(E)-3-[(2-Methyl-4-nitro-phen-yl)imino-meth-yl]-1-benzothio-phene.

In the title conpound, C(16)H(12)N(2)O(2)S, the 1-benzothio-phene residue and the substituted benzene ring are oriented at a dihedral angle of 53.36 (6)°. The mol-ecular conformation features a short C-H⋯N contact. There are no significant inter-molecular contacts.

Related literature

For the biological activity of Schiff bases, see: Barton et al. (1979 ▶); Ingold (1969 ▶); Layer (1963 ▶). For industrial applications of n class="Chemical">Schiff bases, see: Taggi et al. (2002 ▶). For chemical properties of Schiff bases, see: Aydoğan et al. (2001 ▶). For related structures, see: Ağar et al. (2010 ▶); Ceylan et al. (2011 ▶); Dege et al. (2006 ▶); Demirtaş et al. (2009 ▶); Tecer et al. (2010 ▶).

Experimental

Crystal data

C16H12N2O2S

M = 296.34

Monoclinic,

a = 7.6224 (4) Å

b = 7.9139 (4) Å

c = 11.7536 (5) Å

β = 91.341 (4)°

V = 708.82 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.17 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction SuperNova Single source at offset diffractometer with an Eos detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.563, T max = 1.000

2851 measured reflections

2108 independent reflections

1870 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.089

S = 1.05

2108 reflections

191 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 572 Friedel pairs

Flack parameter: −0.07 (11)

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: WinGX (Farrugia, 1997 ▶) and SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: OLEX2, WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000190/bt5774sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000190/bt5774Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000190/bt5774Isup3.cml

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

C16H12N2O2S	F(000) = 308
Mr = 296.34	Dx = 1.388 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2yb	Cell parameters from 1356 reflections
a = 7.6224 (4) Å	θ = 3.2–27.7°
b = 7.9139 (4) Å	µ = 0.23 mm−1
c = 11.7536 (5) Å	T = 296 K
β = 91.341 (4)°	Prism, brown
V = 708.82 (6) Å3	0.17 × 0.15 × 0.12 mm
Z = 2

Oxford Diffraction SuperNova Single source at offset diffractometer with an Eos detector	2108 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1870 reflections with I > 2σ(I)
mirror	Rint = 0.013
Detector resolution: 16.0454 pixels mm-1	θmax = 27.8°, θmin = 3.2°
ω scans	h = −4→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→5
Tmin = 0.563, Tmax = 1.000	l = −15→14
2851 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0369P)2 + 0.1426P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2108 reflections	Δρmax = 0.15 e Å−3
191 parameters	Δρmin = −0.14 e Å−3
1 restraint	Absolute structure: Flack (1983), 572 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.07 (11)

Experimental. CrysAlis PRO (Oxford Diffraction, 2009)

