Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060709/bt2619sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060709/bt2619Isup2.hkl |
CCDC reference: 672752
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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).
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.
H atoms were were refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C) using a riding model with Caromatic—H = 0.95 Å and Cmethyl—H = 0.98 Å. The phenolic ring and the methyl H atoms are disordered over two equally occupied positions.
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).
[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) Å3 | 0.25 × 0.06 × 0.06 mm |
Z = 2 |
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 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)] = 0.012 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.027 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0113P)2 + 0.2414P] where P = (Fo2 + 2Fc2)/3 |
1506 reflections | (Δ/σ)max = 0.001 |
120 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
[Au(CH3)2(C13H10NO)] | V = 683.02 (13) Å3 |
Mr = 423.25 | Z = 2 |
Monoclinic, P21/m | Mo Kα radiation |
a = 8.5316 (10) Å | µ = 10.76 mm−1 |
b = 7.3356 (7) Å | T = 150 K |
c = 11.1180 (13) Å | 0.25 × 0.06 × 0.06 mm |
β = 101.006 (3)° |
Bruker–Nonius X8 APEX CCD area-detector diffractometer | 1506 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1423 reflections with I > 2σ(I) |
Tmin = 0.454, Tmax = 0.565 | Rint = 0.018 |
4954 measured reflections |
R[F2 > 2σ(F2)] = 0.012 | 0 restraints |
wR(F2) = 0.027 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.43 e Å−3 |
1506 reflections | Δρmin = −0.52 e Å−3 |
120 parameters |
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 | 0.935702 (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 |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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 |
Experimental details
Crystal data | |
Chemical formula | [Au(CH3)2(C13H10NO)] |
Mr | 423.25 |
Crystal system, space group | Monoclinic, P21/m |
Temperature (K) | 150 |
a, b, c (Å) | 8.5316 (10), 7.3356 (7), 11.1180 (13) |
β (°) | 101.006 (3) |
V (Å3) | 683.02 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 10.76 |
Crystal size (mm) | 0.25 × 0.06 × 0.06 |
Data collection | |
Diffractometer | Bruker–Nonius X8 APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.454, 0.565 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4954, 1506, 1423 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.012, 0.027, 1.11 |
No. of reflections | 1506 |
No. of parameters | 120 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.52 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXTL (Bruker, 2004), POV-RAY (Cason, 2002).
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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.