# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_test _audit_creation_date 2013-08-28T16:19:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C19 H16 Cl O2 P S2' _chemical_formula_weight 406.86 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.6305(10) _cell_length_b 24.0872(16) _cell_length_c 10.8747(8) _cell_angle_alpha 90 _cell_angle_beta 98.829(2) _cell_angle_gamma 90 _cell_volume 3786.9(5) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.27 _exptl_crystal_density_diffrn 1.427 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.517 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7344 _exptl_absorpt_correction_T_max 0.8453 _exptl_absorpt_process_details 'Sadabs 2008 (Bruker AXS, 2008)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-CCD' _diffrn_measurement_method omega-scans _diffrn_reflns_av_R_equivalents 0.0406 _diffrn_reflns_av_unetI/netI 0.0291 _diffrn_reflns_number 45022 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 6660 _reflns_number_gt 5584 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SMART 5.622 (Bruker AXS, 2001)' _computing_cell_refinement 'SAINTPLUS 8.18C (Bruker APEX2, 2011)' _computing_data_reduction 'SAINTPLUS 8.18C (Bruker APEX2, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 V1.08 (Farrugia, 2001)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0618P)^2^+7.7678P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 6660 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.328 _refine_diff_density_min -1.013 _refine_diff_density_rms 0.081 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P1A P 0.38628(6) 0.48480(4) 0.28864(8) 0.0202(2) Uani 1 1 d . . . S1A S 0.50967(6) 0.45168(4) 0.31369(8) 0.0239(2) Uani 1 1 d . . . Cl1 Cl 0.27988(6) 0.57985(4) 0.38380(9) 0.0335(2) Uani 1 1 d . . . S2 S 0.43417(6) 0.60957(4) 0.25996(8) 0.0250(2) Uani 1 1 d . . . O1 O 0.36439(18) 0.62544(10) 0.1590(2) 0.0319(6) Uani 1 1 d . . . O2 O 0.52117(18) 0.58933(11) 0.2342(3) 0.0357(6) Uani 1 1 d . . . C1 C 0.3886(2) 0.55689(13) 0.3538(3) 0.0215(7) Uani 1 1 d . . . H1 H 0.4305 0.5559 0.4357 0.026 Uiso 1 1 calc R . . C2 C 0.3062(2) 0.44841(14) 0.3706(3) 0.0215(7) Uani 1 1 d . . . C3 C 0.2470(2) 0.40908(14) 0.3094(3) 0.0233(7) Uani 1 1 d . . . H3 H 0.2433 0.4042 0.2221 0.028 Uiso 1 1 calc R . . C4 C 0.1927(2) 0.37646(14) 0.3760(3) 0.0254(8) Uani 1 1 d . . . H4 H 0.1524 0.3493 0.334 0.03 Uiso 1 1 calc R . . C5 C 0.1973(2) 0.38356(14) 0.5019(3) 0.0249(8) Uani 1 1 d . . . H5 H 0.1599 0.3614 0.5467 0.03 Uiso 1 1 calc R . . C6 C 0.2560(3) 0.42271(15) 0.5638(3) 0.0273(8) Uani 1 1 d . . . H6 H 0.2586 0.4276 0.651 0.033 Uiso 1 1 calc R . . C7 C 0.3112(2) 0.45494(14) 0.4996(3) 0.0264(8) Uani 1 1 d . . . H7 H 0.3523 0.4814 0.5428 0.032 Uiso 1 1 calc R . . C8 C 0.3317(2) 0.49017(14) 0.1287(3) 0.0227(7) Uani 1 1 d . . . C9 C 0.2411(2) 0.50927(15) 0.1007(3) 0.0271(8) Uani 1 1 d . . . H9 H 0.2077 0.5192 0.1657 0.033 Uiso 1 1 calc R . . C10 C 0.2002(3) 0.51375(15) -0.0212(3) 0.0286(8) Uani 1 1 d . . . H10 H 0.1384 0.5267 -0.0404 0.034 Uiso 1 1 calc R . . C11 C 0.2484(3) 0.49949(15) -0.1162(3) 0.0292(8) Uani 1 1 d . . . H11 H 0.2192 0.5025 -0.2002 0.035 Uiso 1 1 calc R . . C12 C 0.3390(3) 0.48087(15) -0.0903(3) 0.0284(8) Uani 1 1 d . . . H12 H 0.3722 0.4718 -0.1561 0.034 Uiso 1 1 calc R . . C13 C 0.3809(3) 0.47557(15) 0.0328(3) 0.0268(8) Uani 1 1 d . . . H13 H 0.4425 0.4621 0.0518 0.032 Uiso 1 1 calc R . . C14 C 0.4547(2) 0.66564(14) 0.3649(3) 0.0254(8) Uani 1 1 d . . . C15 C 0.3942(3) 0.71017(15) 0.3574(4) 0.0302(8) Uani 1 1 d . . . H15 H 0.341 0.7113 0.2952 0.036 Uiso 1 1 calc R . . C16 C 0.4129(3) 0.75302(16) 0.4424(4) 0.0377(10) Uani 1 1 d . . . H16 H 0.3728 0.7842 0.4375 0.045 Uiso 1 1 calc R . . C17 C 0.4895(3) 0.75095(16) 0.5345(4) 0.0388(10) Uani 1 1 d . . . H17 H 0.5006 0.78 0.5939 0.047 Uiso 1 1 calc R . . C18 C 0.5499(3) 0.70649(18) 0.5398(4) 0.0428(10) Uani 1 1 d . . . H18 H 0.6033 0.7056 0.6015 0.051 Uiso 1 1 calc R . . C19 C 0.5328(3) 0.66356(16) 0.4561(4) 0.0354(9) Uani 1 1 d . . . H19 H 0.5738 0.6328 0.4603 0.043 Uiso 1 1 calc R . . Cl1_2 Cl 0.16922(6) 0.66903(3) 0.14289(8) 0.0248(2) Uani 1 1 d . . . S1_2 S -0.05418(6) 0.63435(4) -0.06387(8) 0.0250(2) Uani 1 1 d . . . S2_2 S 0.06049(5) 0.76684(3) 0.06264(7) 0.01781(18) Uani 1 1 d . . . P1_2 P -0.03390(6) 0.65522(3) 0.11025(7) 0.01545(19) Uani 1 1 d . . . O1_2 O 0.08098(16) 0.75443(9) -0.0595(2) 0.0214(5) Uani 1 1 d . . . O2_2 O -0.02612(16) 0.79268(10) 0.0752(2) 0.0255(5) Uani 1 1 d . . . C1_2 C 0.0647(2) 0.70375(12) 0.1537(3) 0.0152(6) Uani 1 1 d . . . H1_2 H 0.0657 0.7146 0.2427 0.018 Uiso 1 1 calc R . . C2_2 C -0.1335(2) 0.68421(13) 0.1667(3) 0.0164(6) Uani 1 1 d . . . C3_2 C -0.2177(2) 0.65831(14) 0.1252(3) 0.0251(8) Uani 1 1 d . . . H3_2 H -0.2213 0.6302 0.0634 0.03 Uiso 1 1 calc R . . C4_2 C -0.2964(2) 0.67350(15) 0.1737(4) 0.0303(8) Uani 1 1 d . . . H4_2 H -0.3535 0.6553 0.1459 0.036 Uiso 1 1 calc R . . C5_2 C -0.2922(2) 0.71466(15) 0.2616(4) 0.0288(8) Uani 1 1 d . . . H5_2 H -0.3463 0.7249 0.2945 0.035 Uiso 1 1 calc R . . C6_2 C -0.2091(2) 0.74136(14) 0.3026(3) 0.0250(8) Uani 1 1 d . . . H6_2 H -0.2067 0.7702 0.3626 0.03 Uiso 1 1 calc R . . C7_2 C -0.1294(2) 0.72601(13) 0.2564(3) 0.0188(7) Uani 1 1 d . . . H7_2 H -0.0723 0.7439 0.2856 0.023 Uiso 1 1 calc R . . C8_2 C 0.0210(2) 