Bis(5-bromo­pyridine-2-carboxyl­ato-κO)triphenyl­anti­mony(V)

Quan, L.; Yin, H.; Wang, D.

doi:10.1107/S1600536808033783

metal-organic compounds

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Volume 64| Part 12| December 2008| Page m1503

doi:10.1107/S1600536808033783

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Bis(5-bromopyridine-2-carboxylato-κO)triphenylantimony(V)

Li Quan,^a Handong Yin ^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 20 September 2008; accepted 16 October 2008; online 8 November 2008)

In the title compound, [Sb(C₆H₅)₃(C₆H₃BrNO₂)₂], the Sb center has a distorted trigonal–bipyramidal geometry, with two carboxylate O atoms of two 5-bromopyridine-2-carboxylate ligands in equatorial positions and three phenyl ligands in axial positions. The crystal structure is stabilized by C—H⋯Br hydrogen bonds and intermolecular C—Br⋯π interactions [C⋯π = 3.57 (1) Å].

Related literature

For the synthesis and structures of related triphenylantimony compounds, see: Yin et al. (2008 ); Chaudhari et al. (2007 ); Mahon et al. (1998 ); Quan et al. (2008 ).

Experimental

Crystal data

[Sb(C₆H₅)₃(C₆H₃BrNO₂)₂]
M_r = 755.06
Orthorhombic, F d d 2
a = 20.597 (2) Å
b = 13.057 (1) Å
c = 20.541 (2) Å
V = 5524.2 (9) Å³
Z = 8
Mo Kα radiation
μ = 3.93 mm⁻¹
T = 298 (2) K
0.43 × 0.37 × 0.20 mm

Data collection

Siemens SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.204, T_max = 0.460
5869 measured reflections
2564 independent reflections
1861 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.166
S = 1.01
2564 reflections
178 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.86 e Å⁻³
Absolute structure: Flack (1983 ), 1172 Friedel pairs
Flack parameter: 0.02 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Brⁱ	0.93	2.90	3.69 (2)	144
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

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: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033783/lx2073sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808033783/lx2073Isup2.hkl

checkCIF report

Comment top

The triphenylantimony compound containing the heterocyclic pyridine carboxylate skeleton show some potential biological activity (Yin et al., 2008) and we have synthesized the title compound (I) and report its crystal structure here.

As shown in Fig. 1, the Sb atom is five-coordinated by the three phenyl C atoms and the two carboxylate O atoms. The average distance of Sb—C (2.10 Å) in the (I) is shorter than the average distance of S—C (2.225 Å; Mahon et al., 1998). The average distance of Sb—O (2.146 Å) in the (I) is equal to the average distance of Sb—O (2.145 Å; Chaudhari et al., 2007). The crystal structure is stabilized by intermolecular C—H···Br hydrogen bonds (Fig. 2 and Table 1; symmetry code as in Fig. 2). In addition, the crystal structure exhibits C—Br···π interactions, with a C5—Br···Cgⁱⁱ separation of 3.57 (1) Å (Fig. 2; Cg is the centroid of the C7-C12 benzene ring, symmetry code as in Fig. 2).

Related literature top

For the synthesis and structures of related triphenylantimony compounds, see: Yin et al. (2008); Chaudhari et al. (2007); Mahon et al. (1998); Quan et al. (2008)

Experimental top

5-bromopyridine-2-carboxylic acid (0.061 g, 0.3 mmol) and sodium methoxide (0.6 ml, 0.3 mmol) was added to a stirring solution containing triphenylantimonydichloride (0.064 g, 0.15 mmol) in toluene (25 ml). After refluxing for 8 h, the colorless solution was obtained and then filtered. The solvent was gradually removed by evaporation under vacuum until the white solid is obtained. The solid was recrystallized from petroleum ether/dichoromethane (1:1) to give colorless crystals.

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: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (i) -x+1, -y+1, z.]
	Fig. 2. C—H···Br and C—Br···π interactions (dotted lines) in the title compound. Cg denotes the ring centroid. [Symmetry code: (i) -x+1/2, -y+1/2, z; (ii) x, y-1, z; (iii)-x+1/2, -y+1/2, z; (iv) -x+1, -y+1, z; (v) -x+1, -y+2, z; (vi) x+1/2, y+1/2, z.]

