organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

N-(2,3-Dimeth­­oxy­benzyl­­idene)naphthalen-1-amine

aDepartment of Traditional Chinese Pharmacology, Shanxi University of Traditional Chinese Medicine, Taiyuan 030024, People's Republic of China
*Correspondence e-mail: ailingguo@126.com

(Received 26 December 2010; accepted 4 January 2011; online 8 January 2011)

The title compound, C19H17NO2, 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[Chen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170-2171.]); May et al. (2004[May, J. P., Ting, R., Lermer, L., Thomas, J. M., Roupioz, Y. & Perrin, D. M. (2004). J. Am. Chem. Soc. 126, 4145-4156.]); Weber et al. (2007[Weber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159-1162.]). For related structures, see: Tariq et al. (2010[Tariq, M. I., Ahmad, S., Tahir, M. N., Sarfaraz, M. & Hussain, I. (2010). Acta Cryst. E66, o1561.]); Zhu et al. (2010[Zhu, R., Zhang, Y. & Ren, Y. (2010). Acta Cryst. E66, o2337.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17NO2

  • Mr = 291.34

  • Orthorhombic, P b c a

  • 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[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.962, Tmax = 0.971

  • 14855 measured reflections

  • 2721 independent reflections

  • 1452 reflections with I > 2σ(I)

  • Rint = 0.057

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8C⋯O1i 0.96 2.54 3.232 (4) 129
Symmetry code: (i) [x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The Schiff bases have received considerable attention for many years, primarily due to their importance as ligands in metal complexes with special magnetic (Weber et al., 2007), catalytic (Chen et al., 2008) and biological properties (May et al., 2004). Here, we report the crystal structure of the title compound.

The title molecule (Fig. 1) represents a trans-isomer with respect to the C11N1 bond. The planes of the aromatic systems of the the naphthyl and benzene groups, C10—C19 and C2—C7, respectively, form dihedral angle of 71.70 (3)°. The bond distances and bond angles in the title compound are in agreement with the corresponding bond distances and angles reported in the crystale structures of closely related compounds, (Tariq et al., 2010; Zhu et al., 2010). The crystal structure of the title compound displays weak intermolecular interactions C8—H8C···O1 as well as intramolecular hydrogen bonds, C8—H8C···O2 and C16—H16···N1.

Related literature top

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 top

1-Naphthylamine (0.72 g, 5 mmol) and 2,3-dimethoxybenzaldehyde (0.83 g, 5 mmol) were dissolved in ethanol (20 ml). The mixture was refluxed for 2 h, and then cooled to room temperature. The reaction mixture was filtered and the filtered cake was recreystallized from ethyl alcohol (yield 80%). Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Refinement top