0.60800(13) 0.3438(3) 0.0211(7) Uani 1 1 d . . . H8_2 H 0.0119 0.6439 0.376 0.025 Uiso 1 1 calc R . . C9_2 C 0.0021(2) 0.59866(12) 0.2159(3) 0.0162(6) Uani 1 1 d . . . C10_2 C 0.0121(2) 0.54544(13) 0.1704(3) 0.0230(7) Uani 1 1 d . . . H10_2 H -0.0014 0.5384 0.0835 0.028 Uiso 1 1 calc R . . C11_2 C 0.0416(2) 0.50268(14) 0.2519(4) 0.0278(8) Uani 1 1 d . . . H11_2 H 0.0469 0.4662 0.2207 0.033 Uiso 1 1 calc R . . C12_2 C 0.0633(2) 0.51250(14) 0.3772(4) 0.0271(8) Uani 1 1 d . . . H12_2 H 0.0856 0.4831 0.4321 0.033 Uiso 1 1 calc R . . C13_2 C 0.0526(3) 0.56538(15) 0.4239(3) 0.0263(8) Uani 1 1 d . . . H13_2 H 0.067 0.5722 0.5108 0.032 Uiso 1 1 calc R . . C14_2 C 0.1524(2) 0.80630(12) 0.1419(3) 0.0194(7) Uani 1 1 d . . . C15_2 C 0.1418(3) 0.83160(14) 0.2536(4) 0.0320(9) Uani 1 1 d . . . H15_2 H 0.0855 0.8284 0.2863 0.038 Uiso 1 1 calc R . . C16_2 C 0.2151(3) 0.86157(16) 0.3161(4) 0.0413(11) Uani 1 1 d . . . H16_2 H 0.2095 0.8789 0.393 0.05 Uiso 1 1 calc R . . C17_2 C 0.2966(3) 0.86652(16) 0.2672(4) 0.0403(10) Uani 1 1 d . . . H17_2 H 0.3463 0.8875 0.3105 0.048 Uiso 1 1 calc R . . C18_2 C 0.3063(3) 0.84126(16) 0.1565(4) 0.0328(9) Uani 1 1 d . . . H18_2 H 0.3623 0.8452 0.1233 0.039 Uiso 1 1 calc R . . C19_2 C 0.2342(2) 0.81011(14) 0.0934(3) 0.0255(8) Uani 1 1 d . . . H19_2 H 0.241 0.7917 0.018 0.031 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 P1A 0.0198(4) 0.0175(4) 0.0235(5) -0.0003(4) 0.0037(3) -0.0010(3) S1A 0.0202(4) 0.0222(4) 0.0291(5) -0.0018(4) 0.0027(3) 0.0026(3) Cl1 0.0333(5) 0.0287(5) 0.0402(5) 0.0002(4) 0.0112(4) 0.0006(4) S2 0.0272(5) 0.0196(4) 0.0299(5) 0.0007(4) 0.0097(4) -0.0037(3) O1 0.0397(15) 0.0279(14) 0.0282(14) 0.0050(11) 0.0056(12) -0.0051(11) O2 0.0325(15) 0.0293(14) 0.0501(17) -0.0037(13) 0.0219(13) -0.0036(11) C1 0.0223(17) 0.0169(16) 0.0259(18) 0.0012(14) 0.0062(14) -0.0023(13) C2 0.0209(17) 0.0182(16) 0.0249(18) 0.0041(14) 0.0023(14) -0.0002(13) C3 0.0261(18) 0.0241(18) 0.0196(17) -0.0027(14) 0.0032(14) -0.0014(14) C4 0.0249(18) 0.0181(17) 0.032(2) -0.0019(15) 0.0011(15) -0.0043(14) C5 0.0247(18) 0.0181(17) 0.032(2) 0.0107(15) 0.0048(15) 0.0005(14) C6 0.036(2) 0.0277(19) 0.0186(17) 0.0041(15) 0.0042(15) 0.0049(16) C7 0.030(2) 0.0194(17) 0.0267(19) -0.0005(15) -0.0066(15) -0.0053(15) C8 0.0244(18) 0.0185(17) 0.0257(18) 0.0010(14) 0.0052(14) -0.0029(14) C9 0.0248(19) 0.033(2) 0.0242(18) 0.0001(15) 0.0063(15) -0.0019(15) C10 0.0253(19) 0.030(2) 0.030(2) 0.0003(16) 0.0021(16) -0.0051(15) C11 0.037(2) 0.0261(19) 0.0231(19) -0.0018(15) 0.0010(16) -0.0047(16) C12 0.039(2) 0.0236(18) 0.0255(19) -0.0028(15) 0.0124(16) -0.0019(16) C13 0.0258(18) 0.0260(18) 0.030(2) 0.0018(15) 0.0089(15) -0.0030(15) C14 0.0267(19) 0.0208(18) 0.0304(19) 0.0015(15) 0.0098(15) -0.0050(14) C15 0.030(2) 0.0226(18) 0.037(2) 0.0059(16) 0.0032(16) 0.0007(15) C16 0.039(2) 0.0212(19) 0.054(3) -0.0010(18) 0.011(2) 0.0023(17) C17 0.035(2) 0.027(2) 0.055(3) -0.0143(19) 0.007(2) -0.0061(17) C18 0.037(2) 0.036(2) 0.052(3) -0.011(2) -0.003(2) -0.0051(19) C19 0.030(2) 0.027(2) 0.050(3) -0.0028(18) 0.0049(18) 0.0008(16) Cl1_2 0.0229(4) 0.0199(4) 0.0317(5) 0.0037(3) 0.0042(3) 0.0026(3) S1_2 0.0327(5) 0.0278(5) 0.0139(4) -0.0050(3) 0.0018(3) -0.0063(4) S2_2 0.0209(4) 0.0146(4) 0.0189(4) 0.0052(3) 0.0060(3) 0.0019(3) P1_2 0.0188(4) 0.0135(4) 0.0139(4) -0.0008(3) 0.0022(3) -0.0019(3) O1_2 0.0276(13) 0.0214(12) 0.0156(11) 0.0045(9) 0.0045(10) 0.0000(10) O2_2 0.0225(12) 0.0218(12) 0.0341(14) 0.0116(11) 0.0110(11) 0.0076(10) C1_2 0.0178(16) 0.0128(15) 0.0151(15) 0.0018(12) 0.0029(12) 0.0004(12) C2_2 0.0177(16) 0.0134(15) 0.0181(16) 0.0053(13) 0.0023(13) 0.0019(12) C3_2 0.0233(18) 0.0186(17) 0.032(2) 0.0012(15) 0.0004(15) -0.0028(14) C4_2 0.0202(18) 0.0257(19) 0.044(2) 0.0063(17) 0.0015(16) -0.0042(15) C5_2 0.0219(18) 0.029(2) 0.037(2) 0.0139(17) 0.0109(16) 0.0076(15) C6_2 0.0298(19) 0.0222(18) 0.0244(18) 0.0060(15) 0.0086(15) 0.0065(15) C7_2 0.0190(17) 0.0174(16) 0.0198(16) 0.0047(13) 0.0027(13) 0.0001(13) C8_2 0.0302(19) 0.0122(15) 0.0210(17) -0.0013(13) 0.0041(14) -0.0023(13) C9_2 0.0173(16) 0.0122(15) 0.0199(16) 0.0007(12) 0.0052(13) -0.0003(12) C10_2 0.0237(18) 0.0166(16) 0.0300(19) -0.0047(14) 0.0079(15) -0.0029(14) C11_2 0.0278(19) 0.0132(16) 0.044(2) -0.0028(15) 0.0116(17) 0.0018(14) C12_2 0.0261(19) 0.0196(17) 0.037(2) 0.0103(15) 0.0079(16) 0.0025(14) C13_2 0.033(2) 0.0241(18) 0.0222(18) 0.0076(15) 0.0046(15) -0.0001(15) C14_2 0.0293(18) 0.0092(14) 0.0208(17) 0.0036(13) 0.0073(14) -0.0016(13) C15_2 0.052(2) 0.0148(17) 0.035(2) -0.0030(15) 0.0243(19) -0.0094(16) C16_2 0.069(3) 0.026(2) 0.032(2) -0.0117(17) 0.018(2) -0.021(2) C17_2 0.054(3) 0.028(2) 0.038(2) -0.0017(18) 0.004(2) -0.0221(19) C18_2 0.035(2) 0.029(2) 0.036(2) 0.0019(17) 0.0100(17) -0.0095(16) C19_2 0.031(2) 0.0203(17) 0.0267(18) 0.0002(15) 0.0109(15) -0.0010(15) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 P1A C8 1.804(4) . ? P1A C2 1.804(3) . ? P1A C1 1.874(3) . ? P1A S1A 1.9541(12) . ? Cl1 C1 1.762(3) . ? S2 O2 1.430(3) . ? S2 O1 1.432(3) . ? S2 C14 1.764(4) . ? S2 C1 1.818(3) . ? C2 C3 1.384(5) . ? C2 C7 1.402(5) . ? C3 C4 1.397(5) . ? C4 C5 1.371(5) . ? C5 C6 1.380(5) . ? C6 C7 1.384(5) . ? C8 C9 1.392(5) . ? C8 C13 1.400(5) . ? C9 C10 1.372(5) . ? C10 C11 1.380(5) . ? C11 C12 1.387(5) . ? C12 C13 1.390(5) . ? C14 C15 1.385(5) . ? C14 C19 1.395(5) . ? C15 C16 1.385(6) . ? C16 C17 1.383(6) . ? C17 C18 1.384(6) . ? C18 C19 1.375(6) . ? Cl1_2 C1_2 1.763(3) . ? S1_2 P1_2 1.9375(11) . ? S2_2 O2_2 1.437(2) . ? S2_2 O1_2 1.437(2) . ? S2_2 C14_2 1.760(3) . ? S2_2 C1_2 1.810(3) . ? P1_2 C2_2 1.806(3) . ? P1_2 C9_2 1.808(3) . ? P1_2 C1_2 1.861(3) . ? C2_2 C3_2 1.393(5) . ? C2_2 C7_2 1.396(5) . ? C3_2 C4_2 1.387(5) . ? C4_2 C5_2 1.372(5) . ? C5_2 C6_2 1.387(5) . ? C6_2 C7_2 1.390(5) . ? C8_2 C13_2 1.379(5) . ? C8_2 C9_2 1.394(5) . ? C9_2 C10_2 1.390(4) . ? C10_2 C11_2 1.384(5) . ? C11_2 C12_2 1.372(5) . ? C12_2 C13_2 1.389(5) . ? C14_2 C19_2 1.384(5) . ? C14_2 C15_2 1.388(5) . ? C15_2 C16_2 1.382(6) . ? C16_2 C17_2 1.383(6) . ? C17_2 C18_2 1.375(6) . ? C18_2 C19_2 1.386(5) . ? 