1,3-Benzothia-zole-oxalic acid (2/1).

The asymmetric unit of the title compound, C(7)H(5)NS·0.5C(2)H(2)O(4), contains one benzothia-zole mol-ecule and half an oxalic acid mol-ecule, the complete mol-ecule being generated by inversion symmetry. The benzothia-zole mol-ecule is essentially planar, with a maximum deviation of 0.007 (1) Å. In the crystal, the benzothia-zole mol-ecules inter-act with the oxalic acid mol-ecules via O-H⋯N and C-H⋯O hydrogen bonds generating R(2) (2)(8) (× 2) and R(4) (4)(10) motifs, thereby forming supra-molecular ribbons along [101].

Related literature

For background to the biological activity of benzothia­zoles, see: Bradshaw et al. (1998 ▶); Dögruer et al. (1998 ▶); Dash et al. (1980 ▶); Cox et al. (1982 ▶).

Experimental

Crystal data

C7H5NS·0.5C2H2O4

M = 180.20

Monoclinic,

a = 4.0231 (3) Å

b = 26.039 (2) Å

c = 8.5605 (6) Å

β = 116.064 (3)°

V = 805.58 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 296 K

0.62 × 0.40 × 0.04 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.811, T max = 0.985

10970 measured reflections

3204 independent reflections

2417 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.114

S = 1.04

3204 reflections

112 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032260/tk2778sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032260/tk2778Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032260/tk2778Isup3.cml

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

C7H5NS·0.5C2H2O4	F(000) = 372
Mr = 180.20	Dx = 1.486 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3803 reflections
a = 4.0231 (3) Å	θ = 2.8–32.6°
b = 26.039 (2) Å	µ = 0.35 mm−1
c = 8.5605 (6) Å	T = 296 K
β = 116.064 (3)°	Plate, brown
V = 805.58 (10) Å3	0.62 × 0.40 × 0.04 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	3204 independent reflections
Radiation source: fine-focus sealed tube	2417 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 33.9°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.811, Tmax = 0.985	k = −40→40
10970 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0557P)2 + 0.1124P] where P = (Fo2 + 2Fc2)/3
3204 reflections	(Δ/σ)max = 0.001
112 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S1	1.14317 (9)	0.875823 (14)	1.21487 (4)	0.04461 (11)
N1	1.0034 (3)	0.91965 (4)	0.92292 (13)	0.0385 (2)
C1	0.8353 (3)	0.84567 (4)	1.02665 (14)	0.0350 (2)
C2	0.6466 (4)	0.79950 (5)	1.00741 (19)	0.0448 (3)
H2A	0.6763	0.7800	1.1037	0.054*
C3	0.4144 (4)	0.78360 (5)	0.8411 (2)	0.0493 (3)
H3A	0.2881	0.7527	0.8252	0.059*
C4	0.3652 (4)	0.81302 (5)	0.69656 (18)	0.0468 (3)
H4A	0.2035	0.8017	0.5861	0.056*
C5	0.5516 (4)	0.85854 (5)	0.71444 (15)	0.0412 (3)
H5A	0.5187	0.8780	0.6176	0.049*
C6	0.7919 (3)	0.87487 (4)	0.88198 (14)	0.0329 (2)
C7	1.1947 (4)	0.92418 (5)	1.09000 (16)	0.0408 (3)
H7A	1.3510	0.9520	1.1395	0.049*
O1	0.7128 (3)	0.94803 (4)	0.47893 (12)	0.0584 (3)
O2	1.1410 (3)	0.98494 (4)	0.71853 (11)	0.0468 (2)
H1O2	1.064 (6)	0.9617 (8)	0.771 (3)	0.070*
C8	0.9467 (3)	0.97976 (4)	0.55062 (14)	0.0363 (2)