H atoms were placed in idealized positions and allowed to ride on their respective parent atoms, with C—H = 0.93–0.96 Å and Uiso(H) = 1.2 or 1.5 times Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound; displacement ellipsoids are drawn at the 30% probability level.
N-(2,3-Dimethoxybenzylidene)naphthalen-1-amine top
Crystal data top
C19H17NO2F(000) = 1232
Mr = 291.34Dx = 1.254 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2315 reflections
a = 7.7163 (7) Åθ = 2.4–24.2°
b = 17.0786 (16) ŵ = 0.08 mm1
c = 23.427 (2) ÅT = 298 K
V = 3087.3 (5) Å3Block, colorless
Z = 80.48 × 0.45 × 0.36 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2721 independent reflections
Radiation source: fine-focus sealed tube1452 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ϕ and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
h = 89
Tmin = 0.962, Tmax = 0.971k = 2010
14855 measured reflectionsl = 2727
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-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 reflectionsΔρmax = 0.18 e Å3
202 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0059 (11)
Crystal data top
C19H17NO2V = 3087.3 (5) Å3
Mr = 291.34Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 7.7163 (7) ŵ = 0.08 mm1
b = 17.0786 (16) ÅT = 298 K
c = 23.427 (2) Å0.48 × 0.45 × 0.36 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2721 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)
1452 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.971Rint = 0.057
14855 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.187H-atom parameters constrained
S = 1.12Δρmax = 0.18 e Å3
2721 reflectionsΔρmin = 0.15 e Å3
202 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.3928 (4)0.08249 (16)0.55054 (11)0.0578 (8)
O10.4329 (3)0.18230 (12)0.70513 (9)0.0535 (6)
O20.4198 (3)0.10066 (14)0.80315 (9)0.0682 (7)
C10.4312 (4)0.11133 (19)0.59845 (13)0.0508 (8)
H10.45990.16410.60060.061*
C20.4323 (4)0.06453 (19)0.65073 (13)0.0492 (8)
C30.4280 (4)0.10162 (18)0.70328 (13)0.0471 (8)
C40.4265 (4)0.05837 (19)0.75393 (14)0.0523 (8)
C50.4328 (5)0.0221 (2)0.75084 (16)0.0660 (10)
H50.43110.05170.78420.079*
C60.4417 (5)0.0591 (2)0.69855 (17)0.0714 (11)
H60.44890.11340.69710.086*
C70.4402 (4)0.0173 (2)0.64880 (16)0.0624 (10)
H70.44430.04300.61390.075*
C80.2786 (5)0.2204 (2)0.72204 (17)0.0784 (12)
H8A0.19010.21140.69400.118*
H8B0.29960.27560.72540.118*
H8C0.24140.20010.75820.118*
C90.4279 (6)0.0592 (2)0.85555 (14)0.0817 (13)
H9A0.33220.02350.85790.122*
H9B0.42220.09560.88670.122*
H9C0.53470.03060.85750.122*
C100.4014 (4)0.13165 (18)0.50188 (13)0.0522 (8)
C110.5459 (5)0.1750 (2)0.48899 (15)0.0650 (10)
H110.64060.17460.51360.078*
C120.5514 (5)0.2198 (2)0.43916 (16)0.0720 (11)
H120.65050.24860.43080.086*
C130.4152 (5)0.2221 (2)0.40291 (15)0.0657 (10)
H130.42170.25220.36990.079*
C140.2641 (5)0.17926 (18)0.41459 (13)0.0519 (8)
C150.2558 (4)0.13319 (17)0.46482 (12)0.0478 (8)
C160.1014 (5)0.09268 (19)0.47708 (14)0.0556 (9)
H160.09480.06200.50980.067*
C170.0383 (5)0.0976 (2)0.44183 (15)0.0644 (10)
H170.13990.07110.45090.077*
C180.0290 (5)0.1425 (2)0.39210 (16)0.0697 (11)
H180.12460.14540.36800.084*
C190.1173 (5)0.1817 (2)0.37866 (15)0.0636 (10)
H190.12150.21080.34510.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0671 (19)0.0592 (17)0.0471 (16)0.0026 (15)0.0064 (14)0.0001 (14)
O10.0566 (14)0.0493 (13)0.0546 (13)0.0039 (11)0.0012 (11)0.0036 (10)
O20.0968 (19)0.0635 (15)0.0443 (13)0.0053 (14)0.0050 (12)0.0108 (12)
C10.051 (2)0.0505 (19)0.051 (2)0.0018 (16)0.0015 (16)0.0015 (16)
C20.0459 (19)0.0527 (19)0.0490 (19)0.0018 (15)0.0078 (15)0.0007 (16)
C30.0377 (17)0.0510 (19)0.0526 (19)0.0033 (15)0.0039 (14)0.0078 (16)
C40.050 (2)0.055 (2)0.051 (2)0.0034 (16)0.0060 (16)0.0079 (17)
