Dimeth­yl[2-(phenyl­imino­meth­yl)­phenol­ato-κ²N,O]gold(III)

The Au atom in the title compound, [Au(CH₃)₂(C₁₃H₁₀NO)], has a square-planar coordination geometry. The mol­ecule is located on a crystallographic mirror plane. The phenolate ring is disordered over two equally occupied positions. The mol­ecules are packed in infinite stacks parallel to the b axis, with an Au...Au distance of 4.2106 (4) Å.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.012
• wR factor = 0.027
• Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.38 Ratio

Author Response: The atom is disordered

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.22 Ratio

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.93
PLAT213_ALERT_2_C Atom C12     has ADP max/min Ratio .............       3.50 prola
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Au1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.96
PLAT301_ALERT_3_C Main Residue  Disorder .........................      22.00 Perc.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.929
            Tmax scaled      0.524 Tmin scaled      0.422

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The title compound has molecular structure constructed from neutral molecules (CH₃)₂Au(C₁₃H₁₀NO). The gold atom in the molecule has a slightly distorted square planar configuration formed by oxygen and nitrogen atoms of salicilaldimine ligand, and two carbon atoms of methyl groups (Fig. 1). In the coordination square, Au—O and Au—N distances differ slightly, and O—Au—N angle is very close to 90°. The values of Au—CH₃ bonds are typical for dimethylgold(III) derivatives (Shibata et al., 1990; Bessonov, Baidina et al., 2007). The salicylaldimine fragment is located on a mirror plane, however carbon atoms C5, C6, C7, C8 and C9 are disordered. The planes of salycilaldimine and phenyl ring are nearly perpendicular (the angle is about 91°). In the crystal, molecules are packed in infinite stacks along the monoclinic axis with the shortest Au···Au distance of 4.2106 (4) Å and Au—Au—Au angle of 121.173 (8)° (Fig. 2). The oxygen atom is involved in intermolecular O···H—C interactions with O···C distances of 3.291 (3) Å. The shortest intermolecular H···H distance in the crystal is about 2.5 Å.

Related literature

Dimethylgold(III) derivatives are used in metal-organic chemical vapor deposition processes because of their volatility and thermal stability (Larson et al., 1987; Semyannikov et al., 2006; Bessonov, Morozova et al., 2007; Bessonov, Baidina et al., 2007). For a similar structure, see: Shibata et al. (1990). For literature related to the synthesis, see: Bessonov et al. (2008); Murray et al. (1973).

S2. Experimental

Sodium bicarbonate, NaHCO₃, and dimethylgold(III) iodide, [(CH₃)₂AuI]₂, (prepared as described in Bessonov et al., 2008) were added to a solution of N-phenylsalicylaldimine in methanol. The mixture was stirred for 6 h in an argon flow. Then, the methanol was removed in vacuum and the residue was redissolved in hexane. The hexane solution was filtered and the volatile components were removed in vacuum. The complex was purified by recrystallization from hexane at -10°C. Pale yellow crystals suitable for X-ray analysis were formed in yield of 80%. The melting point of the complex was 147–150°C (154°C from Murray et al., 1973). The product is stable to air and moisture and soluble in most common organic solvents.

S3. Refinement

H atoms were were refined with fixed individual displacement parameters [U(H) = 1.2 U_eq(C) using a riding model with C_aromatic—H = 0.95 Å and C_methyl—H = 0.98 Å. The phenolic ring and the methyl H atoms are disordered over two equally occupied positions.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXTL (Bruker, 2004); program(s) used to refine structure: SHELXTL (Bruker, 2004); molecular graphics: POV-RAY (Cason, 2002); software used to prepare material for publication: SHELXTL (Bruker, 2004).

Figures

	Fig. 1. Plot of Me2Au(Sal=N—Ph) molecule showing the atom numbering for the core atoms. Displacement ellipsoids are drawn at the 50% probability level. Only one set of the two disordered atoms is shown.
	Fig. 2. A packing diagram of the Me2Au(Sal=N—Ph) structure, viewed along the b axis. H atoms omitted for clarity. Only one set of the two disordered atoms is shown.

