Chlorido{[(E)-2-(diphenyl-phosphan-yl)benzyl-idene](furan-2-ylmeth-yl)amine-κP}gold(I).

In the title complex, [AuCl(C24H20NOP)], the ligand has N, P and O electron-donating atoms but the Au(I) atom is coordinated only by the 'soft' P atom and an additional Cl atom in an almost linear fashion. Important geometrical parameters include Au-P = 2.2321 (13) Å, Au-Cl = 2.2820 (13) Å and P-Au-Cl = 176.49 (5)°. The furan ring is disordered over two positions in a 0.51 (2):0.49 (2) ratio.

Related literature

For general background to the title compound, see: Shaw (1999 ▶); Barnard et al. (2004 ▶); Nomiya et al. (2003 ▶). For the synthesis of the starting materials, see: Mogorosi et al. (2011 ▶); Uson & Laguna (1986 ▶). For similar compounds, see: Chiririwa & Muller (2012 ▶); Williams et al. (2007 ▶). For their applications, see: Chiririwa et al. (2013 ▶).

Experimental

Crystal data

[AuCl(C24H20NOP)]

M = 601.80

Monoclinic,

a = 13.4559 (4) Å

b = 10.3917 (2) Å

c = 17.2641 (4) Å

β = 111.751 (1)°

V = 2242.16 (9) Å3

Z = 4

Mo Kα radiation

μ = 6.77 mm−1

T = 173 K

0.16 × 0.11 × 0.02 mm

Data collection

Bruker APEXII 4K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.411, T max = 0.877

74340 measured reflections

5536 independent reflections

4175 reflections with I > 2σ(I)

R int = 0.100

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.07

5536 reflections

299 parameters

240 restraints

H-atom parameters constrained

Δρmax = 2.27 e Å−3

Δρmin = −1.52 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT and XPREP (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012) ▶.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050404/yk2081sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050404/yk2081Isup2.hkl

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

[AuCl(C24H20NOP)]	F(000) = 1160
Mr = 601.80	Dx = 1.783 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5534 reflections
a = 13.4559 (4) Å	θ = 3.6–28.3°
b = 10.3917 (2) Å	µ = 6.77 mm−1
c = 17.2641 (4) Å	T = 173 K
β = 111.751 (1)°	Plate, yellow
V = 2242.16 (9) Å3	0.16 × 0.11 × 0.02 mm
Z = 4

Bruker APEXII 4K CCD diffractometer	5536 independent reflections
Radiation source: fine-focus sealed tube	4175 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.100
Detector resolution: 0 pixels mm-1	θmax = 28.3°, θmin = 3.1°
0.5° ω scans, 20s	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2007)	k = −13→13
Tmin = 0.411, Tmax = 0.877	l = −23→23
74340 measured reflections

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) = 0.100	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0574P)2] where P = (Fo2 + 2Fc2)/3
5536 reflections	(Δ/σ)max = 0.003
299 parameters	Δρmax = 2.27 e Å−3
240 restraints	Δρmin = −1.52 e Å−3

