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Acta Cryst. (2009). E65, m1438    [ doi:10.1107/S1600536809043542 ]

Bis(2-hydroxybenzaldehyde oximato-[kappa]O)triphenylantimony(V)

L. Dong, H. Yin, L. Wen and D. Wang

Abstract top

The molecule of the title compound, [Sb(C6H5)3(C7H6NO2)2], is located on a twofold axis defined by the metal center and two C atoms of a coordinated phenyl group. The Sb center has a slightly distorted trigonal-bipyramidal geometry, with the axial positions occupied by the O atoms of symmetry-related 2-hydroxybenzaldehyde oximate ligands. An intramolecular O-H...N interaction is present. The crystal structure is stabilized by C-H...O interactions.

Comment top

Among numerous multidentate organic ligands, oximes are of particular importance, because of their remarkable structural diversity and biological implications. As a continuation of our interest in this area, we have synthesized the title complex. The molecular structures of the compound is depicted in Fig.1. The antimony atom in the compound is five-coordinate, and its geometries is represented as a distorted trigonal bipyramid. The Sb—O bond distance of 2.078 (2) Å is similar to that reported by Wang (Wang et al., 2004; 2.094 (2)Å) . The Sb—C bond distances [2.102 (3) Å; 2.097 (5) Å] fall in the normal range for Sb—C(phenyl) bonds. In the crystal structure, molecules are linked by C—H···O hydrogen bonds.

Related literature top

For related structures, see: Wang et al. (2004); Sharutin et al. (2004).

Experimental top

Salicylaldoxime (0.4 mmol) was added to a methanol solution of sodium (0.4 mmol) and heated under reflux for 0.5 h. To this solution was added triphenylantimony dichloride (0.2 mmol) in benzene and the mixture was refluxed for 5 h, cooled and filtered. The filtrate was evaporated in vacuo. The obtained solid was recrystallized from dichloromethane-petroleum ether. (yield 86%. m.p.431k). Anal. Calcd (%) for C32H27N2O4Sb (Mr = 625.33): C, 61.46; H, 4.35; N, 4.48; O,10.23. Found (%): C, 61.47; H, 4.40; N, 4.46; O,10.26.

