8-Bromo-naphthalen-1-amine.

The title compound, C(10)H(8)BrN, was obtained by slow addition of sodium azide to 8-bromo-1-naphthoic acid, followed by addition of aqueous ammonia. The crude product was crystallized from petroleum ether to give pink crystals. Compared to other 1,8-disubstituted naphthalene compounds, this compound exhibits less strain between the 1 and 8 substituents. Additionally, the NH protons form both intra- and inter-molecular hydrogen bonds. The naphthalene units are arranged in a herring-bone stacking motif.

Related literature

For examples of sterically crowded 1,8 dichalcogen naphthalenes, see: Aucott et al. (2004 ▶). For the synthesis, see: Herbert et al. (1987 ▶).

Experimental

Crystal data

C10H8BrN

M = 222.08

Monoclinic,

a = 13.6692 (14) Å

b = 4.1579 (4) Å

c = 15.8256 (16) Å

β = 109.941 (3)°

V = 845.52 (15) Å3

Z = 4

Mo Kα radiation

μ = 4.81 mm−1

T = 125.1 K

0.35 × 0.13 × 0.09 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.381, T max = 0.649

6823 measured reflections

1527 independent reflections

1281 reflections with F 2 > 2σ(F 2)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.116

S = 1.10

1527 reflections

110 parameters

H-atom parameters constrained

Δρmax = 1.76 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SCXmini (Rigaku/MSC, 2006 ▶); cell refinement: PROCESS-AUTO (Rigaku, 1998 ▶); data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku/MSC, 2006 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012580/si2087sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012580/si2087Isup2.hkl

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

C10H8BrN	F000 = 440.00
Mr = 222.08	Dx = 1.744 Mg m−3
Monoclinic, P21/n	Melting point: 359 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71075 Å
a = 13.6692 (14) Å	Cell parameters from 7235 reflections
b = 4.1579 (4) Å	θ = 3.0–27.6º
c = 15.8256 (16) Å	µ = 4.81 mm−1
β = 109.941 (3)º	T = 125.1 K
V = 845.52 (15) Å3	Prism, pink
Z = 4	0.35 × 0.13 × 0.09 mm

Rigaku SCXmini diffractometer	1281 reflections with F2 > 2σ(F2)
Detector resolution: 6.85 pixels mm-1	Rint = 0.061
ω scans	θmax = 25.4º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −16→16
Tmin = 0.381, Tmax = 0.649	k = −5→5
6823 measured reflections	l = −19→19
1527 independent reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0516P)2 + 2.4354P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.051	(Δ/σ)max = 0.002
wR(F2) = 0.116	Δρmax = 1.76 e Å−3
S = 1.10	Δρmin = −0.39 e Å−3
1527 reflections	Extinction correction: none
110 parameters

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.

	x	y	z	Uiso*/Ueq
Br(1)	0.31174 (4)	0.55948 (14)	0.53932 (4)	0.0293 (2)
N(1)	0.3079 (3)	0.8778 (7)	0.71320 (17)	0.0237 (10)
C(1)	0.4427 (3)	0.4617 (12)	0.6330 (3)	0.0198 (11)
C(2)	0.5076 (4)	0.2842 (13)	0.6015 (3)	0.0257 (12)
C(3)	0.6037 (4)	0.1842 (14)	0.6610 (4)	0.0304 (13)
C(4)	0.6321 (4)	0.2554 (12)	0.7494 (4)	0.0274 (13)
C(5)	0.5666 (4)	0.4409 (12)	0.7842 (3)	0.0224 (11)
C(6)	0.5988 (4)	0.5102 (13)	0.8776 (4)	0.0349 (15)
C(7)	0.5414 (4)	0.6701 (14)	0.9140 (3)	0.0263 (12)
C(8)	0.4419 (4)	0.8017 (14)	0.8560 (3)	0.0314 (13)
C(9)	0.4054 (3)	0.7493 (12)	0.7623 (3)	0.0206 (11)
C(10)	0.4667 (3)	0.5569 (11)	0.7240 (3)	0.0157 (10)
H(1a)	0.2955	0.8886	0.6486	0.020*
H(2a)	0.4872	0.2298	0.5396	0.031*
H(3a)	0.6495	0.0651	0.6393	0.037*
H(4a)	0.6971	0.1804	0.7892	0.033*
H(1b)	0.2991	1.0681	0.7464	0.057*
H(6a)	0.6652	0.4367	0.9152	0.042*
H(7a)	0.5638	0.7006	0.9772	0.032*
H(8a)	0.4010	0.9253	0.8820	0.038*

	U11	U22	U33	U12	U13	U23
Br(1)	0.0265 (3)	0.0337 (3)	0.0210 (3)	0.0021 (2)	−0.0007 (2)	−0.0014 (2)
N(1)	0.023 (2)	0.020 (2)	0.029 (2)	0.0018 (19)	0.011 (2)	−0.0008 (18)
C(1)	0.018 (2)	0.025 (2)	0.014 (2)	−0.003 (2)	0.003 (2)	0.003 (2)
C(2)	0.034 (3)	0.021 (2)	0.025 (3)	−0.001 (2)	0.014 (2)	−0.001 (2)
C(3)	0.027 (3)	0.025 (3)	0.046 (3)	0.000 (2)	0.021 (2)	−0.001 (2)
C(4)	0.016 (2)	0.016 (3)	0.045 (3)	0.000 (2)	0.004 (2)	0.010 (2)
C(5)	0.020 (2)	0.016 (2)	0.026 (2)	−0.005 (2)	0.001 (2)	0.005 (2)
C(6)	0.021 (2)	0.022 (3)	0.043 (3)	−0.009 (2)	−0.013 (2)	0.016 (2)
C(7)	0.0278 (14)	0.0273 (15)	0.0247 (14)	−0.0040 (9)	0.0100 (9)	−0.0020 (9)
C(8)	0.035 (3)	0.026 (3)	0.038 (3)	−0.012 (2)	0.019 (2)	−0.010 (2)
C(9)	0.024 (2)	0.014 (3)	0.026 (2)	−0.009 (2)	0.011 (2)	−0.003 (2)
C(10)	0.015 (2)	0.014 (2)	0.019 (2)	−0.005 (2)	0.007 (2)	−0.0002 (19)

