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

The title mol-ecule, C(12)H(10)N(2)O(3)S, is nonplanar with an inter-planar angle of 33.44 (7)° between the benzene and thio-phene rings. In the crystal there exist only weak inter-molecular C-H⋯O inter-actions, π-π inter-actions between the benzene rings [centroid-centroid distance = 3.7465 (14) Å] and X-Y⋯π inter-actions to the thio-phene and benzene rings [N⋯centroid distances = 3.718 (3) and 3.355 (3) Å, respectively]. Inter-molecular C-H⋯O inter-actions link the mol-ecules into chains parallel to the a axis.

Related literature

For the biological properties of Schiff bases, see Layer (1963 ▶); Ingold (1969 ▶); Barton & Ollis (1979 ▶). For the application of Schiff bases in industry, see Taggi et al. (2002 ▶). For related structures, see Ceylan et al. (2011 ▶); Özdemir & Işık (2012 ▶).

Experimental

Crystal data

C12H10N2O3S

M = 262.28

Monoclinic,

a = 12.5641 (7) Å

b = 13.1441 (5) Å

c = 7.7896 (4) Å

β = 106.012 (4)°

V = 1236.50 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.69 × 0.51 × 0.28 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.873, T max = 0.938

20097 measured reflections

2841 independent reflections

2076 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.125

S = 1.15

2841 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.22 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: WinGX (Farrugia, 1997 ▶) and 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 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812034344/fb2260sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812034344/fb2260Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034344/fb2260Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812034344/fb2260Isup4.cml

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

C12H10N2O3S	F(000) = 544
Mr = 262.28	Dx = 1.409 Mg m−3
Monoclinic, P21/c	Melting point = 414–417 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.5641 (7) Å	Cell parameters from 20097 reflections
b = 13.1441 (5) Å	θ = 2.3–27.6°
c = 7.7896 (4) Å	µ = 0.26 mm−1
β = 106.012 (4)°	T = 296 K
V = 1236.50 (10) Å3	Prism, yellow
Z = 4	0.69 × 0.51 × 0.28 mm

Stoe IPDS 2 diffractometer	2841 independent reflections
Radiation source: fine-focus sealed tube	2076 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
w–scan rotation	θmax = 27.6°, θmin = 2.3°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −16→16
Tmin = 0.873, Tmax = 0.938	k = −17→17
20097 measured reflections	l = −10→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0447P)2 + 0.3031P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
2841 reflections	Δρmax = 0.29 e Å−3
164 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
39 constraints	Extinction coefficient: 0
Primary atom site location: structure-invariant direct methods

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	0.77562 (5)	0.12622 (5)	0.06150 (7)	0.05989 (19)
C1	0.51607 (18)	0.11596 (17)	0.3360 (3)	0.0561 (5)
N2	0.60693 (16)	0.11489 (15)	0.2619 (3)	0.0597 (5)
C11	0.70493 (19)	0.11725 (18)	0.3637 (3)	0.0586 (5)
H11	0.7168	0.1176	0.4870	0.070*
C9	0.97699 (19)	0.1197 (2)	0.2631 (3)	0.0658 (6)
H9	1.0540	0.1186	0.3003	0.079*
O3	0.23334 (13)	0.11016 (14)	0.5127 (2)	0.0722 (5)
N1	0.95778 (19)	0.12583 (16)	−0.0612 (3)	0.0693 (5)
C10	0.91555 (18)	0.12453 (18)	0.0913 (3)	0.0576 (5)
C4	0.32882 (18)	0.11543 (17)	0.4617 (3)	0.0572 (5)
O1	1.05738 (18)	0.12534 (19)	−0.0377 (3)	0.0968 (7)
O2	0.88984 (18)	0.12695 (18)	−0.2095 (2)	0.0922 (6)
C7	0.79851 (18)	0.11941 (18)	0.2889 (3)	0.0554 (5)
C8	0.90855 (19)	0.1166 (2)	0.3776 (3)	0.0657 (6)
H8	0.9353	0.1131	0.5013	0.079*
C2	0.5164 (2)	0.1630 (2)	0.4951 (3)	0.0660 (6)
H2	0.5804	0.1956	0.5607	0.079*
C3	0.4248 (2)	0.1628 (2)	0.5585 (3)	0.0661 (6)
H3	0.4273	0.1944	0.6663	0.079*
C5	0.32604 (19)	0.0703 (2)	0.3006 (3)	0.0643 (6)
H5	0.2614	0.0390	0.2339	0.077*
C6	0.41788 (18)	0.0713 (2)	0.2382 (3)	0.0616 (6)
H6	0.4144	0.0416	0.1285	0.074*
C12	0.2326 (3)	0.1537 (3)	0.6792 (4)	0.0895 (9)
H12A	0.1627	0.1402	0.7023	0.134*
H12B	0.2435	0.2259	0.6754	0.134*
H12C	0.2911	0.1245	0.7725	0.134*

