0.0277(17) Uani 1 1 d . . . C8 C 0.8118(3) 0.8434(7) 0.8084(5) 0.0319(18) Uani 1 1 d . . . H8 H 0.7899 0.8085 0.8396 0.038 Uiso 1 1 calc R . . C10 C 0.6362(3) 0.6701(6) 0.8039(4) 0.0191(15) Uani 1 1 d . . . C11 C 0.6821(3) 0.7168(6) 0.7985(4) 0.0228(16) Uani 1 1 d . . . H11 H 0.6799 0.7621 0.7504 0.027 Uiso 1 1 calc R . . C12 C 0.7231(3) 0.6307(6) 0.9210(4) 0.0218(15) Uani 1 1 d . . . C13 C 0.7557(3) 0.5137(8) 1.0505(5) 0.039(2) Uani 1 1 d . . . H13A H 0.7163 0.5098 1.0416 0.046 Uiso 1 1 calc R . . H13B H 0.7764 0.5381 1.1100 0.046 Uiso 1 1 calc R . . C14 C 0.7751(5) 0.3967(8) 1.0352(6) 0.055(3) Uani 1 1 d . . . H14A H 0.7528 0.3703 0.9768 0.065 Uiso 1 1 calc R . . H14B H 0.7705 0.3397 1.0759 0.065 Uiso 1 1 calc R . . C15 C 0.8349(5) 0.4027(9) 1.0462(6) 0.059(3) Uani 1 1 d . . . H15A H 0.8468 0.3260 1.0328 0.070 Uiso 1 1 calc R . . H15B H 0.8575 0.4216 1.1062 0.070 Uiso 1 1 calc R . . C16 C 0.8438(4) 0.4944(10) 0.9883(6) 0.053(3) Uani 1 1 d . . . H16A H 0.8835 0.5015 0.9999 0.063 Uiso 1 1 calc R . . H16B H 0.8249 0.4705 0.9281 0.063 Uiso 1 1 calc R . . C17 C 0.8217(3) 0.6102(8) 1.0025(5) 0.036(2) Uani 1 1 d . . . H17A H 0.8434 0.6386 1.0607 0.043 Uiso 1 1 calc R . . H17B H 0.8250 0.6678 0.9612 0.043 Uiso 1 1 calc R . . C20 C 0.5000 0.8443(11) 0.2500 0.095(7) Uani 1 2 d SD A . H20A H 0.5246 0.8727 0.3058 0.143 Uiso 0.50 1 calc PR . . H20B H 0.4627 0.8727 0.2383 0.143 Uiso 0.50 1 calc PR . . H20C H 0.5127 0.8727 0.2059 0.143 Uiso 0.50 1 calc PR . . C21 C 0.5451(10) 0.687(2) 0.2225(19) 0.078(8) Uani 0.50 1 d PD A 3 H21A H 0.5616 0.7594 0.2124 0.117 Uiso 0.50 1 calc P B 3 H21B H 0.5312 0.6416 0.1697 0.117 Uiso 0.50 1 calc P C 3 H21C H 0.5730 0.6417 0.2669 0.117 Uiso 0.50 1 calc P D 3 C22 C 0.5508(8) 0.6744(19) 0.3209(13) 0.067(6) Uani 0.50 1 d PD A 2 H22A H 0.5517 0.5891 0.3220 0.101 Uiso 0.50 1 calc P E 2 H22B H 0.5508 0.7037 0.3752 0.101 Uiso 0.50 1 calc P F 2 H22C H 0.5832 0.7039 0.3117 0.101 Uiso 0.50 1 calc P G 2 C23 C 0.5035(10) 0.6516(17) 0.3279(11) 0.050(5) Uani 0.50 1 d PD A 1 H23A H 0.5064 0.7077 0.3730 0.075 Uiso 0.50 1 calc P H 1 H23B H 0.5360 0.6013 0.3465 0.075 Uiso 0.50 1 calc P I 1 H23C H 0.4705 0.6040 0.3159 0.075 Uiso 0.50 1 calc P J 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 W1 0.02752(18) 0.02385(18) 0.01591(16) 0.00160(13) 0.01117(12) 0.00309(13) Cl1 0.0597(16) 0.0605(18) 0.0469(14) 0.0252(13) 0.0186(12) -0.0019(12) Cl2 0.098(3) 0.085(2) 0.127(3) -0.073(2) 0.069(3) -0.0260(19) Cl3 0.0384(13) 0.0614(17) 0.0506(14) -0.0113(12) 0.0147(11) -0.0031(11) S1 0.0258(10) 0.0313(11) 0.0186(9) 0.0058(8) 0.0116(8) -0.0008(8) O1 0.021(3) 0.032(3) 0.023(3) 0.007(2) 0.012(2) 0.000(2) O4 0.056(4) 0.046(4) 0.055(4) 0.011(3) 0.040(4) 0.014(3) O3 0.051(4) 0.041(4) 0.050(4) -0.008(3) 0.021(3) -0.008(3) O2 0.079(5) 0.041(4) 0.022(3) 0.009(3) 0.022(3) 0.011(3) O5 0.034(3) 0.033(3) 0.035(3) 0.007(3) 0.018(3) 0.010(2) O6 0.051(4) 0.046(4) 0.044(4) -0.018(3) 0.028(3) -0.007(3) N1 0.031(3) 0.030(4) 0.018(3) 0.002(3) 0.012(3) -0.001(3) N2 0.031(4) 0.028(4) 0.022(3) 0.003(3) 0.010(3) -0.001(3) N3 0.050(6) 0.034(6) 0.031(5) 0.000 0.026(5) 0.000 C1 0.029(4) 0.024(4) 0.018(3) 0.001(3) 0.014(3) 0.002(3) C4 0.045(5) 0.027(5) 0.028(4) 0.005(3) 0.023(4) 0.005(4) C3 0.033(5) 0.038(5) 0.028(4) 0.004(4) 0.015(4) -0.007(4) C2 0.047(5) 0.030(5) 0.019(4) 0.005(3) 0.015(4) 0.008(4) C5 0.027(4) 0.030(5) 0.023(4) 0.005(3) 0.009(3) 0.001(3) C6 0.037(5) 0.034(5) 0.018(4) -0.006(3) 0.017(3) -0.007(4) C8 0.036(5) 0.032(5) 0.033(4) -0.001(4) 0.020(4) 0.000(4) C10 0.023(4) 0.020(4) 0.017(3) 0.003(3) 0.010(3) -0.001(3) C11 0.028(4) 0.024(4) 0.018(3) 0.002(3) 0.011(3) 0.004(3) C12 0.022(4) 0.024(4) 0.019(4) -0.006(3) 0.008(3) -0.006(3) C13 0.037(5) 0.049(6) 0.026(4) 0.014(4) 0.009(4) -0.001(4) C14 0.082(8) 0.034(6) 0.032(5) 0.004(4) 0.002(5) -0.008(5) C15 0.085(8) 0.042(6) 0.035(5) -0.001(5) 0.006(5) 0.032(6) C16 0.050(6) 0.073(8) 0.031(5) -0.019(5) 0.011(5) 0.014(5) C17 0.031(5) 0.046(6) 0.027(4) 0.003(4) 0.005(4) 0.002(4) C20 0.21(2) 0.024(9) 0.066(11) 0.000 0.063(14) 0.000 C21 0.080(18) 0.084(18) 0.11(2) 0.013(17) 0.080(18) 0.037(15) C22 0.094(18) 0.038(14) 0.082(17) -0.007(12) 0.046(15) -0.008(12) C23 0.071(15) 0.043(12) 0.050(12) 0.008(10) 0.040(12) -0.019(10) _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 W1 C4 2.012(8) . ? W1 C2 2.012(7) . ? W1 C3 2.022(9) . ? W1 C6 2.028(8) . ? W1 C5 2.033(8) . ? W1 C1 2.246(7) . ? Cl1 C8 1.746(8) . ? Cl2 C8 1.734(8) . ? Cl3 C8 1.737(8) . ? S1 C12 1.733(7) . ? S1 C10 1.756(7) . ? O1 C1 1.284(8) . ? O1 H1 0.8400 . ? O4 C4 1.157(9) . ? O3 C3 1.149(10) . ? O2 C2 1.144(9) . ? O5 C5 1.141(9) . ? O6 C6 1.143(9) . ? N1 C12 1.335(9) . ? N1 C11 1.362(9) . ? N2 C12 1.332(9) . ? N2 C13 1.459(10) . ? N2 C17 1.466(10) . ? N3 C21 1.462(13) . ? N3 C21 1.462(13) 2_655 ? N3 C23 1.476(13) 2_655 ? N3 C23 1.476(13) . ? N3 C20 1.490(13) . ? N3 C22 1.496(15) 2_655 ? N3 C22 1.496(15) . ? C1 C10 1.437(9) . ? C8 H8 1.0000 . ? C10 C11 1.353(10) . ? C11 H11 0.9500 . ? C13 C14 1.494(13) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.513(14) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.515(14) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.507(13) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C20 H20A 0.9801 . ? C20 H20B 0.9801 . ? C20 H20C 0.9801 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 C4 W1 C2 87.7(3) . . ? C4 W1 C3 92.5(3) . . ? C2 W1 C3 92.4(3) . . ? C4 W1 C6 91.8(3) . . ? C2 W1 C6 92.5(3) . . ? C3 W1 C6 173.6(3) . . ? C4 W1 C5 174.8(3) . . ? C2 W1 C5 87.3(3) . . ? C3 W1 C5 86.4(3) . . ? C6 W1 C5 89.7(3) . . ? C4 W1 C1 91.3(3) . . ? C2 W1 C1 178.9(3) . . ? C3 W1 C1 87.9(3) . . ? C6 W1 C1 87.3(3) . . ? C5 W1 C1 93.7(3) . . ? C12 S1 C10 88.9(3) . . ? C1 O1 H1 109.5 . . ? C12 N1 C11 108.1(6) . . ? C12 N2 C13 121.7(7) . . ? C12 N2 C17 122.1(6) . . ? C13 N2 C17 113.0(6) . . ? C21 N3 C21 155(2) . 2_655 ? C21 N3 C23 52.9(13) . 2_655 ? C21 N3 C23 113.0(13) 2_655 2_655 ? C21 N3 C23 113.0(13) . . ? C21 N3 C23 52.9(13) 2_655 . ? C23 N3 C23 121.2(17) 2_655 . ? C21 N3 C20 102.5(12) . . ? C21 N3 C20 102.5(12) 2_655 . ? C23 N3 C20 119.4(9) 2_655 . ? C23 N3 C20 119.4(9) . . ? C21 N3 C22 105.3(15) . 2_655 ? C21 N3 C22 66.5(14) 2_655 2_655 ? C23 N3 C22 52.6(12) 2_655 2_655 ? C23 N3 C22 107.7(12) . 2_655 ? C20 N3 C22 108.0(9) . 2_655 ? C21 N3 C22 66.5(14) . . ? C21 N3 C22 105.3(15) 2_655 . ? C23 N3 C22 107.7(12) 2_655 . ? C23 N3 C22 52.6(12) . . ? C20 N3 C22 108.0(9) . . ? C22 N3 C22 143.9(19) 2_655 . ? O1 C1 C10 110.4(6) . . ? O1 C1 W1 125.2(5) . . ? C10 C1 W1 124.4(5) . . ? O4 C4 W1 176.6(7) . . ? O3 C3 W1 177.4(7) . . ? O2 C2 W1 179.0(9) . . ? O5 C5 W1 176.5(7) . . ? O6 C6 W1 177.8(7) . . ? Cl2 C8 Cl3 111.9(5) . . ? Cl2 C8 Cl1 111.2(5) . . ? Cl3 C8 Cl1 111.4(5) . . ? Cl2 C8 H8 107.4 . . ? Cl3 C8 H8 107.4 . . ? Cl1 C8 H8 107.4 . . ? C11 C10 C1 132.5(6) . . ? C11 C10 S1 107.9(5) . . ? C1 C10 S1 119.5(5) . . ? C10 C11 N1 119.3(7) . . ? C10 C11 H11 120.3 . . ? N1 C11 H11 120.3 . . ? N2 C12 N1 122.0(7) . . ? N2 C12 S1 122.2(6) . . ? N1 C12 S1 115.7(5) . . ? N2 C13 C14 109.4(7) . . ? N2 C13 H13A 109.8 . . ? C14 C13 H13A 109.8 . . ? N2 C13 H13B 109.8 . . ? C14 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? C13 C14 C15 110.1(8) . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? C13 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.2 . . ? C14 C15 C16 110.9(8) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C17 C16 C15 110.4(8) . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16B 109.6 . . ? C15 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? N2 C17 C16 109.8(8) . . ? N2 C17 H17A 109.7 . . ? C16 C17 H17A 109.7 . . ? N2 C17 H17B 109.7 . . ? C16 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? N3 C20 H20A 109.5 . . ? N3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? N3 C21 H21A 109.5 . . ? N3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N3 C22 H22A 109.5 . . ? N3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N3 C23 H23A 109.5 . . ? N3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 W1 C1 O1 -135.5(7) . . . . ? C3 W1 C1 O1 132.1(7) . . . . ? C6 W1 C1 O1 -43.7(6) . . . . ? C5 W1 C1 O1 45.8(6) . . . . ? C4 W1 C1 C10 42.7(6) . . . . ? C3 W1 C1 C10 -49.7(6) . . . . ? C6 W1 C1 C10 134.5(6) . . . . ? C5 W1 C1 C10 -136.0(6) . . . . ? O1 C1 C10 C11 -176.9(8) . . . . ? W1 C1 C10 C11 4.7(12) . . . . ? O1 C1 C10 S1 0.8(9) . . . . ? W1 C1 C10 S1 -177.6(4) . . . . ? C12 S1 C10 C11 -0.2(6) . . . . ? C12 S1 C10 C1 -178.4(6) . . . . ? C1 C10 C11 N1 177.4(7) . . . . ? S1 C10 C11 N1 -0.5(9) . . . . ? C12 N1 C11 C10 1.0(9) . . . . ? C13 N2 C12 N1 -172.7(7) . . . . ? C17 N2 C12 N1 -14.3(11) . . . . ? C13 N2 C12 S1 9.0(10) . . . . ? C17 N2 C12 S1 167.4(6) . . . . ? C11 N1 C12 N2 -179.6(7) . . . . ? C11 N1 C12 S1 -1.1(8) . . . . ? C10 S1 C12 N2 179.2(7) . . . . ? C10 S1 C12 N1 0.8(6) . . . . ? C12 N2 C13 C14 99.7(9) . . . . ? C17 N2 C13 C14 -60.5(9) . . . . ? N2 C13 C14 C15 57.8(9) . . . . ? C13 C14 C15 C16 -56.0(10) . . . . ? C14 C15 C16 C17 54.5(11) . . . . ? C12 N2 C17 C16 -101.1(9) . . . . ? C13 N2 C17 C16 59.0(9) . . . . ? C15 C16 C17 N2 -54.8(10) . . . . ? 