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

In the title mol-ecule, C(11)H(9)N(3)O(2)S, the thio-phene and benzene rings form a dihedral angle of 17.68 (9)°. The thio-phene S atom and the imine N atom are syn with respect to each other. In the crystal, N-H⋯O and N-H⋯N hydrogen bonds connect mol-ecules, forming a two-dimensional network parallel to (10-1).

Related literature

For similar structures, see: Asiri et al. (2012a ▶,b ▶); Prasath et al. (2010 ▶). For a discussion of the use of Schiff base compounds containing thio­phene in fluorescent chemosensors, see: Chen et al. (2012 ▶). For a review of the biological use of 2-thio­phenes, see Kleemann et al. (2006 ▶). For a crystal structure from a related study on thio­phene-substituted benzimidazoles, see: Geiger et al. (2012 ▶).

Experimental

Crystal data

C11H9N3O2S

M = 247.27

Monoclinic,

a = 24.335 (4) Å

b = 7.2084 (10) Å

c = 16.932 (3) Å

β = 133.396 (10)°

V = 2158.3 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 200 K

0.60 × 0.30 × 0.20 mm

Data collection

Bruker SMART X2S benchtop diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.844, T max = 0.944

6460 measured reflections

1923 independent reflections

1619 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.138

S = 1.09

1923 reflections

166 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.45 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XSHELL (Bruker, 2004 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037464/lh5523sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812037464/lh5523Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037464/lh5523Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812037464/lh5523Isup4.cml

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

C11H9N3O2S	F(000) = 1024
Mr = 247.27	Dx = 1.522 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2950 reflections
a = 24.335 (4) Å	θ = 2.3–25.0°
b = 7.2084 (10) Å	µ = 0.29 mm−1
c = 16.932 (3) Å	T = 200 K
β = 133.396 (10)°	Plate, orange
V = 2158.3 (6) Å3	0.60 × 0.30 × 0.20 mm
Z = 8

Bruker SMART X2S benchtop diffractometer	1923 independent reflections
Radiation source: XOS X-beam microfocus source	1619 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.072
ω scans	θmax = 25.1°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→28
Tmin = 0.844, Tmax = 0.944	k = −8→8
6460 measured reflections	l = −20→20

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0862P)2 + 0.1606P] where P = (Fo2 + 2Fc2)/3
1923 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.46 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
S1	0.37474 (3)	−0.02144 (9)	0.15352 (4)	0.0390 (3)
O1	−0.11073 (9)	0.1684 (3)	−0.18166 (15)	0.0536 (5)
O2	−0.06193 (9)	0.0037 (3)	−0.22717 (13)	0.0485 (5)
N1	0.23171 (10)	0.3033 (3)	0.22589 (14)	0.0317 (4)
HA	0.2348 (12)	0.384 (3)	0.268 (2)	0.033 (6)*
HB	0.2669 (13)	0.292 (3)	0.230 (2)	0.040 (7)*
N2	0.22136 (9)	0.0875 (2)	0.08347 (13)	0.0246 (4)
N3	−0.05550 (10)	0.1071 (3)	−0.16331 (15)	0.0356 (5)
C1	0.16213 (10)	0.2554 (3)	0.13152 (15)	0.0227 (4)
C2	0.15340 (11)	0.1461 (3)	0.05347 (15)	0.0225 (4)
C3	0.08196 (11)	0.0985 (3)	−0.04247 (15)	0.0250 (5)
H3	0.0758	0.0245	−0.0945	0.030*
C4	0.01887 (11)	0.1588 (3)	−0.06301 (16)	0.0268 (5)
C5	0.02641 (12)	0.2658 (3)	0.01241 (18)	0.0318 (5)
H5	−0.0171	0.3059	−0.0024	0.038*
C6	0.09727 (12)	0.3126 (3)	0.10818 (17)	0.0305 (5)
H6	0.1025	0.3853	0.1598	0.037*
C7	0.21931 (11)	0.0503 (3)	0.00748 (16)	0.0243 (4)
H7	0.1755 (11)	0.058 (3)	−0.0645 (17)	0.020 (5)*
C8	0.28411 (11)	−0.0148 (3)	0.02707 (16)	0.0242 (5)
C9	0.28193 (11)	−0.0775 (3)	−0.05083 (16)	0.0285 (5)
H9	0.2371	−0.0815	−0.1260	0.034*
C10	0.35331 (12)	−0.1360 (3)	−0.00832 (17)	0.0304 (5)
H10	0.3616	−0.1855	−0.0514	0.037*
C11	0.40851 (13)	−0.1137 (3)	0.10053 (18)	0.0377 (6)
H11	0.4600	−0.1455	0.1427	0.045*