Dimethyl[2-(phenyliminomethyl)phenolato-κ²N,O]gold(III)

Crystal data

[Au(CH3)2(C13H10NO)]	F(000) = 400
Mr = 423.25	Dx = 2.058 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 3995 reflections
a = 8.5316 (10) Å	θ = 2.4–28.3°
b = 7.3356 (7) Å	µ = 10.76 mm^−1
c = 11.1180 (13) Å	T = 150 K
β = 101.006 (3)°	Needle, pale yellow
V = 683.02 (13) Å^3	0.25 × 0.06 × 0.06 mm
Z = 2

Data collection

Bruker–Nonius X8 APEX CCD area-detector diffractometer	1506 independent reflections
Radiation source: fine-focus sealed tube	1423 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 25 pixels mm^-1	θmax = 26.4°, θmin = 1.9°
ϕ scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −6→9
Tmin = 0.454, Tmax = 0.565	l = −13→13
4954 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.012	Hydrogen site location: difference Fourier map
wR(F^2) = 0.027	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0113P)^2 + 0.2414P] where P = (Fo^2 + 2Fc^2)/3
1506 reflections	(Δ/σ)max = 0.001
120 parameters	Δρmax = 0.43 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Au1	0.935702 (14)	0.2500	0.069963 (11)	0.02283 (5)
N1	1.1812 (3)	0.2500	0.0660 (2)	0.0256 (6)
O1	0.8825 (3)	0.2500	−0.12028 (19)	0.0255 (5)
C13	0.9623 (4)	0.2500	0.2555 (3)	0.0393 (10)
H13A	0.8683	0.3061	0.2790	0.059*	0.50
H13B	1.0579	0.3196	0.2911	0.059*	0.50
H13C	0.9733	0.1243	0.2857	0.059*	0.50
C11	0.9822 (4)	0.2500	−0.1954 (3)	0.0265 (7)
C5	1.2359 (5)	0.2098 (5)	−0.0345 (4)	0.0203 (14)	0.50
H5	1.3454	0.1770	−0.0232	0.024*	0.50
C12	0.6969 (5)	0.2500	0.0668 (4)	0.086 (2)
H12A	0.6630	0.3726	0.0857	0.129*	0.50
H12B	0.6725	0.1636	0.1278	0.129*	0.50
H12C	0.6402	0.2138	−0.0148	0.129*	0.50
C1	1.3007 (4)	0.2500	0.1778 (3)	0.0263 (7)
C4	1.5304 (4)	0.2500	0.3890 (3)	0.0367 (9)
H4	1.6108	0.2500	0.4610	0.044*
C2	1.3560 (3)	0.0877 (4)	0.2304 (2)	0.0438 (7)
H2	1.3156	−0.0246	0.1947	0.053*
C3	1.4724 (4)	0.0896 (4)	0.3371 (3)	0.0483 (8)
H3	1.5117	−0.0224	0.3740	0.058*
C6	1.1492 (5)	0.2099 (6)	−0.1589 (4)	0.0217 (15)	0.50
C10	0.9187 (4)	0.2500	−0.3223 (3)	0.0338 (8)
H10	0.8088	0.2767	−0.3498	0.041*	0.50
C9	1.0136 (6)	0.2117 (7)	−0.4081 (4)	0.0292 (18)	0.50
H9	0.9654	0.2010	−0.4922	0.035*	0.50
C8	1.1776 (6)	0.1888 (7)	−0.3728 (4)	0.0379 (15)	0.50
H8	1.2433	0.1738	−0.4321	0.045*	0.50
C7	1.2419 (6)	0.1884 (6)	−0.2503 (4)	0.0320 (13)	0.50
H7	1.3540	0.1730	−0.2257	0.038*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Au1	0.01707 (7)	0.03630 (8)	0.01489 (7)	0.000	0.00249 (5)	0.000
N1	0.0208 (14)	0.0411 (17)	0.0138 (13)	0.000	0.0006 (11)	0.000
O1	0.0201 (11)	0.0402 (13)	0.0153 (11)	0.000	0.0011 (9)	0.000
C13	0.030 (2)	0.073 (3)	0.0160 (18)	0.000	0.0060 (15)	0.000
C11	0.0248 (17)	0.0351 (19)	0.0192 (17)	0.000	0.0032 (14)	0.000
C5	0.0171 (18)	0.020 (4)	0.023 (2)	0.0005 (15)	0.0014 (15)	−0.0012 (16)
C12	0.018 (2)	0.213 (7)	0.027 (2)	0.000	0.0045 (17)	0.000
C1	0.0156 (15)	0.049 (2)	0.0143 (16)	0.000	0.0021 (13)	0.000
C4	0.0229 (18)	0.067 (3)	0.0172 (17)	0.000	−0.0029 (14)	0.000
C2	0.0474 (17)	0.0474 (17)	0.0285 (14)	−0.0204 (13)	−0.0134 (12)	0.0121 (12)
C3	0.0539 (18)	0.0532 (18)	0.0302 (15)	−0.0070 (15)	−0.0111 (13)	0.0173 (14)
C6	0.025 (2)	0.024 (4)	0.0152 (18)	−0.0032 (17)	0.0019 (15)	0.0001 (17)
C10	0.0287 (19)	0.053 (2)	0.0172 (17)	0.000	−0.0018 (14)	0.000
C9	0.039 (2)	0.031 (6)	0.0158 (19)	−0.001 (2)	0.0012 (17)	−0.0008 (19)
C8	0.036 (3)	0.060 (4)	0.021 (2)	−0.003 (2)	0.014 (2)	−0.004 (2)
C7	0.024 (2)	0.047 (3)	0.026 (2)	0.0008 (19)	0.0071 (19)	−0.0023 (19)