Refinement top

The C—H and O—H H atoms were positioned with idealized geometry (O—H = 0.82 Å and C—H = 0.93 Å) and were refined using a riding model approximation with Uiso(H) = 1.2 Ueq(C, O).The final difference map showed a high residual peak (1.38 e Å-3) at a distance of 0.35 Å from H17.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity. Symmetry code: (A) = -x + 1, -y + 3/2, z.
[Figure 2] Fig. 2. View of the two-dimensional layer structure in the title compound. Intermolecular hydrogen bonds are shown as dashed lines.
Bis(2-hydroxybenzaldehyde oximato-κO)triphenylantimony(V) top
Crystal data top
[Sb(C6H5)3(C7H6NO2)2]Dx = 1.451 Mg m−3
Mr = 625.31Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 5826 reflections
Hall symbol: -I 4adθ = 2.5–25.5°
a = 16.6012 (15) ŵ = 1.00 mm−1
c = 20.775 (2) ÅT = 298 K
V = 5725.6 (9) Å3Block, colourless
Z = 80.38 × 0.30 × 0.17 mm
F(000) = 2528
Data collection top
Siemens SMART CCD area-detector
diffractometer		3487 independent reflections
Radiation source: fine-focus sealed tube2410 reflections with I > 2σ(I)
graphiteRint = 0.034
φ and ω scansθmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −21→21
Tmin = 0.702, Tmax = 0.848k = −9→22
17411 measured reflectionsl = −26→26
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.030P)2 + 9.4858P]
where P = (Fo2 + 2Fc2)/3
3487 reflections(Δ/σ)max = 0.001
178 parametersΔρmax = 1.38 e Å−3
0 restraintsΔρmin = −0.68 e Å−3
Crystal data top
[Sb(C6H5)3(C7H6NO2)2]Z = 8
Mr = 625.31Mo Kα radiation
Tetragonal, I41/aµ = 1.00 mm−1
a = 16.6012 (15) ÅT = 298 K
c = 20.775 (2) Å0.38 × 0.30 × 0.17 mm
V = 5725.6 (9) Å3
Data collection top
Siemens SMART CCD area-detector
diffractometer		3487 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2410 reflections with I > 2σ(I)
Tmin = 0.702, Tmax = 0.848Rint = 0.034
17411 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.085Δρmax = 1.38 e Å−3
S = 1.09Δρmin = −0.68 e Å−3
3487 reflectionsAbsolute structure: ?
178 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Sb10.50000.75000.977300 (13)0.03630 (10)
N10.65745 (16)0.80646 (15)0.93840 (13)0.0438 (6)
O10.62512 (13)0.74876 (13)0.97978 (10)0.0442 (5)
O20.66631 (16)0.89097 (18)0.83231 (13)0.0716 (8)
H20.64540.86110.85890.107*
C10.7300 (2)0.8254 (2)0.95055 (16)0.0474 (8)
H10.75510.80430.98690.057*
C20.7748 (2)0.8797 (2)0.90850 (17)0.0467 (8)
C30.7419 (2)0.9098 (2)0.85145 (18)0.0515 (8)
C40.7874 (3)0.9596 (2)0.8126 (2)0.0704 (11)
H40.76530.97990.77470.084*
C50.8650 (3)0.9796 (3)0.8293 (2)0.0762 (13)
H50.89511.01300.80260.091*
C60.8981 (3)0.9506 (3)0.8848 (2)0.0778 (13)
H60.95060.96430.89590.093*
C70.8535 (2)0.9012 (3)0.92426 (19)0.0647 (10)
H70.87630.88190.96210.078*
C80.50453 (19)0.64233 (17)1.03043 (14)0.0384 (7)
C90.4426 (2)0.62433 (19)1.07230 (15)0.0477 (8)
H90.39790.65791.07510.057*
C100.4475 (3)0.5556 (2)1.11027 (17)0.0573 (9)
H100.40620.54351.13890.069*
C110.5130 (3)0.5054 (2)1.10563 (17)0.0572 (9)
H110.51590.45961.13130.069*
C120.5738 (2)0.5225 (2)1.06345 (18)0.0543 (9)
H120.61780.48801.06030.065*
C130.5701 (2)0.59106 (19)1.02534 (16)0.0458 (8)
H130.61140.60250.99650.055*
C140.50000.75000.8764 (2)0.0523 (12)
C150.5554 (3)0.7042 (2)0.84211 (19)0.0655 (11)
H150.59310.67340.86430.079*
C160.5554 (4)0.7039 (4)0.7751 (2)0.0985 (19)
H160.59220.67290.75220.118*
C170.50000.75000.7441 (4)0.102 (3)
H170.50000.75000.69930.123*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Sb10.03787 (17)0.03277 (16)0.03825 (16)0.00025 (13)0.0000.000
N10.0412 (15)0.0414 (14)0.0487 (15)−0.0016 (12)0.0064 (12)0.0021 (12)
O10.0393 (12)0.0429 (12)0.0506 (13)0.0003 (10)0.0072 (10)0.0083 (10)
O20.0554 (16)0.093 (2)0.0665 (17)−0.0152 (15)−0.0083 (13)0.0257 (15)
C10.0455 (19)0.0501 (19)0.0466 (18)0.0021 (15)0.0034 (15)0.0023 (16)
C20.0446 (18)0.0428 (18)0.053 (2)−0.0002 (15)0.0048 (16)−0.0019 (16)
C30.049 (2)0.048 (2)0.057 (2)−0.0017 (16)0.0054 (17)0.0032 (17)
C40.067 (3)0.071 (3)0.074 (3)−0.005 (2)0.005 (2)0.026 (2)
C50.068 (3)0.068 (3)0.093 (3)−0.016 (2)0.015 (2)0.022 (2)
C60.055 (2)0.082 (3)0.096 (3)−0.023 (2)0.004 (2)0.014 (3)
C70.054 (2)0.075 (3)0.065 (2)−0.009 (2)−0.0021 (19)0.011 (2)
C80.0441 (17)0.0323 (15)0.0387 (16)−0.0002 (13)−0.0010 (13)−0.0017 (13)
C90.052 (2)0.0418 (18)0.0489 (19)0.0026 (15)0.0063 (16)−0.0012 (15)
C100.074 (3)0.0462 (19)0.052 (2)−0.0065 (18)0.0121 (18)0.0057 (16)
C110.080 (3)0.0347 (17)0.057 (2)−0.0026 (18)−0.007 (2)0.0049 (16)
C120.059 (2)0.0369 (17)0.067 (2)0.0070 (16)−0.0069 (19)−0.0009 (17)
C130.0474 (19)0.0372 (17)0.0527 (19)0.0004 (14)0.0028 (16)−0.0015 (15)
C140.069 (3)0.048 (3)0.041 (2)−0.015 (2)0.0000.000
C150.079 (3)0.064 (2)0.054 (2)−0.015 (2)0.010 (2)−0.0095 (19)
C160.127 (5)0.105 (4)0.064 (3)−0.044 (4)0.027 (3)−0.030 (3)
C170.141 (8)0.110 (7)0.055 (4)−0.065 (6)0.0000.000
Geometric parameters (Å, °) top
Sb1—O1i2.078 (2)C7—H70.9300
Sb1—O12.078 (2)C8—C91.379 (4)
Sb1—C142.097 (5)C8—C131.386 (4)
Sb1—C8i2.102 (3)C9—C101.390 (5)
Sb1—C82.102 (3)C9—H90.9300
N1—C11.271 (4)C10—C111.373 (5)
N1—O11.394 (3)C10—H100.9300
O2—C31.353 (4)C11—C121.367 (5)
O2—H20.8200C11—H110.9300
C1—C21.459 (5)C12—C131.388 (5)
C1—H10.9300C12—H120.9300
C2—C71.394 (5)C13—H130.9300
C2—C31.397 (5)C14—C15i1.389 (5)
C3—C41.381 (5)C14—C151.389 (5)
C4—C51.375 (6)C15—C161.393 (6)
C4—H40.9300C15—H150.9300
C5—C61.365 (6)C16—C171.359 (7)
C5—H50.9300C16—H160.9300
C6—C71.375 (5)C17—C16i1.359 (7)
C6—H60.9300C17—H170.9300
O1i—Sb1—O1177.16 (12)C6—C7—H7119.4
