# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_PPNdopdtc #=============================================================================== # 5. CHEMICAL DATA _chemical_formula_sum 'C47 H38 N4 P2 S2' _chemical_formula_moiety 'C36 H30 N P2, C11 H8 N3 S2' _chemical_formula_weight 784.89 #============================================================= # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 #------------------------------------------------ _cell_length_a 15.6667(2) _cell_length_b 15.4415(2) _cell_length_c 17.7248(2) _cell_angle_alpha 90 _cell_angle_beta 107.7150(10) _cell_angle_gamma 90 _cell_volume 4084.61(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 26.70 _cell_measurement_temperature 293 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.172 _exptl_crystal_size_mid 0.319 _exptl_crystal_size_max 0.355 _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1640 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.916 _exptl_absorpt_correction_T_max 0.958 #============================================================================= # 7. EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_method \w/2\q _diffrn_ambient_temperature 293 _diffrn_reflns_number 52616 _diffrn_reflns_av_R_equivalents 0.024 _diffrn_reflns_theta_min 1.364 _diffrn_reflns_theta_max 26.727 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.727 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 #========================================================================== # 8. REFINEMENT DATA # The values actually used during refinement # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _oxford_reflns_threshold_expression_ref I>2.5\s(I) _refine_ls_number_reflns 6842 _refine_ls_number_restraints 0 _refine_ls_number_parameters 534 _oxford_refine_ls_R_factor_ref 0.0367 _refine_ls_wR_factor_ref 0.0380 _refine_ls_goodness_of_fit_ref 1.1107 # The values computed from all data _oxford_reflns_number_all 8647 _refine_ls_R_factor_all 0.0506 _refine_ls_wR_factor_all 0.0554 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 7278 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_gt 0.0383 _reflns_number_total 8647 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.155 0.138 0.597E-01 0.127E-01 0.317E-02 ; _refine_ls_shift/su_max 0.0006365 _refine_diff_density_min -0.36 _refine_diff_density_max 0.57 _reflns_limit_h_min -19 _reflns_limit_h_max 18 _reflns_limit_k_min 0 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_refine_ls_scale 0.09434(9) _oxford_diffrn_Wilson_B_factor 2.95 _oxford_diffrn_Wilson_scale 13.27 # Number of reflections without Friedels Law is 5877 # Number of reflections with Friedels Law is 3336 # Theoretical number of reflections is about 3131 #--------------------------------------------------------- _chemical_name_systematic ; ; # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens diffmap # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr # none if no extinction, _refine_ls_extinction_method None # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . #========================================================== # 9. General computing _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_structure_solution ; SIR92 (Altomare et al, 1994) CRYSTALS (Watkin, 1988) ; #=================================================================== # 10. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' #============================================================================== # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # TODO check _oxford_atom_site_special_shape 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens S1 S 0.23934(4) -0.31574(3) 0.46407(3) 0.0551 1.0000 Uani . . . . . . S2 S 0.16745(3) -0.15330(3) 0.37624(3) 0.0494 1.0000 Uani . . . . . . P1 P 0.28643(2) 0.19915(2) 0.42581(2) 0.0299 1.0000 Uani . . . . . . P2 P 0.10936(2) 0.19446(2) 0.30067(2) 0.0306 1.0000 Uani . . . . . . N1 N 0.44239(10) -0.31559(10) 0.38259(9) 0.0519 1.0000 Uani . . . . . . N2 N 0.32393(11) -0.17374(11) 0.24857(10) 0.0539 1.0000 Uani . . . . . . N3 N 0.30820(10) -0.23982(9) 0.36200(9) 0.0452 1.0000 Uani . . . . . . N4 N 0.20241(9) 0.16477(9) 0.35901(7) 0.0378 1.0000 Uani . . . . . . C1 C 0.35373(12) -0.31838(11) 0.35643(10) 0.0404 1.0000 Uani . . . . . . C2 C 0.30582(13) -0.39123(12) 0.32215(11) 0.0496 1.0000 Uani . . . . . . C3 C 0.35190(15) -0.46576(13) 0.31834(12) 0.0577 1.0000 Uani . . . . . . C4 C 0.44374(16) -0.46540(14) 0.34831(13) 0.0635 1.0000 Uani . . . . . . C5 C 0.48546(15) -0.38982(15) 0.37819(13) 0.0624 1.0000 Uani . . . . . . C6 C 0.33179(12) -0.16560(11) 0.32474(11) 0.0439 1.0000 Uani . . . . . . C7 C 0.36366(14) -0.09203(12) 0.36846(13) 0.0572 1.0000 Uani . . . . . . C8 C 0.38442(16) -0.02176(14) 0.32947(17) 0.0732 1.0000 Uani . . . . . . C9 C 0.37303(16) -0.02760(15) 0.24984(17) 0.0760 1.0000 Uani . . . . . . C10 C 0.34517(15) -0.10420(15) 0.21249(14) 0.0677 1.0000 Uani . . . . . . C11 C 0.24094(11) -0.23643(11) 0.39899(10) 0.0400 1.0000 Uani . . . . . . C12 C 0.27114(10) 0.30099(10) 0.46974(9) 0.0354 1.0000 Uani . . . . . . C13 C 0.22151(15) 0.30318(12) 0.52213(13) 0.0595 1.0000 Uani . . . . . . C14 C 0.20356(17) 0.38149(14) 0.55220(14) 0.0693 1.0000 Uani . . . . . . C15 C 0.23459(14) 0.45710(12) 0.53049(11) 0.0534 1.0000 Uani . . . . . . C16 C 0.28386(15) 0.45561(12) 0.47881(13) 0.0592 1.0000 Uani . . . . . . C17 C 0.30220(14) 0.37761(11) 0.44831(11) 0.0509 1.0000 Uani . . . . . . C18 C 0.37935(11) 0.21146(10) 0.38685(9) 0.0369 1.0000 Uani . . . . . . C19 C 0.36395(14) 0.20643(13) 0.30593(11) 0.0541 1.0000 Uani . . . . . . C20 C 0.43482(18) 0.21414(16) 0.27496(15) 0.0737 1.0000 Uani . . . . . . C21 C 0.52031(18) 0.22604(16) 0.32397(18) 0.0777 1.0000 Uani . . . . . . C22 C 0.53558(16) 0.23154(18) 0.40372(18) 0.0831 1.0000 Uani . . . . . . C23 C 0.46578(13) 0.22428(15) 0.43579(13) 0.0607 1.0000 Uani . . . . . . C24 C 0.31524(10) 0.12093(10) 0.50483(9) 0.0346 1.0000 Uani . . . . . . C25 C 0.27861(12) 0.03879(11) 0.49143(10) 0.0437 1.0000 Uani . . . . . . C26 C 0.30109(16) -0.02264(13) 0.55114(12) 0.0597 1.0000 Uani . . . . . . C27 C 0.35923(17) -0.00177(14) 0.62371(12) 0.0666 1.0000 Uani . . . . . . C28 C 0.39520(15) 0.07979(15) 0.63799(11) 0.0643 1.0000 Uani . . . . . . C29 C 0.37411(13) 0.14157(13) 0.57890(10) 0.0500 1.0000 Uani . . . . . . C30 C 0.11185(10) 0.29876(10) 0.25550(9) 0.0351 1.0000 Uani . . . . . . C31 C 0.14231(14) 0.30507(12) 0.19001(11) 0.0514 1.0000 Uani . . . . . . C32 C 0.15108(15) 0.38501(13) 0.15841(11) 0.0596 1.0000 Uani . . . . . . C33 C 0.12907(14) 0.45891(13) 0.19119(13) 0.0601 1.0000 Uani . . . . . . C34 C 0.10055(16) 0.45329(13) 0.25715(15) 0.0685 1.0000 Uani . . . . . . C35 C 0.09238(14) 0.37365(12) 0.28959(13) 0.0541 1.0000 Uani . . . . . . C36 C 0.07826(10) 0.11620(10) 0.22166(8) 0.0327 1.0000 Uani . . . . . . C37 C 0.00559(11) 0.13152(11) 0.15466(9) 0.0410 1.0000 Uani . . . . . . C38 C -0.01960(12) 0.06834(13) 0.09681(10) 0.0509 1.0000 Uani . . . . . . C39 C 0.02638(13) -0.00895(12) 0.10551(10) 0.0509 1.0000 Uani . . . . . . C40 C 0.09814(13) -0.02416(11) 0.17174(11) 0.0474 1.0000 Uani . . . . . . C41 C 0.12450(11) 0.03842(10) 0.23041(10) 0.0397 1.0000 Uani . . . . . . C42 C 0.02413(10) 0.19480(10) 0.34965(9) 0.0371 1.0000 Uani . . . . . . C43 C -0.05967(12) 0.23042(12) 0.31449(12) 0.0506 1.0000 Uani . . . . . . C44 C -0.12380(14) 0.22856(14) 0.35361(14) 0.0613 1.0000 Uani . . . . . . C45 C -0.10466(14) 0.19213(15) 0.42748(13) 0.0645 1.0000 Uani . . . . . . C46 C -0.02287(15) 0.15398(19) 0.46156(12) 0.0741 1.0000 Uani . . . . . . C47 C 0.04179(13) 0.15462(15) 0.42288(11) 0.0586 1.0000 Uani . . . . . . H21 H 0.2424 -0.3890 0.3018 0.063(6) 1.0000 Uiso R . . . . . H31 H 0.3210 -0.5167 0.2951 0.067(6) 1.0000 Uiso R . . . . . H41 H 0.4774 -0.5167 0.3489 0.076(7) 1.0000 Uiso R . . . . . H51 H 0.5490 -0.3890 0.3969 0.076(7) 1.0000 Uiso R . . . . . H71 H 0.3712 -0.0906 0.4236 0.054(5) 1.0000 Uiso R . . . . . H81 H 0.4066 0.0301 0.3573 0.081(7) 1.0000 Uiso R . . . . . H91 H 0.3841 0.0207 0.2210 0.102(9) 1.0000 Uiso R . . . . . H101 H 0.3405 -0.1093 0.1580 0.088(8) 1.0000 Uiso R . . . . . H131 H 0.1998 0.2507 0.5374 0.080(7) 1.0000 Uiso R . . . . . H141 H 0.1690 0.3828 0.5878 0.088(8) 1.0000 Uiso R . . . . . H151 H 0.2220 0.5107 0.5512 0.064(6) 1.0000 Uiso R . . . . . H161 H 0.3058 0.5081 0.4638 0.069(6) 1.0000 Uiso R . . . . . H171 H 0.3366 0.3766 0.4125 0.066(6) 1.0000 Uiso R . . . . . H191 H 0.3047 0.1975 0.2722 0.078(7) 1.0000 Uiso R . . . . . H201 H 0.4240 0.2111 0.2193 0.098(9) 1.0000 Uiso R . . . . . H211 H 0.5688 0.2306 0.3026 0.090(8) 1.0000 Uiso R . . . . . H221 H 0.5948 0.2403 0.4376 0.092(8) 