Br(1)—C(1)	1.939 (4)	C(8)—C(9)	1.410 (7)
N(1)—C(9)	1.400 (5)	C(9)—C(10)	1.435 (8)
C(1)—C(2)	1.372 (8)	N(1)—H(1a)	0.98
C(1)—C(10)	1.420 (7)	N(1)—H(1b)	0.98
C(2)—C(3)	1.393 (7)	C(2)—H(2a)	0.95
C(3)—C(4)	1.350 (8)	C(3)—H(3a)	0.95
C(4)—C(5)	1.428 (8)	C(4)—H(4a)	0.95
C(5)—C(6)	1.420 (8)	C(6)—H(6a)	0.95
C(5)—C(10)	1.455 (6)	C(7)—H(7a)	0.95
C(6)—C(7)	1.304 (9)	C(8)—H(8a)	0.95
C(7)—C(8)	1.462 (7)
Br(1)—C(1)—C(2)	112.2 (3)	C(5)—C(10)—C(9)	117.4 (4)
Br(1)—C(1)—C(10)	123.4 (4)	C(9)—N(1)—H(1a)	113.0
C(2)—C(1)—C(10)	124.4 (4)	C(9)—N(1)—H(1b)	106.2
C(1)—C(2)—C(3)	119.4 (5)	H(1a)—N(1)—H(1b)	120.9
C(2)—C(3)—C(4)	120.5 (6)	C(1)—C(2)—H(2a)	120.3
C(3)—C(4)—C(5)	121.4 (4)	C(3)—C(2)—H(2a)	120.3
C(4)—C(5)—C(6)	119.9 (4)	C(2)—C(3)—H(3a)	119.8
C(4)—C(5)—C(10)	119.9 (4)	C(4)—C(3)—H(3a)	119.8
C(6)—C(5)—C(10)	120.2 (5)	C(3)—C(4)—H(4a)	119.3
C(5)—C(6)—C(7)	123.0 (4)	C(5)—C(4)—H(4a)	119.3
C(6)—C(7)—C(8)	118.9 (5)	C(5)—C(6)—H(6a)	118.5
C(7)—C(8)—C(9)	121.5 (5)	C(7)—C(6)—H(6a)	118.5
N(1)—C(9)—C(8)	117.0 (5)	C(6)—C(7)—H(7a)	120.5
N(1)—C(9)—C(10)	124.1 (4)	C(8)—C(7)—H(7a)	120.5
C(8)—C(9)—C(10)	118.8 (4)	C(7)—C(8)—H(8a)	119.3
C(1)—C(10)—C(5)	114.4 (4)	C(9)—C(8)—H(8a)	119.3
C(1)—C(10)—C(9)	128.2 (4)
Br(1)—C(1)—C(2)—C(3)	−177.8 (4)	C(4)—C(5)—C(10)—C(9)	−178.4 (5)
Br(1)—C(1)—C(10)—C(5)	176.3 (3)	C(6)—C(5)—C(10)—C(1)	−178.0 (5)
Br(1)—C(1)—C(10)—C(9)	−3.7 (8)	C(6)—C(5)—C(10)—C(9)	2.0 (7)
C(2)—C(1)—C(10)—C(5)	−2.0 (8)	C(10)—C(5)—C(6)—C(7)	1.7 (9)
C(2)—C(1)—C(10)—C(9)	178.0 (5)	C(5)—C(6)—C(7)—C(8)	−3.8 (9)
C(10)—C(1)—C(2)—C(3)	0.6 (9)	C(6)—C(7)—C(8)—C(9)	2.4 (9)
C(1)—C(2)—C(3)—C(4)	1.3 (9)	C(7)—C(8)—C(9)—N(1)	178.2 (5)
C(2)—C(3)—C(4)—C(5)	−1.6 (9)	C(7)—C(8)—C(9)—C(10)	1.2 (8)
C(3)—C(4)—C(5)—C(6)	179.7 (5)	N(1)—C(9)—C(10)—C(1)	0.0 (8)
C(3)—C(4)—C(5)—C(10)	0.1 (6)	N(1)—C(9)—C(10)—C(5)	−180.0 (4)
C(4)—C(5)—C(6)—C(7)	−177.9 (5)	C(8)—C(9)—C(10)—C(1)	176.8 (5)
C(4)—C(5)—C(10)—C(1)	1.6 (7)	C(8)—C(9)—C(10)—C(5)	−3.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1a···Br1	0.98	2.27	3.070 (3)	138
N1—H1b···N1i	0.98	2.20	3.073 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1a⋯Br1	0.98	2.27	3.070 (3)	138
N1—H1b⋯N1i	0.98	2.20	3.073 (5)	148

Symmetry code: (i) .