N-(4-Chloro­benzyl­idene)-1-naphthyl­amine

Abstract

The title compound, C₁₇H₁₂ClN, represents a trans isomer with respect to the C=N bond; the dihedral angle between the planes of the naphthyl and benzene groups is 66.53 (5)°.

Related literature

For general background on the properties of Schiff bases, see: Layer (1963 ▶); Chen et al. (2008 ▶); May et al. (2004 ▶); Weber et al. (2007 ▶). For related structures, see: Harada et al. (2004 ▶); Tariq et al. (2010 ▶).

Experimental

Crystal data

• C₁₇H₁₂ClN

• M _r = 265.73

• Monoclinic,

• a = 12.8416 (13) Å

• b = 14.8771 (15) Å

• c = 7.1971 (8) Å

• β = 92.857 (1)°

• V = 1373.3 (2) ų

• Z = 4

• Mo Kα radiation

• μ = 0.26 mm⁻¹

• T = 296 K

• 0.30 × 0.24 × 0.20 mm

Data collection

• Bruker APEXII CCD diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.925, T _max = 0.949

• 6607 measured reflections

• 2421 independent reflections

• 1489 reflections with I > 2σ(I)

• R _int = 0.038

Refinement

• R[F ² > 2σ(F ²)] = 0.049

• wR(F ²) = 0.127

• S = 1.03

• 2421 reflections

• 172 parameters

• H-atom parameters constrained

• Δρ_max = 0.16 e Å⁻³

• Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (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.

Supplementary Material

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

supplementary crystallographic information

Comment

The Schiff bases have been receiving 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).

As a part of our studies on synthesis and structural peculiarities of Schiff bases derived from naphthylamine and arylaldehydes, we determined the structure of the title compound (Fig. 1). The molecule represents a trans-isomer with respect to the C11═N1 bond. The planes of the aromatic systems of the the naphthyl and benzene groups, C1–C10 and C12–C17 respectively, form dihedral angle of 66.53 (5)°.

Experimental

1-Naphthylamine (0.72 g, 5 mmol) and 4-chlorobenzaldehyde (0.70 g, 5 mmol) were dissolved in ethanol (20 ml). The mixture was refluxed for 6 h, and then cooled to room temperature. The reaction mixture was filtered and the filter cake was recrystallized 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

H atoms were placed in idealized positions and allowed to ride on their respective parent atoms, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C).

Figures

Fig. 1.

A view of the molecular structure of the title compound; displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C17H12ClN	F(000) = 552
Mr = 265.73	Dx = 1.285 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1396 reflections
a = 12.8416 (13) Å	θ = 3.0–21.8°
b = 14.8771 (15) Å	µ = 0.26 mm−1
c = 7.1971 (8) Å	T = 296 K
β = 92.857 (1)°	Prism, colourless
V = 1373.3 (2) Å3	0.30 × 0.24 × 0.20 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	2421 independent reflections
Radiation source: fine-focus sealed tube	1489 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.925, Tmax = 0.949	k = −17→13
6607 measured reflections	l = −8→8