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	0.7745 (4)	0.7800 (4)	0.3597 (2)	0.0487 (7)
C2	0.9349 (4)	0.8478 (4)	0.3262 (3)	0.0621 (8)
H2	0.9650	0.8497	0.2500	0.075*
C3	1.0455 (4)	0.9109 (5)	0.4081 (3)	0.0662 (9)
H3	1.1529	0.9561	0.3876	0.079*
C4	0.9999 (4)	0.9087 (5)	0.5225 (3)	0.0591 (8)
H4	1.0768	0.9545	0.5768	0.071*
C5	0.8438 (4)	0.8401 (4)	0.5565 (2)	0.0491 (7)
H5	0.8165	0.8377	0.6332	0.059*
C6	0.7263 (4)	0.7740 (3)	0.4744 (2)	0.0444 (6)
C7	0.5540 (3)	0.6999 (5)	0.4864 (2)	0.0488 (6)
C8	0.4620 (3)	0.6719 (4)	0.5914 (2)	0.0512 (7)
H8	0.3469	0.6330	0.5868	0.061*
C9	0.4821 (4)	0.6556 (4)	0.3838 (2)	0.0585 (8)
H9	0.3708	0.6083	0.3759	0.070*
C10	0.4313 (3)	0.6683 (4)	0.7870 (2)	0.0497 (7)
C11	0.2601 (4)	0.7284 (4)	0.7959 (2)	0.0597 (8)
H11	0.2086	0.7888	0.7360	0.072*
C12	0.1660 (4)	0.6983 (5)	0.8939 (2)	0.0639 (8)
H12	0.0516	0.7373	0.9004	0.077*
C13	0.2467 (4)	0.6093 (4)	0.9806 (2)	0.0603 (9)
C14	0.4166 (4)	0.5529 (5)	0.9747 (2)	0.0614 (8)
H14	0.4677	0.4944	1.0355	0.074*
C15	0.5110 (4)	0.5831 (4)	0.8783 (2)	0.0539 (8)
C16	0.6974 (4)	0.5212 (6)	0.8702 (3)	0.0789 (11)
H16A	0.7464	0.5045	0.9453	0.118*
H16B	0.7657	0.6034	0.8307	0.118*
H16C	0.6986	0.4162	0.8293	0.118*
N1	0.5308 (3)	0.6980 (4)	0.68930 (16)	0.0527 (6)
N2	0.1479 (5)	0.5769 (5)	1.0843 (3)	0.0851 (10)
O1	0.2209 (5)	0.5011 (5)	1.1621 (2)	0.1246 (13)
O2	−0.0032 (4)	0.6264 (5)	1.0876 (2)	0.1153 (14)
S1	0.61283 (11)	0.69395 (13)	0.27057 (6)	0.0641 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0627 (17)	0.0399 (16)	0.0435 (14)	0.0049 (13)	0.0028 (12)	0.0020 (13)
C2	0.077 (2)	0.055 (2)	0.0559 (18)	−0.0021 (18)	0.0215 (15)	−0.0005 (16)
C3	0.0635 (19)	0.060 (2)	0.075 (2)	−0.0075 (17)	0.0136 (17)	0.0057 (18)
C4	0.0594 (17)	0.057 (2)	0.061 (2)	−0.0096 (16)	−0.0056 (15)	0.0006 (16)
C5	0.0591 (17)	0.0436 (16)	0.0445 (15)	−0.0019 (14)	−0.0013 (12)	0.0024 (14)
C6	0.0537 (15)	0.0366 (15)	0.0431 (14)	0.0046 (12)	0.0027 (11)	0.0028 (12)
C7	0.0583 (15)	0.0451 (16)	0.0430 (12)	−0.0049 (15)	−0.0015 (10)	0.0052 (16)
C8	0.0521 (14)	0.0483 (18)	0.0533 (15)	−0.0074 (15)	0.0006 (11)	0.0051 (16)
C9	0.0659 (18)	0.059 (2)	0.0505 (15)	−0.0105 (16)	−0.0039 (13)	0.0039 (15)
C10	0.0571 (15)	0.0471 (18)	0.0447 (13)	−0.0116 (15)	−0.0014 (11)	−0.0015 (14)
C11	0.0644 (18)	0.062 (2)	0.0524 (15)	−0.0003 (16)	−0.0018 (13)	0.0056 (16)
C12	0.0562 (16)	0.071 (2)	0.0654 (17)	−0.002 (2)	0.0102 (13)	−0.013 (2)
C13	0.074 (2)	0.067 (2)	0.0397 (15)	−0.0203 (16)	0.0091 (14)	−0.0096 (15)
C14	0.077 (2)	0.063 (2)	0.0440 (16)	−0.0119 (17)	−0.0038 (15)	−0.0017 (15)
C15	0.0631 (18)	0.058 (2)	0.0409 (15)	−0.0080 (14)	−0.0032 (13)	0.0020 (14)
C16	0.069 (2)	0.101 (3)	0.067 (2)	0.011 (2)	−0.0075 (17)	0.014 (2)
N1	0.0554 (12)	0.0593 (15)	0.0433 (11)	−0.0099 (15)	0.0006 (9)	0.0055 (15)
N2	0.100 (2)	0.103 (3)	0.0538 (18)	−0.034 (2)	0.0222 (17)	−0.0200 (18)
O1	0.149 (3)	0.169 (4)	0.0565 (16)	−0.017 (3)	0.0217 (17)	0.029 (2)
O2	0.096 (2)	0.175 (4)	0.0766 (17)	−0.027 (2)	0.0362 (15)	−0.0328 (19)
S1	0.0847 (5)	0.0675 (5)	0.0399 (3)	−0.0104 (5)	−0.0024 (3)	−0.0013 (4)