1.0000 Uiso R . . . . . H231 H 0.4765 0.2280 0.4914 0.082(7) 1.0000 Uiso R . . . . . H251 H 0.2380 0.0247 0.4412 0.055(5) 1.0000 Uiso R . . . . . H261 H 0.2762 -0.0791 0.5418 0.075(7) 1.0000 Uiso R . . . . . H271 H 0.3752 -0.0440 0.6645 0.076(7) 1.0000 Uiso R . . . . . H281 H 0.4341 0.0943 0.6889 0.081(7) 1.0000 Uiso R . . . . . H291 H 0.4000 0.1977 0.5881 0.060(6) 1.0000 Uiso R . . . . . H311 H 0.1568 0.2539 0.1668 0.071(7) 1.0000 Uiso R . . . . . H321 H 0.1733 0.3887 0.1143 0.077(7) 1.0000 Uiso R . . . . . H331 H 0.1332 0.5137 0.1682 0.073(7) 1.0000 Uiso R . . . . . H341 H 0.0861 0.5044 0.2804 0.091(8) 1.0000 Uiso R . . . . . H351 H 0.0734 0.3700 0.3355 0.069(6) 1.0000 Uiso R . . . . . H371 H -0.0259 0.1849 0.1488 0.045(5) 1.0000 Uiso R . . . . . H381 H -0.0691 0.0780 0.0510 0.064(6) 1.0000 Uiso R . . . . . H391 H 0.0082 -0.0520 0.0656 0.058(6) 1.0000 Uiso R . . . . . H401 H 0.1300 -0.0772 0.1769 0.054(5) 1.0000 Uiso R . . . . . H411 H 0.1736 0.0282 0.2765 0.046(5) 1.0000 Uiso R . . . . . H431 H -0.0727 0.2561 0.2636 0.057(6) 1.0000 Uiso R . . . . . H441 H -0.1813 0.2528 0.3293 0.077(7) 1.0000 Uiso R . . . . . H451 H -0.1482 0.1931 0.4548 0.079(7) 1.0000 Uiso R . . . . . H461 H -0.0105 0.1271 0.5119 0.107(9) 1.0000 Uiso R . . . . . H471 H 0.0982 0.1276 0.4459 0.078(7) 1.0000 Uiso 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 S1 0.0641(3) 0.0469(3) 0.0654(3) 0.0083(2) 0.0362(2) 0.0028(2) S2 0.0481(2) 0.0460(2) 0.0554(3) -0.0027(2) 0.0176(2) 0.0066(2) P1 0.03200(19) 0.02959(19) 0.02797(18) -0.00122(14) 0.00908(14) 0.00052(15) P2 0.03213(19) 0.03171(19) 0.02740(18) 0.00002(15) 0.00843(14) 0.00099(15) N1 0.0500(9) 0.0526(9) 0.0529(9) -0.0069(7) 0.0152(7) 0.0024(7) N2 0.0571(10) 0.0548(10) 0.0553(9) 0.0051(7) 0.0251(8) 0.0029(7) N3 0.0542(9) 0.0328(7) 0.0584(9) -0.0014(6) 0.0316(7) -0.0002(6) N4 0.0372(7) 0.0370(7) 0.0354(7) -0.0009(5) 0.0054(5) 0.0013(6) C1 0.0497(10) 0.0373(9) 0.0396(8) -0.0017(7) 0.0214(7) 0.0011(7) C2 0.0539(11) 0.0453(10) 0.0525(10) -0.0078(8) 0.0207(9) -0.0036(8) C3 0.0820(15) 0.0413(10) 0.0588(11) -0.0109(9) 0.0350(11) -0.0034(10) C4 0.0839(16) 0.0489(12) 0.0668(13) 0.0028(10) 0.0365(12) 0.0226(11) C5 0.0549(12) 0.0692(14) 0.0628(12) -0.0002(10) 0.0176(10) 0.0153(10) C6 0.0445(9) 0.0361(9) 0.0575(11) 0.0005(7) 0.0252(8) 0.0028(7) C7 0.0643(12) 0.0432(10) 0.0720(14) -0.0072(9) 0.0325(10) -0.0034(9) C8 0.0762(15) 0.0370(11) 0.119(2) -0.0031(12) 0.0481(15) -0.0053(10) C9 0.0791(16) 0.0521(13) 0.116(2) 0.0313(13) 0.0587(15) 0.0122(11) C10 0.0734(14) 0.0684(15) 0.0720(15) 0.0241(12) 0.0379(12) 0.0166(12) C11 0.0397(9) 0.0388(9) 0.0433(9) -0.0094(7) 0.0155(7) -0.0051(7) C12 0.0398(8) 0.0319(8) 0.0348(8) -0.0020(6) 0.0117(6) 0.0024(6) C13 0.0882(15) 0.0375(10) 0.0723(13) -0.0036(9) 0.0534(12) -0.0002(10) C14 0.1048(18) 0.0501(12) 0.0747(14) -0.0044(10) 0.0595(14) 0.0102(12) C15 0.0720(13) 0.0354(9) 0.0529(10) -0.0068(8) 0.0194(10) 0.0122(9) C16 0.0832(14) 0.0308(9) 0.0706(13) 0.0017(8) 0.0337(11) 0.0026(9) C17 0.0697(12) 0.0359(9) 0.0567(11) -0.0001(8) 0.0338(10) 0.0013(8) C18 0.0395(8) 0.0329(8) 0.0423(8) -0.0022(6) 0.0186(7) -0.0011(6) C19 0.0599(12) 0.0623(12) 0.0472(10) 0.0075(9) 0.0266(9) 0.0066(9) C20 0.0929(18) 0.0770(16) 0.0732(15) 0.0157(12) 0.0581(14) 0.0114(13) C21 0.0769(16) 0.0671(15) 0.116(2) 0.0065(14) 0.0695(16) -0.0047(12) C22 0.0467(12) 0.0959(19) 0.115(2) -0.0184(16) 0.0365(14) -0.0193(12) C23 0.0442(10) 0.0790(14) 0.0612(12) -0.0162(11) 0.0193(9) -0.0131(10) C24 0.0367(8) 0.0367(8) 0.0312(7) 0.0025(6) 0.0114(6) 0.0047(6) C25 0.0564(10) 0.0377(9) 0.0376(8) 0.0009(7) 0.0152(8) 0.0011(8) C26 0.0917(15) 0.0396(10) 0.0533(11) 0.0084(8) 0.0304(11) 0.0051(10) C27 0.0991(17) 0.0569(13) 0.0460(11) 0.0204(9) 0.0253(11) 0.0254(12) C28 0.0735(14) 0.0746(15) 0.0351(9) 0.0078(9) 0.0020(9) 0.0152(11) C29 0.0537(10) 0.0518(11) 0.0379(9) -0.0002(8) 0.0042(8) -0.0003(8) C30 0.0353(8) 0.0328(8) 0.0355(8) 0.0017(6) 0.0082(6) 0.0008(6) C31 0.0756(13) 0.0413(10) 0.0428(9) -0.0015(8) 0.0263(9) -0.0047(9) C32 0.0860(15) 0.0514(11) 0.0451(10) 0.0051(8) 0.0255(10) -0.0137(10) C33 0.0663(13) 0.0403(10) 0.0719(13) 0.0149(9) 0.0185(11) -0.0040(9) C34 0.0835(15) 0.0356(10) 0.1007(17) 0.0035(10) 0.0491(14) 0.0088(10) C35 0.0657(12) 0.0384(9) 0.0709(13) 0.0008(9) 0.0396(10) 0.0063(9) C36 0.0337(8) 0.0355(8) 0.0299(7) -0.0015(6) 