4-Meth­oxy-N-(3-phenyl­allyl­idene)aniline

In the mol­ecule of the title compound, C₁₆H₁₅NO, all bond lengths and angles are within normal ranges. The dihedral angle between the two aromatic rings is of 62.80 (1)°. The crystal packing is stabilized by C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.051
• wR factor = 0.152
• Data-to-parameter ratio = 15.5

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S1. Comment

Recently we have reported the structure of 4-methoxy-N-[3-(2-nitrophenyl)allylidene]aniline, (II) (Yang et al., 2006). As part of our ongoing studies on push-pull Schiff base compounds, the title compound, (I), was synthesized and its structure is presented here.

In the molecule of the title compound, all bond lengths and angles show normal values (Allen et al., 1987) and are comparable with those in (II). The whole molecule is non-planar, with a dihedral angle of 62.80 (1)° between the two aromatic rings, in contrast to that of 4.01 (1)° in (II). The crystal strucure is stabilized by a C—H···π interaction (C15—H15A···cg: H15A···Cg 2.708 Å, C15···cg 3.485 Å, C15—H15A···cg 141.6°; symmetry operator: 1/2 - x, 1/2 + y, z, cg is the centroid of the ring C10 to C15).

Related literature

For related literature, see: Yang et al. (2006); Allen et al. (1987).

S2. Experimental

The title compound was prepared according to the literature method of Yang et al. (2006). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of five days.

S3. Refinement

All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, and with U_iso(H) = 1.2 U_eq(C) or 1.5 U_eq(C) for methyl H atoms.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures

	Fig. 1. The structure of the title compound showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. A packing diagram of the title compound, viewed down the c axis.

4-Methoxy-N-(3-phenylallylidene)aniline

Crystal data

C16H15NO	Dx = 1.213 Mg m^−3
Mr = 237.29	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4641 reflections
a = 7.2170 (9) Å	θ = 2.5–25.8°
b = 6.3101 (8) Å	µ = 0.08 mm^−1
c = 57.061 (7) Å	T = 293 K
V = 2598.6 (6) Å^3	Block, yellow
Z = 8	0.43 × 0.35 × 0.16 mm
F(000) = 1008