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 C8 P1A C2 106.65(16) . . ? C8 P1A C1 106.14(16) . . ? C2 P1A C1 103.83(15) . . ? C8 P1A S1A 115.24(12) . . ? C2 P1A S1A 112.87(12) . . ? C1 P1A S1A 111.26(12) . . ? O2 S2 O1 119.47(17) . . ? O2 S2 C14 108.65(17) . . ? O1 S2 C14 108.78(17) . . ? O2 S2 C1 106.61(16) . . ? O1 S2 C1 109.72(16) . . ? C14 S2 C1 102.23(16) . . ? Cl1 C1 S2 107.70(17) . . ? Cl1 C1 P1A 113.35(18) . . ? S2 C1 P1A 114.93(18) . . ? C3 C2 C7 119.4(3) . . ? C3 C2 P1A 120.1(3) . . ? C7 C2 P1A 120.1(3) . . ? C2 C3 C4 120.0(3) . . ? C5 C4 C3 120.2(3) . . ? C4 C5 C6 120.2(3) . . ? C5 C6 C7 120.4(3) . . ? C6 C7 C2 119.8(3) . . ? C9 C8 C13 120.1(3) . . ? C9 C8 P1A 120.0(3) . . ? C13 C8 P1A 119.9(3) . . ? C10 C9 C8 119.8(3) . . ? C9 C10 C11 120.4(4) . . ? C10 C11 C12 120.7(3) . . ? C11 C12 C13 119.5(3) . . ? C12 C13 C8 119.5(3) . . ? C15 C14 C19 121.1(3) . . ? C15 C14 S2 120.8(3) . . ? C19 C14 S2 118.2(3) . . ? C14 C15 C16 118.6(4) . . ? C17 C16 C15 120.8(4) . . ? C16 C17 C18 119.9(4) . . ? C19 C18 C17 120.3(4) . . ? C18 C19 C14 119.3(4) . . ? O2_2 S2_2 O1_2 119.34(14) . . ? O2_2 S2_2 C14_2 109.75(15) . . ? O1_2 S2_2 C14_2 108.25(15) . . ? O2_2 S2_2 C1_2 105.56(14) . . ? O1_2 S2_2 C1_2 109.67(14) . . ? C14_2 S2_2 C1_2 103.06(15) . . ? C2_2 P1_2 C9_2 104.30(14) . . ? C2_2 P1_2 C1_2 107.78(14) . . ? C9_2 P1_2 C1_2 99.95(14) . . ? C2_2 P1_2 S1_2 114.97(11) . . ? C9_2 P1_2 S1_2 114.31(11) . . ? C1_2 P1_2 S1_2 114.06(11) . . ? Cl1_2 C1_2 S2_2 108.60(16) . . ? Cl1_2 C1_2 P1_2 109.38(16) . . ? S2_2 C1_2 P1_2 115.37(16) . . ? C3_2 C2_2 C7_2 119.4(3) . . ? C3_2 C2_2 P1_2 115.8(2) . . ? C7_2 C2_2 P1_2 124.5(2) . . ? C4_2 C3_2 C2_2 120.2(3) . . ? C5_2 C4_2 C3_2 120.3(3) . . ? C4_2 C5_2 C6_2 120.2(3) . . ? C5_2 C6_2 C7_2 120.2(3) . . ? C6_2 C7_2 C2_2 119.7(3) . . ? C13_2 C8_2 C9_2 120.4(3) . . ? C10_2 C9_2 C8_2 119.3(3) . . ? C10_2 C9_2 P1_2 120.3(3) . . ? C8_2 C9_2 P1_2 120.4(2) . . ? C11_2 C10_2 C9_2 119.8(3) . . ? C12_2 C11_2 C10_2 120.7(3) . . ? C11_2 C12_2 C13_2 120.0(3) . . ? C8_2 C13_2 C12_2 119.8(3) . . ? C19_2 C14_2 C15_2 121.6(3) . . ? C19_2 C14_2 S2_2 119.3(3) . . ? C15_2 C14_2 S2_2 119.1(3) . . ? C16_2 C15_2 C14_2 118.5(4) . . ? C15_2 C16_2 C17_2 120.4(4) . . ? C18_2 C17_2 C16_2 120.6(4) . . ? C17_2 C18_2 C19_2 120.0(4) . . ? C14_2 C19_2 C18_2 118.9(3) . . ? _database_code_depnum_ccdc_archive 'CCDC 959178' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sad _audit_creation_date 2013-08-30T09:04:13-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C54 H62 Cl2 Li2 O8 P2 S4' _chemical_formula_weight 1114 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.7500(9) _cell_length_b 14.3394(11) _cell_length_c 18.4650(15) _cell_angle_alpha 84.134(2) _cell_angle_beta 75.391(2) _cell_angle_gamma 84.850(2) _cell_volume 2733.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.19 _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.382 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6444 _exptl_absorpt_correction_T_max 0.7453 _exptl_absorpt_process_details 'Sadabs 2008 (Bruker AXS, 2008)' #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-CCD' _diffrn_measurement_method omega-scans _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_unetI/netI 0.0322 _diffrn_reflns_number 50285 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 26.46 _diffrn_reflns_theta_full 26.46 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _reflns_number_total 11260 _reflns_number_gt 8770 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SMART 5.622 (Bruker AXS, 2001)' _computing_cell_refinement 'SAINTPLUS 8.18C (Bruker APEX2, 2011)' _computing_data_reduction 'SAINTPLUS 8.18C (Bruker APEX2, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 V1.08 (Farrugia, 2001)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^+1.9751P] 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_number_reflns 11260 _refine_ls_number_parameters 649 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0598 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1257 _refine_ls_wR_factor_gt 0.1126 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.21 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.077 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Cl1 Cl 0.13225(5) 0.63615(4) 0.22677(3) 0.01542(12) Uani 1 1 d . . . Cl2 Cl 0.88103(5) 0.85469(4) 0.27832(3) 0.01567(12) Uani 1 1 d . . . S1 S 0.25935(6) 0.39560(4) 0.35516(3) 0.02345(14) Uani 1 1 d . . . S2 S 0.31366(5) 0.66844(3) 0.30727(3) 0.01086(12) Uani 1 1 d . . . S3 S 0.75176(6) 1.08730(4) 0.13994(3) 