N-(3-Nitro-benzyl-idene)aniline.

In the title compound, C(13)H(10)N(2)O(2), a Schiff base derivative, the dihedral angle between the two aromatic rings is 31.58 (3)°. The C=N double bond is essentially coplanar with the nitro-phenyl ring. The torsion angle of the imine double bond is 175.97 (13)°, indicating that the C=N double bond is in a trans configuration. The crystal structure is stabilized by C-H⋯O contacts and π-π inter-actions (centroid-centroid distances of 3.807 and 3.808Å).

Related literature

Choi et al. (2000 ▶) and Nakamura et al. (1999 ▶) discuss the use of Schiff bases in the reduction of thionyl chloride, while Maruyama et al. (1995 ▶) and Burrows et al. (1996 ▶) describe their use in degradation processes. Hodnett & Mooney (1970 ▶), Rajavel et al. (2008 ▶) and Yu et al. (2007 ▶) discuss anti­neoplastic, anti­bacterial and anti­fungal activities, respectively. Hartley et al. (2002 ▶), Torregrosa et al. (2005 ▶) and Naeimi et al. (2008 ▶) describe different synthetic routes towards Schiff bases. Landy (1989 ▶) describes their role in biological redox systems. Yoon et al. (1990 ▶) and Park et al. (1998 ▶) discuss properties of Schiff base complexes such as alkene epoxidation and oxygen absorption by cobalt(II) complexes. Flack (1983 ▶) discusses the Rogers’s parameter for the characterization of enanti­o­morphic-polar compounds.

Experimental

Crystal data

C13H10N2O2

M = 226.23

Orthorhombic,

a = 7.3177 (6) Å

b = 12.1022 (11) Å

c = 12.4672 (12) Å

V = 1104.10 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 (2) K

0.48 × 0.48 × 0.46 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: none

9868 measured reflections

1585 independent reflections

1421 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.04

1585 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.14 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808036970/zl2143sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808036970/zl2143Isup2.hkl

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

C13H10N2O2	F000 = 472
Mr = 226.23	Dx = 1.361 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7899 reflections
a = 7.3177 (6) Å	θ = 3.7–25.8º
b = 12.1022 (11) Å	µ = 0.09 mm−1
c = 12.4672 (12) Å	T = 173 (2) K
V = 1104.10 (17) Å3	Block, colourless
Z = 4	0.48 × 0.48 × 0.46 mm

Stoe IPDSII two-circle diffractometer	1421 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
Monochromator: graphite	θmax = 29.5º
T = 173(2) K	θmin = 3.6º
ω scans	h = −9→8
Absorption correction: none	k = −16→14
9868 measured reflections	l = −15→17
1585 independent 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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0638P)2 + 0.081P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1585 reflections	Δρmax = 0.26 e Å−3
154 parameters	Δρmin = −0.14 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
N1	0.85150 (17)	0.74236 (10)	0.59232 (10)	0.0265 (3)
N2	0.9518 (2)	0.83182 (11)	0.11436 (10)	0.0339 (3)
O1	0.9459 (2)	0.90457 (11)	0.04548 (10)	0.0507 (4)
O2	0.9936 (2)	0.73588 (10)	0.09536 (9)	0.0525 (4)
C1	0.9027 (2)	0.72475 (11)	0.49536 (12)	0.0255 (3)
H1	0.9530	0.6549	0.4771	0.031*
C2	0.8855 (2)	0.81012 (11)	0.41137 (12)	0.0239 (3)
C3	0.9276 (2)	0.78262 (11)	0.30530 (11)	0.0243 (3)
H3	0.9685	0.7104	0.2876	0.029*
C4	0.9088 (2)	0.86252 (12)	0.22632 (11)	0.0262 (3)
C5	0.8499 (2)	0.96943 (12)	0.24807 (12)	0.0296 (3)
H5	0.8383	1.0225	0.1924	0.036*
C6	0.8086 (2)	0.99625 (12)	0.35358 (13)	0.0314 (4)
H6	0.7678	1.0687	0.3705	0.038*
C7	0.8262 (2)	0.91791 (12)	0.43499 (12)	0.0277 (3)
H7	0.7979	0.9375	0.5069	0.033*
C11	0.86161 (19)	0.65339 (11)	0.66706 (11)	0.0239 (3)
C12	0.9017 (2)	0.67860 (12)	0.77429 (12)	0.0291 (3)
H12	0.9229	0.7531	0.7947	0.035*
C13	0.9105 (2)	0.59535 (14)	0.85102 (12)	0.0337 (4)
H13	0.9399	0.6130	0.9232	0.040*
C14	0.8763 (2)	0.48619 (13)	0.82226 (13)	0.0332 (4)
H14	0.8832	0.4292	0.8745	0.040*
C15	0.8317 (2)	0.46086 (12)	0.71627 (13)	0.0308 (3)
H15	0.8062	0.3866	0.6968	0.037*
C16	0.8244 (2)	0.54339 (12)	0.63890 (12)	0.0261 (3)
H16	0.7942	0.5253	0.5669	0.031*