	U11	U22	U33	U12	U13	U23
S1	0.0572 (3)	0.0756 (4)	0.0446 (3)	−0.0047 (3)	0.0102 (2)	−0.0023 (3)
C1	0.0560 (12)	0.0581 (13)	0.0533 (12)	−0.0017 (10)	0.0132 (10)	0.0017 (10)
N2	0.0581 (11)	0.0657 (12)	0.0558 (11)	−0.0027 (9)	0.0163 (9)	0.0021 (9)
C11	0.0615 (13)	0.0663 (14)	0.0499 (12)	−0.0029 (11)	0.0184 (10)	0.0034 (11)
C9	0.0530 (12)	0.0927 (18)	0.0504 (13)	−0.0001 (12)	0.0120 (10)	−0.0022 (12)
O3	0.0560 (9)	0.0878 (12)	0.0758 (11)	−0.0055 (8)	0.0235 (8)	−0.0134 (9)
N1	0.0777 (14)	0.0796 (14)	0.0574 (13)	−0.0052 (12)	0.0302 (11)	−0.0056 (11)
C10	0.0595 (12)	0.0671 (13)	0.0487 (12)	−0.0024 (11)	0.0193 (10)	−0.0034 (11)
C4	0.0505 (11)	0.0578 (13)	0.0617 (14)	0.0034 (10)	0.0129 (10)	−0.0004 (11)
O1	0.0818 (13)	0.1392 (19)	0.0829 (14)	−0.0052 (13)	0.0452 (11)	−0.0052 (13)
O2	0.1034 (14)	0.1289 (18)	0.0462 (10)	−0.0080 (13)	0.0236 (10)	−0.0058 (11)
C7	0.0579 (12)	0.0619 (13)	0.0471 (12)	−0.0052 (10)	0.0158 (9)	0.0001 (10)
C8	0.0590 (13)	0.0936 (18)	0.0433 (12)	−0.0005 (12)	0.0122 (10)	−0.0002 (12)
C2	0.0553 (13)	0.0729 (15)	0.0680 (15)	−0.0135 (11)	0.0141 (11)	−0.0142 (12)
C3	0.0628 (14)	0.0727 (15)	0.0639 (15)	−0.0098 (12)	0.0192 (12)	−0.0175 (12)
C5	0.0508 (12)	0.0765 (16)	0.0612 (15)	−0.0081 (11)	0.0082 (10)	−0.0097 (12)
C6	0.0572 (13)	0.0746 (16)	0.0500 (13)	−0.0030 (11)	0.0099 (10)	−0.0063 (11)
C12	0.0811 (18)	0.106 (2)	0.094 (2)	−0.0108 (16)	0.0447 (16)	−0.0271 (17)

