metal-organic compounds
[μ-1,2-Bis(diphenylphosphino)methane-κ2P:P′]bis{[(Z)-O-ethyl N-(4-nitrophenyl)thiocarbamato-κS]gold(I)}
aDepartment of Chemistry, National University of Singapore, Singapore 117543, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com
Each gold atom in the binuclear title compound, [Au2(C9H9N2O3S)2(C25H22P2)], is coordinated within an S,P-donor set that defines a slightly distorted linear geometry [S—Au—P angles = 172.77 (6) and 173.84 (6)°], with the distortion due in part to a close intramolecular Au⋯O contact [2.968 (11) and 2.963 (4) Å]. The molecule adopts a U-shaped conformation allowing for the formation of an aurophilic Au⋯Au interaction [3.2320 (5) Å]. Molecules are consolidated in the by C—H⋯π interactions. Disorder was noted for one of the ethoxy groups with two orientations being resolved in a 0.679 (16):0.321 (16) ratio.
Related literature
For the structural systematics and luminescence properties of phosphinegold(I) carbonimidothioates, see: Ho et al. (2006); Ho & Tiekink (2007); Kuan et al. (2008). For the synthesis, see: Hall et al. (1993).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT ; program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
https://doi.org/10.1107/S1600536810016326/hb5435sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810016326/hb5435Isup2.hkl
Compound (I) was prepared following the standard literature procedure from the reaction of [Ph2PCH2PPh2](AuCl)2 and EtOC(═S)N(H)(C6H4NO2-4) in the presence of NaOH (Hall et al., 1993). Yellow blocks of (I) were obtained by the slow evaporation of a CHCl3/hexane (3/1) solution held at room temperature; m.pt. 483 K. Analysis, Found (Calculated): C 41.97 (42.03); H 3.67 (3.28); N 4.09 (4.56); S 4.64 (5.20). IR (KBr, cm-1): ν(C–S) 1103 (s), 851 (m); ν(C–N) 1580 (m); ν(C–O) 1144 (s). 31P{1H} (CDCl3) NMR: δ 29.2 p.p.m.
The H atoms were geometrically placed (C—H = 0.94–0.98 Å) and refined as riding with Uiso(H) = 1.2-1.5Ueq(C). The maximum and minimum residual electron density peaks of 1.52 and 1.19 e Å-3, respectively, were located 0.90 Å and 1.53 Å from the Au1 and Au2 atoms, respectively. High thermal motion was noted in the O1-ethoxy substituent but only two positions were resolved for each of three atoms. Anisotropic
(constrained to be equivalent for paired components of the disorder, and approximately isotropic by the EADP and ISOR commands in SHELXL-97 (Sheldrick, 2008), respectively) and with the O–C and C–C distances restrained to 1.45+0.01 and 1.48±0.01 Å showed the major component of the disorder had a site occupancy factor = 0.679 (16).The investigation of dinuclear molecules related to molecules with the general formula R3PAu[SC(OR')═ NR''], for R, R' and R'' = alkyl and aryl,have proved useful for crystal engineering studies, in particular in terms of a competition between intra- and inter-molecular aurophilic (Au···Au) interactions, and the influence of these upon luminescence (Ho et al., 2006; Ho & Tiekink, 2007; Kuan et al., 2008). The title compound, (I), is the ethoxy analogue of the previously reported methoxy derivative (Ho et al., 2006).
The nearly linear SP coordination geometry observed for each Au atom, Fig. 1, is defined by one P atom of the bidentate bridging diphosphine ligand and the thiolate-S derived from the carbonimidothioate anion, Table 1. Deviations from the ideal linearity [S—Au—P = 172.77 (6) and 173.84 (6) °] is traced to the close intramolecular Au···O contacts [2.968 (11) and 2.963 (4) Å]. Overall, the conformation of the dinuclear molecule is a U-shape which allows for the formation of an intramolecular Au···Au contact of 3.2320 (5) Å which is longer than 3.1589 (4) Å found in the methoxy derivative (Ho et al. 2006).