0.02381(14) Uani 1 1 d . . . S4 S 0.70016(5) 0.81499(3) 0.19990(3) 0.01088(12) Uani 1 1 d . . . P1 P 0.31553(5) 0.47360(4) 0.26030(3) 0.01242(12) Uani 1 1 d . . . P2 P 0.69776(5) 1.01429(4) 0.23757(3) 0.01290(12) Uani 1 1 d . . . O1 O 0.41730(13) 0.62180(10) 0.33823(8) 0.0146(3) Uani 1 1 d . . . O2 O 0.33975(13) 0.76036(10) 0.26765(8) 0.0149(3) Uani 1 1 d . . . O3 O 0.59631(13) 0.85908(10) 0.16815(8) 0.0146(3) Uani 1 1 d . . . O4 O 0.67504(14) 0.72531(10) 0.24354(8) 0.0160(3) Uani 1 1 d . . . O5 O 0.45903(14) 0.75024(11) 0.08170(8) 0.0199(3) Uani 1 1 d . . . O6 O 0.31552(14) 0.92096(11) 0.15359(10) 0.0256(4) Uani 1 1 d . . . O7 O 0.69055(14) 0.57174(11) 0.36824(10) 0.0240(4) Uani 1 1 d . . . O8 O 0.54107(14) 0.75001(11) 0.42466(8) 0.0187(3) Uani 1 1 d . . . C1 C 0.27464(19) 0.59525(14) 0.25336(11) 0.0125(4) Uani 1 1 d . . . C2 C 0.48930(19) 0.45753(15) 0.22304(11) 0.0135(4) Uani 1 1 d . . . C3 C 0.5488(2) 0.36907(16) 0.23396(12) 0.0192(5) Uani 1 1 d . . . H3 H 0.5003 0.3206 0.2639 0.023 Uiso 1 1 calc R . . C4 C 0.6791(2) 0.35112(17) 0.20121(14) 0.0250(5) Uani 1 1 d . . . H4 H 0.7193 0.2902 0.2078 0.03 Uiso 1 1 calc R . . C5 C 0.7502(2) 0.42279(19) 0.15883(13) 0.0260(5) Uani 1 1 d . . . H5 H 0.8393 0.4109 0.1366 0.031 Uiso 1 1 calc R . . C6 C 0.6920(2) 0.51106(17) 0.14885(13) 0.0216(5) Uani 1 1 d . . . H6 H 0.7415 0.5601 0.1205 0.026 Uiso 1 1 calc R . . C7 C 0.5607(2) 0.52895(16) 0.18010(12) 0.0165(4) Uani 1 1 d . . . H7 H 0.5203 0.5895 0.1721 0.02 Uiso 1 1 calc R . . C8 C 0.2524(2) 0.43583(15) 0.18605(12) 0.0172(4) Uani 1 1 d . . . C9 C 0.2942(2) 0.47636(17) 0.11311(13) 0.0219(5) Uani 1 1 d . . . H9 H 0.3572 0.5215 0.1026 0.026 Uiso 1 1 calc R . . C10 C 0.2453(3) 0.45166(19) 0.05566(15) 0.0311(6) Uani 1 1 d . . . H10 H 0.2733 0.4804 0.0062 0.037 Uiso 1 1 calc R . . C11 C 0.1549(3) 0.3844(2) 0.07112(17) 0.0359(7) Uani 1 1 d . . . H11 H 0.1207 0.3673 0.032 0.043 Uiso 1 1 calc R . . C12 C 0.1144(2) 0.34246(19) 0.14297(17) 0.0341(7) Uani 1 1 d . . . H12 H 0.0535 0.2958 0.1529 0.041 Uiso 1 1 calc R . . C13 C 0.1626(2) 0.36811(16) 0.20122(15) 0.0241(5) Uani 1 1 d . . . H13 H 0.1341 0.3395 0.2507 0.029 Uiso 1 1 calc R . . C14 C 0.17809(19) 0.69200(15) 0.38307(11) 0.0130(4) Uani 1 1 d . . . C15 C 0.1066(2) 0.77650(15) 0.38162(11) 0.0155(4) Uani 1 1 d . . . H15 H 0.1322 0.8238 0.342 0.019 Uiso 1 1 calc R . . C16 C -0.0038(2) 0.79184(16) 0.43902(12) 0.0186(5) Uani 1 1 d . . . H16 H -0.0539 0.8499 0.4387 0.022 Uiso 1 1 calc R . . C17 C -0.0402(2) 0.72223(16) 0.49645(12) 0.0193(5) Uani 1 1 d . . . H17 H -0.1146 0.7329 0.5359 0.023 Uiso 1 1 calc R . . C18 C 0.0316(2) 0.63716(16) 0.49655(12) 0.0197(5) Uani 1 1 d . . . H18 H 0.0054 0.5895 0.5358 0.024 Uiso 1 1 calc R . . C19 C 0.1419(2) 0.62077(15) 0.43958(12) 0.0168(4) Uani 1 1 d . . . H19 H 0.1911 0.5623 0.4393 0.02 Uiso 1 1 calc R . . C20 C 0.74013(19) 0.89378(14) 0.24930(11) 0.0125(4) Uani 1 1 d . . . C21 C 0.52377(19) 1.02996(15) 0.27452(11) 0.0140(4) Uani 1 1 d . . . C22 C 0.4617(2) 1.11575(16) 0.25798(13) 0.0198(5) Uani 1 1 d . . . H22 H 0.5092 1.1629 0.2254 0.024 Uiso 1 1 calc R . . C23 C 0.3308(2) 1.13303(17) 0.28869(14) 0.0252(5) Uani 1 1 d . . . H23 H 0.2892 1.1923 0.2781 0.03 Uiso 1 1 calc R . . C24 C 0.2609(2) 1.06361(18) 0.33475(14) 0.0252(5) Uani 1 1 d . . . H24 H 0.1712 1.0751 0.3556 0.03 Uiso 1 1 calc R . . C25 C 0.3217(2) 0.97757(17) 0.35048(12) 0.0203(5) Uani 1 1 d . . . H25 H 0.2731 0.9297 0.3813 0.024 Uiso 1 1 calc R . . C26 C 0.4534(2) 0.96062(15) 0.32144(12) 0.0157(4) Uani 1 1 d . . . H26 H 0.4952 0.902 0.3335 0.019 Uiso 1 1 calc R . . C27 C 0.7626(2) 1.05740(15) 0.30911(13) 0.0194(5) Uani 1 1 d . . . C28 C 0.8534(2) 1.12506(16) 0.29018(16) 0.0269(6) Uani 1 1 d . . . H28 H 0.8804 1.1513 0.2398 0.032 Uiso 1 1 calc R . . C29 C 0.9039(2) 1.15366(19) 0.34627(19) 0.0400(8) Uani 1 1 d . . . H29 H 0.9652 1.2002 0.334 0.048 Uiso 1 1 calc R . . C30 C 0.8660(3) 1.1152(2) 0.41925(19) 0.0428(8) Uani 1 1 d . . . H30 H 0.9021 1.1347 0.4568 0.051 Uiso 1 1 calc R . . C31 C 0.7754(3) 1.0483(2) 0.43802(16) 0.0357(7) Uani 1 1 d . . . H31 H 0.7494 1.0216 0.4883 0.043 Uiso 1 1 calc R . . C32 C 0.7230(2) 1.02067(18) 0.38317(13) 0.0244(5) Uani 1 1 d . . . H32 H 0.6592 0.976 0.3963 0.029 Uiso 1 1 calc R . . C33 C 0.83420(19) 0.78737(15) 0.12432(11) 0.0133(4) Uani 1 1 d . . . C34 C 0.9054(2) 0.70294(15) 0.12724(12) 0.0167(4) Uani 1 1 d . . . H34 H 0.881 0.6573 0.1683 0.02 Uiso 1 1 calc R . . C35 C 1.0139(2) 0.68530(17) 0.06894(13) 0.0214(5) Uani 1 1 d . . . H35 H 1.0636 0.6272 0.07 0.026 Uiso 1 1 calc R . . C36 C 1.0487(2) 0.75280(17) 0.00969(12) 0.0217(5) Uani 1 1 d . . . H36 H 1.1223 0.7406 -0.03 0.026 Uiso 1 1 calc R . . C37 C 0.9777(2) 0.83748(18) 0.00784(13) 0.0230(5) Uani 1 1 d . . . H37 H 1.0027 0.8834 -0.033 0.028 Uiso 1 1 calc R . . C38 C 0.8692(2) 0.85606(16) 0.06559(12) 0.0185(5) Uani 1 1 d . . . H38 H 0.8202 0.9145 0.0648 0.022 Uiso 1 1 calc R . . C41 C 0.5694(2) 0.7680(2) 0.02047(13) 0.0291(6) Uani 1 1 d . . . H41A H 0.6431 0.7237 0.0261 0.035 Uiso 1 1 calc R . . H41B H 0.5947 0.8329 0.0196 0.035 Uiso 1 1 calc R . . C42 C 0.5318(2) 0.75480(17) -0.05155(12) 0.0220(5) Uani 1 1 d . . . H42A H 0.6028 0.7219 -0.087 0.026 Uiso 1 1 calc R . . H42B H 0.5078 0.8158 -0.0764 0.026 Uiso 1 1 calc R . . C43 C 0.4166(2) 0.69514(19) -0.02400(13) 0.0273(6) Uani 