N-(2,3-Dimeth-oxy-benzyl-idene)naphthalen-1-amine.

The title compound, C(19)H(17)NO(2), represents a trans isomer with respect to the C=N bond. The dihedral angle between the planes of the naphthyl ring system and the benzene ring is 71.70 (3)°. In the crystal, weak C-H⋯O hydrogen bonding is present.

Related literature

For properties of Schiff bases, see: Chen et al. (2008 ▶); May et al. (2004 ▶); Weber et al. (2007 ▶). For related structures, see: Tariq et al. (2010 ▶); Zhu et al. (2010 ▶).

Experimental

Crystal data

C19H17NO2

M = 291.34

Orthorhombic,

a = 7.7163 (7) Å

b = 17.0786 (16) Å

c = 23.427 (2) Å

V = 3087.3 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.48 × 0.45 × 0.36 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.962, T max = 0.971

14855 measured reflections

2721 independent reflections

1452 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.187

S = 1.12

2721 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000079/pv2375sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000079/pv2375Isup2.hkl

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

C19H17NO2	F(000) = 1232
Mr = 291.34	Dx = 1.254 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2315 reflections
a = 7.7163 (7) Å	θ = 2.4–24.2°
b = 17.0786 (16) Å	µ = 0.08 mm−1
c = 23.427 (2) Å	T = 298 K
V = 3087.3 (5) Å3	Block, colorless
Z = 8	0.48 × 0.45 × 0.36 mm

Bruker SMART CCD area-detector diffractometer	2721 independent reflections
Radiation source: fine-focus sealed tube	1452 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→9
Tmin = 0.962, Tmax = 0.971	k = −20→10
14855 measured reflections	l = −27→27

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.187	w = 1/[σ2(Fo2) + (0.0462P)2 + 2.0418P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2721 reflections	Δρmax = 0.18 e Å−3
202 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0059 (11)

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	0.3928 (4)	0.08249 (16)	0.55054 (11)	0.0578 (8)
O1	0.4329 (3)	0.18230 (12)	0.70513 (9)	0.0535 (6)
O2	0.4198 (3)	0.10066 (14)	0.80315 (9)	0.0682 (7)
C1	0.4312 (4)	0.11133 (19)	0.59845 (13)	0.0508 (8)
H1	0.4599	0.1641	0.6006	0.061*
C2	0.4323 (4)	0.06453 (19)	0.65073 (13)	0.0492 (8)
C3	0.4280 (4)	0.10162 (18)	0.70328 (13)	0.0471 (8)
C4	0.4265 (4)	0.05837 (19)	0.75393 (14)	0.0523 (8)
C5	0.4328 (5)	−0.0221 (2)	0.75084 (16)	0.0660 (10)
H5	0.4311	−0.0517	0.7842	0.079*
C6	0.4417 (5)	−0.0591 (2)	0.69855 (17)	0.0714 (11)
H6	0.4489	−0.1134	0.6971	0.086*
C7	0.4402 (4)	−0.0173 (2)	0.64880 (16)	0.0624 (10)
H7	0.4443	−0.0430	0.6139	0.075*
C8	0.2786 (5)	0.2204 (2)	0.72204 (17)	0.0784 (12)
H8A	0.1901	0.2114	0.6940	0.118*
H8B	0.2996	0.2756	0.7254	0.118*
H8C	0.2414	0.2001	0.7582	0.118*
C9	0.4279 (6)	0.0592 (2)	0.85555 (14)	0.0817 (13)
H9A	0.3322	0.0235	0.8579	0.122*
H9B	0.4222	0.0956	0.8867	0.122*
H9C	0.5347	0.0306	0.8575	0.122*
C10	0.4014 (4)	0.13165 (18)	0.50188 (13)	0.0522 (8)
C11	0.5459 (5)	0.1750 (2)	0.48899 (15)	0.0650 (10)
H11	0.6406	0.1746	0.5136	0.078*
C12	0.5514 (5)	0.2198 (2)	0.43916 (16)	0.0720 (11)
H12	0.6505	0.2486	0.4308	0.086*
C13	0.4152 (5)	0.2221 (2)	0.40291 (15)	0.0657 (10)
H13	0.4217	0.2522	0.3699	0.079*
C14	0.2641 (5)	0.17926 (18)	0.41459 (13)	0.0519 (8)
C15	0.2558 (4)	0.13319 (17)	0.46482 (12)	0.0478 (8)
C16	0.1014 (5)	0.09268 (19)	0.47708 (14)	0.0556 (9)
H16	0.0948	0.0620	0.5098	0.067*
C17	−0.0383 (5)	0.0976 (2)	0.44183 (15)	0.0644 (10)
H17	−0.1399	0.0711	0.4509	0.077*
C18	−0.0290 (5)	0.1425 (2)	0.39210 (16)	0.0697 (11)
H18	−0.1246	0.1454	0.3680	0.084*
C19	0.1173 (5)	0.1817 (2)	0.37866 (15)	0.0636 (10)
H19	0.1215	0.2108	0.3451	0.076*

