(Z)-Methyl 4-(1,3-benzothia-zol-2-yl-sulfan-yl)-2-(methoxy-imino)-3-oxo-butanoate.

In the mol-ecular structure of the title compound, C(13)H(12)N(2)O(4)S(2), there is a dihedral angle of 0.41 (13)° between the benzene and thia-zole rings. In the crystal, inversion dimers linked by two C-H⋯O inter-actions together with π-π stacking between the parallel benzene rings of adjacent mol-ecules [centroid-centroid distance = 3.673 (2) Å].

Related literature

For general background to benzothia­zole derivatives and their biological activities, see: Bradshaw et al. (2008 ▶); Moharram (1990 ▶); Spillane et al. (2007 ▶).

Experimental

Crystal data

C13H12N2O4S2

M = 324.39

Triclinic,

a = 8.019 (3) Å

b = 10.037 (4) Å

c = 10.662 (5) Å

α = 76.44 (2)°

β = 67.997 (14)°

γ = 74.964 (15)°

V = 759.3 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 293 (2) K

0.22 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.913, T max = 0.939

7739 measured reflections

2620 independent reflections

2278 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.101

S = 1.10

2620 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040658/at2688sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040658/at2688Isup2.hkl

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

C13H12N2O4S2	Z = 2
Mr = 324.39	F(000) = 336
Triclinic, P1	Dx = 1.419 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.019 (3) Å	Cell parameters from 2679 reflections
b = 10.037 (4) Å	θ = 2.1–25.0°
c = 10.662 (5) Å	µ = 0.37 mm−1
α = 76.44 (2)°	T = 293 K
β = 67.997 (14)°	Block, colourless
γ = 74.964 (15)°	0.22 × 0.19 × 0.18 mm
V = 759.3 (6) Å3

Bruker SMART CCD area-detector diffractometer	2620 independent reflections
Radiation source: fine-focus sealed tube	2278 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
Tmin = 0.913, Tmax = 0.939	k = −11→11
7739 measured reflections	l = −12→12

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0551P)2 + 0.1857P] where P = (Fo2 + 2Fc2)/3
2620 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.26 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
C1	0.2301 (4)	0.0381 (3)	0.4741 (3)	0.0665 (7)
H1	0.1206	0.0298	0.5455	0.080*
C2	0.3264 (5)	−0.0698 (2)	0.3972 (3)	0.0788 (9)
H2	0.2803	−0.1514	0.4185	0.095*
C3	0.4890 (4)	−0.0581 (3)	0.2898 (3)	0.0735 (8)
H3	0.5497	−0.1320	0.2407	0.088*
C4	0.5617 (4)	0.0593 (3)	0.2549 (3)	0.0635 (6)
H4	0.6707	0.0670	0.1829	0.076*
C5	0.4664 (3)	0.1679 (2)	0.3314 (2)	0.0472 (5)
C6	0.3029 (3)	0.1583 (2)	0.4407 (2)	0.0452 (5)
C7	0.3251 (3)	0.3681 (2)	0.45184 (18)	0.0387 (4)
C8	0.0771 (3)	0.5086 (2)	0.65173 (19)	0.0436 (5)
H8A	0.0138	0.5988	0.6798	0.052*
H8B	−0.0068	0.4706	0.6302	0.052*
C9	0.1277 (3)	0.41269 (19)	0.76915 (19)	0.0399 (4)
C10	−0.0218 (3)	0.3515 (2)	0.88308 (19)	0.0403 (4)
C11	0.0216 (3)	0.2738 (2)	1.0097 (2)	0.0443 (5)
C12	−0.4696 (3)	0.3219 (3)	0.9528 (3)	0.0694 (7)
H12A	−0.5552	0.2765	1.0303	0.104*
H12B	−0.4454	0.2809	0.8734	0.104*
H12C	−0.5204	0.4195	0.9369	0.104*
C13	0.1207 (5)	0.0538 (3)	1.1217 (3)	0.0890 (9)
H13A	0.1554	−0.0424	1.1090	0.134*
H13B	0.0174	0.0646	1.2040	0.134*
H13C	0.2215	0.0828	1.1287	0.134*
N1	0.2241 (2)	0.27441 (17)	0.50850 (16)	0.0448 (4)
N2	−0.1769 (2)	0.36936 (18)	0.86710 (16)	0.0451 (4)
O1	0.28034 (19)	0.38332 (16)	0.77643 (15)	0.0530 (4)
O2	0.0143 (3)	0.32938 (19)	1.09837 (17)	0.0774 (5)
O3	0.0721 (2)	0.13890 (16)	1.00578 (16)	0.0638 (4)
O4	−0.30078 (19)	0.30477 (17)	0.97942 (15)	0.0568 (4)
S1	0.52463 (7)	0.32799 (6)	0.31355 (5)	0.05263 (18)
S2	0.27235 (7)	0.53273 (5)	0.50010 (5)	0.04578 (17)

