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

In the crystal structure of the title compound, C(12)H(10)N(2)O(2)S, the benzene and the 2-nitro-thio-phene rings make a dihedral angle of 7.47 (12)°. The dihedral angle between the nitro group and the attached ring is 1.9 (6)°.

Related literature

For related structures, see: Demirtaş et al. (2009 ▶); Ceylan et al. (2011 ▶).

Experimental

Crystal data

C12H10N2O2S

M = 246.28

Monoclinic,

a = 4.7661 (4) Å

b = 22.8201 (18) Å

c = 10.7793 (7) Å

β = 92.704 (7)°

V = 1171.08 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.17 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction SuperNova Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.771, T max = 1.000

3997 measured reflections

2211 independent reflections

1549 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.177

S = 1.05

2211 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.28 e Å−3

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 (Dolomanov et al. 2009 ▶), WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812026062/nc2283sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026062/nc2283Isup2.hkl

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

C12H10N2O2S	F(000) = 512
Mr = 246.28	Dx = 1.397 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1442 reflections
a = 4.7661 (4) Å	θ = 3.3–27.6°
b = 22.8201 (18) Å	µ = 0.26 mm−1
c = 10.7793 (7) Å	T = 296 K
β = 92.704 (7)°	Prism, brown
V = 1171.08 (15) Å3	0.17 × 0.15 × 0.12 mm
Z = 4

Oxford Diffraction SuperNova Eos diffractometer	2211 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1549 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.064
Detector resolution: 16.0454 pixels mm-1	θmax = 26.0°, θmin = 3.3°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −27→26
Tmin = 0.771, Tmax = 1.000	l = −13→8
3997 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.177	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0778P)2] where P = (Fo2 + 2Fc2)/3
2211 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.28 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
C1	1.8771 (9)	0.51221 (18)	0.2226 (4)	0.0792 (14)
H1A	2.0022	0.5083	0.1558	0.119*
H1B	1.9835	0.5118	0.3005	0.119*
H1C	1.7765	0.5485	0.2141	0.119*
C2	1.6709 (7)	0.46177 (17)	0.2185 (4)	0.0576 (11)
C3	1.5819 (8)	0.43632 (17)	0.1076 (4)	0.0586 (11)
H3	1.6539	0.4500	0.0343	0.070*
C4	1.3897 (7)	0.39125 (16)	0.1021 (3)	0.0498 (9)
H4	1.3321	0.3754	0.0256	0.060*
C5	1.2814 (7)	0.36934 (15)	0.2103 (3)	0.0409 (8)
C6	1.3763 (8)	0.39378 (17)	0.3217 (3)	0.0498 (9)
H6	1.3103	0.3794	0.3956	0.060*
C7	1.5673 (8)	0.43920 (17)	0.3253 (4)	0.0623 (11)
H7	1.6273	0.4549	0.4017	0.075*
C8	0.9566 (7)	0.30543 (15)	0.1167 (3)	0.0436 (8)
H8	0.9950	0.3238	0.0424	0.052*
C9	0.7549 (7)	0.25849 (15)	0.1140 (3)	0.0407 (8)
C10	0.6197 (7)	0.23554 (16)	0.0104 (3)	0.0501 (10)
H10	0.6498	0.2486	−0.0696	0.060*
C11	0.4313 (7)	0.19048 (16)	0.0363 (3)	0.0479 (9)
H11	0.3243	0.1699	−0.0236	0.057*
C12	0.4260 (7)	0.18089 (14)	0.1598 (3)	0.0379 (8)
N1	1.0843 (6)	0.32285 (12)	0.2158 (2)	0.0413 (7)
N2	0.2502 (6)	0.13966 (14)	0.2189 (3)	0.0488 (8)
O1	0.2643 (6)	0.13733 (12)	0.3329 (2)	0.0663 (8)
O2	0.0953 (6)	0.10886 (13)	0.1531 (3)	0.0692 (8)
S1	0.64676 (18)	0.22535 (4)	0.24745 (7)	0.0417 (3)

