2-Ethyl-N-[(5-nitro-thio-phen-2-yl)methyl-idene]aniline.

In the title compound, C(13)H(12)N(2)O(2)S, the dihedral angle between the benzene and thio-phene rings is 36.72 (8)°. An inter-molecular C-H⋯π inter-action contributes to the stability of the crystal structure.

Related literature

For the biological properties of Schiff bases, see: Barton & Ollis (1979 ▶); Layer (1963 ▶); Ingold (1969 ▶); for their industrial properties, see: Taggi et al. (2002 ▶) and for their reaction properties, see: Aydoğan et al. (2001 ▶). For related structures, see: Ağar et al. (2010 ▶); Tanak et al. (2010 ▶); Demirtaş et al. (2009 ▶).

Experimental

Crystal data

C13H12N2O2S

M = 260.31

Monoclinic,

a = 11.3578 (4) Å

b = 7.4923 (2) Å

c = 14.9676 (6) Å

β = 99.589 (3)°

V = 1255.89 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.54 × 0.41 × 0.23 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.866, T max = 0.954

12190 measured reflections

2468 independent reflections

2195 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.087

S = 1.05

2468 reflections

176 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811024615/vm2106sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024615/vm2106Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024615/vm2106Isup3.cml

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

C13H12N2O2S	F(000) = 544
Mr = 260.31	Dx = 1.377 Mg m−3
Monoclinic, P21/c	Melting point = 385–387 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.3578 (4) Å	Cell parameters from 18861 reflections
b = 7.4923 (2) Å	θ = 1.8–28.0°
c = 14.9676 (6) Å	µ = 0.25 mm−1
β = 99.589 (3)°	T = 296 K
V = 1255.89 (7) Å3	Prism, yellow
Z = 4	0.54 × 0.41 × 0.23 mm

Stoe IPDS 2 diffractometer	2468 independent reflections
Radiation source: fine-focus sealed tube	2195 reflections with I > 2σ(I)
graphite	Rint = 0.040
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.8°
rotation method scans	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.866, Tmax = 0.954	l = −18→18
12190 measured reflections

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0438P)2 + 0.2213P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2468 reflections	Δρmax = 0.14 e Å−3
176 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0197 (19)

Experimental. 256 frames, detector distance = 100 mm

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
C13	0.75353 (12)	0.1347 (2)	0.42892 (10)	0.0489 (3)
H9	0.5748 (13)	0.056 (2)	0.1442 (11)	0.051 (4)*
H8	0.2532 (19)	−0.043 (3)	0.2366 (14)	0.085 (6)*
H7	0.243 (2)	0.157 (3)	0.2581 (16)	0.096 (7)*
S1	0.60815 (3)	0.17034 (5)	0.38059 (2)	0.05021 (14)
N1	0.44485 (10)	0.15763 (16)	0.20080 (8)	0.0464 (3)
C1	0.36158 (12)	0.16196 (19)	0.11890 (9)	0.0457 (3)
C5	0.16094 (14)	0.1298 (2)	0.04281 (11)	0.0600 (4)
H5	0.0815	0.1006	0.0433	0.072*
C11	0.75953 (12)	0.0594 (2)	0.28326 (10)	0.0534 (4)
H11	0.7928	0.0215	0.2338	0.064*
C2	0.39465 (14)	0.2164 (2)	0.03818 (10)	0.0567 (4)
H2	0.4738	0.2464	0.0368	0.068*
C6	0.24197 (12)	0.11916 (19)	0.12317 (10)	0.0482 (3)
N2	0.78998 (12)	0.1655 (2)	0.52375 (9)	0.0621 (4)
O2	0.89564 (11)	0.1458 (2)	0.55569 (9)	0.0861 (4)
C10	0.64167 (12)	0.10510 (19)	0.27810 (9)	0.0453 (3)
C12	0.82434 (12)	0.0758 (2)	0.37105 (11)	0.0550 (4)
H12	0.9051	0.0496	0.3873	0.066*
C4	0.19440 (16)	0.1820 (3)	−0.03736 (11)	0.0686 (5)
H4	0.1378	0.1873	−0.0899	0.082*
C7	0.20824 (14)	0.0661 (3)	0.21248 (12)	0.0601 (4)
O1	0.71418 (13)	0.2089 (2)	0.56818 (9)	0.0905 (5)
C3	0.31134 (16)	0.2266 (3)	−0.04023 (11)	0.0659 (4)
H3	0.3339	0.2632	−0.0943	0.079*
C8	0.07793 (16)	0.0419 (4)	0.21480 (16)	0.0947 (7)
H8A	0.0672	0.0083	0.2748	0.142*
H8B	0.0465	−0.0500	0.1728	0.142*
H8C	0.0366	0.1518	0.1982	0.142*
C9	0.55012 (12)	0.10376 (19)	0.19795 (10)	0.0472 (3)

