metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

A second polymorph of chlorido(hy­droxy­di­phenyl­phosphane)gold(I)

aSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private, Bag X54001, Durban, 4000, South Africa, and bDepartment of Chemistry, Michigan State University, East Lansing, MI, 48824-1322, USA
*Correspondence e-mail: vanzylw@ukzn.ac.za

(Received 29 July 2011; accepted 2 September 2011; online 14 September 2011)

The title complex, [AuCl{(C6H5)2P(OH)-κP}] or [AuCl(C12H11OP)], contains two independent mol­ecules in the asymmetric unit and is a polymorph of a previously reported structure [Hollatz et al. (1999[Hollatz, C., Schier, A., Riede, J. & Schmidbaur, H. (1999). J. Chem. Soc., Dalton Trans. pp. 111-114.]) J. Chem. Soc. Dalton Trans. pp. 111–114]. The crystal structure exhibits inter­molecular Au⋯Au inter­actions with alternate distances of 3.0112 (3) Å and 3.0375 (2) Å. The Cl—Au—P bond angle varies between different mol­ecular units, depending on the degree of influence of the intra­molecular the O—H⋯Cl hydrogen bond; the angle thus varies between negligible distortion from linearity at 179.23 (3)° and more significant distortion at 170.39 (4)°, which differs from the previously reported polymorph in which both these angles are approximately 170°. The Au—Cl [2.3366 (9) and 2.3131 (10)Å] and Au—P [2.2304 (10) and 2.2254 (10) Å] bond lengths vary slightly between the two independent mol­ecules but overall, the bond lengths are in good agreement with those in the previously reported polymorph.

Related literature

For background to polymorphism, see: Braga & Grepioni (2007)[Braga, D. & Grepioni, F. (2007). Editors. Making Crystals by Design: Methods, Techniques and Applications. Weinheim: Wiley-VCH Verlag.]. Polymorphs of chloro­gold(I) phosphine complexes are relatively common (Healy, 2003[Healy, P. C. (2003). Acta Cryst. E59, m1112-m1114.]) and often display inter­esting photochemical properties (Hoshino et al., 2010[Hoshino, M., Uekusa, H., Ishii, S., Otsuka, T., Kaizu, Y., Ozawa, Y. & Toriumi, K. (2010). Inorg. Chem. 49, 7257-7265.]). For the previously reported polymorph of the title compound, see: Hollatz et al. (1999[Hollatz, C., Schier, A., Riede, J. & Schmidbaur, H. (1999). J. Chem. Soc., Dalton Trans. pp. 111-114.]). For our studies on gold and P-based ligand complexes, see: Van Zyl (2010[Van Zyl, W. E. (2010). Comments Inorg. Chem. 31, 13-45.]).

[Scheme 1]

Experimental

Crystal data
  • [AuCl(C12H11OP)]

  • Mr = 434.59

  • Monoclinic, C 2/c

  • a = 29.2734 (18) Å

  • b = 10.2321 (6) Å

  • c = 17.5643 (11) Å

  • β = 106.483 (1)°

  • V = 5044.8 (5) Å3

  • Z = 16

  • Mo Kα radiation

  • μ = 11.98 mm−1

  • T = 173 K

  • 0.32 × 0.13 × 0.06 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.371, Tmax = 0.745

  • 18295 measured reflections

  • 4651 independent reflections

  • 4183 reflections with I > 2σ(I)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.019

  • wR(F2) = 0.048

  • S = 1.03

  • 4651 reflections

  • 291 parameters

  • H-atom parameters constrained

  • Δρmax = 0.74 e Å−3

  • Δρmin = −0.63 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯Cl2 0.84 2.16 2.994 (3) 170
O2—H2⋯Cl1 0.84 2.23 3.050 (3) 166

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Polymorphism is generally described as the ability of the same chemical substance to exist in at least two different crystalline forms (Braga & Grepioni 2007). Data collection at 173 K showed that the gold(I) compound, (I), had crystallized in monoclinic space group C2/c with sixteen formula units per unit cell (final R value 0.019) which differs significantly from a previously reported crystal structure of this compound (Hollatz et al., 1999), obtained at 195 K in triclinic space group P1 with four formula units per unit cell and a final R value of 0.036. Due to the nearness of the respective data collection temperatures, we disregard an interpretation of this result as indicating that the structure had undergone a significant phase transition between 173 and 195 K, and thus conclude that the structure of complex (I) presented here is a genuine polymorph and not the consequence of a phase transition. Indeed, polymorphs of chlorogold(I) phosphine complexes are relatively common (Healy, 2003) and often display interesting photochemical properties (Hoshino et al., 2010).

