catena-Poly[lead(II)-bis-(μ-2-amino-1,3-benzothia-zole-6-carboxyl-ato)].

The title complex, [Pb(C(8)H(5)N(2)O(2)S)(2)](n), consists of one Pb(II) ion located on a crystallographic twofold axis and two symmetry-related 2-amino-1,3-benzothia-zole-6-carboxyl-ate (ABTC) ligands. The central Pb(II) ion has a (4 + 2) coordination by four O atoms of the two ABTC ligands and two weaker Pb-S bonding inter-actions (Pb-S secondary bonds) from S atoms of other two neighbouring ABTC ligands. These bonds link the metal ions into zigzag chains along the c axis, which, in turn, aggregate through π-π inter-actions [centroid-centroid distance = 3.7436 Å] between ABTC rings and N-H⋯O and N-H⋯N hydrogen bonds.

Related literature

For applications of benzothia­zole and its derivatives, see: Petkova et al. (2000 ▶); Leng et al. (2001 ▶); Karlsson et al. (2003 ▶); Ćaleta et al. (2009 ▶); Tzanopoulou et al. (2010 ▶). For the use of benzothia­zoles in building novel complexes, see: Vuoti et al. (2007 ▶); Zou et al. (2004 ▶); Ng et al. (2008 ▶); Chen et al. (2010 ▶); For our recent work on the design and synthesis of benzothia­zole derivatives, see: Fang et al. (2010 ▶); Lei et al. (2010 ▶). For secondary Pb—S bonds, see: Chan & Rossi (1997 ▶); Turner et al. (2008 ▶). For van der Waals radii, see: Bondi (1964 ▶). For (4 + 2) coordination, see: Chan & Rossi (1997 ▶); Calatayud et al. (2007 ▶); Turner et al. (2008 ▶); Pena-Hueso et al. (2008 ▶). For π–π inter­actions, see: Sredojević et al. (2010 ▶). For the preparation of the 2-amino­benzothia­zole-6-carb­oxy­lic acid ligand, see: Das et al. (2003 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

[Pb(C8H5N2O2S)2]

M = 593.59

Monoclinic,

a = 10.909 (2) Å

b = 4.8271 (10) Å

c = 15.980 (3) Å

β = 100.02 (3)°

V = 828.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 10.47 mm−1

T = 293 K

0.39 × 0.29 × 0.15 mm

Data collection

Rigaku Saturn 724 CCD area-detector diffractometer

Absorption correction: numerical (NUMABS; Higashi, 2000) ▶ T min = 0.378, T max = 1.000

6088 measured reflections

1890 independent reflections

1871 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.096

S = 1.11

1890 reflections

123 parameters

H-atom parameters constrained

Δρmax = 2.13 e Å−3

Δρmin = −2.56 e Å−3

Data collection: CrystalClear (Rigaku, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEX (McArdle, 1995 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810049330/bg2378sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810049330/bg2378Isup2.hkl

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

[Pb(C8H5N2O2S)2]	F(000) = 560
Mr = 593.59	Dx = 2.379 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 3030 reflections
a = 10.909 (2) Å	θ = 3.5–27.6°
b = 4.8271 (10) Å	µ = 10.47 mm−1
c = 15.980 (3) Å	T = 293 K
β = 100.02 (3)°	Prism, brown
V = 828.6 (3) Å3	0.39 × 0.29 × 0.15 mm
Z = 2

Rigaku Saturn 724 CCD area-detector diffractometer	1890 independent reflections
Radiation source: fine-focus sealed tube	1871 reflections with I > 2σ(I)
graphite	Rint = 0.075
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.5°
dtprofit.ref scans	h = −14→12
Absorption correction: numerical (NUMABS; Higashi, 2000)	k = −6→6
Tmin = 0.378, Tmax = 1.000	l = −20→20
6088 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.8091P] where P = (Fo2 + 2Fc2)/3
1890 reflections	(Δ/σ)max < 0.001
123 parameters	Δρmax = 2.13 e Å−3
0 restraints	Δρmin = −2.56 e Å−3

