Chlorido[tris-(3-fluoro-phen-yl)phosphine]gold(I).

In the title gold complex, [AuCl(C(18)H(12)F(3)P)], the P-Au-Cl unit is nearly linear, with an angle of 178.13 (5)°. The three phosphine-substituted benzene rings make dihedral angles of 77.7 (3), 84.4 (3) and 77.4 (3)° with each other. Two of the three F atoms are disordered over two positions, with refined site occupancies of 0.591 (11):0.409 (11) and 0.730 (12):0.270 (12). In the crystal structure, mol-ecules are linked into a three-dimensional network by inter-molecular C-H⋯Cl and C-H⋯F hydrogen bonds.

Related literature

For general background to gold complex derivatives, see: Tiekink (2002 ▶); Dyadchenko (1982 ▶); Baenziger et al. (1976 ▶); Chen & Tiekink (2003 ▶). For the synthesis, see: Francis (1901 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[AuCl(C18H12F3P)]

M = 548.66

Orthorhombic,

a = 10.4028 (8) Å

b = 12.3281 (11) Å

c = 13.2214 (10) Å

V = 1695.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 8.95 mm−1

T = 100 K

0.50 × 0.13 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.094, T max = 0.520

14491 measured reflections

5912 independent reflections

5263 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.084

S = 1.06

5912 reflections

237 parameters

H-atom parameters constrained

Δρmax = 1.25 e Å−3

Δρmin = −0.87 e Å−3

Absolute structure: Flack (1983 ▶), 2522 Friedel pairs

Flack parameter: 0.010 (8)

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/S1600536810034896/fj2329sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034896/fj2329Isup2.hkl

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

[AuCl(C18H12F3P)]	F(000) = 1032
Mr = 548.66	Dx = 2.149 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7065 reflections
a = 10.4028 (8) Å	θ = 3.0–34.8°
b = 12.3281 (11) Å	µ = 8.95 mm−1
c = 13.2214 (10) Å	T = 100 K
V = 1695.6 (2) Å3	Block, colourless
Z = 4	0.50 × 0.13 × 0.08 mm

Bruker APEXII DUO CCD area-detector diffractometer	5912 independent reflections
Radiation source: fine-focus sealed tube	5263 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 32.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.094, Tmax = 0.520	k = −18→18
14491 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H-atom parameters constrained
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0362P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
5912 reflections	Δρmax = 1.25 e Å−3
237 parameters	Δρmin = −0.87 e Å−3
0 restraints	Absolute structure: Flack (1983), 2522 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.010 (8)