The major feature of the crystal packing is the presence of C–H···π interactions, Table 2 and Fig. 2.
For the structural systematics and luminescence properties of phosphinegold(I) carbonimidothioates, see: Ho et al. (2006); Ho & Tiekink (2007); Kuan et al. (2008). For the synthesis, see Hall et al. (1993).
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).[Au2(C9H9N2O3S)2(C25H22P2)] | F(000) = 4751 |
Mr = 1228.83 | Dx = 1.796 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -I 2ya | Cell parameters from 5597 reflections |
a = 24.400 (3) Å | θ = 2.5–24.2° |
b = 16.1419 (16) Å | µ = 6.66 mm−1 |
c = 24.594 (2) Å | T = 223 K |
β = 110.252 (9)° | Block, yellow |
V = 9087.9 (16) Å3 | 0.31 × 0.13 × 0.05 mm |
Z = 8 |
Bruker SMART CCD diffractometer | 10427 independent reflections |
Radiation source: fine-focus sealed tube | 7923 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
ω scans | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −27→31 |
Tmin = 0.445, Tmax = 1 | k = −20→20 |
31967 measured reflections | l = −31→24 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3 |
10427 reflections | (Δ/σ)max = 0.001 |
549 parameters | Δρmax = 1.52 e Å−3 |
28 restraints | Δρmin = −1.19 e Å−3 |
[Au2(C9H9N2O3S)2(C25H22P2)] | V = 9087.9 (16) Å3 |
Mr = 1228.83 | Z = 8 |
Monoclinic, I2/a | Mo Kα radiation |
a = 24.400 (3) Å | µ = 6.66 mm−1 |
b = 16.1419 (16) Å | T = 223 K |
c = 24.594 (2) Å | 0.31 × 0.13 × 0.05 mm |
β = 110.252 (9)° |
Bruker SMART CCD diffractometer | 10427 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 7923 reflections with I > 2σ(I) |
Tmin = 0.445, Tmax = 1 | Rint = 0.053 |
31967 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 28 restraints |
wR(F2) = 0.110 | H-atom parameters constrained |
S = 1.02 | Δρmax = 1.52 e Å−3 |
10427 reflections | Δρmin = −1.19 e Å−3 |
549 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Au1 | 1.009521 (10) | 0.859132 (13) | 0.324297 (11) | 0.03469 (8) | |
Au2 | 0.879170 (10) | 0.815714 (13) | 0.237856 (11) | 0.03270 (8) | |
S1 | 0.99717 (8) | 0.99888 (10) | 0.33639 (8) | 0.0448 (4) | |
S2 | 0.84758 (7) | 0.93438 (9) | 0.18429 (8) | 0.0408 (4) | |
P1 | 1.03352 (6) | 0.72491 (9) | 0.31943 (7) | 0.0290 (3) | |
P2 | 0.90430 (7) | 0.69252 (9) | 0.28151 (7) | 0.0288 (3) | |
O2 | 0.9091 (3) | 1.4064 (3) | 0.3450 (3) | 0.0745 (18) | |
O3 | 0.9791 (3) | 1.4426 (3) | 0.3166 (3) | 0.0731 (17) | |
O4 | 0.7826 (2) | 0.8134 (3) | 0.1245 (2) | 0.0553 (14) | |
O5 | 0.7025 (4) | 1.3205 (4) | 0.1153 (3) | 0.096 (3) | |
O6 | 0.7716 (4) | 1.3265 (4) | 0.0808 (4) | 0.111 (3) | |
N1 | 1.0713 (3) | 1.0927 (3) | 0.4211 (3) | 0.0595 (18) | |
N2 | 0.9560 (3) | 1.3930 (3) | 0.3388 (3) | 0.0514 (16) | |
N3 | 0.7433 (2) | 0.9417 (4) | 0.0988 (3) | 0.0548 (17) | |
N4 | 0.7390 (4) | 1.2877 (4) | 0.0992 (3) | 0.071 (2) | |
C1 | 1.0559 (3) | 1.0213 (4) | 0.4003 (3) | 0.0517 (19) | |
C2 | 1.0404 (3) | 1.1643 (4) | 0.3968 (3) | 0.0430 (17) | |
C3 | 0.9831 (3) | 1.1771 (4) | 0.3941 (3) | 0.0470 (17) | |
H3 | 0.9633 | 1.1343 | 0.4055 | 0.056* | |
C4 | 0.9546 (3) | 1.2513 (4) | 0.3751 (3) | 0.0421 (16) | |
H4 | 0.9160 | 1.2596 | 0.3735 | 0.051* | |
C5 | 0.9849 (3) | 1.3130 (3) | 0.3584 (3) | 0.0366 (14) | |
C6 | 1.0423 (3) | 1.3030 (4) | 0.3607 (3) | 0.0422 (16) | |
H6 | 1.0622 | 1.3460 | 0.3496 | 0.051* | |
C7 | 1.0689 (3) | 1.2284 (4) | 0.3796 (3) | 0.0458 (16) | |
H7 | 1.1075 | 1.2202 | 0.3810 | 0.055* | |
O1 | 1.0910 (5) | 0.9539 (9) | 0.4226 (5) | 0.053 (3) | 0.679 (16) |
C8 | 1.1390 (6) | 0.9687 (10) | 0.4772 (5) | 0.071 (4) | 0.679 (16) |
H8A | 1.1583 | 1.0211 | 0.4749 | 0.085* | 0.679 (16) |
H8B | 1.1679 | 0.9241 | 0.4840 | 0.085* | 0.679 (16) |
C9 | 1.1167 (9) | 0.9720 (13) | 0.5257 (9) | 0.129 (7) | 0.679 (16) |