0.0112(6) -0.0040(6) C37 0.0390(9) 0.0466(10) 0.0355(8) -0.0009(7) 0.0083(7) 0.0012(7) C38 0.0481(10) 0.0662(13) 0.0348(9) -0.0087(8) 0.0071(8) -0.0086(9) C39 0.0645(12) 0.0509(11) 0.0415(9) -0.0169(8) 0.0227(9) -0.0191(9) C40 0.0607(11) 0.0351(9) 0.0530(10) -0.0041(7) 0.0272(9) -0.0028(8) C41 0.0445(9) 0.0367(8) 0.0382(8) 0.0006(7) 0.0132(7) -0.0013(7) C42 0.0383(8) 0.0409(9) 0.0339(8) -0.0013(6) 0.0138(6) -0.0009(7) C43 0.0460(10) 0.0512(11) 0.0578(11) 0.0112(9) 0.0204(8) 0.0082(8) C44 0.0466(11) 0.0572(12) 0.0887(16) 0.0044(11) 0.0335(11) 0.0077(9) C45 0.0591(13) 0.0784(15) 0.0710(14) -0.0139(12) 0.0421(11) -0.0111(11) C46 0.0671(14) 0.118(2) 0.0441(11) 0.0105(12) 0.0278(10) -0.0091(14) C47 0.0463(10) 0.0899(15) 0.0407(9) 0.0128(10) 0.0148(8) 0.0018(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . C11 . 1.6878(18) yes S2 . C11 . 1.6891(17) yes P1 . N4 . 1.5710(13) yes P1 . C12 . 1.8028(15) yes P1 . C18 . 1.8011(16) yes P1 . C24 . 1.8000(15) yes P2 . N4 . 1.5770(13) yes P2 . C30 . 1.8041(15) yes P2 . C36 . 1.8012(15) yes P2 . C42 . 1.8005(16) yes N1 . C1 . 1.324(2) yes N1 . C5 . 1.344(3) yes N2 . C6 . 1.324(2) yes N2 . C10 . 1.342(3) yes N3 . C1 . 1.426(2) yes N3 . C6 . 1.426(2) yes N3 . C11 . 1.401(2) yes C1 . C2 . 1.386(2) yes C2 . C3 . 1.371(3) yes C2 . H21 . 0.949 no C3 . C4 . 1.374(3) yes C3 . H31 . 0.949 no C4 . C5 . 1.364(3) yes C4 . H41 . 0.949 no C5 . H51 . 0.949 no C6 . C7 . 1.380(3) yes C7 . C8 . 1.378(3) yes C7 . H71 . 0.949 no C8 . C9 . 1.371(4) yes C8 . H81 . 0.949 no C9 . C10 . 1.361(4) yes C9 . H91 . 0.949 no C10 . H101 . 0.949 no C12 . C13 . 1.381(2) yes C12 . C17 . 1.376(2) yes C13 . C14 . 1.384(3) yes C13 . H131 . 0.949 no C14 . C15 . 1.364(3) yes C14 . H141 . 0.949 no C15 . C16 . 1.366(3) yes C15 . H151 . 0.949 no C16 . C17 . 1.386(2) yes C16 . H161 . 0.949 no C17 . H171 . 0.949 no C18 . C19 . 1.382(2) yes C18 . C23 . 1.382(2) yes C19 . C20 . 1.385(3) yes C19 . H191 . 0.949 no C20 . C21 . 1.369(4) yes C20 . H201 . 0.949 no C21 . C22 . 1.363(4) yes C21 . H211 . 0.949 no C22 . C23 . 1.382(3) yes C22 . H221 . 0.949 no C23 . H231 . 0.949 no C24 . C25 . 1.383(2) yes C24 . C29 . 1.392(2) yes C25 . C26 . 1.385(2) yes C25 . H251 . 0.949 no C26 . C27 . 1.369(3) yes C26 . H261 . 0.949 no C27 . C28 . 1.372(3) yes C27 . H271 . 0.949 no C28 . C29 . 1.380(3) yes C28 . H281 . 0.949 no C29 . H291 . 0.949 no C30 . C31 . 1.386(2) yes C30 . C35 . 1.381(2) yes C31 . C32 . 1.380(3) yes C31 . H311 . 0.949 no C32 . C33 . 1.371(3) yes C32 . H321 . 0.949 no C33 . C34 . 1.376(3) yes C33 . H331 . 0.949 no C34 . C35 . 1.380(3) yes C34 . H341 . 0.949 no C35 . H351 . 0.949 no C36 . C37 . 1.393(2) yes C36 . C41 . 1.387(2) yes C37 . C38 . 1.383(2) yes C37 . H371 . 0.949 no C38 . C39 . 1.378(3) yes C38 . H381 . 0.949 no C39 . C40 . 1.376(3) yes C39 . H391 . 0.949 no C40 . C41 . 1.387(2) yes C40 . H401 . 0.949 no C41 . H411 . 0.949 no C42 . C43 . 1.384(2) yes C42 . C47 . 1.389(2) yes C43 . C44 . 1.384(3) yes C43 . H431 . 0.949 no C44 . C45 . 1.372(3) yes C44 . H441 . 0.949 no C45 . C46 . 1.372(3) yes C45 . H451 . 0.949 no C46 . C47 . 1.385(3) yes C46 . H461 . 0.949 no C47 . H471 . 0.949 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N4 . P1 . C12 . 115.42(7) yes N4 . P1 . C18 . 109.65(7) yes C12 . P1 . C18 . 107.62(7) yes N4 . P1 . C24 . 108.30(7) yes C12 . P1 . C24 . 106.50(7) yes C18 . P1 . C24 . 109.18(7) yes N4 . P2 . C30 . 114.20(7) yes N4 . P2 . C36 . 106.99(7) yes C30 . P2 . C36 . 106.93(7) yes N4 . P2 . C42 . 110.97(7) yes C30 . P2 . C42 . 109.31(7) yes C36 . P2 . C42 . 108.18(7) yes C1 . N1 . C5 . 116.32(17) yes C6 . N2 . C10 . 116.76(18) yes C1 . N3 . C6 . 116.48(13) yes C1 . N3 . C11 . 121.83(14) yes C6 . N3 . C11 . 121.62(14) yes P2 . N4 . P1 . 142.31(9) yes N3 . C1 . N1 . 116.20(15) yes N3 . C1 . C2 . 120.35(16) yes N1 . C1 . C2 . 123.39(16) yes C1 . C2 . C3 . 118.67(18) yes C1 . C2 . H21 . 120.1 no C3 . C2 . H21 . 121.2 no C2 . C3 . C4 . 118.87(19) yes C2 . C3 . H31 . 120.6 no C4 . C3 . H31 . 120.5 no C3 . C4 . C5 . 118.39(19) yes C3 . C4 . H41 . 120.9 no C5 . C4 . H41 . 120.7 no C4 . C5 . N1 . 124.2(2) yes C4 . C5 . H51 . 118.4 no N1 . C5 . H51 . 117.4 no N3 . C6 . N2 . 116.04(16) yes N3 . C6 . C7 . 120.13(17) yes N2 . C6 . C7 . 123.79(17) yes C6 . C7 . C8 . 117.8(2) yes C6 . C7 . H71 . 120.5 no C8 . C7 . H71 . 