N-(4-Chloro­benzyl­idene)-1-naphthyl­amine

Zhu, R.; Zhang, Y.; Ren, Y.

doi:10.1107/S1600536810032332

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2337

https://doi.org/10.1107/S1600536810032332

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N-(4-Chlorobenzylidene)-1-naphthylamine

Ruitao Zhu,^a Yuewen Zhang ^a and Yuehong Ren ^a ^*

^aDepartment of Chemistry, Taiyuan Normal University, Taiyuan 030031, People's Republic of China
^*Correspondence e-mail: ruitaozhu@126.com

(Received 23 July 2010; accepted 11 August 2010; online 18 August 2010)

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, P 2₁ /c
a = 12.8416 (13) Å
b = 14.8771 (15) Å
c = 7.1971 (8) Å
β = 92.857 (1)°
V = 1373.3 (2) Å³
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[F² > 2σ(F²)] = 0.049
wR(F²) = 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810032332/ya2125sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032332/ya2125Isup2.hkl

checkCIF report

Comment top

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)°.

Related literature top

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 the structures of related compounds, see: Harada et al. (2004); Tariq et al. (2010).

Experimental top

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.

Structure description top

Computing details top

Data collection: APEX2 (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-(4-Chlorobenzylidene)-1-naphthylamine top

Crystal data top

C₁₇H₁₂ClN	F(000) = 552
M_r = 265.73	D_x = 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 top

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

Refinement top

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(F_o²) + (0.0469P)² + 0.2941P] where P = (F_o² + 2F_c²)/3
2421 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₇H₁₂ClN	V = 1373.3 (2) Å³
M_r = 265.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.8416 (13) Å	µ = 0.26 mm⁻¹
b = 14.8771 (15) Å	T = 296 K
c = 7.1971 (8) Å	0.30 × 0.24 × 0.20 mm
β = 92.857 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2421 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1489 reflections with I > 2σ(I)
T_min = 0.925, T_max = 0.949	R_int = 0.038
6607 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.03	Δρ_max = 0.16 e Å⁻³
2421 reflections	Δρ_min = −0.22 e Å⁻³
172 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
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 (Å²) top

	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, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂ClN
M_r	265.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.8416 (13), 14.8771 (15), 7.1971 (8)
β (°)	92.857 (1)
V (Å³)	1373.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.30 × 0.24 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.925, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	6607, 2421, 1489
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.127, 1.03
No. of reflections	2421
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.22

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

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