H9A | 1.0805 | 1.0033 | 0.5140 | 0.194* | 0.679 (16) |
H9B | 1.1453 | 0.9986 | 0.5587 | 0.194* | 0.679 (16) |
H9C | 1.1094 | 0.9161 | 0.5361 | 0.194* | 0.679 (16) |
O1A | 1.0752 (12) | 0.955 (2) | 0.4357 (11) | 0.053 (3) | 0.321 (16) |
C8A | 1.1194 (13) | 0.962 (3) | 0.4932 (13) | 0.071 (4) | 0.321 (16) |
H8C | 1.1197 | 0.9118 | 0.5154 | 0.085* | 0.321 (16) |
H8D | 1.1104 | 1.0092 | 0.5139 | 0.085* | 0.321 (16) |
C9A | 1.1774 (18) | 0.974 (3) | 0.488 (2) | 0.129 (7) | 0.321 (16) |
H9D | 1.1897 | 0.9235 | 0.4746 | 0.194* | 0.321 (16) |
H9E | 1.2055 | 0.9895 | 0.5254 | 0.194* | 0.321 (16) |
H9F | 1.1751 | 1.0184 | 0.4603 | 0.194* | 0.321 (16) |
C10 | 0.7841 (3) | 0.8975 (4) | 0.1301 (3) | 0.0420 (16) | |
C11 | 0.7461 (3) | 1.0285 (4) | 0.1030 (3) | 0.0500 (19) | |
C12 | 0.7136 (3) | 1.0705 (4) | 0.1311 (3) | 0.0457 (17) | |
H12 | 0.6928 | 1.0406 | 0.1504 | 0.055* | |
C13 | 0.7120 (3) | 1.1557 (5) | 0.1307 (3) | 0.0523 (18) | |
H13 | 0.6905 | 1.1844 | 0.1499 | 0.063* | |
C14 | 0.7421 (3) | 1.1983 (4) | 0.1020 (3) | 0.0501 (19) | |
C15 | 0.7755 (4) | 1.1598 (5) | 0.0743 (4) | 0.064 (2) | |
H15 | 0.7970 | 1.1910 | 0.0564 | 0.076* | |
C16 | 0.7768 (3) | 1.0742 (5) | 0.0736 (4) | 0.060 (2) | |
H16 | 0.7981 | 1.0465 | 0.0537 | 0.072* | |
C17 | 0.7306 (4) | 0.7781 (5) | 0.0805 (4) | 0.073 (3) | |
H17A | 0.7252 | 0.8022 | 0.0425 | 0.087* | |
H17B | 0.6957 | 0.7900 | 0.0903 | 0.087* | |
C18 | 0.7394 (5) | 0.6876 (5) | 0.0793 (5) | 0.105 (4) | |
H18A | 0.7737 | 0.6764 | 0.0689 | 0.157* | |
H18B | 0.7054 | 0.6624 | 0.0508 | 0.157* | |
H18C | 0.7450 | 0.6644 | 0.1172 | 0.157* | |
C19 | 0.9736 (2) | 0.6572 (3) | 0.2764 (3) | 0.0286 (12) | |
H19A | 0.9712 | 0.6578 | 0.2358 | 0.034* | |
H19B | 0.9814 | 0.6001 | 0.2907 | 0.034* | |
C20 | 1.0897 (2) | 0.7147 (4) | 0.2871 (3) | 0.0292 (12) | |
C21 | 1.1218 (3) | 0.7832 (4) | 0.2835 (3) | 0.0387 (14) | |
H21 | 1.1139 | 0.8347 | 0.2970 | 0.046* | |
C22 | 1.1651 (3) | 0.7771 (4) | 0.2603 (3) | 0.0447 (16) | |
H22 | 1.1870 | 0.8243 | 0.2584 | 0.054* | |
C23 | 1.1770 (3) | 0.7024 (4) | 0.2398 (3) | 0.0461 (17) | |
H23 | 1.2065 | 0.6991 | 0.2234 | 0.055* | |
C24 | 1.1458 (3) | 0.6324 (4) | 0.2431 (3) | 0.0434 (16) | |
H24 | 1.1542 | 0.5812 | 0.2296 | 0.052* | |
C25 | 1.1021 (3) | 0.6386 (4) | 0.2667 (3) | 0.0377 (14) | |
H25 | 1.0805 | 0.5913 | 0.2689 | 0.045* | |
C26 | 1.0615 (3) | 0.6760 (4) | 0.3902 (3) | 0.0346 (14) | |
C27 | 1.0727 (3) | 0.7253 (5) | 0.4402 (3) | 0.0447 (16) | |
H27 | 1.0668 | 0.7829 | 0.4369 | 0.054* | |
C28 | 1.0923 (3) | 0.6884 (6) | 0.4935 (3) | 0.061 (2) | |
H28 | 1.1002 | 0.7213 | 0.5269 | 0.073* | |
C29 | 1.1006 (3) | 0.6060 (6) | 0.4992 (3) | 0.061 (2) | |
H29 | 1.1136 | 0.5820 | 0.5363 | 0.074* | |
C30 | 1.0899 (3) | 0.5563 (5) | 0.4507 (3) | 0.0519 (19) | |
H30 | 1.0957 | 0.4987 | 0.4551 | 0.062* | |
C31 | 1.0707 (3) | 0.5910 (4) | 0.3953 (3) | 0.0413 (15) | |
H31 | 1.0642 | 0.5578 | 0.3623 | 0.050* | |
C32 | 0.8515 (2) | 0.6121 (4) | 0.2458 (3) | 0.0328 (13) | |
C33 | 0.8615 (3) | 0.5573 (4) | 0.2072 (3) | 0.0415 (16) | |
H33 | 0.8973 | 0.5578 | 0.2006 | 0.050* | |
C34 | 0.8178 (3) | 0.5010 (4) | 0.1779 (3) | 0.0481 (17) | |
H34 | 0.8242 | 0.4634 | 0.1515 | 0.058* | |
C35 | 0.7657 (3) | 0.4999 (4) | 0.1874 (3) | 0.055 (2) | |
H35 | 0.7364 | 0.4623 | 0.1670 | 0.066* | |
C36 | 0.7564 (4) | 0.5527 (5) | 0.2257 (4) | 0.062 (2) | |
H36 | 0.7208 | 0.5513 | 0.2324 | 0.075* | |
C37 | 0.7994 (3) | 0.6095 (5) | 0.2554 (4) | 0.0527 (19) | |
H37 | 0.7927 | 0.6461 | 0.2822 | 0.063* | |
C38 | 0.9131 (2) | 0.6901 (3) | 0.3575 (3) | 0.0315 (13) | |
C39 | 0.9128 (3) | 0.7625 (4) | 0.3875 (3) | 0.0413 (15) | |
H39 | 0.9056 | 0.8133 | 0.3675 | 0.050* | |