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

	x	y	z	Uiso*/Ueq
Pb1	0.5000	0.46437 (5)	0.7500	0.02893 (13)
S1	0.68171 (12)	−0.6475 (3)	0.43591 (9)	0.0341 (3)
N1	0.8579 (6)	−1.0111 (11)	0.4062 (4)	0.0358 (12)
H1A	0.9286	−1.0940	0.4177	0.043*
H1B	0.8061	−1.0545	0.3611	0.043*
N2	0.9003 (4)	−0.7340 (11)	0.5281 (3)	0.0314 (10)
O1	0.6764 (4)	0.1672 (12)	0.7523 (3)	0.0456 (12)
O2	0.5321 (4)	0.1587 (10)	0.6401 (3)	0.0400 (10)
C1	0.8286 (5)	−0.8158 (13)	0.4580 (3)	0.0293 (10)
C2	0.7228 (6)	−0.4520 (10)	0.5281 (4)	0.0269 (11)
C3	0.6541 (5)	−0.2540 (12)	0.5620 (3)	0.0293 (11)
H3	0.5754	−0.2021	0.5341	0.035*
C4	0.7070 (5)	−0.1345 (12)	0.6396 (3)	0.0303 (11)
C5	0.8264 (5)	−0.2125 (15)	0.6806 (4)	0.0382 (13)
H5	0.8603	−0.1325	0.7324	0.046*
C6	0.8940 (6)	−0.4066 (16)	0.6445 (4)	0.0401 (14)
H6	0.9740	−0.4530	0.6712	0.048*
C7	0.8425 (6)	−0.5332 (12)	0.5682 (4)	0.0301 (12)
C8	0.6357 (6)	0.0758 (12)	0.6796 (4)	0.0295 (11)

	U11	U22	U33	U12	U13	U23
Pb1	0.03445 (19)	0.02334 (18)	0.0291 (2)	0.000	0.00589 (12)	0.000
S1	0.0295 (6)	0.0391 (8)	0.0308 (7)	0.0058 (6)	−0.0030 (5)	−0.0049 (6)
N1	0.033 (3)	0.042 (3)	0.030 (3)	0.005 (2)	−0.001 (2)	−0.010 (2)
N2	0.0270 (19)	0.036 (3)	0.030 (2)	0.0052 (19)	0.0017 (17)	−0.0053 (19)
O1	0.052 (3)	0.055 (3)	0.028 (2)	0.021 (2)	0.0025 (18)	−0.007 (2)
O2	0.034 (2)	0.042 (3)	0.042 (2)	0.0081 (19)	0.0009 (17)	−0.013 (2)
C1	0.026 (2)	0.033 (3)	0.029 (2)	0.004 (2)	0.0043 (19)	0.003 (2)
C2	0.028 (3)	0.027 (3)	0.025 (3)	−0.0007 (19)	0.002 (2)	0.0008 (19)
C3	0.026 (2)	0.030 (3)	0.032 (3)	0.003 (2)	0.0063 (19)	0.005 (2)
C4	0.032 (2)	0.028 (3)	0.032 (3)	0.005 (2)	0.009 (2)	0.000 (2)
C5	0.035 (3)	0.050 (4)	0.027 (3)	0.008 (3)	0.000 (2)	−0.009 (3)
C6	0.032 (3)	0.050 (3)	0.034 (3)	0.012 (3)	−0.005 (2)	−0.009 (3)
C7	0.029 (3)	0.032 (3)	0.029 (3)	0.005 (2)	0.004 (2)	0.001 (2)
C8	0.037 (3)	0.025 (2)	0.030 (3)	0.002 (2)	0.014 (2)	0.003 (2)