121.7 no C7 . C8 . C9 . 119.2(2) yes C7 . C8 . H81 . 120.6 no C9 . C8 . H81 . 120.2 no C8 . C9 . C10 . 118.7(2) yes C8 . C9 . H91 . 121.0 no C10 . C9 . H91 . 120.3 no C9 . C10 . N2 . 123.6(2) yes C9 . C10 . H101 . 118.8 no N2 . C10 . H101 . 117.7 no N3 . C11 . S2 . 118.13(13) yes N3 . C11 . S1 . 117.54(12) yes S2 . C11 . S1 . 124.32(10) yes P1 . C12 . C13 . 119.20(13) yes P1 . C12 . C17 . 121.74(12) yes C13 . C12 . C17 . 118.90(15) yes C12 . C13 . C14 . 120.14(18) yes C12 . C13 . H131 . 119.6 no C14 . C13 . H131 . 120.2 no C13 . C14 . C15 . 120.49(18) yes C13 . C14 . H141 . 119.9 no C15 . C14 . H141 . 119.6 no C14 . C15 . C16 . 119.82(17) yes C14 . C15 . H151 . 120.2 no C16 . C15 . H151 . 120.0 no C15 . C16 . C17 . 120.19(18) yes C15 . C16 . H161 . 120.0 no C17 . C16 . H161 . 119.8 no C16 . C17 . C12 . 120.46(17) yes C16 . C17 . H171 . 120.2 no C12 . C17 . H171 . 119.4 no P1 . C18 . C19 . 119.05(13) yes P1 . C18 . C23 . 121.75(13) yes C19 . C18 . C23 . 119.19(17) yes C18 . C19 . C20 . 119.9(2) yes C18 . C19 . H191 . 119.4 no C20 . C19 . H191 . 120.7 no C19 . C20 . C21 . 120.5(2) yes C19 . C20 . H201 . 119.7 no C21 . C20 . H201 . 119.8 no C20 . C21 . C22 . 119.7(2) yes C20 . C21 . H211 . 120.3 no C22 . C21 . H211 . 120.0 no C21 . C22 . C23 . 120.7(2) yes C21 . C22 . H221 . 119.7 no C23 . C22 . H221 . 119.7 no C18 . C23 . C22 . 120.0(2) yes C18 . C23 . H231 . 119.3 no C22 . C23 . H231 . 120.7 no P1 . C24 . C25 . 119.29(12) yes P1 . C24 . C29 . 121.16(13) yes C25 . C24 . C29 . 119.56(15) yes C24 . C25 . C26 . 120.09(17) yes C24 . C25 . H251 . 119.7 no C26 . C25 . H251 . 120.2 no C25 . C26 . C27 . 119.91(19) yes C25 . C26 . H261 . 120.1 no C27 . C26 . H261 . 120.0 no C26 . C27 . C28 . 120.53(18) yes C26 . C27 . H271 . 120.0 no C28 . C27 . H271 . 119.5 no C27 . C28 . C29 . 120.30(19) yes C27 . C28 . H281 . 120.1 no C29 . C28 . H281 . 119.6 no C24 . C29 . C28 . 119.61(18) yes C24 . C29 . H291 . 119.8 no C28 . C29 . H291 . 120.6 no P2 . C30 . C31 . 119.59(12) yes P2 . C30 . C35 . 121.05(13) yes C31 . C30 . C35 . 119.05(16) yes C30 . C31 . C32 . 120.34(17) yes C30 . C31 . H311 . 119.5 no C32 . C31 . H311 . 120.2 no C31 . C32 . C33 . 120.23(18) yes C31 . C32 . H321 . 119.7 no C33 . C32 . H321 . 120.1 no C32 . C33 . C34 . 119.75(18) yes C32 . C33 . H331 . 120.1 no C34 . C33 . H331 . 120.2 no C33 . C34 . C35 . 120.38(19) yes C33 . C34 . H341 . 119.9 no C35 . C34 . H341 . 119.7 no C30 . C35 . C34 . 120.21(18) yes C30 . C35 . H351 . 119.5 no C34 . C35 . H351 . 120.2 no P2 . C36 . C37 . 120.43(12) yes P2 . C36 . C41 . 119.05(12) yes C37 . C36 . C41 . 120.42(14) yes C36 . C37 . C38 . 119.15(16) yes C36 . C37 . H371 . 120.2 no C38 . C37 . H371 . 120.6 no C37 . C38 . C39 . 120.43(17) yes C37 . C38 . H381 . 119.9 no C39 . C38 . H381 . 119.7 no C38 . C39 . C40 . 120.44(16) yes C38 . C39 . H391 . 119.7 no C40 . C39 . H391 . 119.9 no C39 . C40 . C41 . 120.01(17) yes C39 . C40 . H401 . 119.9 no C41 . C40 . H401 . 120.0 no C40 . C41 . C36 . 119.55(16) yes C40 . C41 . H411 . 120.5 no C36 . C41 . H411 . 120.0 no P2 . C42 . C43 . 121.67(13) yes P2 . C42 . C47 . 118.91(13) yes C43 . C42 . C47 . 119.35(16) yes C42 . C43 . C44 . 120.00(18) yes C42 . C43 . H431 . 119.6 no C44 . C43 . H431 . 120.4 no C43 . C44 . C45 . 120.37(19) yes C43 . C44 . H441 . 119.9 no C45 . C44 . H441 . 119.7 no C44 . C45 . C46 . 119.99(18) yes C44 . C45 . H451 . 119.9 no C46 . C45 . H451 . 120.1 no C45 . C46 . C47 . 120.3(2) yes C45 . C46 . H461 . 119.8 no C47 . C46 . H461 . 119.9 no C42 . C47 . C46 . 119.88(19) yes C42 . C47 . H471 . 119.5 no C46 . C47 . H471 . 120.6 no _database_code_depnum_ccdc_archive 'CCDC 961601' ####################################################################### # # 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_[Au(dopdtc)]2 #=============================================================================== # 5. CHEMICAL DATA _chemical_formula_sum 'C22 H16 Au2 N6 S4' _chemical_formula_moiety 'C22 H16 Au2 N6 S4' _chemical_formula_weight 886.63 #============================================================= # 6. CRYSTAL DATA _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 9.89190(10) _cell_length_b 10.6931(2) _cell_length_c 12.77110(10) _cell_angle_alpha 81.1430(10) _cell_angle_beta 77.83 _cell_angle_gamma 74.36 _cell_volume 1264.83(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9907 