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

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

doi:10.1107/S1600536809043542

metal-organic compounds

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Volume 65| Part 11| November 2009| Page m1438

https://doi.org/10.1107/S1600536809043542

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

Lei Dong,^a Handong Yin,^a ^* Liyuan Wen ^a and Daqi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 24 September 2009; accepted 22 October 2009; online 28 October 2009)

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 ); Sharutin et al. (2004 ).

Experimental

Crystal data

[Sb(C₆H₅)₃(C₇H₆NO₂)₂]
M_r = 625.31
Tetragonal, I 4₁ /a
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 ) 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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.085
S = 1.09
3487 reflections
178 parameters
H-atom parameters constrained
Δρ_max = 1.38 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O2ⁱ	0.93	2.58	3.294 (5)	134
O2—H2⋯N1	0.82	1.89	2.617 (4)	146
Symmetry code: (i) $[-y+{\script{7\over 4}}, x+{\script{1\over 4}}, z+{\script{1\over 4}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; 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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043542/gk2230Isup2.hkl

checkCIF report

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.

Structure description top

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

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

	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.

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

Crystal data top

[Sb(C₆H₅)₃(C₇H₆NO₂)₂]	D_x = 1.451 Mg m⁻³
M_r = 625.31	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 5826 reflections
Hall symbol: -I 4ad	θ = 2.5–25.5°
a = 16.6012 (15) Å	µ = 1.00 mm⁻¹
c = 20.775 (2) Å	T = 298 K
V = 5725.6 (9) Å³	Block, colourless
Z = 8	0.38 × 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 tube	2410 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 28.3°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
T_min = 0.702, T_max = 0.848	k = −9→22
17411 measured reflections	l = −26→26

Refinement top

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.030P)² + 9.4858P] where P = (F_o² + 2F_c²)/3
3487 reflections	(Δ/σ)_max = 0.001
178 parameters	Δρ_max = 1.38 e Å⁻³
0 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

[Sb(C₆H₅)₃(C₇H₆NO₂)₂]	Z = 8
M_r = 625.31	Mo Kα radiation
Tetragonal, I4₁/a	µ = 1.00 mm⁻¹
a = 16.6012 (15) Å	T = 298 K
c = 20.775 (2) Å	0.38 × 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)
T_min = 0.702, T_max = 0.848	R_int = 0.034
17411 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.09	Δρ_max = 1.38 e Å⁻³
3487 reflections	Δρ_min = −0.68 e Å⁻³
178 parameters