C40 | 0.9232 (3) | 0.7613 (5) | 0.4467 (3) | 0.0521 (19) | |
H40 | 0.9224 | 0.8109 | 0.4665 | 0.063* | |
C41 | 0.9344 (3) | 0.6881 (5) | 0.4761 (3) | 0.054 (2) | |
H41 | 0.9424 | 0.6876 | 0.5163 | 0.065* | |
C42 | 0.9342 (3) | 0.6141 (5) | 0.4468 (3) | 0.056 (2) | |
H42 | 0.9413 | 0.5637 | 0.4672 | 0.067* | |
C43 | 0.9234 (3) | 0.6149 (4) | 0.3873 (3) | 0.0415 (15) | |
H43 | 0.9232 | 0.5651 | 0.3673 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Au1 | 0.03798 (14) | 0.02598 (12) | 0.03917 (15) | 0.00068 (9) | 0.01218 (11) | −0.00119 (10) |
Au2 | 0.03173 (13) | 0.02833 (12) | 0.03663 (14) | 0.00304 (9) | 0.01005 (10) | 0.00221 (10) |
S1 | 0.0507 (10) | 0.0294 (8) | 0.0440 (10) | 0.0059 (7) | 0.0033 (8) | −0.0017 (7) |
S2 | 0.0376 (8) | 0.0290 (7) | 0.0470 (10) | 0.0019 (6) | 0.0034 (7) | 0.0043 (7) |
P1 | 0.0299 (7) | 0.0259 (7) | 0.0310 (8) | −0.0013 (6) | 0.0102 (6) | 0.0011 (6) |
P2 | 0.0301 (8) | 0.0263 (7) | 0.0300 (8) | −0.0007 (6) | 0.0105 (6) | −0.0013 (6) |
O2 | 0.058 (4) | 0.046 (3) | 0.119 (6) | 0.014 (3) | 0.030 (4) | −0.007 (3) |
O3 | 0.085 (4) | 0.040 (3) | 0.088 (5) | 0.002 (3) | 0.023 (4) | 0.014 (3) |
O4 | 0.047 (3) | 0.039 (3) | 0.065 (4) | 0.001 (2) | 0.000 (3) | −0.002 (2) |
O5 | 0.152 (7) | 0.048 (4) | 0.078 (5) | 0.023 (4) | 0.028 (5) | 0.001 (3) |
O6 | 0.141 (7) | 0.057 (4) | 0.117 (7) | −0.035 (4) | 0.023 (6) | 0.013 (4) |
N1 | 0.064 (4) | 0.028 (3) | 0.064 (4) | 0.005 (3) | −0.007 (3) | −0.005 (3) |
N2 | 0.057 (4) | 0.030 (3) | 0.057 (4) | 0.001 (3) | 0.007 (3) | −0.001 (3) |
N3 | 0.039 (3) | 0.046 (3) | 0.062 (4) | 0.005 (3) | −0.005 (3) | 0.001 (3) |
N4 | 0.098 (6) | 0.043 (4) | 0.049 (4) | −0.004 (4) | −0.006 (4) | −0.001 (3) |
C1 | 0.053 (4) | 0.032 (3) | 0.057 (5) | 0.012 (3) | 0.002 (4) | 0.003 (3) |
C2 | 0.057 (4) | 0.029 (3) | 0.033 (4) | 0.007 (3) | 0.003 (3) | −0.005 (3) |
C3 | 0.057 (4) | 0.034 (3) | 0.053 (5) | −0.008 (3) | 0.024 (4) | −0.004 (3) |
C4 | 0.041 (4) | 0.036 (3) | 0.045 (4) | −0.008 (3) | 0.010 (3) | −0.014 (3) |
C5 | 0.045 (4) | 0.028 (3) | 0.035 (4) | 0.003 (3) | 0.011 (3) | −0.005 (3) |
C6 | 0.063 (4) | 0.034 (3) | 0.038 (4) | −0.006 (3) | 0.028 (3) | −0.005 (3) |
C7 | 0.040 (4) | 0.048 (4) | 0.051 (4) | 0.002 (3) | 0.018 (3) | −0.007 (3) |
O1 | 0.052 (7) | 0.036 (3) | 0.055 (6) | 0.020 (5) | −0.003 (4) | −0.005 (5) |
C8 | 0.070 (7) | 0.061 (5) | 0.071 (6) | 0.016 (5) | 0.008 (5) | 0.005 (5) |
C9 | 0.137 (9) | 0.116 (8) | 0.122 (9) | 0.011 (6) | 0.028 (6) | 0.001 (6) |
O1A | 0.052 (7) | 0.036 (3) | 0.055 (6) | 0.020 (5) | −0.003 (4) | −0.005 (5) |
C8A | 0.070 (7) | 0.061 (5) | 0.071 (6) | 0.016 (5) | 0.008 (5) | 0.005 (5) |
C9A | 0.137 (9) | 0.116 (8) | 0.122 (9) | 0.011 (6) | 0.028 (6) | 0.001 (6) |
C10 | 0.038 (3) | 0.034 (3) | 0.049 (4) | 0.000 (3) | 0.009 (3) | 0.005 (3) |
C11 | 0.030 (3) | 0.045 (4) | 0.061 (5) | 0.009 (3) | −0.003 (3) | 0.013 (4) |
C12 | 0.044 (4) | 0.048 (4) | 0.039 (4) | −0.001 (3) | 0.008 (3) | 0.004 (3) |
C13 | 0.054 (5) | 0.058 (4) | 0.041 (4) | 0.006 (4) | 0.012 (4) | −0.006 (4) |
C14 | 0.047 (4) | 0.042 (4) | 0.045 (4) | 0.002 (3) | −0.004 (3) | 0.006 (3) |
C15 | 0.047 (4) | 0.064 (5) | 0.075 (6) | −0.011 (4) | 0.014 (4) | 0.014 (5) |
C16 | 0.039 (4) | 0.066 (5) | 0.076 (6) | 0.011 (4) | 0.021 (4) | −0.002 (4) |
C17 | 0.056 (5) | 0.061 (5) | 0.077 (6) | −0.006 (4) | −0.008 (5) | −0.010 (5) |
C18 | 0.108 (9) | 0.053 (5) | 0.126 (11) | −0.011 (5) | 0.005 (8) | −0.025 (6) |
C19 | 0.031 (3) | 0.026 (3) | 0.029 (3) | −0.001 (2) | 0.011 (2) | −0.001 (2) |
C20 | 0.022 (3) | 0.035 (3) | 0.029 (3) | −0.002 (2) | 0.007 (2) | 0.005 (3) |
C21 | 0.035 (3) | 0.036 (3) | 0.039 (4) | −0.002 (3) | 0.005 (3) | 0.001 (3) |
C22 | 0.036 (3) | 0.048 (4) | 0.048 (4) | −0.010 (3) | 0.013 (3) | 0.010 (3) |
