Chlorido(2-chloro­nicotinato)triphenyl­anti­mony(V)

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

doi:10.1107/S1600536808029632

Chlorido(2-chloronicotinato)triphenylantimony(V)

In the title complex, [Sb(C₆H₅)₃(C₆H₃ClNO₂)Cl], the Sb center has a close to ideal trigonal-bipyramidal geometry, with the phenyl ligands in equatorial positions and the chloride and a carboxylate O atom in axial positions. Weak C—H

O contacts generate dimeric units via crystallographic inversion centres.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808029632/si2109sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536808029632/si2109Isup2.hkl Contains datablock I

CCDC reference: 679196

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.024
wR factor = 0.072
Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.94

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.937
            Tmax scaled      0.547 Tmin scaled      0.516

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The triphenylantimony(V) acetylferroceneoxime structure shows some in vitro antitumor activity (Yin et al. 2008). The title compound may show similar activities. A similar compound was synthesized (Chaudhari et al.2007). The crystal structure of complex I (Fig. 1) consists of dimeric units, (Fig. 2) generated through weak intermolecular C—H···O hydrogen bonds via crystallographic inversion centres (Table 2). The sum of the equatorial angles C7—Sb1—C13, C13—Sb1—C19 and C19—Sb1—C7 is 359.98° and the corresponding axial angle Cl2—Sb1—O1 is 177.56 (6)° (Table 1). The distance Sb—O1 2.114 (2) Å is shorter than the range of short Sb—O distances 2.119 (3) - 2.133 (3) Å, and shorter than the range of the long Sb—O distances between 3.012 (6) and 3.112 (4) Å from related literature (Chaudhari et al.2007). The Sb1—O2 distance of 2.898 (2) Å in the title complex is shorter than the sum of the van der Waals radii for Sb and O (3.2 Å), but much longer than the covalent bond Sb–O1 (2.114 (2) Å). So it can be considered that atom O2 does not make any significant contact with the Sb1 atom.

Related literature top

For related structures, see: Yin et al. (2008); Chaudhari et al. (2007)

Experimental top

2-chloronicotinic acid (0.044 g, 0.4 mmol) and sodium methoxide (0.8 ml, 0.4 mmol) was added to a stirring solution containing triphenylantimonydichloride (0.172 g, 0.4 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 was 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) with atom labels and 50% probability displacement ellipsoids.
	Fig. 2. A dimer linked by C20—H20···O2ⁱ hydrogen bonds (dashed lines) (symmetry code i: 1 - x,-y,1 - z).

Chlorido(2-chloronicotinato)triphenylantimony(V) top

Crystal data top

[Sb(C₆H₅)₃(C₆H₃ClNO₂)Cl]	F(000) = 1080
M_r = 545.04	D_x = 1.635 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5771 reflections
a = 11.9580 (9) Å	θ = 2.3–28.0°
b = 15.4428 (18) Å	µ = 1.51 mm⁻¹
c = 12.0264 (15) Å	T = 298 K
β = 94.291 (2)°	Block, colorless
V = 2214.6 (4) Å³	0.45 × 0.41 × 0.40 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3893 independent reflections
Radiation source: fine-focus sealed tube	3149 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→14
T_min = 0.550, T_max = 0.584	k = −17→18
10922 measured reflections	l = −14→10

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0415P)² + 0.4912P] where P = (F_o² + 2F_c²)/3
3893 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Sb(C₆H₅)₃(C₆H₃ClNO₂)Cl]	V = 2214.6 (4) Å³
M_r = 545.04	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.9580 (9) Å	µ = 1.51 mm⁻¹
b = 15.4428 (18) Å	T = 298 K
c = 12.0264 (15) Å	0.45 × 0.41 × 0.40 mm
β = 94.291 (2)°

Data collection top

Bruker SMART CCD diffractometer	3893 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3149 reflections with I > 2σ(I)
T_min = 0.550, T_max = 0.584	R_int = 0.026
10922 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.00	Δρ_max = 0.52 e Å⁻³
3893 reflections	Δρ_min = −0.39 e Å⁻³
271 parameters

