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

The dihedral angle between the benzene and thio-phene rings in the title compound, C(12)H(10)N(2)O(3)S, is 27.94 (13)°. 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. (2009 ▶); Ceylan et al. (2011 ▶).

Experimental

Crystal data

C12H10N2O3S

M = 262.28

Orthorhombic,

a = 6.6825 (6) Å

b = 7.7926 (5) Å

c = 23.7180 (12) Å

V = 1235.09 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.59 × 0.39 × 0.05 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.974, T max = 0.974

5645 measured reflections

2599 independent reflections

1799 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.069

S = 0.93

2599 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1067 Friedel pairs

Flack parameter: −0.04 (8)

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/S160053681200044X/bt5776sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200044X/bt5776Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200044X/bt5776Isup3.cml

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

C12H10N2O3S	F(000) = 544
Mr = 262.28	Dx = 1.411 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6785 reflections
a = 6.6825 (6) Å	θ = 2.6–27.2°
b = 7.7926 (5) Å	µ = 0.26 mm−1
c = 23.7180 (12) Å	T = 296 K
V = 1235.09 (15) Å3	Plate, yellow
Z = 4	0.59 × 0.39 × 0.05 mm

Stoe IPDS II diffractometer	2599 independent reflections
Radiation source: fine-focus sealed tube	1799 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 6.67 pixels mm-1	θmax = 26.8°, θmin = 2.8°
rotation method scans	h = −6→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.974, Tmax = 0.974	l = −29→29
5645 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) = 0.069	w = 1/[σ2(Fo2) + (0.0284P)2] where P = (Fo2 + 2Fc2)/3
S = 0.93	(Δ/σ)max < 0.001
2599 reflections	Δρmax = 0.12 e Å−3
163 parameters	Δρmin = −0.21 e Å−3
0 restraints	Absolute structure: Flack (1983), 1067 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (8)

Experimental. 108 frames, detector distance = 120 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
S1	0.93052 (10)	0.80791 (7)	0.16132 (3)	0.06181 (17)
O4	0.4298 (3)	0.59180 (17)	0.04012 (7)	0.0711 (5)
C7	0.5822 (4)	0.2075 (3)	0.11420 (10)	0.0649 (6)
H7	0.6780	0.1749	0.1405	0.078*
C11	0.4265 (4)	0.4242 (3)	0.05670 (10)	0.0572 (5)
C6	0.5750 (4)	0.3765 (3)	0.09543 (9)	0.0568 (6)
N2	0.7021 (4)	0.5066 (2)	0.11656 (8)	0.0613 (5)
C1	1.1502 (4)	0.8578 (3)	0.19332 (10)	0.0561 (6)
O1	1.3451 (3)	1.0633 (2)	0.23403 (9)	0.0968 (7)
C8	0.4476 (5)	0.0878 (3)	0.09384 (11)	0.0735 (7)
H8	0.4546	−0.0255	0.1060	0.088*
N1	1.1877 (4)	1.0325 (3)	0.20966 (9)	0.0695 (6)
C5	0.8791 (4)	0.4701 (3)	0.13135 (10)	0.0614 (6)
H5	0.9268	0.3592	0.1259	0.074*
C9	0.3052 (5)	0.1357 (3)	0.05614 (12)	0.0744 (8)
H9	0.2147	0.0546	0.0428	0.089*
C4	1.0087 (3)	0.5975 (3)	0.15657 (11)	0.0562 (6)
O2	1.0599 (4)	1.1402 (2)	0.19817 (8)	0.0883 (6)
C10	0.2928 (4)	0.3033 (3)	0.03729 (10)	0.0671 (6)
H10	0.1944	0.3343	0.0115	0.081*
C3	1.1934 (4)	0.5742 (3)	0.17897 (11)	0.0675 (7)
H3	1.2582	0.4686	0.1798	0.081*
C2	1.2765 (4)	0.7248 (3)	0.20070 (11)	0.0685 (7)
H2	1.4013	0.7323	0.2178	0.082*
C13	0.2741 (5)	0.6489 (3)	0.00482 (13)	0.0897 (9)
H13A	0.2933	0.7682	−0.0037	0.135*
H13B	0.1481	0.6339	0.0236	0.135*
H13C	0.2748	0.5837	−0.0295	0.135*

	U11	U22	U33	U12	U13	U23
S1	0.0602 (3)	0.0558 (3)	0.0694 (4)	0.0056 (3)	−0.0122 (4)	0.0013 (3)
O4	0.0705 (11)	0.0537 (8)	0.0889 (13)	−0.0040 (9)	−0.0184 (12)	0.0056 (8)
C7	0.0688 (15)	0.0610 (12)	0.0650 (14)	−0.0041 (14)	0.0017 (15)	0.0057 (12)
C11	0.0587 (13)	0.0531 (11)	0.0598 (14)	−0.0041 (12)	0.0017 (14)	−0.0040 (9)
C6	0.0613 (14)	0.0544 (11)	0.0548 (14)	−0.0042 (12)	0.0049 (14)	−0.0065 (9)
N2	0.0669 (15)	0.0554 (10)	0.0615 (12)	−0.0027 (10)	−0.0049 (11)	−0.0060 (9)
C1	0.0587 (15)	0.0552 (12)	0.0543 (14)	−0.0048 (10)	−0.0054 (12)	0.0014 (10)
O1	0.0939 (17)	0.0998 (13)	0.0967 (15)	−0.0252 (12)	−0.0188 (13)	−0.0225 (11)
C8	0.087 (2)	0.0523 (12)	0.0808 (19)	−0.0052 (15)	0.0142 (18)	0.0050 (12)
N1	0.0762 (16)	0.0724 (14)	0.0598 (14)	−0.0166 (13)	−0.0058 (12)	−0.0045 (10)
C5	0.0612 (19)	0.0548 (12)	0.0681 (16)	0.0022 (11)	−0.0007 (13)	−0.0027 (11)
C9	0.0749 (18)	0.0668 (15)	0.0813 (19)	−0.0151 (14)	0.0057 (18)	−0.0075 (13)
C4	0.0531 (14)	0.0539 (11)	0.0616 (15)	0.0036 (9)	−0.0017 (12)	−0.0006 (11)
O2	0.1080 (15)	0.0631 (10)	0.0937 (14)	0.0073 (12)	−0.0122 (15)	−0.0038 (9)
C10	0.0635 (15)	0.0672 (14)	0.0706 (16)	−0.0065 (13)	−0.0015 (14)	−0.0088 (13)
C3	0.0599 (17)	0.0611 (13)	0.0816 (19)	0.0080 (13)	−0.0018 (14)	0.0015 (12)
C2	0.0580 (15)	0.0760 (16)	0.0714 (16)	−0.0016 (13)	−0.0133 (13)	0.0070 (13)
C13	0.081 (2)	0.0754 (16)	0.112 (2)	0.0061 (15)	−0.0289 (19)	0.0128 (15)