	U11	U22	U33	U12	U13	U23
C1	0.0938 (19)	0.0544 (14)	0.0641 (14)	−0.0322 (13)	−0.0349 (13)	0.0011 (11)
C2	0.138 (3)	0.0375 (13)	0.093 (2)	−0.0260 (15)	−0.074 (2)	0.0004 (13)
C3	0.103 (2)	0.0500 (14)	0.0869 (19)	0.0087 (14)	−0.0594 (18)	−0.0267 (13)
C4	0.0734 (16)	0.0570 (14)	0.0702 (15)	0.0041 (12)	−0.0340 (13)	−0.0302 (12)
C5	0.0562 (12)	0.0444 (11)	0.0480 (11)	−0.0042 (9)	−0.0252 (10)	−0.0131 (9)
C6	0.0596 (12)	0.0385 (11)	0.0474 (11)	−0.0108 (9)	−0.0292 (10)	−0.0048 (8)
C7	0.0414 (10)	0.0418 (10)	0.0358 (9)	−0.0071 (8)	−0.0154 (8)	−0.0082 (8)
C8	0.0432 (11)	0.0490 (11)	0.0406 (10)	0.0008 (9)	−0.0174 (8)	−0.0155 (8)
C9	0.0420 (11)	0.0403 (10)	0.0438 (10)	0.0002 (8)	−0.0203 (8)	−0.0174 (8)
C10	0.0438 (10)	0.0413 (10)	0.0424 (10)	−0.0005 (8)	−0.0213 (8)	−0.0155 (8)
C11	0.0440 (11)	0.0488 (12)	0.0439 (10)	−0.0041 (9)	−0.0188 (9)	−0.0127 (9)
C12	0.0513 (13)	0.0842 (18)	0.0843 (17)	−0.0193 (12)	−0.0342 (13)	−0.0082 (14)
C13	0.127 (3)	0.0679 (18)	0.0844 (19)	−0.0117 (17)	−0.068 (2)	0.0130 (15)
N1	0.0484 (9)	0.0457 (10)	0.0433 (9)	−0.0136 (8)	−0.0150 (7)	−0.0077 (7)
N2	0.0446 (9)	0.0497 (10)	0.0449 (9)	−0.0089 (7)	−0.0185 (7)	−0.0088 (7)
O1	0.0438 (8)	0.0620 (9)	0.0594 (9)	−0.0054 (7)	−0.0272 (7)	−0.0094 (7)
O2	0.1180 (15)	0.0696 (11)	0.0605 (10)	0.0034 (10)	−0.0516 (10)	−0.0270 (9)
O3	0.0931 (12)	0.0467 (9)	0.0642 (10)	−0.0046 (8)	−0.0473 (9)	−0.0069 (7)
O4	0.0463 (8)	0.0745 (11)	0.0546 (9)	−0.0184 (7)	−0.0238 (7)	0.0000 (7)
S1	0.0523 (3)	0.0552 (4)	0.0485 (3)	−0.0167 (3)	−0.0037 (2)	−0.0193 (2)
S2	0.0515 (3)	0.0413 (3)	0.0472 (3)	−0.0109 (2)	−0.0144 (2)	−0.0131 (2)

C1—C6	1.389 (3)	C8—H8A	0.9700
C1—C2	1.397 (4)	C8—H8B	0.9700
C1—H1	0.9300	C9—O1	1.210 (2)
C2—C3	1.387 (4)	C9—C10	1.493 (3)
C2—H2	0.9300	C10—N2	1.279 (2)
C3—C4	1.362 (4)	C10—C11	1.506 (3)
C3—H3	0.9300	C11—O2	1.182 (2)
C4—C5	1.398 (3)	C11—O3	1.315 (3)
C4—H4	0.9300	C12—O4	1.445 (3)
C5—C6	1.398 (3)	C12—H12A	0.9600
C5—S1	1.736 (2)	C12—H12B	0.9600
C6—N1	1.397 (3)	C12—H12C	0.9600
C7—N1	1.291 (2)	C13—O3	1.450 (3)
C7—S2	1.745 (2)	C13—H13A	0.9600
C7—S1	1.753 (2)	C13—H13B	0.9600
C8—C9	1.507 (3)	C13—H13C	0.9600
C8—S2	1.800 (2)	N2—O4	1.386 (2)
C6—C1—C2	118.0 (3)	O1—C9—C10	118.71 (17)
C6—C1—H1	121.0	O1—C9—C8	124.10 (19)
C2—C1—H1	121.0	C10—C9—C8	117.19 (16)
C3—C2—C1	121.5 (2)	N2—C10—C9	118.18 (17)
C3—C2—H2	119.3	N2—C10—C11	124.72 (18)
C1—C2—H2	119.3	C9—C10—C11	117.11 (16)
C4—C3—C2	121.3 (2)	O2—C11—O3	125.40 (19)
C4—C3—H3	119.3	O2—C11—C10	123.41 (19)
C2—C3—H3	119.3	O3—C11—C10	111.17 (16)
C3—C4—C5	117.6 (3)	O4—C12—H12A	109.5
C3—C4—H4	121.2	O4—C12—H12B	109.5
C5—C4—H4	121.2	H12A—C12—H12B	109.5
C6—C5—C4	122.2 (2)	O4—C12—H12C	109.5
C6—C5—S1	109.43 (15)	H12A—C12—H12C	109.5
C4—C5—S1	128.4 (2)	H12B—C12—H12C	109.5
C1—C6—N1	124.8 (2)	O3—C13—H13A	109.5
C1—C6—C5	119.4 (2)	O3—C13—H13B	109.5
N1—C6—C5	115.76 (18)	H13A—C13—H13B	109.5
N1—C7—S2	124.48 (15)	O3—C13—H13C	109.5
N1—C7—S1	117.24 (15)	H13A—C13—H13C	109.5
S2—C7—S1	118.25 (11)	H13B—C13—H13C	109.5
C9—C8—S2	113.07 (14)	C7—N1—C6	109.26 (17)
C9—C8—H8A	109.0	C10—N2—O4	111.87 (15)
S2—C8—H8A	109.0	C11—O3—C13	115.94 (19)
C9—C8—H8B	109.0	N2—O4—C12	109.46 (16)
S2—C8—H8B	109.0	C5—S1—C7	88.31 (10)
H8A—C8—H8B	107.8	C7—S2—C8	98.95 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.93	2.55	3.398 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.93	2.55	3.398 (3)	152

Symmetry code: (i) .