2,3-Dimethyl-N-[(E)-4-nitro-benzyl-idene]aniline.

In the title compound, C(15)H(14)N(2)O(2), the aromatic rings are oriented at a dihedral angle of 24.52 (5)°. The dihedral angle between the nitro group and its parent benzene ring is 9.22 (16)°. In the crystal, mol-ecules inter-act through aromatic π-π stacking inter-actions [centroid-centroid separations = 3.8158 (14) and 3.9139 (14) Å].

Related literature

For structural systematics of related compounds, see: Harada et al. (2004 ▶).

Experimental

Crystal data

C15H14N2O2

M = 254.28

Orthorhombic,

a = 7.1969 (5) Å

b = 11.8023 (7) Å

c = 15.3721 (8) Å

V = 1305.71 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.32 × 0.14 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.986, T max = 0.987

13172 measured reflections

1917 independent reflections

1253 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.111

S = 1.02

1917 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001932X/hb5464sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001932X/hb5464Isup2.hkl

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

C15H14N2O2	F(000) = 536
Mr = 254.28	Dx = 1.294 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1334 reflections
a = 7.1969 (5) Å	θ = 2.1–25.4°
b = 11.8023 (7) Å	µ = 0.09 mm−1
c = 15.3721 (8) Å	T = 296 K
V = 1305.71 (14) Å3	Needle, yellow
Z = 4	0.32 × 0.14 × 0.14 mm

Bruker Kappa APEXII CCD diffractometer	1917 independent reflections
Radiation source: fine-focus sealed tube	1253 reflections with I > 2σ(I)
graphite	Rint = 0.057
Detector resolution: 7.40 pixels mm-1	θmax = 28.6°, θmin = 2.2°
ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
Tmin = 0.986, Tmax = 0.987	l = −20→20
13172 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.0883P] where P = (Fo2 + 2Fc2)/3
1917 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.1409 (4)	−0.19301 (18)	0.70198 (14)	0.0997 (9)
O2	0.1083 (4)	−0.06237 (19)	0.79842 (12)	0.0941 (9)
N1	0.1128 (3)	0.34130 (16)	0.47092 (11)	0.0485 (7)
N2	0.1253 (3)	−0.0943 (2)	0.72311 (16)	0.0684 (9)
C1	0.1231 (3)	0.42218 (18)	0.40278 (13)	0.0457 (7)
C2	0.1509 (3)	0.5351 (2)	0.42653 (14)	0.0488 (8)
C3	0.1581 (4)	0.61833 (19)	0.36160 (15)	0.0549 (8)
C4	0.1353 (4)	0.5864 (2)	0.27595 (17)	0.0624 (10)
C5	0.1052 (4)	0.4755 (2)	0.25272 (16)	0.0650 (10)
C6	0.0972 (4)	0.3935 (2)	0.31593 (14)	0.0550 (8)
C7	0.1768 (4)	0.5654 (2)	0.52133 (14)	0.0679 (10)
C8	0.1878 (5)	0.7409 (2)	0.38401 (19)	0.0820 (13)
C9	0.1573 (4)	0.23940 (19)	0.45751 (14)	0.0495 (8)
C10	0.1434 (3)	0.15342 (18)	0.52625 (14)	0.0448 (7)
C11	0.1832 (3)	0.04156 (19)	0.50760 (15)	0.0525 (8)
C12	0.1753 (4)	−0.0397 (2)	0.57139 (15)	0.0551 (9)
C13	0.1287 (3)	−0.0075 (2)	0.65402 (14)	0.0500 (8)
C14	0.0878 (3)	0.1021 (2)	0.67504 (15)	0.0523 (8)
C15	0.0953 (3)	0.18289 (19)	0.61064 (14)	0.0496 (8)
H4	0.14039	0.64145	0.23274	0.0748*
H5	0.09027	0.45617	0.19450	0.0779*
H6	0.07448	0.31854	0.30059	0.0659*
H7A	0.09112	0.62429	0.53696	0.1016*
H7B	0.30167	0.59128	0.53059	0.1016*
H7C	0.15399	0.49972	0.55663	0.1016*
H8A	0.18433	0.78558	0.33184	0.1229*
H8B	0.30655	0.74981	0.41166	0.1229*
H8C	0.09161	0.76571	0.42285	0.1229*
H9	0.20007	0.21822	0.40278	0.0594*
H11	0.21572	0.02105	0.45120	0.0630*
H12	0.20116	−0.11509	0.55867	0.0661*
H14	0.05543	0.12165	0.73165	0.0627*
H15	0.06802	0.25797	0.62382	0.0596*