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 28.51 _cell_measurement_temperature 293 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_min 0.060 _exptl_crystal_size_mid 0.116 _exptl_crystal_size_max 0.308 _exptl_crystal_density_diffrn 2.328 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 11.940 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.207 _exptl_absorpt_correction_T_max 0.489 #============================================================================= # 7. EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_method \w/2\q _diffrn_ambient_temperature 293 _diffrn_reflns_number 21089 _diffrn_reflns_av_R_equivalents 0.037 _diffrn_reflns_theta_min 1.640 _diffrn_reflns_theta_max 28.554 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.554 _diffrn_measured_fraction_theta_full 0.995 _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 -16 _diffrn_reflns_limit_l_max 17 #========================================================================== # 8. REFINEMENT DATA # The values actually used during refinement # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _oxford_reflns_threshold_expression_ref I>2.5\s(I) _refine_ls_number_reflns 4837 _refine_ls_number_restraints 0 _refine_ls_number_parameters 323 _oxford_refine_ls_R_factor_ref 0.0255 _refine_ls_wR_factor_ref 0.0220 _refine_ls_goodness_of_fit_ref 1.1245 # The values computed from all data _oxford_reflns_number_all 6457 _refine_ls_R_factor_all 0.0390 _refine_ls_wR_factor_all 0.0370 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4944 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_gt 0.0223 _reflns_number_total 6457 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.184 0.136 0.116 0.744E-01 0.317E-01 ; _refine_ls_shift/su_max 0.0013114 _refine_diff_density_min -0.83 _refine_diff_density_max 0.60 _reflns_limit_h_min -12 _reflns_limit_h_max 13 _reflns_limit_k_min -14 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_refine_ls_scale 0.08589(6) _oxford_diffrn_Wilson_B_factor 2.87 _oxford_diffrn_Wilson_scale 144.07 # Number of reflections without Friedels Law is 7762 # Number of reflections with Friedels Law is 4303 # Theoretical number of reflections is about 3910 #--------------------------------------------------------- _chemical_name_systematic ; ; # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary Other # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment constr # none if no extinction, _refine_ls_extinction_method None # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . #========================================================== # 9. General computing _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_cell_refinement 'Bruker SAINT' _computing_structure_solution ; SIR92 (Altomare et al, 1994) CRYSTALS (Watkin, 1988) ; #=================================================================== # 10. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Au -2.0133 8.8022 16.8819 0.4611 18.5913 8.6216 25.5582 1.4826 5.8600 36.3956 12.0658 'International Tables Vol C 4.2.6.8 and 6.1.1.4' #============================================================================== # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom # TODO check _oxford_atom_site_special_shape 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Au1 Au 0.352717(19) 0.52122(2) 0.534567(16) 0.0373 1.0000 Uani . . . . . . Au2 Au 0.035576(19) 0.59195(2) 0.550434(15) 0.0363 1.0000 Uani . . . . . . S1 S 0.65673(14) 0.65014(16) 0.54814(16) 0.0628 1.0000 Uani . . . . . . S2 S 0.33124(15) 0.69831(18) 0.62226(15) 0.0648 1.0000 Uani . . . . . . S3 S -0.02517(17) 0.49625(17) 0.72023(11) 0.0559 1.0000 Uani . . . . . . S4 S -0.09301(15) 0.28944(13) 0.61002(10) 0.0443 1.0000 Uani . . . . . . N1 N 0.6796(6) 0.8105(5) 0.7632(5) 0.0680 1.0000 Uani . . . . . . N2 N 0.4968(4) 0.8230(4) 0.6713(3) 0.0399 1.0000 Uani . . . . . . C7 C 0.3058(6) 0.8615(6) 0.8283(5) 0.0510 1.0000 Uani . . . . . . N4 N -0.1137(6) 0.3497(5) 0.9639(4) 0.0570 1.0000 Uani . . . . . . N5 N -0.2003(4) 0.3517(4) 0.8054(3) 0.0387 1.0000 Uani . . . . . . N6 N -0.2889(6) 0.1742(5) 0.8874(4) 0.0556 1.0000 Uani . . . . . . C1 C 0.6280(5) 0.8569(5) 0.6753(5) 0.0450 1.0000 Uani . . . . . . C2 C 0.6854(7) 0.9355(7) 0.5930(6) 0.0633 1.0000 Uani . . . . . . C3 C 0.8076(8) 0.9665(9) 