4-[(E)-(2-Methoxy-phen-yl)imino-meth-yl]-N,N-dimethyl-aniline.

In the title compound, C(16)H(18)N(2)O, the dihedral angle between the benzene rings is 38.5 (2)°. The crystal packing is stabilized by weak C-H⋯N and C-H⋯O inter-actions and aromatic π-π stacking [centroid-centroid separations = 3.620 (5) and 3.546 (4) Å].

Related literature

For general background to Schiff bases, see: Atwood & Harvey (2001 ▶). For a related structure, see: Liu et al. (2009 ▶).

Experimental

Crystal data

C16H18N2O

M = 254.32

Orthorhombic,

a = 15.182 (8) Å

b = 11.756 (6) Å

c = 7.809 (4) Å

V = 1393.8 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.60 × 0.58 × 0.49 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.956, T max = 0.963

6900 measured reflections

2335 independent reflections

1554 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.01

2335 reflections

172 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810017228/hb5420sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017228/hb5420Isup2.hkl

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

C16H18N2O	F(000) = 544
Mr = 254.32	Dx = 1.212 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1616 reflections
a = 15.182 (8) Å	θ = 2.7–21.5°
b = 11.756 (6) Å	µ = 0.08 mm−1
c = 7.809 (4) Å	T = 298 K
V = 1393.8 (13) Å3	Block, yellow
Z = 4	0.60 × 0.58 × 0.49 mm

Siemens SMART CCD diffractometer	2335 independent reflections
Radiation source: fine-focus sealed tube	1554 reflections with I > 2σ(I)
graphite	Rint = 0.055
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −17→18
Tmin = 0.956, Tmax = 0.963	k = −13→11
6900 measured reflections	l = −9→9

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0524P)2 + 0.2535P] where P = (Fo2 + 2Fc2)/3
2335 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.17 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.08529 (16)	0.7420 (2)	1.1920 (4)	0.0457 (6)
N2	0.1439 (2)	1.0507 (2)	0.5158 (4)	0.0597 (8)
O1	−0.04554 (14)	0.71462 (18)	1.4179 (3)	0.0612 (6)
C1	0.10910 (19)	0.7230 (3)	1.0385 (5)	0.0483 (8)
H1	0.1249	0.6490	1.0095	0.058*
C2	0.11330 (18)	0.8091 (2)	0.9052 (4)	0.0441 (7)
C3	0.0861 (2)	0.9208 (2)	0.9266 (5)	0.0498 (8)
H3	0.0622	0.9424	1.0313	0.060*
C4	0.0930 (2)	1.0008 (3)	0.7990 (4)	0.0488 (8)
H4	0.0721	1.0742	0.8172	0.059*
C5	0.1316 (2)	0.9720 (3)	0.6405 (4)	0.0441 (8)
C6	0.1559 (2)	0.8582 (3)	0.6161 (4)	0.0486 (8)
H6	0.1789	0.8354	0.5112	0.058*
C7	0.1464 (2)	0.7804 (3)	0.7451 (4)	0.0490 (9)
H7	0.1628	0.7053	0.7247	0.059*
C8	0.1310 (2)	1.1711 (3)	0.5473 (6)	0.0668 (10)
H8A	0.1425	1.2130	0.4441	0.100*
H8B	0.1706	1.1959	0.6356	0.100*
H8C	0.0714	1.1843	0.5832	0.100*
C9	0.1775 (3)	1.0189 (3)	0.3522 (5)	0.0838 (13)
H9A	0.1816	1.0850	0.2805	0.126*
H9B	0.1386	0.9645	0.3003	0.126*
H9C	0.2349	0.9858	0.3656	0.126*
C10	0.09047 (19)	0.6513 (2)	1.3124 (4)	0.0419 (7)
C11	0.0228 (2)	0.6391 (2)	1.4323 (4)	0.0455 (7)
C12	0.0272 (2)	0.5535 (2)	1.5526 (5)	0.0535 (8)
H12	−0.0182	0.5450	1.6315	0.064*
C13	0.0982 (2)	0.4804 (3)	1.5570 (5)	0.0613 (9)
H13	0.1005	0.4228	1.6385	0.074*
C14	0.1645 (2)	0.4925 (3)	1.4428 (5)	0.0600 (9)
H14	0.2124	0.4433	1.4462	0.072*
C15	0.1615 (2)	0.5780 (2)	1.3207 (5)	0.0522 (8)
H15	0.2077	0.5861	1.2435	0.063*
C16	−0.1075 (3)	0.7158 (4)	1.5491 (7)	0.1119 (18)
H16A	−0.1517	0.7718	1.5246	0.168*
H16B	−0.0789	0.7341	1.6553	0.168*
H16C	−0.1345	0.6422	1.5578	0.168*

