N-(4-Bromo­benzyl­idene)naphthalen-1-amine

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

doi:10.1107/S1600536812019800

organic compounds

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Volume 68| Part 6| June 2012| Page o1671

doi:10.1107/S1600536812019800

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N-(4-Bromobenzylidene)naphthalen-1-amine

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

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

(Received 27 April 2012; accepted 3 May 2012; online 12 May 2012)

The title molecule, C₁₇H₁₂BrN, is in a E conformation with respect to the C=N bond. The dihedral angle between the naphthalene ring system and the benzene ring is 53.26 (3)°.

Related literature

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

Experimental

Crystal data

C₁₇H₁₂BrN
M_r = 310.19
Monoclinic, P 2₁ /c
a = 7.0823 (6) Å
b = 25.555 (2) Å
c = 7.5712 (5) Å
β = 94.431 (1)°
V = 1366.19 (18) Å³
Z = 4
Mo Kα radiation
μ = 2.99 mm⁻¹
T = 298 K
0.45 × 0.41 × 0.28 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.346, T_max = 0.488
6750 measured reflections
2405 independent reflections
1643 reflections with I > 2σ(I)
R_int = 0.080

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.100
S = 1.03
2405 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.32 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812019800/lh5468sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812019800/lh5468Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812019800/lh5468Isup3.cml

checkCIF report

Comment top

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 the synthesis and structural properties of Schiff bases with naphthylamine and arylaldehydes, we have determined the structure of the title compound (Fig. 1). The molecule is in a trans configuration with respect to the C11═N1 bond. The mean planes of the naphthylene ring system and benzene ring, C1—C10 and C12—C17 respectively, form dihedral angle of 53.26 (3)°. Some examples of related structures already appear in the literature (Zhu et al., 2010; Harada et al., 2004; Tariq et al., 2010).

Related literature top

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

Experimental top

1-Naphthylamine (0.72 g,5 mmol) and p-bromobenzaldehyde (0.92 g, 5 mmol) were dissolved in ethanol (30 ml). The mixture was refluxed for 2 h, and then cooled to room temperature. The reaction mixture was filtered and the filter cake was recreystallized from ethyl alcohol (yield 90%). Crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution of the title compound.

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. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

N-(4-Bromobenzylidene)naphthalen-1-amine top

Crystal data top

C₁₇H₁₂BrN	F(000) = 624
M_r = 310.19	D_x = 1.508 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2253 reflections
a = 7.0823 (6) Å	θ = 2.7–24.1°
b = 25.555 (2) Å	µ = 2.99 mm⁻¹
c = 7.5712 (5) Å	T = 298 K
β = 94.431 (1)°	Block, yellow
V = 1366.19 (18) Å³	0.45 × 0.41 × 0.28 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2405 independent reflections
Radiation source: fine-focus sealed tube	1643 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.346, T_max = 0.488	k = −24→30
6750 measured reflections	l = −9→8

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)] = 0.043	H-atom parameters constrained
wR(F²) = 0.100	w = 1/[σ²(F_o²) + (0.0289P)² + 0.2762P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2405 reflections	Δρ_max = 0.45 e Å⁻³
173 parameters	Δρ_min = −0.32 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: 0.0366 (19)

Crystal data top

C₁₇H₁₂BrN	V = 1366.19 (18) Å³
M_r = 310.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0823 (6) Å	µ = 2.99 mm⁻¹
b = 25.555 (2) Å	T = 298 K
c = 7.5712 (5) Å	0.45 × 0.41 × 0.28 mm
β = 94.431 (1)°