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)
Cl1	0.67118 (12)	−0.07954 (12)	0.82704 (9)	0.0504 (3)
Au2	0.537496 (15)	0.068557 (17)	0.801052 (11)	0.03605 (9)
P3	0.40775 (10)	0.21597 (12)	0.76820 (7)	0.0330 (3)
C4	0.3211 (4)	0.1963 (5)	0.8271 (3)	0.0402 (11)
C5	0.2133 (4)	0.2276 (6)	0.7948 (4)	0.0525 (14)
H5	0.1813	0.2570	0.7389	0.063*
C6	0.1517 (6)	0.2161 (7)	0.8440 (5)	0.0707 (19)
H6	0.0775	0.2361	0.8213	0.085*
C7	0.1992 (7)	0.1753 (6)	0.9262 (5)	0.075 (2)
H7	0.1576	0.1680	0.9600	0.090*
C8	0.3059 (7)	0.1456 (6)	0.9584 (4)	0.0696 (19)
H8	0.3384	0.1187	1.0148	0.084*
C9	0.3670 (5)	0.1546 (5)	0.9092 (3)	0.0543 (14)
H9	0.4406	0.1320	0.9318	0.065*
C10	0.3191 (4)	0.2085 (5)	0.6596 (3)	0.0342 (10)
C11	0.2655 (4)	0.3144 (5)	0.6159 (3)	0.0477 (13)
H11	0.2723	0.3954	0.6429	0.057*
C12	0.2017 (5)	0.3020 (6)	0.5326 (4)	0.0626 (17)
H12	0.1644	0.3750	0.5026	0.075*
C13	0.1913 (5)	0.1858 (6)	0.4923 (3)	0.0588 (16)
H13	0.1469	0.1788	0.4350	0.071*
C14	0.2447 (5)	0.0805 (6)	0.5347 (4)	0.0561 (16)
H14	0.2395	0.0006	0.5068	0.067*
C15	0.3072 (4)	0.0910 (5)	0.6195 (3)	0.0436 (12)
H15	0.3418	0.0169	0.6499	0.052*
C16	0.4594 (4)	0.3787 (5)	0.7951 (3)	0.0326 (10)
C17	0.4287 (4)	0.4506 (4)	0.8500 (3)	0.0373 (11)
H17	0.3743	0.4178	0.8672	0.045*
C18	0.4745 (5)	0.5690 (4)	0.8810 (4)	0.0463 (13)
H18	0.4517	0.6157	0.9187	0.056*
C19	0.5530 (5)	0.6175 (5)	0.8564 (4)	0.0522 (14)
H19	0.5860	0.6974	0.8778	0.063*
C20	0.5835 (5)	0.5500 (5)	0.8009 (4)	0.0499 (14)
H20	0.6372	0.5856	0.7839	0.060*
C21	0.5394 (4)	0.4311 (4)	0.7681 (3)	0.0392 (11)
C22	0.5774 (4)	0.3688 (6)	0.7093 (3)	0.0458 (12)
H22	0.6342	0.4075	0.6977	0.055*
N23	0.5382 (3)	0.2656 (4)	0.6732 (3)	0.0441 (10)
C24	0.5800 (5)	0.2119 (7)	0.6128 (4)	0.0604 (16)
H24A	0.5925	0.1184	0.6225	0.072*
H24B	0.6490	0.2533	0.6197	0.072*
C25	0.5007 (5)	0.2348 (6)	0.5259 (4)	0.0577 (15)
C26	0.478 (2)	0.354 (2)	0.5111 (14)	0.069 (4)	0.51 (2)
H26	0.5032	0.4279	0.5455	0.082*	0.51 (2)
C27	0.4039 (18)	0.344 (2)	0.4285 (13)	0.077 (4)	0.51 (2)
H27	0.3607	0.4145	0.3999	0.092*	0.51 (2)
C28	0.399 (2)	0.235 (2)	0.3948 (16)	0.075 (5)	0.51 (2)
H28	0.3521	0.2068	0.3413	0.090*	0.51 (2)
O29	0.4960 (14)	0.151 (2)	0.4681 (13)	0.062 (4)	0.51 (2)
C28A	0.3720 (18)	0.3008 (19)	0.4016 (13)	0.058 (4)	0.49 (2)
H28A	0.3158	0.3466	0.3607	0.070*	0.49 (2)
C27A	0.418 (2)	0.1871 (19)	0.3925 (15)	0.066 (4)	0.49 (2)
H27A	0.4114	0.1472	0.3413	0.079*	0.49 (2)
C26A	0.466 (3)	0.150 (5)	0.457 (3)	0.070 (5)	0.49 (2)
H26A	0.4823	0.0607	0.4651	0.084*	0.49 (2)
O29A	0.4309 (12)	0.3359 (15)	0.4912 (11)	0.072 (4)	0.49 (2)

