4-Nitro-N-[(E)-thio-phen-2-yl-methyl-idene]aniline.

In the title compound, C(11)H(8)N(2)O(2)S, there is a twist in the mol-ecule, with the dihedral angle between the five- and six-membered rings being 31.77 (9)°. The nitro group is slightly twisted out of the plane of the benzene ring to which it is attached [O-N-C-C torsion angle = 9.0 (3)°]. The S and N atoms are syn. In the crystal, supra-molecular layers parallel to (-204) are formed by C-H⋯O and C-H⋯N inter-actions. These layers are connected into a three-dimensional architecture by π-π inter-actions occurring between centrosymmetrically related benzene rings [centroid-centroid distance = 3.6020 (11) Å].

Related literature

For background to 2-substituted thio­phenes, see: Kleemann et al. (2006 ▶). For a related structure, see: Asiri et al. (2012 ▶).

Experimental

Crystal data

C11H8N2O2S

M = 232.25

Monoclinic,

a = 9.2754 (5) Å

b = 11.9983 (9) Å

c = 18.4996 (13) Å

β = 92.772 (6)°

V = 2056.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.30 mm−1

T = 100 K

0.25 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.692, T max = 1.000

8697 measured reflections

2377 independent reflections

1869 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.111

S = 1.04

2377 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028346/bt5953sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028346/bt5953Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028346/bt5953Isup3.cml

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

C11H8N2O2S	F(000) = 960
Mr = 232.25	Dx = 1.500 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2057 reflections
a = 9.2754 (5) Å	θ = 2.8–27.5°
b = 11.9983 (9) Å	µ = 0.30 mm−1
c = 18.4996 (13) Å	T = 100 K
β = 92.772 (6)°	Prism, yellow
V = 2056.4 (2) Å3	0.25 × 0.15 × 0.05 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	2377 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1869 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.050
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.8°
ω scan	h = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→15
Tmin = 0.692, Tmax = 1.000	l = −22→24
8697 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.049P)2 + 1.4742P] where P = (Fo2 + 2Fc2)/3
2377 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.31 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	0.22121 (5)	0.35279 (4)	0.24739 (3)	0.01985 (16)
O1	0.94206 (15)	0.49221 (12)	0.60866 (8)	0.0287 (4)
O2	0.92261 (17)	0.65565 (13)	0.55892 (8)	0.0330 (4)
N1	0.45609 (16)	0.40163 (13)	0.36388 (8)	0.0172 (3)
N2	0.88841 (17)	0.55649 (14)	0.56311 (9)	0.0213 (4)
C1	0.1448 (2)	0.24635 (16)	0.19692 (10)	0.0216 (4)
H1	0.0693	0.2567	0.1610	0.026*
C2	0.2041 (2)	0.14558 (16)	0.21402 (10)	0.0191 (4)
H2	0.1742	0.0776	0.1916	0.023*
C3	0.3151 (2)	0.15307 (15)	0.26874 (10)	0.0178 (4)
H3	0.3687	0.0909	0.2871	0.021*
C4	0.33686 (19)	0.26104 (15)	0.29257 (10)	0.0165 (4)
C5	0.44640 (19)	0.29889 (16)	0.34505 (10)	0.0168 (4)
H5	0.5128	0.2465	0.3661	0.020*
C6	0.56731 (19)	0.43424 (15)	0.41452 (10)	0.0156 (4)
C7	0.6258 (2)	0.54040 (16)	0.40547 (10)	0.0186 (4)
H7	0.5925	0.5852	0.3658	0.022*
C8	0.7316 (2)	0.58087 (16)	0.45373 (10)	0.0195 (4)
H8	0.7716	0.6530	0.4477	0.023*
C9	0.77767 (19)	0.51350 (16)	0.51104 (9)	0.0172 (4)
C10	0.7220 (2)	0.40827 (16)	0.52155 (10)	0.0186 (4)
H10	0.7565	0.3637	0.5612	0.022*
C11	0.6151 (2)	0.36890 (16)	0.47345 (10)	0.0190 (4)
H11	0.5742	0.2974	0.4805	0.023*