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 O1 H1 O1 0.84 1.61 2.418(9) 160.7 2_656 C8 H8 N1 1.00 2.14 3.091(10) 158.5 . _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.18 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 3.446 _refine_diff_density_min -1.245 _refine_diff_density_rms 0.216 #===END data_Compound-5 _database_code_depnum_ccdc_archive 'CCDC 744825' _audit_creation_method SHELXL-97 _chemical_name_systematic Chloro[methoxy(2-phenylthiazol-5-yl)methylidene]gold _chemical_name_common Chloro[(methoxy)(2-phenylthiazol-5-yl)carbene]gold(I) _chemical_melting_point 348 # Decomposition without melting. _chemical_formula_moiety 'C11 H9 Au Cl N O S' _chemical_formula_sum 'C11 H9 Au Cl N O S' _chemical_formula_weight 435.67 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.2229(11) _cell_length_b 11.5834(9) _cell_length_c 14.8108(11) _cell_angle_alpha 90.00 _cell_angle_beta 106.345(1) _cell_angle_gamma 90.00 _cell_volume 2341.5(3) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6899 _cell_measurement_theta_min 2.268 _cell_measurement_theta_max 26.389 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 12.947 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.190 _exptl_absorpt_correction_T_max 0.273 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13330 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 26.39 _reflns_number_total 4783 _reflns_number_gt 4444 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)' _computing_publication_material X-Seed _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^)+(0.0278P)^2^+0.3893P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4783 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0260 _refine_ls_R_factor_gt 0.0234 _refine_ls_wR_factor_ref 0.0560 _refine_ls_wR_factor_gt 0.0548 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 Au1A Au 0.844513(11) 0.780110(14) 0.174516(11) 0.01666(6) Uani 1 1 d . . . Au1B Au 0.968563(11) 0.623212(14) 0.052605(11) 0.01728(6) Uani 1 1 d . . . Cl1A Cl 0.92384(7) 0.68321(10) 0.30906(7) 0.0214(2) Uani 1 1 d . . . Cl1B Cl 1.10864(8) 0.72627(10) 0.06757(8) 0.0248(2) Uani 1 1 d . . . S1A S 0.58140(7) 0.90488(9) -0.06848(7) 0.0172(2) Uani 1 1 d . . . S1B S 0.64548(7) 0.49937(9) -0.04108(7) 0.0185(2) Uani 1 1 d . . . O1A O 0.7952(2) 0.9262(3) 0.0041(2) 0.0208(7) Uani 1 1 d . . . O1B O 0.8323(2) 0.4604(3) 0.0988(2) 0.0194(6) Uani 1 1 d . . . N1A N 0.5088(3) 0.7870(3) 0.0443(3) 0.0216(8) Uani 1 1 d . . . N1B N 0.6547(2) 0.6602(3) -0.1591(2) 0.0167(7) Uani 1 1 d . . . C1A C 0.7649(3) 0.8615(4) 0.0616(3) 0.0172(9) Uani 1 1 d . . . C1B C 0.8458(3) 0.5404(4) 0.0419(3) 0.0161(8) Uani 1 1 d . . . C10A C 0.6607(3) 0.8479(4) 0.0328(3) 0.0163(9) Uani 1 1 d . . . C10B C 0.7571(3) 0.5661(4) -0.0296(3) 0.0159(8) Uani 1 1 d . . . C11A C 0.6064(3) 0.7901(4) 0.0819(3) 0.0212(9) Uani 1 1 d . . . H11A H 0.6369 0.7537 0.1403 0.025 Uiso 1 1 calc R . . C11B C 0.7453(3) 0.6492(4) -0.0990(3) 0.0187(9) Uani 1 1 d . . . H11B H 0.7983 0.6961 -0.1042 0.022 Uiso 1 1 calc R . . C12A C 0.4845(3) 0.8449(4) -0.0359(3) 0.0170(9) Uani 1 1 d . . . C12B C 0.5936(3) 0.5871(4) -0.1374(3) 0.0155(8) Uani 1 1 d . . . C13A C 0.3826(3) 0.8594(3) -0.0932(3) 0.0162(9) Uani 1 1 d . . . C13B C 0.4891(3) 0.5791(4) -0.1889(3) 0.0163(9) Uani 1 1 d . . . C14A C 0.3592(3) 0.9195(4) -0.1777(3) 0.0189(9) Uani 1 1 d . . . H14A H 0.4098 0.9533 -0.1992 0.023 Uiso 1 1 calc R . . C14B C 0.4466(3) 0.6668(4) -0.2510(3) 0.0190(9) Uani 1 1 d . . . H14B H 0.4853 0.7298 -0.2609 0.023 Uiso 1 1 calc R . . C15A C 0.2617(3) 0.9306(4) -0.2312(3) 0.0216(9) Uani 1 1 d . . . H15A H 0.2458 0.9700 -0.2899 0.026 Uiso 1 1 calc R . . C15B C 0.3476(3) 0.6623(4) -0.2985(3) 0.0231(10) Uani 1 1 d . . . H15B H 0.3186 0.7228 -0.3404 0.028 Uiso 1 1 calc R . . C16A C 0.1883(3) 0.8835(4) -0.1978(3) 0.0196(9) Uani 1 1 d . . . H16A H 0.1218 0.8916 -0.2335 0.024 Uiso 1 1 calc R . . C16B C 0.2911(3) 0.5707(4) -0.2853(3) 0.0233(10) Uani 1 1 d . . . H16B H 0.2232 0.5686 -0.3177 0.028 Uiso 1 1 calc R . . C17A C 0.2109(3) 0.8251(4) -0.1135(3) 0.0209(9) Uani 1 1 d . . . H17A H 0.1600 0.7935 -0.0911 0.025 Uiso 1 1 calc R . . C17B C 0.3331(3) 0.4813(4) -0.2246(3) 0.0268(10) Uani 1 1 d . . . H17B H 0.2945 0.4172 -0.2167 0.032 Uiso 1 1 calc R . . C18A C 0.3076(3) 0.8126(4) -0.0612(3) 0.0176(9) Uani 1 1 d . . . H18A H 0.3229 0.7718 -0.0032 0.021 Uiso 1 1 calc R . . C18B C 0.4328(3) 0.4863(4) -0.1751(3) 0.0240(10) Uani 1 1 d . . . H18B H 0.4617 0.4265 -0.1324 0.029 Uiso 1 1 calc R . . C7A C 0.8998(3) 0.9517(4) 0.0252(3) 0.0251(10) Uani 1 1 d . . . H7A H 0.9291 0.9520 0.0935 0.038 Uiso 1 1 calc R . . H7B H 0.9087 1.0275 -0.0005 0.038 Uiso 1 1 calc R . . H7C H 0.9317 0.8926 -0.0034 0.038 Uiso 1 1 calc R . . C7B C 0.9173(3) 0.4221(4) 0.1742(3) 0.0219(10) Uani 1 1 d . . . H7D H 0.9647 0.3849 0.1467 0.033 Uiso 1 1 calc R . . H7E H 0.8961 0.3668 0.2146 0.033 Uiso 1 1 calc R . . H7F H 0.9480 0.4888 0.2117 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1A 0.01423(9) 0.01604(9) 0.01780(10) -0.00184(6) 0.00137(7) 0.00017(6) Au1B 0.01328(9) 0.02011(10) 0.01669(10) -0.00031(6) 0.00132(7) -0.00121(6) Cl1A 0.0189(5) 0.0227(6) 0.0200(5) 0.0006(4) 0.0013(4) 0.0017(4) Cl1B 0.0162(5) 0.0326(6) 0.0223(6) 0.0050(5) -0.0002(4) -0.0066(5) S1A 0.0157(5) 0.0181(5) 0.0175(5) 0.0009(4) 0.0041(4) 0.0002(4) S1B 0.0137(5) 0.0209(6) 0.0191(5) 0.0021(4) 0.0019(4) -0.0012(4) O1A 0.0171(15) 0.0236(17) 0.0199(16) 0.0017(13) 0.0020(12) 0.0021(13) O1B 0.0158(14) 0.0183(16) 0.0213(16) 0.0001(13) 0.0005(12) 0.0012(13) N1A 0.0191(18) 0.021(2) 0.023(2) 0.0055(16) 0.0045(16) 0.0004(16) N1B 0.0186(18) 0.0159(18) 0.0160(18) -0.0003(14) 0.0053(15) -0.0008(15) C1A 0.021(2) 0.015(2) 0.016(2) -0.0039(17) 0.0049(18) -0.0011(18) C1B 0.016(2) 0.014(2) 0.018(2) -0.0057(17) 0.0044(17) 0.0005(17) C10A 0.018(2) 0.0109(19) 0.017(2) -0.0038(16) 0.0008(17) -0.0006(17) C10B 0.0136(19) 0.015(2) 0.020(2) -0.0031(17) 0.0059(17) 0.0006(17) C11A 0.020(2) 0.022(2) 0.020(2) 0.0031(18) 0.0032(18) 0.0010(19) C11B 0.016(2) 0.015(2) 0.025(2) -0.0038(18) 0.0048(18) 0.0006(17) C12A 0.018(2) 0.011(2) 0.022(2) -0.0033(17) 0.0062(18) -0.0018(17) C12B 0.016(2) 0.016(2) 0.014(2) -0.0008(17) 0.0041(17) 0.0045(17) C13A 0.015(2) 0.012(2) 0.020(2) -0.0043(17) 0.0026(17) -0.0006(17) C13B 0.016(2) 0.019(2) 0.015(2) -0.0038(17) 0.0059(17) 0.0025(17) C14A 0.019(2) 0.018(2) 0.021(2) -0.0001(18) 0.0083(18) -0.0026(18) C14B 0.021(2) 0.019(2) 0.017(2) -0.0012(17) 0.0057(18) 0.0004(18) C15A 0.023(2) 0.024(2) 0.016(2) 0.0017(18) 0.0026(18) 0.002(2) C15B 0.023(2) 0.029(3) 0.015(2) 0.0010(19) 0.0009(18) 0.009(2) C16A 0.017(2) 0.018(2) 0.020(2) -0.0040(17) -0.0005(18) 0.0014(18) C16B 0.015(2) 0.035(3) 0.020(2) -0.003(2) 0.0046(18) 0.006(2) C17A 0.022(2) 0.018(2) 0.026(2) -0.0028(19) 0.0111(19) -0.0051(19) C17B 0.016(2) 0.033(3) 0.030(3) 0.001(2) 0.004(2) -0.002(2) C18A 0.018(2) 0.015(2) 0.020(2) 0.0000(17) 0.0053(17) -0.0008(18) C18B 0.019(2) 0.028(3) 0.025(2) 0.006(2) 0.0063(19) 0.000(2) C7A 0.015(2) 0.028(3) 0.033(3) 0.000(2) 0.0090(19) -0.006(2) C7B 0.018(2) 0.020(2) 0.022(2) 0.0016(18) -0.0036(18) 0.0043(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 Au1A C1A 1.976(4) . ? Au1A Cl1A 2.2888(10) . ? Au1A H11A 2.8688 . ? Au1A Au1B 3.3866(3) . ? Au1B C1B 1.959(4) . ? Au1B Cl1B 2.2792(11) . ? Au1B H11B 2.9671 . ? Au1B Au1B 3.4871(4) 3_765 ? S1A C12A 1.730(4) . ? S1A C10A 1.734(4) . ? S1B C10B 1.730(4) . ? S1B C12B 1.738(4) . ? O1A C1A 1.296(5) . ? O1A C7A 1.461(5) . ? O1B C1B 1.302(5) . ? O1B C7B 1.465(5) . ? N1A C12A 1.323(5) . ? N1A C11A 1.343(6) . ? N1B C12B 1.316(5) . ? N1B C11B 1.350(5) . ? C1A C10A 1.430(6) . ? C1B C10B 1.433(6) . ? C10A C11A 1.374(6) . ? C10B C11B 1.383(6) . ? C11A H11A 0.9500 . ? C11B H11B 0.9500 . ? C12A C13A 1.468(6) . ? C12B C13B 1.469(6) . ? C13A C14A 1.389(6) . ? C13A C18A 1.393(6) . ? C13B C14B 1.389(6) . ? C13B C18B 1.390(6) . ? C14A C15A 1.396(6) . ? C14A H14A 0.9500 . ? C14B C15B 1.387(6) . ? C14B H14B 0.9500 . ? C15A C16A 1.386(6) . ? C15A H15A 0.9500 . ? C15B C16B 1.378(7) . ? C15B H15B 0.9500 . ? C16A C17A 1.376(6) . ? C16A H16A 0.9500 . ? C16B C17B 1.391(6) . ? C16B H16B 0.9500 . ? C17A C18A 1.383(6) . ? C17A H17A 0.9500 . ? C17B C18B 1.402(6) . ? C17B H17B 0.9500 . ? C18A H18A 0.9500 . ? C18B H18B 0.9500 . ? C7A H7A 0.9800 . ? C7A H7B 0.9800 . ? C7A H7C 0.9800 . ? C7B H7D 0.9800 . ? C7B H7E 0.9800 . ? C7B H7F 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 C1A Au1A Cl1A 174.78(13) . . ? C1A Au1A H11A 65.5 . . ? Cl1A Au1A H11A 109.4 . . ? C1A Au1A Au1B 93.75(12) . . ? Cl1A Au1A Au1B 89.88(3) . . ? H11A Au1A Au1B 120.9 . . ? C1B Au1B Cl1B 177.53(12) . . ? C1B Au1B H11B 64.1 . . ? Cl1B Au1B H11B 115.2 . . ? C1B Au1B Au1A 73.74(12) . . ? Cl1B Au1B Au1A 103.85(3) . . ? H11B Au1B Au1A 80.3 . . ? C1B Au1B Au1B 84.12(12) . 3_765 ? Cl1B Au1B Au1B 98.34(3) . 3_765 ? H11B Au1B Au1B 98.0 . 3_765 ? Au1A Au1B Au1B 156.223(8) . 