C50.077 (3)0.058 (2)0.063 (2)0.005 (2)0.009 (2)0.016 (2)
C60.086 (3)0.048 (2)0.081 (3)0.0014 (19)0.014 (2)0.006 (2)
C70.065 (2)0.058 (2)0.064 (2)0.0025 (18)0.0112 (18)0.0026 (19)
C80.077 (3)0.070 (3)0.088 (3)0.015 (2)0.017 (2)0.006 (2)
C90.106 (3)0.088 (3)0.051 (2)0.010 (2)0.007 (2)0.022 (2)
C100.062 (2)0.0515 (19)0.0428 (18)0.0016 (17)0.0023 (16)0.0055 (15)
C110.064 (2)0.076 (2)0.055 (2)0.008 (2)0.0008 (18)0.013 (2)
C120.079 (3)0.074 (3)0.063 (2)0.020 (2)0.020 (2)0.008 (2)
C130.091 (3)0.057 (2)0.049 (2)0.004 (2)0.014 (2)0.0008 (17)
C140.070 (2)0.0433 (18)0.0427 (18)0.0072 (18)0.0079 (17)0.0064 (15)
C150.061 (2)0.0412 (17)0.0411 (17)0.0046 (16)0.0028 (16)0.0054 (14)
C160.067 (2)0.0498 (19)0.0502 (19)0.0001 (18)0.0005 (17)0.0017 (16)
C170.065 (2)0.061 (2)0.067 (2)0.0013 (19)0.0048 (19)0.0021 (19)
C180.076 (3)0.065 (2)0.068 (3)0.015 (2)0.015 (2)0.000 (2)
C190.088 (3)0.054 (2)0.049 (2)0.016 (2)0.004 (2)0.0052 (17)
Geometric parameters (Å, º) top
N1—C11.261 (4)C9—H9B0.9600
N1—C101.418 (4)C9—H9C0.9600
O1—C31.379 (4)C10—C111.372 (5)
O1—C81.413 (4)C10—C151.420 (4)
O2—C41.362 (4)C11—C121.396 (5)
O2—C91.418 (4)C11—H110.9300
C1—C21.462 (4)C12—C131.352 (5)
C1—H10.9300C12—H120.9300
C2—C31.385 (4)C13—C141.403 (5)
C2—C71.399 (4)C13—H130.9300
C3—C41.398 (4)C14—C191.412 (5)
C4—C51.378 (5)C14—C151.417 (4)
C5—C61.380 (5)C15—C161.407 (4)
C5—H50.9300C16—C171.360 (5)
C6—C71.367 (5)C16—H160.9300
C6—H60.9300C17—C181.396 (5)
C7—H70.9300C17—H170.9300
C8—H8A0.9600C18—C191.350 (5)
C8—H8B0.9600C18—H180.9300
C8—H8C0.9600C19—H190.9300
C9—H9A0.9600
C1—N1—C10118.3 (3)O2—C9—H9C109.5
C3—O1—C8116.5 (3)H9A—C9—H9C109.5
C4—O2—C9117.8 (3)H9B—C9—H9C109.5
N1—C1—C2122.2 (3)C11—C10—N1122.3 (3)
N1—C1—H1118.9C11—C10—C15119.9 (3)
C2—C1—H1118.9N1—C10—C15117.7 (3)
C3—C2—C7119.1 (3)C10—C11—C12120.3 (3)
C3—C2—C1119.6 (3)C10—C11—H11119.8
C7—C2—C1121.3 (3)C12—C11—H11119.8
O1—C3—C2119.0 (3)C13—C12—C11121.1 (4)
O1—C3—C4120.1 (3)C13—C12—H12119.4
C2—C3—C4120.9 (3)C11—C12—H12119.4
O2—C4—C5125.1 (3)C12—C13—C14120.6 (3)
O2—C4—C3116.0 (3)C12—C13—H13119.7
C5—C4—C3118.9 (3)C14—C13—H13119.7
C4—C5—C6120.3 (3)C13—C14—C19122.4 (3)
C4—C5—H5119.8C13—C14—C15119.3 (3)
C6—C5—H5119.8C19—C14—C15118.3 (3)
C7—C6—C5121.2 (3)C16—C15—C14118.7 (3)
C7—C6—H6119.4C16—C15—C10122.4 (3)
C5—C6—H6119.4C14—C15—C10118.8 (3)
C6—C7—C2119.6 (3)C17—C16—C15121.1 (3)
C6—C7—H7120.2C17—C16—H16119.5
C2—C7—H7120.2C15—C16—H16119.5
O1—C8—H8A109.5C16—C17—C18120.0 (4)
O1—C8—H8B109.5C16—C17—H17120.0
H8A—C8—H8B109.5C18—C17—H17120.0
O1—C8—H8C109.5C19—C18—C17120.6 (4)
H8A—C8—H8C109.5C19—C18—H18119.7
H8B—C8—H8C109.5C17—C18—H18119.7
O2—C9—H9A109.5C18—C19—C14121.2 (3)
O2—C9—H9B109.5C18—C19—H19119.4
H9A—C9—H9B109.5C14—C19—H19119.4
C10—N1—C1—C2177.7 (3)C1—N1—C10—C15130.1 (3)
N1—C1—C2—C3162.3 (3)N1—C10—C11—C12177.0 (3)
N1—C1—C2—C718.7 (5)C15—C10—C11—C120.9 (5)
C8—O1—C3—C2109.7 (3)C10—C11—C12—C130.5 (6)
C8—O1—C3—C473.1 (4)C11—C12—C13—C140.1 (6)
C7—C2—C3—O1175.4 (3)C12—C13—C14—C19178.3 (3)
C1—C2—C3—O13.7 (4)C12—C13—C14—C150.3 (5)
C7—C2—C3—C41.8 (5)C13—C14—C15—C16177.8 (3)
C1—C2—C3—C4179.1 (3)C19—C14—C15—C160.7 (4)
C9—O2—C4—C53.0 (5)C13—C14—C15—C100.1 (4)
C9—O2—C4—C3176.6 (3)C19—C14—C15—C10178.7 (3)
O1—C3—C4—O23.7 (4)C11—C10—C15—C16177.2 (3)
C2—C3—C4—O2179.2 (3)N1—C10—C15—C164.8 (4)
O1—C3—C4—C5175.9 (3)C11—C10—C15—C140.7 (4)
C2—C3—C4—C51.2 (5)N1—C10—C15—C14177.3 (3)
O2—C4—C5—C6179.1 (3)C14—C15—C16—C170.4 (5)
C3—C4—C5—C60.5 (5)C10—C15—C16—C17177.5 (3)
C4—C5—C6—C71.6 (6)C15—C16—C17—C181.0 (5)
C5—C6—C7—C21.1 (6)C16—C17—C18—C190.4 (5)
C3—C2—C7—C60.6 (5)C17—C18—C19—C140.7 (5)
C1—C2—C7—C6179.7 (3)C13—C14—C19—C18177.2 (3)
C1—N1—C10—C1151.9 (4)C15—C14—C19—C181.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8C···O1i0.962.543.232 (4)129
C8—H8C···O20.962.432.998 (4)118
C16—H16···N10.932.522.839 (4)101
Symmetry code: (i) x1/2, y, z+3/2.