	U11	U22	U33	U12	U13	U23
O1	0.131 (2)	0.0586 (12)	0.1094 (16)	0.0005 (15)	0.0004 (17)	0.0307 (12)
O2	0.1205 (19)	0.1055 (16)	0.0563 (11)	−0.0025 (15)	−0.0044 (13)	0.0275 (12)
N1	0.0509 (12)	0.0484 (11)	0.0463 (11)	0.0052 (10)	0.0029 (10)	0.0042 (9)
N2	0.0614 (15)	0.0707 (16)	0.0731 (16)	−0.0068 (14)	−0.0072 (13)	0.0266 (13)
C1	0.0431 (14)	0.0477 (12)	0.0463 (12)	0.0035 (11)	0.0067 (11)	0.0043 (10)
C2	0.0454 (15)	0.0529 (13)	0.0482 (12)	0.0020 (12)	0.0069 (11)	0.0015 (11)
C3	0.0515 (16)	0.0504 (13)	0.0628 (15)	0.0051 (12)	0.0070 (12)	0.0082 (11)
C4	0.0660 (19)	0.0615 (16)	0.0596 (16)	0.0045 (15)	0.0068 (14)	0.0193 (13)
C5	0.079 (2)	0.0708 (17)	0.0453 (12)	0.0029 (16)	0.0008 (14)	0.0040 (12)
C6	0.0614 (16)	0.0526 (14)	0.0509 (14)	0.0027 (13)	0.0009 (13)	−0.0010 (12)
C7	0.081 (2)	0.0651 (16)	0.0577 (14)	−0.0020 (16)	0.0041 (14)	−0.0097 (13)
C8	0.105 (3)	0.0539 (15)	0.087 (2)	−0.0044 (18)	0.009 (2)	0.0079 (15)
C9	0.0467 (15)	0.0539 (13)	0.0479 (12)	0.0039 (12)	0.0081 (12)	0.0010 (11)
C10	0.0406 (13)	0.0467 (12)	0.0471 (13)	0.0009 (11)	0.0030 (11)	0.0026 (10)
C11	0.0578 (16)	0.0514 (13)	0.0483 (12)	0.0057 (12)	0.0043 (11)	−0.0031 (11)
C12	0.0608 (17)	0.0424 (12)	0.0621 (15)	0.0015 (12)	0.0011 (13)	0.0007 (11)
C13	0.0436 (14)	0.0550 (14)	0.0515 (12)	−0.0029 (12)	−0.0050 (12)	0.0116 (11)
C14	0.0521 (15)	0.0601 (16)	0.0447 (12)	0.0018 (13)	−0.0007 (11)	0.0014 (12)
C15	0.0521 (15)	0.0456 (12)	0.0512 (13)	0.0046 (12)	0.0015 (12)	0.0005 (11)