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	Occ. (<1)
Au1	−0.172736 (12)	0.064703 (12)	0.248330 (12)	0.02814 (5)
Cl1	−0.37503 (10)	0.00469 (13)	0.21314 (9)	0.0430 (3)
P1	0.02323 (11)	0.12844 (9)	0.28033 (8)	0.02683 (19)
F1	0.1479 (5)	0.4535 (3)	0.5012 (3)	0.0647 (11)
F2A	0.3891 (5)	0.3156 (6)	0.0912 (4)	0.0506 (19)	0.591 (11)
F3A	0.3834 (5)	−0.0758 (4)	0.4689 (4)	0.0577 (17)	0.730 (12)
F2B	−0.0532 (9)	0.3838 (8)	−0.0232 (7)	0.057 (3)	0.409 (11)
F3B	0.2739 (12)	−0.1835 (13)	0.1292 (11)	0.058 (5)	0.270 (12)
C1	0.0268 (5)	0.2072 (4)	0.3955 (3)	0.0314 (8)
C2	0.0940 (5)	0.3051 (4)	0.4037 (4)	0.0339 (9)
H2A	0.1430	0.3313	0.3502	0.041*
C3	0.0859 (6)	0.3613 (5)	0.4928 (4)	0.0415 (11)
C4	0.0171 (5)	0.3264 (5)	0.5753 (4)	0.0403 (11)
H4A	0.0139	0.3670	0.6345	0.048*
C5	−0.0473 (7)	0.2285 (6)	0.5669 (4)	0.0503 (14)
H5A	−0.0916	0.2009	0.6222	0.060*
C6	−0.0460 (5)	0.1720 (6)	0.4773 (4)	0.0423 (12)
H6A	−0.0948	0.1091	0.4713	0.051*
C7	0.0838 (4)	0.2165 (4)	0.1821 (3)	0.0292 (8)
C8	0.2166 (5)	0.2331 (4)	0.1705 (4)	0.0369 (10)
H8A	0.2759	0.1980	0.2118	0.044*
C9	0.2563 (5)	0.3051 (5)	0.0936 (4)	0.0412 (11)
H9A	0.3436	0.3195	0.0863	0.049*	0.409 (11)
C10	0.1742 (7)	0.3530 (5)	0.0314 (4)	0.0493 (15)
H10A	0.2039	0.3980	−0.0199	0.059*
C11	0.0419 (6)	0.3350 (4)	0.0439 (4)	0.0398 (11)
H11A	−0.0164	0.3693	0.0012	0.048*	0.591 (11)
C12	−0.0014 (4)	0.2683 (4)	0.1172 (4)	0.0362 (10)
H12A	−0.0893	0.2569	0.1244	0.043*
C13	0.1464 (4)	0.0259 (4)	0.2926 (3)	0.0308 (8)
C14	0.2201 (5)	0.0134 (4)	0.3816 (4)	0.0360 (10)
H14A	0.2075	0.0577	0.4377	0.043*
C15	0.3122 (5)	−0.0682 (5)	0.3812 (4)	0.0434 (12)
H15A	0.3621	−0.0769	0.4390	0.052*	0.270 (12)
C16	0.3342 (5)	−0.1358 (5)	0.3023 (5)	0.0448 (12)
H16A	0.3983	−0.1883	0.3057	0.054*
C17	0.2581 (5)	−0.1250 (5)	0.2156 (5)	0.0428 (11)
H17A	0.2706	−0.1714	0.1610	0.051*	0.730 (12)
C18	0.1647 (5)	−0.0455 (5)	0.2107 (4)	0.0377 (10)
H18A	0.1138	−0.0392	0.1532	0.045*

	U11	U22	U33	U12	U13	U23
Au1	0.02793 (7)	0.02848 (8)	0.02799 (7)	−0.00558 (5)	0.00235 (8)	−0.00385 (9)
Cl1	0.0336 (5)	0.0533 (7)	0.0421 (5)	−0.0160 (5)	0.0050 (4)	−0.0161 (6)
P1	0.0275 (4)	0.0269 (5)	0.0262 (4)	−0.0036 (4)	0.0003 (4)	−0.0018 (4)
F1	0.091 (3)	0.047 (2)	0.0557 (19)	−0.034 (2)	0.014 (2)	−0.0163 (18)
F2A	0.048 (3)	0.053 (4)	0.051 (3)	−0.020 (3)	0.014 (2)	−0.004 (3)
F3A	0.067 (4)	0.045 (3)	0.061 (3)	0.003 (2)	−0.026 (3)	0.004 (2)
F2B	0.062 (6)	0.058 (6)	0.050 (5)	0.017 (5)	0.006 (4)	0.036 (4)
F3B	0.050 (7)	0.061 (9)	0.064 (8)	0.020 (6)	−0.001 (6)	−0.043 (8)
C1	0.0306 (17)	0.034 (2)	0.0297 (18)	0.0007 (19)	−0.0011 (16)	−0.0077 (17)
C2	0.044 (2)	0.027 (2)	0.0308 (19)	−0.004 (2)	0.0000 (17)	0.0008 (19)
C3	0.049 (3)	0.035 (3)	0.040 (2)	−0.006 (2)	−0.006 (2)	−0.005 (2)
C4	0.045 (2)	0.042 (3)	0.034 (2)	0.006 (2)	−0.0003 (19)	−0.010 (2)
C5	0.055 (3)	0.062 (4)	0.034 (2)	−0.005 (3)	0.006 (2)	−0.010 (3)
C6	0.042 (3)	0.052 (3)	0.032 (2)	−0.011 (2)	0.0030 (19)	−0.002 (2)
C7	0.0319 (18)	0.030 (2)	0.0260 (17)	−0.0060 (16)	0.0048 (14)	−0.0041 (16)
C8	0.034 (2)	0.038 (2)	0.039 (2)	−0.009 (2)	0.0085 (18)	−0.002 (2)
C9	0.046 (3)	0.042 (3)	0.036 (2)	−0.014 (2)	0.0097 (19)	−0.005 (2)
C10	0.067 (4)	0.044 (3)	0.036 (2)	−0.025 (3)	0.020 (2)	−0.012 (2)
C11	0.057 (3)	0.030 (2)	0.033 (2)	−0.001 (2)	0.003 (2)	0.0019 (19)
C12	0.039 (3)	0.033 (2)	0.037 (2)	−0.0033 (19)	0.0061 (17)	−0.002 (2)
C13	0.0290 (17)	0.030 (2)	0.0330 (19)	−0.0024 (16)	0.0018 (15)	0.0014 (17)
C14	0.037 (2)	0.032 (2)	0.039 (2)	−0.0041 (19)	−0.0041 (18)	−0.003 (2)
C15	0.037 (2)	0.045 (3)	0.048 (3)	−0.005 (2)	−0.011 (2)	0.011 (2)
C16	0.034 (2)	0.036 (3)	0.065 (3)	0.005 (2)	0.001 (2)	0.009 (3)
C17	0.040 (2)	0.039 (3)	0.050 (3)	−0.002 (2)	0.005 (2)	−0.013 (2)
C18	0.036 (2)	0.043 (3)	0.035 (2)	0.001 (2)	0.0001 (17)	0.001 (2)