Experimental details

Crystal data
Chemical formulaC19H17NO2
Mr291.34
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)298
a, b, c (Å)7.7163 (7), 17.0786 (16), 23.427 (2)
V3)3087.3 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.48 × 0.45 × 0.36
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.962, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
14855, 2721, 1452
Rint0.057
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.187, 1.12
No. of reflections2721
No. of parameters202
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.15

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8C···O1i0.962.543.232 (4)129
Symmetry code: (i) x1/2, y, z+3/2.
 

Acknowledgements

The authors wish to acknowledge the Scientific and Technological Project of the Shanxi Science and Technology Agency (2006031083–01), the Scientific and Technological Project of Shanxi Province Health Department (200651) and the Shanxi University of Traditional Chinese Medicine Eleventh Five-Year Program of Science and Technology Industry (2006).

References

First citationBruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, Z. H., Morimoto, H., Matsunaga, S. & Shibasaki, M. (2008). J. Am. Chem. Soc. 130, 2170–2171.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationMay, J. P., Ting, R., Lermer, L., Thomas, J. M., Roupioz, Y. & Perrin, D. M. (2004). J. Am. Chem. Soc. 126, 4145–4156.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTariq, M. I., Ahmad, S., Tahir, M. N., Sarfaraz, M. & Hussain, I. (2010). Acta Cryst. E66, o1561.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWeber, B., Tandon, R. & Himsl, D. (2007). Z. Anorg. Allg. Chem. 633, 1159–1162.  Web of Science CSD CrossRef CAS Google Scholar
First citationZhu, R., Zhang, Y. & Ren, Y. (2010). Acta Cryst. E66, o2337.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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