0.6008(8) 0.0918 1.0000 Uani . . . . . . C4 C 0.8668(9) 0.9186(10) 0.6884(10) 0.0969 1.0000 Uani . . . . . . C5 C 0.8018(9) 0.8421(9) 0.7668(9) 0.0920 1.0000 Uani . . . . . . C6 C 0.3679(5) 0.9035(5) 0.7280(4) 0.0408 1.0000 Uani . . . . . . N3 N 0.3256(5) 1.0206(5) 0.6760(4) 0.0496 1.0000 Uani . . . . . . C10 C 0.2101(7) 1.1004(7) 0.7267(6) 0.0625 1.0000 Uani . . . . . . C9 C 0.1383(7) 1.0665(7) 0.8273(6) 0.0619 1.0000 Uani . . . . . . C8 C 0.1869(7) 0.9464(7) 0.8783(5) 0.0630 1.0000 Uani . . . . . . C11 C 0.4956(5) 0.7277(5) 0.6162(4) 0.0370 1.0000 Uani . . . . . . C12 C -0.2094(5) 0.4095(5) 0.9033(4) 0.0403 1.0000 Uani . . . . . . C13 C -0.3160(7) 0.5180(7) 0.9257(6) 0.0629 1.0000 Uani . . . . . . C14 C -0.3233(8) 0.5706(8) 1.0194(6) 0.0848 1.0000 Uani . . . . . . C15 C -0.2265(9) 0.5121(9) 1.0839(6) 0.0786 1.0000 Uani . . . . . . C16 C -0.1246(8) 0.4028(8) 1.0539(6) 0.0714 1.0000 Uani . . . . . . C17 C -0.2992(5) 0.2724(5) 0.8118(4) 0.0398 1.0000 Uani . . . . . . C18 C -0.4002(6) 0.3056(6) 0.7464(5) 0.0512 1.0000 Uani . . . . . . C19 C -0.4952(6) 0.2286(7) 0.7590(5) 0.0555 1.0000 Uani . . . . . . C20 C -0.4876(7) 0.1264(6) 0.8364(5) 0.0603 1.0000 Uani . . . . . . C21 C -0.3874(8) 0.1036(7) 0.8976(5) 0.0697 1.0000 Uani . . . . . . C22 C -0.1136(5) 0.3816(5) 0.7142(4) 0.0358 1.0000 Uani . . . . . . H21 H 0.6407 0.9677 0.5339 0.059(19) 1.0000 Uiso R . . . . . H31 H 0.8494 1.0195 0.5466 0.15(4) 1.0000 Uiso R . . . . . H41 H 0.9510 0.9371 0.6950 0.09(2) 1.0000 Uiso R . . . . . H51 H 0.8433 0.8091 0.8274 0.14(4) 1.0000 Uiso R . . . . . H101 H 0.1779 1.1834 0.6911 0.050(16) 1.0000 Uiso R . . . . . H91 H 0.0572 1.1250 0.8591 0.07(2) 1.0000 Uiso R . . . . . H81 H 0.1402 0.9222 0.9467 0.07(2) 1.0000 Uiso R . . . . . H131 H -0.3804 0.5553 0.8788 0.09(2) 1.0000 Uiso R . . . . . H141 H -0.3934 0.6461 1.0380 0.08(2) 1.0000 Uiso R . . . . . H151 H -0.2300 0.5461 1.1475 0.10(3) 1.0000 Uiso R . . . . . H161 H -0.0585 0.3629 1.0986 0.08(2) 1.0000 Uiso R . . . . . H181 H -0.4038 0.3785 0.6961 0.07(2) 1.0000 Uiso R . . . . . H191 H -0.5637 0.2476 0.7149 0.07(2) 1.0000 Uiso R . . . . . H201 H -0.5513 0.0731 0.8475 0.08(2) 1.0000 Uiso R . . . . . H211 H -0.3838 0.0342 0.9516 0.056(17) 1.0000 Uiso R . . . . . H71 H 0.3435 0.7776 0.8624 0.11(3) 1.0000 Uiso 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 0.02644(9) 0.04312(12) 0.04538(13) -0.01473(9) -0.00450(8) -0.00931(8) Au2 0.03053(10) 0.04899(12) 0.03333(10) -0.00997(9) -0.00110(7) -0.01666(8) S1 0.0302(6) 0.0616(10) 0.1051(13) -0.0490(9) -0.0019(7) -0.0109(6) S2 0.0310(7) 0.0819(11) 0.0931(12) -0.0575(10) 0.0023(7) -0.0165(7) S3 0.0673(9) 0.0840(11) 0.0336(7) -0.0060(7) -0.0035(6) -0.0516(9) S4 0.0550(8) 0.0424(7) 0.0353(7) -0.0072(5) -0.0028(6) -0.0140(6) N1 0.063(3) 0.056(3) 0.096(4) -0.011(3) -0.040(3) -0.011(3) N2 0.037(2) 0.041(2) 0.046(2) -0.0130(19) -0.0078(18) -0.0128(18) C7 0.053(3) 0.046(3) 0.050(3) -0.004(3) -0.007(3) -0.009(3) N4 0.064(3) 0.067(3) 0.043(3) -0.007(2) -0.021(2) -0.013(3) N5 0.043(2) 0.047(2) 0.029(2) -0.0067(18) 0.0001(17) -0.0188(19) N6 0.070(3) 0.057(3) 0.047(3) 0.005(2) -0.013(2) -0.031(3) C1 0.034(3) 0.043(3) 0.064(4) -0.020(3) -0.009(2) -0.011(2) C2 0.061(4) 0.075(5) 0.063(4) -0.022(4) 0.003(3) -0.033(3) C3 0.067(5) 0.108(7) 0.117(7) -0.048(6) 0.019(5) -0.056(5) C4 0.056(4) 0.101(7) 0.158(9) -0.061(7) -0.025(5) -0.028(5) C5 0.075(5) 0.079(6) 0.141(8) -0.029(6) -0.064(6) -0.006(4) C6 0.038(3) 0.045(3) 0.045(3) -0.017(2) -0.008(2) -0.011(2) N3 0.039(2) 0.054(3) 0.051(3) -0.008(2) -0.007(2) -0.005(2) C10 0.051(3) 0.058(4) 0.073(5) -0.005(3) -0.021(3) 0.003(3) C9 0.046(3) 0.065(4) 0.068(4) -0.028(3) -0.006(3) 0.006(3) C8 0.056(4) 0.075(5) 0.054(4) -0.014(3) 0.005(3) -0.016(3) C11 0.030(2) 0.040(3) 0.043(3) -0.009(2) -0.010(2) -0.007(2) C12 0.044(3) 0.049(3) 0.033(3) -0.003(2) -0.003(2) -0.022(2) C13 0.051(3) 0.069(4) 0.070(4) -0.028(4) -0.014(3) -0.003(3) C14 0.072(5) 0.095(6) 0.089(6) -0.058(5) 0.002(4) -0.009(5) C15 0.088(5) 0.108(6) 0.054(4) -0.040(4) -0.005(4) -0.036(5) C16 0.082(5) 0.092(5) 0.051(4) -0.012(4) -0.025(4) -0.027(4) C17 0.044(3) 0.044(3) 0.035(3) -0.007(2) 0.002(2) -0.021(2) C18 0.048(3) 0.062(4) 0.046(3) 0.003(3) -0.010(2) -0.021(3) C19 0.052(3) 0.079(4) 0.044(3) -0.012(3) -0.005(3) -0.031(3) C20 0.075(4) 0.067(4) 0.054(4) -0.013(3) -0.002(3) -0.047(4) C21 0.104(6) 0.063(4) 0.055(4) 0.014(3) -0.014(4) -0.053(4) C22 0.030(2) 0.044(3) 0.033(2) -0.005(2) -0.0020(18) -0.011(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Au1 . Au1 2_666 2.7932(4) yes Au1 . S1 2_666 2.2829(14) yes Au1 . Au2 . 