Data collection

Siemens SMART 1000 CCD area detector diffractometer	2545 independent reflections
Radiation source: fine-focus sealed tube	2180 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −7→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −7→6
Tmin = 0.968, Tmax = 0.988	l = −70→68
13125 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.152	w = 1/[σ^2(Fo^2) + (0.0685P)^2 + 1.0047P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2545 reflections	Δρmax = 0.17 e Å^−3
164 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (11)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C11	0.0834 (2)	0.1903 (3)	−0.15889 (3)	0.0406 (4)
H11A	0.1424	0.2640	−0.1469	0.049*
C13	0.0018 (2)	0.1614 (3)	−0.19944 (3)	0.0391 (4)
C14	−0.0944 (2)	−0.0240 (3)	−0.19445 (3)	0.0429 (4)
H14A	−0.1549	−0.0964	−0.2064	0.051*
C15	−0.1006 (2)	−0.1014 (3)	−0.17184 (3)	0.0421 (4)
H15A	−0.1650	−0.2259	−0.1687	0.051*
N1	−0.0165 (2)	−0.0590 (2)	−0.12986 (2)	0.0453 (4)
C5	−0.0877 (2)	−0.5033 (3)	−0.05198 (3)	0.0461 (4)
H5A	−0.1456	−0.3736	−0.0545	0.055*
C12	0.0924 (2)	0.2686 (3)	−0.18164 (3)	0.0417 (4)
H12A	0.1585	0.3917	−0.1849	0.050*
O1	−0.0046 (2)	0.2257 (2)	−0.22245 (2)	0.0548 (4)
C1	0.0695 (3)	−0.8103 (3)	−0.06647 (3)	0.0507 (5)
H1B	0.1167	−0.8889	−0.0789	0.061*
C8	−0.0343 (3)	−0.3294 (3)	−0.10091 (3)	0.0466 (4)
H8A	−0.0494	−0.2298	−0.0891	0.056*
C3	0.0120 (3)	−0.7744 (3)	−0.02546 (4)	0.0588 (6)
H3A	0.0222	−0.8262	−0.0103	0.071*
C4	−0.0749 (3)	−0.5832 (3)	−0.02956 (3)	0.0538 (5)
H4A	−0.1252	−0.5076	−0.0171	0.065*
C9	−0.0278 (3)	−0.2554 (3)	−0.12480 (3)	0.0458 (4)
H9A	−0.0319	−0.3540	−0.1369	0.055*
C2	0.0837 (3)	−0.8885 (3)	−0.04397 (4)	0.0580 (5)
H2A	0.1415	−1.0180	−0.0413	0.070*
C7	−0.0199 (3)	−0.5322 (3)	−0.09489 (3)	0.0471 (5)
H7A	−0.0125	−0.6304	−0.1070	0.057*
C6	−0.0146 (2)	−0.6149 (3)	−0.07092 (3)	0.0414 (4)
C10	−0.0111 (2)	0.0051 (3)	−0.15358 (3)	0.0376 (4)
C16	0.0889 (4)	0.4160 (4)	−0.22840 (4)	0.0744 (7)
H16A	0.0734	0.4439	−0.2448	0.112*
H16B	0.2183	0.4017	−0.2249	0.112*
H16C	0.0380	0.5313	−0.2195	0.112*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C11	0.0415 (9)	0.0397 (9)	0.0404 (9)	−0.0017 (7)	−0.0034 (7)	−0.0053 (7)
C13	0.0384 (9)	0.0430 (9)	0.0360 (8)	0.0034 (7)	0.0013 (6)	0.0003 (7)
C14	0.0428 (9)	0.0435 (9)	0.0424 (9)	−0.0045 (7)	−0.0051 (7)	−0.0058 (7)
C15	0.0406 (9)	0.0391 (9)	0.0467 (9)	−0.0059 (7)	0.0008 (7)	0.0006 (7)
N1	0.0535 (9)	0.0450 (8)	0.0374 (8)	−0.0018 (7)	0.0009 (6)	0.0007 (6)
C5	0.0493 (10)	0.0436 (10)	0.0454 (9)	0.0041 (8)	−0.0012 (8)	0.0023 (8)
C12	0.0431 (9)	0.0366 (9)	0.0453 (9)	−0.0059 (7)	0.0007 (7)	−0.0003 (7)
O1	0.0682 (9)	0.0590 (8)	0.0373 (7)	−0.0089 (7)	−0.0028 (6)	0.0052 (6)
C1	0.0504 (11)	0.0397 (10)	0.0618 (11)	0.0012 (8)	0.0061 (9)	0.0000 (8)
C8	0.0550 (11)	0.0466 (10)	0.0383 (9)	−0.0034 (8)	0.0010 (8)	−0.0004 (8)
C3	0.0630 (13)	0.0591 (12)	0.0543 (12)	−0.0064 (10)	−0.0098 (9)	0.0171 (10)
C4	0.0611 (12)	0.0581 (12)	0.0422 (9)	−0.0018 (10)	−0.0017 (8)	0.0006 (8)
C9	0.0494 (10)	0.0483 (10)	0.0398 (9)	−0.0001 (8)	0.0034 (7)	−0.0011 (8)
C2	0.0553 (12)	0.0423 (10)	0.0763 (14)	0.0025 (9)	−0.0055 (10)	0.0158 (9)
C7	0.0526 (11)	0.0466 (10)	0.0422 (9)	−0.0018 (8)	0.0039 (8)	−0.0038 (8)
C6	0.0407 (9)	0.0387 (9)	0.0447 (9)	−0.0031 (7)	−0.0005 (7)	0.0012 (7)
C10	0.0373 (9)	0.0386 (8)	0.0368 (8)	0.0040 (7)	0.0019 (6)	−0.0007 (7)
C16	0.0997 (19)	0.0715 (15)	0.0522 (12)	−0.0198 (14)	−0.0039 (12)	0.0215 (11)

Geometric parameters (Å, º)