Au1—P1	2.2254 (11)	C7—C8	1.405 (6)
Au1—Cl1	2.2787 (11)	C8—C9	1.412 (7)
P1—C1	1.806 (4)	C8—H8A	0.9300
P1—C7	1.807 (5)	C9—C10	1.324 (9)
P1—C13	1.807 (5)	C9—H9A	0.9300
F1—C3	1.312 (7)	C10—C11	1.404 (9)
F2A—C9	1.387 (8)	C10—H10A	0.9300
F3A—C15	1.379 (7)	C11—C12	1.348 (7)
F2B—C11	1.458 (10)	C11—H11A	0.9300
F3B—C17	1.360 (12)	C12—H12A	0.9300
C1—C6	1.390 (7)	C13—C18	1.409 (7)
C1—C2	1.399 (7)	C13—C14	1.413 (7)
C2—C3	1.369 (7)	C14—C15	1.389 (8)
C2—H2A	0.9300	C14—H14A	0.9300
C3—C4	1.373 (8)	C15—C16	1.355 (9)
C4—C5	1.385 (9)	C15—H15A	0.9300
C4—H4A	0.9300	C16—C17	1.399 (9)
C5—C6	1.375 (8)	C16—H16A	0.9300
C5—H5A	0.9300	C17—C18	1.381 (8)
C6—H6A	0.9300	C17—H17A	0.9300
C7—C12	1.390 (7)	C18—H18A	0.9300
P1—Au1—Cl1	178.13 (5)	C8—C9—H9A	118.7
C1—P1—C7	106.0 (2)	C9—C10—C11	119.3 (5)
C1—P1—C13	106.6 (2)	C9—C10—H10A	120.3
C7—P1—C13	103.7 (2)	C11—C10—H10A	120.3
C1—P1—Au1	111.66 (16)	C12—C11—C10	120.5 (6)
C7—P1—Au1	113.28 (15)	C12—C11—F2B	117.5 (6)
C13—P1—Au1	114.81 (15)	C10—C11—F2B	121.9 (6)
C6—C1—C2	118.8 (5)	C12—C11—H11A	119.7
C6—C1—P1	118.4 (4)	C10—C11—H11A	119.7
C2—C1—P1	122.7 (4)	C11—C12—C7	120.7 (5)
C3—C2—C1	118.2 (5)	C11—C12—H12A	119.6
C3—C2—H2A	120.9	C7—C12—H12A	119.6
C1—C2—H2A	120.9	C18—C13—C14	119.9 (4)
F1—C3—C2	118.7 (5)	C18—C13—P1	117.7 (3)
F1—C3—C4	117.4 (5)	C14—C13—P1	122.4 (4)
C2—C3—C4	123.9 (5)	C15—C14—C13	116.8 (5)
C3—C4—C5	117.4 (5)	C15—C14—H14A	121.6
C3—C4—H4A	121.3	C13—C14—H14A	121.6
C5—C4—H4A	121.3	C16—C15—F3A	121.0 (5)
C6—C5—C4	120.5 (6)	C16—C15—C14	124.4 (5)
C6—C5—H5A	119.8	F3A—C15—C14	114.7 (6)
C4—C5—H5A	119.8	C16—C15—H15A	117.8
C5—C6—C1	121.1 (6)	C14—C15—H15A	117.8
C5—C6—H6A	119.4	C15—C16—C17	118.5 (5)
C1—C6—H6A	119.4	C15—C16—H16A	120.8
C12—C7—C8	119.6 (4)	C17—C16—H16A	120.8
C12—C7—P1	119.8 (3)	F3B—C17—C18	114.9 (8)
C8—C7—P1	120.6 (4)	F3B—C17—C16	124.7 (8)