C23 | 0.035 (4) | 0.057 (4) | 0.049 (4) | 0.001 (3) | 0.019 (3) | 0.008 (3) |
C24 | 0.044 (4) | 0.043 (4) | 0.048 (4) | 0.007 (3) | 0.023 (3) | 0.006 (3) |
C25 | 0.041 (3) | 0.031 (3) | 0.043 (4) | 0.002 (3) | 0.016 (3) | 0.000 (3) |
C26 | 0.025 (3) | 0.044 (3) | 0.032 (3) | −0.001 (2) | 0.005 (3) | 0.004 (3) |
C27 | 0.042 (4) | 0.052 (4) | 0.037 (4) | 0.000 (3) | 0.009 (3) | −0.001 (3) |
C28 | 0.056 (5) | 0.092 (7) | 0.026 (4) | 0.001 (4) | 0.003 (3) | −0.001 (4) |
C29 | 0.044 (4) | 0.097 (7) | 0.032 (4) | 0.002 (4) | −0.001 (3) | 0.027 (4) |
C30 | 0.044 (4) | 0.054 (4) | 0.054 (5) | 0.007 (3) | 0.012 (4) | 0.026 (4) |
C31 | 0.039 (4) | 0.041 (3) | 0.043 (4) | 0.004 (3) | 0.015 (3) | 0.008 (3) |
C32 | 0.029 (3) | 0.032 (3) | 0.037 (3) | 0.001 (2) | 0.010 (3) | 0.005 (3) |
C33 | 0.034 (3) | 0.036 (3) | 0.051 (4) | −0.001 (3) | 0.010 (3) | −0.007 (3) |
C34 | 0.051 (4) | 0.036 (3) | 0.049 (4) | −0.003 (3) | 0.006 (3) | −0.010 (3) |
C35 | 0.058 (5) | 0.041 (4) | 0.052 (5) | −0.021 (3) | 0.001 (4) | −0.002 (4) |
C36 | 0.052 (5) | 0.069 (5) | 0.070 (6) | −0.026 (4) | 0.026 (4) | −0.007 (5) |
C37 | 0.049 (4) | 0.057 (4) | 0.059 (5) | −0.012 (4) | 0.028 (4) | −0.006 (4) |
C38 | 0.029 (3) | 0.034 (3) | 0.033 (3) | −0.002 (2) | 0.011 (3) | −0.003 (3) |
C39 | 0.040 (4) | 0.043 (4) | 0.040 (4) | 0.002 (3) | 0.013 (3) | −0.003 (3) |
C40 | 0.055 (4) | 0.058 (5) | 0.044 (4) | −0.003 (4) | 0.019 (4) | −0.018 (4) |
C41 | 0.054 (5) | 0.076 (6) | 0.033 (4) | −0.005 (4) | 0.015 (3) | −0.003 (4) |
C42 | 0.066 (5) | 0.061 (5) | 0.042 (4) | −0.008 (4) | 0.021 (4) | 0.013 (4) |
C43 | 0.054 (4) | 0.033 (3) | 0.044 (4) | −0.001 (3) | 0.025 (3) | 0.002 (3) |
Au1—P1 | 2.2582 (15) | C14—C15 | 1.378 (12) |
Au1—S1 | 2.3087 (16) | C15—C16 | 1.381 (11) |
Au2—P2 | 2.2421 (15) | C15—H15 | 0.9400 |
Au2—S2 | 2.3012 (16) | C16—H16 | 0.9400 |
Au1—Au2 | 3.2320 (5) | C17—C18 | 1.479 (11) |
S1—C1 | 1.759 (8) | C17—H17A | 0.9800 |
S2—C10 | 1.761 (7) | C17—H17B | 0.9800 |
P1—C20 | 1.815 (6) | C18—H18A | 0.9700 |
P1—C26 | 1.816 (6) | C18—H18B | 0.9700 |
P1—C19 | 1.839 (6) | C18—H18C | 0.9700 |
P2—C38 | 1.808 (6) | C19—H19A | 0.9800 |
P2—C32 | 1.826 (6) | C19—H19B | 0.9800 |
P2—C19 | 1.831 (6) | C20—C21 | 1.377 (8) |
O2—N2 | 1.224 (8) | C20—C25 | 1.399 (8) |
O3—N2 | 1.213 (8) | C21—C22 | 1.366 (9) |
O4—C10 | 1.364 (7) | C21—H21 | 0.9400 |
O4—C17 | 1.468 (9) | C22—C23 | 1.376 (10) |
O5—N4 | 1.215 (11) | C22—H22 | 0.9400 |
O6—N4 | 1.215 (11) | C23—C24 | 1.381 (9) |
N1—C1 | 1.264 (9) | C23—H23 | 0.9400 |
N1—C2 | 1.397 (8) | C24—C25 | 1.383 (9) |
N2—C5 | 1.470 (8) | C24—H24 | 0.9400 |
N3—C10 | 1.249 (8) | C25—H25 | 0.9400 |
N3—C11 | 1.405 (9) | C26—C31 | 1.389 (9) |
N4—C14 | 1.446 (9) | C26—C27 | 1.410 (9) |
C1—O1A | 1.35 (4) | C27—C28 | 1.368 (10) |
C1—O1 | 1.377 (14) | C27—H27 | 0.9400 |
C2—C3 | 1.391 (10) | C28—C29 | 1.346 (12) |
C2—C7 | 1.392 (10) | C28—H28 | 0.9400 |
C3—C4 | 1.382 (9) | C29—C30 | 1.387 (11) |
C3—H3 | 0.9400 | C29—H29 | 0.9400 |
C4—C5 | 1.384 (9) | C30—C31 | 1.395 (9) |
C4—H4 | 0.9400 | C30—H30 | 0.9400 |
C5—C6 | 1.391 (9) | C31—H31 | 0.9400 |
C6—C7 | 1.371 (9) | C32—C37 | 1.371 (9) |
C6—H6 | 0.9400 | C32—C33 | 1.381 (9) |
C7—H7 | 0.9400 | C33—C34 | 1.396 (9) |
O1—C8 | 1.465 (9) | C33—H33 | 0.9400 |
C8—C9 | 1.473 (10) | C34—C35 | 1.368 (10) |
C8—H8A | 0.9800 | C34—H34 | 0.9400 |
C8—H8B | 0.9800 | C35—C36 | 1.347 (11) |
C9—H9A | 0.9700 | C35—H35 | 0.9400 |
C9—H9B | 0.9700 | C36—C37 | 1.394 (10) |
C9—H9C | 0.9700 | C36—H36 | 0.9400 |
O1A—C8A | 1.455 (10) | C37—H37 | 0.9400 |
C8A—C9A | 1.478 (10) | C38—C39 | 1.383 (9) |
C8A—H8C | 0.9800 | C38—C43 | 1.394 (9) |
C8A—H8D | 0.9800 | C39—C40 | 1.390 (10) |
C9A—H9D | 0.9700 | C39—H39 | 0.9400 |
C9A—H9E | 0.9700 | C40—C41 | 1.362 (11) |