2.9925(3) yes Au1 . S2 . 2.2849(14) yes Au2 . Au2 2_566 2.8161(4) yes Au2 . S4 2_566 2.2864(13) yes Au2 . S3 . 2.2824(14) yes S1 . C11 . 1.706(5) yes S2 . C11 . 1.721(5) yes S3 . C22 . 1.706(5) yes S4 . C22 . 1.722(5) yes N1 . C1 . 1.304(8) yes N1 . C5 . 1.351(9) yes N2 . C1 . 1.451(6) yes N2 . C6 . 1.450(6) yes N2 . C11 . 1.328(6) yes C7 . C6 . 1.364(8) yes C7 . C8 . 1.379(8) yes C7 . H71 . 0.950 no N4 . C12 . 1.317(7) yes N4 . C16 . 1.330(8) yes N5 . C12 . 1.454(6) yes N5 . C17 . 1.442(6) yes N5 . C22 . 1.343(6) yes N6 . C17 . 1.311(7) yes N6 . C21 . 1.360(8) yes C1 . C2 . 1.367(9) yes C2 . C3 . 1.364(9) yes C2 . H21 . 0.929 no C3 . C4 . 1.340(13) yes C3 . H31 . 0.926 no C4 . C5 . 1.358(13) yes C4 . H41 . 0.929 no C5 . H51 . 0.930 no C6 . N3 . 1.328(7) yes N3 . C10 . 1.336(8) yes C10 . C9 . 1.377(9) yes C10 . H101 . 0.939 no C9 . C8 . 1.359(9) yes C9 . H91 . 0.932 no C8 . H81 . 0.932 no C12 . C13 . 1.362(8) yes C13 . C14 . 1.379(9) yes C13 . H131 . 0.935 no C14 . C15 . 1.356(11) yes C14 . H141 . 0.937 no C15 . C16 . 1.367(11) yes C15 . H151 . 0.931 no C16 . H161 . 0.931 no C17 . C18 . 1.375(7) yes C18 . C19 . 1.378(8) yes C18 . H181 . 0.929 no C19 . C20 . 1.354(9) yes C19 . H191 . 0.932 no C20 . C21 . 1.338(9) yes C20 . H201 . 0.935 no C21 . H211 . 0.931 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Au1 2_666 Au1 . S1 2_666 92.20(4) yes Au1 2_666 Au1 . Au2 . 165.552(12) yes S1 2_666 Au1 . Au2 . 83.80(3) yes Au1 2_666 Au1 . S2 . 95.05(3) yes S1 2_666 Au1 . S2 . 172.71(5) yes Au2 . Au1 . S2 . 88.99(4) yes Au1 . Au2 . Au2 2_566 107.894(10) yes Au1 . Au2 . S4 2_566 81.48(4) yes Au2 2_566 Au2 . S4 2_566 92.46(3) yes Au1 . Au2 . S3 . 98.88(4) yes Au2 2_566 Au2 . S3 . 94.09(4) yes S4 2_566 Au2 . S3 . 172.98(5) yes Au1 2_666 S1 . C11 . 113.71(17) yes Au1 . S2 . C11 . 110.78(17) yes Au2 . S3 . C22 . 108.99(17) yes Au2 2_566 S4 . C22 . 109.53(17) yes C1 . N1 . C5 . 114.5(7) yes C1 . N2 . C6 . 115.2(4) yes C1 . N2 . C11 . 121.9(4) yes C6 . N2 . C11 . 122.8(4) yes C6 . C7 . C8 . 117.2(6) yes C6 . C7 . H71 . 121.3 no C8 . C7 . H71 . 121.5 no C12 . N4 . C16 . 115.5(6) yes C12 . N5 . C17 . 115.2(4) yes C12 . N5 . C22 . 120.9(4) yes C17 . N5 . C22 . 123.7(4) yes C17 . N6 . C21 . 114.7(5) yes N2 . C1 . N1 . 114.6(5) yes N2 . C1 . C2 . 120.4(5) yes N1 . C1 . C2 . 125.0(5) yes C1 . C2 . C3 . 118.4(8) yes C1 . C2 . H21 . 120.2 no C3 . C2 . H21 . 121.3 no C2 . C3 . C4 . 118.9(9) yes C2 . C3 . H31 . 120.7 no C4 . C3 . H31 . 120.4 no C3 . C4 . C5 . 118.7(7) yes C3 . C4 . H41 . 120.4 no C5 . C4 . H41 . 120.8 no C4 . C5 . N1 . 124.4(8) yes C4 . C5 . H51 . 118.3 no N1 . C5 . H51 . 117.2 no N2 . C6 . C7 . 121.0(5) yes N2 . C6 . N3 . 113.6(5) yes C7 . C6 . N3 . 125.3(5) yes C6 . N3 . C10 . 115.9(5) yes N3 . C10 . C9 . 123.3(6) yes N3 . C10 . H101 . 117.3 no C9 . C10 . H101 . 119.5 no C10 . C9 . C8 . 118.8(6) yes C10 . C9 . H91 . 120.2 no C8 . C9 . H91 . 121.0 no C7 . C8 . C9 . 119.5(6) yes C7 . C8 . H81 . 120.5 no C9 . C8 . H81 . 120.0 no S2 . C11 . S1 . 128.1(3) yes S2 . C11 . N2 . 115.9(4) yes S1 . C11 . N2 . 116.0(3) yes N5 . C12 . N4 . 116.2(5) yes N5 . C12 . C13 . 118.1(5) yes N4 . C12 . C13 . 125.7(5) yes C12 . C13 . C14 . 117.1(6) yes C12 . C13 . H131 . 121.0 no C14 . C13 . H131 . 121.9 no C13 . C14 . C15 . 119.0(7) yes C13 . C14 . H141 . 120.7 no C15 . C14 . H141 . 120.3 no C14 . C15 . C16 . 118.9(6) yes C14 . C15 . H151 . 120.2 no C16 . C15 . H151 . 120.9 no C15 . C16 . N4 . 123.7(7) yes C15 . C16 . H161 . 118.6 no N4 . C16 . H161 . 117.7 no N5 . C17 . N6 . 114.6(5) yes N5 . C17 . C18 . 120.7(5) yes N6 . C17 . C18 . 124.6(5) yes C17 . C18 . C19 . 118.0(6) yes C17 . C18 . H181 . 120.2 no C19 . C18 . H181 . 121.8 no C18 . C19 . C20 . 118.9(6) yes C18 . C19 . H191 . 120.1 no C20 . C19 . H191 . 121.0 no C19 . C20 . C21 . 118.6(5) yes C19 . C20 . H201 . 120.9 no C21 . C20 . H201 . 120.5 no N6 . C21 . C20 . 125.1(6) yes N6 . C21 . H211 . 116.7 no C20 . C21 . H211 . 118.2 no S4 . C22 . S3 . 127.8(3) yes S4 . C22 . N5 . 116.2(4) yes S3 . C22 . N5 . 115.7(4) yes _database_code_depnum_ccdc_archive 'CCDC 961602'