	U11	U22	U33	U12	U13	U23
Cl1	0.0522 (8)	0.0505 (8)	0.0493 (8)	0.0131 (6)	0.0198 (7)	0.0090 (6)
Au2	0.03944 (13)	0.03606 (13)	0.02786 (12)	0.00058 (8)	0.00691 (8)	0.00152 (8)
P3	0.0335 (6)	0.0360 (7)	0.0249 (6)	−0.0020 (5)	0.0057 (5)	0.0002 (5)
C4	0.054 (3)	0.036 (3)	0.033 (3)	−0.013 (2)	0.019 (2)	−0.007 (2)
C5	0.048 (3)	0.062 (4)	0.053 (3)	−0.019 (3)	0.025 (3)	−0.016 (3)
C6	0.074 (4)	0.075 (4)	0.079 (5)	−0.032 (4)	0.047 (4)	−0.038 (4)
C7	0.108 (5)	0.067 (4)	0.082 (5)	−0.039 (4)	0.073 (5)	−0.034 (4)
C8	0.128 (6)	0.049 (4)	0.048 (4)	−0.021 (4)	0.051 (4)	−0.010 (3)
C9	0.081 (4)	0.048 (3)	0.036 (3)	−0.009 (3)	0.024 (3)	−0.003 (2)
C10	0.032 (2)	0.039 (3)	0.026 (2)	−0.011 (2)	0.0051 (19)	−0.001 (2)
C11	0.054 (3)	0.044 (3)	0.033 (3)	−0.008 (2)	0.002 (2)	0.001 (2)
C12	0.059 (4)	0.064 (4)	0.044 (3)	−0.012 (3)	−0.005 (3)	0.011 (3)
C13	0.054 (3)	0.080 (4)	0.030 (3)	−0.021 (3)	0.000 (3)	−0.002 (3)
C14	0.053 (4)	0.066 (4)	0.040 (3)	−0.014 (3)	0.007 (3)	−0.017 (3)
C15	0.041 (3)	0.045 (3)	0.040 (3)	−0.004 (2)	0.009 (2)	−0.007 (2)
C16	0.030 (2)	0.036 (2)	0.025 (2)	0.000 (2)	0.0021 (19)	0.002 (2)
C17	0.033 (3)	0.033 (3)	0.041 (3)	−0.0011 (19)	0.008 (2)	−0.002 (2)
C18	0.052 (3)	0.039 (3)	0.041 (3)	0.004 (2)	0.009 (3)	−0.004 (2)
C19	0.062 (4)	0.036 (3)	0.047 (3)	−0.011 (3)	0.007 (3)	−0.003 (3)
C20	0.053 (3)	0.046 (3)	0.043 (3)	−0.007 (2)	0.008 (3)	0.002 (2)
C21	0.039 (3)	0.044 (3)	0.028 (2)	−0.004 (2)	0.004 (2)	0.005 (2)
C22	0.042 (3)	0.056 (3)	0.038 (3)	−0.010 (3)	0.014 (2)	0.002 (3)
N23	0.040 (2)	0.057 (3)	0.036 (2)	−0.007 (2)	0.015 (2)	0.003 (2)
C24	0.067 (4)	0.066 (4)	0.049 (3)	−0.013 (3)	0.022 (3)	−0.012 (3)
C25	0.070 (4)	0.062 (4)	0.046 (3)	−0.017 (3)	0.027 (3)	−0.005 (3)
C26	0.088 (10)	0.069 (9)	0.044 (8)	0.000 (9)	0.020 (8)	0.002 (7)
C27	0.091 (9)	0.090 (9)	0.048 (9)	0.006 (8)	0.025 (8)	0.007 (8)
C28	0.089 (9)	0.080 (10)	0.045 (7)	−0.008 (9)	0.012 (7)	0.000 (9)
O29	0.082 (9)	0.059 (5)	0.038 (7)	−0.008 (8)	0.016 (7)	−0.011 (5)
C28A	0.075 (8)	0.061 (9)	0.044 (8)	−0.003 (7)	0.026 (6)	0.003 (7)
C27A	0.092 (9)	0.069 (9)	0.036 (6)	−0.011 (8)	0.022 (6)	−0.005 (7)
C26A	0.084 (11)	0.064 (8)	0.044 (8)	−0.013 (9)	0.005 (8)	−0.004 (7)
O29A	0.077 (8)	0.076 (7)	0.063 (8)	−0.008 (6)	0.026 (7)	0.010 (6)