Pb1—O2	2.366 (4)	N2—C7	1.375 (7)
Pb1—O2i	2.366 (4)	O1—C8	1.251 (8)
Pb1—O1i	2.395 (5)	O2—C8	1.259 (8)
Pb1—O1	2.395 (5)	C2—C3	1.382 (8)
Pb1—C8	2.749 (6)	C2—C7	1.406 (8)
Pb1—C8i	2.749 (6)	C3—C4	1.399 (8)
Pb1—S1ii	3.3894 (17)	C3—H3	0.9300
Pb1—S1iii	3.3894 (17)	C4—C5	1.404 (8)
S1—C2	1.741 (6)	C4—C8	1.489 (8)
S1—C1	1.776 (5)	C5—C6	1.378 (9)
N1—C1	1.330 (8)	C5—H5	0.9300
N1—H1A	0.8600	C6—C7	1.392 (9)
N1—H1B	0.8600	C6—H6	0.9300
N2—C1	1.310 (7)
O2—Pb1—O2i	102.8 (3)	H1A—N1—H1B	120.0
O2—Pb1—O1i	80.64 (17)	C1—N2—C7	110.9 (5)
O2i—Pb1—O1i	54.26 (15)	C8—O1—Pb1	92.4 (4)
O2—Pb1—O1	54.26 (15)	C8—O2—Pb1	93.6 (4)
O2i—Pb1—O1	80.64 (17)	N2—C1—N1	125.0 (5)
O1i—Pb1—O1	106.4 (3)	N2—C1—S1	114.6 (4)
O2—Pb1—C8	27.21 (17)	N1—C1—S1	120.4 (4)
O2i—Pb1—C8	92.19 (17)	C3—C2—C7	122.5 (5)
O1i—Pb1—C8	94.21 (19)	C3—C2—S1	129.0 (5)
O1—Pb1—C8	27.04 (17)	C7—C2—S1	108.5 (4)
O2—Pb1—C8i	92.19 (17)	C2—C3—C4	117.7 (5)
O2i—Pb1—C8i	27.21 (17)	C2—C3—H3	121.2
O1i—Pb1—C8i	27.04 (17)	C4—C3—H3	121.2
O1—Pb1—C8i	94.21 (19)	C3—C4—C5	120.6 (5)
C8—Pb1—C8i	93.9 (2)	C3—C4—C8	119.7 (5)
O2—Pb1—S1ii	132.35 (10)	C5—C4—C8	119.7 (5)
O2i—Pb1—S1ii	69.61 (11)	C6—C5—C4	120.5 (6)
O1i—Pb1—S1ii	121.04 (10)	C6—C5—H5	119.7
O1—Pb1—S1ii	78.27 (11)	C4—C5—H5	119.7
C8—Pb1—S1ii	105.21 (14)	C5—C6—C7	120.1 (6)
C8i—Pb1—S1ii	95.37 (14)	C5—C6—H6	120.0
O2—Pb1—S1iii	69.61 (11)	C7—C6—H6	120.0
O2i—Pb1—S1iii	132.35 (11)	N2—C7—C6	124.8 (6)
O1i—Pb1—S1iii	78.27 (11)	N2—C7—C2	116.7 (6)
O1—Pb1—S1iii	121.04 (10)	C6—C7—C2	118.6 (6)
C8—Pb1—S1iii	95.37 (14)	O1—C8—O2	119.7 (5)
C8i—Pb1—S1iii	105.21 (14)	O1—C8—C4	120.8 (6)
S1ii—Pb1—S1iii	149.76 (6)	O2—C8—C4	119.5 (6)
C2—S1—C1	89.4 (3)	O1—C8—Pb1	60.5 (3)
C1—N1—H1A	120.0	O2—C8—Pb1	59.2 (3)
C1—N1—H1B	120.0	C4—C8—Pb1	178.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1iv	0.86	2.11	2.973 (7)	179
N1—H1A···N2v	0.86	2.09	2.934 (7)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1i	0.86	2.11	2.973 (7)	179
N1—H1A⋯N2ii	0.86	2.09	2.934 (7)	168

Symmetry codes: (i) ; (ii) .