Bis(5-bromopyridine-2-carboxylato-κO)triphenylantimony(V) top

Crystal data top

[Sb(C₆H₅)₃(C₆H₃BrNO₂)₂]	F(000) = 2944
M_r = 755.06	D_x = 1.816 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: f 2 -2d	Cell parameters from 2025 reflections
a = 20.597 (2) Å	θ = 2.8–24.1°
b = 13.057 (1) Å	µ = 3.93 mm⁻¹
c = 20.541 (2) Å	T = 298 K
V = 5524.2 (9) Å³	Block, colorless
Z = 8	0.43 × 0.37 × 0.20 mm

Data collection top

Siemens SMART diffractometer	2564 independent reflections
Radiation source: fine-focus sealed tube	1861 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
Detector resolution: 20.0 pixels mm^-1	θ_max = 26.0°, θ_min = 2.1°
ϕ and ω scans	h = −23→25
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −16→12
T_min = 0.204, T_max = 0.460	l = −24→25
5869 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.166	w = 1/[σ²(F_o²) + (0.0963P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2564 reflections	Δρ_max = 1.02 e Å⁻³
178 parameters	Δρ_min = −0.86 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1172 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (3)

Crystal data top

[Sb(C₆H₅)₃(C₆H₃BrNO₂)₂]	V = 5524.2 (9) Å³
M_r = 755.06	Z = 8
Orthorhombic, Fdd2	Mo Kα radiation
a = 20.597 (2) Å	µ = 3.93 mm⁻¹
b = 13.057 (1) Å	T = 298 K
c = 20.541 (2) Å	0.43 × 0.37 × 0.20 mm

Data collection top

Siemens SMART diffractometer	2564 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1861 reflections with I > 2σ(I)
T_min = 0.204, T_max = 0.460	R_int = 0.081
5869 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.166	Δρ_max = 1.02 e Å⁻³
S = 1.01	Δρ_min = −0.86 e Å⁻³
2564 reflections	Absolute structure: Flack (1983), 1172 Friedel pairs
178 parameters	Absolute structure parameter: 0.02 (3)
1 restraint

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

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

	x	y	z	U_iso*/U_eq
Sb	0.5000	0.5000	0.64254 (4)	0.0395 (3)
Br	0.38657 (9)	−0.14610 (10)	0.69850 (11)	0.1021 (8)
N	0.4328 (6)	0.1462 (8)	0.6388 (6)	0.074 (3)
O1	0.4633 (4)	0.3464 (5)	0.6376 (4)	0.0449 (17)
O2	0.4672 (5)	0.3511 (7)	0.7460 (5)	0.064 (2)
C1	0.4568 (5)	0.3068 (9)	0.6937 (7)	0.049 (3)
C2	0.4353 (5)	0.1947 (9)	0.6944 (7)	0.052 (3)
C3	0.4223 (7)	0.1484 (13)	0.7532 (7)	0.065 (4)
H3	0.4257	0.1860	0.7916	0.078*
C4	0.4047 (7)	0.0490 (12)	0.7557 (8)	0.069 (4)
H4	0.3932	0.0178	0.7947	0.083*
C5	0.4046 (7)	−0.0025 (8)	0.6998 (8)	0.064 (4)
C6	0.4174 (9)	0.0468 (10)	0.6421 (10)	0.084 (5)
H6	0.4153	0.0094	0.6036	0.101*
C7	0.4109 (5)	0.5538 (8)	0.6790 (6)	0.044 (3)
C8	0.3959 (7)	0.5504 (11)	0.7467 (7)	0.065 (3)
H8	0.4256	0.5260	0.7770	0.078*
C9	0.3346 (8)	0.5853 (12)	0.7657 (9)	0.069 (5)
H9	0.3235	0.5854	0.8096	0.083*
C10	0.2904 (7)	0.6196 (10)	0.7200 (10)	0.071 (4)
H10	0.2495	0.6412	0.7335	0.085*
C11	0.3054 (7)	0.6225 (11)	0.6559 (9)	0.074 (4)
H11	0.2753	0.6456	0.6255	0.089*
C12	0.3667 (6)	0.5902 (9)	0.6362 (7)	0.058 (3)
H12	0.3776	0.5938	0.5923	0.070*
C13	0.5000	0.5000	0.5399 (8)	0.043 (4)
C14	0.5053 (6)	0.4088 (10)	0.5057 (6)	0.058 (3)
H14	0.5082	0.3467	0.5277	0.070*
C15	0.5062 (7)	0.4116 (12)	0.4393 (6)	0.068 (4)
H15	0.5112	0.3508	0.4162	0.082*
C16	0.5000	0.5000	0.4066 (10)	0.074 (6)
H16	0.5000	0.5000	0.3613	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb	0.0407 (5)	0.0310 (4)	0.0468 (5)	−0.0008 (5)	0.000	0.000
Br	0.1069 (13)	0.0400 (8)	0.159 (2)	−0.0140 (8)	0.0465 (13)	0.0023 (10)
N	0.118 (10)	0.045 (6)	0.058 (7)	−0.023 (6)	0.010 (8)	−0.004 (6)
O1	0.053 (4)	0.029 (4)	0.052 (5)	−0.004 (3)	−0.001 (4)	−0.002 (4)
O2	0.084 (6)	0.047 (5)	0.060 (5)	−0.011 (5)	−0.010 (5)	−0.005 (4)
C1	0.046 (6)	0.038 (6)	0.064 (8)	−0.001 (5)	−0.004 (6)	−0.004 (6)
C2	0.050 (7)	0.043 (6)	0.064 (8)	0.000 (5)	0.010 (7)	0.005 (6)
C3	0.078 (10)	0.060 (9)	0.057 (9)	−0.007 (7)	0.012 (8)	0.005 (7)
C4	0.070 (9)	0.052 (8)	0.086 (11)	0.009 (7)	0.001 (8)	0.017 (8)
C5	0.069 (9)	0.023 (6)	0.101 (12)	−0.005 (5)	0.014 (8)	0.003 (8)
C6	0.123 (13)	0.041 (7)	0.089 (10)	−0.010 (8)	0.028 (12)	−0.007 (9)
C7	0.039 (6)	0.029 (5)	0.064 (8)	−0.004 (4)	−0.004 (6)	−0.004 (5)
C8	0.075 (9)	0.067 (9)	0.053 (8)	−0.009 (8)	0.005 (7)	−0.009 (7)
C9	0.078 (10)	0.054 (8)	0.075 (10)	−0.010 (8)	0.046 (9)	−0.017 (7)
C10	0.053 (8)	0.049 (8)	0.111 (14)	0.002 (6)	0.026 (9)	−0.005 (8)
C11	0.052 (8)	0.066 (9)	0.105 (14)	0.008 (6)	−0.002 (9)	0.004 (8)
C12	0.056 (7)	0.052 (7)	0.068 (8)	−0.005 (5)	−0.007 (7)	−0.001 (6)
C13	0.052 (9)	0.022 (7)	0.056 (9)	0.009 (7)	0.000	0.000
C14	0.068 (8)	0.050 (7)	0.057 (8)	0.009 (6)	−0.006 (7)	0.003 (6)
C15	0.089 (10)	0.067 (9)	0.049 (7)	0.022 (7)	0.007 (8)	−0.014 (6)
C16	0.085 (14)	0.091 (16)	0.045 (10)	0.019 (12)	0.000	0.000

