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

Guo, A.; Zhang, S.; Liu, X.; Jiao, J.

doi:10.1107/S1600536811000079

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o285

doi:10.1107/S1600536811000079

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

Ailing Guo,^a Shurong Zhang,^a ^* Xiaofang Liu ^a and Jianhua Jiao ^a

^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 ); 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_r = 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 ) 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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.187
S = 1.12
2721 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.15 e Å⁻³

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) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

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 C11═N1 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.

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

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

C₁₉H₁₇NO₂	F(000) = 1232
M_r = 291.34	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0462P)² + 2.0418P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
2721 reflections	Δρ_max = 0.18 e Å⁻³
202 parameters	Δρ_min = −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)

Crystal data top

C₁₉H₁₇NO₂	V = 3087.3 (5) Å³
M_r = 291.34	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.7163 (7) Å	µ = 0.08 mm⁻¹
b = 17.0786 (16) Å	T = 298 K
c = 23.427 (2) Å	0.48 × 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)
T_min = 0.962, T_max = 0.971	R_int = 0.057
14855 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.187	H-atom parameters constrained
S = 1.12	Δρ_max = 0.18 e Å⁻³
2721 reflections	Δρ_min = −0.15 e Å⁻³
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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x−1/2, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇NO₂
M_r	291.34
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	7.7163 (7), 17.0786 (16), 23.427 (2)
V (Å³)	3087.3 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.48 × 0.45 × 0.36

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.962, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	14855, 2721, 1452
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.187, 1.12
No. of reflections	2721
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C8—H8C···O1ⁱ	0.96	2.54	3.232 (4)	129

Symmetry code: (i) x−1/2, 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).

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