1 1 d . . . H43A H 0.3589 0.7039 -0.0586 0.033 Uiso 1 1 calc R . . H43B H 0.4438 0.6276 -0.0174 0.033 Uiso 1 1 calc R . . C44 C 0.3530(2) 0.73439(19) 0.05074(13) 0.0261(5) Uani 1 1 d . . . H44A H 0.3016 0.7939 0.0434 0.031 Uiso 1 1 calc R . . H44B H 0.296 0.6889 0.0841 0.031 Uiso 1 1 calc R . . C45 C 0.3490(2) 1.00725(16) 0.10915(15) 0.0252(5) Uani 1 1 d . . . H45A H 0.3853 0.9956 0.0558 0.03 Uiso 1 1 calc R . . H45B H 0.4135 1.0376 0.1271 0.03 Uiso 1 1 calc R . . C46 C 0.2254(2) 1.06852(17) 0.11830(15) 0.0277(6) Uani 1 1 d . . . H46A H 0.2255 1.112 0.073 0.033 Uiso 1 1 calc R . . H46B H 0.2099 1.1052 0.1627 0.033 Uiso 1 1 calc R . . C47 C 0.1260(2) 0.99510(18) 0.12905(16) 0.0315(6) Uani 1 1 d . . . H47A H 0.0387 1.0202 0.1543 0.038 Uiso 1 1 calc R . . H47B H 0.1237 0.9724 0.0806 0.038 Uiso 1 1 calc R . . C48 C 0.1769(2) 0.91938(18) 0.17802(16) 0.0297(6) Uani 1 1 d . . . H48A H 0.1463 0.9322 0.2315 0.036 Uiso 1 1 calc R . . H48B H 0.1488 0.8575 0.1716 0.036 Uiso 1 1 calc R . . C49 C 0.6563(2) 0.47752(17) 0.39083(18) 0.0350(7) Uani 1 1 d . . . H49A H 0.5874 0.4628 0.3678 0.042 Uiso 1 1 calc R . . H49B H 0.6246 0.4688 0.4461 0.042 Uiso 1 1 calc R . . C50 C 0.7761(2) 0.41361(17) 0.36480(14) 0.0256(5) Uani 1 1 d . . . H50A H 0.7622 0.3694 0.3302 0.031 Uiso 1 1 calc R . . H50B H 0.8011 0.3772 0.408 0.031 Uiso 1 1 calc R . . C51 C 0.8791(2) 0.48073(17) 0.32440(15) 0.0286(6) Uani 1 1 d . . . H51A H 0.9637 0.4597 0.3346 0.034 Uiso 1 1 calc R . . H51B H 0.8878 0.4864 0.2695 0.034 Uiso 1 1 calc R . . C52 C 0.8279(2) 0.57168(17) 0.35765(15) 0.0267(5) Uani 1 1 d . . . H52A H 0.8505 0.5744 0.4061 0.032 Uiso 1 1 calc R . . H52B H 0.8628 0.6258 0.3231 0.032 Uiso 1 1 calc R . . C53 C 0.4253(2) 0.74282(18) 0.48443(12) 0.0234(5) Uani 1 1 d . . . H53A H 0.3905 0.6806 0.4873 0.028 Uiso 1 1 calc R . . H53B H 0.3588 0.792 0.4756 0.028 Uiso 1 1 calc R . . C54 C 0.4628(2) 0.75575(17) 0.55671(12) 0.0215(5) Uani 1 1 d . . . H54A H 0.393 0.7905 0.5915 0.026 Uiso 1 1 calc R . . H54B H 0.4842 0.6945 0.5823 0.026 Uiso 1 1 calc R . . C55 C 0.5808(2) 0.81262(18) 0.52862(13) 0.0251(5) Uani 1 1 d . . . H55A H 0.6362 0.8053 0.5645 0.03 Uiso 1 1 calc R . . H55B H 0.5566 0.8801 0.5188 0.03 Uiso 1 1 calc R . . C56 C 0.6462(2) 0.76768(18) 0.45628(14) 0.0253(5) Uani 1 1 d . . . H56A H 0.7054 0.8107 0.4216 0.03 Uiso 1 1 calc R . . H56B H 0.6955 0.7083 0.4668 0.03 Uiso 1 1 calc R . . Li1 Li 0.4287(3) 0.8175(3) 0.1728(2) 0.0155(7) Uani 1 1 d . . . Li2 Li 0.5793(3) 0.6722(2) 0.3390(2) 0.0156(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0114(2) 0.0200(3) 0.0163(3) -0.00215(19) -0.00622(19) 0.00028(19) Cl2 0.0109(2) 0.0202(3) 0.0171(3) -0.0023(2) -0.00592(19) 0.00022(19) S1 0.0261(3) 0.0191(3) 0.0185(3) 0.0058(2) 0.0043(2) -0.0027(2) S2 0.0080(2) 0.0136(3) 0.0103(2) 0.00016(18) -0.00081(18) -0.00274(18) S3 0.0224(3) 0.0199(3) 0.0221(3) 0.0077(2) 0.0039(2) -0.0016(2) S4 0.0078(2) 0.0134(3) 0.0108(2) -0.00039(18) -0.00073(18) -0.00275(18) P1 0.0103(3) 0.0133(3) 0.0126(3) 0.0004(2) -0.0007(2) -0.0027(2) P2 0.0099(3) 0.0129(3) 0.0149(3) 0.0007(2) -0.0014(2) -0.0025(2) O1 0.0098(7) 0.0190(8) 0.0159(7) -0.0010(6) -0.0046(6) -0.0022(6) O2 0.0132(7) 0.0145(7) 0.0148(7) 0.0011(6) 0.0013(6) -0.0057(6) O3 0.0091(7) 0.0211(8) 0.0144(7) -0.0009(6) -0.0036(6) -0.0027(6) O4 0.0143(7) 0.0150(8) 0.0162(8) 0.0005(6) 0.0012(6) -0.0048(6) O5 0.0144(7) 0.0326(9) 0.0124(8) -0.0006(6) -0.0004(6) -0.0089(7) O6 0.0098(7) 0.0207(9) 0.0415(10) 0.0125(7) -0.0031(7) -0.0015(6) O7 0.0128(8) 0.0187(8) 0.0403(10) 0.0031(7) -0.0082(7) -0.0016(6) O8 0.0143(7) 0.0268(9) 0.0146(8) -0.0031(6) -0.0010(6) -0.0053(6) C1 0.0111(9) 0.0140(10) 0.0128(10) -0.0011(8) -0.0037(8) -0.0014(8) C2 0.0125(10) 0.0180(11) 0.0107(10) -0.0033(8) -0.0031(8) -0.0017(8) C3 0.0206(11) 0.0191(11) 0.0188(11) -0.0031(9) -0.0065(9) 0.0004(9) C4 0.0234(12) 0.0260(13) 0.0286(13) -0.0109(10) -0.0131(10) 0.0112(10) C5 0.0102(10) 0.0438(15) 0.0256(13) -0.0155(11) -0.0039(9) 0.0036(10) C6 0.0126(10) 0.0318(13) 0.0202(12) -0.0092(10) 0.0007(9) -0.0060(9) C7 0.0134(10) 0.0204(11) 0.0150(11) -0.0030(8) -0.0012(8) -0.0014(8) C8 0.0129(10) 0.0170(11) 0.0224(12) -0.0065(9) -0.0046(9) 0.0007(8) C9 0.0192(11) 0.0264(13) 0.0223(12) -0.0077(10) -0.0069(9) -0.0003(9) C10 0.0307(14) 0.0398(15) 0.0279(14) -0.0141(11) -0.0151(11) 0.0065(12) C11 0.0262(13) 0.0448(17) 0.0471(18) -0.0255(14) -0.0232(13) 0.0079(12) C12 0.0153(12) 0.0299(14) 0.063(2) -0.0237(13) -0.0139(12) 0.0005(10) C13 0.0132(11) 0.0200(12) 0.0388(14) -0.0094(10) -0.0038(10) 0.0001(9) C14 0.0102(9) 0.0196(11) 0.0103(10) -0.0029(8) -0.0027(8) -0.0049(8) C15 0.0145(10) 0.0211(11) 0.0112(10) -0.0005(8) -0.0028(8) -0.0048(8) C16 0.0136(10) 0.0250(12) 0.0174(11) -0.0051(9) -0.0033(9) 0.0002(9) C17 0.0128(10) 0.0339(13) 0.0112(10) -0.0054(9) 0.0004(8) -0.0076(9) C18 0.0186(11) 0.0275(13) 0.0119(11) 0.0029(9) -0.0006(8) -0.0091(9) C19 0.0157(10) 0.0191(11) 0.0154(11) 0.0008(8) -0.0035(8) -0.0035(9) C20 0.0084(9) 0.0167(11) 0.0133(10) -0.0006(8) -0.0048(8) -0.0007(8) C21 0.0112(10) 0.0178(11) 0.0136(10) -0.0032(8) -0.0030(8) -0.0023(8) C22 0.0186(11) 0.0187(12) 0.0228(12) -0.0025(9) -0.0058(9) -0.0013(9) C23 0.0196(12) 0.0242(13) 0.0333(14) -0.0055(10) -0.0112(10) 0.0073(10) C24 0.0106(10) 0.0368(14) 0.0291(13) -0.0111(11) -0.0041(9) 0.0018(10) C25 