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

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.031
• wR factor = 0.085
• Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.02
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         72

Alert level G
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.       9.49
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          2
            O1  -SB1 -O1  -N1   -132.17  0.17   7.564   1.555   1.555   1.555

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

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

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S1. 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.

Related literature

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

S2. 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.

S3. 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 U_iso(H) = 1.2 U_eq(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

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

	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)

Crystal data

[Sb(C6H5)3(C7H6NO2)2]	Dx = 1.451 Mg m^−3
Mr = 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) Å^3	Block, colourless
Z = 8	0.38 × 0.30 × 0.17 mm
F(000) = 2528

Data collection

Siemens SMART CCD area-detector diffractometer	3487 independent reflections
Radiation source: fine-focus sealed tube	2410 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→21
Tmin = 0.702, Tmax = 0.848	k = −9→22
17411 measured reflections	l = −26→26

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.030P)^2 + 9.4858P] where P = (Fo^2 + 2Fc^2)/3
3487 reflections	(Δ/σ)max = 0.001
178 parameters	Δρmax = 1.38 e Å^−3
0 restraints	Δρmin = −0.68 e Å^−3

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

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Sb1—O1^i	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—C8^i	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—C15^i	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—C16^i	1.359 (7)
C6—H6	0.9300	C17—H17	0.9300
O1^i—Sb1—O1	177.16 (12)	C6—C7—H7	119.4
O1^i—Sb1—C14	91.42 (6)	C2—C7—H7	119.4
O1—Sb1—C14	91.42 (6)	C9—C8—C13	120.0 (3)
O1^i—Sb1—C8^i	86.72 (10)	C9—C8—Sb1	119.3 (2)
O1—Sb1—C8^i	91.79 (10)	C13—C8—Sb1	120.7 (2)
C14—Sb1—C8^i	121.67 (8)	C8—C9—C10	119.5 (3)
O1^i—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)
C8^i—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)	C15^i—C14—C15	118.4 (5)
C4—C3—C2	119.8 (4)	C15^i—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	C16^i—C17—C16	123.4 (7)
C7—C6—H6	120.1	C16^i—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)
O1^i—Sb1—O1—N1	−132.17 (17)	C14—Sb1—C8—C13	61.9 (3)
C14—Sb1—O1—N1	47.83 (17)	C8^i—Sb1—C8—C13	−118.1 (3)
C8^i—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)	O1^i—Sb1—C14—C15^i	38.99 (19)
O2—C3—C4—C5	−179.0 (4)	O1—Sb1—C14—C15^i	−141.01 (19)
C2—C3—C4—C5	0.4 (6)	C8^i—Sb1—C14—C15^i	−48.0 (2)
C3—C4—C5—C6	−0.3 (7)	C8—Sb1—C14—C15^i	132.0 (2)
C4—C5—C6—C7	0.0 (7)	O1^i—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)	C8^i—Sb1—C14—C15	132.0 (2)
C1—C2—C7—C6	178.3 (4)	C8—Sb1—C14—C15	−48.0 (2)
O1^i—Sb1—C8—C9	−27.5 (3)	C15^i—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)
C8^i—Sb1—C8—C9	59.8 (2)	C15—C16—C17—C16^i	−0.2 (3)
O1^i—Sb1—C8—C13	154.7 (2)

Symmetry code: (i) −x+1, −y+3/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2^ii	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.