	U11	U22	U33	U12	U13	U23
C13	0.0404 (7)	0.0530 (8)	0.0504 (8)	0.0000 (6)	−0.0013 (6)	0.0022 (6)
S1	0.0381 (2)	0.0632 (3)	0.0480 (2)	0.00633 (15)	0.00307 (13)	0.00008 (16)
N1	0.0417 (6)	0.0505 (7)	0.0444 (6)	−0.0007 (5)	−0.0007 (5)	0.0011 (5)
C1	0.0440 (7)	0.0468 (7)	0.0433 (7)	0.0034 (6)	−0.0012 (5)	−0.0047 (6)
C5	0.0461 (8)	0.0682 (10)	0.0608 (9)	0.0012 (7)	−0.0058 (7)	−0.0117 (8)
C11	0.0429 (7)	0.0630 (9)	0.0541 (8)	0.0059 (7)	0.0078 (6)	0.0004 (7)
C2	0.0510 (8)	0.0697 (10)	0.0476 (8)	0.0040 (7)	0.0034 (6)	0.0004 (7)
C6	0.0449 (7)	0.0463 (7)	0.0507 (8)	0.0035 (6)	0.0003 (6)	−0.0065 (6)
N2	0.0560 (8)	0.0724 (9)	0.0530 (7)	0.0014 (6)	−0.0050 (6)	−0.0027 (6)
O2	0.0582 (7)	0.1187 (11)	0.0706 (8)	−0.0005 (7)	−0.0210 (6)	−0.0045 (8)
C10	0.0404 (7)	0.0454 (7)	0.0488 (7)	0.0006 (5)	0.0036 (5)	0.0028 (6)
C12	0.0369 (7)	0.0635 (9)	0.0625 (9)	0.0047 (6)	0.0023 (6)	0.0036 (7)
C4	0.0644 (10)	0.0853 (12)	0.0482 (8)	0.0101 (8)	−0.0137 (7)	−0.0109 (8)
C7	0.0494 (8)	0.0670 (10)	0.0630 (9)	0.0006 (7)	0.0066 (7)	0.0042 (8)
O1	0.0784 (9)	0.1339 (13)	0.0568 (7)	0.0181 (8)	0.0037 (6)	−0.0176 (8)
C3	0.0673 (10)	0.0848 (12)	0.0429 (8)	0.0100 (9)	0.0014 (7)	0.0000 (8)
C8	0.0552 (10)	0.140 (2)	0.0904 (14)	−0.0003 (12)	0.0176 (10)	0.0205 (14)
C9	0.0457 (7)	0.0493 (8)	0.0451 (7)	0.0005 (6)	0.0034 (6)	0.0006 (6)