0.0141(11) 0.0283(13) 0.0178(11) -0.0053(9) 0.0005(9) -0.0064(9) C26 0.0133(10) 0.0188(11) 0.0147(10) -0.0018(8) -0.0021(8) -0.0023(8) C27 0.0134(10) 0.0165(11) 0.0312(13) -0.0096(9) -0.0084(9) 0.0015(8) C28 0.0144(11) 0.0196(12) 0.0479(16) -0.0078(11) -0.0079(11) -0.0012(9) C29 0.0192(13) 0.0297(15) 0.080(2) -0.0243(15) -0.0215(14) 0.0003(11) C30 0.0303(15) 0.0506(19) 0.060(2) -0.0347(16) -0.0279(14) 0.0122(13) C31 0.0341(15) 0.0448(17) 0.0354(15) -0.0220(13) -0.0188(12) 0.0104(12) C32 0.0216(12) 0.0296(13) 0.0239(13) -0.0102(10) -0.0071(10) 0.0008(10) C33 0.0095(9) 0.0204(11) 0.0116(10) -0.0041(8) -0.0033(8) -0.0034(8) C34 0.0153(10) 0.0221(12) 0.0142(11) -0.0040(9) -0.0052(8) -0.0019(9) C35 0.0139(11) 0.0296(13) 0.0234(12) -0.0115(10) -0.0073(9) 0.0036(9) C36 0.0107(10) 0.0406(14) 0.0146(11) -0.0089(10) -0.0020(8) -0.0022(10) C37 0.0184(11) 0.0347(14) 0.0145(11) 0.0002(9) -0.0002(9) -0.0073(10) C38 0.0144(10) 0.0233(12) 0.0157(11) 0.0017(9) -0.0007(8) -0.0025(9) C41 0.0163(11) 0.0525(17) 0.0176(12) -0.0093(11) 0.0031(9) -0.0109(11) C42 0.0216(12) 0.0286(13) 0.0156(11) -0.0025(9) -0.0027(9) -0.0048(10) C43 0.0222(12) 0.0391(15) 0.0227(13) -0.0100(11) -0.0033(10) -0.0106(11) C44 0.0143(11) 0.0423(15) 0.0238(12) -0.0094(11) -0.0024(9) -0.0120(10) C45 0.0189(12) 0.0210(12) 0.0334(14) 0.0116(10) -0.0056(10) -0.0065(9) C46 0.0261(13) 0.0206(13) 0.0348(14) 0.0083(10) -0.0092(11) -0.0010(10) C47 0.0188(12) 0.0328(15) 0.0406(16) 0.0055(12) -0.0068(11) -0.0008(10) C48 0.0092(11) 0.0268(13) 0.0479(16) 0.0077(11) -0.0012(10) -0.0017(9) C49 0.0220(13) 0.0216(13) 0.0556(18) 0.0119(12) -0.0037(12) -0.0035(10) C50 0.0281(13) 0.0209(12) 0.0293(13) 0.0009(10) -0.0112(11) -0.0008(10) C51 0.0239(13) 0.0287(14) 0.0313(14) -0.0016(11) -0.0061(10) 0.0051(10) C52 0.0115(11) 0.0276(13) 0.0418(15) -0.0024(11) -0.0074(10) -0.0036(9) C53 0.0149(11) 0.0390(14) 0.0158(11) -0.0027(10) -0.0012(9) -0.0067(10) C54 0.0218(12) 0.0268(13) 0.0152(11) -0.0016(9) -0.0023(9) -0.0042(10) C55 0.0235(12) 0.0300(14) 0.0236(12) -0.0091(10) -0.0044(10) -0.0079(10) C56 0.0166(11) 0.0334(14) 0.0272(13) -0.0103(10) -0.0026(10) -0.0086(10) Li1 0.0116(16) 0.0196(19) 0.0155(18) 0.0018(14) -0.0038(14) -0.0045(14) Li2 0.0135(17) 0.0164(18) 0.0159(18) 0.0012(14) -0.0023(14) -0.0026(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Cl1 C1 1.757(2) . ? Cl2 C20 1.758(2) . ? S1 P1 1.9674(8) . ? S2 O2 1.4550(15) . ? S2 O1 1.4576(15) . ? S2 C1 1.665(2) . ? S2 C14 1.782(2) . ? S3 P2 1.9694(8) . ? S4 O4 1.4548(15) . ? S4 O3 1.4551(15) . ? S4 C20 1.670(2) . ? S4 C33 1.782(2) . ? P1 C1 1.760(2) . ? P1 C8 1.822(2) . ? P1 C2 1.823(2) . ? P2 C20 1.753(2) . ? P2 C27 1.822(2) . ? P2 C21 1.824(2) . ? O1 Li2 1.949(4) . ? O2 Li1 1.913(4) . ? O3 Li1 1.927(4) . ? O4 Li2 1.924(4) . ? O5 C41 1.438(3) . ? O5 C44 1.442(3) . ? O5 Li1 1.966(4) . ? O6 C45 1.434(3) . ? O6 C48 1.445(3) . ? O6 Li1 1.895(4) . ? O7 C49 1.425(3) . ? O7 C52 1.440(3) . ? O7 Li2 1.911(4) . ? O8 C53 1.444(3) . ? O8 C56 1.448(3) . ? O8 Li2 1.966(4) . ? C2 C3 1.388(3) . ? C2 C7 1.391(3) . ? C3 C4 1.391(3) . ? C4 C5 1.388(4) . ? C5 C6 1.377(4) . ? C6 C7 1.394(3) . ? C8 C13 1.389(3) . ? C8 C9 1.391(3) . ? C9 C10 1.385(3) . ? C10 C11 1.388(4) . ? C11 C12 1.380(4) . ? C12 C13 1.399(4) . ? C14 C15 1.377(3) . ? C14 C19 1.390(3) . ? C15 C16 1.395(3) . ? C16 C17 1.385(3) . ? C17 C18 1.384(3) . ? C18 C19 1.392(3) . ? C21 C22 1.389(3) . ? C21 C26 1.393(3) . ? C22 C23 1.388(3) . ? C23 C24 1.385(4) . ? C24 C25 1.382(3) . ? C25 C26 1.391(3) . ? C27 C32 1.389(3) . ? C27 C28 1.394(3) . ? C28 C29 1.395(4) . ? C29 C30 1.377(5) . ? C30 C31 1.386(4) . ? C31 C32 1.382(3) . ? C33 C34 1.377(3) . ? C33 C38 1.389(3) . ? C34 C35 1.398(3) . ? C35 C36 1.384(3) . ? C36 C37 1.377(3) . ? C37 C38 1.394(3) . ? C41 C42 1.518(3) . ? C42 C43 1.519(3) . ? C43 C44 1.517(3) . ? C45 C46 1.508(3) . ? C46 C47 1.530(3) . ? C47 C48 1.496(3) . ? C49 C50 1.515(3) . ? C50 C51 1.528(3) . ? C51 C52 1.498(3) . ? C53 C54 1.521(3) . ? C54 C55 1.520(3) . ? C55 C56 1.521(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S2 O1 115.42(9) . . ? O2 S2 C1 111.74(10) . . ? O1 S2 C1 107.95(9) . . ? O2 S2 C14 103.84(9) . . ? O1 S2 C14 108.42(9) . . ? C1 S2 C14 109.25(10) . . ? O4 S4 O3 116.01(9) . . ? O4 S4 C20 112.06(10) . . ? O3 S4 C20 107.19(9) . . ? O4 S4 C33 103.89(9) . . ? O3 S4 C33 108.10(9) . . ? C20 S4 C33 109.39(10) . . ? C1 P1 C8 101.12(10) . . ? C1 P1 C2 106.98(10) . . ? C8 P1 C2 102.78(9) . . ? C1 P1 S1 121.48(7) . . ? C8 P1 S1 111.60(8) . . ? C2 P1 S1 110.96(7) . . ? C20 P2 C27 100.41(10) . . ? C20 P2 C21 106.96(10) . . ? C27 P2 C21 103.62(10) . . ? C20 P2 S3 121.75(7) . . ? C27 P2 S3 111.71(8) . . ? C21 P2 S3 110.58(7) . . ? S2 O1 Li2 127.54(14) . . ? S2 O2 Li1 141.13(14) . . ? S4 O3 Li1 130.64(14) . . ? S4 O4 Li2 141.58(14) . . ? C41 O5 C44 108.23(17) . . ? C41 O5 Li1 120.11(17) . . ? C44 O5 Li1 120.35(17) . . ? C45 O6 C48 109.52(17) . . ? C45 O6 Li1 127.39(17) . . ? C48 O6 Li1 122.89(17) . . ? C49 O7 C52 107.06(18) . . ? C49 O7 Li2 125.29(18) . . ? C52 O7 Li2 126.62(18) . . ? C53 O8 C56 108.79(16) . . ? C53 O8 Li2 122.36(17) . . ? C56 O8 Li2 118.14(16) . . ? S2 C1 Cl1 111.39(11) . . ? S2 C1 P1 122.70(12) . . ? Cl1 C1 P1 119.12(11) . . ? C3 C2 C7 119.88(19) . . ? C3 C2 P1 118.08(16) . . ? C7 C2 P1 121.88(16) . . ? C2 C3 C4 