In our continued studies on gold and P-based ligand complexes (Van Zyl, 2010), the title complex [AuCl{(C6H5)2P(OH)}], (I), was readily synthesized from the reaction between Ph2PCl in wet dichloromethane (i.e. containing traces of water) followed by addition of [AuCl(tht)] (tht = tetrahydrothiophene). In the previously reported study of the polymorph, [AuCl(Me2S)] was reacted with Ph2P(OH) in CH2Cl2 solvent with the elimination of Me2S, forming [AuCl{(C6H5)2P(OH)}]. A solution 31P NMR study showed a sharp singlet at δ = 89.5 for (I) which corresponds well with the value of δ = 90.4 for the polymorph (Hollatz et al., 1999). Since polymorphs must have the same resonance in solution, and since the same solvent (CDCl3) was used in both cases, the small difference (0.9 p.p.m.) is ascribed to possible difference in temperature (293 versus 298 K) during data acquisition. A single-crystal X-ray analysis of the compound subsequently provided unambiguous proof of the authenticity of the complex, and for it to be a polymorph.

The crystal structure of (I) presented here includes four molecular units along a virtual chain (described as two "inner" and two "outer" units) all linked through intermolecular Au···Au interactions with alternate distances of 3.0112 (3) Å (between the two inner units) and 3.0375 (2) Å between an inner and outer unit which are both shorter than the corresponding distance for the reported polymorph, at 3.1112 (7) Å. The Cl—Au—P bond angles between the two inner complexes have in one case negligible distortion away from linearity at 179.23 (3)° while in the other case it has significant distortion at 170.39 (4)°, which differs from the previously reported polymorph where both these angles are approximately 170°. This difference originates through the varying influence of O—H···Cl type hydrogen bonding within the respective molecular units: the stronger the H-bonding, the more the distortion. In the case of (I), the one Cl—Au—P unit is positioned too far from a P—O—H unit for any O—H···Cl hydrogen bonding [d(H···Cl) = 2.23 Å] to occur whilst the other Cl—Au—P unit is much closer to a P—O—H unit at d(H···Cl) = 2.16 Å, and this causes the observed distortion. In the triclinic polymorph, hydrogen bonding is present on both monomeric units at d(H···Cl) = 2.03 and 2.11 Å, respectively, which leads to significant distortion from linearity for both Cl—Au—P units.The Au—Cl bond length of the inner unit is 2.3366 (9) and for the outer unit 2.3131 (10) Å, respectively, whilst the Au—P bond lengths are slightly shorter at 2.2304 (10) (inner) and 2.2254 (10) Å (outer), respectively; these bond length results are in good agreement with the previously reported structure. The P—O bond length in (I) is 1.592 (3) Å versus 1.597 (5) Å in the triclinic polymorph. Based on the current studies, it cannot readily be inferred whether the polymorph with the shorter Au···Au interactions is the thermodynamically more stable of the two. Note that structure (I) has a slightly lower calculated density at 2.289 g/cm3 compared to the other polymorph at 2.309 g/cm3, suggesting the molecular packing in the latter is more efficient, presumably resulting from a larger extent of hydrogen bonding.

Related literature top

For background to polymorphism, see: Braga & Grepioni (2007). Polymorphs of chlorogold(I) phosphine complexes are relatively common (Healy, 2003) and often display interesting photochemical properties (Hoshino et al., 2010). For the previously reported polymorph of the title compound, see: Hollatz et al. (1999). For our studies on gold and P-based ligand complexes, see: Van Zyl (2010).

Experimental top

Preparation and characterization of complex (I): A Schlenk flask equipped with a magnetic stirrer bar was charged with wet dichloromethane (5 ml) and this was followed by addition of ClPPh2 (0.210 ml, 1.11 mmol). The mixture was stirred for 20 minutes at room temperature. A dichloromethane solution of [AuCl(tht)] (354 mg, 1.11 mmol) was added in one portion and the resulting mixture stirred for a further 15 minutes. All of the solvent and tht were removed and the product isolated as a free-flowing white powder. 31P NMR (101 MHz, CDCl3, 298 K) δP = 89.2 (s, 1P). Single crystals were obtained by slow diffusion of hexane vapor into a saturated dichloromethane solution.