3_765 ? C12A S1A C10A 88.9(2) . . ? C10B S1B C12B 89.1(2) . . ? C1A O1A C7A 119.0(3) . . ? C1B O1B C7B 117.9(3) . . ? C12A N1A C11A 109.7(4) . . ? C12B N1B C11B 110.6(4) . . ? O1A C1A C10A 112.2(4) . . ? O1A C1A Au1A 127.9(3) . . ? C10A C1A Au1A 119.9(3) . . ? O1B C1B C10B 111.5(4) . . ? O1B C1B Au1B 125.9(3) . . ? C10B C1B Au1B 122.6(3) . . ? C11A C10A C1A 125.8(4) . . ? C11A C10A S1A 108.5(3) . . ? C1A C10A S1A 125.6(3) . . ? C11B C10B C1B 126.2(4) . . ? C11B C10B S1B 108.8(3) . . ? C1B C10B S1B 125.0(3) . . ? N1A C11A C10A 117.6(4) . . ? N1A C11A H11A 121.2 . . ? C10A C11A H11A 121.2 . . ? N1B C11B C10B 116.7(4) . . ? N1B C11B H11B 121.7 . . ? C10B C11B H11B 121.7 . . ? N1A C12A C13A 122.9(4) . . ? N1A C12A S1A 115.2(3) . . ? C13A C12A S1A 121.8(3) . . ? N1B C12B C13B 123.7(4) . . ? N1B C12B S1B 114.8(3) . . ? C13B C12B S1B 121.5(3) . . ? C14A C13A C18A 119.3(4) . . ? C14A C13A C12A 121.7(4) . . ? C18A C13A C12A 119.0(4) . . ? C14B C13B C18B 120.1(4) . . ? C14B C13B C12B 119.0(4) . . ? C18B C13B C12B 120.9(4) . . ? C13A C14A C15A 120.4(4) . . ? C13A C14A H14A 119.8 . . ? C15A C14A H14A 119.8 . . ? C15B C14B C13B 119.9(4) . . ? C15B C14B H14B 120.0 . . ? C13B C14B H14B 120.0 . . ? C16A C15A C14A 119.2(4) . . ? C16A C15A H15A 120.4 . . ? C14A C15A H15A 120.4 . . ? C16B C15B C14B 120.5(4) . . ? C16B C15B H15B 119.8 . . ? C14B C15B H15B 119.8 . . ? C17A C16A C15A 120.7(4) . . ? C17A C16A H16A 119.6 . . ? C15A C16A H16A 119.6 . . ? C15B C16B C17B 120.2(4) . . ? C15B C16B H16B 119.9 . . ? C17B C16B H16B 119.9 . . ? C16A C17A C18A 120.1(4) . . ? C16A C17A H17A 120.0 . . ? C18A C17A H17A 120.0 . . ? C16B C17B C18B 119.6(4) . . ? C16B C17B H17B 120.2 . . ? C18B C17B H17B 120.2 . . ? C17A C18A C13A 120.3(4) . . ? C17A C18A H18A 119.9 . . ? C13A C18A H18A 119.9 . . ? C13B C18B C17B 119.7(4) . . ? C13B C18B H18B 120.2 . . ? C17B C18B H18B 120.2 . . ? O1A C7A H7A 109.5 . . ? O1A C7A H7B 109.5 . . ? H7A C7A H7B 109.5 . . ? O1A C7A H7C 109.5 . . ? H7A C7A H7C 109.5 . . ? H7B C7A H7C 109.5 . . ? O1B C7B H7D 109.5 . . ? O1B C7B H7E 109.5 . . ? H7D C7B H7E 109.5 . . ? O1B C7B H7F 109.5 . . ? H7D C7B H7F 109.5 . . ? H7E C7B H7F 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 C1A Au1A Au1B C1B -83.88(17) . . . . ? Cl1A Au1A Au1B C1B 92.35(13) . . . . ? H11A Au1A Au1B C1B -20.4 . . . . ? C1A Au1A Au1B Cl1B 95.56(12) . . . . ? Cl1A Au1A Au1B Cl1B -88.20(4) . . . . ? H11A Au1A Au1B Cl1B 159.1 . . . . ? C1A Au1A Au1B H11B -18.2 . . . . ? Cl1A Au1A Au1B H11B 158.1 . . . . ? H11A Au1A Au1B H11B 45.4 . . . . ? C1A Au1A Au1B Au1B -105.96(12) . . . 3_765 ? Cl1A Au1A Au1B Au1B 70.28(3) . . . 3_765 ? H11A Au1A Au1B Au1B -42.4 . . . 3_765 ? C7A O1A C1A C10A 178.1(4) . . . . ? C7A O1A C1A Au1A -4.7(6) . . . . ? H11A Au1A C1A O1A 178.2 . . . . ? Au1B Au1A C1A O1A -59.4(4) . . . . ? H11A Au1A C1A C10A -4.8 . . . . ? Au1B Au1A C1A C10A 117.6(3) . . . . ? C7B O1B C1B C10B 178.1(3) . . . . ? C7B O1B C1B Au1B -4.6(5) . . . . ? H11B Au1B C1B O1B -177.4 . . . . ? Au1A Au1B C1B O1B -90.5(3) . . . . ? Au1B Au1B C1B O1B 80.7(3) 3_765 . . . ? H11B Au1B C1B C10B -0.4 . . . . ? Au1A Au1B C1B C10B 86.5(3) . . . . ? Au1B Au1B C1B C10B -102.3(3) 3_765 . . . ? O1A C1A C10A C11A -176.0(4) . . . . ? Au1A C1A C10A C11A 6.6(6) . . . . ? O1A C1A C10A S1A 2.1(5) . . . . ? Au1A C1A C10A S1A -175.3(2) . . . . ? C12A S1A C10A C11A -0.6(3) . . . . ? C12A S1A C10A C1A -179.0(4) . . . . ? O1B C1B C10B C11B 177.7(4) . . . . ? Au1B C1B C10B C11B 0.3(6) . . . . ? O1B C1B C10B S1B -0.6(5) . . . . ? Au1B C1B C10B S1B -178.0(2) . . . . ? C12B S1B C10B C11B 0.4(3) . . . . ? C12B S1B C10B C1B 179.0(4) . . . . ? C12A N1A C11A C10A -0.9(6) . . . . ? C1A C10A C11A N1A 179.4(4) . . . . ? S1A C10A C11A N1A 1.0(5) . . . . ? C12B N1B C11B C10B 0.7(5) . . . . ? C1B C10B C11B N1B -179.2(4) . . . . ? S1B C10B C11B N1B -0.7(5) . . . . ? C11A N1A C12A C13A -178.8(4) . . . . ? C11A N1A C12A S1A 0.4(5) . . . . ? C10A S1A C12A N1A 0.1(3) . . . . ? C10A S1A C12A C13A 179.3(4) . . . . ? C11B N1B C12B C13B 179.2(4) . . . . ? C11B N1B C12B S1B -0.3(5) . . . . ? C10B S1B C12B N1B -0.1(3) . . . . ? C10B S1B C12B C13B -179.6(4) . . . . ? N1A C12A C13A C14A -179.2(4) . . . . ? S1A C12A C13A C14A 1.7(6) . . . . ? N1A C12A C13A C18A 1.5(6) . . . . ? S1A C12A C13A C18A -177.6(3) . . . . ? N1B C12B C13B C14B -13.7(6) . . . . ? S1B C12B C13B C14B 165.7(3) . . . . ? N1B C12B C13B C18B 167.2(4) . . . . ? S1B C12B C13B C18B -13.4(6) . . . . ? C18A C13A C14A C15A -1.6(6) . . . . ? C12A C13A C14A C15A 179.2(4) . . . . ? C18B C13B C14B C15B 0.7(6) . . . . ? C12B C13B C14B C15B -178.4(4) . . . . ? C13A C14A C15A C16A 1.7(7) . . . . ? C13B C14B C15B C16B -0.7(7) . . . . ? C14A C15A C16A C17A -0.8(7) . . . . ? C14B C15B C16B C17B -0.5(7) . . . . ? C15A C16A C17A C18A -0.3(6) . . . . ? C15B C16B C17B C18B 1.6(7) . . . . ? C16A C17A C18A C13A 0.4(6) . . . . ? C14A C13A C18A C17A 0.5(6) . . . . ? C12A C13A C18A C17A 179.8(4) . . . . ? C14B C13B C18B C17B 0.4(7) . . . . ? C12B C13B C18B C17B 179.5(4) . . . . ? C16B C17B C18B C13B -1.6(7) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.211 _refine_diff_density_min -0.625 _refine_diff_density_rms 0.154 #===END data_Compound-6a _database_code_depnum_ccdc_archive 'CCDC 744826' _audit_creation_method SHELXL-97 _chemical_name_systematic ;cis-dicarbonylchloro{[2-(1-piperidinyl)thiazol-5- yl]methylidyne}-cis-bis(pyridine)tungsten ; _chemical_name_common ;Chlorodicarbonylbis(pyridine)[2-(1-piperidinyl)thiazol-5- ylcarbyne]tungsten(IV)' ; _chemical_melting_point 346 _chemical_formula_moiety 'C21 H21 Cl N4 O2 S W' _chemical_formula_sum 'C21 H21 Cl N4 O2 S W' _chemical_formula_weight 612.78 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.657(2) _cell_length_b 8.917(2) _cell_length_c 16.718(4) _cell_angle_alpha 98.687(4) _cell_angle_beta 96.490(4) _cell_angle_gamma 118.054(3) _cell_volume 1100.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 7715 _cell_measurement_theta_min 2.521 _cell_measurement_theta_max 26.524 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.849 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 596 _exptl_absorpt_coefficient_mu 5.490 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.627 _exptl_absorpt_correction_T_max 0.852 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11537 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.52 _diffrn_reflns_theta_max 26.62 _reflns_number_total 4490 _reflns_number_gt 4202 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)' _computing_publication_material X-Seed _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^)+(0.0401P)^2^+0.2815P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4490 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0671 _refine_ls_wR_factor_gt 0.0661 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 W1 W 0.416856(19) 0.656552(17) 0.197700(9) 0.01613(7) Uani 1 1 d . . . Cl1 Cl 0.20754(14) 0.44304(13) 0.06559(7) 0.0278(2) Uani 1 1 d . . . O1 O 0.6414(4) 0.4660(4) 0.1791(2) 0.0316(7) Uani 1 1 d . . . N1 N 0.7466(4) 1.0664(4) 0.5107(2) 0.0194(7) Uani 1 1 d . . . C1 C 0.5712(5) 0.8021(5) 0.2958(2) 0.0166(8) Uani 1 1 d . . . O2 O 0.2302(5) 0.4026(4) 0.3110(2) 0.0380(8) Uani 1 1 d . . . N2 N 1.0490(4) 1.2854(4) 0.5396(2) 0.0211(7) Uani 1 1 d . . . S1 S 0.90733(13) 1.06099(12) 0.38840(6) 0.0182(2) Uani 1 1 d . . . N3 N 0.5513(4) 0.8439(4) 0.1169(2) 0.0189(7) Uani 1 1 d . . . N4 N 0.2403(4) 0.7804(4) 0.1994(2) 0.0183(7) Uani 1 1 d . . . C10 C 0.6768(5) 0.9130(5) 0.3734(3) 0.0182(8) Uani 1 1 d . . . C11 C 0.6225(5) 0.9398(5) 0.4453(2) 0.0195(8) Uani 1 1 d . . . H11 H 0.5013 0.8718 0.4493 0.023 Uiso 1 1 calc R . . C12 C 0.9040(5) 1.1469(5) 0.4898(2) 0.0169(8) Uani 1 1 d . . . C13 C 1.0493(6) 1.3466(5) 0.6265(2) 0.0221(9) Uani 1 1 d . . . H13A H 1.1204 1.3140 0.6633 0.027 Uiso 1 1 calc R . . H13B H 0.9252 1.2903 0.6355 0.027 Uiso 1 1 calc R . . C14 C 1.1289(5) 1.5428(5) 0.6469(3) 0.0249(9) Uani 1 1 d . . . H14A H 1.1391 1.5844 0.7066 0.030 Uiso 1 1 calc R . . H14B H 1.0478 1.5732 0.6155 0.030 Uiso 1 1 calc R . . C15 C 1.3131(6) 1.6351(5) 0.6259(3) 0.0296(10) Uani 1 1 d . . . H15A H 1.3563 1.7621 0.6355 0.036 Uiso 1 1 calc R . . H15B H 1.3988 1.6182 0.6626 0.036 Uiso 1 1 calc R . . C16 C 1.3055(6) 1.5640(5) 0.5363(3) 0.0262(9) Uani 1 1 d . . . H16A H 1.4281 1.6179 0.5254 0.031 Uiso 1 1 calc R . . H16B H 1.2332 1.5956 0.4995 0.031 Uiso 1 1 calc R . . C17 C 1.2236(5) 1.3661(5) 0.5166(3) 0.0211(8) Uani 1 1 d . . . H17A H 1.2094 1.3218 0.4568 0.025 Uiso 1 1 calc R . . H17B H 1.3043 1.3346 0.5476 0.025 Uiso 1 1 calc R . . C21 C 0.5629(6) 0.5387(5) 0.1858(2) 0.0219(9) Uani 1 1 d . . . C22 C 0.2930(6) 0.4927(5) 0.2673(3) 0.0260(9) Uani 1 1 d . . . C31 C 0.5695(6) 0.7914(5) 0.0408(3) 0.0236(9) Uani 1 1 d . . . H31 H 0.5093 0.6698 0.0162 0.028 Uiso 1 1 calc R . . C32 C 0.6726(6) 0.9074(6) -0.0034(3) 0.0301(10) Uani 1 1 d . . . H32 H 0.6849 0.8657 -0.0567 0.036 Uiso 1 1 calc R . . C33 C 0.7576(6) 1.0856(6) 0.0317(3) 0.0310(10) Uani 1 1 d . . . H33 H 0.8292 1.1680 0.0029 0.037 Uiso 1 1 calc R . . C34 C 0.7362(6) 1.1406(5) 0.1092(3) 0.0277(9) Uani 1 1 d . . . H34 H 0.7913 1.2618 0.1341 0.033 Uiso 1 1 calc R . . C35 C 0.6341(5) 1.0180(5) 0.1499(3) 0.0226(8) Uani 1 1 d . . . H35 H 0.6211 1.0571 0.2035 0.027 Uiso 1 1 calc R . . C41 C 0.2878(6) 0.9209(5) 0.2604(3) 0.0242(9) Uani 1 1 d . . . H41 H 0.3877 0.9566 0.3037 0.029 Uiso 1 1 calc R . . C42 C 0.2000(6) 1.0159(5) 0.2638(3) 0.0257(9) Uani 1 1 d . . . H42 H 0.2404 1.1152 0.3079 0.031 Uiso 1 1 calc R . . C43 C 0.0522(6) 0.9644(6) 0.2022(3) 0.0294(10) Uani 1 1 d . . . H43 H -0.0099 1.0284 0.2023 0.035 Uiso 1 1 calc R . . C44 C -0.0022(6) 0.8177(6) 0.1407(3) 0.0306(10) Uani 1 1 d . . . H44 H -0.1047 0.7772 0.0981 0.037 Uiso 1 1 calc R . . C45 C 0.0940(5) 0.7293(5) 0.1414(2) 0.0227(9) Uani 1 1 d . . . H45 H 0.0540 0.6277 0.0988 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 W1 0.01674(9) 0.01150(9) 0.01754(10) 0.00214(6) 0.00218(6) 0.00561(7) Cl1 0.0232(5) 0.0210(5) 0.0281(5) -0.0061(4) -0.0027(4) 0.0074(4) O1 0.0382(18) 0.0308(17) 0.0333(18) 0.0009(14) 0.0028(14) 0.0259(16) N1 0.0192(17) 0.0161(16) 0.0189(17) 0.0039(13) 0.0049(14) 0.0055(14) C1 0.0173(19) 0.0143(17) 0.020(2) 0.0046(15) 0.0061(16) 0.0088(15) O2 0.048(2) 0.0306(17) 0.050(2) 0.0222(16) 0.0278(18) 0.0234(16) N2 0.0203(17) 0.0168(16) 0.0189(17) 0.0026(13) 0.0046(14) 0.0038(14) S1 0.0178(5) 0.0161(4) 0.0192(5) 0.0035(4) 0.0055(4) 0.0071(4) N3 0.0187(16) 0.0190(16) 0.0194(17) 0.0039(13) 0.0027(13) 0.0101(14) N4 0.0154(16) 0.0170(16) 0.0201(17) 0.0059(13) 0.0044(13) 0.0057(13) C10 0.0169(19) 0.0161(18) 0.027(2) 0.0094(16) 0.0073(16) 0.0111(16) C11 0.022(2) 0.0121(17) 0.024(2) 0.0045(15) 0.0042(16) 0.0082(16) C12 0.0180(19) 0.0111(17) 0.019(2) 0.0022(15) 0.0018(15) 0.0064(15) C13 0.023(2) 0.0163(19) 0.019(2) 0.0010(15) 0.0035(16) 0.0045(17) C14 0.024(2) 0.020(2) 0.029(2) 0.0012(17) 0.0005(18) 0.0114(18) C15 0.027(2) 0.0133(18) 0.038(3) 0.0010(17) -0.002(2) 0.0048(17) C16 0.019(2) 0.018(2) 0.037(3) 0.0125(18) 0.0065(18) 0.0040(17) C17 0.0192(19) 0.0159(18) 0.026(2) 0.0047(16) 0.0045(16) 0.0071(16) C21 0.026(2) 0.0185(19) 0.018(2) -0.0001(15) 0.0021(16) 0.0095(18) C22 0.027(2) 0.018(2) 0.033(2) 0.0061(18) 0.0094(19) 0.0110(18) C31 0.024(2) 0.022(2) 0.023(2) 0.0017(16) 0.0020(17) 0.0115(18) C32 0.033(2) 0.033(2) 0.027(2) 0.0092(19) 0.0098(19) 0.017(2) C33 0.030(2) 0.032(2) 0.031(2) 0.015(2) 0.011(2) 0.011(2) C34 0.030(2) 0.019(2) 0.031(2) 0.0074(18) 0.0075(19) 0.0094(18) C35 0.023(2) 0.0196(19) 0.026(2) 0.0046(16) 0.0050(17) 0.0111(17) C41 0.020(2) 0.022(2) 0.027(2) 0.0033(17) 0.0025(17) 0.0091(17) C42 0.025(2) 0.022(2) 0.032(2) 0.0007(18) 0.0069(18) 0.0152(18) C43 0.033(2) 0.039(3) 0.029(2) 0.011(2) 0.013(2) 0.025(2) C44 0.026(2) 0.044(3) 0.023(2) 0.006(2) -0.0004(18) 0.021(2) C45 0.023(2) 0.026(2) 0.019(2) 0.0031(16) 0.0039(17) 0.0130(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 W1 C1 1.841(4) . ? W1 C22 1.990(4) . ? W1 C21 1.996(4) . ? W1 N4 2.269(3) . ? W1 N3 2.276(3) . ? W1 Cl1 2.5232(11) . ? O1 C21 1.142(5) . ? N1 C12 1.325(5) . ? N1 C11 1.359(5) . ? C1 C10 1.411(5) . ? O2 C22 1.154(5) . ? N2 C12 1.337(5) . ? N2 C17 1.464(5) . ? N2 C13 1.472(5) . ? S1 C10 1.760(4) . ? S1 C12 1.762(4) . ? N3 C31 1.340(5) . ? N3 C35 1.354(5) . ? N4 C45 1.340(5) . ? N4 C41 1.347(5) . ? C10 C11 1.367(6) . ? C11 H11 0.9500 . ? C13 C14 1.511(5) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.524(6) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.518(6) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.523(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C31 C32 1.387(6) . ? C31 H31 0.9500 . ? C32 C33 1.390(6) . ? C32 H32 0.9500 . ? C33 C34 1.378(6) . ? C33 H33 0.9500 . ? C34 C35 1.376(6) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C41 C42 1.378(6) . ? C41 H41 0.9500 . ? C42 C43 1.385(6) . ? C42 H42 0.9500 . ? C43 C44 1.376(6) . ? C43 H43 0.9500 . ? C44 C45 1.390(6) . ? C44 H44 0.9500 . ? C45 H45 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 C1 W1 C22 85.19(17) . . ? C1 W1 C21 90.27(16) . . ? C22 W1 C21 86.57(17) . . ? C1 W1 N4 94.46(14) . . ? C22 W1 N4 95.33(15) . . ? C21 W1 N4 175.03(13) . . ? C1 W1 N3 95.66(14) . . ? C22 W1 N3 178.39(14) . . ? C21 W1 N3 94.79(14) . . ? N4 W1 N3 83.25(12) . . ? C1 W1 Cl1 176.70(12) . . ? C22 W1 Cl1 92.64(13) . . ? C21 W1 Cl1 87.11(12) . . ? N4 W1 Cl1 88.21(9) . . ? N3 W1 Cl1 86.57(9) . . ? C12 N1 C11 110.2(3) . . ? C10 C1 W1 175.1(3) . . ? C12 N2 C17 122.7(3) . . ? C12 N2 C13 121.1(3) . . ? C17 N2 C13 115.4(3) . . ? C10 S1 C12 88.69(18) . . ? C31 N3 C35 117.7(3) . . ? C31 N3 W1 123.2(3) . . ? C35 N3 W1 118.7(3) . . ? C45 N4 C41 116.4(3) . . ? C45 N4 W1 124.8(3) . . ? C41 N4 W1 118.7(3) . . ? C11 C10 C1 128.5(4) . . ? C11 C10 S1 108.4(3) . . ? C1 C10 S1 122.8(3) . . ? N1 C11 C10 118.1(4) . . ? N1 C11 H11 120.9 . . ? C10 C11 H11 120.9 . . ? N1 C12 N2 123.9(4) . . ? N1 C12 S1 114.5(3) . . ? N2 C12 S1 121.6(3) . . ? N2 C13 C14 109.6(3) . . ? N2 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? N2 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? C13 C14 C15 111.9(3) . . ? C13 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? C16 C15 C14 110.8(4) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C17 111.3(3) . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? N2 C17 C16 110.0(3) . . ? N2 C17 H17A 109.7 . . ? C16 C17 H17A 109.7 . . ? N2 C17 H17B 109.7 . . ? C16 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? O1 C21 W1 177.7(4) . . ? O2 C22 W1 176.0(4) . . ? N3 C31 C32 122.7(4) . . ? N3 C31 H31 118.7 . . ? C32 C31 H31 118.7 . . ? C31 C32 C33 118.8(4) . . ? C31 C32 H32 120.6 . . ? C33 C32 H32 120.6 . . ? C34 C33 C32 118.8(4) . . ? C34 C33 H33 120.6 . . ? C32 C33 H33 120.6 . . ? C35 C34 C33 119.2(4) . . ? C35 C34 H34 120.4 . . ? C33 C34 H34 120.4 . . ? N3 C35 C34 122.8(4) . . ? N3 C35 H35 118.6 . . ? C34 C35 H35 118.6 . . ? N4 C41 C42 123.8(4) . . ? N4 C41 H41 118.1 . . ? C42 C41 H41 118.1 . . ? C41 C42 C43 119.0(4) . . ? C41 C42 H42 120.5 . . ? C43 C42 H42 120.5 . . ? C44 C43 C42 118.0(4) . . ? C44 C43 H43 121.0 . . ? C42 C43 H43 121.0 . . ? C43 C44 C45 119.5(4) . . ? C43 C44 H44 120.2 . . ? C45 C44 H44 120.2 . . ? N4 C45 C44 123.2(4) . . ? N4 C45 H45 118.4 . . ? C44 C45 H45 118.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 W1 N3 C31 142.1(3) . . . . ? C21 W1 N3 C31 51.4(3) . . . . ? N4 W1 N3 C31 -124.0(3) . . . . ? Cl1 W1 N3 C31 -35.4(3) . . . . ? C1 W1 N3 C35 -30.5(3) . . . . ? C21 W1 N3 C35 -121.2(3) . . . . ? N4 W1 N3 C35 63.4(3) . . . . ? Cl1 W1 N3 C35 152.0(3) . . . . ? C1 W1 N4 C45 -179.4(3) . . . . ? C22 W1 N4 C45 -93.8(3) . . . . ? N3 W1 N4 C45 85.4(3) . . . . ? Cl1 W1 N4 C45 -1.3(3) . . . . ? C1 W1 N4 C41 3.8(3) . . . . ? C22 W1 N4 C41 89.4(3) . . . . ? N3 W1 N4 C41 -91.4(3) . . . . ? Cl1 W1 N4 C41 -178.1(3) . . . . ? C12 S1 C10 C11 -1.3(3) . . . . ? C12 S1 C10 C1 172.7(3) . . . . ? C12 N1 C11 C10 1.9(5) . . . . ? C1 C10 C11 N1 -173.6(4) . . . . ? S1 C10 C11 N1 0.0(4) . . . . ? C11 N1 C12 N2 175.1(4) . . . . ? C11 N1 C12 S1 -2.9(4) . . . . ? C17 N2 C12 N1 176.6(4) . . . . ? C13 N2 C12 N1 7.4(6) . . . . ? C17 N2 C12 S1 -5.4(5) . . . . ? C13 N2 C12 S1 -174.6(3) . . . . ? C10 S1 C12 N1 2.5(3) . . . . ? C10 S1 C12 N2 -175.6(3) . . . . ? C12 N2 C13 C14 -133.9(4) . . . . ? C17 N2 C13 C14 56.2(5) . . . . ? N2 C13 C14 C15 -53.7(5) . . . . ? C13 C14 C15 C16 54.3(5) . . . . ? C14 C15 C16 C17 -53.9(5) . . . . ? C12 N2 C17 C16 133.9(4) . . . . ? C13 N2 C17 C16 -56.3(5) . . . . ? C15 C16 C17 N2 53.9(5) . . . . ? C35 N3 C31 C32 1.8(6) . . . . ? W1 N3 C31 C32 -170.9(3) . . . . ? N3 C31 C32 C33 -1.4(7) . . . . ? C31 C32 C33 C34 -0.1(7) . . . . ? C32 C33 C34 C35 1.1(7) . . . . ? C31 N3 C35 C34 -0.8(6) . . . . ? W1 N3 C35 C34 172.3(3) . . . . ? C33 C34 C35 N3 -0.7(7) . . . . ? C45 N4 C41 C42 -2.9(6) . . . . ? W1 N4 C41 C42 174.2(3) . . . . ? N4 C41 C42 C43 1.1(7) . . . . ? C41 C42 C43 C44 1.1(7) . . . . ? C42 C43 C44 C45 -1.4(7) . . . . ? C41 N4 C45 C44 2.6(6) . . . . ? W1 N4 C45 C44 -174.3(3) . . . . ? C43 C44 C45 N4 -0.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 2.535 _refine_diff_density_min -0.883 _refine_diff_density_rms 0.152 #===END data_Compound-6b _database_code_depnum_ccdc_archive 'CCDC 744827' _audit_creation_method SHELXL-97 _chemical_name_systematic ;cis-dicarbonylchloro[(2-phenylthiazol-5-yl)methylidyne]- cis-bis(pyridine)tungsten dichloromethane solvate ; _chemical_name_common ;chlorodicarbonylbis(pyridine)[(2-phenylthiazol-5-yl) carbyne]tungsten(IV) ; _chemical_melting_point 357 _chemical_formula_moiety 'C22 H16 Cl N3 O2 S W, C H2 Cl2' _chemical_formula_sum 'C23 H18 Cl3 N3 O2 S W' _chemical_formula_weight 690.66 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' S S 0.1246 0.1234 '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' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1923(7) _cell_length_b 9.2850(8) _cell_length_c 15.7035(13) _cell_angle_alpha 101.302(1) _cell_angle_beta 92.103(1) _cell_angle_gamma 105.720(1) _cell_volume 1259.41(18) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8881 _cell_measurement_theta_min 2.333 _cell_measurement_theta_max 26.433 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.821 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 5.013 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.469 _exptl_absorpt_correction_T_max 0.703 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13500 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 26.45 _reflns_number_total 5154 _reflns_number_gt 4908 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)' _computing_publication_material X-Seed _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^)+(0.0332P)^2^+0.3767P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5154 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0579 _refine_ls_wR_factor_gt 0.0572 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.081 _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 