	U11	U22	U33	U12	U13	U23
N1	0.0510 (15)	0.0398 (15)	0.0465 (16)	−0.0020 (12)	0.0057 (14)	0.0021 (13)
N2	0.082 (2)	0.0495 (17)	0.0477 (19)	0.0023 (15)	0.0034 (16)	0.0051 (14)
O1	0.0611 (14)	0.0659 (14)	0.0565 (14)	0.0128 (11)	0.0183 (14)	0.0079 (13)
C1	0.0491 (18)	0.0401 (17)	0.056 (2)	−0.0014 (13)	0.0061 (17)	−0.0022 (18)
C2	0.0444 (16)	0.0412 (17)	0.047 (2)	−0.0059 (14)	0.0060 (16)	0.0013 (16)
C3	0.0525 (18)	0.0463 (17)	0.0506 (19)	0.0001 (14)	0.0084 (18)	−0.0012 (18)
C4	0.0532 (19)	0.0412 (17)	0.052 (2)	0.0033 (15)	−0.0015 (18)	−0.0010 (17)
C5	0.0472 (18)	0.0457 (18)	0.0393 (19)	−0.0050 (14)	−0.0056 (15)	0.0044 (16)
C6	0.0574 (19)	0.051 (2)	0.0379 (18)	−0.0011 (15)	0.0008 (15)	−0.0072 (16)
C7	0.057 (2)	0.0390 (18)	0.051 (2)	−0.0002 (15)	−0.0008 (16)	−0.0017 (16)
C8	0.072 (2)	0.051 (2)	0.077 (2)	0.0034 (17)	−0.005 (2)	0.0163 (19)
C9	0.123 (4)	0.070 (3)	0.058 (3)	−0.007 (2)	0.006 (3)	0.011 (2)
C10	0.0513 (18)	0.0315 (15)	0.0430 (18)	−0.0035 (14)	0.0018 (16)	−0.0028 (15)
C11	0.0547 (18)	0.0434 (17)	0.0383 (17)	−0.0013 (14)	0.0023 (17)	−0.0032 (16)
C12	0.061 (2)	0.0488 (19)	0.050 (2)	−0.0071 (16)	0.0132 (18)	0.0029 (17)
C13	0.076 (2)	0.0470 (19)	0.061 (2)	0.0001 (18)	−0.004 (2)	0.0091 (19)
C14	0.057 (2)	0.0491 (19)	0.074 (3)	0.0080 (15)	0.004 (2)	0.011 (2)
C15	0.0488 (18)	0.0497 (19)	0.058 (2)	−0.0004 (15)	0.0052 (17)	0.0025 (18)
C16	0.108 (3)	0.122 (4)	0.106 (4)	0.047 (3)	0.061 (3)	0.035 (3)