Data collection top

Bruker SMART CCD diffractometer	2405 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1643 reflections with I > 2σ(I)
T_min = 0.346, T_max = 0.488	R_int = 0.080
6750 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	Δρ_max = 0.45 e Å⁻³
2405 reflections	Δρ_min = −0.32 e Å⁻³
173 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
Br1	−0.13531 (5)	0.479652 (16)	0.74533 (7)	0.0722 (3)
N1	0.4392 (3)	0.26397 (10)	0.6574 (4)	0.0388 (7)
C1	0.4699 (4)	0.30922 (13)	0.7241 (4)	0.0368 (8)
H1	0.5918	0.3173	0.7707	0.044*
C2	0.3235 (4)	0.34896 (12)	0.7310 (4)	0.0353 (8)
C3	0.3651 (5)	0.39638 (13)	0.8152 (5)	0.0452 (9)
H3	0.4857	0.4018	0.8698	0.054*
C4	0.2310 (5)	0.43560 (13)	0.8194 (5)	0.0497 (10)
H4	0.2610	0.4674	0.8744	0.060*
C5	0.0531 (5)	0.42671 (13)	0.7408 (5)	0.0429 (9)
C6	0.0059 (5)	0.38013 (15)	0.6560 (5)	0.0492 (10)
H6	−0.1149	0.3749	0.6016	0.059*
C7	0.1413 (4)	0.34164 (13)	0.6537 (5)	0.0475 (10)
H7	0.1100	0.3099	0.5989	0.057*
C8	0.5943 (4)	0.22972 (13)	0.6450 (4)	0.0371 (8)
C9	0.7594 (4)	0.24571 (14)	0.5768 (5)	0.0453 (10)
H9	0.7726	0.2804	0.5422	0.054*
C10	0.9082 (5)	0.21025 (16)	0.5588 (5)	0.0546 (11)
H10	1.0187	0.2217	0.5121	0.066*
C11	0.8930 (5)	0.15948 (15)	0.6086 (5)	0.0558 (11)
H11	0.9932	0.1366	0.5960	0.067*
C12	0.7270 (5)	0.14119 (14)	0.6791 (5)	0.0440 (10)
C13	0.5735 (4)	0.17643 (12)	0.6966 (4)	0.0343 (8)
C14	0.4062 (5)	0.15755 (13)	0.7641 (4)	0.0430 (9)
H14	0.3048	0.1801	0.7752	0.052*
C15	0.3920 (5)	0.10638 (15)	0.8134 (5)	0.0552 (10)
H15	0.2805	0.0945	0.8570	0.066*
C16	0.5417 (6)	0.07172 (15)	0.7995 (6)	0.0609 (12)
H16	0.5307	0.0371	0.8351	0.073*
C17	0.7043 (6)	0.08871 (15)	0.7337 (6)	0.0585 (11)
H17	0.8033	0.0652	0.7242	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0609 (3)	0.0474 (3)	0.1084 (5)	0.01858 (19)	0.0070 (3)	−0.0096 (3)
N1	0.0399 (15)	0.0300 (16)	0.0466 (19)	0.0018 (12)	0.0048 (13)	−0.0012 (14)
C1	0.0397 (18)	0.033 (2)	0.038 (2)	−0.0005 (15)	0.0021 (15)	0.0049 (16)
C2	0.0434 (19)	0.0287 (19)	0.034 (2)	−0.0012 (15)	0.0055 (16)	0.0028 (15)
C3	0.047 (2)	0.036 (2)	0.051 (2)	0.0023 (16)	−0.0061 (18)	0.0006 (18)
C4	0.059 (2)	0.0260 (19)	0.063 (3)	0.0008 (17)	−0.001 (2)	−0.0061 (18)
C5	0.0459 (19)	0.032 (2)	0.052 (2)	0.0059 (16)	0.0117 (17)	0.0064 (18)
C6	0.0381 (19)	0.042 (2)	0.068 (3)	−0.0009 (17)	0.0076 (18)	−0.0029 (19)
C7	0.044 (2)	0.029 (2)	0.070 (3)	−0.0028 (16)	0.0113 (18)	−0.0076 (19)
C8	0.0351 (17)	0.040 (2)	0.035 (2)	0.0026 (15)	−0.0031 (15)	−0.0061 (16)
C9	0.0435 (19)	0.038 (2)	0.054 (3)	−0.0024 (16)	0.0033 (18)	−0.0066 (18)
C10	0.0395 (19)	0.053 (3)	0.073 (3)	−0.0048 (18)	0.0131 (19)	−0.015 (2)
C11	0.040 (2)	0.046 (3)	0.080 (3)	0.0071 (17)	−0.004 (2)	−0.024 (2)
C12	0.0397 (19)	0.038 (2)	0.053 (2)	0.0018 (16)	−0.0073 (18)	−0.0130 (18)
C13	0.0382 (17)	0.0290 (19)	0.035 (2)	0.0007 (15)	−0.0022 (15)	−0.0066 (16)
C14	0.050 (2)	0.035 (2)	0.044 (2)	0.0000 (16)	0.0041 (17)	−0.0072 (18)
C15	0.070 (3)	0.041 (2)	0.055 (3)	−0.009 (2)	0.014 (2)	−0.001 (2)
C16	0.078 (3)	0.030 (2)	0.073 (3)	−0.006 (2)	−0.005 (2)	0.006 (2)
C17	0.063 (2)	0.034 (2)	0.076 (3)	0.0115 (19)	−0.013 (2)	−0.008 (2)

Geometric parameters (Å, º) top

Br1—C5	1.902 (3)	C9—C10	1.405 (5)
N1—C1	1.274 (4)	C9—H9	0.9300
N1—C8	1.413 (4)	C10—C11	1.358 (5)
C1—C2	1.455 (4)	C10—H10	0.9300
C1—H1	0.9300	C11—C12	1.408 (5)
C2—C7	1.388 (4)	C11—H11	0.9300
C2—C3	1.390 (5)	C12—C17	1.416 (5)
C3—C4	1.383 (5)	C12—C13	1.426 (5)
C3—H3	0.9300	C13—C14	1.412 (4)
C4—C5	1.370 (5)	C14—C15	1.366 (5)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.381 (5)	C15—C16	1.392 (5)
C6—C7	1.375 (5)	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.361 (6)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.376 (5)	C17—H17	0.9300
C8—C13	1.427 (4)