Geometric parameters (Å, º) top

Sb—C7	2.103 (11)	C7—C8	1.425 (19)
Sb—C7ⁱ	2.103 (11)	C8—C9	1.40 (2)
Sb—C13	2.108 (17)	C8—H8	0.9300
Sb—O1ⁱ	2.146 (7)	C9—C10	1.38 (2)
Sb—O1	2.146 (7)	C9—H9	0.9300
Br—C5	1.911 (10)	C10—C11	1.35 (2)
N—C2	1.309 (16)	C10—H10	0.9300
N—C6	1.337 (17)	C11—C12	1.39 (2)
O1—C1	1.270 (16)	C11—H11	0.9300
O2—C1	1.238 (16)	C12—H12	0.9300
C1—C2	1.529 (17)	C13—C14ⁱ	1.387 (16)
C2—C3	1.377 (19)	C13—C14	1.387 (16)
C3—C4	1.35 (2)	C14—C15	1.364 (19)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.33 (2)	C15—C16	1.342 (18)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.37 (2)	C16—C15ⁱ	1.342 (18)
C6—H6	0.9300	C16—H16	0.9300
C7—C12	1.352 (17)

C7—Sb—C7ⁱ	138.2 (7)	C12—C7—C8	120.0 (12)
C7—Sb—C13	110.9 (3)	C12—C7—Sb	118.2 (10)
C7ⁱ—Sb—C13	110.9 (3)	C8—C7—Sb	121.8 (10)
C7—Sb—O1ⁱ	90.7 (3)	C9—C8—C7	117.3 (15)
C7ⁱ—Sb—O1ⁱ	91.2 (4)	C9—C8—H8	121.4
C13—Sb—O1ⁱ	87.3 (2)	C7—C8—H8	121.4
C7—Sb—O1	91.2 (4)	C10—C9—C8	120.7 (14)
C7ⁱ—Sb—O1	90.7 (3)	C10—C9—H9	119.6
C13—Sb—O1	87.3 (2)	C8—C9—H9	119.6
O1ⁱ—Sb—O1	174.6 (5)	C11—C10—C9	121.2 (13)
C2—N—C6	115.8 (13)	C11—C10—H10	119.4
C1—O1—Sb	112.0 (7)	C9—C10—H10	119.4
O2—C1—O1	125.4 (11)	C10—C11—C12	118.8 (15)
O2—C1—C2	119.3 (12)	C10—C11—H11	120.6
O1—C1—C2	115.3 (11)	C12—C11—H11	120.6
N—C2—C3	123.1 (12)	C7—C12—C11	121.9 (15)
N—C2—C1	117.8 (11)	C7—C12—H12	119.1
C3—C2—C1	119.0 (13)	C11—C12—H12	119.1
C4—C3—C2	120.5 (14)	C14ⁱ—C13—C14	119.1 (16)
C4—C3—H3	119.7	C14ⁱ—C13—Sb	120.4 (8)
C2—C3—H3	119.7	C14—C13—Sb	120.4 (8)
C5—C4—C3	117.0 (14)	C15—C14—C13	119.0 (13)
C5—C4—H4	121.5	C15—C14—H14	120.5
C3—C4—H4	121.5	C13—C14—H14	120.5
C4—C5—C6	120.4 (12)	C16—C15—C14	121.5 (14)
C4—C5—Br	120.5 (12)	C16—C15—H15	119.2
C6—C5—Br	119.0 (11)	C14—C15—H15	119.2
N—C6—C5	123.0 (16)	C15ⁱ—C16—C15	119.8 (18)
N—C6—H6	118.5	C15ⁱ—C16—H16	120.1
C5—C6—H6	118.5	C15—C16—H16	120.1