	U11	U22	U33	U12	U13	U23
N1	0.0264 (6)	0.0264 (6)	0.0267 (6)	−0.0005 (5)	0.0001 (5)	0.0030 (5)
N2	0.0391 (8)	0.0365 (7)	0.0262 (6)	−0.0015 (6)	−0.0042 (6)	0.0052 (5)
O1	0.0677 (9)	0.0548 (7)	0.0297 (6)	0.0073 (8)	0.0022 (7)	0.0184 (5)
O2	0.0883 (12)	0.0392 (7)	0.0301 (6)	0.0053 (7)	0.0001 (7)	−0.0027 (5)
C1	0.0230 (7)	0.0265 (7)	0.0271 (7)	0.0011 (6)	−0.0012 (6)	0.0032 (6)
C2	0.0210 (6)	0.0249 (6)	0.0259 (7)	−0.0010 (5)	−0.0021 (6)	0.0033 (5)
C3	0.0227 (7)	0.0242 (6)	0.0261 (6)	−0.0004 (5)	−0.0030 (6)	0.0026 (5)
C4	0.0255 (7)	0.0278 (7)	0.0255 (7)	−0.0031 (6)	−0.0027 (6)	0.0043 (6)
C5	0.0279 (8)	0.0267 (7)	0.0342 (7)	−0.0009 (6)	−0.0048 (6)	0.0093 (6)
C6	0.0304 (8)	0.0239 (7)	0.0399 (8)	0.0012 (6)	−0.0006 (7)	0.0031 (6)
C7	0.0257 (7)	0.0270 (7)	0.0305 (7)	0.0009 (6)	0.0022 (6)	0.0023 (6)
C11	0.0204 (6)	0.0264 (6)	0.0248 (7)	0.0013 (5)	0.0026 (6)	0.0024 (6)
C12	0.0297 (8)	0.0313 (7)	0.0264 (7)	0.0001 (6)	0.0013 (6)	−0.0029 (6)
C13	0.0351 (8)	0.0439 (8)	0.0222 (6)	0.0014 (7)	−0.0008 (7)	0.0021 (6)
C14	0.0306 (8)	0.0376 (8)	0.0314 (7)	0.0023 (6)	0.0023 (6)	0.0127 (7)
C15	0.0297 (8)	0.0269 (7)	0.0359 (8)	−0.0003 (6)	0.0037 (7)	0.0032 (6)
C16	0.0252 (7)	0.0283 (7)	0.0247 (6)	−0.0001 (6)	0.0015 (6)	−0.0001 (6)