O1i—Sb1—C1491.42 (6)C2—C7—H7119.4
O1—Sb1—C1491.42 (6)C9—C8—C13120.0 (3)
O1i—Sb1—C8i86.72 (10)C9—C8—Sb1119.3 (2)
O1—Sb1—C8i91.79 (10)C13—C8—Sb1120.7 (2)
C14—Sb1—C8i121.67 (8)C8—C9—C10119.5 (3)
O1i—Sb1—C891.79 (10)C8—C9—H9120.2
O1—Sb1—C886.72 (10)C10—C9—H9120.2
C14—Sb1—C8121.67 (8)C11—C10—C9120.3 (3)
C8i—Sb1—C8116.65 (16)C11—C10—H10119.9
C1—N1—O1114.4 (3)C9—C10—H10119.9
N1—O1—Sb1111.27 (16)C12—C11—C10120.3 (3)
C3—O2—H2109.5C12—C11—H11119.9
N1—C1—C2121.1 (3)C10—C11—H11119.9
N1—C1—H1119.4C11—C12—C13120.2 (3)
C2—C1—H1119.4C11—C12—H12119.9
C7—C2—C3118.3 (3)C13—C12—H12119.9
C7—C2—C1119.7 (3)C8—C13—C12119.7 (3)
C3—C2—C1122.0 (3)C8—C13—H13120.2
O2—C3—C4118.3 (3)C12—C13—H13120.2
O2—C3—C2122.0 (3)C15i—C14—C15118.4 (5)
C4—C3—C2119.8 (4)C15i—C14—Sb1120.8 (2)
C5—C4—C3120.6 (4)C15—C14—Sb1120.8 (2)
C5—C4—H4119.7C14—C15—C16121.0 (5)
C3—C4—H4119.7C14—C15—H15119.5
C6—C5—C4120.3 (4)C16—C15—H15119.5
C6—C5—H5119.8C17—C16—C15118.1 (6)
C4—C5—H5119.8C17—C16—H16120.9
C5—C6—C7119.9 (4)C15—C16—H16120.9
C5—C6—H6120.1C16i—C17—C16123.4 (7)
C7—C6—H6120.1C16i—C17—H17118.3
C6—C7—C2121.1 (4)C16—C17—H17118.3
C1—N1—O1—Sb1160.6 (2)O1—Sb1—C8—C13−27.7 (2)
O1i—Sb1—O1—N1−132.17 (17)C14—Sb1—C8—C1361.9 (3)
C14—Sb1—O1—N147.83 (17)C8i—Sb1—C8—C13−118.1 (3)
C8i—Sb1—O1—N1−73.93 (19)C13—C8—C9—C101.5 (5)
C8—Sb1—O1—N1169.48 (19)Sb1—C8—C9—C10−176.3 (3)
O1—N1—C1—C2174.7 (3)C8—C9—C10—C11−0.8 (5)
N1—C1—C2—C7178.1 (3)C9—C10—C11—C12−0.3 (6)
N1—C1—C2—C3−3.6 (5)C10—C11—C12—C130.5 (6)
C7—C2—C3—O2179.2 (3)C9—C8—C13—C12−1.3 (5)
C1—C2—C3—O20.8 (5)Sb1—C8—C13—C12176.5 (2)
C7—C2—C3—C4−0.2 (5)C11—C12—C13—C80.2 (5)
C1—C2—C3—C4−178.6 (3)O1i—Sb1—C14—C15i38.99 (19)
O2—C3—C4—C5−179.0 (4)O1—Sb1—C14—C15i−141.01 (19)
C2—C3—C4—C50.4 (6)C8i—Sb1—C14—C15i−48.0 (2)
C3—C4—C5—C6−0.3 (7)C8—Sb1—C14—C15i132.0 (2)
C4—C5—C6—C70.0 (7)O1i—Sb1—C14—C15−141.01 (19)
C5—C6—C7—C20.2 (7)O1—Sb1—C14—C1538.99 (19)
C3—C2—C7—C6−0.1 (6)C8i—Sb1—C14—C15132.0 (2)
C1—C2—C7—C6178.3 (4)C8—Sb1—C14—C15−48.0 (2)
O1i—Sb1—C8—C9−27.5 (3)C15i—C14—C15—C16−0.3 (3)
O1—Sb1—C8—C9150.1 (3)Sb1—C14—C15—C16179.7 (3)
C14—Sb1—C8—C9−120.2 (2)C14—C15—C16—C170.5 (6)
C8i—Sb1—C8—C959.8 (2)C15—C16—C17—C16i−0.2 (3)
O1i—Sb1—C8—C13154.7 (2)
Symmetry codes: (i) −x+1, −y+3/2, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O2ii0.932.583.294 (5)134
O2—H2···N10.821.892.617 (4)146
Symmetry codes: (ii) −y+7/4, x+1/4, z+1/4.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O2i0.932.583.294 (5)134
O2—H2···N10.821.892.617 (4)146
Symmetry codes: (i) −y+7/4, x+1/4, z+1/4.
Acknowledgements top

We acknowledge the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (Y2008B48) for financial support.

references
References top

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