C13—C12	1.351 (2)	C6—C7	1.504 (2)
C13—N2	1.430 (2)	N2—O1	1.2164 (19)
C13—S1	1.7097 (14)	N2—O2	1.2245 (17)
S1—C10	1.7122 (15)	C10—C9	1.4508 (19)
N1—C9	1.2694 (18)	C12—H12	0.9300
N1—C1	1.4185 (17)	C4—C3	1.377 (3)
C1—C2	1.385 (2)	C4—H4	0.9300
C1—C6	1.4077 (19)	C7—C8	1.497 (2)
C5—C4	1.375 (3)	C7—H8	1.00 (2)
C5—C6	1.390 (2)	C7—H7	1.00 (2)
C5—H5	0.9300	C3—H3	0.9300
C11—C10	1.3714 (19)	C8—H8A	0.9600
C11—C12	1.400 (2)	C8—H8B	0.9600
C11—H11	0.9300	C8—H8C	0.9600
C2—C3	1.382 (2)	C9—H9	0.963 (16)
C2—H2	0.9300
C12—C13—N2	125.78 (13)	C9—C10—S1	120.47 (10)
C12—C13—S1	114.58 (11)	C13—C12—C11	110.75 (13)
N2—C13—S1	119.63 (11)	C13—C12—H12	124.6
C13—S1—C10	89.50 (7)	C11—C12—H12	124.6
C9—N1—C1	118.32 (12)	C5—C4—C3	120.31 (14)
C2—C1—C6	120.72 (13)	C5—C4—H4	119.8
C2—C1—N1	121.47 (13)	C3—C4—H4	119.8
C6—C1—N1	117.71 (12)	C8—C7—C6	116.85 (15)
C4—C5—C6	122.17 (15)	C8—C7—H8	109.9 (12)
C4—C5—H5	118.9	C6—C7—H8	110.3 (12)
C6—C5—H5	118.9	C8—C7—H7	110.3 (13)
C10—C11—C12	112.74 (14)	C6—C7—H7	107.2 (13)
C10—C11—H11	123.6	H8—C7—H7	101.0 (17)
C12—C11—H11	123.6	C4—C3—C2	119.19 (16)
C3—C2—C1	120.70 (15)	C4—C3—H3	120.4
C3—C2—H2	119.7	C2—C3—H3	120.4
C1—C2—H2	119.7	C7—C8—H8A	109.5
C5—C6—C1	116.91 (14)	C7—C8—H8B	109.5
C5—C6—C7	123.67 (14)	H8A—C8—H8B	109.5
C1—C6—C7	119.42 (13)	C7—C8—H8C	109.5
O1—N2—O2	123.75 (15)	H8A—C8—H8C	109.5
O1—N2—C13	118.15 (13)	H8B—C8—H8C	109.5
O2—N2—C13	118.10 (14)	N1—C9—C10	121.28 (14)
C11—C10—C9	127.10 (14)	N1—C9—H9	123.5 (9)
C11—C10—S1	112.43 (11)	C10—C9—H9	115.2 (9)
C12—C13—S1—C10	−0.24 (12)	C12—C11—C10—C9	179.87 (14)
N2—C13—S1—C10	−179.44 (13)	C12—C11—C10—S1	0.35 (17)
C9—N1—C1—C2	−39.8 (2)	C13—S1—C10—C11	−0.07 (12)
C9—N1—C1—C6	143.95 (14)	C13—S1—C10—C9	−179.63 (12)
C6—C1—C2—C3	−1.2 (2)	N2—C13—C12—C11	179.62 (14)
N1—C1—C2—C3	−177.40 (14)	S1—C13—C12—C11	0.47 (18)
C4—C5—C6—C1	−0.9 (2)	C10—C11—C12—C13	−0.5 (2)
C4—C5—C6—C7	178.76 (16)	C6—C5—C4—C3	−0.2 (3)
C2—C1—C6—C5	1.6 (2)	C5—C6—C7—C8	−6.3 (3)
N1—C1—C6—C5	177.94 (13)	C1—C6—C7—C8	173.42 (17)
C2—C1—C6—C7	−178.07 (15)	C5—C4—C3—C2	0.7 (3)
N1—C1—C6—C7	−1.8 (2)	C1—C2—C3—C4	0.0 (3)
C12—C13—N2—O1	−175.78 (17)	C1—N1—C9—C10	176.56 (12)
S1—C13—N2—O1	3.3 (2)	C11—C10—C9—N1	−176.47 (14)
C12—C13—N2—O2	3.8 (2)	S1—C10—C9—N1	3.0 (2)
S1—C13—N2—O2	−177.09 (13)

Cg1 is the centroid of the C10–C13/S1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H8···Cg1i	1.00 (2)	2.94 (2)	3.678 (2)	131.0 (15)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C13/S1 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H8⋯Cg1i	1.00 (2)	2.94 (2)	3.678 (2)	131.0 (15)

Symmetry code: (i) .