W1 W 0.767857(13) 0.157412(13) 0.293541(8) 0.01908(5) Uani 1 1 d . . . Cl1 Cl 0.58747(9) 0.05412(9) 0.39781(5) 0.02470(16) Uani 1 1 d . . . Cl2 Cl 0.27955(12) 0.57822(14) 0.34836(8) 0.0550(3) Uani 1 1 d . . . Cl3 Cl 0.58727(11) 0.58160(12) 0.40420(7) 0.0435(2) Uani 1 1 d . . . S1 S 0.98404(9) 0.55679(9) 0.19831(5) 0.02450(17) Uani 1 1 d . . . O2 O 0.5371(3) 0.2985(3) 0.21034(19) 0.0405(7) Uani 1 1 d . . . O1 O 0.8766(3) 0.4723(3) 0.42880(17) 0.0348(6) Uani 1 1 d . . . N1 N 1.1488(3) 0.4659(3) 0.08286(18) 0.0266(6) Uani 1 1 d . . . N4 N 0.6935(3) -0.0770(3) 0.20606(17) 0.0239(6) Uani 1 1 d . . . N3 N 0.9373(3) 0.0592(3) 0.35162(17) 0.0213(5) Uani 1 1 d . . . C1 C 0.8941(4) 0.2615(4) 0.2253(2) 0.0243(7) Uani 1 1 d . . . C2 C 0.4348(4) 0.6582(4) 0.4277(3) 0.0328(8) Uani 1 1 d . . . H2A H 0.4019 0.6401 0.4850 0.039 Uiso 1 1 calc R . . H2B H 0.4695 0.7704 0.4322 0.039 Uiso 1 1 calc R . . C10 C 0.9833(4) 0.3661(4) 0.1798(2) 0.0243(7) Uani 1 1 d . . . C11 C 1.0773(4) 0.3424(4) 0.1157(2) 0.0277(7) Uani 1 1 d . . . H11 H 1.0920 0.2446 0.0952 0.033 Uiso 1 1 calc R . . C12 C 1.1113(4) 0.5875(4) 0.1208(2) 0.0230(7) Uani 1 1 d . . . C13 C 1.1744(4) 0.7393(4) 0.1013(2) 0.0228(7) Uani 1 1 d . . . C14 C 1.2363(4) 0.7533(4) 0.0225(2) 0.0266(7) Uani 1 1 d . . . H18 H 1.2359 0.6639 -0.0191 0.032 Uiso 1 1 calc R . . C15 C 1.2981(4) 0.8962(4) 0.0045(2) 0.0296(7) Uani 1 1 d . . . H17 H 1.3396 0.9046 -0.0494 0.035 Uiso 1 1 calc R . . C16 C 1.2995(4) 1.0268(4) 0.0650(2) 0.0321(8) Uani 1 1 d . . . H16 H 1.3423 1.1249 0.0526 0.039 Uiso 1 1 calc R . . C17 C 1.2387(4) 1.0151(4) 0.1437(2) 0.0334(8) Uani 1 1 d . . . H15 H 1.2401 1.1051 0.1852 0.040 Uiso 1 1 calc R . . C18 C 1.1760(4) 0.8724(4) 0.1620(2) 0.0278(7) Uani 1 1 d . . . H14 H 1.1339 0.8648 0.2158 0.033 Uiso 1 1 calc R . . C22 C 0.6146(4) 0.2408(4) 0.2416(2) 0.0268(7) Uani 1 1 d . . . C21 C 0.8351(4) 0.3550(4) 0.3810(2) 0.0240(7) Uani 1 1 d . . . C41 C 0.5622(4) -0.1831(4) 0.2085(3) 0.0334(8) Uani 1 1 d . . . H41 H 0.4914 -0.1558 0.2465 0.040 Uiso 1 1 calc R . . C42 C 0.5253(5) -0.3303(5) 0.1582(3) 0.0448(10) Uani 1 1 d . . . H42 H 0.4324 -0.4031 0.1627 0.054 Uiso 1 1 calc R . . C43 C 0.6268(5) -0.3696(5) 0.1009(3) 0.0431(10) Uani 1 1 d . . . H43 H 0.6045 -0.4698 0.0655 0.052 Uiso 1 1 calc R . . C44 C 0.7585(5) -0.2619(4) 0.0965(2) 0.0374(9) Uani 1 1 d . . . H44 H 0.8285 -0.2861 0.0570 0.045 Uiso 1 1 calc R . . C45 C 0.7909(4) -0.1170(4) 0.1496(2) 0.0307(8) Uani 1 1 d . . . H45 H 0.8841 -0.0435 0.1462 0.037 Uiso 1 1 calc R . . C31 C 0.8996(4) -0.0802(4) 0.3715(2) 0.0248(7) Uani 1 1 d . . . H31 H 0.7959 -0.1383 0.3634 0.030 Uiso 1 1 calc R . . C32 C 1.0058(4) -0.1423(4) 0.4033(2) 0.0279(7) Uani 1 1 d . . . H32 H 0.9752 -0.2412 0.4164 0.033 Uiso 1 1 calc R . . C33 C 1.1570(4) -0.0581(4) 0.4158(2) 0.0333(8) Uani 1 1 d . . . H33 H 1.2320 -0.0976 0.4381 0.040 Uiso 1 1 calc R . . C34 C 1.1968(4) 0.0844(4) 0.3952(2) 0.0318(8) Uani 1 1 d . . . H34 H 1.3001 0.1440 0.4025 0.038 Uiso 1 1 calc R . . C35 C 1.0851(4) 0.1394(4) 0.3641(2) 0.0263(7) Uani 1 1 d . . . H35 H 1.1136 0.2382 0.3508 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 W1 0.01894(8) 0.01895(8) 0.02060(8) 0.00480(5) 0.00262(5) 0.00697(5) Cl1 0.0217(4) 0.0267(4) 0.0274(4) 0.0064(3) 0.0078(3) 0.0085(3) Cl2 0.0364(6) 0.0604(7) 0.0634(7) 0.0181(6) -0.0090(5) 0.0041(5) Cl3 0.0380(5) 0.0435(5) 0.0592(6) 0.0172(5) 0.0137(5) 0.0228(4) S1 0.0283(4) 0.0232(4) 0.0243(4) 0.0067(3) 0.0086(3) 0.0092(3) O2 0.0427(16) 0.0307(14) 0.0484(17) 0.0036(12) -0.0145(13) 0.0170(12) O1 0.0333(14) 0.0290(14) 0.0379(15) -0.0017(11) -0.0052(11) 0.0095(11) N1 0.0292(15) 0.0234(14) 0.0279(15) 0.0054(12) 0.0094(12) 0.0081(12) N4 0.0279(15) 0.0272(15) 0.0182(13) 0.0027(11) -0.0016(11) 0.0123(12) N3 0.0191(13) 0.0227(14) 0.0216(14) 0.0026(11) 0.0033(10) 0.0065(11) C1 0.0259(17) 0.0252(17) 0.0227(16) 0.0033(13) -0.0005(13) 0.0107(14) C2 0.0334(19) 0.0295(19) 0.038(2) 0.0067(16) 0.0062(16) 0.0136(15) C10 0.0262(17) 0.0228(16) 0.0241(17) 0.0045(13) 0.0001(13) 0.0077(13) C11 0.0318(19) 0.0239(17) 0.0298(18) 0.0053(14) 0.0093(15) 0.0113(14) C12 0.0230(16) 0.0238(16) 0.0215(16) 0.0032(13) 0.0023(13) 0.0067(13) C13 0.0197(15) 0.0244(16) 0.0245(16) 0.0071(13) 0.0019(12) 0.0055(13) C14 0.0270(17) 0.0270(17) 0.0248(17) 0.0049(14) 0.0008(13) 0.0066(14) C15 0.0307(18) 0.0335(19) 0.0249(18) 0.0107(15) 0.0041(14) 0.0065(15) C16 0.0286(19) 0.0285(18) 0.038(2) 0.0136(16) 0.0036(15) 0.0017(15) C17 0.035(2) 0.0273(18) 0.036(2) 0.0045(15) 0.0088(16) 0.0072(15) C18 0.0284(18) 0.0272(18) 0.0275(18) 0.0054(14) 0.0077(14) 0.0071(14) C22 0.0276(18) 0.0200(16) 0.0305(18) 0.0007(14) -0.0022(14) 0.0072(14) C21 0.0209(16) 0.0268(18) 0.0258(17) 0.0076(14) 0.0028(13) 0.0078(13) C41 0.0242(18) 0.0313(19) 0.041(2) -0.0027(16) -0.0021(15) 0.0100(15) C42 0.030(2) 0.033(2) 0.062(3) -0.0093(19) -0.0081(19) 0.0104(17) C43 0.052(3) 0.033(2) 0.042(2) -0.0116(18) -0.0183(19) 0.0262(19) C44 0.056(3) 0.040(2) 0.0230(18) 0.0013(16) 0.0025(17) 0.029(2) C45 0.039(2) 0.0299(19) 0.0265(18) 0.0064(15) 0.0060(15) 0.0147(16) C31 0.0282(18) 0.0237(16) 0.0230(17) 0.0041(13) 0.0046(13) 0.0083(14) C32 0.045(2) 0.0242(17) 0.0201(16) 0.0025(13) 0.0021(14) 0.0200(15) C33 0.039(2) 0.045(2) 0.0243(18) 0.0013(15) 0.0001(15) 0.0298(18) C34 0.0238(17) 0.041(2) 0.0292(19) 0.0000(16) -0.0006(14) 0.0138(15) C35 0.0241(17) 0.0268(17) 0.0264(17) 0.0025(14) 0.0043(13) 0.0063(14) _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 W1 C1 1.822(3) . ? W1 C21 1.993(3) . ? W1 C22 2.001(3) . ? W1 N4 2.246(3) . ? W1 N3 2.254(3) . ? W1 Cl1 2.5107(8) . ? Cl2 C2 1.753(4) . ? Cl3 C2 1.756(4) . ? S1 C12 1.729(3) . ? S1 C10 1.735(3) . ? O2 C22 1.149(4) . ? O1 C21 1.152(4) . ? N1 C12 1.308(4) . ? N1 C11 1.364(4) . ? N4 C41 1.342(5) . ? N4 C45 1.355(4) . ? N3 C35 1.346(4) . ? N3 C31 1.348(4) . ? C1 C10 1.418(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C10 C11 1.374(5) . ? C11 H11 0.9500 . ? C12 C13 1.468(4) . ? C13 C14 1.395(5) . ? C13 C18 1.401(5) . ? C14 C15 1.383(5) . ? C14 H18 0.9500 . ? C15 C16 1.383(5) . ? C15 H17 0.9500 . ? C16 C17 1.386(5) . ? C16 H16 0.9500 . ? C17 C18 1.385(5) . ? C17 H15 0.9500 . ? C18 H14 0.9500 . ? C41 C42 1.383(5) . ? C41 H41 0.9500 . ? C42 C43 1.389(6) . ? C42 H42 0.9500 . ? C43 C44 1.360(6) . ? C43 H43 0.9500 . ? C44 C45 1.385(5) . ? C44 H44 0.9500 . ? C45 H45 0.9500 . ? C31 C32 1.384(5) . ? C31 H31 0.9500 . ? C32 C33 1.383(5) . ? C32 H32 0.9500 . ? C33 C34 1.379(5) . ? C33 H33 0.9500 . ? C34 C35 1.379(5) . ? C34 H34 0.9500 . ? C35 H35 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 C1 W1 C21 84.15(14) . . ? C1 W1 C22 83.52(14) . . ? C21 W1 C22 87.53(13) . . ? C1 W1 N4 100.22(12) . . ? C21 W1 N4 174.25(11) . . ? C22 W1 N4 96.64(11) . . ? C1 W1 N3 97.20(12) . . ? C21 W1 N3 93.31(11) . . ? C22 W1 N3 178.95(11) . . ? N4 W1 N3 82.49(9) . . ? C1 W1 Cl1 170.93(10) . . ? C21 W1 Cl1 88.09(10) . . ? C22 W1 Cl1 91.47(10) . . ? N4 W1 Cl1 87.84(7) . . ? N3 W1 Cl1 87.92(7) . . ? C12 S1 C10 89.82(16) . . ? C12 N1 C11 110.5(3) . . ? C41 N4 C45 117.5(3) . . ? C41 N4 W1 124.6(2) . . ? C45 N4 W1 117.8(2) . . ? C35 N3 C31 117.4(3) . . ? C35 N3 W1 119.2(2) . . ? C31 N3 W1 123.3(2) . . ? C10 C1 W1 169.4(3) . . ? Cl2 C2 Cl3 112.7(2) . . ? Cl2 C2 H2A 109.1 . . ? Cl3 C2 H2A 109.1 . . ? Cl2 C2 H2B 109.1 . . ? Cl3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C11 C10 C1 129.9(3) . . ? C11 C10 S1 108.0(3) . . ? C1 C10 S1 122.0(3) . . ? N1 C11 C10 117.0(3) . . ? N1 C11 H11 121.5 . . ? C10 C11 H11 121.5 . . ? N1 C12 C13 123.1(3) . . ? N1 C12 S1 114.6(2) . . ? C13 C12 S1 122.2(2) . . ? C14 C13 C18 118.9(3) . . ? C14 C13 C12 120.4(3) . . ? C18 C13 C12 120.7(3) . . ? C15 C14 C13 120.6(3) . . ? C15 C14 H18 119.7 . . ? C13 C14 H18 119.7 . . ? C14 C15 C16 120.0(3) . . ? C14 C15 H17 120.0 . . ? C16 C15 H17 120.0 . . ? C15 C16 C17 120.2(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C18 C17 C16 120.1(3) . . ? C18 C17 H15 120.0 . . ? C16 C17 H15 120.0 . . ? C17 C18 C13 120.2(3) . . ? C17 C18 H14 119.9 . . ? C13 C18 H14 119.9 . . ? O2 C22 W1 174.1(3) . . ? O1 C21 W1 177.0(3) . . ? N4 C41 C42 123.0(4) . . ? N4 C41 H41 118.5 . . ? C42 C41 H41 118.5 . . ? C41 C42 C43 118.7(4) . . ? C41 C42 H42 120.6 . . ? C43 C42 H42 120.6 . . ? C44 C43 C42 118.7(4) . . ? C44 C43 H43 120.6 . . ? C42 C43 H43 120.6 . . ? C43 C44 C45 120.1(4) . . ? C43 C44 H44 119.9 . . ? C45 C44 H44 119.9 . . ? N4 C45 C44 121.9(4) . . ? N4 C45 H45 119.1 . . ? C44 C45 H45 119.1 . . ? N3 C31 C32 122.8(3) . . ? N3 C31 H31 118.6 . . ? C32 C31 H31 118.6 . . ? C33 C32 C31 119.0(3) . . ? C33 C32 H32 120.5 . . ? C31 C32 H32 120.5 . . ? C34 C33 C32 118.7(3) . . ? C34 C33 H33 120.6 . . ? C32 C33 H33 120.6 . . ? C35 C34 C33 119.3(3) . . ? C35 C34 H34 120.4 . . ? C33 C34 H34 120.4 . . ? N3 C35 C34 122.9(3) . . ? N3 C35 H35 118.6 . . ? C34 C35 H35 118.