	U11	U22	U33	U12	U13	U23
S1	0.0295 (4)	0.0638 (5)	0.0252 (4)	0.0090 (2)	0.0193 (3)	0.0003 (2)
O1	0.0246 (9)	0.0738 (13)	0.0535 (11)	0.0082 (8)	0.0235 (8)	0.0051 (9)
O2	0.0351 (10)	0.0698 (12)	0.0314 (9)	−0.0101 (8)	0.0193 (8)	−0.0121 (8)
N1	0.0313 (10)	0.0408 (11)	0.0265 (9)	−0.0039 (8)	0.0213 (9)	−0.0060 (8)
N2	0.0262 (9)	0.0252 (9)	0.0284 (8)	0.0010 (7)	0.0210 (8)	−0.0007 (7)
N3	0.0254 (10)	0.0443 (11)	0.0340 (10)	0.0012 (8)	0.0192 (8)	0.0081 (8)
C1	0.0269 (10)	0.0232 (9)	0.0238 (9)	0.0013 (8)	0.0196 (8)	0.0035 (8)
C2	0.0262 (10)	0.0225 (10)	0.0253 (10)	0.0023 (8)	0.0202 (9)	0.0041 (8)
C3	0.0280 (11)	0.0266 (11)	0.0255 (9)	−0.0004 (8)	0.0204 (9)	−0.0007 (8)
C4	0.0230 (10)	0.0311 (11)	0.0282 (10)	0.0000 (8)	0.0183 (9)	0.0031 (8)
C5	0.0315 (11)	0.0356 (11)	0.0413 (11)	0.0036 (9)	0.0301 (10)	0.0046 (10)
C6	0.0380 (12)	0.0325 (11)	0.0344 (11)	0.0023 (9)	0.0300 (10)	−0.0015 (9)
C7	0.0277 (11)	0.0238 (10)	0.0256 (10)	0.0012 (8)	0.0199 (9)	0.0037 (8)
C8	0.0269 (11)	0.0242 (10)	0.0288 (10)	0.0023 (8)	0.0220 (10)	0.0043 (8)
C9	0.0335 (11)	0.0312 (11)	0.0286 (10)	−0.0019 (9)	0.0243 (10)	0.0016 (9)
C10	0.0371 (12)	0.0322 (11)	0.0377 (11)	0.0039 (9)	0.0317 (11)	0.0020 (9)
C11	0.0304 (12)	0.0523 (14)	0.0373 (11)	0.0091 (10)	0.0259 (10)	0.0046 (10)

S1—C11	1.713 (2)	C3—H3	0.9500
S1—C8	1.721 (2)	C4—C5	1.392 (3)
O1—N3	1.235 (2)	C5—C6	1.369 (3)
O2—N3	1.232 (2)	C5—H5	0.9500
N1—C1	1.350 (3)	C6—H6	0.9500
N1—HA	0.88 (2)	C7—C8	1.449 (3)
N1—HB	0.81 (2)	C7—H7	0.92 (2)
N2—C7	1.281 (3)	C8—C9	1.360 (3)
N2—C2	1.420 (2)	C9—C10	1.413 (3)
N3—C4	1.440 (3)	C9—H9	0.9500
C1—C6	1.400 (3)	C10—C11	1.351 (3)
C1—C2	1.424 (3)	C10—H10	0.9500
C2—C3	1.378 (3)	C11—H11	0.9500
C3—C4	1.391 (2)
C11—S1—C8	91.44 (10)	C6—C5—H5	120.4
C1—N1—HA	117.8 (14)	C4—C5—H5	120.4
C1—N1—HB	118.2 (18)	C5—C6—C1	121.34 (18)
HA—N1—HB	119 (2)	C5—C6—H6	119.3
C7—N2—C2	118.08 (16)	C1—C6—H6	119.3
O2—N3—O1	122.40 (19)	N2—C7—C8	123.55 (18)
O2—N3—C4	119.38 (17)	N2—C7—H7	122.0 (12)
O1—N3—C4	118.23 (19)	C8—C7—H7	114.4 (12)
N1—C1—C6	120.86 (18)	C9—C8—C7	125.06 (19)
N1—C1—C2	120.42 (17)	C9—C8—S1	111.09 (15)
C6—C1—C2	118.72 (17)	C7—C8—S1	123.84 (15)
C3—C2—N2	124.30 (16)	C8—C9—C10	112.96 (18)
C3—C2—C1	119.68 (17)	C8—C9—H9	123.5
N2—C2—C1	115.98 (17)	C10—C9—H9	123.5
C2—C3—C4	119.93 (17)	C11—C10—C9	112.44 (18)
C2—C3—H3	120.0	C11—C10—H10	123.8
C4—C3—H3	120.0	C9—C10—H10	123.8
C3—C4—C5	121.12 (18)	C10—C11—S1	112.05 (16)
C3—C4—N3	119.41 (17)	C10—C11—H11	124.0
C5—C4—N3	119.47 (17)	S1—C11—H11	124.0
C6—C5—C4	119.21 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—HB···O1i	0.81 (2)	2.25 (2)	2.991 (2)	152 (2)
N1—HA···N2ii	0.88 (2)	2.43 (3)	3.295 (2)	164.9 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HB⋯O1i	0.81 (2)	2.25 (2)	2.991 (2)	152 (2)
N1—HA⋯N2ii	0.88 (2)	2.43 (3)	3.295 (2)	164.9 (19)

Symmetry codes: (i) ; (ii) .