Refinement top

All H atoms were placed in calculated positions and refined using a riding model. C—H(aromatic) = 0.94 Å and Uiso(H) = 1.2Ueq(C) C—H (alaphatic) = 0.99 Å and Uiso(H) = 1.2Ueq(C) CH2 = 0.98 Å and Uiso(H) = 1.2Ueq(C) CH3 = 0.97Å and Uiso(H) = 1.5Ueq(C) N—H = 0.86 (0.92)Å and Uiso(H) = 1.2 Ueq(N) O—H(alcohol) = 0.85Åand Uiso(H) = 1.2Ueq(O) O—H(acid) = 0.82 Å and Uiso(H) = 1.5Ueq(O).

Structure description top

Polymorphism is generally described as the ability of the same chemical substance to exist in at least two different crystalline forms (Braga & Grepioni 2007). Data collection at 173 K showed that the gold(I) compound, (I), had crystallized in monoclinic space group C2/c with sixteen formula units per unit cell (final R value 0.019) which differs significantly from a previously reported crystal structure of this compound (Hollatz et al., 1999), obtained at 195 K in triclinic space group P1 with four formula units per unit cell and a final R value of 0.036. Due to the nearness of the respective data collection temperatures, we disregard an interpretation of this result as indicating that the structure had undergone a significant phase transition between 173 and 195 K, and thus conclude that the structure of complex (I) presented here is a genuine polymorph and not the consequence of a phase transition. Indeed, polymorphs of chlorogold(I) phosphine complexes are relatively common (Healy, 2003) and often display interesting photochemical properties (Hoshino et al., 2010).

In our continued studies on gold and P-based ligand complexes (Van Zyl, 2010), the title complex [AuCl{(C6H5)2P(OH)}], (I), was readily synthesized from the reaction between Ph2PCl in wet dichloromethane (i.e. containing traces of water) followed by addition of [AuCl(tht)] (tht = tetrahydrothiophene). In the previously reported study of the polymorph, [AuCl(Me2S)] was reacted with Ph2P(OH) in CH2Cl2 solvent with the elimination of Me2S, forming [AuCl{(C6H5)2P(OH)}]. A solution 31P NMR study showed a sharp singlet at δ = 89.5 for (I) which corresponds well with the value of δ = 90.4 for the polymorph (Hollatz et al., 1999). Since polymorphs must have the same resonance in solution, and since the same solvent (CDCl3) was used in both cases, the small difference (0.9 p.p.m.) is ascribed to possible difference in temperature (293 versus 298 K) during data acquisition. A single-crystal X-ray analysis of the compound subsequently provided unambiguous proof of the authenticity of the complex, and for it to be a polymorph.

The crystal structure of (I) presented here includes four molecular units along a virtual chain (described as two "inner" and two "outer" units) all linked through intermolecular Au···Au interactions with alternate distances of 3.0112 (3) Å (between the two inner units) and 3.0375 (2) Å between an inner and outer unit which are both shorter than the corresponding distance for the reported polymorph, at 3.1112 (7) Å. The Cl—Au—P bond angles between the two inner complexes have in one case negligible distortion away from linearity at 179.23 (3)° while in the other case it has significant distortion at 170.39 (4)°, which differs from the previously reported polymorph where both these angles are approximately 170°. This difference originates through the varying influence of O—H···Cl type hydrogen bonding within the respective molecular units: the stronger the H-bonding, the more the distortion. In the case of (I), the one Cl—Au—P unit is positioned too far from a P—O—H unit for any O—H···Cl hydrogen bonding [d(H···Cl) = 2.23 Å] to occur whilst the other Cl—Au—P unit is much closer to a P—O—H unit at d(H···Cl) = 2.16 Å, and this causes the observed distortion. In the triclinic polymorph, hydrogen bonding is present on both monomeric units at d(H···Cl) = 2.03 and 2.11 Å, respectively, which leads to significant distortion from linearity for both Cl—Au—P units.The Au—Cl bond length of the inner unit is 2.3366 (9) and for the outer unit 2.3131 (10) Å, respectively, whilst the Au—P bond lengths are slightly shorter at 2.2304 (10) (inner) and 2.2254 (10) Å (outer), respectively; these bond length results are in good agreement with the previously reported structure. The P—O bond length in (I) is 1.592 (3) Å versus 1.597 (5) Å in the triclinic polymorph. Based on the current studies, it cannot readily be inferred whether the polymorph with the shorter Au···Au interactions is the thermodynamically more stable of the two. Note that structure (I) has a slightly lower calculated density at 2.289 g/cm3 compared to the other polymorph at 2.309 g/cm3, suggesting the molecular packing in the latter is more efficient, presumably resulting from a larger extent of hydrogen bonding.