S1—C10	1.709 (2)	N1—C10	1.429 (3)
S1—C7	1.717 (2)	C4—C5	1.380 (3)
C1—C2	1.384 (3)	C4—C3	1.381 (3)
C1—C6	1.389 (3)	C7—C8	1.365 (3)
C1—N2	1.414 (3)	C8—H8	0.9300
N2—C11	1.268 (3)	C2—C3	1.372 (3)
C11—C7	1.449 (3)	C2—H2	0.9300
C11—H11	0.9300	C3—H3	0.9300
C9—C10	1.350 (3)	C5—C6	1.370 (3)
C9—C8	1.400 (3)	C5—H5	0.9300
C9—H9	0.9300	C6—H6	0.9300
O3—C4	1.366 (3)	C12—H12A	0.9600
O3—C12	1.420 (3)	C12—H12B	0.9600
N1—O1	1.214 (3)	C12—H12C	0.9600
N1—O2	1.232 (3)
C10—S1—C7	89.19 (10)	C11—C7—S1	119.49 (17)
C2—C1—C6	117.6 (2)	C7—C8—C9	113.0 (2)
C2—C1—N2	124.5 (2)	C7—C8—H8	123.5
C6—C1—N2	117.8 (2)	C9—C8—H8	123.5
C11—N2—C1	119.9 (2)	C3—C2—C1	121.7 (2)
N2—C11—C7	120.3 (2)	C3—C2—H2	119.2
N2—C11—H11	119.9	C1—C2—H2	119.2
C7—C11—H11	119.9	C2—C3—C4	119.8 (2)
C10—C9—C8	110.4 (2)	C2—C3—H3	120.1
C10—C9—H9	124.8	C4—C3—H3	120.1
C8—C9—H9	124.8	C6—C5—C4	120.4 (2)
C4—O3—C12	118.2 (2)	C6—C5—H5	119.8
O1—N1—O2	124.1 (2)	C4—C5—H5	119.8
O1—N1—C10	118.6 (2)	C5—C6—C1	121.2 (2)
O2—N1—C10	117.3 (2)	C5—C6—H6	119.4
C9—C10—N1	125.7 (2)	C1—C6—H6	119.4
C9—C10—S1	114.89 (17)	O3—C12—H12A	109.5
N1—C10—S1	119.41 (18)	O3—C12—H12B	109.5
O3—C4—C5	116.0 (2)	H12A—C12—H12B	109.5
O3—C4—C3	124.7 (2)	O3—C12—H12C	109.5
C5—C4—C3	119.3 (2)	H12A—C12—H12C	109.5
C8—C7—C11	128.1 (2)	H12B—C12—H12C	109.5
C8—C7—S1	112.44 (16)
C2—C1—N2—C11	30.4 (4)	C10—S1—C7—C8	0.3 (2)
C6—C1—N2—C11	−153.0 (2)	C10—S1—C7—C11	−179.7 (2)
C1—N2—C11—C7	−178.1 (2)	C11—C7—C8—C9	179.8 (2)
C8—C9—C10—N1	−178.2 (2)	S1—C7—C8—C9	−0.2 (3)
C8—C9—C10—S1	0.3 (3)	C10—C9—C8—C7	−0.1 (3)
O1—N1—C10—C9	−2.1 (4)	C6—C1—C2—C3	2.4 (4)
O2—N1—C10—C9	177.6 (3)	N2—C1—C2—C3	178.9 (2)
O1—N1—C10—S1	179.5 (2)	C1—C2—C3—C4	−0.6 (4)
O2—N1—C10—S1	−0.8 (3)	O3—C4—C3—C2	179.6 (2)
C7—S1—C10—C9	−0.4 (2)	C5—C4—C3—C2	−1.0 (4)
C7—S1—C10—N1	178.2 (2)	O3—C4—C5—C6	−179.8 (2)
C12—O3—C4—C5	178.8 (2)	C3—C4—C5—C6	0.8 (4)
C12—O3—C4—C3	−1.8 (4)	C4—C5—C6—C1	1.0 (4)
N2—C11—C7—C8	−176.2 (2)	C2—C1—C6—C5	−2.6 (4)
N2—C11—C7—S1	3.8 (3)	N2—C1—C6—C5	−179.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2i	0.93	2.48	3.292 (3)	146
C9—H9···O3ii	0.93	2.40	3.273 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.93	2.48	3.292 (3)	146
C9—H9⋯O3ii	0.93	2.40	3.273 (3)	156

Symmetry codes: (i) ; (ii) .