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

	x	y	z	U_iso*/U_eq
Sb1	0.5000	0.7500	0.977300 (13)	0.03630 (10)
N1	0.65745 (16)	0.80646 (15)	0.93840 (13)	0.0438 (6)
O1	0.62512 (13)	0.74876 (13)	0.97978 (10)	0.0442 (5)
O2	0.66631 (16)	0.89097 (18)	0.83231 (13)	0.0716 (8)
H2	0.6454	0.8611	0.8589	0.107*
C1	0.7300 (2)	0.8254 (2)	0.95055 (16)	0.0474 (8)
H1	0.7551	0.8043	0.9869	0.057*
C2	0.7748 (2)	0.8797 (2)	0.90850 (17)	0.0467 (8)
C3	0.7419 (2)	0.9098 (2)	0.85145 (18)	0.0515 (8)
C4	0.7874 (3)	0.9596 (2)	0.8126 (2)	0.0704 (11)
H4	0.7653	0.9799	0.7747	0.084*
C5	0.8650 (3)	0.9796 (3)	0.8293 (2)	0.0762 (13)
H5	0.8951	1.0130	0.8026	0.091*
C6	0.8981 (3)	0.9506 (3)	0.8848 (2)	0.0778 (13)
H6	0.9506	0.9643	0.8959	0.093*
C7	0.8535 (2)	0.9012 (3)	0.92426 (19)	0.0647 (10)
H7	0.8763	0.8819	0.9621	0.078*
C8	0.50453 (19)	0.64233 (17)	1.03043 (14)	0.0384 (7)
C9	0.4426 (2)	0.62433 (19)	1.07230 (15)	0.0477 (8)
H9	0.3979	0.6579	1.0751	0.057*
C10	0.4475 (3)	0.5556 (2)	1.11027 (17)	0.0573 (9)
H10	0.4062	0.5435	1.1389	0.069*
C11	0.5130 (3)	0.5054 (2)	1.10563 (17)	0.0572 (9)
H11	0.5159	0.4596	1.1313	0.069*
C12	0.5738 (2)	0.5225 (2)	1.06345 (18)	0.0543 (9)
H12	0.6178	0.4880	1.0603	0.065*
C13	0.5701 (2)	0.59106 (19)	1.02534 (16)	0.0458 (8)
H13	0.6114	0.6025	0.9965	0.055*
C14	0.5000	0.7500	0.8764 (2)	0.0523 (12)
C15	0.5554 (3)	0.7042 (2)	0.84211 (19)	0.0655 (11)
H15	0.5931	0.6734	0.8643	0.079*
C16	0.5554 (4)	0.7039 (4)	0.7751 (2)	0.0985 (19)
H16	0.5922	0.6729	0.7522	0.118*
C17	0.5000	0.7500	0.7441 (4)	0.102 (3)
H17	0.5000	0.7500	0.6993	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb1	0.03787 (17)	0.03277 (16)	0.03825 (16)	0.00025 (13)	0.000	0.000
N1	0.0412 (15)	0.0414 (14)	0.0487 (15)	−0.0016 (12)	0.0064 (12)	0.0021 (12)
O1	0.0393 (12)	0.0429 (12)	0.0506 (13)	0.0003 (10)	0.0072 (10)	0.0083 (10)
O2	0.0554 (16)	0.093 (2)	0.0665 (17)	−0.0152 (15)	−0.0083 (13)	0.0257 (15)
C1	0.0455 (19)	0.0501 (19)	0.0466 (18)	0.0021 (15)	0.0034 (15)	0.0023 (16)
C2	0.0446 (18)	0.0428 (18)	0.053 (2)	−0.0002 (15)	0.0048 (16)	−0.0019 (16)
C3	0.049 (2)	0.048 (2)	0.057 (2)	−0.0017 (16)	0.0054 (17)	0.0032 (17)
C4	0.067 (3)	0.071 (3)	0.074 (3)	−0.005 (2)	0.005 (2)	0.026 (2)
C5	0.068 (3)	0.068 (3)	0.093 (3)	−0.016 (2)	0.015 (2)	0.022 (2)
C6	0.055 (2)	0.082 (3)	0.096 (3)	−0.023 (2)	0.004 (2)	0.014 (3)
C7	0.054 (2)	0.075 (3)	0.065 (2)	−0.009 (2)	−0.0021 (19)	0.011 (2)
C8	0.0441 (17)	0.0323 (15)	0.0387 (16)	−0.0002 (13)	−0.0010 (13)	−0.0017 (13)
C9	0.052 (2)	0.0418 (18)	0.0489 (19)	0.0026 (15)	0.0063 (16)	−0.0012 (15)
C10	0.074 (3)	0.0462 (19)	0.052 (2)	−0.0065 (18)	0.0121 (18)	0.0057 (16)
C11	0.080 (3)	0.0347 (17)	0.057 (2)	−0.0026 (18)	−0.007 (2)	0.0049 (16)
C12	0.059 (2)	0.0369 (17)	0.067 (2)	0.0070 (16)	−0.0069 (19)	−0.0009 (17)
C13	0.0474 (19)	0.0372 (17)	0.0527 (19)	0.0004 (14)	0.0028 (16)	−0.0015 (15)
C14	0.069 (3)	0.048 (3)	0.041 (2)	−0.015 (2)	0.000	0.000
C15	0.079 (3)	0.064 (2)	0.054 (2)	−0.015 (2)	0.010 (2)	−0.0095 (19)
C16	0.127 (5)	0.105 (4)	0.064 (3)	−0.044 (4)	0.027 (3)	−0.030 (3)
C17	0.141 (8)	0.110 (7)	0.055 (4)	−0.065 (6)	0.000	0.000