Geometric parameters (Å, º)

Au1—C12	2.030 (4)	C8—C7	1.368 (7)
Au1—C13	2.031 (3)	C13—H13A	0.9800
Au1—O1	2.077 (2)	C13—H13B	0.9800
Au1—N1	2.104 (3)	C13—H13C	0.9800
N1—C5	1.324 (5)	C12—H12A	0.9800
N1—C1	1.449 (4)	C12—H12B	0.9800
O1—C11	1.301 (4)	C12—H12C	0.9800
C11—C10	1.411 (5)	C5—H5	0.9500
C11—C6	1.436 (5)	C4—H4	0.9500
C5—C6	1.438 (6)	C2—H2	0.9500
C1—C2	1.369 (3)	C3—H3	0.9500
C4—C3	1.361 (4)	C10—H10	0.9500
C2—C3	1.392 (4)	C9—H9	0.9500
C6—C7	1.412 (6)	C8—H8	0.9500
C10—C9	1.393 (6)	C7—H7	0.9500
C9—C8	1.389 (7)
C12—Au1—C13	86.27 (16)	H13A—C13—H13B	109.5
C12—Au1—O1	87.62 (14)	Au1—C13—H13C	109.5
C13—Au1—O1	173.89 (11)	H13A—C13—H13C	109.5
C12—Au1—N1	177.84 (14)	H13B—C13—H13C	109.5
C13—Au1—N1	95.89 (13)	N1—C5—H5	116.1
O1—Au1—N1	90.22 (9)	C6—C5—H5	116.1
C5—N1—C1	114.9 (3)	Au1—C12—H12A	109.5
C5—N1—Au1	122.0 (2)	Au1—C12—H12B	109.5
C1—N1—Au1	121.5 (2)	H12A—C12—H12B	109.5
C11—O1—Au1	127.7 (2)	Au1—C12—H12C	109.5
O1—C11—C10	117.9 (3)	H12A—C12—H12C	109.5
C10—C11—C6	117.0 (3)	H12B—C12—H12C	109.5
O1—C11—C6	123.7 (3)	C3—C4—H4	120.2
N1—C5—C6	127.8 (4)	C1—C2—H2	120.5
C2—C1—N1	119.70 (16)	C3—C2—H2	120.5
C1—C2—C3	119.2 (3)	C4—C3—H3	119.6
C4—C3—C2	120.8 (3)	C2—C3—H3	119.6
C7—C6—C11	118.9 (4)	C9—C10—H10	119.2
C7—C6—C5	115.8 (4)	C11—C10—H10	119.2
C11—C6—C5	124.9 (4)	C8—C9—H9	119.5
C9—C10—C11	121.4 (4)	C10—C9—H9	119.5
C10—C9—C8	121.2 (4)	C7—C8—H8	120.9
C7—C8—C9	118.3 (4)	C9—C8—H8	120.9
C8—C7—C6	122.8 (4)	C8—C7—H7	118.5
Au1—C13—H13A	109.5	C6—C7—H7	118.5
Au1—C13—H13B	109.5