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 W1 N4 C41 -154.3(3) . . . . ? C22 W1 N4 C41 -69.7(3) . . . . ? N3 W1 N4 C41 109.7(3) . . . . ? Cl1 W1 N4 C41 21.5(3) . . . . ? C1 W1 N4 C45 29.0(3) . . . . ? C22 W1 N4 C45 113.5(3) . . . . ? N3 W1 N4 C45 -67.1(2) . . . . ? Cl1 W1 N4 C45 -155.2(2) . . . . ? C1 W1 N3 C35 31.5(3) . . . . ? C21 W1 N3 C35 -53.0(3) . . . . ? N4 W1 N3 C35 130.9(2) . . . . ? Cl1 W1 N3 C35 -141.0(2) . . . . ? C1 W1 N3 C31 -145.6(3) . . . . ? C21 W1 N3 C31 129.9(3) . . . . ? N4 W1 N3 C31 -46.1(3) . . . . ? Cl1 W1 N3 C31 42.0(2) . . . . ? C21 W1 C1 C10 -35.4(14) . . . . ? C22 W1 C1 C10 52.8(14) . . . . ? N4 W1 C1 C10 148.4(14) . . . . ? N3 W1 C1 C10 -128.0(14) . . . . ? W1 C1 C10 C11 -177.6(12) . . . . ? W1 C1 C10 S1 0.9(16) . . . . ? C12 S1 C10 C11 -0.9(3) . . . . ? C12 S1 C10 C1 -179.7(3) . . . . ? C12 N1 C11 C10 -0.1(4) . . . . ? C1 C10 C11 N1 179.4(3) . . . . ? S1 C10 C11 N1 0.8(4) . . . . ? C11 N1 C12 C13 177.7(3) . . . . ? C11 N1 C12 S1 -0.7(4) . . . . ? C10 S1 C12 N1 1.0(3) . . . . ? C10 S1 C12 C13 -177.5(3) . . . . ? N1 C12 C13 C14 21.9(5) . . . . ? S1 C12 C13 C14 -159.7(3) . . . . ? N1 C12 C13 C18 -156.9(3) . . . . ? S1 C12 C13 C18 21.4(4) . . . . ? C18 C13 C14 C15 -0.1(5) . . . . ? C12 C13 C14 C15 -178.9(3) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? C14 C15 C16 C17 -0.2(5) . . . . ? C15 C16 C17 C18 -0.1(6) . . . . ? C16 C17 C18 C13 0.4(5) . . . . ? C14 C13 C18 C17 -0.3(5) . . . . ? C12 C13 C18 C17 178.6(3) . . . . ? C45 N4 C41 C42 1.9(5) . . . . ? W1 N4 C41 C42 -174.9(3) . . . . ? N4 C41 C42 C43 -1.6(6) . . . . ? C41 C42 C43 C44 0.1(6) . . . . ? C42 C43 C44 C45 1.1(6) . . . . ? C41 N4 C45 C44 -0.6(5) . . . . ? W1 N4 C45 C44 176.4(3) . . . . ? C43 C44 C45 N4 -0.8(6) . . . . ? C35 N3 C31 C32 -0.2(5) . . . . ? W1 N3 C31 C32 176.9(2) . . . . ? N3 C31 C32 C33 0.3(5) . . . . ? C31 C32 C33 C34 -0.6(5) . . . . ? C32 C33 C34 C35 0.8(5) . . . . ? C31 N3 C35 C34 0.4(5) . . . . ? W1 N3 C35 C34 -176.8(3) . . . . ? C33 C34 C35 N3 -0.8(5) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.616 _refine_diff_density_min -0.541 _refine_diff_density_rms 0.115 # Attachment '- Supinf.CIF' data_Compound-7 _database_code_depnum_ccdc_archive 'CCDC 744828' _audit_creation_method SHELXL-97 _chemical_name_systematic ;cis-dicarbonyl-2\k^2^C-dichloro-1\k,2\k-{\m-[2-(1- piperidinyl)thiazol-5-yl]methylidyne-1\kC^1^:2\kC^1^} bis(pyridine-2\kN)goldtungsten(Au---W) hemi-tetrahydrofuran solvate ; _chemical_name_common ; cis-dicarbonyl-2kappa$2!C-dichloro-1kappa,2kappa-(mu-(2-(1- piperidinyl)thiazol-5-yl)methylidyne-1kappaC$1!:2kappaC$1!) bis(pyridine-2kappaN)goldtungsten(Au---W) hemi-tetrahydrofuran solvate ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H21 Au Cl2 N4 O2 S W, 0.5(C4 H8 O)' _chemical_formula_sum 'C23 H25 Au Cl2 N4 O2.50 S W' _chemical_formula_weight 881.25 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' S S 0.1246 0.1234 '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' W W -0.8490 6.8722 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6030(14) _cell_length_b 11.8806(16) _cell_length_c 11.9320(16) _cell_angle_alpha 70.039(2) _cell_angle_beta 83.042(2) _cell_angle_gamma 69.143(2) _cell_volume 1320.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3219 _cell_measurement_theta_min 2.188 _cell_measurement_theta_max 25.623 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.126 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 788 _exptl_absorpt_coefficient_mu 10.208 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.489 _exptl_absorpt_correction_T_max 0.666 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14111 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 26.48 _reflns_number_total 5400 _reflns_number_gt 4425 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)' _computing_publication_material X-Seed _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. Electron density belonging to a heavily disordered thf molecule was removed using the Squeeze routine in the Platon set of programmes (Spek, 2003). ; _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^)+(0.0528P)^2^+1.0394P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5400 _refine_ls_number_parameters 289 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0623 _refine_ls_wR_factor_ref 0.1259 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.218 _refine_ls_restrained_S_all 1.218 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.33162(4) 0.16408(4) 0.41229(4) 0.02314(14) Uani 1 1 d . . . W1 W 0.30091(4) 0.28215(4) 0.16699(4) 0.02032(14) Uani 1 1 d . . . Cl1 Cl 0.2260(3) 0.3428(3) -0.0383(3) 0.0292(7) Uani 1 1 d . . . Cl2 Cl 0.2766(3) 0.0221(3) 0.5768(3) 0.0384(8) Uani 1 1 d . . . S1 S 0.5439(3) 0.2937(3) 0.4646(3) 0.0277(7) Uani 1 1 d . . . O1 O 0.1702(9) 0.5700(8) 0.1474(8) 0.039(2) Uani 1 1 d . . . O2 O 0.5606(9) 0.3294(8) 0.0368(8) 0.039(2) Uani 1 1 d . . . N1 N 0.5904(10) 0.4893(9) 0.3139(10) 0.033(3) Uani 1 1 d . . . N2 N 0.6897(11) 0.4230(9) 0.5010(10) 0.035(3) Uani 1 1 d . . . N3 N 0.3832(9) 0.0780(9) 0.1661(8) 0.024(2) Uani 1 1 d . . . N4 N 0.1038(8) 0.2464(8) 0.2127(7) 0.0162(18) Uani 1 1 d U . . C1 C 0.3942(12) 0.2965(10) 0.2839(10) 0.025(3) Uani 1 1 d . . . C10 C 0.4745(11) 0.3532(10) 0.3218(10) 0.023(3) Uani 1 1 d . . . C11 C 0.5138(12) 0.4551(11) 0.2564(11) 0.026(3) Uani 1 1 d . . . H11 H 0.4888 0.4995 0.1751 0.031 Uiso 1 1 calc R . . C12 C 0.6159(12) 0.4138(11) 0.4244(12) 0.029(3) Uani 1 1 d . . . C13 C 0.7814(13) 0.4979(13) 0.4563(13) 0.042(3) Uani 1 1 d . . . H13A H 0.7789 0.5464 0.5100 0.051 Uiso 1 1 calc R . . H13B H 0.7529 0.5590 0.3757 0.051 Uiso 1 1 calc R . . C14 C 0.9239(15) 0.4060(16) 0.4516(14) 0.057(5) Uani 1 1 d . . . H14A H 0.9279 0.3639 0.3919 0.069 Uiso 1 1 calc R . . H14B H 0.9882 0.4534 0.4272 0.069 Uiso 1 1 calc R . . C15 C 0.9631(17) 0.3063(18) 0.5736(17) 0.072(5) Uani 1 1 d . . . H15A H 1.0545 0.2455 0.5692 0.086 Uiso 1 1 calc R . . H15B H 0.9661 0.3484 0.6315 0.086 Uiso 1 1 calc R . . C16 C 0.8660(17) 0.2353(15) 0.6169(15) 0.063(5) Uani 1 1 d . . . H16A H 0.8907 0.1759 0.6987 0.076 Uiso 1 1 calc R . . H16B H 0.8703 0.1848 0.5646 0.076 Uiso 1 1 calc R . . C17 C 0.7232(13) 0.3286(13) 0.6164(12) 0.040(3) Uani 1 1 d . . . H17A H 0.6583 0.2818 0.6379 0.048 Uiso 1 1 calc R . . H17B H 0.7161 0.3707 0.6767 0.048 Uiso 1 1 calc R . . C21 C 0.2153(11) 0.4633(10) 0.1539(10) 0.022(2) Uani 1 1 d . . . C22 C 0.4659(12) 0.3097(11) 0.0845(10) 0.026(3) Uani 1 1 d . . . C31 C 0.4996(11) 0.0001(10) 0.2217(10) 0.025(3) Uani 1 1 d . . . H31 H 0.5448 0.0310 0.2624 0.030 Uiso 1 1 calc R . . C32 C 0.5562(13) -0.1245(11) 0.2217(11) 0.033(3) Uani 1 1 d . . . H32 H 0.6393 -0.1778 0.2617 0.039 Uiso 1 1 calc R . . C33 C 0.4929(14) -0.1698(12) 0.1648(13) 0.041(4) Uani 1 1 d . . . H33 H 0.5295 -0.2559 0.1664 0.049 Uiso 1 1 calc R . . C34 C 0.3747(14) -0.0901(12) 0.1044(12) 0.040(3) Uani 1 1 d . . . H34 H 0.3299 -0.1194 0.0619 0.048 Uiso 1 1 calc R . . C35 C 0.3218(12) 0.0351(11) 0.1069(10) 0.029(3) Uani 1 1 d . . . H35 H 0.2403 0.0907 0.0654 0.035 Uiso 1 1 calc R . . C41 C -0.0143(11) 0.3415(12) 0.1609(10) 0.028(3) Uani 1 1 d . . . H41 H -0.0086 0.4196 0.1070 0.033 Uiso 1 1 calc R . . C42 C -0.1372(12) 0.3279(12) 0.1837(11) 0.033(3) Uani 1 1 d . . . H42 H -0.2154 0.3952 0.1459 0.040 Uiso 1 1 calc R . . C43 C -0.1480(13) 0.2155(12) 0.2623(13) 0.039(3) Uani 1 1 d . . . H43 H -0.2337 0.2049 0.2790 0.047 Uiso 1 1 calc R . . C44 C -0.0341(12) 0.1192(12) 0.3161(12) 0.035(3) Uani 1 1 d . . . H44 H -0.0408 0.0420 0.3714 0.042 Uiso 1 1 calc R . . C45 C 0.0904(12) 0.1351(11) 0.2894(10) 0.027(3) Uani 1 1 d . . . H45 H 0.1689 0.0668 0.3253 0.032 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.0223(3) 0.0232(3) 0.0240(3) -0.00701(19) 0.00271(19) -0.0093(2) W1 0.0187(3) 0.0150(2) 0.0234(3) -0.00716(19) 0.00425(19) -0.00155(19) Cl1 0.0284(16) 0.0272(15) 0.0225(14) -0.0060(12) 0.0023(12) -0.0008(12) Cl2 0.0367(18) 0.0437(19) 0.0324(17) -0.0002(14) -0.0023(14) -0.0215(16) S1 0.0289(17) 0.0227(15) 0.0330(17) -0.0095(13) 0.0016(13) -0.0104(13) O1 0.034(5) 0.026(5) 0.048(6) -0.013(4) 0.000(4) 0.001(4) O2 0.039(5) 0.035(5) 0.040(5) -0.015(4) 0.013(4) -0.013(4) N1 0.027(6) 0.023(5) 0.045(7) -0.010(5) 0.010(5) -0.010(5) N2 0.031(6) 0.025(6) 0.052(7) -0.014(5) 0.002(5) -0.012(5) N3 0.024(5) 0.031(5) 0.018(5) -0.007(4) 0.001(4) -0.011(4) N4 0.016(2) 0.016(2) 0.015(2) -0.0065(11) 0.0012(10) -0.0037(11) C1 0.027(6) 0.010(5) 0.032(7) -0.005(5) 0.015(5) -0.007(5) C10 0.016(6) 0.011(5) 0.033(7) -0.007(5) 0.000(5) 0.005(4) C11 0.026(6) 0.024(6) 0.034(7) -0.018(5) 0.003(5) -0.009(5) C12 0.024(6) 0.029(7) 0.041(8) -0.020(6) 0.011(6) -0.014(5) C13 0.035(8) 0.053(9) 0.051(9) -0.031(7) 0.000(7) -0.015(7) C14 0.041(9) 0.085(12) 0.067(11) -0.063(10) 0.020(8) -0.016(9) C15 0.044(10) 0.086(14) 0.087(15) -0.041(12) -0.009(10) -0.008(10) C16 0.062(11) 0.052(10) 0.060(11) -0.026(9) -0.015(9) 0.009(9) C17 0.040(8) 0.042(8) 0.040(8) -0.022(7) 0.002(6) -0.010(7) C21 0.019(6) 0.011(5) 0.031(6) -0.010(5) -0.001(5) 0.004(4) C22 0.031(7) 0.024(6) 0.029(7) -0.016(5) 0.006(5) -0.011(5) C31 0.024(6) 0.024(6) 0.027(6) -0.007(5) -0.001(5) -0.007(5) C32 0.025(7) 0.022(6) 0.039(7) -0.007(6) 0.009(6) 0.000(5) C33 0.041(8) 0.029(7) 0.055(9) -0.023(7) 0.024(7) -0.014(7) C34 0.046(9) 0.037(8) 0.047(8) -0.028(7) 0.013(7) -0.017(7) C35 0.027(7) 0.034(7) 0.024(6) -0.016(5) 0.011(5) -0.006(6) C41 0.016(6) 0.036(7) 0.020(6) -0.007(5) 0.003(5) 0.000(5) C42 0.022(7) 0.035(7) 0.034(7) -0.011(6) 0.000(5) 0.000(6) C43 0.021(7) 0.039(8) 0.055(9) -0.015(7) 0.004(6) -0.009(6) C44 0.031(7) 0.026(7) 0.041(8) 0.000(6) -0.011(6) -0.010(6) C45 0.020(6) 0.024(6) 