	U11	U22	U33	U12	U13	U23
N1	0.0671 (19)	0.0592 (17)	0.0471 (16)	−0.0026 (15)	−0.0064 (14)	−0.0001 (14)
O1	0.0566 (14)	0.0493 (13)	0.0546 (13)	−0.0039 (11)	0.0012 (11)	0.0036 (10)
O2	0.0968 (19)	0.0635 (15)	0.0443 (13)	−0.0053 (14)	−0.0050 (12)	0.0108 (12)
C1	0.051 (2)	0.0505 (19)	0.051 (2)	−0.0018 (16)	−0.0015 (16)	−0.0015 (16)
C2	0.0459 (19)	0.0527 (19)	0.0490 (19)	−0.0018 (15)	−0.0078 (15)	0.0007 (16)
C3	0.0377 (17)	0.0510 (19)	0.0526 (19)	−0.0033 (15)	−0.0039 (14)	0.0078 (16)
C4	0.050 (2)	0.055 (2)	0.051 (2)	−0.0034 (16)	−0.0060 (16)	0.0079 (17)
C5	0.077 (3)	0.058 (2)	0.063 (2)	−0.005 (2)	−0.009 (2)	0.016 (2)
C6	0.086 (3)	0.048 (2)	0.081 (3)	0.0014 (19)	−0.014 (2)	0.006 (2)
C7	0.065 (2)	0.058 (2)	0.064 (2)	0.0025 (18)	−0.0112 (18)	−0.0026 (19)
C8	0.077 (3)	0.070 (3)	0.088 (3)	0.015 (2)	0.017 (2)	0.006 (2)
C9	0.106 (3)	0.088 (3)	0.051 (2)	−0.010 (2)	−0.007 (2)	0.022 (2)
C10	0.062 (2)	0.0515 (19)	0.0428 (18)	−0.0016 (17)	0.0023 (16)	−0.0055 (15)
C11	0.064 (2)	0.076 (2)	0.055 (2)	−0.008 (2)	0.0008 (18)	−0.013 (2)
C12	0.079 (3)	0.074 (3)	0.063 (2)	−0.020 (2)	0.020 (2)	−0.008 (2)
C13	0.091 (3)	0.057 (2)	0.049 (2)	−0.004 (2)	0.014 (2)	0.0008 (17)
C14	0.070 (2)	0.0433 (18)	0.0427 (18)	0.0072 (18)	0.0079 (17)	−0.0064 (15)
C15	0.061 (2)	0.0412 (17)	0.0411 (17)	0.0046 (16)	0.0028 (16)	−0.0054 (14)
C16	0.067 (2)	0.0498 (19)	0.0502 (19)	−0.0001 (18)	−0.0005 (17)	0.0017 (16)
C17	0.065 (2)	0.061 (2)	0.067 (2)	−0.0013 (19)	−0.0048 (19)	0.0021 (19)
C18	0.076 (3)	0.065 (2)	0.068 (3)	0.015 (2)	−0.015 (2)	0.000 (2)
C19	0.088 (3)	0.054 (2)	0.049 (2)	0.016 (2)	−0.004 (2)	0.0052 (17)