N1—C1	1.272 (4)	C8—H8A	0.9600
N1—C10	1.423 (4)	C8—H8B	0.9600
N2—C5	1.356 (4)	C8—H8C	0.9600
N2—C9	1.425 (5)	C9—H9A	0.9600
N2—C8	1.450 (4)	C9—H9B	0.9600
O1—C11	1.370 (3)	C9—H9C	0.9600
O1—C16	1.390 (5)	C10—C15	1.382 (4)
C1—C2	1.453 (5)	C10—C11	1.398 (4)
C1—H1	0.9300	C11—C12	1.378 (4)
C2—C3	1.387 (4)	C12—C13	1.379 (4)
C2—C7	1.390 (4)	C12—H12	0.9300
C3—C4	1.374 (4)	C13—C14	1.353 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.410 (4)	C14—C15	1.386 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.401 (4)	C15—H15	0.9300
C6—C7	1.368 (4)	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—H7	0.9300	C16—H16C	0.9600
C1—N1—C10	118.4 (3)	H8B—C8—H8C	109.5
C5—N2—C9	120.9 (3)	N2—C9—H9A	109.5
C5—N2—C8	121.7 (3)	N2—C9—H9B	109.5
C9—N2—C8	117.2 (3)	H9A—C9—H9B	109.5
C11—O1—C16	117.3 (3)	N2—C9—H9C	109.5
N1—C1—C2	124.4 (3)	H9A—C9—H9C	109.5
N1—C1—H1	117.8	H9B—C9—H9C	109.5
C2—C1—H1	117.8	C15—C10—C11	118.6 (3)
C3—C2—C7	116.5 (3)	C15—C10—N1	122.8 (3)
C3—C2—C1	124.1 (3)	C11—C10—N1	118.6 (3)
C7—C2—C1	119.4 (3)	O1—C11—C12	124.4 (3)
C4—C3—C2	122.5 (3)	O1—C11—C10	115.8 (3)
C4—C3—H3	118.7	C12—C11—C10	119.7 (3)
C2—C3—H3	118.7	C11—C12—C13	120.7 (3)
C3—C4—C5	120.3 (3)	C11—C12—H12	119.7
C3—C4—H4	119.9	C13—C12—H12	119.7
C5—C4—H4	119.9	C14—C13—C12	120.0 (3)
N2—C5—C6	121.2 (3)	C14—C13—H13	120.0
N2—C5—C4	121.6 (3)	C12—C13—H13	120.0
C6—C5—C4	117.3 (3)	C13—C14—C15	120.3 (3)
C7—C6—C5	120.7 (3)	C13—C14—H14	119.8
C7—C6—H6	119.6	C15—C14—H14	119.8
C5—C6—H6	119.6	C10—C15—C14	120.7 (3)
C6—C7—C2	122.6 (3)	C10—C15—H15	119.6
C6—C7—H7	118.7	C14—C15—H15	119.6
C2—C7—H7	118.7	O1—C16—H16A	109.5
N2—C8—H8A	109.5	O1—C16—H16B	109.5
N2—C8—H8B	109.5	H16A—C16—H16B	109.5
H8A—C8—H8B	109.5	O1—C16—H16C	109.5
N2—C8—H8C	109.5	H16A—C16—H16C	109.5
H8A—C8—H8C	109.5	H16B—C16—H16C	109.5
C10—N1—C1—C2	−175.4 (3)	C1—C2—C7—C6	−177.0 (3)
N1—C1—C2—C3	−4.6 (5)	C1—N1—C10—C15	42.7 (4)
N1—C1—C2—C7	175.3 (3)	C1—N1—C10—C11	−140.4 (3)
C7—C2—C3—C4	−1.6 (5)	C16—O1—C11—C12	10.2 (5)
C1—C2—C3—C4	178.4 (3)	C16—O1—C11—C10	−170.9 (4)
C2—C3—C4—C5	−2.1 (5)	C15—C10—C11—O1	179.7 (3)
C9—N2—C5—C6	3.6 (5)	N1—C10—C11—O1	2.5 (4)
C8—N2—C5—C6	−170.9 (3)	C15—C10—C11—C12	−1.5 (4)
C9—N2—C5—C4	−175.8 (3)	N1—C10—C11—C12	−178.6 (3)
C8—N2—C5—C4	9.8 (5)	O1—C11—C12—C13	179.4 (3)
C3—C4—C5—N2	−176.2 (3)	C10—C11—C12—C13	0.7 (5)
C3—C4—C5—C6	4.5 (4)	C11—C12—C13—C14	0.2 (5)
N2—C5—C6—C7	177.4 (3)	C12—C13—C14—C15	−0.1 (5)
C4—C5—C6—C7	−3.2 (4)	C11—C10—C15—C14	1.5 (4)
C5—C6—C7—C2	−0.5 (5)	N1—C10—C15—C14	178.5 (3)
C3—C2—C7—C6	2.9 (5)	C13—C14—C15—C10	−0.7 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···N1i	0.96	2.67	3.620 (5)	170
C4—H4···O1i	0.93	2.64	3.546 (4)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8C⋯N1i	0.96	2.67	3.620 (5)	170
C4—H4⋯O1i	0.93	2.64	3.546 (4)	166

Symmetry code: (i) .