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

	x	y	z	U_iso*/U_eq
Sb1	0.523870 (16)	0.223556 (12)	0.600425 (16)	0.03369 (9)
Cl1	0.55909 (9)	−0.11472 (6)	0.80420 (9)	0.0663 (3)
Cl2	0.45726 (7)	0.27660 (6)	0.41124 (6)	0.0467 (2)
N1	0.6489 (3)	−0.0695 (2)	0.9960 (3)	0.0674 (9)
O1	0.58192 (17)	0.17341 (13)	0.75786 (17)	0.0412 (5)
O2	0.5294 (2)	0.04741 (15)	0.68384 (19)	0.0534 (6)
C1	0.5703 (2)	0.0892 (2)	0.7620 (3)	0.0389 (7)
C2	0.6110 (3)	−0.0368 (2)	0.8986 (3)	0.0472 (8)
C3	0.6124 (2)	0.0507 (2)	0.8723 (3)	0.0390 (7)
C4	0.6553 (3)	0.1057 (2)	0.9560 (3)	0.0526 (9)
H4	0.6581	0.1650	0.9431	0.063*
C5	0.6938 (3)	0.0727 (3)	1.0584 (3)	0.0671 (11)
H5	0.7220	0.1092	1.1153	0.081*
C6	0.6895 (4)	−0.0142 (3)	1.0742 (4)	0.0746 (13)
H6	0.7163	−0.0363	1.1431	0.090*
C7	0.5622 (3)	0.34849 (19)	0.6637 (3)	0.0382 (7)
C8	0.6477 (3)	0.3615 (2)	0.7465 (3)	0.0498 (9)
H8	0.6901	0.3151	0.7753	0.060*
C9	0.6690 (3)	0.4453 (2)	0.7860 (3)	0.0584 (10)
H9	0.7269	0.4549	0.8406	0.070*
C10	0.6060 (4)	0.5124 (2)	0.7453 (3)	0.0629 (11)
H10	0.6214	0.5680	0.7719	0.075*
C11	0.5199 (4)	0.4995 (2)	0.6655 (3)	0.0657 (11)
H11	0.4758	0.5459	0.6395	0.079*
C12	0.4988 (3)	0.4171 (2)	0.6237 (3)	0.0537 (9)
H12	0.4414	0.4084	0.5683	0.064*
C13	0.3560 (2)	0.1945 (2)	0.6294 (3)	0.0363 (7)
C14	0.3242 (3)	0.2102 (2)	0.7346 (3)	0.0527 (9)
H14	0.3771	0.2264	0.7914	0.063*
C15	0.2124 (3)	0.2015 (3)	0.7553 (3)	0.0649 (11)
H15	0.1895	0.2136	0.8259	0.078*
C16	0.1358 (3)	0.1752 (3)	0.6727 (3)	0.0584 (10)
H16	0.0609	0.1693	0.6872	0.070*
C17	0.1683 (3)	0.1575 (3)	0.5685 (3)	0.0612 (10)
H17	0.1158	0.1383	0.5131	0.073*
C18	0.2789 (3)	0.1682 (2)	0.5453 (3)	0.0510 (9)
H18	0.3010	0.1578	0.4740	0.061*
C19	0.6570 (3)	0.1635 (2)	0.5247 (2)	0.0388 (7)
C20	0.6410 (3)	0.0945 (2)	0.4541 (3)	0.0559 (9)
H20	0.5701	0.0701	0.4409	0.067*
C21	0.7306 (4)	0.0614 (3)	0.4028 (3)	0.0727 (12)
H21	0.7202	0.0144	0.3548	0.087*
C22	0.8339 (4)	0.0967 (3)	0.4217 (4)	0.0769 (14)
H22	0.8942	0.0735	0.3874	0.092*
C23	0.8497 (3)	0.1667 (3)	0.4913 (4)	0.0723 (13)
H23	0.9206	0.1913	0.5026	0.087*
C24	0.7621 (3)	0.2011 (3)	0.5444 (3)	0.0544 (9)
H24	0.7729	0.2482	0.5922	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb1	0.03589 (13)	0.02844 (13)	0.03649 (13)	−0.00131 (9)	0.00101 (9)	0.00020 (9)
Cl1	0.0809 (7)	0.0349 (5)	0.0805 (7)	−0.0049 (5)	−0.0123 (5)	0.0016 (5)
Cl2	0.0547 (5)	0.0472 (5)	0.0381 (4)	0.0028 (4)	0.0029 (4)	0.0067 (4)
N1	0.078 (2)	0.055 (2)	0.067 (2)	0.0044 (18)	−0.0095 (18)	0.0224 (18)
O1	0.0499 (12)	0.0300 (12)	0.0424 (12)	−0.0017 (10)	−0.0044 (10)	0.0024 (10)
O2	0.0722 (16)	0.0367 (13)	0.0488 (14)	−0.0085 (12)	−0.0122 (12)	0.0001 (11)
C1	0.0393 (17)	0.0341 (18)	0.0429 (18)	−0.0006 (14)	0.0007 (14)	−0.0014 (15)
C2	0.0437 (18)	0.043 (2)	0.055 (2)	0.0016 (16)	−0.0005 (16)	0.0041 (17)
C3	0.0362 (16)	0.0378 (18)	0.0423 (18)	0.0015 (14)	−0.0006 (13)	0.0010 (14)
C4	0.061 (2)	0.045 (2)	0.050 (2)	−0.0025 (17)	−0.0085 (17)	0.0012 (17)
C5	0.077 (3)	0.071 (3)	0.049 (2)	−0.002 (2)	−0.017 (2)	−0.001 (2)
C6	0.091 (3)	0.077 (3)	0.052 (2)	0.005 (3)	−0.018 (2)	0.017 (2)
C7	0.0446 (17)	0.0273 (16)	0.0438 (18)	−0.0015 (14)	0.0103 (15)	−0.0004 (14)
C8	0.061 (2)	0.037 (2)	0.051 (2)	−0.0001 (17)	−0.0046 (17)	−0.0006 (16)
C9	0.069 (2)	0.051 (2)	0.054 (2)	−0.012 (2)	−0.0057 (19)	−0.0107 (18)
C10	0.093 (3)	0.033 (2)	0.063 (3)	−0.009 (2)	0.007 (2)	−0.0060 (18)
C11	0.092 (3)	0.036 (2)	0.068 (3)	0.012 (2)	−0.005 (2)	−0.0024 (19)
C12	0.063 (2)	0.038 (2)	0.058 (2)	0.0060 (17)	−0.0044 (18)	−0.0056 (17)
C13	0.0349 (16)	0.0318 (17)	0.0420 (18)	0.0006 (13)	0.0026 (14)	0.0061 (13)
C14	0.048 (2)	0.066 (3)	0.045 (2)	−0.0009 (18)	0.0041 (16)	−0.0008 (17)
C15	0.055 (2)	0.087 (3)	0.055 (2)	0.000 (2)	0.0178 (19)	0.001 (2)
C16	0.0376 (18)	0.065 (3)	0.074 (3)	0.0008 (18)	0.0122 (19)	0.013 (2)
C17	0.0403 (19)	0.076 (3)	0.067 (3)	−0.0089 (19)	−0.0027 (18)	−0.002 (2)
C18	0.0430 (19)	0.062 (2)	0.048 (2)	−0.0040 (18)	0.0016 (16)	−0.0052 (18)
C19	0.0426 (17)	0.0341 (17)	0.0398 (17)	0.0059 (14)	0.0038 (14)	0.0010 (14)
C20	0.069 (2)	0.041 (2)	0.058 (2)	−0.0052 (18)	0.0049 (19)	−0.0097 (17)
C21	0.101 (3)	0.054 (3)	0.065 (3)	0.023 (3)	0.024 (2)	−0.009 (2)
C22	0.075 (3)	0.090 (4)	0.068 (3)	0.042 (3)	0.024 (2)	0.011 (3)
C23	0.041 (2)	0.101 (4)	0.075 (3)	0.012 (2)	0.004 (2)	0.006 (3)
C24	0.0442 (19)	0.064 (2)	0.055 (2)	0.0044 (18)	−0.0025 (17)	−0.0053 (18)