For background to polymorphism, see: Braga & Grepioni (2007). Polymorphs of chlorogold(I) phosphine complexes are relatively common (Healy, 2003) and often display interesting photochemical properties (Hoshino et al., 2010). For the previously reported polymorph of the title compound, see: Hollatz et al. (1999). For our studies on gold and P-based ligand complexes, see: Van Zyl (2010).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the intermolecular Au—Au interaction between two units with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of the crystal structure, viewed along the a axis.
[Figure 3] Fig. 3. A molecular drawing showing four units, two inner and two outer. Note the atoms of the inner P—Au—Cl moiety points in approximately the same direction, whilst the outer two in the opposite direction.
(Hydroxydiphenylphosphane)chloridogold(I) top
Crystal data top
[AuCl(C12H11OP)]F(000) = 3232
Mr = 434.59Dx = 2.289 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9950 reflections
a = 29.2734 (18) Åθ = 2.3–25.4°
b = 10.2321 (6) ŵ = 11.98 mm1
c = 17.5643 (11) ÅT = 173 K
β = 106.483 (1)°Chunk, colourless
V = 5044.8 (5) Å30.32 × 0.13 × 0.06 mm
Z = 16
Data collection top
Bruker APEXII CCD
diffractometer
4651 independent reflections
Radiation source: fine-focus sealed tube4183 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
Detector resolution: 836.6 pixels mm-1θmax = 25.4°, θmin = 2.1°
ω,and/f 0.5 deg scansh = 3535
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
k = 1212
Tmin = 0.371, Tmax = 0.745l = 2121
18295 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.019Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.048H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0223P)2]
where P = (Fo2 + 2Fc2)/3
4651 reflections(Δ/σ)max = 0.004
291 parametersΔρmax = 0.74 e Å3
0 restraintsΔρmin = 0.63 e Å3
Crystal data top
[AuCl(C12H11OP)]V = 5044.8 (5) Å3
Mr = 434.59Z = 16
Monoclinic, C2/cMo Kα radiation
a = 29.2734 (18) ŵ = 11.98 mm1
b = 10.2321 (6) ÅT = 173 K
c = 17.5643 (11) Å0.32 × 0.13 × 0.06 mm
β = 106.483 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
4651 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
4183 reflections with I > 2σ(I)
Tmin = 0.371, Tmax = 0.745Rint = 0.036
18295 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0190 restraints
wR(F2) = 0.048H-atom parameters constrained
S = 1.03Δρmax = 0.74 e Å3
4651 reflectionsΔρmin = 0.63 e Å3
291 parameters
Special details top