S1—C1	1.698 (2)	C8—H8	0.9300
S1—C4	1.725 (2)	N1—O2	1.228 (3)
O4—C11	1.364 (2)	C5—C4	1.447 (3)
O4—C13	1.408 (3)	C5—H5	0.9300
C7—C8	1.383 (4)	C9—C10	1.383 (3)
C7—C6	1.391 (3)	C9—H9	0.9300
C7—H7	0.9300	C4—C3	1.356 (3)
C11—C10	1.378 (3)	C10—H10	0.9300
C11—C6	1.402 (3)	C3—C2	1.397 (3)
C6—N2	1.414 (3)	C3—H3	0.9300
N2—C5	1.266 (3)	C2—H2	0.9300
C1—C2	1.348 (3)	C13—H13A	0.9600
C1—N1	1.437 (3)	C13—H13B	0.9600
O1—N1	1.224 (3)	C13—H13C	0.9600
C8—C9	1.358 (4)
C1—S1—C4	89.14 (11)	C4—C5—H5	119.3
C11—O4—C13	117.5 (2)	C8—C9—C10	120.9 (2)
C8—C7—C6	120.3 (2)	C8—C9—H9	119.5
C8—C7—H7	119.9	C10—C9—H9	119.5
C6—C7—H7	119.9	C3—C4—C5	127.9 (2)
O4—C11—C10	124.7 (2)	C3—C4—S1	112.20 (18)
O4—C11—C6	115.5 (2)	C5—C4—S1	119.86 (17)
C10—C11—C6	119.8 (2)	C11—C10—C9	119.9 (2)
C7—C6—C11	119.0 (2)	C11—C10—H10	120.0
C7—C6—N2	123.0 (2)	C9—C10—H10	120.0
C11—C6—N2	117.87 (19)	C4—C3—C2	113.2 (2)
C5—N2—C6	119.9 (2)	C4—C3—H3	123.4
C2—C1—N1	125.7 (2)	C2—C3—H3	123.4
C2—C1—S1	115.04 (17)	C1—C2—C3	110.4 (2)
N1—C1—S1	119.23 (18)	C1—C2—H2	124.8
C9—C8—C7	120.0 (2)	C3—C2—H2	124.8
C9—C8—H8	120.0	O4—C13—H13A	109.5
C7—C8—H8	120.0	O4—C13—H13B	109.5
O1—N1—O2	124.6 (2)	H13A—C13—H13B	109.5
O1—N1—C1	117.6 (2)	O4—C13—H13C	109.5
O2—N1—C1	117.8 (2)	H13A—C13—H13C	109.5
N2—C5—C4	121.3 (2)	H13B—C13—H13C	109.5
N2—C5—H5	119.3
C13—O4—C11—C10	6.3 (4)	S1—C1—N1—O2	−2.0 (3)
C13—O4—C11—C6	−175.0 (2)	C6—N2—C5—C4	−175.9 (2)
C8—C7—C6—C11	1.5 (4)	C7—C8—C9—C10	0.4 (4)
C8—C7—C6—N2	176.9 (2)	N2—C5—C4—C3	173.5 (3)
O4—C11—C6—C7	−179.7 (2)	N2—C5—C4—S1	−5.6 (3)
C10—C11—C6—C7	−1.0 (3)	C1—S1—C4—C3	0.1 (2)
O4—C11—C6—N2	4.6 (3)	C1—S1—C4—C5	179.4 (2)
C10—C11—C6—N2	−176.7 (2)	O4—C11—C10—C9	178.8 (2)
C7—C6—N2—C5	33.7 (4)	C6—C11—C10—C9	0.2 (4)
C11—C6—N2—C5	−150.8 (2)	C8—C9—C10—C11	0.1 (4)
C4—S1—C1—C2	−0.4 (2)	C5—C4—C3—C2	−179.0 (2)
C4—S1—C1—N1	179.1 (2)	S1—C4—C3—C2	0.2 (3)
C6—C7—C8—C9	−1.2 (4)	N1—C1—C2—C3	−178.9 (2)
C2—C1—N1—O1	−2.5 (4)	S1—C1—C2—C3	0.6 (3)
S1—C1—N1—O1	178.03 (18)	C4—C3—C2—C1	−0.5 (3)
C2—C1—N1—O2	177.5 (2)

Cg2 is the centroid of the C6–C11 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Cg2i	0.93	2.77	3.605 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C6–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Cg2i	0.93	2.77	3.605 (3)	149

Symmetry code: (i) .