	U11	U22	U33	U12	U13	U23
S1	0.04724 (18)	0.0555 (2)	0.02518 (14)	−0.00784 (13)	0.01050 (12)	0.00106 (11)
N1	0.0444 (5)	0.0389 (5)	0.0286 (4)	−0.0058 (4)	0.0128 (4)	−0.0010 (3)
C1	0.0333 (5)	0.0404 (5)	0.0298 (5)	0.0001 (4)	0.0123 (4)	0.0004 (4)
C2	0.0428 (6)	0.0456 (6)	0.0446 (6)	−0.0034 (5)	0.0179 (5)	0.0069 (5)
C3	0.0464 (7)	0.0420 (6)	0.0565 (8)	−0.0098 (5)	0.0199 (6)	−0.0064 (6)
C4	0.0442 (6)	0.0515 (7)	0.0390 (6)	−0.0080 (5)	0.0131 (5)	−0.0136 (5)
C5	0.0447 (6)	0.0465 (6)	0.0281 (5)	−0.0032 (5)	0.0121 (5)	−0.0042 (4)
C6	0.0349 (5)	0.0351 (5)	0.0275 (5)	−0.0006 (4)	0.0126 (4)	−0.0019 (4)
C7	0.0442 (6)	0.0426 (6)	0.0315 (5)	−0.0082 (5)	0.0129 (5)	−0.0038 (4)
O1	0.0705 (7)	0.0600 (6)	0.0318 (4)	−0.0320 (5)	0.0108 (4)	−0.0010 (4)
O2	0.0557 (5)	0.0486 (5)	0.0255 (4)	−0.0169 (4)	0.0081 (4)	0.0029 (3)
C8	0.0400 (5)	0.0365 (5)	0.0265 (5)	−0.0049 (4)	0.0092 (4)	0.0009 (4)

S1—C7	1.7222 (13)	C4—C5	1.3748 (19)
S1—C1	1.7300 (12)	C4—H4A	0.9300
N1—C7	1.2979 (15)	C5—C6	1.3979 (15)
N1—C6	1.3944 (14)	C5—H5A	0.9300
C1—C2	1.3926 (17)	C7—H7A	0.9300
C1—C6	1.3972 (15)	O1—C8	1.1989 (14)
C2—C3	1.379 (2)	O2—C8	1.3068 (13)
C2—H2A	0.9300	O2—H1O2	0.89 (2)
C3—C4	1.394 (2)	C8—C8i	1.540 (2)
C3—H3A	0.9300
C7—S1—C1	89.19 (6)	C4—C5—C6	118.30 (12)
C7—N1—C6	110.72 (10)	C4—C5—H5A	120.9
C2—C1—C6	121.04 (11)	C6—C5—H5A	120.9
C2—C1—S1	129.19 (10)	N1—C6—C1	114.05 (10)
C6—C1—S1	109.76 (8)	N1—C6—C5	125.65 (10)
C3—C2—C1	117.92 (12)	C1—C6—C5	120.30 (11)
C3—C2—H2A	121.0	N1—C7—S1	116.28 (9)
C1—C2—H2A	121.0	N1—C7—H7A	121.9
C2—C3—C4	121.26 (12)	S1—C7—H7A	121.9
C2—C3—H3A	119.4	C8—O2—H1O2	108.3 (15)
C4—C3—H3A	119.4	O1—C8—O2	126.13 (11)
C5—C4—C3	121.16 (12)	O1—C8—C8i	122.24 (12)
C5—C4—H4A	119.4	O2—C8—C8i	111.63 (12)
C3—C4—H4A	119.4
C7—S1—C1—C2	179.27 (13)	C2—C1—C6—N1	−179.17 (11)
C7—S1—C1—C6	−0.42 (9)	S1—C1—C6—N1	0.55 (13)
C6—C1—C2—C3	−0.3 (2)	C2—C1—C6—C5	1.12 (18)
S1—C1—C2—C3	−179.91 (11)	S1—C1—C6—C5	−179.16 (9)
C1—C2—C3—C4	−0.9 (2)	C4—C5—C6—N1	179.48 (12)
C2—C3—C4—C5	1.1 (2)	C4—C5—C6—C1	−0.85 (19)
C3—C4—C5—C6	−0.3 (2)	C6—N1—C7—S1	0.05 (15)
C7—N1—C6—C1	−0.39 (15)	C1—S1—C7—N1	0.22 (11)
C7—N1—C6—C5	179.30 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1	0.89 (2)	1.80 (2)	2.6663 (15)	166 (2)
C5—H5A···O1	0.93	2.48	3.3263 (17)	151
C7—H7A···O2ii	0.93	2.48	3.4029 (18)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N1	0.89 (2)	1.80 (2)	2.6663 (15)	166 (2)
C5—H5A⋯O1	0.93	2.48	3.3263 (17)	151
C7—H7A⋯O2i	0.93	2.48	3.4029 (18)	170

Symmetry code: (i) .