C1—N1—C8	118.6 (3)	C8—C9—H9	119.7
N1—C1—C2	123.2 (3)	C10—C9—H9	119.7
N1—C1—H1	118.4	C11—C10—C9	120.9 (4)
C2—C1—H1	118.4	C11—C10—H10	119.6
C7—C2—C3	117.9 (3)	C9—C10—H10	119.6
C7—C2—C1	122.2 (3)	C10—C11—C12	120.6 (3)
C3—C2—C1	119.9 (3)	C10—C11—H11	119.7
C4—C3—C2	121.4 (3)	C12—C11—H11	119.7
C4—C3—H3	119.3	C11—C12—C17	122.8 (3)
C2—C3—H3	119.3	C11—C12—C13	119.4 (3)
C5—C4—C3	118.7 (3)	C17—C12—C13	117.8 (3)
C5—C4—H4	120.6	C14—C13—C12	119.0 (3)
C3—C4—H4	120.6	C14—C13—C8	122.2 (3)
C4—C5—C6	121.7 (3)	C12—C13—C8	118.8 (3)
C4—C5—Br1	119.8 (3)	C15—C14—C13	120.5 (3)
C6—C5—Br1	118.5 (2)	C15—C14—H14	119.7
C7—C6—C5	118.6 (3)	C13—C14—H14	119.7
C7—C6—H6	120.7	C14—C15—C16	121.1 (4)
C5—C6—H6	120.7	C14—C15—H15	119.5
C6—C7—C2	121.7 (3)	C16—C15—H15	119.5
C6—C7—H7	119.2	C17—C16—C15	119.7 (4)
C2—C7—H7	119.2	C17—C16—H16	120.1
C9—C8—N1	121.9 (3)	C15—C16—H16	120.1
C9—C8—C13	119.6 (3)	C16—C17—C12	121.9 (4)
N1—C8—C13	118.4 (3)	C16—C17—H17	119.1
C8—C9—C10	120.7 (3)	C12—C17—H17	119.1

C8—N1—C1—C2	175.2 (3)	C9—C10—C11—C12	0.2 (6)
N1—C1—C2—C7	−4.6 (5)	C10—C11—C12—C17	−179.7 (3)
N1—C1—C2—C3	176.3 (3)	C10—C11—C12—C13	0.5 (5)
C7—C2—C3—C4	−1.2 (6)	C11—C12—C13—C14	178.8 (3)
C1—C2—C3—C4	178.0 (3)	C17—C12—C13—C14	−1.0 (5)
C2—C3—C4—C5	1.0 (6)	C11—C12—C13—C8	−1.2 (5)
C3—C4—C5—C6	−1.0 (6)	C17—C12—C13—C8	179.0 (3)
C3—C4—C5—Br1	179.6 (3)	C9—C8—C13—C14	−178.7 (3)
C4—C5—C6—C7	1.1 (6)	N1—C8—C13—C14	−2.0 (5)
Br1—C5—C6—C7	−179.5 (3)	C9—C8—C13—C12	1.3 (5)
C5—C6—C7—C2	−1.3 (6)	N1—C8—C13—C12	178.0 (3)
C3—C2—C7—C6	1.3 (6)	C12—C13—C14—C15	0.5 (5)
C1—C2—C7—C6	−177.8 (4)	C8—C13—C14—C15	−179.5 (3)
C1—N1—C8—C9	−48.1 (5)	C13—C14—C15—C16	0.4 (6)
C1—N1—C8—C13	135.2 (3)	C14—C15—C16—C17	−0.9 (6)
N1—C8—C9—C10	−177.2 (3)	C15—C16—C17—C12	0.4 (6)
C13—C8—C9—C10	−0.6 (5)	C11—C12—C17—C16	−179.2 (4)
C8—C9—C10—C11	−0.1 (6)	C13—C12—C17—C16	0.5 (6)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂BrN
M_r	310.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.0823 (6), 25.555 (2), 7.5712 (5)
β (°)	94.431 (1)
V (Å³)	1366.19 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.99
Crystal size (mm)	0.45 × 0.41 × 0.28

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.346, 0.488
No. of measured, independent and observed [I > 2σ(I)] reflections	6750, 2405, 1643
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.100, 1.03
No. of reflections	2405
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.32

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

Acknowledgements

The authors gratefully acknowledge the Project of the Taiyuan Normal University Young Academic Leaders.

References

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