Cl1—Au2	2.2820 (13)	C17—H17	0.9500
Au2—P3	2.2321 (13)	C18—C19	1.371 (8)
P3—C10	1.813 (5)	C18—H18	0.9500
P3—C4	1.821 (5)	C19—C20	1.368 (8)
P3—C16	1.822 (5)	C19—H19	0.9500
C4—C5	1.386 (7)	C20—C21	1.397 (7)
C4—C9	1.389 (7)	C20—H20	0.9500
C5—C6	1.394 (8)	C21—C22	1.446 (8)
C5—H5	0.9500	C22—N23	1.254 (6)
C6—C7	1.390 (10)	C22—H22	0.9500
C6—H6	0.9500	N23—C24	1.467 (7)
C7—C8	1.370 (10)	C24—C25	1.503 (9)
C7—H7	0.9500	C24—H24A	0.9900
C8—C9	1.386 (8)	C24—H24B	0.9900
C8—H8	0.9500	C25—C26	1.28 (2)
C9—H9	0.9500	C25—O29	1.30 (2)
C10—C11	1.377 (7)	C25—O29A	1.388 (17)
C10—C15	1.384 (7)	C25—C26A	1.41 (4)
C11—C12	1.381 (7)	C26—C27	1.41 (3)
C11—H11	0.9500	C26—H26	0.9500
C12—C13	1.374 (8)	C27—C28	1.27 (3)
C12—H12	0.9500	C27—H27	0.9500
C13—C14	1.364 (8)	C28—O29	1.68 (4)
C13—H13	0.9500	C28—H28	0.9500
C14—C15	1.396 (7)	C28A—C27A	1.37 (3)
C14—H14	0.9500	C28A—O29A	1.50 (2)
C15—H15	0.9500	C28A—H28A	0.9500
C16—C17	1.385 (7)	C27A—C26A	1.13 (5)
C16—C21	1.430 (7)	C27A—H27A	0.9500
C17—C18	1.391 (6)	C26A—H26A	0.9500
P3—Au2—Cl1	176.49 (5)	C19—C18—H18	120.4
C10—P3—C4	105.1 (2)	C17—C18—H18	120.4
C10—P3—C16	110.2 (2)	C20—C19—C18	119.6 (5)
C4—P3—C16	103.0 (2)	C20—C19—H19	120.2
C10—P3—Au2	112.74 (17)	C18—C19—H19	120.2
C4—P3—Au2	112.53 (18)	C19—C20—C21	123.1 (6)
C16—P3—Au2	112.55 (15)	C19—C20—H20	118.5
C5—C4—C9	119.1 (5)	C21—C20—H20	118.5
C5—C4—P3	122.7 (4)	C20—C21—C16	117.5 (5)
C9—C4—P3	118.1 (4)	C20—C21—C22	118.3 (5)
C4—C5—C6	120.3 (6)	C16—C21—C22	124.2 (4)
C4—C5—H5	119.8	N23—C22—C21	122.6 (5)
C6—C5—H5	119.8	N23—C22—H22	118.7
C7—C6—C5	119.7 (7)	C21—C22—H22	118.7
C7—C6—H6	120.1	C22—N23—C24	118.5 (5)
C5—C6—H6	120.1	N23—C24—C25	109.4 (5)
C8—C7—C6	120.0 (6)	N23—C24—H24A	109.8
C8—C7—H7	120.0	C25—C24—H24A	109.8
C6—C7—H7	120.0	N23—C24—H24B	109.8
C7—C8—C9	120.4 (6)	C25—C24—H24B	109.8
C7—C8—H8	119.8	H24A—C24—H24B	108.2
C9—C8—H8	119.8	C26—C25—O29	123.5 (16)
C8—C9—C4	120.4 (6)	O29—C25—O29A	109.9 (13)
C8—C9—H9	119.8	C26—C25—C26A	117 (2)
C4—C9—H9	119.8	O29A—C25—C26A	98.6 (19)
C11—C10—C15	119.4 (5)	C26—C25—C24	112.4 (12)
C11—C10—P3	122.9 (4)	O29—C25—C24	118.2 (11)
C15—C10—P3	117.7 (4)	O29A—C25—C24	131.8 (9)
C10—C11—C12	119.6 (5)	C26A—C25—C24	129.2 (18)
C10—C11—H11	120.2	C25—C26—C27	98.9 (17)
C12—C11—H11	120.2	C25—C26—H26	130.5
C13—C12—C11	121.1 (6)	C27—C26—H26	130.5
C13—C12—H12	119.5	C28—C27—C26	115 (2)
C11—C12—H12	119.5	C28—C27—H27	122.3
C14—C13—C12	119.9 (5)	C26—C27—H27	122.3
C14—C13—H13	120.1	C27—C28—O29	102.9 (19)