N1—C1	1.261 (4)	C9—H9B	0.9600
N1—C10	1.418 (4)	C9—H9C	0.9600
O1—C3	1.379 (4)	C10—C11	1.372 (5)
O1—C8	1.413 (4)	C10—C15	1.420 (4)
O2—C4	1.362 (4)	C11—C12	1.396 (5)
O2—C9	1.418 (4)	C11—H11	0.9300
C1—C2	1.462 (4)	C12—C13	1.352 (5)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.385 (4)	C13—C14	1.403 (5)
C2—C7	1.399 (4)	C13—H13	0.9300
C3—C4	1.398 (4)	C14—C19	1.412 (5)
C4—C5	1.378 (5)	C14—C15	1.417 (4)
C5—C6	1.380 (5)	C15—C16	1.407 (4)
C5—H5	0.9300	C16—C17	1.360 (5)
C6—C7	1.367 (5)	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.396 (5)
C7—H7	0.9300	C17—H17	0.9300
C8—H8A	0.9600	C18—C19	1.350 (5)
C8—H8B	0.9600	C18—H18	0.9300
C8—H8C	0.9600	C19—H19	0.9300
C9—H9A	0.9600
C1—N1—C10	118.3 (3)	O2—C9—H9C	109.5
C3—O1—C8	116.5 (3)	H9A—C9—H9C	109.5
C4—O2—C9	117.8 (3)	H9B—C9—H9C	109.5
N1—C1—C2	122.2 (3)	C11—C10—N1	122.3 (3)
N1—C1—H1	118.9	C11—C10—C15	119.9 (3)
C2—C1—H1	118.9	N1—C10—C15	117.7 (3)
C3—C2—C7	119.1 (3)	C10—C11—C12	120.3 (3)
C3—C2—C1	119.6 (3)	C10—C11—H11	119.8
C7—C2—C1	121.3 (3)	C12—C11—H11	119.8
O1—C3—C2	119.0 (3)	C13—C12—C11	121.1 (4)
O1—C3—C4	120.1 (3)	C13—C12—H12	119.4
C2—C3—C4	120.9 (3)	C11—C12—H12	119.4
O2—C4—C5	125.1 (3)	C12—C13—C14	120.6 (3)
O2—C4—C3	116.0 (3)	C12—C13—H13	119.7
C5—C4—C3	118.9 (3)	C14—C13—H13	119.7
C4—C5—C6	120.3 (3)	C13—C14—C19	122.4 (3)
C4—C5—H5	119.8	C13—C14—C15	119.3 (3)
C6—C5—H5	119.8	C19—C14—C15	118.3 (3)
C7—C6—C5	121.2 (3)	C16—C15—C14	118.7 (3)
C7—C6—H6	119.4	C16—C15—C10	122.4 (3)
C5—C6—H6	119.4	C14—C15—C10	118.8 (3)
C6—C7—C2	119.6 (3)	C17—C16—C15	121.1 (3)
C6—C7—H7	120.2	C17—C16—H16	119.5
C2—C7—H7	120.2	C15—C16—H16	119.5
O1—C8—H8A	109.5	C16—C17—C18	120.0 (4)
O1—C8—H8B	109.5	C16—C17—H17	120.0
H8A—C8—H8B	109.5	C18—C17—H17	120.0
O1—C8—H8C	109.5	C19—C18—C17	120.6 (4)
H8A—C8—H8C	109.5	C19—C18—H18	119.7
H8B—C8—H8C	109.5	C17—C18—H18	119.7
O2—C9—H9A	109.5	C18—C19—C14	121.2 (3)
O2—C9—H9B	109.5	C18—C19—H19	119.4
H9A—C9—H9B	109.5	C14—C19—H19	119.4
C10—N1—C1—C2	−177.7 (3)	C1—N1—C10—C15	−130.1 (3)
N1—C1—C2—C3	−162.3 (3)	N1—C10—C11—C12	177.0 (3)
N1—C1—C2—C7	18.7 (5)	C15—C10—C11—C12	−0.9 (5)
C8—O1—C3—C2	109.7 (3)	C10—C11—C12—C13	0.5 (6)
C8—O1—C3—C4	−73.1 (4)	C11—C12—C13—C14	0.1 (6)
C7—C2—C3—O1	175.4 (3)	C12—C13—C14—C19	178.3 (3)
C1—C2—C3—O1	−3.7 (4)	C12—C13—C14—C15	−0.3 (5)
C7—C2—C3—C4	−1.8 (5)	C13—C14—C15—C16	177.8 (3)
C1—C2—C3—C4	179.1 (3)	C19—C14—C15—C16	−0.7 (4)
C9—O2—C4—C5	3.0 (5)	C13—C14—C15—C10	−0.1 (4)
C9—O2—C4—C3	−176.6 (3)	C19—C14—C15—C10	−178.7 (3)
O1—C3—C4—O2	3.7 (4)	C11—C10—C15—C16	−177.2 (3)
C2—C3—C4—O2	−179.2 (3)	N1—C10—C15—C16	4.8 (4)
O1—C3—C4—C5	−175.9 (3)	C11—C10—C15—C14	0.7 (4)
C2—C3—C4—C5	1.2 (5)	N1—C10—C15—C14	−177.3 (3)
O2—C4—C5—C6	−179.1 (3)	C14—C15—C16—C17	−0.4 (5)
C3—C4—C5—C6	0.5 (5)	C10—C15—C16—C17	177.5 (3)
C4—C5—C6—C7	−1.6 (6)	C15—C16—C17—C18	1.0 (5)
C5—C6—C7—C2	1.1 (6)	C16—C17—C18—C19	−0.4 (5)
C3—C2—C7—C6	0.6 (5)	C17—C18—C19—C14	−0.7 (5)
C1—C2—C7—C6	179.7 (3)	C13—C14—C19—C18	−177.2 (3)
C1—N1—C10—C11	51.9 (4)	C15—C14—C19—C18	1.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8C···O1i	0.96	2.54	3.232 (4)	129
C8—H8C···O2	0.96	2.43	2.998 (4)	118
C16—H16···N1	0.93	2.52	2.839 (4)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8C⋯O1i	0.96	2.54	3.232 (4)	129

Symmetry code: (i) .