N1—C1	1.283 (2)	C6—C7	1.395 (2)
N1—C11	1.4258 (18)	C6—H6	0.9500
N2—O2	1.2237 (18)	C7—H7	0.9500
N2—O1	1.2306 (17)	C11—C12	1.402 (2)
N2—C4	1.4783 (19)	C11—C16	1.4034 (19)
C1—C2	1.476 (2)	C12—C13	1.391 (2)
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.398 (2)	C13—C14	1.391 (2)
C2—C7	1.4060 (19)	C13—H13	0.9500
C3—C4	1.3869 (19)	C14—C15	1.395 (2)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.390 (2)	C15—C16	1.390 (2)
C5—C6	1.388 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C1—N1—C11	118.36 (12)	C6—C7—C2	120.45 (14)
O2—N2—O1	123.54 (14)	C6—C7—H7	119.8
O2—N2—C4	118.32 (12)	C2—C7—H7	119.8
O1—N2—C4	118.14 (13)	C12—C11—C16	119.04 (13)
N1—C1—C2	121.80 (13)	C12—C11—N1	118.00 (12)
N1—C1—H1	119.1	C16—C11—N1	122.88 (13)
C2—C1—H1	119.1	C13—C12—C11	120.52 (14)
C3—C2—C7	119.15 (12)	C13—C12—H12	119.7
C3—C2—C1	119.04 (12)	C11—C12—H12	119.7
C7—C2—C1	121.81 (13)	C12—C13—C14	120.15 (14)
C4—C3—C2	118.92 (13)	C12—C13—H13	119.9
C4—C3—H3	120.5	C14—C13—H13	119.9
C2—C3—H3	120.5	C13—C14—C15	119.65 (14)
C3—C4—C5	122.76 (14)	C13—C14—H14	120.2
C3—C4—N2	118.30 (13)	C15—C14—H14	120.2
C5—C4—N2	118.94 (12)	C16—C15—C14	120.57 (14)
C6—C5—C4	118.03 (13)	C16—C15—H15	119.7
C6—C5—H5	121.0	C14—C15—H15	119.7
C4—C5—H5	121.0	C15—C16—C11	120.04 (13)
C5—C6—C7	120.69 (14)	C15—C16—H16	120.0
C5—C6—H6	119.7	C11—C16—H16	120.0
C7—C6—H6	119.7
C11—N1—C1—C2	175.97 (13)	C5—C6—C7—C2	−0.3 (2)
N1—C1—C2—C3	−174.08 (15)	C3—C2—C7—C6	0.4 (2)
N1—C1—C2—C7	5.3 (2)	C1—C2—C7—C6	−179.00 (14)
C7—C2—C3—C4	−0.3 (2)	C1—N1—C11—C12	146.81 (14)
C1—C2—C3—C4	179.08 (12)	C1—N1—C11—C16	−36.5 (2)
C2—C3—C4—C5	0.1 (2)	C16—C11—C12—C13	2.1 (2)
C2—C3—C4—N2	−179.28 (15)	N1—C11—C12—C13	179.00 (13)
O2—N2—C4—C3	3.5 (2)	C11—C12—C13—C14	−1.1 (2)
O1—N2—C4—C3	−175.59 (15)	C12—C13—C14—C15	−0.5 (2)
O2—N2—C4—C5	−175.94 (16)	C13—C14—C15—C16	1.1 (2)
O1—N2—C4—C5	5.0 (2)	C14—C15—C16—C11	−0.1 (2)
C3—C4—C5—C6	0.0 (2)	C12—C11—C16—C15	−1.5 (2)
N2—C4—C5—C6	179.38 (14)	N1—C11—C16—C15	−178.20 (13)
C4—C5—C6—C7	0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.95	2.70	3.261 (2)	118
C6—H6···O2ii	0.95	2.71	3.303 (2)	122
C7—H7···O1i	0.95	2.66	3.237 (2)	120
C13—H13···O2iii	0.95	2.64	3.541 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.95	2.70	3.261 (2)	118
C6—H6⋯O2ii	0.95	2.71	3.303 (2)	122
C7—H7⋯O1i	0.95	2.66	3.237 (2)	120
C13—H13⋯O2iii	0.95	2.64	3.541 (2)	159

Symmetry codes: (i) ; (ii) ; (iii) .