O1—N2	1.215 (3)	C12—C13	1.368 (3)
O2—N2	1.224 (3)	C13—C14	1.365 (3)
N1—C1	1.419 (3)	C14—C15	1.376 (3)
N1—C9	1.262 (3)	C4—H4	0.9300
N2—C13	1.476 (3)	C5—H5	0.9300
C1—C2	1.396 (3)	C6—H6	0.9300
C1—C6	1.390 (3)	C7—H7A	0.9600
C2—C3	1.401 (3)	C7—H7B	0.9600
C2—C7	1.512 (3)	C7—H7C	0.9600
C3—C4	1.379 (3)	C8—H8A	0.9600
C3—C8	1.502 (3)	C8—H8B	0.9600
C4—C5	1.374 (3)	C8—H8C	0.9600
C5—C6	1.373 (3)	C9—H9	0.9300
C9—C10	1.468 (3)	C11—H11	0.9300
C10—C11	1.381 (3)	C12—H12	0.9300
C10—C15	1.387 (3)	C14—H14	0.9300
C11—C12	1.373 (3)	C15—H15	0.9300
C1—N1—C9	120.49 (18)	C5—C4—H4	119.00
O1—N2—O2	123.9 (2)	C4—C5—H5	120.00
O1—N2—C13	118.2 (2)	C6—C5—H5	120.00
O2—N2—C13	118.0 (2)	C1—C6—H6	120.00
N1—C1—C2	117.16 (18)	C5—C6—H6	120.00
N1—C1—C6	122.56 (19)	C2—C7—H7A	109.00
C2—C1—C6	120.2 (2)	C2—C7—H7B	109.00
C1—C2—C3	119.2 (2)	C2—C7—H7C	109.00
C1—C2—C7	119.7 (2)	H7A—C7—H7B	110.00
C3—C2—C7	121.1 (2)	H7A—C7—H7C	109.00
C2—C3—C4	118.9 (2)	H7B—C7—H7C	109.00
C2—C3—C8	121.1 (2)	C3—C8—H8A	109.00
C4—C3—C8	119.9 (2)	C3—C8—H8B	109.00
C3—C4—C5	121.8 (2)	C3—C8—H8C	109.00
C4—C5—C6	119.6 (2)	H8A—C8—H8B	109.00
C1—C6—C5	120.2 (2)	H8A—C8—H8C	109.00
N1—C9—C10	121.6 (2)	H8B—C8—H8C	109.00
C9—C10—C11	119.8 (2)	N1—C9—H9	119.00
C9—C10—C15	121.1 (2)	C10—C9—H9	119.00
C11—C10—C15	119.1 (2)	C10—C11—H11	120.00
C10—C11—C12	120.7 (2)	C12—C11—H11	120.00
C11—C12—C13	118.7 (2)	C11—C12—H12	121.00
N2—C13—C12	118.7 (2)	C13—C12—H12	121.00
N2—C13—C14	118.9 (2)	C13—C14—H14	121.00
C12—C13—C14	122.4 (2)	C15—C14—H14	121.00
C13—C14—C15	118.6 (2)	C10—C15—H15	120.00
C10—C15—C14	120.6 (2)	C14—C15—H15	120.00
C3—C4—H4	119.00
C9—N1—C1—C2	−153.3 (2)	C2—C3—C4—C5	0.2 (4)
C9—N1—C1—C6	30.1 (4)	C8—C3—C4—C5	−179.1 (3)
C1—N1—C9—C10	−178.4 (2)	C3—C4—C5—C6	0.1 (4)
O1—N2—C13—C12	−9.2 (3)	C4—C5—C6—C1	−1.3 (4)
O1—N2—C13—C14	171.7 (2)	N1—C9—C10—C11	176.3 (2)
O2—N2—C13—C12	170.3 (3)	N1—C9—C10—C15	−5.4 (4)
O2—N2—C13—C14	−8.8 (3)	C9—C10—C11—C12	178.5 (2)
N1—C1—C2—C3	−178.7 (2)	C15—C10—C11—C12	0.1 (3)
N1—C1—C2—C7	2.6 (3)	C9—C10—C15—C14	−178.2 (2)
C6—C1—C2—C3	−2.0 (3)	C11—C10—C15—C14	0.2 (3)
C6—C1—C2—C7	179.3 (2)	C10—C11—C12—C13	−0.5 (4)
N1—C1—C6—C5	178.8 (2)	C11—C12—C13—N2	−178.3 (2)
C2—C1—C6—C5	2.3 (4)	C11—C12—C13—C14	0.8 (4)
C1—C2—C3—C4	0.8 (4)	N2—C13—C14—C15	178.6 (2)
C1—C2—C3—C8	−180.0 (3)	C12—C13—C14—C15	−0.5 (3)
C7—C2—C3—C4	179.4 (2)	C13—C14—C15—C10	0.0 (3)
C7—C2—C3—C8	−1.3 (4)