0.032(7) -0.006(5) 0.004(5) -0.007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Au1 C1 2.028(10) . ? Au1 Cl2 2.281(3) . ? Au1 W1 2.7826(7) . ? Au1 S1 3.361(3) . ? W1 C1 1.890(13) . ? W1 C21 1.973(10) . ? W1 C22 1.976(12) . ? W1 N4 2.246(9) . ? W1 N3 2.269(9) . ? W1 Cl1 2.451(3) . ? S1 C10 1.748(12) . ? S1 C12 1.752(12) . ? O1 C21 1.163(12) . ? O2 C22 1.152(14) . ? N1 C12 1.313(16) . ? N1 C11 1.363(15) . ? N2 C12 1.328(16) . ? N2 C17 1.436(16) . ? N2 C13 1.479(16) . ? N3 C35 1.333(15) . ? N3 C31 1.337(14) . ? N4 C45 1.373(13) . ? N4 C41 1.389(13) . ? C1 C10 1.446(16) . ? C10 C11 1.372(15) . ? C11 H11 0.9500 . ? C13 C14 1.524(18) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.52(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.49(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.525(19) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C31 C32 1.385(16) . ? C31 H31 0.9500 . ? C32 C33 1.349(18) . ? C32 H32 0.9500 . ? C33 C34 1.376(19) . ? C33 H33 0.9500 . ? C34 C35 1.399(16) . ? C34 H34 0.9500 . ? C35 H35 0.9500 . ? C41 C42 1.353(16) . ? C41 H41 0.9500 . ? C42 C43 1.379(17) . ? C42 H42 0.9500 . ? C43 C44 1.372(17) . ? C43 H43 0.9500 . ? C44 C45 1.384(16) . ? C44 H44 0.9500 . ? C45 H45 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 C1 Au1 Cl2 171.2(4) . . ? C1 Au1 W1 42.8(4) . . ? Cl2 Au1 W1 146.01(9) . . ? C1 Au1 S1 56.6(4) . . ? Cl2 Au1 S1 114.64(10) . . ? W1 Au1 S1 99.33(5) . . ? C1 W1 C21 77.7(5) . . ? C1 W1 C22 75.9(5) . . ? C21 W1 C22 92.4(5) . . ? C1 W1 N4 119.9(4) . . ? C21 W1 N4 92.1(4) . . ? C22 W1 N4 164.2(4) . . ? C1 W1 N3 108.7(4) . . ? C21 W1 N3 173.6(4) . . ? C22 W1 N3 89.5(4) . . ? N4 W1 N3 84.6(3) . . ? C1 W1 Cl1 152.3(3) . . ? C21 W1 Cl1 86.9(3) . . ? C22 W1 Cl1 82.0(4) . . ? N4 W1 Cl1 83.1(2) . . ? N3 W1 Cl1 87.3(2) . . ? C1 W1 Au1 46.8(3) . . ? C21 W1 Au1 102.3(3) . . ? C22 W1 Au1 113.9(3) . . ? N4 W1 Au1 79.8(2) . . ? N3 W1 Au1 82.5(2) . . ? Cl1 W1 Au1 160.85(8) . . ? C10 S1 C12 89.6(6) . . ? C10 S1 Au1 62.3(4) . . ? C12 S1 Au1 151.2(5) . . ? C12 N1 C11 111.8(10) . . ? C12 N2 C17 121.1(11) . . ? C12 N2 C13 119.7(11) . . ? C17 N2 C13 115.1(11) . . ? C35 N3 C31 118.8(10) . . ? C35 N3 W1 121.8(8) . . ? C31 N3 W1 119.3(8) . . ? C45 N4 C41 116.3(9) . . ? C45 N4 W1 124.4(7) . . ? C41 N4 W1 119.2(7) . . ? C10 C1 W1 152.4(8) . . ? C10 C1 Au1 117.1(8) . . ? W1 C1 Au1 90.4(5) . . ? C11 C10 C1 128.4(11) . . ? C11 C10 S1 108.4(9) . . ? C1 C10 S1 123.1(8) . . ? N1 C11 C10 116.7(11) . . ? N1 C11 H11 121.7 . . ? C10 C11 H11 121.7 . . ? N1 C12 N2 125.2(11) . . ? N1 C12 S1 113.5(9) . . ? N2 C12 S1 121.3(10) . . ? N2 C13 C14 108.2(12) . . ? N2 C13 H13A 110.1 . . ? C14 C13 H13A 110.1 . . ? N2 C13 H13B 110.1 . . ? C14 C13 H13B 110.1 . . ? H13A C13 H13B 108.4 . . ? C15 C14 C13 109.8(13) . . ? C15 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? C15 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C16 C15 C14 111.9(14) . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 C17 109.8(13) . . ? C15 C16 H16A 109.7 . . ? C17 C16 H16A 109.7 . . ? C15 C16 H16B 109.7 . . ? C17 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? N2 C17 C16 110.7(12) . . ? N2 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? N2 C17 H17B 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? O1 C21 W1 177.0(10) . . ? O2 C22 W1 177.9(10) . . ? N3 C31 C32 121.8(12) . . ? N3 C31 H31 119.1 . . ? C32 C31 H31 119.1 . . ? C33 C32 C31 119.7(12) . . ? C33 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? C32 C33 C34 119.3(12) . . ? C32 C33 H33 120.3 . . ? C34 C33 H33 120.3 . . ? C33 C34 C35 118.7(13) . . ? C33 C34 H34 120.6 . . ? C35 C34 H34 120.6 . . ? N3 C35 C34 121.6(12) . . ? N3 C35 H35 119.2 . . ? C34 C35 H35 119.2 . . ? C42 C41 N4 123.0(11) . . ? C42 C41 H41 118.5 . . ? N4 C41 H41 118.5 . . ? C41 C42 C43 119.5(12) . . ? C41 C42 H42 120.3 . . ? C43 C42 H42 120.3 . . ? C44 C43 C42 119.6(12) . . ? C44 C43 H43 120.2 . . ? C42 C43 H43 120.2 . . ? C43 C44 C45 119.6(12) . . ? C43 C44 H44 120.2 . . ? C45 C44 H44 120.2 . . ? N4 C45 C44 121.9(11) . . ? N4 C45 H45 119.0 . . ? C44 C45 H45 119.0 . . ? 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 Cl2 Au1 W1 C1 178.5(5) . . . . ? S1 Au1 W1 C1 -3.4(4) . . . . ? C1 Au1 W1 C21 -59.6(5) . . . . ? Cl2 Au1 W1 C21 118.8(4) . . . . ? S1 Au1 W1 C21 -63.1(3) . . . . ? C1 Au1 W1 C22 38.6(6) . . . . ? Cl2 Au1 W1 C22 -142.9(4) . . . . ? S1 Au1 W1 C22 35.1(4) . . . . ? C1 Au1 W1 N4 -149.6(5) . . . . ? Cl2 Au1 W1 N4 28.9(3) . . . . ? S1 Au1 W1 N4 -153.0(2) . . . . ? C1 Au1 W1 N3 124.6(5) . . . . ? Cl2 Au1 W1 N3 -56.9(3) . . . . ? S1 Au1 W1 N3 121.2(2) . . . . ? C1 Au1 W1 Cl1 -177.2(5) . . . . ? Cl2 Au1 W1 Cl1 1.3(3) . . . . ? S1 Au1 W1 Cl1 179.4(2) . . . . ? C1 Au1 S1 C10 5.1(5) . . . . ? Cl2 Au1 S1 C10 -173.3(4) . . . . ? W1 Au1 S1 C10 7.9(4) . . . . ? C1 Au1 S1 C12 18.7(9) . . . . ? Cl2 Au1 S1 C12 -159.7(8) . . . . ? W1 Au1 S1 C12 21.5(8) . . . . ? C1 W1 N3 C35 168.7(8) . . . . ? C21 W1 N3 C35 -10(4) . . . . ? C22 W1 N3 C35 -116.4(9) . . . . ? N4 W1 N3 C35 49.0(8) . . . . ? Cl1 W1 N3 C35 -34.4(8) . . . . ? Au1 W1 N3 C35 129.4(8) . . . . ? C1 W1 N3 C31 -14.5(9) . . . . ? C21 W1 N3 C31 167(3) . . . . ? C22 W1 N3 C31 60.4(9) . . . . ? N4 W1 N3 C31 -134.2(8) . . . . ? Cl1 W1 N3 C31 142.4(8) . . . . ? Au1 W1 N3 C31 -53.8(8) . . . . ? C1 W1 N4 C45 -68.6(9) . . . . ? C21 W1 N4 C45 -145.6(9) . . . . ? C22 W1 N4 C45 108.0(16) . . . . ? N3 W1 N4 C45 39.8(9) . . . . ? Cl1 W1 N4 C45 127.8(9) . . . . ? Au1 W1 N4 C45 -43.4(8) . . . . ? C1 W1 N4 C41 111.6(8) . . . . ? C21 W1 N4 C41 34.7(8) . . . . ? C22 W1 N4 C41 -71.7(17) . . . . ? N3 W1 N4 C41 -139.9(8) . . . . ? Cl1 W1 N4 C41 -52.0(8) . . . . ? Au1 W1 N4 C41 136.8(8) . . . . ? C21 W1 C1 C10 -55.6(17) . . . . ? C22 W1 C1 C10 40.1(17) . . . . ? N4 W1 C1 C10 -140.9(16) . . . . ? N3 W1 C1 C10 124.6(17) . . . . ? Cl1 W1 C1 C10 2(2) . . . . ? Au1 W1 C1 C10 -176(2) . . . . ? C21 W1 C1 Au1 120.4(5) . . . . ? C22 W1 C1 Au1 -144.0(5) . . . . ? N4 W1 C1 Au1 35.1(5) . . . . ? N3 W1 C1 Au1 -59.5(4) . . . . ? Cl1 W1 C1 Au1 178.0(3) . . . . ? Cl2 Au1 C1 C10 3(3) . . . . ? W1 Au1 C1 C10 177.9(10) . . . . ? S1 Au1 C1 C10 -6.2(6) . . . . ? Cl2 Au1 C1 W1 -174.5(17) . . . . ? S1 Au1 C1 W1 175.9(5) . . . . ? W1 C1 C10 C11 5(3) . . . . ? Au1 C1 C10 C11 -170.6(9) . . . . ? W1 C1 C10 S1 -172.7(12) . . . . ? Au1 C1 C10 S1 11.9(12) . . . . ? C12 S1 C10 C11 1.4(8) . . . . ? Au1 S1 C10 C11 174.9(9) . . . . ? C12 S1 C10 C1 179.3(9) . . . . ? Au1 S1 C10 C1 -7.2(7) . . . . ? C12 N1 C11 C10 1.5(15) . . . . ? C1 C10 C11 N1 -179.7(10) . . . . ? S1 C10 C11 N1 -2.0(12) . . . . ? C11 N1 C12 N2 178.9(11) . . . . ? C11 N1 C12 S1 -0.3(13) . . . . ? C17 N2 C12 N1 -173.8(11) . . . . ? C13 N2 C12 N1 -17.5(18) . . . . ? C17 N2 C12 S1 5.4(16) . . . . ? C13 N2 C12 S1 161.6(9) . . . . ? C10 S1 C12 N1 -0.7(9) . . . . ? Au1 S1 C12 N1 -12.7(15) . . . . ? C10 S1 C12 N2 -179.9(10) . . . . ? Au1 S1 C12 N2 168.1(6) . . . . ? C12 N2 C13 C14 -99.4(14) . . . . ? C17 N2 C13 C14 58.2(14) . . . . ? N2 C13 C14 C15 -55.5(16) . . . . ? C13 C14 C15 C16 57.1(18) . . . . ? C14 C15 C16 C17 -55.2(18) . . . . ? C12 N2 C17 C16 99.7(15) . . . . ? C13 N2 C17 C16 -57.6(15) . . . . ? C15 C16 C17 N2 54.0(17) . . . . ? C1 W1 C21 O1 33(20) . . . . ? C22 W1 C21 O1 -42(20) . . . . ? N4 W1 C21 O1 153(20) . . . . ? N3 W1 C21 O1 -148(18) . . . . ? Cl1 W1 C21 O1 -124(20) . . . . ? Au1 W1 C21 O1 73(20) . . . . ? C1 W1 C22 O2 -64(29) . . . . ? C21 W1 C22 O2 12(29) . . . . ? N4 W1 C22 O2 119(29) . . . . ? N3 W1 C22 O2 -174(29) . . . . ? Cl1 W1 C22 O2 99(29) . . . . ? Au1 W1 C22 O2 -92(29) . . . . ? C35 N3 C31 C32 -1.6(16) . . . . ? W1 N3 C31 C32 -178.4(8) . . . . ? N3 C31 C32 C33 -0.3(18) . . . . ? C31 C32 C33 C34 1.9(19) . . . . ? C32 C33 C34 C35 -1.8(19) . . . . ? C31 N3 C35 C34 1.7(16) . . . . ? W1 N3 C35 C34 178.5(9) . . . . ? C33 C34 C35 N3 0.0(18) . . . . ? C45 N4 C41 C42 0.4(17) . . . . ? W1 N4 C41 C42 -179.9(9) . . . . ? N4 C41 C42 C43 0.4(19) . . . . ? C41 C42 C43 C44 0(2) . . . . ? C42 C43 C44 C45 -1(2) . . . . ? C41 N4 C45 C44 -1.5(17) . . . . ? W1 N4 C45 C44 178.8(9) . . . . ? C43 C44 C45 N4 2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 2.242 _refine_diff_density_min -2.976 _refine_diff_density_rms 0.278 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 0.000 0.000 0.000 149 37 C~4~H~8~O _platon_squeeze_details 'Spek, 2003' #===END data_Compound-8 _database_code_depnum_ccdc_archive 'CCDC 744829' _audit_creation_method SHELXL-97 _chemical_name_systematic ;cis-dicarbonylchloro[(4-methylphenyl)methylidyne]- cis-bis(pyridine)tungsten ; _chemical_name_common ;cis-dicarbonylchloro((4-methylphenyl)methylidyne)-cis- bis(pyridine)tungsten ; _chemical_melting_point ? _chemical_formula_moiety 'C20 H17 Cl N2 O2 W' _chemical_formula_sum 'C20 H17 Cl N2 O2 W' _chemical_formula_weight 536.