Chlorido[tris­(3-fluoro­phen­yl)phosphine]gold(I)

Shawkataly, O. bin; Tariq, A.; Ghani, S.S.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810034896

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages m1217-m1218

doi:10.1107/S1600536810034896

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Chlorido[tris(3-fluorophenyl)phosphine]gold(I)

Omar bin Shawkataly,^a ^*‡ Abu Tariq,^a Syed Sauban Ghani,^a Chin Sing Yeap ^b § and Hoong-Kun Fun ^b ¶

^aChemical Sciences Programme, School of Distance Education, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: omarsa@usm.my

(Received 18 August 2010; accepted 30 August 2010; online 8 September 2010)

In the title gold complex, [AuCl(C₁₈H₁₂F₃P)], 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, molecules are linked into a three-dimensional network by intermolecular 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_r = 548.66
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.025
wR(F²) = 0.084
S = 1.06
5912 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 1.25 e Å⁻³
Δρ_min = −0.87 e Å⁻³
Absolute structure: Flack (1983 ), 2522 Friedel pairs
Flack parameter: 0.010 (8)

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x-{\script{1\over 2}}, -y, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034896/fj2329sup1.cif

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

checkCIF report

Comment top

Gold complexes are well known for their medicinal (Tiekink, 2002) and catalytic activities (Dyadchenko, 1982). Phosphinegold(I) forms an important class of compounds of gold (Baenziger et al., 1976). Chloro[tris(perflourophenyl)phospine]gold(I) is a known complex which is conveniently prepared and characterized (Chen & Tiekink, 2003). Keeping in mind the importance of the phosphine gold complexes, we have prepared the title complex and reported the crystal structure of the title complex.

In the title compound (Fig. 1), the P1–Au1–Cl1 is linear with an angle of 178.13 (5)°. The three phosphine substituted benzene rings (C1–C6, C7–C12 and C13–C18) make dihedral angles of 77.7 (3), 84.4 (3) and 77.4 (3)° with each other (C1–C6/C7–C12, C1–C6/C13–C18 and C7–C12/C13–C18). In the crystal structure, the molecules are linked into a three-dimensional network by intermolecular C4—H4A···Cl1, C5—H5A···Cl1 and C10—H10A···F1 hydrogen bonds (Fig. 2, Table 1).

Related literature top

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 top

The title compound was prepared from the reaction between Me₂SAuCl (Francis, 1901) and (m-FC₆H₄)₃P (Maybridge) in a 1:1 molar ratio in CH₂Cl₂ at room temperature. Solution was stirred for two hours, solvent was removed under vacuum, and white crystalline solid was obtained. The colorless crystals were obtained in 90% yield from the concentrated solution of the compound (m.p. 193 °C, decomposition) in ethanol kept for few days at room temperature.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis, showing the molecules linked into a 3-D network. Hydrogen atoms that not involved in the hydrogen-bonding (dashed lines) have been omitted for clarity.

Chlorido[tris(3-fluorophenyl)phosphine]gold(I) top

Crystal data top

[AuCl(C₁₈H₁₂F₃P)]	F(000) = 1032
M_r = 548.66	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0362P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
5912 reflections	Δρ_max = 1.25 e Å⁻³
237 parameters	Δρ_min = −0.87 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2522 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.010 (8)

Crystal data top

[AuCl(C₁₈H₁₂F₃P)]	V = 1695.6 (2) Å³
M_r = 548.66	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.4028 (8) Å	µ = 8.95 mm⁻¹
b = 12.3281 (11) Å	T = 100 K
c = 13.2214 (10) Å	0.50 × 0.13 × 0.08 mm

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	5912 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5263 reflections with I > 2σ(I)
T_min = 0.094, T_max = 0.520	R_int = 0.031
14491 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	H-atom parameters constrained
wR(F²) = 0.084	Δρ_max = 1.25 e Å⁻³
S = 1.06	Δρ_min = −0.87 e Å⁻³
5912 reflections	Absolute structure: Flack (1983), 2522 Friedel pairs
237 parameters	Absolute structure parameter: 0.010 (8)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, −z+1; (ii) −x−1/2, −y, z+1/2; (iii) −x+1/2, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	[AuCl(C₁₈H₁₂F₃P)]
M_r	548.66
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	10.4028 (8), 12.3281 (11), 13.2214 (10)
V (Å³)	1695.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.95
Crystal size (mm)	0.50 × 0.13 × 0.08

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.094, 0.520
No. of measured, independent and observed [I > 2σ(I)] reflections	14491, 5912, 5263
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.084, 1.06
No. of reflections	5912
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.25, −0.87
Absolute structure	Flack (1983), 2522 Friedel pairs
Absolute structure parameter	0.010 (8)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, −z+1; (ii) −x−1/2, −y, z+1/2; (iii) −x+1/2, −y+1, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: B-6034-2009. On secondment to: Multimedia University, Melaka Campus, Jalan Ayer Keroh Lama, 74750 Melaka, Malaysia.

§Thomson Reuters ResearcherID: A-5523-2009.

¶Thomson Reuters ResearcherID: A-3561-2009. Additional correspondence author, e-mail: hkfun@usm.my.

Acknowledgements

The authors would like to thank the Malaysian Government and Universiti Sains Malaysia (USM) for the University Research Grant 1001/PJJAUH/811115. AT is grateful to USM for a Post-Doctoral Fellowship and HKF and CSY thank USM for the Research University Golden Goose Grant 1001/PFIZIK/811012. CSY also thanks USM for the award of a USM Fellowship.

References

Baenziger, N. C., Bennett, W. E. & Soborofe, D. M. (1976). Acta Cryst. B32, 962–963. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, H. W. & Tiekink, E. R. T. (2003). Acta Cryst. E59, m50–m52. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Dyadchenko, V. P. (1982). Russ. Chem. Rev. 51, 265–271. CrossRef Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Francis, C. P. (1901). J. Am. Chem. Soc. 23, 250–258. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tiekink, E. R. T. (2002). Crit. Rev. Oncol. Hematol. 42, 225–248. Web of Science CrossRef PubMed Google Scholar