C12—C13—H13	120.1	C27—C28—H28	128.6
C13—C14—C15	119.6 (5)	O29—C28—H28	128.6
C13—C14—H14	120.2	C25—O29—C28	92.1 (17)
C15—C14—H14	120.2	C27A—C28A—O29A	103.8 (18)
C10—C15—C14	120.4 (5)	C27A—C28A—H28A	128.1
C10—C15—H15	119.8	O29A—C28A—H28A	128.1
C14—C15—H15	119.8	C26A—C27A—C28A	107 (3)
C17—C16—C21	118.0 (4)	C26A—C27A—H27A	126.3
C17—C16—P3	119.5 (4)	C28A—C27A—H27A	126.3
C21—C16—P3	122.2 (4)	C27A—C26A—C25	120 (4)
C16—C17—C18	122.6 (5)	C27A—C26A—H26A	119.8
C16—C17—H17	118.7	C25—C26A—H26A	119.8
C18—C17—H17	118.7	C25—O29A—C28A	106.0 (13)
C19—C18—C17	119.2 (5)
C10—P3—C4—C5	−25.0 (5)	C18—C19—C20—C21	−1.0 (9)
C16—P3—C4—C5	90.5 (5)	C19—C20—C21—C16	−0.6 (8)
Au2—P3—C4—C5	−148.1 (4)	C19—C20—C21—C22	179.6 (5)
C10—P3—C4—C9	158.5 (4)	C17—C16—C21—C20	1.8 (7)
C16—P3—C4—C9	−86.0 (4)	P3—C16—C21—C20	−171.8 (4)
Au2—P3—C4—C9	35.4 (4)	C17—C16—C21—C22	−178.3 (5)
C9—C4—C5—C6	−0.6 (8)	P3—C16—C21—C22	8.0 (7)
P3—C4—C5—C6	−177.1 (4)	C20—C21—C22—N23	−175.9 (5)
C4—C5—C6—C7	1.2 (9)	C16—C21—C22—N23	4.3 (8)
C5—C6—C7—C8	−0.5 (9)	C21—C22—N23—C24	178.2 (5)
C6—C7—C8—C9	−0.8 (9)	C22—N23—C24—C25	−105.0 (6)
C7—C8—C9—C4	1.3 (9)	N23—C24—C25—C26	56.6 (14)
C5—C4—C9—C8	−0.6 (8)	N23—C24—C25—O29	−149.6 (13)
P3—C4—C9—C8	176.0 (4)	N23—C24—C25—O29A	34.5 (12)
C4—P3—C10—C11	85.8 (5)	N23—C24—C25—C26A	−136 (2)
C16—P3—C10—C11	−24.6 (5)	O29—C25—C26—C27	28 (2)
Au2—P3—C10—C11	−151.3 (4)	O29A—C25—C26—C27	−38 (3)
C4—P3—C10—C15	−95.4 (4)	C26A—C25—C26—C27	12 (3)
C16—P3—C10—C15	154.3 (4)	C24—C25—C26—C27	−179.4 (11)
Au2—P3—C10—C15	27.6 (4)	C25—C26—C27—C28	−11 (3)
C15—C10—C11—C12	−0.8 (8)	C26—C27—C28—O29	−4 (3)
P3—C10—C11—C12	178.1 (4)	C26—C25—O29—C28	−29 (2)
C10—C11—C12—C13	−0.3 (9)	O29A—C25—O29—C28	−2.8 (17)
C11—C12—C13—C14	−0.2 (10)	C26A—C25—O29—C28	42 (11)
C12—C13—C14—C15	1.9 (9)	C24—C25—O29—C28	−179.6 (11)
C11—C10—C15—C14	2.4 (8)	C27—C28—O29—C25	17 (2)
P3—C10—C15—C14	−176.5 (4)	O29A—C28A—C27A—C26A	15 (3)
C13—C14—C15—C10	−3.0 (9)	C28A—C27A—C26A—C25	−22 (5)
C10—P3—C16—C17	112.4 (4)	C26—C25—C26A—C27A	−1 (5)
C4—P3—C16—C17	0.7 (4)	O29—C25—C26A—C27A	−119 (13)
Au2—P3—C16—C17	−120.8 (4)	O29A—C25—C26A—C27A	19 (4)
C10—P3—C16—C21	−74.0 (4)	C24—C25—C26A—C27A	−168 (3)
C4—P3—C16—C21	174.3 (4)	C26—C25—O29A—C28A	130 (4)
Au2—P3—C16—C21	52.8 (4)	O29—C25—O29A—C28A	4.6 (16)
C21—C16—C17—C18	−1.7 (7)	C26A—C25—O29A—C28A	−6 (2)
P3—C16—C17—C18	172.1 (4)	C24—C25—O29A—C28A	−179.3 (9)
C16—C17—C18—C19	0.2 (8)	C27A—C28A—O29A—C25	−3.5 (18)
C17—C18—C19—C20	1.2 (8)