5-Amino-1-naphthol.

In the title compound, C(10)H(9)NO, the amino and the hydr-oxy groups act both as a single donor and a single acceptor in hydrogen bonding. In the crystal, mol-ecules are connected via chains of inter-molecular ⋯N-H⋯O-H⋯ inter-actions, forming a two-dimensional polymeric structure resembling the hydrogen-bonded mol-ecular assembly found in the crystal structure of naphthalene-1,5-diol. Within this layer, mol-ecules related by a translation along the a axis are arranged into slipped stacks via π-π stacking inter-actions [inter-planar distance = 3.450 (4) Å]. The amino N atom shows sp(3) hybridization and the two attached H atoms are located on the same side of the aromatic ring.

Related literature

For the crystal structure of 1,5-dihydroxy­naphthalene, see: Belskii et al. (1990 ▶). For amino-hydr­oxy group recognition and packing motifs of aminols, see: Ermer & Eling (1994 ▶); Hanessian et al. (1994 ▶); Allen et al. (1997 ▶); Dey et al. (2005 ▶).

Experimental

Crystal data

C10H9NO

M = 159.18

Orthorhombic,

a = 4.8607 (2) Å

b = 12.3175 (6) Å

c = 13.0565 (5) Å

V = 781.71 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 130 K

0.30 × 0.15 × 0.02 mm

Data collection

Kuma KM-4-CCD κ-geometry diffractometer

Absorption correction: none

8484 measured reflections

963 independent reflections

726 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.091

S = 1.06

963 reflections

121 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data <span class="Disease">reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045152/su2154sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045152/su2154Isup2.hkl

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

C10H9NO	Dx = 1.353 Mg m−3
Mr = 159.18	Melting point: 461 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2383 reflections
a = 4.8607 (2) Å	θ = 4–27°
b = 12.3175 (6) Å	µ = 0.09 mm−1
c = 13.0565 (5) Å	T = 130 K
V = 781.71 (6) Å3	Plate, pale pink
Z = 4	0.30 × 0.15 × 0.02 mm
F(000) = 336

Kuma KM-4-CCD κ-geometry diffractometer	726 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
graphite	θmax = 26.4°, θmin = 4.5°
ω scans	h = −6→5
8484 measured reflections	k = −15→15
963 independent reflections	l = −16→16

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0554P)2] where P = (Fo2 + 2Fc2)/3
963 reflections	(Δ/σ)max = 0.001
121 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.2605 (5)	0.48405 (18)	0.50574 (15)	0.0232 (5)
C2	0.1125 (5)	0.57846 (19)	0.51109 (17)	0.0269 (6)
H2	−0.0135	0.5887	0.5638	0.032*
C3	0.1504 (5)	0.65964 (19)	0.43738 (17)	0.0268 (6)
H3	0.0466	0.7230	0.4409	0.032*
C4	0.3386 (5)	0.64703 (19)	0.35998 (17)	0.0248 (6)
H4	0.3630	0.7022	0.3122	0.030*
C5	0.6956 (5)	0.53275 (18)	0.27339 (16)	0.0239 (6)
C6	0.8417 (5)	0.43775 (19)	0.26935 (17)	0.0265 (6)
H6	0.9701	0.4269	0.2175	0.032*
C7	0.7983 (5)	0.35673 (19)	0.34304 (17)	0.0283 (6)
H7	0.9009	0.2931	0.3399	0.034*
C8	0.6085 (5)	0.36936 (19)	0.41937 (17)	0.0256 (6)
H8	0.5795	0.3141	0.4667	0.031*
C9	0.4571 (5)	0.46670 (19)	0.42580 (16)	0.0215 (5)
C10	0.4964 (5)	0.55036 (18)	0.35220 (16)	0.0215 (5)
O11	0.2370 (4)	0.40173 (13)	0.57550 (11)	0.0289 (4)
H11O	0.067 (7)	0.404 (2)	0.609 (2)	0.058 (10)*
N12	0.7265 (5)	0.61211 (18)	0.19544 (14)	0.0275 (5)
H12A	0.699 (6)	0.685 (2)	0.2155 (18)	0.044 (8)*
H12B	0.899 (6)	0.601 (2)	0.1610 (19)	0.038 (8)*