C1—C2	1.401 (4)	C10—C11	1.395 (4)
C1—C6	1.406 (3)	C10—C15	1.395 (4)
C1—S1	1.738 (3)	C10—N1	1.411 (3)
C2—C3	1.359 (5)	C11—C12	1.391 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.397 (5)	C12—C13	1.373 (5)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.376 (4)	C13—C14	1.373 (5)
C4—H4	0.9300	C13—N2	1.470 (4)
C5—C6	1.403 (4)	C14—C15	1.377 (4)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.448 (4)	C15—C16	1.508 (4)
C7—C9	1.359 (3)	C16—H16A	0.9600
C7—C8	1.450 (3)	C16—H16B	0.9600
C8—N1	1.271 (3)	C16—H16C	0.9600
C8—H8	0.9300	N2—O1	1.218 (4)
C9—S1	1.709 (3)	N2—O2	1.218 (4)
C9—H9	0.9300
C2—C1—C6	122.1 (3)	C11—C10—N1	121.7 (3)
C2—C1—S1	126.3 (2)	C15—C10—N1	118.3 (3)
C6—C1—S1	111.6 (2)	C12—C11—C10	120.3 (3)
C3—C2—C1	118.3 (3)	C12—C11—H11	119.8
C3—C2—H2	120.9	C10—C11—H11	119.8
C1—C2—H2	120.9	C13—C12—C11	118.2 (3)
C2—C3—C4	120.8 (3)	C13—C12—H12	120.9
C2—C3—H3	119.6	C11—C12—H12	120.9
C4—C3—H3	119.6	C12—C13—C14	122.4 (3)
C5—C4—C3	121.4 (3)	C12—C13—N2	118.4 (3)
C5—C4—H4	119.3	C14—C13—N2	119.2 (3)
C3—C4—H4	119.3	C13—C14—C15	119.8 (3)
C4—C5—C6	119.3 (3)	C13—C14—H14	120.1
C4—C5—H5	120.3	C15—C14—H14	120.1
C6—C5—H5	120.3	C14—C15—C10	119.3 (3)
C5—C6—C1	118.1 (3)	C14—C15—C16	120.5 (3)
C5—C6—C7	130.5 (2)	C10—C15—C16	120.1 (3)
C1—C6—C7	111.4 (2)	C15—C16—H16A	109.5
C9—C7—C6	111.4 (2)	C15—C16—H16B	109.5
C9—C7—C8	121.5 (3)	H16A—C16—H16B	109.5
C6—C7—C8	127.0 (2)	C15—C16—H16C	109.5
N1—C8—C7	123.2 (2)	H16A—C16—H16C	109.5
N1—C8—H8	118.4	H16B—C16—H16C	109.5
C7—C8—H8	118.4	C8—N1—C10	119.4 (2)
C7—C9—S1	114.5 (2)	O1—N2—O2	123.4 (3)
C7—C9—H9	122.7	O1—N2—C13	118.3 (4)
S1—C9—H9	122.7	O2—N2—C13	118.3 (4)
C11—C10—C15	119.9 (2)	C9—S1—C1	91.03 (13)
C6—C1—C2—C3	−0.6 (5)	C10—C11—C12—C13	0.3 (5)
S1—C1—C2—C3	179.6 (3)	C11—C12—C13—C14	1.4 (5)
C1—C2—C3—C4	−0.3 (5)	C11—C12—C13—N2	−179.9 (3)
C2—C3—C4—C5	1.2 (5)	C12—C13—C14—C15	−1.0 (5)
C3—C4—C5—C6	−1.3 (5)	N2—C13—C14—C15	−179.7 (3)
C4—C5—C6—C1	0.3 (4)	C13—C14—C15—C10	−1.2 (5)
C4—C5—C6—C7	−178.2 (3)	C13—C14—C15—C16	−179.7 (3)
C2—C1—C6—C5	0.6 (4)	C11—C10—C15—C14	2.8 (5)
S1—C1—C6—C5	−179.6 (2)	N1—C10—C15—C14	179.9 (3)
C2—C1—C6—C7	179.4 (3)	C11—C10—C15—C16	−178.7 (3)
S1—C1—C6—C7	−0.8 (3)	N1—C10—C15—C16	−1.6 (5)
C5—C6—C7—C9	178.3 (3)	C7—C8—N1—C10	179.7 (3)
C1—C6—C7—C9	−0.3 (4)	C11—C10—N1—C8	−47.3 (5)
C5—C6—C7—C8	−1.9 (5)	C15—C10—N1—C8	135.7 (3)
C1—C6—C7—C8	179.5 (3)	C12—C13—N2—O1	−178.5 (3)
C9—C7—C8—N1	173.7 (3)	C14—C13—N2—O1	0.3 (5)
C6—C7—C8—N1	−6.1 (6)	C12—C13—N2—O2	1.9 (5)
C6—C7—C9—S1	1.3 (4)	C14—C13—N2—O2	−179.3 (3)
C8—C7—C9—S1	−178.5 (3)	C7—C9—S1—C1	−1.5 (3)
C15—C10—C11—C12	−2.4 (5)	C2—C1—S1—C9	−178.9 (3)
N1—C10—C11—C12	−179.4 (3)	C6—C1—S1—C9	1.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1	0.93	2.54	3.093 (4)	118.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N1	0.93	2.54	3.093 (4)	118