Experimental. Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a glass fiber or nylon loop using Paratone oil for Mo radiation and Mineral oil for Copper radiation. Data were measured using omega and phi scans of 0.5° per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83Å to 100%. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structures are solved by the direct method using the SHELXS97 program and refined by least squares method on F2, SHELXL97, incorporated in SHELXTL-PC V 6.14. The crystal used for the diffraction study showed no decomposition during data collection.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Au10.960725 (5)0.437105 (13)0.289805 (8)0.02121 (5)
Au20.887378 (5)0.384820 (13)0.378563 (9)0.02700 (6)
Cl11.00671 (3)0.26698 (9)0.36128 (6)0.0284 (2)
Cl20.89312 (4)0.59742 (9)0.42511 (6)0.0368 (3)
P10.91703 (4)0.60110 (9)0.22307 (6)0.0228 (2)
P20.87692 (4)0.17285 (9)0.35069 (7)0.0268 (2)
O10.90588 (11)0.7154 (2)0.27649 (16)0.0342 (7)
H10.90590.68530.32100.051*
O20.91734 (10)0.0976 (3)0.3237 (2)0.0411 (8)
H20.94350.13630.34190.062*
C10.85968 (13)0.5459 (4)0.1619 (2)0.0241 (8)
C20.81825 (15)0.6080 (4)0.1658 (3)0.0372 (11)
H2B0.81980.67850.20160.045*
C30.77481 (17)0.5670 (5)0.1175 (3)0.0508 (13)
H30.74650.60950.12010.061*
C40.77226 (16)0.4651 (5)0.0657 (3)0.0471 (12)
H40.74230.43890.03160.056*
C50.81274 (17)0.4011 (5)0.0630 (3)0.0437 (11)
H50.81070.32940.02780.052*
C60.85684 (15)0.4403 (4)0.1113 (3)0.0347 (10)
H60.88490.39510.10960.042*
C70.94390 (13)0.6894 (3)0.1576 (2)0.0244 (8)
C80.95612 (14)0.6238 (4)0.0969 (2)0.0286 (9)
H80.94910.53340.08890.034*
C90.97805 (15)0.6877 (4)0.0485 (3)0.0378 (10)
H90.98620.64160.00730.045*
C100.98827 (15)0.8194 (5)0.0597 (3)0.0428 (12)
H101.00380.86380.02650.051*
C110.97600 (16)0.8859 (4)0.1187 (3)0.0434 (12)
H110.98270.97670.12560.052*
C120.95387 (14)0.8222 (4)0.1687 (3)0.0330 (10)
H120.94570.86870.20970.040*
C130.87130 (14)0.0853 (4)0.4367 (2)0.0269 (9)
C140.88671 (15)0.0425 (4)0.4518 (3)0.0345 (10)
H140.90100.08630.41670.041*
C150.88123 (17)0.1070 (4)0.5187 (3)0.0425 (12)
H150.89160.19500.52870.051*
C160.86084 (17)0.0442 (4)0.5704 (3)0.0405 (11)
H160.85740.08810.61610.049*
C170.84557 (16)0.0823 (4)0.5551 (3)0.0368 (10)
H170.83110.12530.59020.044*
C180.85078 (14)0.1480 (4)0.4900 (2)0.0298 (9)
H180.84050.23610.48100.036*
C190.82412 (14)0.1317 (4)0.2729 (2)0.0273 (9)
C200.81456 (16)0.0011 (4)0.2501 (3)0.0361 (10)
H200.83650.06550.27440.043*
C210.77345 (16)0.0307 (4)0.1926 (3)0.0407 (11)
H210.76730.11930.17690.049*
C220.74071 (16)0.0648 (4)0.1570 (3)0.0393 (11)
H220.71200.04190.11800.047*
C230.75038 (16)0.1929 (4)0.1789 (3)0.0430 (11)
H230.72830.25920.15490.052*
C240.79207 (16)0.2261 (4)0.2357 (3)0.0376 (10)
H240.79870.31540.24930.045*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.01960 (9)0.02248 (8)0.02120 (9)0.00212 (5)0.00521 (7)0.00271 (5)
Au20.02700 (10)0.02272 (9)0.03339 (10)0.00234 (6)0.01200 (7)0.00352 (6)
Cl10.0240 (5)0.0277 (5)0.0322 (5)0.0054 (4)0.0060 (4)0.0078 (4)
Cl20.0522 (7)0.0266 (5)0.0372 (6)0.0047 (5)0.0217 (5)0.0079 (4)