Geometric parameters (Å, º) top

Sb1—C19	2.107 (3)	C11—C12	1.385 (5)
Sb1—C13	2.111 (3)	C11—H11	0.9300
Sb1—C7	2.111 (3)	C12—H12	0.9300
Sb1—O1	2.114 (2)	C13—C14	1.369 (5)
Sb1—Cl2	2.4921 (8)	C13—C18	1.377 (4)
Cl1—C2	1.736 (4)	C14—C15	1.385 (5)
N1—C2	1.324 (4)	C14—H14	0.9300
N1—C6	1.335 (5)	C15—C16	1.361 (5)
O1—C1	1.309 (4)	C15—H15	0.9300
O2—C1	1.213 (4)	C16—C17	1.367 (5)
C1—C3	1.506 (4)	C16—H16	0.9300
C2—C3	1.389 (5)	C17—C18	1.382 (5)
C3—C4	1.386 (5)	C17—H17	0.9300
C4—C5	1.380 (5)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.367 (5)
C5—C6	1.356 (6)	C19—C24	1.390 (5)
C5—H5	0.9300	C20—C21	1.374 (5)
C6—H6	0.9300	C20—H20	0.9300
C7—C12	1.369 (5)	C21—C22	1.354 (6)
C7—C8	1.388 (4)	C21—H21	0.9300
C8—C9	1.394 (5)	C22—C23	1.371 (6)
C8—H8	0.9300	C22—H22	0.9300
C9—C10	1.351 (5)	C23—C24	1.373 (5)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.369 (5)	C24—H24	0.9300
C10—H10	0.9300