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_int_tables_number 15 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 26.655(4) _cell_length_b 7.1269(11) _cell_length_c 23.559(4) _cell_angle_alpha 90.00 _cell_angle_beta 121.419(2) _cell_angle_gamma 90.00 _cell_volume 3819.2(10) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3364 _cell_measurement_theta_min 2.995 _cell_measurement_theta_max 26.349 _exptl_crystal_description needle _exptl_crystal_colour orange _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.867 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 6.205 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.514 _exptl_absorpt_correction_T_max 0.789 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10600 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 26.40 _reflns_number_total 3889 _reflns_number_gt 3340 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-Seed (Barbour, 2001; Atwood & Barbour, 2003)' _computing_publication_material X-Seed _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^)+(0.0914P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3889 _refine_ls_number_parameters 236 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1349 _refine_ls_wR_factor_gt 0.1295 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 W1 W 0.656446(12) 0.91137(4) 0.799840(14) 0.01191(14) Uani 1 1 d . . . Cl1 Cl 0.67487(8) 0.6815(3) 0.89022(10) 0.0190(4) Uani 1 1 d . . . O1 O 0.7342(3) 0.6687(9) 0.7631(3) 0.0265(14) Uani 1 1 d . . . N1 N 0.7303(3) 1.0913(8) 0.8785(3) 0.0142(14) Uani 1 1 d . . . C1 C 0.6380(3) 1.0461(11) 0.7265(4) 0.0169(17) Uani 1 1 d . . . O2 O 0.5522(3) 0.6548(8) 0.6989(3) 0.0240(13) Uani 1 1 d . . . N2 N 0.5997(3) 1.0672(8) 0.8295(3) 0.0137(13) Uani 1 1 d . . . C2 C 0.6192(3) 1.1323(12) 0.6624(4) 0.0150(16) Uani 1 1 d . . . C3 C 0.5890(3) 1.0275(12) 0.6031(4) 0.0185(17) Uani 1 1 d . . . H3 H 0.5809 0.8983 0.6043 0.022 Uiso 1 1 calc R . . C4 C 0.5711(4) 1.1154(11) 0.5427(4) 0.0206(18) Uani 1 1 d . . . H4 H 0.5506 1.0432 0.5031 0.025 Uiso 1 1 calc R . . C5 C 0.5819(4) 1.3032(14) 0.5375(4) 0.028(2) Uani 1 1 d . . . C6 C 0.6122(4) 1.4049(12) 0.5980(5) 0.029(2) Uani 1 1 d . . . H6 H 0.6202 1.5342 0.5968 0.035 Uiso 1 1 calc R . . C7 C 0.6304(3) 1.3216(11) 0.6583(4) 0.0198(17) Uani 1 1 d . . . H7 H 0.6510 1.3940 0.6978 0.024 Uiso 1 1 calc R . . C8 C 0.5625(5) 1.3956(16) 0.4728(5) 0.049(3) Uani 1 1 d . . . H8A H 0.5912 1.3709 0.4596 0.073 Uiso 1 1 calc R . . H8B H 0.5593 1.5312 0.4771 0.073 Uiso 1 1 calc R . . H8C H 0.5240 1.3456 0.4389 0.073 Uiso 1 1 calc R . . C9 C 0.7075(3) 0.7611(11) 0.7783(4) 0.0170(16) Uani 1 1 d . . . C10 C 0.5903(3) 0.7488(11) 0.7365(4) 0.0178(16) Uani 1 1 d . . . C11 C 0.7612(4) 1.0499(12) 0.9439(4) 0.0231(19) Uani 1 1 d . . . H11 H 0.7519 0.9381 0.9585 0.028 Uiso 1 1 calc R . . C12 C 0.8056(4) 1.1624(13) 0.9904(5) 0.030(2) Uani 1 1 d . . . H12 H 0.8266 1.1275 1.0360 0.036 Uiso 1 1 calc R . . C13 C 0.8194(4) 1.3249(12) 0.9705(4) 0.0237(19) Uani 1 1 d . . . H13 H 0.8495 1.4050 1.0021 0.028 Uiso 1 1 calc R . . C14 C 0.7891(4) 1.3697(12) 0.9046(4) 0.0223(18) Uani 1 1 d . . . H14 H 0.7978 1.4814 0.8895 0.027 Uiso 1 1 calc R . . C15 C 0.7453(3) 1.2498(12) 0.8602(4) 0.0190(17) Uani 1 1 d . . . H15 H 0.7247 1.2813 0.8143 0.023 Uiso 1 1 calc R . . C21 C 0.5639(3) 0.9760(12) 0.8437(4) 0.0196(17) Uani 1 1 d . . . H21 H 0.5666 0.8432 0.8472 0.024 Uiso 1 1 calc R . . C22 C 0.5229(4) 1.0644(11) 0.8535(4) 0.0196(18) Uani 1 1 d . . . H22 H 0.4980 0.9941 0.8631 0.023 Uiso 1 1 calc R . . C23 C 0.5191(3) 1.2578(12) 0.8489(4) 0.0191(17) Uani 1 1 d . . . H23 H 0.4916 1.3232 0.8557 0.023 Uiso 1 1 calc R . . C24 C 0.5560(4) 1.3543(11) 0.8345(4) 0.0204(17) Uani 1 1 d . . . H24 H 0.5539 1.4871 0.8307 0.024 Uiso 1 1 calc R . . C25 C 0.5957(3) 1.2564(11) 0.8259(4) 0.0170(16) Uani 1 1 d . . . H25 H 0.6215 1.3243 0.8170 0.020 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 W1 0.0155(2) 0.0139(2) 0.0090(2) 0.00021(11) 0.00816(15) -0.00100(11) Cl1 0.0242(10) 0.0159(9) 0.0169(10) 0.0029(7) 0.0107(8) -0.0028(7) O1 0.031(3) 0.029(3) 0.031(4) -0.006(3) 0.025(3) 0.001(3) N1 0.015(3) 0.016(3) 0.013(3) 0.000(2) 0.009(3) -0.001(2) C1 0.010(4) 0.021(4) 0.023(4) -0.015(3) 0.010(3) -0.006(3) O2 0.025(3) 0.022(3) 0.020(3) -0.005(3) 0.009(3) -0.008(3) N2 0.016(3) 0.014(3) 0.012(3) 0.002(2) 0.009(3) -0.001(2) C2 0.008(3) 0.029(4) 0.010(4) -0.001(3) 0.006(3) -0.001(3) C3 0.019(4) 0.024(4) 0.018(4) 0.001(3) 0.014(4) -0.003(3) C4 0.022(4) 0.026(5) 0.015(4) 0.000(3) 0.011(4) -0.001(3) C5 0.029(5) 0.040(6) 0.013(4) 0.009(4) 0.009(4) 0.000(4) C6 0.034(5) 0.024(5) 0.022(5) 0.011(3) 0.010(4) -0.001(4) C7 0.023(4) 0.022(4) 0.016(4) -0.002(3) 0.012(4) 0.002(3) C8 0.051(7) 0.062(8) 0.022(6) 0.012(5) 0.011(5) -0.011(5) C9 0.018(4) 0.018(4) 0.014(4) 0.002(3) 0.007(3) -0.003(3) C10 0.015(4) 0.019(4) 0.023(4) 0.002(3) 0.013(3) -0.001(3) C11 0.032(5) 0.024(4) 0.011(4) 0.004(3) 0.009(4) -0.007(4) C12 0.033(5) 0.030(5) 0.020(5) 0.000(4) 0.008(4) -0.010(4) C13 0.028(5) 0.026(5) 0.015(4) -0.006(3) 0.010(4) -0.009(4) C14 0.024(4) 0.021(4) 0.023(5) 0.001(3) 0.013(4) -0.006(3) C15 0.017(4) 0.026(4) 0.015(4) 0.003(3) 0.009(3) -0.005(3) C21 0.019(4) 0.021(4) 0.024(5) -0.003(3) 0.015(4) -0.006(3) C22 0.021(4) 0.026(5) 0.015(4) -0.002(3) 0.012(4) -0.004(3) C23 0.019(4) 0.025(4) 0.011(4) -0.004(3) 0.006(3) 0.005(3) C24 0.025(4) 0.013(4) 0.023(4) -0.002(3) 0.012(4) 0.000(3) C25 0.019(4) 0.021(4) 0.011(4) -0.002(3) 0.008(3) -0.005(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 W1 C1 1.806(9) . ? W1 C10 1.984(8) . ? W1 C9 1.994(8) . ? W1 N2 2.261(7) . ? W1 N1 2.269(7) . ? W1 Cl1 2.5239(19) . ? O1 C9 1.155(10) . ? N1 C15 1.342(10) . ? N1 C11 1.348(11) . ? C1 C2 1.456(12) . ? O2 C10 1.152(9) . ? N2 C21 1.333(10) . ? N2 C25 1.352(10) . ? C2 C7 1.397(11) . ? C2 C3 1.409(11) . ? C3 C4 1.392(12) . ? C3 H3 0.9500 . ? C4 C5 1.388(12) . ? C4 H4 0.9500 . ? C5 C6 1.417(13) . ? C5 C8 1.484(13) . ? C6 C7 1.374(12) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C11 C12 1.376(12) . ? C11 H11 0.9500 . ? C12 C13 1.369(12) . ? C12 H12 0.9500 . ? C13 C14 1.362(12) . ? C13 H13 0.9500 . ? C14 C15 1.384(11) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C21 C22 1.379(12) . ? C21 H21 0.9500 . ? C22 C23 1.382(11) . ? C22 H22 0.9500 . ? C23 C24 1.379(12) . ? C23 H23 0.9500 . ? C24 C25 1.367(11) . ? C24 H24 0.9500 . ? C25 H25 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 C1 W1 C10 84.2(3) . . ? C1 W1 C9 85.7(3) . . ? C10 W1 C9 87.2(3) . . ? C1 W1 N2 98.2(3) . . ? C10 W1 N2 92.5(3) . . ? C9 W1 N2 176.1(3) . . ? C1 W1 N1 99.7(3) . . ? C10 W1 N1 175.4(3) . . ? C9 W1 N1 95.4(3) . . ? N2 W1 N1 84.6(2) . . ? C1 W1 Cl1 171.2(2) . . ? C10 W1 Cl1 87.8(2) . . ? C9 W1 Cl1 90.4(2) . . ? N2 W1 Cl1 85.70(16) . . ? N1 W1 Cl1 88.49(17) . . ? C15 N1 C11 116.4(7) . . ? C15 N1 W1 119.4(5) . . ? C11 N1 W1 124.3(5) . . ? C2 C1 W1 172.4(6) . . ? C21 N2 C25 117.3(7) . . ? C21 N2 W1 121.3(5) . . ? C25 N2 W1 120.9(5) . . ? C7 C2 C3 118.4(7) . . ? C7 C2 C1 120.6(7) . . ? C3 C2 C1 121.0(7) . . ? C4 C3 C2 119.3(8) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 123.3(8) . . ? C5 C4 H4 118.4 . . ? C3 C4 H4 118.4 . . ? C4 C5 C6 116.1(8) . . ? C4 C5 C8 122.8(9) . . ? C6 C5 C8 121.1(9) . . ? C7 C6 C5 121.9(8) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C2 121.1(8) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O1 C9 W1 176.1(7) . . ? O2 C10 W1 178.8(7) . . ? N1 C11 C12 122.9(8) . . ? N1 C11 H11 118.6 . . ? C12 C11 H11 118.6 . . ? C13 C12 C11 119.5(9) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 118.9(8) . . ? C14 C13 H13 120.6 . . ? C12 C13 H13 120.6 . . ? C13 C14 C15 118.9(8) . . ? C13 C14 H14 120.6 . . ? C15 C14 H14 120.6 . . ? N1 C15 C14 123.5(8) . . ? N1 C15 H15 118.3 . . ? C14 C15 H15 118.3 . . ? N2 C21 C22 123.5(8) . . ? N2 C21 H21 118.3 . . ? C22 C21 H21 118.3 . . ? C21 C22 C23 118.4(8) . . ? C21 C22 H22 120.8 . . ? C23 C22 H22 120.8 . . ? C24 C23 C22 118.9(8) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C25 C24 C23 119.2(8) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? N2 C25 C24 122.8(7) . . ? N2 C25 H25 118.6 . . ? C24 C25 H25 118.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1 W1 N1 C15 1.3(6) . . . . ? C9 W1 N1 C15 87.8(6) . . . . ? N2 W1 N1 C15 -96.1(6) . . . . ? Cl1 W1 N1 C15 178.1(6) . . . . ? C1 W1 N1 C11 -178.5(7) . . . . ? C9 W1 N1 C11 -92.0(7) . . . . ? N2 W1 N1 C11 84.2(7) . . . . ? Cl1 W1 N1 C11 -1.7(7) . . . . ? C1 W1 N2 C21 130.6(6) . . . . ? C10 W1 N2 C21 46.1(7) . . . . ? N1 W1 N2 C21 -130.3(6) . . . . ? Cl1 W1 N2 C21 -41.5(6) . . . . ? C1 W1 N2 C25 -41.4(6) . . . . ? C10 W1 N2 C25 -125.9(6) . . . . ? N1 W1 N2 C25 57.7(6) . . . . ? Cl1 W1 N2 C25 146.5(6) . . . . ? C7 C2 C3 C4 -0.4(11) . . . . ? C1 C2 C3 C4 179.3(7) . . . . ? C2 C3 C4 C5 0.4(13) . . . . ? C3 C4 C5 C6 -0.5(13) . . . . ? C3 C4 C5 C8 -179.7(9) . . . . ? C4 C5 C6 C7 0.6(14) . . . . ? C8 C5 C6 C7 179.8(10) . . . . ? C5 C6 C7 C2 -0.6(14) . . . . ? C3 C2 C7 C6 0.5(12) . . . . ? C1 C2 C7 C6 -179.2(8) . . . . ? C15 N1 C11 C12 0.5(13) . . . . ? W1 N1 C11 C12 -179.7(7) . . . . ? N1 C11 C12 C13 0.6(15) . . . . ? C11 C12 C13 C14 -0.9(14) . . . . ? C12 C13 C14 C15 0.3(13) . . . . ? C11 N1 C15 C14 -1.2(12) . . . . ? W1 N1 C15 C14 179.0(6) . . . . ? C13 C14 C15 N1 0.9(13) . . . . ? C25 N2 C21 C22 1.1(12) . . . . ? W1 N2 C21 C22 -171.2(6) . . . . ? N2 C21 C22 C23 -0.5(13) . . . . ? C21 C22 C23 C24 0.4(12) . . . . ? C22 C23 C24 C25 -0.8(12) . . . . ? C21 N2 C25 C24 -1.5(11) . . . . ? W1 N2 C25 C24 170.8(6) . . . . ? C23 C24 C25 N2 1.4(12) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 4.715 _refine_diff_density_min -2.208 _refine_diff_density_rms 0.292 #===END