C11—C10	1.386 (2)	C1—C2	1.379 (3)
C11—C12	1.390 (2)	C1—C6	1.397 (2)
C11—H11A	0.9300	C1—H1B	0.9300
C13—O1	1.3752 (19)	C8—C7	1.329 (3)
C13—C12	1.384 (2)	C8—C9	1.442 (2)
C13—C14	1.390 (2)	C8—H8A	0.9300
C14—C15	1.380 (2)	C3—C2	1.379 (3)
C14—H14A	0.9300	C3—C4	1.380 (3)
C15—C10	1.398 (2)	C3—H3A	0.9300
C15—H15A	0.9300	C4—H4A	0.9300
N1—C9	1.275 (2)	C9—H9A	0.9300
N1—C10	1.413 (2)	C2—H2A	0.9300
C5—C4	1.378 (2)	C7—C6	1.465 (2)
C5—C6	1.394 (2)	C7—H7A	0.9300
C5—H5A	0.9300	C16—H16A	0.9600
C12—H12A	0.9300	C16—H16B	0.9600
O1—C16	1.418 (3)	C16—H16C	0.9600
C10—C11—C12	121.79 (15)	C2—C3—H3A	120.1
C10—C11—H11A	119.1	C4—C3—H3A	120.1
C12—C11—H11A	119.1	C5—C4—C3	120.52 (19)
O1—C13—C12	124.90 (16)	C5—C4—H4A	119.7
O1—C13—C14	115.29 (15)	C3—C4—H4A	119.7
C12—C13—C14	119.79 (15)	N1—C9—C8	122.08 (17)
C15—C14—C13	120.35 (15)	N1—C9—H9A	119.0
C15—C14—H14A	119.8	C8—C9—H9A	119.0
C13—C14—H14A	119.8	C3—C2—C1	119.89 (18)
C14—C15—C10	120.78 (16)	C3—C2—H2A	120.1
C14—C15—H15A	119.6	C1—C2—H2A	120.1
C10—C15—H15A	119.6	C8—C7—C6	125.90 (17)
C9—N1—C10	119.80 (15)	C8—C7—H7A	117.0
C4—C5—C6	120.64 (17)	C6—C7—H7A	117.0
C4—C5—H5A	119.7	C5—C6—C1	117.99 (16)
C6—C5—H5A	119.7	C5—C6—C7	122.28 (16)
C13—C12—C11	119.29 (16)	C1—C6—C7	119.72 (16)
C13—C12—H12A	120.4	C11—C10—C15	118.00 (15)
C11—C12—H12A	120.4	C11—C10—N1	117.67 (14)
C13—O1—C16	117.53 (15)	C15—C10—N1	124.29 (15)
C2—C1—C6	121.14 (18)	O1—C16—H16A	109.5
C2—C1—H1B	119.4	O1—C16—H16B	109.5
C6—C1—H1B	119.4	H16A—C16—H16B	109.5
C7—C8—C9	123.60 (17)	O1—C16—H16C	109.5
C7—C8—H8A	118.2	H16A—C16—H16C	109.5
C9—C8—H8A	118.2	H16B—C16—H16C	109.5
C2—C3—C4	119.80 (18)
O1—C13—C14—C15	−178.76 (15)	C9—C8—C7—C6	176.14 (17)
C12—C13—C14—C15	0.2 (3)	C4—C5—C6—C1	0.7 (3)
C13—C14—C15—C10	0.2 (3)	C4—C5—C6—C7	−177.93 (17)
O1—C13—C12—C11	177.96 (16)	C2—C1—C6—C5	−1.4 (3)
C14—C13—C12—C11	−0.9 (2)	C2—C1—C6—C7	177.27 (18)
C10—C11—C12—C13	1.2 (3)	C8—C7—C6—C5	23.2 (3)
C12—C13—O1—C16	0.1 (3)	C8—C7—C6—C1	−155.4 (2)
C14—C13—O1—C16	179.01 (18)	C12—C11—C10—C15	−0.8 (2)
C6—C5—C4—C3	0.6 (3)	C12—C11—C10—N1	−178.40 (15)
C2—C3—C4—C5	−1.2 (3)	C14—C15—C10—C11	0.1 (2)
C10—N1—C9—C8	−179.82 (16)	C14—C15—C10—N1	177.50 (16)
C7—C8—C9—N1	−170.2 (2)	C9—N1—C10—C11	−150.54 (18)
C4—C3—C2—C1	0.5 (3)	C9—N1—C10—C15	32.0 (3)
C6—C1—C2—C3	0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···Cg^i	0.93	2.71	3.49	142

Symmetry code: (i) −x−1/2, y−1/2, z.