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

The title compound, C(12)H(10)N(2)O(2)S, is a Schiff base formed from p-toluidine and 5-nitro-thio-phene-2-carbaldehyde. The C=N bond adopts an E configuration. The benzene and thio-phene rings form a dihedral angle of 9.2 (1)°.

Related literature

For the use of Schiff bases as polydentate ligands, see: Bourget-Merle et al.(2002 ▶); Halbach & Hamaker (2006 ▶); Meiswinkel & Werner (2004 ▶); Xiao et al. (2006 ▶); Lagadic (2006 ▶). For their biological activity, see: Siddiqui et al. (2006 ▶).

Experimental

Crystal data

C12H10N2O2S

M = 246.28

Monoclinic,

a = 4.7606 (4) Å

b = 22.415 (2) Å

c = 10.7008 (15) Å

β = 92.566 (13)°

V = 1140.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 113 K

0.20 × 0.18 × 0.12 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002 ▶) T min = 0.947, T max = 0.968

14437 measured reflections

2699 independent reflections

2325 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 1.09

2699 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Crystal Impact, 2009 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030297/ld2020sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030297/ld2020Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030297/ld2020Isup3.cml

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

C12H10N2O2S	F(000) = 512
Mr = 246.28	Dx = 1.434 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.7606 (4) Å	Cell parameters from 4173 reflections
b = 22.415 (2) Å	θ = 1.8–27.9°
c = 10.7008 (15) Å	µ = 0.27 mm−1
β = 92.566 (13)°	T = 113 K
V = 1140.7 (2) Å3	Prism, colorless
Z = 4	0.20 × 0.18 × 0.12 mm

Rigaku Saturn724 CCD diffractometer	2699 independent reflections
Radiation source: rotating anode	2325 reflections with I > 2σ(I)
multilayer	Rint = 0.043
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 1.8°
ω and φ scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2002)	k = −29→29
Tmin = 0.947, Tmax = 0.968	l = −13→14
14437 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) = 0.098	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0505P)2 + 0.1298P] where P = (Fo2 + 2Fc2)/3
2699 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. Rigaku CrystalClear-SM Expert 2.0 r2

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	0.12948 (8)	0.223694 (17)	0.24141 (3)	0.01725 (12)
O1	−0.4301 (2)	0.10562 (5)	0.14443 (11)	0.0279 (3)
O2	−0.2638 (2)	0.13512 (5)	0.32720 (10)	0.0257 (3)
N1	0.5743 (3)	0.32247 (6)	0.21001 (11)	0.0170 (3)
N2	−0.2748 (3)	0.13695 (6)	0.21144 (12)	0.0200 (3)
C1	1.3858 (3)	0.51381 (7)	0.21589 (19)	0.0294 (4)
H1A	1.5510	0.5020	0.1704	0.044*
H1B	1.4432	0.5230	0.3028	0.044*
H1C	1.2998	0.5492	0.1763	0.044*
C2	1.1750 (3)	0.46324 (7)	0.21303 (16)	0.0220 (3)
C3	1.0879 (3)	0.43701 (7)	0.10002 (15)	0.0223 (3)
H3	1.1645	0.4507	0.0248	0.027*
C4	0.8909 (3)	0.39115 (7)	0.09487 (14)	0.0197 (3)
H4	0.8337	0.3742	0.0164	0.024*
C5	0.7759 (3)	0.36966 (7)	0.20461 (14)	0.0169 (3)
C6	0.8680 (3)	0.39494 (7)	0.31778 (14)	0.0199 (3)
H6	0.7965	0.3804	0.3935	0.024*
C7	1.0628 (3)	0.44113 (7)	0.32203 (16)	0.0233 (4)
H7	1.1207	0.4579	0.4005	0.028*
C8	0.4454 (3)	0.30556 (7)	0.10888 (14)	0.0189 (3)
H8	0.4859	0.3248	0.0327	0.023*
C9	0.2385 (3)	0.25772 (7)	0.10682 (14)	0.0173 (3)
C10	0.1041 (3)	0.23474 (7)	0.00118 (14)	0.0208 (3)
H10	0.1382	0.2483	−0.0809	0.025*
C11	−0.0895 (3)	0.18913 (7)	0.02644 (14)	0.0194 (3)
H11	−0.2003	0.1683	−0.0354	0.023*
C12	−0.0955 (3)	0.17906 (7)	0.15201 (14)	0.0166 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0186 (2)	0.0195 (2)	0.01358 (19)	0.00044 (15)	−0.00004 (15)	−0.00052 (14)
O1	0.0285 (6)	0.0275 (6)	0.0275 (6)	−0.0102 (5)	−0.0009 (5)	−0.0022 (5)
O2	0.0313 (7)	0.0288 (6)	0.0174 (6)	−0.0008 (5)	0.0046 (5)	0.0029 (5)
N1	0.0166 (6)	0.0168 (6)	0.0174 (6)	0.0015 (5)	0.0004 (5)	0.0009 (5)
N2	0.0205 (7)	0.0200 (7)	0.0195 (7)	0.0020 (5)	0.0019 (5)	0.0003 (5)
C1	0.0210 (8)	0.0204 (8)	0.0472 (11)	−0.0026 (7)	0.0047 (8)	0.0001 (8)
C2	0.0153 (7)	0.0165 (8)	0.0345 (9)	0.0031 (6)	0.0018 (7)	0.0011 (7)
C3	0.0198 (8)	0.0211 (8)	0.0264 (8)	0.0025 (6)	0.0061 (7)	0.0057 (7)
C4	0.0202 (8)	0.0203 (8)	0.0187 (8)	0.0022 (6)	0.0008 (6)	−0.0005 (6)
C5	0.0134 (7)	0.0162 (7)	0.0210 (8)	0.0022 (6)	0.0002 (6)	0.0009 (6)
C6	0.0191 (7)	0.0218 (8)	0.0187 (7)	−0.0004 (6)	−0.0004 (6)	0.0023 (6)
C7	0.0222 (8)	0.0230 (8)	0.0245 (8)	−0.0011 (7)	−0.0025 (7)	−0.0018 (7)
C8	0.0194 (7)	0.0206 (8)	0.0168 (7)	0.0007 (6)	0.0019 (6)	0.0025 (6)
C9	0.0172 (7)	0.0189 (7)	0.0158 (7)	0.0018 (6)	0.0013 (6)	0.0005 (6)
C10	0.0211 (8)	0.0272 (8)	0.0142 (7)	−0.0010 (7)	0.0004 (6)	0.0013 (6)
C11	0.0185 (7)	0.0224 (8)	0.0173 (7)	−0.0005 (6)	0.0007 (6)	−0.0032 (6)
C12	0.0157 (7)	0.0168 (7)	0.0173 (7)	0.0007 (6)	0.0013 (6)	−0.0016 (6)