Geometric parameters (Å, º) top

Sb1—O1ⁱ	2.078 (2)	C7—H7	0.9300
Sb1—O1	2.078 (2)	C8—C9	1.379 (4)
Sb1—C14	2.097 (5)	C8—C13	1.386 (4)
Sb1—C8ⁱ	2.102 (3)	C9—C10	1.390 (5)
Sb1—C8	2.102 (3)	C9—H9	0.9300
N1—C1	1.271 (4)	C10—C11	1.373 (5)
N1—O1	1.394 (3)	C10—H10	0.9300
O2—C3	1.353 (4)	C11—C12	1.367 (5)
O2—H2	0.8200	C11—H11	0.9300
C1—C2	1.459 (5)	C12—C13	1.388 (5)
C1—H1	0.9300	C12—H12	0.9300
C2—C7	1.394 (5)	C13—H13	0.9300
C2—C3	1.397 (5)	C14—C15ⁱ	1.389 (5)
C3—C4	1.381 (5)	C14—C15	1.389 (5)
C4—C5	1.375 (6)	C15—C16	1.393 (6)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.365 (6)	C16—C17	1.359 (7)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.375 (5)	C17—C16ⁱ	1.359 (7)
C6—H6	0.9300	C17—H17	0.9300

O1ⁱ—Sb1—O1	177.16 (12)	C6—C7—H7	119.4
O1ⁱ—Sb1—C14	91.42 (6)	C2—C7—H7	119.4
O1—Sb1—C14	91.42 (6)	C9—C8—C13	120.0 (3)
O1ⁱ—Sb1—C8ⁱ	86.72 (10)	C9—C8—Sb1	119.3 (2)
O1—Sb1—C8ⁱ	91.79 (10)	C13—C8—Sb1	120.7 (2)
C14—Sb1—C8ⁱ	121.67 (8)	C8—C9—C10	119.5 (3)
O1ⁱ—Sb1—C8	91.79 (10)	C8—C9—H9	120.2
O1—Sb1—C8	86.72 (10)	C10—C9—H9	120.2
C14—Sb1—C8	121.67 (8)	C11—C10—C9	120.3 (3)
C8ⁱ—Sb1—C8	116.65 (16)	C11—C10—H10	119.9
C1—N1—O1	114.4 (3)	C9—C10—H10	119.9
N1—O1—Sb1	111.27 (16)	C12—C11—C10	120.3 (3)
C3—O2—H2	109.5	C12—C11—H11	119.9
N1—C1—C2	121.1 (3)	C10—C11—H11	119.9
N1—C1—H1	119.4	C11—C12—C13	120.2 (3)
C2—C1—H1	119.4	C11—C12—H12	119.9
C7—C2—C3	118.3 (3)	C13—C12—H12	119.9
C7—C2—C1	119.7 (3)	C8—C13—C12	119.7 (3)
C3—C2—C1	122.0 (3)	C8—C13—H13	120.2
O2—C3—C4	118.3 (3)	C12—C13—H13	120.2
O2—C3—C2	122.0 (3)	C15ⁱ—C14—C15	118.4 (5)
C4—C3—C2	119.8 (4)	C15ⁱ—C14—Sb1	120.8 (2)
C5—C4—C3	120.6 (4)	C15—C14—Sb1	120.8 (2)
C5—C4—H4	119.7	C14—C15—C16	121.0 (5)
C3—C4—H4	119.7	C14—C15—H15	119.5
C6—C5—C4	120.3 (4)	C16—C15—H15	119.5
C6—C5—H5	119.8	C17—C16—C15	118.1 (6)
C4—C5—H5	119.8	C17—C16—H16	120.9
C5—C6—C7	119.9 (4)	C15—C16—H16	120.9
C5—C6—H6	120.1	C16ⁱ—C17—C16	123.4 (7)
C7—C6—H6	120.1	C16ⁱ—C17—H17	118.3
C6—C7—C2	121.1 (4)	C16—C17—H17	118.3

C1—N1—O1—Sb1	160.6 (2)	O1—Sb1—C8—C13	−27.7 (2)
O1ⁱ—Sb1—O1—N1	−132.17 (17)	C14—Sb1—C8—C13	61.9 (3)
C14—Sb1—O1—N1	47.83 (17)	C8ⁱ—Sb1—C8—C13	−118.1 (3)
C8ⁱ—Sb1—O1—N1	−73.93 (19)	C13—C8—C9—C10	1.5 (5)
C8—Sb1—O1—N1	169.48 (19)	Sb1—C8—C9—C10	−176.3 (3)
O1—N1—C1—C2	174.7 (3)	C8—C9—C10—C11	−0.8 (5)
N1—C1—C2—C7	178.1 (3)	C9—C10—C11—C12	−0.3 (6)
N1—C1—C2—C3	−3.6 (5)	C10—C11—C12—C13	0.5 (6)
C7—C2—C3—O2	179.2 (3)	C9—C8—C13—C12	−1.3 (5)
C1—C2—C3—O2	0.8 (5)	Sb1—C8—C13—C12	176.5 (2)
C7—C2—C3—C4	−0.2 (5)	C11—C12—C13—C8	0.2 (5)
C1—C2—C3—C4	−178.6 (3)	O1ⁱ—Sb1—C14—C15ⁱ	38.99 (19)
O2—C3—C4—C5	−179.0 (4)	O1—Sb1—C14—C15ⁱ	−141.01 (19)
C2—C3—C4—C5	0.4 (6)	C8ⁱ—Sb1—C14—C15ⁱ	−48.0 (2)
C3—C4—C5—C6	−0.3 (7)	C8—Sb1—C14—C15ⁱ	132.0 (2)
C4—C5—C6—C7	0.0 (7)	O1ⁱ—Sb1—C14—C15	−141.01 (19)
C5—C6—C7—C2	0.2 (7)	O1—Sb1—C14—C15	38.99 (19)
C3—C2—C7—C6	−0.1 (6)	C8ⁱ—Sb1—C14—C15	132.0 (2)
C1—C2—C7—C6	178.3 (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—C9	150.1 (3)	Sb1—C14—C15—C16	179.7 (3)
C14—Sb1—C8—C9	−120.2 (2)	C14—C15—C16—C17	0.5 (6)
C8ⁱ—Sb1—C8—C9	59.8 (2)	C15—C16—C17—C16ⁱ	−0.2 (3)
O1ⁱ—Sb1—C8—C13	154.7 (2)

Symmetry code: (i) −x+1, −y+3/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2ⁱⁱ	0.93	2.58	3.294 (5)	134
O2—H2···N1	0.82	1.89	2.617 (4)	146

Symmetry code: (ii) −y+7/4, x+1/4, z+1/4.

Experimental details

Crystal data
Chemical formula	[Sb(C₆H₅)₃(C₇H₆NO₂)₂]
M_r	625.31
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	298
a, c (Å)	16.6012 (15), 20.775 (2)
V (Å³)	5725.6 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.00
Crystal size (mm)	0.38 × 0.30 × 0.17

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.702, 0.848
No. of measured, independent and observed [I > 2σ(I)] reflections	17411, 3487, 2410
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.085, 1.09
No. of reflections	3487
No. of parameters	178
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.38, −0.68

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2ⁱ	0.93	2.58	3.294 (5)	134.2
O2—H2···N1	0.82	1.89	2.617 (4)	146.4

Symmetry code: (i) −y+7/4, x+1/4, z+1/4.

Acknowledgements

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

References

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