120.3(2) . . ? C5 C4 C3 119.6(2) . . ? C6 C5 C4 120.3(2) . . ? C5 C6 C7 120.4(2) . . ? C2 C7 C6 119.6(2) . . ? C13 C8 C9 119.6(2) . . ? C13 C8 P1 121.16(18) . . ? C9 C8 P1 119.20(16) . . ? C10 C9 C8 120.8(2) . . ? C9 C10 C11 119.4(3) . . ? C12 C11 C10 120.3(2) . . ? C11 C12 C13 120.4(2) . . ? C8 C13 C12 119.4(2) . . ? C15 C14 C19 121.69(19) . . ? C15 C14 S2 119.84(16) . . ? C19 C14 S2 118.28(16) . . ? C14 C15 C16 119.3(2) . . ? C17 C16 C15 119.8(2) . . ? C18 C17 C16 120.25(19) . . ? C17 C18 C19 120.6(2) . . ? C14 C19 C18 118.4(2) . . ? S4 C20 P2 122.84(12) . . ? S4 C20 Cl2 111.05(11) . . ? P2 C20 Cl2 120.28(11) . . ? C22 C21 C26 119.56(19) . . ? C22 C21 P2 118.37(16) . . ? C26 C21 P2 121.99(16) . . ? C23 C22 C21 120.4(2) . . ? C24 C23 C22 119.8(2) . . ? C25 C24 C23 120.0(2) . . ? C24 C25 C26 120.4(2) . . ? C25 C26 C21 119.7(2) . . ? C32 C27 C28 119.7(2) . . ? C32 C27 P2 119.40(17) . . ? C28 C27 P2 120.92(19) . . ? C27 C28 C29 119.0(3) . . ? C30 C29 C28 120.8(3) . . ? C29 C30 C31 120.1(2) . . ? C32 C31 C30 119.6(3) . . ? C31 C32 C27 120.8(2) . . ? C34 C33 C38 121.54(19) . . ? C34 C33 S4 120.45(16) . . ? C38 C33 S4 117.85(16) . . ? C33 C34 C35 119.1(2) . . ? C36 C35 C34 119.8(2) . . ? C37 C36 C35 120.6(2) . . ? C36 C37 C38 120.3(2) . . ? C33 C38 C37 118.7(2) . . ? O5 C41 C42 107.36(18) . . ? C41 C42 C43 102.71(18) . . ? C44 C43 C42 101.21(18) . . ? O5 C44 C43 104.36(18) . . ? O6 C45 C46 105.78(18) . . ? C45 C46 C47 101.44(19) . . ? C48 C47 C46 101.4(2) . . ? O6 C48 C47 105.26(19) . . ? O7 C49 C50 107.39(19) . . ? C49 C50 C51 104.21(19) . . ? C52 C51 C50 102.78(19) . . ? O7 C52 C51 104.24(19) . . ? O8 C53 C54 106.60(17) . . ? C55 C54 C53 102.41(18) . . ? C54 C55 C56 100.98(18) . . ? O8 C56 C55 104.43(18) . . ? O6 Li1 O2 103.86(18) . . ? O6 Li1 O3 110.40(19) . . ? O2 Li1 O3 115.95(19) . . ? O6 Li1 O5 102.68(18) . . ? O2 Li1 O5 120.19(19) . . ? O3 Li1 O5 102.92(17) . . ? O7 Li2 O4 105.14(18) . . ? O7 Li2 O1 108.52(18) . . ? O4 Li2 O1 115.30(19) . . ? O7 Li2 O8 102.68(18) . . ? O4 Li2 O8 117.91(19) . . ? O1 Li2 O8 106.25(17) . . ? _database_code_depnum_ccdc_archive 'CCDC 959179' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_platon _audit_creation_date 2013-09-26T10:50:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C38 H32 O4 P2 Pd S4' _chemical_formula_weight 849.22 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.4275(16) _cell_length_b 9.8149(7) _cell_length_c 17.4155(12) _cell_angle_alpha 90 _cell_angle_beta 116.776(2) _cell_angle_gamma 90 _cell_volume 3575.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.21 _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.883 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6692 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details sadabs2008 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-CCD' _diffrn_measurement_method omega-scans _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_unetI/netI 0.0237 _diffrn_reflns_number 21522 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 3145 _reflns_number_gt 2768 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'SMART 5.622 (Bruker AXS, 2001)' _computing_cell_refinement 'SAINTPLUS 8.18C (Bruker APEX2, 2011)' _computing_data_reduction 'SAINTPLUS 8.18C (Bruker APEX2, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 V1.08 (Farrugia, 2001)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0291P)^2^+12.0897P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3145 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0715 _refine_ls_wR_factor_gt 0.068 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.841 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.076 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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' O O 0.0106 0.006 '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' Pd Pd -0.9988 1.0072 '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' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Pd1 Pd 0.5 0.12081(3) 0.25 0.01423(10) Uani 1 2 d S . . H1 H 0.4469(14) 0.338(3) 0.2689(19) 0.015(8) Uiso 1 1 d . . . S1 S 0.41870(3) -0.03213(8) 0.24337(4) 0.01855(17) Uani 1 1 d . . . S2 S 0.39654(3) 0.31988(8) 0.12768(4) 0.01869(17) Uani 1 1 d . . . P1 P 0.38781(3) 0.14641(8) 0.26699(4) 0.01562(17) Uani 1 1 d . . . O1 O 0.36413(10) 0.2064(2) 0.07300(12) 0.0250(5) Uani 1 1 d . . . O2 O 0.44568(10) 0.3895(2) 0.11465(13) 0.0277(5) Uani 1 1 d . . . C1 C 0.43024(13) 0.2658(3) 0.23508(18) 0.0171(6) Uani 1 1 d . . . C2 C 0.41343(13) 0.1767(3) 0.38043(17) 0.0185(6) Uani 1 1 d . . . C3 C 0.42040(13) 0.0654(3) 0.43349(18) 0.0226(7) Uani 1 1 d . . . H3 H 0.413 -0.0242 0.4103 0.027 Uiso 1 1 calc R . . C4 C 0.43822(14) 0.0852(4) 0.52048(19) 0.0286(8) Uani 1 1 d . . . H4 H 0.4427 0.0093 0.5566 0.034 Uiso 1 1 calc R . . C5 C 0.44928(15) 0.2140(4) 0.55379(19) 0.0319(8) Uani 1 1 d . . . H5 H 0.4611 0.2269 0.6131 0.038 Uiso 1 1 calc R . . C6 C 0.44354(16) 0.3270(4) 0.5021(2) 0.0320(8) Uani 1 1 d . . . H6 H 0.4522 0.4159 0.5261 0.038 Uiso 1 1 calc R . . C7 C 0.42492(14) 0.3075(3) 0.41458(19) 0.0246(7) Uani 1 1 d . . . H7 H 0.4201 0.3836 0.3785 0.03 Uiso 1 1 calc R . . C8 C 0.30128(13) 0.1568(3) 0.21531(18) 0.0187(6) Uani 1 1 d . . . C9 C 0.27022(15) 0.2559(4) 0.23984(19) 0.0285(7) Uani 1 1 d . . . H9 H 0.2944 0.3165 