	U11	U22	U33	U12	U13	U23
S1	0.0209 (3)	0.0158 (3)	0.0223 (3)	0.00164 (19)	−0.00515 (19)	−0.00144 (18)
O1	0.0258 (8)	0.0328 (9)	0.0264 (8)	0.0027 (7)	−0.0107 (6)	0.0029 (6)
O2	0.0361 (9)	0.0281 (9)	0.0334 (9)	−0.0135 (7)	−0.0118 (7)	0.0019 (7)
N1	0.0164 (8)	0.0180 (8)	0.0169 (8)	−0.0001 (6)	−0.0022 (6)	−0.0005 (6)
N2	0.0182 (8)	0.0258 (10)	0.0196 (9)	−0.0014 (7)	−0.0017 (7)	−0.0019 (7)
C1	0.0191 (10)	0.0246 (11)	0.0203 (10)	−0.0014 (8)	−0.0060 (8)	−0.0028 (8)
C2	0.0213 (10)	0.0182 (10)	0.0175 (10)	−0.0024 (8)	−0.0015 (8)	−0.0021 (7)
C3	0.0190 (9)	0.0158 (10)	0.0183 (9)	0.0004 (7)	−0.0019 (7)	0.0011 (7)
C4	0.0160 (9)	0.0173 (9)	0.0160 (9)	0.0010 (7)	−0.0002 (7)	0.0003 (7)
C5	0.0161 (9)	0.0183 (10)	0.0161 (9)	0.0014 (8)	−0.0002 (7)	0.0023 (7)
C6	0.0133 (8)	0.0174 (9)	0.0160 (9)	0.0012 (7)	−0.0003 (7)	−0.0033 (7)
C7	0.0176 (9)	0.0203 (10)	0.0176 (9)	0.0011 (8)	−0.0008 (7)	0.0040 (7)
C8	0.0189 (9)	0.0181 (10)	0.0214 (10)	−0.0040 (8)	−0.0003 (8)	0.0006 (7)
C9	0.0124 (9)	0.0243 (10)	0.0148 (9)	−0.0006 (7)	−0.0009 (7)	−0.0035 (7)
C10	0.0202 (9)	0.0190 (10)	0.0165 (9)	0.0016 (8)	−0.0014 (7)	0.0008 (7)
C11	0.0220 (10)	0.0165 (9)	0.0184 (10)	−0.0003 (8)	−0.0001 (8)	−0.0005 (7)

S1—C1	1.7150 (19)	C4—C5	1.444 (2)
S1—C4	1.7246 (18)	C5—H5	0.9500
O1—N2	1.230 (2)	C6—C11	1.398 (3)
O2—N2	1.235 (2)	C6—C7	1.397 (3)
N1—C5	1.283 (2)	C7—C8	1.382 (3)
N1—C6	1.415 (2)	C7—H7	0.9500
N2—C9	1.467 (2)	C8—C9	1.384 (3)
C1—C2	1.359 (3)	C8—H8	0.9500
C1—H1	0.9500	C9—C10	1.382 (3)
C2—C3	1.411 (3)	C10—C11	1.383 (3)
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.380 (3)	C11—H11	0.9500
C3—H3	0.9500
C1—S1—C4	91.13 (9)	C4—C5—H5	119.3
C5—N1—C6	119.00 (16)	C11—C6—C7	119.63 (17)
O1—N2—O2	123.41 (16)	C11—C6—N1	123.71 (17)
O1—N2—C9	118.47 (16)	C7—C6—N1	116.58 (16)
O2—N2—C9	118.12 (16)	C8—C7—C6	120.68 (17)
C2—C1—S1	112.55 (15)	C8—C7—H7	119.7
C2—C1—H1	123.7	C6—C7—H7	119.7
S1—C1—H1	123.7	C7—C8—C9	118.21 (17)
C1—C2—C3	112.54 (17)	C7—C8—H8	120.9
C1—C2—H2	123.7	C9—C8—H8	120.9
C3—C2—H2	123.7	C10—C9—C8	122.53 (17)
C4—C3—C2	112.28 (17)	C10—C9—N2	118.91 (16)
C4—C3—H3	123.9	C8—C9—N2	118.56 (17)
C2—C3—H3	123.9	C9—C10—C11	118.88 (18)
C3—C4—C5	126.67 (18)	C9—C10—H10	120.6
C3—C4—S1	111.50 (14)	C11—C10—H10	120.6
C5—C4—S1	121.73 (14)	C10—C11—C6	120.05 (18)
N1—C5—C4	121.49 (17)	C10—C11—H11	120.0
N1—C5—H5	119.3	C6—C11—H11	120.0
C4—S1—C1—C2	0.33 (16)	N1—C6—C7—C8	177.85 (16)
S1—C1—C2—C3	−0.5 (2)	C6—C7—C8—C9	0.0 (3)
C1—C2—C3—C4	0.5 (2)	C7—C8—C9—C10	−0.1 (3)
C2—C3—C4—C5	−176.49 (17)	C7—C8—C9—N2	−179.10 (16)
C2—C3—C4—S1	−0.2 (2)	O1—N2—C9—C10	9.7 (3)
C1—S1—C4—C3	−0.06 (15)	O2—N2—C9—C10	−170.11 (18)
C1—S1—C4—C5	176.43 (16)	O1—N2—C9—C8	−171.17 (17)
C6—N1—C5—C4	−178.81 (16)	O2—N2—C9—C8	9.0 (3)
C3—C4—C5—N1	−179.32 (19)	C8—C9—C10—C11	−0.6 (3)
S1—C4—C5—N1	4.7 (3)	N2—C9—C10—C11	178.44 (16)
C5—N1—C6—C11	−37.0 (3)	C9—C10—C11—C6	1.3 (3)
C5—N1—C6—C7	146.04 (18)	C7—C6—C11—C10	−1.4 (3)
C11—C6—C7—C8	0.8 (3)	N1—C6—C11—C10	−178.30 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2i	0.95	2.50	3.412 (2)	160
C2—H2···N1ii	0.95	2.62	3.556 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2i	0.95	2.50	3.412 (2)	160
C2—H2⋯N1ii	0.95	2.62	3.556 (2)	169

Symmetry codes: (i) ; (ii) .