C19—Sb1—C13	137.38 (12)	C10—C11—C12	119.7 (4)
C19—Sb1—C7	114.05 (12)	C10—C11—H11	120.1
C13—Sb1—C7	108.55 (12)	C12—C11—H11	120.1
C19—Sb1—O1	91.02 (10)	C7—C12—C11	120.2 (3)
C13—Sb1—O1	91.53 (10)	C7—C12—H12	119.9
C7—Sb1—O1	87.95 (10)	C11—C12—H12	119.9
C19—Sb1—Cl2	87.14 (8)	C14—C13—C18	120.9 (3)
C13—Sb1—Cl2	88.72 (8)	C14—C13—Sb1	116.6 (2)
C7—Sb1—Cl2	94.27 (9)	C18—C13—Sb1	122.3 (2)
O1—Sb1—Cl2	177.56 (6)	C13—C14—C15	119.2 (4)
C2—N1—C6	117.5 (3)	C13—C14—H14	120.4
C1—O1—Sb1	111.67 (19)	C15—C14—H14	120.4
O2—C1—O1	122.5 (3)	C16—C15—C14	120.2 (4)
O2—C1—C3	124.1 (3)	C16—C15—H15	119.9
O1—C1—C3	113.4 (3)	C14—C15—H15	119.9
N1—C2—C3	124.3 (3)	C15—C16—C17	120.5 (3)
N1—C2—Cl1	113.3 (3)	C15—C16—H16	119.8
C3—C2—Cl1	122.4 (3)	C17—C16—H16	119.8
C4—C3—C2	116.2 (3)	C16—C17—C18	120.2 (3)
C4—C3—C1	118.6 (3)	C16—C17—H17	119.9
C2—C3—C1	125.2 (3)	C18—C17—H17	119.9
C5—C4—C3	120.1 (4)	C13—C18—C17	119.0 (3)
C5—C4—H4	119.9	C13—C18—H18	120.5
C3—C4—H4	119.9	C17—C18—H18	120.5
C6—C5—C4	118.5 (4)	C20—C19—C24	121.0 (3)
C6—C5—H5	120.7	C20—C19—Sb1	122.5 (3)
C4—C5—H5	120.7	C24—C19—Sb1	116.4 (2)
N1—C6—C5	123.3 (4)	C19—C20—C21	119.4 (4)
N1—C6—H6	118.3	C19—C20—H20	120.3
C5—C6—H6	118.3	C21—C20—H20	120.3
C12—C7—C8	119.9 (3)	C22—C21—C20	120.5 (4)
C12—C7—Sb1	118.8 (2)	C22—C21—H21	119.8
C8—C7—Sb1	121.3 (2)	C20—C21—H21	119.8
C7—C8—C9	119.0 (3)	C21—C22—C23	120.2 (4)
C7—C8—H8	120.5	C21—C22—H22	119.9
C9—C8—H8	120.5	C23—C22—H22	119.9
C10—C9—C8	120.4 (4)	C22—C23—C24	120.9 (4)
C10—C9—H9	119.8	C22—C23—H23	119.5
C8—C9—H9	119.8	C24—C23—H23	119.5
C9—C10—C11	120.8 (4)	C23—C24—C19	118.0 (4)
C9—C10—H10	119.6	C23—C24—H24	121.0
C11—C10—H10	119.6	C19—C24—H24	121.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2ⁱ	0.93	2.59	3.346 (4)	139

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Sb(C₆H₅)₃(C₆H₃ClNO₂)Cl]
M_r	545.04
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.9580 (9), 15.4428 (18), 12.0264 (15)
β (°)	94.291 (2)
V (Å³)	2214.6 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.45 × 0.41 × 0.40

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.550, 0.584
No. of measured, independent and observed [I > 2σ(I)] reflections	10922, 3893, 3149
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.071, 1.00
No. of reflections	3893
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.39

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

Selected geometric parameters (Å, º) top

Sb1—C19	2.107 (3)	Sb1—O1	2.114 (2)
Sb1—C13	2.111 (3)	Sb1—Cl2	2.4921 (8)
Sb1—C7	2.111 (3)

C19—Sb1—C13	137.38 (12)	C13—Sb1—C7	108.55 (12)
C19—Sb1—C7	114.05 (12)	O1—Sb1—Cl2	177.56 (6)