P10.0238 (6)0.0214 (5)0.0219 (5)0.0035 (4)0.0042 (4)0.0016 (4)
P20.0232 (6)0.0237 (5)0.0351 (6)0.0008 (4)0.0106 (5)0.0041 (4)
O10.0470 (19)0.0264 (14)0.0300 (17)0.0066 (13)0.0120 (15)0.0004 (12)
O20.0306 (18)0.0311 (15)0.067 (2)0.0012 (13)0.0237 (17)0.0126 (15)
C10.021 (2)0.029 (2)0.021 (2)0.0005 (16)0.0051 (17)0.0061 (16)
C20.023 (2)0.038 (2)0.050 (3)0.0052 (18)0.011 (2)0.002 (2)
C30.023 (3)0.057 (3)0.072 (4)0.009 (2)0.014 (3)0.000 (3)
C40.023 (3)0.061 (3)0.049 (3)0.004 (2)0.004 (2)0.009 (2)
C50.035 (3)0.053 (3)0.037 (3)0.004 (2)0.000 (2)0.005 (2)
C60.023 (2)0.042 (2)0.039 (3)0.0021 (18)0.008 (2)0.0097 (19)
C70.017 (2)0.0268 (19)0.024 (2)0.0019 (15)0.0030 (16)0.0059 (16)
C80.026 (2)0.031 (2)0.028 (2)0.0032 (17)0.0051 (18)0.0061 (17)
C90.033 (3)0.052 (3)0.026 (2)0.001 (2)0.0030 (19)0.013 (2)
C100.025 (3)0.057 (3)0.043 (3)0.007 (2)0.004 (2)0.021 (2)
C110.033 (3)0.035 (2)0.052 (3)0.013 (2)0.005 (2)0.009 (2)
C120.027 (2)0.028 (2)0.038 (3)0.0015 (17)0.0002 (19)0.0044 (18)
C130.021 (2)0.0249 (19)0.030 (2)0.0050 (16)0.0000 (17)0.0040 (17)
C140.032 (3)0.031 (2)0.036 (3)0.0003 (18)0.003 (2)0.0067 (18)
C150.053 (3)0.025 (2)0.040 (3)0.002 (2)0.002 (2)0.0035 (19)
C160.052 (3)0.035 (2)0.029 (3)0.010 (2)0.003 (2)0.0008 (19)
C170.044 (3)0.035 (2)0.032 (3)0.006 (2)0.012 (2)0.0046 (19)
C180.029 (2)0.0255 (19)0.033 (2)0.0002 (17)0.0047 (19)0.0011 (17)
C190.031 (2)0.028 (2)0.028 (2)0.0024 (17)0.0159 (19)0.0002 (16)
C200.036 (3)0.028 (2)0.041 (3)0.0002 (19)0.007 (2)0.0019 (19)
C210.043 (3)0.039 (2)0.040 (3)0.009 (2)0.012 (2)0.010 (2)
C220.029 (3)0.059 (3)0.029 (2)0.012 (2)0.006 (2)0.002 (2)
C230.035 (3)0.048 (3)0.041 (3)0.007 (2)0.003 (2)0.007 (2)
C240.040 (3)0.031 (2)0.042 (3)0.0003 (19)0.011 (2)0.0010 (19)
Geometric parameters (Å, º) top
Au1—P12.2304 (10)C9—C101.382 (6)
Au1—Cl12.3366 (9)C9—H90.9500
Au1—Au1i3.0112 (3)C10—C111.370 (7)
Au1—Au23.0375 (2)C10—H100.9500
Au2—P22.2254 (10)C11—C121.392 (6)
Au2—Cl22.3131 (10)C11—H110.9500
P1—O11.591 (3)C12—H120.9500
P1—C11.808 (4)C13—C141.385 (5)
P1—C71.808 (4)C13—C181.403 (5)
P2—O21.592 (3)C14—C151.396 (6)
P2—C191.799 (4)C14—H140.9500
P2—C131.803 (4)C15—C161.379 (6)
O1—H10.8400C15—H150.9500
O2—H20.8400C16—C171.371 (6)
C1—C21.387 (5)C16—H160.9500
C1—C61.387 (5)C17—C181.371 (6)
C2—C31.378 (6)C17—H170.9500
C2—H2B0.9500C18—H180.9500
C3—C41.372 (7)C19—C241.375 (6)
C3—H30.9500C19—C201.401 (5)
C4—C51.366 (6)C20—C211.373 (6)
C4—H40.9500C20—H200.9500
C5—C61.387 (6)C21—C221.387 (6)
C5—H50.9500C21—H210.9500
C6—H60.9500C22—C231.373 (6)
C7—C81.389 (5)C22—H220.9500
C7—C121.392 (5)C23—C241.381 (6)
C8—C91.368 (5)C23—H230.9500
C8—H80.9500C24—H240.9500
P1—Au1—Cl1179.23 (3)C8—C9—H9120.1
P1—Au1—Au1i98.95 (3)C10—C9—H9120.1
Cl1—Au1—Au1i81.37 (2)C11—C10—C9119.9 (4)
P1—Au1—Au291.08 (3)C11—C10—H10120.0
Cl1—Au1—Au288.65 (2)C9—C10—H10120.0
Au1i—Au1—Au2169.256 (4)C10—C11—C12120.9 (4)
P2—Au2—Cl2170.39 (4)C10—C11—H11119.5
P2—Au2—Au197.58 (3)C12—C11—H11119.5
Cl2—Au2—Au191.41 (3)C11—C12—C7119.1 (4)
O1—P1—C1105.59 (17)C11—C12—H12120.5
O1—P1—C7101.93 (16)C7—C12—H12120.5
C1—P1—C7106.06 (17)C14—C13—C18118.8 (4)