C7—Sb—O1—C1	−72.0 (8)	C13—Sb—C7—C8	172.8 (9)
C7ⁱ—Sb—O1—C1	66.3 (8)	O1ⁱ—Sb—C7—C8	−99.8 (11)
C13—Sb—O1—C1	177.2 (7)	O1—Sb—C7—C8	85.2 (10)
Sb—O1—C1—O2	3.2 (15)	C12—C7—C8—C9	0.4 (19)
Sb—O1—C1—C2	−176.0 (7)	Sb—C7—C8—C9	−178.2 (10)
C6—N—C2—C3	−1 (2)	C7—C8—C9—C10	1 (2)
C6—N—C2—C1	176.3 (13)	C8—C9—C10—C11	−1 (2)
O2—C1—C2—N	−171.3 (13)	C9—C10—C11—C12	0 (2)
O1—C1—C2—N	7.8 (15)	C8—C7—C12—C11	−1.8 (19)
O2—C1—C2—C3	5.8 (17)	Sb—C7—C12—C11	176.8 (10)
O1—C1—C2—C3	−175.0 (12)	C10—C11—C12—C7	2 (2)
N—C2—C3—C4	−1 (2)	C7—Sb—C13—C14ⁱ	63.8 (7)
C1—C2—C3—C4	−178.4 (12)	C7ⁱ—Sb—C13—C14ⁱ	−116.2 (7)
C2—C3—C4—C5	4 (2)	O1ⁱ—Sb—C13—C14ⁱ	−25.9 (7)
C3—C4—C5—C6	−5 (2)	O1—Sb—C13—C14ⁱ	154.1 (7)
C3—C4—C5—Br	175.5 (11)	C7—Sb—C13—C14	−116.2 (7)
C2—N—C6—C5	0 (2)	C7ⁱ—Sb—C13—C14	63.8 (7)
C4—C5—C6—N	3 (3)	O1ⁱ—Sb—C13—C14	154.1 (7)
Br—C5—C6—N	−177.5 (13)	O1—Sb—C13—C14	−25.9 (7)
C7ⁱ—Sb—C7—C12	174.2 (9)	C14ⁱ—C13—C14—C15	1.0 (10)
C13—Sb—C7—C12	−5.8 (9)	Sb—C13—C14—C15	−179.0 (10)
O1ⁱ—Sb—C7—C12	81.6 (9)	C13—C14—C15—C16	−2 (2)
O1—Sb—C7—C12	−93.3 (9)	C14—C15—C16—C15ⁱ	1.1 (10)
C7ⁱ—Sb—C7—C8	−7.2 (9)

Symmetry code: (i) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Brⁱⁱ	0.93	2.90	3.69 (2)	144

Symmetry code: (ii) −x+1/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Sb(C₆H₅)₃(C₆H₃BrNO₂)₂]
M_r	755.06
Crystal system, space group	Orthorhombic, Fdd2
Temperature (K)	298
a, b, c (Å)	20.597 (2), 13.057 (1), 20.541 (2)
V (Å³)	5524.2 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.93
Crystal size (mm)	0.43 × 0.37 × 0.20

Data collection
Diffractometer	Siemens SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.204, 0.460
No. of measured, independent and observed [I > 2σ(I)] reflections	5869, 2564, 1861
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.166, 1.01
No. of reflections	2564
No. of parameters	178
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.86
Absolute structure	Flack (1983), 1172 Friedel pairs
Absolute structure parameter	0.02 (3)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Brⁱ	0.93	2.90	3.69 (2)	143.9

Symmetry code: (i) −x+1/2, −y+1/2, z.

Acknowledgements

We acknowledge the National Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (grant No. 2005ZX09) for financial support.

References

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