C7—C8—C9	117.2 (5)	C18—C17—C16	120.3 (5)
C7—C8—H8A	121.4	C18—C17—H17A	119.9
C9—C8—H8A	121.4	C16—C17—H17A	119.9
C10—C9—F2A	125.9 (6)	C17—C18—C13	120.1 (5)
C10—C9—C8	122.6 (5)	C17—C18—H18A	119.9
F2A—C9—C8	111.5 (6)	C13—C18—H18A	119.9
C10—C9—H9A	118.7
C7—P1—C1—C6	162.5 (4)	F2A—C9—C10—C11	−179.5 (6)
C13—P1—C1—C6	−87.4 (5)	C8—C9—C10—C11	2.2 (9)
Au1—P1—C1—C6	38.7 (5)	C9—C10—C11—C12	−1.1 (9)
C7—P1—C1—C2	−13.8 (5)	C9—C10—C11—F2B	−178.9 (7)
C13—P1—C1—C2	96.2 (4)	C10—C11—C12—C7	0.3 (8)
Au1—P1—C1—C2	−137.6 (4)	F2B—C11—C12—C7	178.2 (6)
C6—C1—C2—C3	0.7 (8)	C8—C7—C12—C11	−0.6 (8)
P1—C1—C2—C3	177.0 (4)	P1—C7—C12—C11	179.5 (4)
C1—C2—C3—F1	−179.6 (5)	C1—P1—C13—C18	−178.8 (4)
C1—C2—C3—C4	1.0 (9)	C7—P1—C13—C18	−67.1 (4)
F1—C3—C4—C5	−179.3 (6)	Au1—P1—C13—C18	57.0 (4)
C2—C3—C4—C5	0.0 (9)	C1—P1—C13—C14	3.4 (5)
C3—C4—C5—C6	−2.9 (10)	C7—P1—C13—C14	115.1 (4)
C4—C5—C6—C1	4.6 (10)	Au1—P1—C13—C14	−120.8 (4)
C2—C1—C6—C5	−3.5 (9)	C18—C13—C14—C15	2.6 (7)
P1—C1—C6—C5	−180.0 (5)	P1—C13—C14—C15	−179.7 (4)
C1—P1—C7—C12	−100.3 (4)	C13—C14—C15—C16	−0.6 (8)
C13—P1—C7—C12	147.6 (4)	C13—C14—C15—F3A	178.7 (5)
Au1—P1—C7—C12	22.4 (4)	F3A—C15—C16—C17	179.5 (5)
C1—P1—C7—C8	79.8 (4)	C14—C15—C16—C17	−1.2 (8)
C13—P1—C7—C8	−32.3 (5)	C15—C16—C17—F3B	176.5 (10)
Au1—P1—C7—C8	−157.4 (4)	C15—C16—C17—C18	1.2 (8)
C12—C7—C8—C9	1.6 (7)	F3B—C17—C18—C13	−175.0 (9)
P1—C7—C8—C9	−178.5 (4)	C16—C17—C18—C13	0.8 (8)
C7—C8—C9—C10	−2.5 (8)	C14—C13—C18—C17	−2.7 (7)
C7—C8—C9—F2A	179.0 (5)	P1—C13—C18—C17	179.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···Cl1i	0.93	2.81	3.663 (6)	153
C5—H5A···Cl1ii	0.93	2.83	3.558 (7)	136
C10—H10A···F1iii	0.93	2.41	3.046 (8)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯Cl1i	0.93	2.81	3.663 (6)	153
C5—H5A⋯Cl1ii	0.93	2.83	3.558 (7)	136
C10—H10A⋯F1iii	0.93	2.41	3.046 (8)	126

Symmetry codes: (i) ; (ii) ; (iii) .