C9A—H9F | 0.9700 | C40—H40 | 0.9400 |
C11—C12 | 1.395 (10) | C41—C42 | 1.393 (11) |
C11—C16 | 1.416 (11) | C41—H41 | 0.9400 |
C12—C13 | 1.376 (10) | C42—C43 | 1.396 (10) |
C12—H12 | 0.9400 | C42—H42 | 0.9400 |
C13—C14 | 1.365 (11) | C43—H43 | 0.9400 |
C13—H13 | 0.9400 | ||
P1—Au1—S1 | 172.77 (6) | C15—C16—H16 | 120.1 |
P1—Au1—Au2 | 88.36 (4) | C11—C16—H16 | 120.1 |
S1—Au1—Au2 | 98.86 (4) | O4—C17—C18 | 107.7 (7) |
P2—Au2—S2 | 173.84 (6) | O4—C17—H17A | 110.2 |
P2—Au2—Au1 | 80.42 (4) | C18—C17—H17A | 110.2 |
S2—Au2—Au1 | 104.74 (4) | O4—C17—H17B | 110.2 |
C1—S1—Au1 | 102.4 (2) | C18—C17—H17B | 110.2 |
C10—S2—Au2 | 100.7 (2) | H17A—C17—H17B | 108.5 |
C20—P1—C26 | 106.9 (3) | C17—C18—H18A | 109.5 |
C20—P1—C19 | 105.3 (3) | C17—C18—H18B | 109.5 |
C26—P1—C19 | 104.7 (3) | H18A—C18—H18B | 109.5 |
C20—P1—Au1 | 111.07 (19) | C17—C18—H18C | 109.5 |
C26—P1—Au1 | 112.6 (2) | H18A—C18—H18C | 109.5 |
C19—P1—Au1 | 115.60 (19) | H18B—C18—H18C | 109.5 |
C38—P2—C32 | 107.0 (3) | P2—C19—P1 | 110.1 (3) |
C38—P2—C19 | 106.5 (3) | P2—C19—H19A | 109.6 |
C32—P2—C19 | 105.1 (3) | P1—C19—H19A | 109.6 |
C38—P2—Au2 | 115.44 (19) | P2—C19—H19B | 109.6 |
C32—P2—Au2 | 111.7 (2) | P1—C19—H19B | 109.6 |
C19—P2—Au2 | 110.46 (19) | H19A—C19—H19B | 108.2 |
C10—O4—C17 | 116.5 (5) | C21—C20—C25 | 118.9 (6) |
C1—N1—C2 | 122.7 (6) | C21—C20—P1 | 119.3 (5) |
O3—N2—O2 | 122.6 (6) | C25—C20—P1 | 121.8 (4) |
O3—N2—C5 | 118.8 (6) | C22—C21—C20 | 120.6 (6) |
O2—N2—C5 | 118.6 (6) | C22—C21—H21 | 119.7 |
C10—N3—C11 | 121.0 (6) | C20—C21—H21 | 119.7 |
O6—N4—O5 | 122.9 (8) | C21—C22—C23 | 120.5 (6) |
O6—N4—C14 | 120.2 (10) | C21—C22—H22 | 119.7 |
O5—N4—C14 | 116.9 (9) | C23—C22—H22 | 119.7 |
N1—C1—O1A | 117.8 (14) | C22—C23—C24 | 120.3 (6) |
N1—C1—O1 | 120.2 (8) | C22—C23—H23 | 119.9 |
O1A—C1—O1 | 24.6 (12) | C24—C23—H23 | 119.9 |
N1—C1—S1 | 125.9 (5) | C23—C24—C25 | 119.2 (6) |
O1A—C1—S1 | 114.1 (14) | C23—C24—H24 | 120.4 |
O1—C1—S1 | 113.3 (7) | C25—C24—H24 | 120.4 |
C3—C2—C7 | 118.3 (6) | C24—C25—C20 | 120.5 (6) |
C3—C2—N1 | 122.0 (7) | C24—C25—H25 | 119.8 |
C7—C2—N1 | 119.4 (7) | C20—C25—H25 | 119.8 |
C4—C3—C2 | 121.6 (6) | C31—C26—C27 | 120.2 (6) |
C4—C3—H3 | 119.2 | C31—C26—P1 | 120.8 (5) |
C2—C3—H3 | 119.2 | C27—C26—P1 | 119.0 (5) |
C3—C4—C5 | 117.8 (6) | C28—C27—C26 | 119.2 (7) |
C3—C4—H4 | 121.1 | C28—C27—H27 | 120.4 |
C5—C4—H4 | 121.1 | C26—C27—H27 | 120.4 |
C4—C5—C6 | 122.5 (6) | C29—C28—C27 | 121.4 (8) |
C4—C5—N2 | 118.9 (6) | C29—C28—H28 | 119.3 |
C6—C5—N2 | 118.6 (6) | C27—C28—H28 | 119.3 |
C7—C6—C5 | 117.9 (6) | C28—C29—C30 | 120.4 (7) |
C7—C6—H6 | 121.1 | C28—C29—H29 | 119.8 |
C5—C6—H6 | 121.1 | C30—C29—H29 | 119.8 |
C6—C7—C2 | 121.9 (6) | C29—C30—C31 | 120.4 (7) |
C6—C7—H7 | 119.1 | C29—C30—H30 | 119.8 |
C2—C7—H7 | 119.1 | C31—C30—H30 | 119.8 |
C1—O1—C8 | 115.3 (12) | C26—C31—C30 | 118.3 (7) |
O1—C8—C9 | 110.1 (17) | C26—C31—H31 | 120.8 |
O1—C8—H8A | 109.6 | C30—C31—H31 | 120.8 |
C9—C8—H8A | 109.6 | C37—C32—C33 | 119.6 (6) |
O1—C8—H8B | 109.6 | C37—C32—P2 | 118.7 (5) |
C9—C8—H8B | 109.6 | C33—C32—P2 | 121.5 (5) |
H8A—C8—H8B | 108.1 | C32—C33—C34 | 119.0 (6) |
C1—O1A—C8A | 123 (3) | C32—C33—H33 | 120.5 |
O1A—C8A—C9A | 110 (4) | C34—C33—H33 | 120.5 |
O1A—C8A—H8C | 109.7 | C35—C34—C33 | 120.7 (7) |
C9A—C8A—H8C | 109.7 | C35—C34—H34 | 119.7 |
O1A—C8A—H8D | 109.7 | C33—C34—H34 | 119.7 |
C9A—C8A—H8D | 109.7 | C36—C35—C34 | 120.1 (7) |
H8C—C8A—H8D | 108.2 | C36—C35—H35 | 119.9 |
C8A—C9A—H9D | 109.5 | C34—C35—H35 | 119.9 |
C8A—C9A—H9E | 109.5 | C35—C36—C37 | 120.3 (7) |
H9D—C9A—H9E | 109.5 | C35—C36—H36 | 119.8 |
C8A—C9A—H9F | 109.5 | C37—C36—H36 | 119.8 |
H9D—C9A—H9F | 109.5 | C32—C37—C36 | 120.2 (7) |
H9E—C9A—H9F | 109.5 | C32—C37—H37 | 119.9 |