Refinement

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.2941P] where P = (Fo2 + 2Fc2)/3
2421 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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
Cl1	1.41202 (5)	0.30834 (6)	1.24470 (11)	0.0803 (3)
N1	0.92436 (15)	0.37176 (15)	0.8844 (3)	0.0512 (6)
C1	0.81851 (19)	0.36531 (17)	0.8206 (4)	0.0481 (6)
C2	0.7440 (2)	0.3300 (2)	0.9273 (4)	0.0593 (8)
H2	0.7634	0.3045	1.0418	0.071*
C3	0.6383 (2)	0.3315 (2)	0.8669 (4)	0.0733 (9)
H3	0.5885	0.3071	0.9416	0.088*
C4	0.6086 (2)	0.3681 (2)	0.7013 (5)	0.0713 (9)
H4	0.5383	0.3691	0.6635	0.086*
C5	0.6828 (2)	0.40512 (19)	0.5839 (4)	0.0553 (7)
C6	0.78968 (18)	0.40408 (17)	0.6440 (3)	0.0456 (6)
C7	0.8628 (2)	0.44051 (18)	0.5263 (4)	0.0545 (7)
H7	0.9331	0.4402	0.5642	0.065*
C8	0.8331 (3)	0.4761 (2)	0.3586 (4)	0.0705 (9)
H8	0.8830	0.4996	0.2829	0.085*
C9	0.7281 (3)	0.4776 (2)	0.2989 (4)	0.0786 (10)
H9	0.7083	0.5022	0.1837	0.094*
C10	0.6545 (2)	0.4433 (2)	0.4087 (4)	0.0710 (9)
H10	0.5847	0.4449	0.3679	0.085*
C11	0.97066 (19)	0.30238 (18)	0.9492 (3)	0.0484 (6)
H11	0.9351	0.2479	0.9460	0.058*
C12	1.07745 (18)	0.30453 (17)	1.0286 (3)	0.0422 (6)
C13	1.13264 (19)	0.22522 (18)	1.0563 (3)	0.0482 (6)
H13	1.0997	0.1706	1.0306	0.058*
C14	1.23542 (19)	0.2257 (2)	1.1212 (3)	0.0535 (7)
H14	1.2720	0.1721	1.1381	0.064*
C15	1.28284 (18)	0.3068 (2)	1.1604 (3)	0.0506 (7)
C16	1.22982 (19)	0.3865 (2)	1.1386 (3)	0.0544 (7)
H16	1.2628	0.4406	1.1686	0.065*
C17	1.12764 (19)	0.38576 (18)	1.0719 (3)	0.0512 (7)
H17	1.0917	0.4397	1.0556	0.061*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
Cl1	0.0504 (4)	0.1022 (8)	0.0871 (6)	0.0088 (4)	−0.0083 (4)	−0.0073 (5)
N1	0.0495 (12)	0.0453 (14)	0.0580 (14)	−0.0005 (10)	−0.0057 (10)	0.0032 (11)
C1	0.0474 (14)	0.0401 (16)	0.0566 (16)	−0.0019 (12)	0.0021 (12)	−0.0045 (13)
C2	0.0577 (16)	0.064 (2)	0.0564 (17)	−0.0055 (14)	0.0024 (13)	0.0084 (15)
C3	0.0532 (17)	0.087 (3)	0.080 (2)	−0.0136 (16)	0.0116 (15)	0.0087 (19)
C4	0.0469 (16)	0.076 (2)	0.090 (2)	−0.0074 (15)	−0.0090 (16)	0.0031 (19)
C5	0.0555 (16)	0.0449 (17)	0.0643 (18)	−0.0041 (13)	−0.0087 (14)	−0.0053 (14)
C6	0.0491 (14)	0.0347 (15)	0.0527 (16)	−0.0026 (11)	0.0008 (12)	−0.0058 (13)
C7	0.0585 (16)	0.0439 (17)	0.0614 (18)	−0.0009 (13)	0.0067 (13)	−0.0023 (14)
C8	0.089 (2)	0.059 (2)	0.064 (2)	−0.0085 (17)	0.0048 (17)	0.0063 (16)
C9	0.107 (3)	0.063 (2)	0.063 (2)	−0.011 (2)	−0.0192 (19)	0.0083 (17)
C10	0.074 (2)	0.059 (2)	0.077 (2)	−0.0077 (17)	−0.0272 (17)	0.0013 (18)
C11	0.0543 (15)	0.0436 (17)	0.0476 (14)	−0.0036 (13)	0.0042 (12)	0.0021 (13)
C12	0.0498 (13)	0.0404 (16)	0.0366 (13)	−0.0005 (12)	0.0034 (10)	0.0047 (12)
C13	0.0569 (15)	0.0388 (16)	0.0495 (15)	−0.0004 (13)	0.0080 (12)	0.0035 (13)
C14	0.0576 (16)	0.0502 (18)	0.0531 (16)	0.0134 (14)	0.0082 (13)	0.0073 (14)
C15	0.0462 (14)	0.0599 (19)	0.0457 (15)	0.0067 (14)	0.0038 (11)	−0.0010 (14)
C16	0.0536 (15)	0.0518 (19)	0.0574 (17)	−0.0033 (14)	−0.0015 (13)	−0.0066 (14)
C17	0.0561 (15)	0.0435 (17)	0.0534 (16)	0.0048 (13)	−0.0033 (12)	0.0022 (13)

Geometric parameters (Å, °)