0.2856 0.034 Uiso 1 1 calc R . . C10 C 0.20494(16) 0.2662(4) 0.1982(2) 0.0367(9) Uani 1 1 d . . . H10 H 0.184 0.3355 0.2142 0.044 Uiso 1 1 calc R . . C11 C 0.16926(15) 0.1758(4) 0.1328(2) 0.0309(8) Uani 1 1 d . . . H11 H 0.1239 0.182 0.1046 0.037 Uiso 1 1 calc R . . C12 C 0.20019(15) 0.0762(3) 0.1087(2) 0.0271(7) Uani 1 1 d . . . H12 H 0.176 0.0141 0.0639 0.033 Uiso 1 1 calc R . . C13 C 0.26523(14) 0.0676(3) 0.14927(18) 0.0210(6) Uani 1 1 d . . . H13 H 0.2861 -0.0002 0.1322 0.025 Uiso 1 1 calc R . . C14 C 0.33874(13) 0.4447(3) 0.11482(17) 0.0200(6) Uani 1 1 d . . . C15 C 0.27422(14) 0.4121(3) 0.07370(18) 0.0228(7) Uani 1 1 d . . . H15 H 0.261 0.3209 0.057 0.027 Uiso 1 1 calc R . . C16 C 0.22946(14) 0.5138(3) 0.05732(19) 0.0247(7) Uani 1 1 d . . . H16 H 0.1852 0.4922 0.0291 0.03 Uiso 1 1 calc R . . C17 C 0.24842(16) 0.6451(4) 0.0815(2) 0.0354(8) Uani 1 1 d . . . H17 H 0.2174 0.7146 0.0702 0.042 Uiso 1 1 calc R . . C18 C 0.31292(17) 0.6765(4) 0.1223(2) 0.0400(9) Uani 1 1 d . . . H18 H 0.3259 0.7682 0.1382 0.048 Uiso 1 1 calc R . . C19 C 0.35798(15) 0.5783(4) 0.1402(2) 0.0302(8) Uani 1 1 d . . . H19 H 0.4021 0.6006 0.1697 0.036 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 Pd1 0.01178(15) 0.01649(18) 0.01350(16) 0 0.00488(12) 0 S1 0.0178(3) 0.0167(4) 0.0221(4) -0.0024(3) 0.0098(3) -0.0020(3) S2 0.0164(3) 0.0224(4) 0.0166(4) 0.0035(3) 0.0069(3) 0.0028(3) P1 0.0137(3) 0.0184(4) 0.0141(3) -0.0006(3) 0.0058(3) -0.0003(3) O1 0.0259(11) 0.0274(13) 0.0173(10) -0.0024(9) 0.0060(9) 0.0046(10) O2 0.0215(11) 0.0346(13) 0.0291(12) 0.0145(10) 0.0132(9) 0.0056(10) C1 0.0152(14) 0.0171(16) 0.0154(14) -0.0012(12) 0.0037(11) -0.0022(12) C2 0.0136(13) 0.0271(17) 0.0145(14) -0.0021(12) 0.0060(11) -0.0011(12) C3 0.0166(14) 0.0281(17) 0.0213(15) 0.0012(13) 0.0069(12) 0.0014(13) C4 0.0220(16) 0.043(2) 0.0188(15) 0.0085(14) 0.0073(13) 0.0053(15) C5 0.0272(17) 0.051(2) 0.0136(15) -0.0009(15) 0.0059(13) 0.0115(16) C6 0.0316(18) 0.036(2) 0.0268(17) -0.0111(15) 0.0116(15) 0.0047(16) C7 0.0277(17) 0.0261(18) 0.0218(16) -0.0008(13) 0.0127(13) 0.0025(14) C8 0.0143(14) 0.0232(17) 0.0184(14) 0.0040(12) 0.0073(12) 0.0020(12) C9 0.0225(16) 0.040(2) 0.0211(16) -0.0075(14) 0.0085(13) 0.0014(15) C10 0.0258(17) 0.058(3) 0.0283(18) 0.0023(17) 0.0143(15) 0.0186(17) C11 0.0164(15) 0.050(2) 0.0255(17) 0.0057(15) 0.0084(13) 0.0026(15) C12 0.0252(16) 0.0293(18) 0.0231(16) 0.0022(13) 0.0075(13) -0.0094(14) C13 0.0231(15) 0.0176(16) 0.0171(14) 0.0038(12) 0.0046(12) -0.0007(13) C14 0.0191(14) 0.0257(17) 0.0137(14) 0.0034(12) 0.0061(11) 0.0029(13) C15 0.0204(15) 0.0241(17) 0.0218(15) -0.0005(12) 0.0077(12) 0.0006(13) C16 0.0167(15) 0.0344(19) 0.0209(15) -0.0012(13) 0.0066(12) 0.0028(14) C17 0.0300(18) 0.033(2) 0.0368(19) -0.0021(15) 0.0098(15) 0.0134(16) C18 0.038(2) 0.0222(19) 0.050(2) -0.0083(16) 0.0118(18) -0.0012(16) C19 0.0225(16) 0.0295(19) 0.0323(18) -0.0028(14) 0.0068(14) -0.0001(14) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Pd1 C1 2.093(3) . ? Pd1 C1 2.093(3) 2_655 ? Pd1 S1 2.3866(8) . ? Pd1 S1 2.3867(8) 2_655 ? Pd1 P1 2.7857(7) . ? Pd1 P1 2.7859(7) 2_655 ? S1 P1 2.0080(10) . ? S2 O1 1.440(2) . ? S2 O2 1.442(2) . ? S2 C1 1.753(3) . ? S2 C14 1.764(3) . ? P1 C1 1.780(3) . ? P1 C2 1.812(3) . ? P1 C8 1.813(3) . ? C2 C7 1.389(4) . ? C2 C3 1.392(4) . ? C3 C4 1.392(4) . ? C4 C5 1.367(5) . ? C5 C6 1.396(5) . ? C6 C7 1.396(4) . ? C8 C13 1.388(4) . ? C8 C9 1.392(4) . ? C9 C10 1.369(4) . ? C10 C11 1.388(5) . ? C11 C12 1.390(5) . ? C12 C13 1.363(4) . ? C14 C15 1.387(4) . ? C14 C19 1.393(5) . ? C15 C16 1.381(4) . ? C16 C17 1.367(5) . ? C17 C18 1.384(5) . ? C18 C19 1.358(5) . ? 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 Pd1 C1 94.33(16) . 2_655 ? C1 Pd1 S1 81.96(8) . . ? C1 Pd1 S1 174.33(8) 2_655 . ? C1 Pd1 S1 174.33(8) . 2_655 ? C1 Pd1 S1 81.96(8) 2_655 2_655 ? S1 Pd1 S1 102.05(4) . 2_655 ? C1 Pd1 P1 39.69(8) . . ? C1 Pd1 P1 130.30(8) 2_655 . ? S1 Pd1 P1 44.87(2) . . ? S1 Pd1 P1 145.30(3) 2_655 . ? C1 Pd1 P1 130.30(8) . 2_655 ? C1 Pd1 P1 39.69(8) 2_655 2_655 ? S1 Pd1 P1 145.30(3) . 2_655 ? S1 Pd1 P1 44.87(2) 2_655 2_655 ? P1 Pd1 P1 169.65(3) . 2_655 ? P1 S1 Pd1 78.15(3) . . ? O1 S2 O2 118.88(13) . . ? O1 S2 C1 108.74(14) . . ? O2 S2 C1 107.68(13) . . ? O1 S2 C14 107.89(13) . . ? O2 S2 C14 105.83(14) . . ? C1 S2 C14 107.26(14) . . ? C1 P1 C2 105.97(14) . . ? C1 P1 C8 117.71(13) . . ? C2 P1 C8 106.22(13) . . ? C1 P1 S1 101.94(10) . . ? C2 P1 S1 113.18(10) . . ? C8 P1 S1 111.90(10) . . ? C1 P1 Pd1 48.68(10) . . ? C2 P1 Pd1 105.40(9) . . ? C8 P1 Pd1 148.20(9) . . ? S1 P1 Pd1 56.98(3) . . ? S2 C1 P1 119.08(16) . . ? S2 C1 Pd1 106.83(14) . . ? P1 C1 Pd1 91.63(13) . . ? C7 C2 C3 119.9(3) . . ? C7 C2 P1 121.6(2) . . ? C3 C2 P1 118.5(2) . . ? C4 C3 C2 120.0(3) . . ? C5 C4 C3 119.8(3) . . ? C4 C5 C6 121.1(3) . . ? C5 C6 C7 119.2(3) . . ? C2 C7 C6 119.9(3) . . ? C13 C8 C9 119.2(3) . . ? C13 C8 P1 120.2(2) . . ? C9 C8 P1 120.6(2) . . ? C10 C9 C8 120.2(3) . . ? C9 C10 C11 120.2(3) . . ? C10 C11 C12 119.6(3) . . ? C13 C12 C11 120.0(3) . . ? C12 C13 C8 120.7(3) . . ? C15 C14 C19 120.1(3) . . ? C15 C14 S2 120.1(2) . . ? C19 C14 S2 119.6(2) . . ? C16 C15 C14 119.3(3) . . ? C17 C16 C15 120.4(3) . . ? C16 C17 C18 119.8(3) . . ? C19 C18 C17 121.1(3) . . ? C18 C19 C14 119.2(3) . . ? _database_code_depnum_ccdc_archive 'CCDC 963531'