N3—C10—O4 | 121.2 (6) | C36—C37—H37 | 119.9 |
N3—C10—S2 | 125.3 (5) | C39—C38—C43 | 119.4 (6) |
O4—C10—S2 | 113.5 (5) | C39—C38—P2 | 120.8 (5) |
C12—C11—N3 | 120.0 (7) | C43—C38—P2 | 119.8 (5) |
C12—C11—C16 | 119.5 (7) | C38—C39—C40 | 120.9 (7) |
N3—C11—C16 | 120.2 (7) | C38—C39—H39 | 119.6 |
C13—C12—C11 | 120.1 (7) | C40—C39—H39 | 119.6 |
C13—C12—H12 | 120.0 | C41—C40—C39 | 119.9 (7) |
C11—C12—H12 | 120.0 | C41—C40—H40 | 120.0 |
C14—C13—C12 | 119.2 (7) | C39—C40—H40 | 120.0 |
C14—C13—H13 | 120.4 | C40—C41—C42 | 120.4 (7) |
C12—C13—H13 | 120.4 | C40—C41—H41 | 119.8 |
C13—C14—C15 | 123.0 (7) | C42—C41—H41 | 119.8 |
C13—C14—N4 | 119.9 (8) | C41—C42—C43 | 120.0 (7) |
C15—C14—N4 | 117.2 (8) | C41—C42—H42 | 120.0 |
C14—C15—C16 | 118.5 (8) | C43—C42—H42 | 120.0 |
C14—C15—H15 | 120.8 | C38—C43—C42 | 119.4 (7) |
C16—C15—H15 | 120.8 | C38—C43—H43 | 120.3 |
C15—C16—C11 | 119.8 (8) | C42—C43—H43 | 120.3 |
P1—Au1—Au2—P2 | 28.86 (6) | N4—C14—C15—C16 | −176.7 (7) |
S1—Au1—Au2—P2 | −151.57 (7) | C14—C15—C16—C11 | −2.6 (12) |
P1—Au1—Au2—S2 | −147.71 (6) | C12—C11—C16—C15 | 1.6 (11) |
S1—Au1—Au2—S2 | 31.86 (7) | N3—C11—C16—C15 | 175.0 (7) |
P1—Au1—S1—C1 | −22.7 (6) | C10—O4—C17—C18 | 176.7 (8) |
Au2—Au1—S1—C1 | 160.7 (3) | C38—P2—C19—P1 | −58.8 (4) |
P2—Au2—S2—C10 | 22.0 (7) | C32—P2—C19—P1 | −172.1 (3) |
Au1—Au2—S2—C10 | 168.6 (2) | Au2—P2—C19—P1 | 67.2 (3) |
S1—Au1—P1—C20 | −59.6 (6) | C20—P1—C19—P2 | −155.5 (3) |
Au2—Au1—P1—C20 | 117.0 (2) | C26—P1—C19—P2 | 92.0 (3) |
S1—Au1—P1—C26 | 60.2 (6) | Au1—P1—C19—P2 | −32.5 (4) |
Au2—Au1—P1—C26 | −123.2 (2) | C26—P1—C20—C21 | −106.5 (5) |
S1—Au1—P1—C19 | −180 (100) | C19—P1—C20—C21 | 142.6 (5) |
Au2—Au1—P1—C19 | −2.9 (2) | Au1—P1—C20—C21 | 16.7 (5) |
S2—Au2—P2—C38 | −145.2 (6) | C26—P1—C20—C25 | 72.4 (5) |
Au1—Au2—P2—C38 | 67.5 (2) | C19—P1—C20—C25 | −38.6 (6) |
S2—Au2—P2—C32 | −22.6 (6) | Au1—P1—C20—C25 | −164.4 (4) |
Au1—Au2—P2—C32 | −170.0 (2) | C25—C20—C21—C22 | 0.0 (9) |
S2—Au2—P2—C19 | 94.0 (6) | P1—C20—C21—C22 | 178.8 (5) |
Au1—Au2—P2—C19 | −53.4 (2) | C20—C21—C22—C23 | 0.5 (10) |
C2—N1—C1—O1A | −158.0 (15) | C21—C22—C23—C24 | −0.9 (11) |
C2—N1—C1—O1 | 173.9 (10) | C22—C23—C24—C25 | 0.8 (11) |
C2—N1—C1—S1 | 4.2 (13) | C23—C24—C25—C20 | −0.3 (10) |
Au1—S1—C1—N1 | 171.7 (8) | C21—C20—C25—C24 | −0.1 (10) |
Au1—S1—C1—O1A | −25.6 (14) | P1—C20—C25—C24 | −178.9 (5) |
Au1—S1—C1—O1 | 1.4 (9) | C20—P1—C26—C31 | −66.9 (6) |
C1—N1—C2—C3 | 63.0 (12) | C19—P1—C26—C31 | 44.5 (6) |
C1—N1—C2—C7 | −123.0 (9) | Au1—P1—C26—C31 | 170.8 (4) |
C7—C2—C3—C4 | −0.2 (11) | C20—P1—C26—C27 | 114.3 (5) |
N1—C2—C3—C4 | 173.8 (7) | C19—P1—C26—C27 | −134.4 (5) |
C2—C3—C4—C5 | 0.3 (11) | Au1—P1—C26—C27 | −8.0 (6) |
C3—C4—C5—C6 | −0.6 (10) | C31—C26—C27—C28 | −0.5 (10) |
C3—C4—C5—N2 | −179.1 (6) | P1—C26—C27—C28 | 178.3 (6) |
O3—N2—C5—C4 | −169.8 (6) | C26—C27—C28—C29 | −0.6 (12) |
O2—N2—C5—C4 | 9.5 (10) | C27—C28—C29—C30 | 0.8 (12) |
O3—N2—C5—C6 | 11.7 (10) | C28—C29—C30—C31 | 0.1 (11) |
O2—N2—C5—C6 | −169.1 (6) | C27—C26—C31—C30 | 1.4 (9) |
C4—C5—C6—C7 | 0.9 (10) | P1—C26—C31—C30 | −177.4 (5) |
N2—C5—C6—C7 | 179.4 (6) | C29—C30—C31—C26 | −1.3 (10) |
C5—C6—C7—C2 | −0.8 (10) | C38—P2—C32—C37 | 50.4 (6) |
C3—C2—C7—C6 | 0.5 (10) | C19—P2—C32—C37 | 163.3 (6) |
N1—C2—C7—C6 | −173.7 (7) | Au2—P2—C32—C37 | −76.9 (6) |
N1—C1—O1—C8 | 11.6 (19) | C38—P2—C32—C33 | −133.3 (5) |
O1A—C1—O1—C8 | −80 (4) | C19—P2—C32—C33 | −20.4 (6) |
S1—C1—O1—C8 | −177.5 (11) | Au2—P2—C32—C33 | 99.4 (5) |
C1—O1—C8—C9 | 76.0 (19) | C37—C32—C33—C34 | 0.9 (10) |
N1—C1—O1A—C8A | −10 (4) | P2—C32—C33—C34 | −175.3 (5) |
O1—C1—O1A—C8A | 93 (5) | C32—C33—C34—C35 | 0.0 (11) |
S1—C1—O1A—C8A | −174 (2) | C33—C34—C35—C36 | −0.9 (12) |
C1—O1A—C8A—C9A | −74 (4) | C34—C35—C36—C37 | 0.9 (13) |
C11—N3—C10—O4 | −177.3 (7) | C33—C32—C37—C36 | −1.0 (11) |
C11—N3—C10—S2 | 2.8 (12) | P2—C32—C37—C36 | 175.4 (6) |
C17—O4—C10—N3 | −0.6 (11) | C35—C36—C37—C32 | 0.1 (13) |
C17—O4—C10—S2 | 179.3 (6) | C32—P2—C38—C39 | −134.5 (5) |
Au2—S2—C10—N3 | 161.0 (7) | C19—P2—C38—C39 | 113.6 (5) |
Au2—S2—C10—O4 | −18.9 (6) | Au2—P2—C38—C39 | −9.4 (6) |
C10—N3—C11—C12 | −104.3 (9) | C32—P2—C38—C43 | 49.2 (6) |
C10—N3—C11—C16 | 82.4 (10) | C19—P2—C38—C43 | −62.8 (5) |
N3—C11—C12—C13 | −174.0 (6) | Au2—P2—C38—C43 | 174.2 (4) |
C16—C11—C12—C13 | −0.6 (11) | C43—C38—C39—C40 | 0.4 (10) |
C11—C12—C13—C14 | 0.7 (11) | P2—C38—C39—C40 | −176.0 (5) |
C12—C13—C14—C15 | −1.8 (12) | C38—C39—C40—C41 | 0.8 (11) |
C12—C13—C14—N4 | 177.7 (7) | C39—C40—C41—C42 | −1.6 (12) |
O6—N4—C14—C13 | 169.9 (8) | C40—C41—C42—C43 | 1.1 (12) |
O5—N4—C14—C13 | −11.0 (11) | C39—C38—C43—C42 | −0.9 (10) |
O6—N4—C14—C15 | −10.6 (11) | P2—C38—C43—C42 | 175.5 (5) |
O5—N4—C14—C15 | 168.5 (8) | C41—C42—C43—C38 | 0.1 (11) |
C13—C14—C15—C16 | 2.7 (12) |
Cg1 and Cg2 are the centroids of the C2–C7 and C38–C43 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C41—H41···Cg1i | 0.94 | 2.73 | 3.576 (8) | 151 |
C17—H17b···Cg2ii | 0.98 | 2.87 | 3.821 (11) | 163 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+3/2, −y+3/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Au2(C9H9N2O3S)2(C25H22P2)] |
Mr | 1228.83 |
Crystal system, space group | Monoclinic, I2/a |
Temperature (K) | 223 |
a, b, c (Å) | 24.400 (3), 16.1419 (16), 24.594 (2) |
β (°) | 110.252 (9) |
V (Å3) | 9087.9 (16) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 6.66 |
Crystal size (mm) | 0.31 × 0.13 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.445, 1 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31967, 10427, 7923 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.110, 1.02 |
No. of reflections | 10427 |
No. of parameters | 549 |
No. of restraints | 28 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.52, −1.19 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).
Cg1 and Cg2 are the centroids of the C2–C7 and C38–C43 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C41—H41···Cg1i | 0.94 | 2.73 | 3.576 (8) | 151 |
C17—H17b···Cg2ii | 0.98 | 2.87 | 3.821 (11) | 163 |
Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) −x+3/2, −y+3/2, −z+1/2. |
Acknowledgements
The National University of Singapore (grant No. R-143–000-213–112) is thanked for support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The investigation of dinuclear molecules related to molecules with the general formula R3PAu[SC(OR')═ NR''], for R, R' and R'' = alkyl and aryl,have proved useful for crystal engineering studies, in particular in terms of a competition between intra- and inter-molecular aurophilic (Au···Au) interactions, and the influence of these upon luminescence (Ho et al., 2006; Ho & Tiekink, 2007; Kuan et al., 2008). The title compound, (I), is the ethoxy analogue of the previously reported methoxy derivative (Ho et al., 2006).
The nearly linear SP coordination geometry observed for each Au atom, Fig. 1, is defined by one P atom of the bidentate bridging diphosphine ligand and the thiolate-S derived from the carbonimidothioate anion, Table 1. Deviations from the ideal linearity [S—Au—P = 172.77 (6) and 173.84 (6) °] is traced to the close intramolecular Au···O contacts [2.968 (11) and 2.963 (4) Å]. Overall, the conformation of the dinuclear molecule is a U-shape which allows for the formation of an intramolecular Au···Au contact of 3.2320 (5) Å which is longer than 3.1589 (4) Å found in the methoxy derivative (Ho et al. 2006).
The major feature of the crystal packing is the presence of C–H···π interactions, Table 2 and Fig. 2.