O1—P1—Au1115.24 (11)C14—C13—P2121.9 (3)
C1—P1—Au1112.00 (12)C18—C13—P2119.4 (3)
C7—P1—Au1114.96 (12)C13—C14—C15119.9 (4)
O2—P2—C19102.24 (18)C13—C14—H14120.0
O2—P2—C13105.13 (18)C15—C14—H14120.0
C19—P2—C13104.90 (17)C16—C15—C14120.5 (4)
O2—P2—Au2117.99 (11)C16—C15—H15119.7
C19—P2—Au2115.47 (13)C14—C15—H15119.7
C13—P2—Au2109.84 (13)C17—C16—C15119.3 (4)
P1—O1—H1109.5C17—C16—H16120.4
P2—O2—H2109.5C15—C16—H16120.4
C2—C1—C6119.6 (4)C16—C17—C18121.3 (4)
C2—C1—P1120.4 (3)C16—C17—H17119.4
C6—C1—P1120.1 (3)C18—C17—H17119.4
C3—C2—C1119.8 (4)C17—C18—C13120.2 (4)
C3—C2—H2B120.1C17—C18—H18119.9
C1—C2—H2B120.1C13—C18—H18119.9
C4—C3—C2120.4 (4)C24—C19—C20118.7 (4)
C4—C3—H3119.8C24—C19—P2121.3 (3)
C2—C3—H3119.8C20—C19—P2120.0 (3)
C5—C4—C3120.2 (4)C21—C20—C19119.9 (4)
C5—C4—H4119.9C21—C20—H20120.1
C3—C4—H4119.9C19—C20—H20120.1
C4—C5—C6120.4 (4)C20—C21—C22121.0 (4)
C4—C5—H5119.8C20—C21—H21119.5
C6—C5—H5119.8C22—C21—H21119.5
C1—C6—C5119.6 (4)C23—C22—C21119.0 (4)
C1—C6—H6120.2C23—C22—H22120.5
C5—C6—H6120.2C21—C22—H22120.5
C8—C7—C12119.3 (4)C22—C23—C24120.5 (4)
C8—C7—P1120.0 (3)C22—C23—H23119.8
C12—C7—P1120.7 (3)C24—C23—H23119.8
C9—C8—C7121.0 (4)C19—C24—C23120.9 (4)
C9—C8—H8119.5C19—C24—H24119.5
C7—C8—H8119.5C23—C24—H24119.5
C8—C9—C10119.9 (4)
P1—Au1—Au2—P2126.72 (4)C1—P1—C7—C12116.5 (3)
Cl1—Au1—Au2—P254.00 (4)Au1—P1—C7—C12119.1 (3)
Au1i—Au1—Au2—P232.28 (5)C12—C7—C8—C90.5 (6)
P1—Au1—Au2—Cl256.69 (4)P1—C7—C8—C9177.6 (3)
Cl1—Au1—Au2—Cl2122.59 (4)C7—C8—C9—C100.1 (6)
Au1i—Au1—Au2—Cl2144.31 (5)C8—C9—C10—C110.6 (7)
Cl1—Au1—P1—O111 (3)C9—C10—C11—C120.9 (7)
Au1i—Au1—P1—O1125.53 (13)C10—C11—C12—C70.5 (6)
Au2—Au1—P1—O158.35 (13)C8—C7—C12—C110.2 (6)
Cl1—Au1—P1—C1132 (3)P1—C7—C12—C11177.9 (3)
Au1i—Au1—P1—C1113.74 (13)O2—P2—C13—C1420.8 (4)
Au2—Au1—P1—C162.38 (14)C19—P2—C13—C1486.6 (4)
Cl1—Au1—P1—C7107 (3)Au2—P2—C13—C14148.7 (3)
Au1i—Au1—P1—C77.40 (14)O2—P2—C13—C18159.2 (3)
Au2—Au1—P1—C7176.48 (14)C19—P2—C13—C1893.4 (3)
Cl2—Au2—P2—O2139.1 (3)Au2—P2—C13—C1831.3 (3)
Au1—Au2—P2—O220.00 (16)C18—C13—C14—C150.6 (6)
Cl2—Au2—P2—C1999.6 (3)P2—C13—C14—C15179.4 (3)
Au1—Au2—P2—C19101.26 (14)C13—C14—C15—C160.4 (7)
Cl2—Au2—P2—C1318.8 (3)C14—C15—C16—C170.6 (7)
Au1—Au2—P2—C13140.40 (14)C15—C16—C17—C180.9 (7)
O1—P1—C1—C23.3 (4)C16—C17—C18—C131.1 (6)
C7—P1—C1—C2104.4 (3)C14—C13—C18—C171.0 (6)
Au1—P1—C1—C2129.4 (3)P2—C13—C18—C17179.0 (3)
O1—P1—C1—C6176.2 (3)O2—P2—C19—C24131.4 (3)
C7—P1—C1—C676.1 (4)C13—P2—C19—C24119.0 (3)
Au1—P1—C1—C650.0 (3)Au2—P2—C19—C242.0 (4)
C6—C1—C2—C32.0 (6)O2—P2—C19—C2049.7 (3)
P1—C1—C2—C3178.5 (4)C13—P2—C19—C2059.8 (4)
C1—C2—C3—C40.0 (7)Au2—P2—C19—C20179.2 (3)
C2—C3—C4—C51.7 (8)C24—C19—C20—C211.1 (6)
C3—C4—C5—C61.4 (7)P2—C19—C20—C21177.8 (3)
C2—C1—C6—C52.4 (6)C19—C20—C21—C220.7 (7)
P1—C1—C6—C5178.2 (3)C20—C21—C22—C231.3 (7)
C4—C5—C6—C10.7 (7)C21—C22—C23—C240.1 (7)
O1—P1—C7—C8175.6 (3)C20—C19—C24—C232.3 (6)
C1—P1—C7—C865.4 (3)P2—C19—C24—C23176.6 (3)
Au1—P1—C7—C859.0 (3)C22—C23—C24—C191.7 (7)
O1—P1—C7—C126.3 (4)
Symmetry code: (i) x+2, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···Cl20.842.162.994 (3)170
O2—H2···Cl10.842.233.050 (3)166