	U11	U22	U33	U12	U13	U23
C1	0.058 (3)	0.047 (2)	0.133 (4)	−0.009 (2)	0.009 (3)	−0.004 (3)
C2	0.036 (2)	0.042 (2)	0.095 (3)	0.0044 (17)	0.008 (2)	0.003 (2)
C3	0.052 (2)	0.050 (2)	0.074 (3)	0.000 (2)	0.010 (2)	0.013 (2)
C4	0.049 (2)	0.051 (2)	0.050 (2)	0.0003 (19)	0.0058 (17)	0.0034 (18)
C5	0.0348 (19)	0.0387 (19)	0.0492 (19)	0.0028 (15)	0.0013 (15)	0.0042 (16)
C6	0.048 (2)	0.052 (2)	0.049 (2)	−0.0071 (19)	−0.0010 (16)	0.0026 (18)
C7	0.055 (2)	0.058 (3)	0.073 (3)	−0.008 (2)	−0.005 (2)	−0.008 (2)
C8	0.042 (2)	0.050 (2)	0.0386 (17)	0.0005 (17)	0.0031 (15)	0.0093 (16)
C9	0.041 (2)	0.044 (2)	0.0360 (17)	0.0019 (16)	−0.0023 (14)	0.0015 (15)
C10	0.051 (2)	0.065 (2)	0.0339 (17)	−0.006 (2)	−0.0021 (16)	0.0042 (17)
C11	0.049 (2)	0.058 (2)	0.0354 (17)	−0.0040 (19)	−0.0052 (15)	−0.0093 (17)
C12	0.0331 (18)	0.0394 (19)	0.0413 (16)	0.0046 (15)	0.0039 (14)	−0.0025 (15)
N1	0.0417 (16)	0.0423 (16)	0.0393 (14)	0.0015 (14)	−0.0032 (12)	0.0033 (13)
N2	0.0507 (19)	0.0464 (19)	0.0493 (17)	0.0056 (16)	0.0041 (15)	0.0033 (15)
O1	0.085 (2)	0.0671 (18)	0.0480 (15)	−0.0064 (16)	0.0113 (14)	0.0092 (14)
O2	0.0684 (19)	0.0685 (18)	0.0704 (17)	−0.0220 (16)	0.0005 (15)	−0.0036 (16)
S1	0.0472 (6)	0.0464 (6)	0.0313 (4)	0.0021 (4)	−0.0015 (4)	−0.0003 (4)

C1—C2	1.513 (5)	C7—H7	0.9300
C1—H1A	0.9600	C8—N1	1.269 (4)
C1—H1B	0.9600	C8—C9	1.439 (5)
C1—H1C	0.9600	C8—H8	0.9300
C2—C7	1.374 (5)	C9—C10	1.366 (4)
C2—C3	1.378 (5)	C9—S1	1.725 (3)
C3—C4	1.377 (5)	C10—C11	1.402 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.391 (4)	C11—C12	1.351 (4)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.381 (5)	C12—N2	1.430 (4)
C5—N1	1.420 (4)	C12—S1	1.713 (3)
C6—C7	1.379 (5)	N2—O2	1.222 (4)
C6—H6	0.9300	N2—O1	1.228 (4)
C2—C1—H1A	109.5	C2—C7—H7	119.3
C2—C1—H1B	109.5	C6—C7—H7	119.3
H1A—C1—H1B	109.5	N1—C8—C9	123.0 (3)
C2—C1—H1C	109.5	N1—C8—H8	118.5
H1A—C1—H1C	109.5	C9—C8—H8	118.5
H1B—C1—H1C	109.5	C10—C9—C8	126.2 (3)
C7—C2—C3	117.4 (4)	C10—C9—S1	111.4 (3)
C7—C2—C1	121.3 (4)	C8—C9—S1	122.4 (2)
C3—C2—C1	121.3 (4)	C9—C10—C11	113.6 (3)
C4—C3—C2	122.0 (4)	C9—C10—H10	123.2
C4—C3—H3	119.0	C11—C10—H10	123.2
C2—C3—H3	119.0	C12—C11—C10	110.9 (3)
C3—C4—C5	120.3 (4)	C12—C11—H11	124.6
C3—C4—H4	119.8	C10—C11—H11	124.6
C5—C4—H4	119.8	C11—C12—N2	125.8 (3)
C6—C5—C4	117.7 (3)	C11—C12—S1	114.1 (3)
C6—C5—N1	117.1 (3)	N2—C12—S1	120.1 (2)
C4—C5—N1	125.2 (3)	C8—N1—C5	119.4 (3)
C7—C6—C5	121.1 (3)	O2—N2—O1	124.0 (3)
C7—C6—H6	119.4	O2—N2—C12	118.1 (3)
C5—C6—H6	119.4	O1—N2—C12	118.0 (3)
C2—C7—C6	121.4 (4)	C12—S1—C9	89.98 (15)
C7—C2—C3—C4	2.1 (6)	C9—C10—C11—C12	0.8 (4)
C1—C2—C3—C4	−178.5 (3)	C10—C11—C12—N2	177.6 (3)
C2—C3—C4—C5	−0.9 (6)	C10—C11—C12—S1	−0.2 (4)
C3—C4—C5—C6	−0.9 (5)	C9—C8—N1—C5	179.7 (3)
C3—C4—C5—N1	−179.5 (3)	C6—C5—N1—C8	168.5 (3)
C4—C5—C6—C7	1.4 (5)	C4—C5—N1—C8	−12.8 (5)
N1—C5—C6—C7	−179.9 (3)	C11—C12—N2—O2	2.2 (5)
C3—C2—C7—C6	−1.6 (6)	S1—C12—N2—O2	179.8 (3)
C1—C2—C7—C6	179.1 (4)	C11—C12—N2—O1	−177.9 (3)
C5—C6—C7—C2	−0.2 (6)	S1—C12—N2—O1	−0.2 (4)
N1—C8—C9—C10	−176.6 (3)	C11—C12—S1—C9	−0.3 (3)
N1—C8—C9—S1	5.4 (5)	N2—C12—S1—C9	−178.2 (3)
C8—C9—C10—C11	−179.2 (3)	C10—C9—S1—C12	0.7 (3)
S1—C9—C10—C11	−1.0 (4)	C8—C9—S1—C12	179.0 (3)