Cl1—C15	1.738 (2)	C8—H8	0.9300
N1—C11	1.268 (3)	C9—C10	1.361 (4)
N1—C1	1.416 (3)	C9—H9	0.9300
C1—C2	1.361 (4)	C10—H10	0.9300
C1—C6	1.427 (3)	C11—C12	1.459 (3)
C2—C3	1.405 (4)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.386 (3)
C3—C4	1.348 (4)	C12—C17	1.397 (3)
C3—H3	0.9300	C13—C14	1.378 (3)
C4—C5	1.416 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.375 (4)
C5—C10	1.414 (4)	C14—H14	0.9300
C5—C6	1.419 (3)	C15—C16	1.372 (4)
C6—C7	1.404 (3)	C16—C17	1.375 (3)
C7—C8	1.355 (4)	C16—H16	0.9300
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.395 (4)
C11—N1—C1	119.3 (2)	C10—C9—H9	119.9
C2—C1—N1	122.2 (2)	C8—C9—H9	119.9
C2—C1—C6	120.0 (2)	C9—C10—C5	120.9 (3)
N1—C1—C6	117.6 (2)	C9—C10—H10	119.5
C1—C2—C3	121.0 (3)	C5—C10—H10	119.5
C1—C2—H2	119.5	N1—C11—C12	122.7 (2)
C3—C2—H2	119.5	N1—C11—H11	118.6
C4—C3—C2	120.5 (3)	C12—C11—H11	118.6
C4—C3—H3	119.8	C13—C12—C17	118.5 (2)
C2—C3—H3	119.8	C13—C12—C11	120.1 (2)
C3—C4—C5	121.0 (3)	C17—C12—C11	121.3 (2)
C3—C4—H4	119.5	C14—C13—C12	121.2 (2)
C5—C4—H4	119.5	C14—C13—H13	119.4
C10—C5—C4	122.5 (3)	C12—C13—H13	119.4
C10—C5—C6	118.5 (3)	C15—C14—C13	118.8 (2)
C4—C5—C6	118.9 (3)	C15—C14—H14	120.6
C7—C6—C5	118.5 (2)	C13—C14—H14	120.6
C7—C6—C1	122.8 (2)	C16—C15—C14	121.5 (2)
C5—C6—C1	118.7 (2)	C16—C15—Cl1	119.2 (2)
C8—C7—C6	121.4 (3)	C14—C15—Cl1	119.2 (2)
C8—C7—H7	119.3	C15—C16—C17	119.5 (3)
C6—C7—H7	119.3	C15—C16—H16	120.2
C7—C8—C9	120.4 (3)	C17—C16—H16	120.2
C7—C8—H8	119.8	C16—C17—C12	120.4 (2)
C9—C8—H8	119.8	C16—C17—H17	119.8
C10—C9—C8	120.2 (3)	C12—C17—H17	119.8
C11—N1—C1—C2	52.2 (4)	C6—C7—C8—C9	0.2 (4)
C11—N1—C1—C6	−132.8 (2)	C7—C8—C9—C10	−0.1 (5)
N1—C1—C2—C3	174.4 (3)	C8—C9—C10—C5	−0.4 (5)
C6—C1—C2—C3	−0.4 (4)	C4—C5—C10—C9	−179.5 (3)
C1—C2—C3—C4	0.1 (5)	C6—C5—C10—C9	0.6 (4)
C2—C3—C4—C5	0.5 (5)	C1—N1—C11—C12	−176.0 (2)
C3—C4—C5—C10	179.4 (3)	N1—C11—C12—C13	−164.6 (2)
C3—C4—C5—C6	−0.7 (5)	N1—C11—C12—C17	13.0 (4)
C10—C5—C6—C7	−0.4 (4)	C17—C12—C13—C14	−1.4 (4)
C4—C5—C6—C7	179.7 (3)	C11—C12—C13—C14	176.3 (2)
C10—C5—C6—C1	−179.8 (2)	C12—C13—C14—C15	0.7 (4)
C4—C5—C6—C1	0.3 (4)	C13—C14—C15—C16	0.8 (4)
C2—C1—C6—C7	−179.1 (3)	C13—C14—C15—Cl1	179.32 (19)
N1—C1—C6—C7	5.8 (4)	C14—C15—C16—C17	−1.5 (4)
C2—C1—C6—C5	0.2 (4)	Cl1—C15—C16—C17	180.0 (2)
N1—C1—C6—C5	−174.9 (2)	C15—C16—C17—C12	0.7 (4)
C5—C6—C7—C8	0.0 (4)	C13—C12—C17—C16	0.7 (4)
C1—C6—C7—C8	179.3 (3)	C11—C12—C17—C16	−177.0 (2)