Experimental details

Crystal data
Chemical formula[AuCl(C12H11OP)]
Mr434.59
Crystal system, space groupMonoclinic, C2/c
Temperature (K)173
a, b, c (Å)29.2734 (18), 10.2321 (6), 17.5643 (11)
β (°) 106.483 (1)
V3)5044.8 (5)
Z16
Radiation typeMo Kα
µ (mm1)11.98
Crystal size (mm)0.32 × 0.13 × 0.06
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.371, 0.745
No. of measured, independent and
observed [I > 2σ(I)] reflections
18295, 4651, 4183
Rint0.036
(sin θ/λ)max1)0.603
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.019, 0.048, 1.03
No. of reflections4651
No. of parameters291
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.74, 0.63

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···Cl20.842.162.994 (3)169.9
O2—H2···Cl10.842.233.050 (3)165.5
 

Acknowledgements

WEvZ gratefully acknowledges financial support through a UKZN Competitive Grant, and also thanks Rand Refineries (South Africa) for a gift of the gold salt. SVS thanks the National Research Foundation (NRF) for an Innovative Grant.

References

First citationBraga, D. & Grepioni, F. (2007). Editors. Making Crystals by Design: Methods, Techniques and Applications. Weinheim: Wiley-VCH Verlag.  Google Scholar
First citationBruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationHealy, P. C. (2003). Acta Cryst. E59, m1112–m1114.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHollatz, C., Schier, A., Riede, J. & Schmidbaur, H. (1999). J. Chem. Soc., Dalton Trans. pp. 111–114.  Google Scholar
First citationHoshino, M., Uekusa, H., Ishii, S., Otsuka, T., Kaizu, Y., Ozawa, Y. & Toriumi, K. (2010). Inorg. Chem. 49, 7257–7265.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationVan Zyl, W. E. (2010). Comments Inorg. Chem. 31, 13–45.  Web of Science CrossRef CAS Google Scholar

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds