(Benzyl-diphenyl-phosphane)chlorido-gold(I).

In the title compound, [AuCl(C(19)H(17)P)], the Au(I) atom exists within a P and Cl donor set that constitutes an almost linear geometry. The three phenyl rings make dihedral angles of 38.33 (14), 81.26 (15) and 81.28 (14)° with each other. In the crystal, mol-ecules are linked into chains along the b axis by inter-molecular C-H⋯Cl hydrogen bonds.

Related literature

For general background to gold complexes, see: Parish & Cottrill (1987 ▶); Tiekink (2002 ▶); Baenziger et al. (1976 ▶); Chiu et al. (2009 ▶). For the synthesis of (CH3)2SAuCl, see: Francis (1901 ▶). For a related structure, see: Shawkataly et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[AuCl(C19H17P)]

M = 508.71

Monoclinic,

a = 16.1403 (11) Å

b = 9.0380 (7) Å

c = 23.5259 (17) Å

β = 91.012 (2)°

V = 3431.3 (4) Å3

Z = 8

Mo Kα radiation

μ = 8.82 mm−1

T = 100 K

0.27 × 0.22 × 0.12 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.196, T max = 0.408

28002 measured reflections

7489 independent reflections

6751 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.053

S = 1.14

7489 reflections

199 parameters

H-atom parameters constrained

Δρmax = 1.43 e Å−3

Δρmin = −2.38 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045071/is2625sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045071/is2625Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[AuCl(C19H17P)]	F(000) = 1936
Mr = 508.71	Dx = 1.969 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9893 reflections
a = 16.1403 (11) Å	θ = 2.7–37.4°
b = 9.0380 (7) Å	µ = 8.82 mm−1
c = 23.5259 (17) Å	T = 100 K
β = 91.012 (2)°	Plate, colourless
V = 3431.3 (4) Å3	0.27 × 0.22 × 0.12 mm
Z = 8

Bruker APEXII DUO CCD area-detector diffractometer	7489 independent reflections
Radiation source: fine-focus sealed tube	6751 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 35.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→26
Tmin = 0.196, Tmax = 0.408	k = −7→14
28002 measured reflections	l = −37→37

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.053	H-atom parameters constrained
S = 1.14	w = 1/[σ2(Fo2) + (0.P)2 + 12.0783P] where P = (Fo2 + 2Fc2)/3
7489 reflections	(Δ/σ)max = 0.002
199 parameters	Δρmax = 1.43 e Å−3
0 restraints	Δρmin = −2.37 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
Au1	0.323189 (5)	0.699677 (10)	0.101304 (4)	0.01995 (3)
Cl1	0.31261 (4)	0.94885 (7)	0.08307 (3)	0.02787 (12)
P1	0.34216 (4)	0.45646 (7)	0.11042 (3)	0.01953 (11)
C1	0.11935 (17)	0.4585 (3)	0.08496 (12)	0.0293 (5)
H1A	0.1301	0.5168	0.0534	0.035*
C2	0.04361 (18)	0.4704 (4)	0.11189 (14)	0.0354 (6)
H2A	0.0039	0.5364	0.0980	0.042*
C3	0.02680 (18)	0.3854 (4)	0.15894 (14)	0.0367 (7)
H3A	−0.0241	0.3937	0.1766	0.044*
C4	0.08609 (19)	0.2873 (4)	0.17987 (14)	0.0353 (6)
H4A	0.0754	0.2306	0.2119	0.042*
C5	0.16161 (18)	0.2743 (3)	0.15271 (13)	0.0304 (5)
H5A	0.2010	0.2077	0.1665	0.036*
C6	0.17911 (15)	0.3596 (3)	0.10519 (11)	0.0243 (5)
C7	0.26100 (16)	0.3445 (3)	0.07589 (11)	0.0238 (4)
H7A	0.2545	0.3751	0.0365	0.029*
H7B	0.2777	0.2414	0.0762	0.029*
C8	0.34892 (14)	0.3852 (3)	0.18224 (10)	0.0210 (4)
C9	0.31074 (17)	0.4608 (3)	0.22617 (11)	0.0264 (5)
H9A	0.2867	0.5528	0.2195	0.032*
C10	0.3088 (2)	0.3977 (4)	0.27999 (12)	0.0334 (6)
H10A	0.2819	0.4465	0.3092	0.040*
C11	0.34654 (19)	0.2628 (4)	0.29046 (12)	0.0305 (5)
H11A	0.3461	0.2224	0.3268	0.037*
C12	0.38490 (18)	0.1881 (3)	0.24694 (13)	0.0313 (5)
H12A	0.4097	0.0969	0.2540	0.038*
C13	0.38647 (18)	0.2485 (3)	0.19300 (12)	0.0284 (5)
H13A	0.4125	0.1981	0.1638	0.034*
C14	0.43910 (15)	0.4021 (3)	0.07884 (10)	0.0208 (4)
C15	0.51087 (17)	0.4641 (4)	0.10215 (13)	0.0322 (6)
H15A	0.5074	0.5293	0.1326	0.039*
C16	0.58762 (17)	0.4292 (4)	0.08027 (13)	0.0305 (5)
H16A	0.6355	0.4708	0.0960	0.037*
C17	0.59297 (17)	0.3323 (3)	0.03495 (12)	0.0277 (5)
H17A	0.6445	0.3080	0.0205	0.033*
C18	0.52207 (19)	0.2721 (4)	0.01125 (13)	0.0349 (6)
H18A	0.5259	0.2081	−0.0196	0.042*
C19	0.44462 (17)	0.3060 (3)	0.03307 (12)	0.0296 (5)
H19A	0.3969	0.2645	0.0170	0.036*

	U11	U22	U33	U12	U13	U23
Au1	0.01950 (4)	0.01675 (4)	0.02361 (4)	0.00189 (3)	0.00046 (3)	−0.00088 (3)
Cl1	0.0251 (3)	0.0164 (2)	0.0422 (3)	0.0030 (2)	0.0035 (2)	0.0030 (2)
P1	0.0198 (2)	0.0172 (3)	0.0215 (3)	0.0010 (2)	−0.0013 (2)	−0.0018 (2)
C1	0.0257 (11)	0.0302 (13)	0.0317 (13)	0.0055 (10)	−0.0051 (10)	−0.0069 (10)
C2	0.0240 (12)	0.0407 (17)	0.0414 (16)	0.0082 (11)	−0.0059 (11)	−0.0109 (13)
C3	0.0254 (12)	0.0434 (18)	0.0412 (16)	−0.0034 (12)	0.0006 (11)	−0.0158 (13)
C4	0.0312 (13)	0.0360 (16)	0.0387 (15)	−0.0118 (12)	0.0010 (11)	−0.0027 (12)
C5	0.0278 (12)	0.0252 (13)	0.0381 (14)	−0.0022 (10)	−0.0032 (10)	0.0006 (10)
C6	0.0218 (10)	0.0208 (11)	0.0302 (12)	−0.0006 (8)	−0.0048 (9)	−0.0058 (9)
C7	0.0251 (10)	0.0199 (10)	0.0262 (11)	0.0007 (9)	−0.0040 (9)	−0.0037 (8)
C8	0.0201 (9)	0.0202 (10)	0.0228 (10)	0.0004 (8)	−0.0015 (8)	0.0001 (8)
C9	0.0300 (12)	0.0212 (11)	0.0279 (12)	0.0021 (9)	0.0018 (9)	−0.0007 (9)
C10	0.0443 (16)	0.0291 (13)	0.0270 (12)	−0.0017 (12)	0.0070 (11)	−0.0016 (10)
C11	0.0350 (13)	0.0309 (14)	0.0255 (12)	−0.0053 (11)	0.0000 (10)	0.0042 (10)
C12	0.0322 (13)	0.0298 (14)	0.0319 (13)	0.0053 (11)	0.0004 (10)	0.0087 (11)
C13	0.0309 (12)	0.0258 (12)	0.0287 (12)	0.0081 (10)	0.0022 (10)	0.0035 (10)
C14	0.0217 (9)	0.0188 (10)	0.0219 (10)	0.0041 (8)	−0.0011 (8)	0.0012 (8)
C15	0.0241 (11)	0.0358 (15)	0.0367 (14)	0.0007 (11)	−0.0008 (10)	−0.0128 (12)
C16	0.0221 (11)	0.0350 (15)	0.0343 (13)	0.0024 (10)	−0.0021 (10)	−0.0026 (11)
C17	0.0251 (11)	0.0327 (14)	0.0253 (11)	0.0041 (10)	0.0036 (9)	0.0037 (10)
C18	0.0314 (13)	0.0429 (18)	0.0305 (13)	0.0014 (12)	0.0055 (11)	−0.0118 (12)
C19	0.0271 (11)	0.0351 (14)	0.0266 (12)	0.0002 (11)	0.0002 (9)	−0.0081 (11)

Au1—P1	2.2292 (7)	C9—C10	1.389 (4)
Au1—Cl1	2.2983 (7)	C9—H9A	0.9300
P1—C8	1.810 (3)	C10—C11	1.383 (5)
P1—C14	1.812 (2)	C10—H10A	0.9300
P1—C7	1.834 (3)	C11—C12	1.382 (4)
C1—C2	1.391 (4)	C11—H11A	0.9300
C1—C6	1.393 (4)	C12—C13	1.382 (4)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.379 (5)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C19	1.387 (4)
C3—C4	1.388 (5)	C14—C15	1.391 (4)
C3—H3A	0.9300	C15—C16	1.386 (4)
C4—C5	1.391 (4)	C15—H15A	0.9300
C4—H4A	0.9300	C16—C17	1.383 (4)
C5—C6	1.391 (4)	C16—H16A	0.9300
C5—H5A	0.9300	C17—C18	1.376 (4)
C6—C7	1.508 (4)	C17—H17A	0.9300
C7—H7A	0.9700	C18—C19	1.394 (4)
C7—H7B	0.9700	C18—H18A	0.9300
C8—C9	1.391 (4)	C19—H19A	0.9300
C8—C13	1.398 (4)
P1—Au1—Cl1	173.62 (2)	C10—C9—C8	119.6 (3)
C8—P1—C14	104.37 (11)	C10—C9—H9A	120.2
C8—P1—C7	104.37 (12)	C8—C9—H9A	120.2
C14—P1—C7	106.50 (12)	C11—C10—C9	120.4 (3)
C8—P1—Au1	116.52 (8)	C11—C10—H10A	119.8
C14—P1—Au1	110.26 (8)	C9—C10—H10A	119.8
C7—P1—Au1	113.94 (9)	C12—C11—C10	120.0 (3)
C2—C1—C6	120.2 (3)	C12—C11—H11A	120.0
C2—C1—H1A	119.9	C10—C11—H11A	120.0
C6—C1—H1A	119.9	C13—C12—C11	120.2 (3)
C3—C2—C1	120.6 (3)	C13—C12—H12A	119.9
C3—C2—H2A	119.7	C11—C12—H12A	119.9
C1—C2—H2A	119.7	C12—C13—C8	120.0 (3)
C2—C3—C4	119.8 (3)	C12—C13—H13A	120.0
C2—C3—H3A	120.1	C8—C13—H13A	120.0
C4—C3—H3A	120.1	C19—C14—C15	119.6 (2)
C3—C4—C5	119.7 (3)	C19—C14—P1	123.8 (2)
C3—C4—H4A	120.2	C15—C14—P1	116.63 (19)
C5—C4—H4A	120.2	C16—C15—C14	120.4 (3)
C6—C5—C4	120.9 (3)	C16—C15—H15A	119.8
C6—C5—H5A	119.5	C14—C15—H15A	119.8
C4—C5—H5A	119.5	C17—C16—C15	119.9 (3)
C5—C6—C1	118.8 (3)	C17—C16—H16A	120.0
C5—C6—C7	120.6 (2)	C15—C16—H16A	120.0
C1—C6—C7	120.6 (3)	C18—C17—C16	120.0 (3)
C6—C7—P1	111.89 (17)	C18—C17—H17A	120.0
C6—C7—H7A	109.2	C16—C17—H17A	120.0
P1—C7—H7A	109.2	C17—C18—C19	120.6 (3)
C6—C7—H7B	109.2	C17—C18—H18A	119.7
P1—C7—H7B	109.2	C19—C18—H18A	119.7
H7A—C7—H7B	107.9	C14—C19—C18	119.6 (3)
C9—C8—C13	119.7 (2)	C14—C19—H19A	120.2
C9—C8—P1	119.93 (19)	C18—C19—H19A	120.2
C13—C8—P1	120.16 (19)
C6—C1—C2—C3	0.3 (5)	C8—C9—C10—C11	1.9 (5)
C1—C2—C3—C4	0.3 (5)	C9—C10—C11—C12	−1.5 (5)
C2—C3—C4—C5	−0.8 (5)	C10—C11—C12—C13	0.7 (5)
C3—C4—C5—C6	0.8 (5)	C11—C12—C13—C8	−0.3 (5)
C4—C5—C6—C1	−0.2 (4)	C9—C8—C13—C12	0.6 (4)
C4—C5—C6—C7	−179.8 (3)	P1—C8—C13—C12	−174.1 (2)
C2—C1—C6—C5	−0.4 (4)	C8—P1—C14—C19	116.6 (2)
C2—C1—C6—C7	179.3 (3)	C7—P1—C14—C19	6.5 (3)
C5—C6—C7—P1	−83.8 (3)	Au1—P1—C14—C19	−117.6 (2)
C1—C6—C7—P1	96.6 (3)	C8—P1—C14—C15	−64.5 (2)
C8—P1—C7—C6	60.1 (2)	C7—P1—C14—C15	−174.6 (2)
C14—P1—C7—C6	170.15 (18)	Au1—P1—C14—C15	61.3 (2)
Au1—P1—C7—C6	−68.1 (2)	C19—C14—C15—C16	−0.6 (5)
C14—P1—C8—C9	147.9 (2)	P1—C14—C15—C16	−179.6 (2)
C7—P1—C8—C9	−100.5 (2)	C14—C15—C16—C17	0.1 (5)
Au1—P1—C8—C9	26.0 (2)	C15—C16—C17—C18	0.7 (5)
C14—P1—C8—C13	−37.4 (2)	C16—C17—C18—C19	−0.9 (5)
C7—P1—C8—C13	74.2 (2)	C15—C14—C19—C18	0.4 (4)
Au1—P1—C8—C13	−159.25 (19)	P1—C14—C19—C18	179.2 (2)
C13—C8—C9—C10	−1.4 (4)	C17—C18—C19—C14	0.4 (5)
P1—C8—C9—C10	173.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···Cl1i	0.97	2.71	3.675 (3)	175

Au1—P1	2.2292 (7)
Au1—Cl1	2.2983 (7)

P1—Au1—Cl1

173.62 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯Cl1i	0.97	2.71	3.675 (3)	175

Symmetry code: (i) .