S1—C12	1.7237 (15)	C3—H3	0.9500
S1—C9	1.7298 (15)	C4—C5	1.403 (2)
O1—N2	1.2271 (16)	C4—H4	0.9500
O2—N2	1.2382 (16)	C5—C6	1.390 (2)
N1—C8	1.277 (2)	C6—C7	1.389 (2)
N1—C5	1.4312 (19)	C6—H6	0.9500
N2—C12	1.4398 (19)	C7—H7	0.9500
C1—C2	1.513 (2)	C8—C9	1.456 (2)
C1—H1A	0.9800	C8—H8	0.9500
C1—H1B	0.9800	C9—C10	1.374 (2)
C1—H1C	0.9800	C10—C11	1.411 (2)
C2—C3	1.391 (2)	C10—H10	0.9500
C2—C7	1.395 (2)	C11—C12	1.364 (2)
C3—C4	1.391 (2)	C11—H11	0.9500
C12—S1—C9	89.77 (7)	C4—C5—N1	125.10 (13)
C8—N1—C5	118.86 (13)	C7—C6—C5	121.08 (15)
O1—N2—O2	124.27 (13)	C7—C6—H6	119.5
O1—N2—C12	118.08 (13)	C5—C6—H6	119.5
O2—N2—C12	117.65 (13)	C6—C7—C2	121.15 (15)
C2—C1—H1A	109.5	C6—C7—H7	119.4
C2—C1—H1B	109.5	C2—C7—H7	119.4
H1A—C1—H1B	109.5	N1—C8—C9	122.04 (14)
C2—C1—H1C	109.5	N1—C8—H8	119.0
H1A—C1—H1C	109.5	C9—C8—H8	119.0
H1B—C1—H1C	109.5	C10—C9—C8	125.35 (14)
C3—C2—C7	117.78 (14)	C10—C9—S1	111.94 (12)
C3—C2—C1	120.39 (15)	C8—C9—S1	122.70 (11)
C7—C2—C1	121.84 (15)	C9—C10—C11	113.47 (14)
C4—C3—C2	121.40 (15)	C9—C10—H10	123.3
C4—C3—H3	119.3	C11—C10—H10	123.3
C2—C3—H3	119.3	C12—C11—C10	110.57 (14)
C3—C4—C5	120.55 (14)	C12—C11—H11	124.7
C3—C4—H4	119.7	C10—C11—H11	124.7
C5—C4—H4	119.7	C11—C12—N2	125.62 (14)
C6—C5—C4	118.01 (14)	C11—C12—S1	114.25 (12)
C6—C5—N1	116.87 (13)	N2—C12—S1	120.10 (11)
C7—C2—C3—C4	1.4 (2)	N1—C8—C9—S1	5.1 (2)
C1—C2—C3—C4	−178.92 (14)	C12—S1—C9—C10	0.04 (12)
C2—C3—C4—C5	−0.6 (2)	C12—S1—C9—C8	179.15 (13)
C3—C4—C5—C6	−0.9 (2)	C8—C9—C10—C11	−179.16 (14)
C3—C4—C5—N1	−179.45 (13)	S1—C9—C10—C11	−0.08 (17)
C8—N1—C5—C6	167.13 (14)	C9—C10—C11—C12	0.09 (19)
C8—N1—C5—C4	−14.3 (2)	C10—C11—C12—N2	178.01 (13)
C4—C5—C6—C7	1.6 (2)	C10—C11—C12—S1	−0.06 (17)
N1—C5—C6—C7	−179.80 (14)	O1—N2—C12—C11	2.7 (2)
C5—C6—C7—C2	−0.7 (2)	O2—N2—C12—C11	−176.72 (14)
C3—C2—C7—C6	−0.8 (2)	O1—N2—C12—S1	−179.35 (11)
C1—C2—C7—C6	179.55 (14)	O2—N2—C12—S1	1.25 (18)
C5—N1—C8—C9	179.73 (13)	C9—S1—C12—C11	0.01 (12)
N1—C8—C9—C10	−175.90 (15)	C9—S1—C12—N2	−178.17 (12)