	U11	U22	U33	U12	U13	U23
C1	0.0231 (12)	0.0279 (13)	0.0186 (10)	−0.0035 (12)	−0.0020 (11)	0.0014 (10)
C2	0.0250 (13)	0.0332 (14)	0.0226 (11)	−0.0002 (12)	0.0011 (11)	−0.0024 (11)
C3	0.0261 (13)	0.0255 (13)	0.0288 (12)	0.0028 (12)	−0.0008 (11)	−0.0047 (11)
C4	0.0250 (13)	0.0272 (13)	0.0223 (11)	−0.0030 (11)	−0.0017 (11)	0.0001 (10)
C5	0.0244 (14)	0.0283 (13)	0.0192 (10)	−0.0070 (11)	−0.0053 (10)	−0.0014 (10)
C6	0.0232 (13)	0.0334 (13)	0.0229 (11)	0.0006 (12)	0.0024 (10)	−0.0056 (11)
C7	0.0294 (15)	0.0244 (13)	0.0311 (12)	0.0055 (12)	−0.0022 (11)	−0.0044 (11)
C8	0.0273 (13)	0.0278 (13)	0.0216 (11)	−0.0011 (11)	−0.0013 (11)	−0.0004 (10)
C9	0.0187 (12)	0.0263 (13)	0.0194 (10)	−0.0006 (11)	−0.0030 (10)	−0.0036 (10)
C10	0.0204 (12)	0.0249 (13)	0.0191 (10)	−0.0044 (11)	−0.0044 (10)	−0.0006 (10)
O11	0.0269 (9)	0.0356 (10)	0.0243 (8)	−0.0003 (9)	0.0036 (8)	0.0061 (8)
N12	0.0271 (12)	0.0316 (13)	0.0237 (10)	−0.0025 (12)	0.0005 (10)	0.0016 (9)

C1—O11	1.368 (2)	C5—C10	1.430 (3)
C1—C2	1.369 (3)	C6—C7	1.402 (3)
C1—C9	1.431 (3)	C6—H6	0.9300
C2—C3	1.400 (3)	C7—C8	1.367 (3)
C2—H2	0.9300	C7—H7	0.9300
C3—C4	1.372 (3)	C8—C9	1.409 (3)
C3—H3	0.9300	C8—H8	0.9300
C4—C10	1.420 (3)	C9—C10	1.422 (3)
C4—H4	0.9300	O11—H11O	0.94 (3)
C5—C6	1.370 (3)	N12—H12A	0.95 (3)
C5—N12	1.419 (3)	N12—H12B	0.96 (3)
O11—C1—C2	123.5 (2)	C7—C6—H6	119.9
O11—C1—C9	115.5 (2)	C8—C7—C6	121.4 (2)
C2—C1—C9	120.99 (19)	C8—C7—H7	119.3
C1—C2—C3	120.2 (2)	C6—C7—H7	119.3
C1—C2—H2	119.9	C7—C8—C9	119.5 (2)
C3—C2—H2	119.9	C7—C8—H8	120.2
C4—C3—C2	120.9 (2)	C9—C8—H8	120.2
C4—C3—H3	119.6	C8—C9—C10	120.4 (2)
C2—C3—H3	119.6	C8—C9—C1	121.3 (2)
C3—C4—C10	120.5 (2)	C10—C9—C1	118.3 (2)
C3—C4—H4	119.7	C4—C10—C9	119.1 (2)
C10—C4—H4	119.7	C4—C10—C5	123.0 (2)
C6—C5—N12	120.4 (2)	C9—C10—C5	117.9 (2)
C6—C5—C10	120.6 (2)	C1—O11—H11O	111.6 (18)
N12—C5—C10	118.9 (2)	C5—N12—H12A	116.2 (15)
C5—C6—C7	120.2 (2)	C5—N12—H12B	109.1 (15)
C5—C6—H6	119.9	H12A—N12—H12B	113 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11O···N12i	0.94 (3)	1.83 (3)	2.749 (3)	167 (3)
N12—H12B···O11ii	0.96 (3)	2.09 (3)	3.046 (3)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11O⋯N12i	0.94 (3)	1.83 (3)	2.749 (3)	167 (3)
N12—H12B⋯O11ii	0.96 (3)	2.09 (3)	3.046 (3)	171 (2)

Symmetry codes: (i) ; (ii) .