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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1438.
Published online 2009 October 28. doi:  10.1107/S1600536809043542
PMCID: PMC2971330

Bis(2-hydroxy­benzaldehyde oximato-κO)triphenyl­anti­mony(V)

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-m1438-scheme1.jpg

Experimental

Crystal data

  • [Sb(C6H5)3(C7H6NO2)2]
  • M r = 625.31
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-65-m1438-efi2.jpg
  • a = 16.6012 (15) Å
  • c = 20.775 (2) Å
  • V = 5725.6 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 1.00 mm−1
  • T = 298 K
  • 0.38 × 0.30 × 0.17 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.702, T max = 0.848
  • 17411 measured reflections
  • 3487 independent reflections
  • 2410 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.085
  • S = 1.09
  • 3487 reflections
  • 178 parameters
  • H-atom parameters constrained
  • Δρmax = 1.38 e Å−3
  • Δρmin = −0.68 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043542/gk2230sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043542/gk2230Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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.
Fig. 2.
View of the two-dimensional layer structure in the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

[Sb(C6H5)3(C7H6NO2)2]Dx = 1.451 Mg m3
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 mm1
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

Siemens SMART CCD area-detector diffractometer3487 independent reflections
Radiation source: fine-focus sealed tube2410 reflections with I > 2σ(I)
graphiteRint = 0.034
[var phi] 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

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 = 1.09w = 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 Å3
0 restraintsΔρmin = −0.68 e Å3

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2230).

References

  • Sharutin, V. V., Molokova, O. V., Sharutina, O. K., Gerasimenko, A. V. & Pushilin, M. A. (2004). Zh. Obshch. Khim.74, 1600–1607.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Wang, G. C., Xiao, J., Yu, L., Li, J. S., Cui, J. R., Wang, R. Q. & Ran, F. X. (2004). J. Organomet. Chem.689, 1631–1638.

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