Naphthalen-1-aminium chloride.

In the crystal structure of the title compound, C(10)H(10)N(+)·Cl(-), the two components are connected via N-H⋯Cl hydrogen bonds, forming a layer parallel to the bc plane.

Related literature

For applications of naphthalene, see: Griego et al. (2008 ▶). For a related structure, see: Pitchumony & Stoeckli-Evans (2005 ▶).

Experimental

Crystal data

C10H10N+·Cl−

M = 179.64

Monoclinic,

a = 13.9691 (11) Å

b = 5.2811 (4) Å

c = 12.164 (1) Å

β = 93.791 (2)°

V = 895.40 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 296 K

0.50 × 0.11 × 0.06 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.838, T max = 0.978

7193 measured reflections

2612 independent reflections

2013 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.05

2612 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032569/is2764sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032569/is2764Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811032569/is2764Isup3.cml

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

C10H10N+·Cl−	F(000) = 376
Mr = 179.64	Dx = 1.333 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2184 reflections
a = 13.9691 (11) Å	θ = 2.4–29.5°
b = 5.2811 (4) Å	µ = 0.37 mm−1
c = 12.164 (1) Å	T = 296 K
β = 93.791 (2)°	Needle, blue
V = 895.40 (12) Å3	0.50 × 0.11 × 0.06 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	2612 independent reflections
Radiation source: fine-focus sealed tube	2013 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 30.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
Tmin = 0.838, Tmax = 0.978	k = −7→7
7193 measured reflections	l = −17→17

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) = 0.100	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0446P)2 + 0.1614P] where P = (Fo2 + 2Fc2)/3
2612 reflections	(Δ/σ)max = 0.001
110 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.09331 (7)	0.2065 (2)	0.61299 (9)	0.0337 (3)
H1A	0.0694	0.3349	0.6498	0.051*
H1B	0.0653	0.0629	0.6318	0.051*
H1C	0.0824	0.2324	0.5410	0.051*
C1	0.24993 (9)	0.0070 (3)	0.58382 (10)	0.0327 (3)
C2	0.20875 (10)	−0.1621 (3)	0.50320 (11)	0.0386 (3)
H2A	0.1430	−0.1576	0.4850	0.046*
C3	0.26516 (12)	−0.3317 (3)	0.45199 (13)	0.0481 (4)
H3A	0.2376	−0.4417	0.3993	0.058*
C4	0.36465 (12)	−0.3402 (4)	0.47879 (14)	0.0540 (4)
H4A	0.4024	−0.4558	0.4434	0.065*
C5	0.40605 (11)	−0.1815 (4)	0.55573 (14)	0.0500 (4)
H5A	0.4719	−0.1898	0.5723	0.060*
C6	0.35070 (9)	−0.0034 (3)	0.61123 (11)	0.0385 (3)
C7	0.39198 (10)	0.1629 (4)	0.69232 (13)	0.0489 (4)
H7A	0.4576	0.1557	0.7106	0.059*
C8	0.33727 (11)	0.3331 (4)	0.74393 (13)	0.0493 (4)
H8A	0.3658	0.4407	0.7971	0.059*
C9	0.23783 (10)	0.3478 (3)	0.71757 (11)	0.0390 (3)
H9A	0.2006	0.4647	0.7528	0.047*
C10	0.19664 (9)	0.1892 (3)	0.63994 (10)	0.0310 (3)
Cl1	0.02807 (2)	0.28819 (7)	0.36504 (2)	0.03865 (12)

	U11	U22	U33	U12	U13	U23
N1	0.0316 (5)	0.0390 (7)	0.0306 (5)	0.0057 (5)	0.0026 (4)	−0.0010 (5)
C1	0.0331 (6)	0.0343 (8)	0.0309 (5)	0.0033 (6)	0.0033 (4)	0.0064 (6)
C2	0.0390 (6)	0.0398 (9)	0.0370 (6)	0.0039 (6)	0.0040 (5)	−0.0009 (6)
C3	0.0569 (9)	0.0442 (10)	0.0438 (7)	0.0070 (8)	0.0080 (6)	−0.0054 (7)
C4	0.0563 (9)	0.0516 (11)	0.0557 (9)	0.0219 (9)	0.0159 (7)	0.0019 (8)
C5	0.0375 (7)	0.0562 (11)	0.0571 (9)	0.0142 (8)	0.0082 (6)	0.0076 (8)
C6	0.0329 (6)	0.0408 (9)	0.0419 (7)	0.0037 (6)	0.0032 (5)	0.0084 (6)
C7	0.0338 (6)	0.0589 (11)	0.0530 (8)	−0.0028 (7)	−0.0045 (6)	0.0052 (8)
C8	0.0438 (8)	0.0560 (11)	0.0471 (8)	−0.0101 (8)	−0.0048 (6)	−0.0070 (8)
C9	0.0411 (7)	0.0398 (8)	0.0362 (6)	0.0003 (7)	0.0034 (5)	−0.0025 (6)
C10	0.0311 (5)	0.0334 (7)	0.0286 (5)	0.0024 (6)	0.0026 (4)	0.0042 (5)
Cl1	0.04571 (19)	0.0405 (2)	0.03008 (16)	0.00534 (16)	0.00533 (12)	0.00064 (14)

N1—C10	1.4617 (16)	C4—C5	1.357 (3)
N1—H1A	0.8900	C4—H4A	0.9300
N1—H1B	0.8900	C5—C6	1.417 (2)
N1—H1C	0.8900	C5—H5A	0.9300
C1—C10	1.4189 (19)	C6—C7	1.415 (2)
C1—C2	1.420 (2)	C7—C8	1.360 (2)
C1—C6	1.4260 (17)	C7—H7A	0.9300
C2—C3	1.370 (2)	C8—C9	1.407 (2)
C2—H2A	0.9300	C8—H8A	0.9300
C3—C4	1.407 (2)	C9—C10	1.361 (2)
C3—H3A	0.9300	C9—H9A	0.9300
C10—N1—H1A	109.5	C4—C5—C6	121.17 (14)
C10—N1—H1B	109.5	C4—C5—H5A	119.4
H1A—N1—H1B	109.5	C6—C5—H5A	119.4
C10—N1—H1C	109.5	C7—C6—C5	122.29 (14)
H1A—N1—H1C	109.5	C7—C6—C1	119.33 (14)
H1B—N1—H1C	109.5	C5—C6—C1	118.38 (14)
C10—C1—C2	123.87 (12)	C8—C7—C6	121.10 (14)
C10—C1—C6	117.05 (13)	C8—C7—H7A	119.5
C2—C1—C6	119.08 (13)	C6—C7—H7A	119.5
C3—C2—C1	120.43 (13)	C7—C8—C9	120.51 (15)
C3—C2—H2A	119.8	C7—C8—H8A	119.7
C1—C2—H2A	119.8	C9—C8—H8A	119.7
C2—C3—C4	120.31 (16)	C10—C9—C8	119.33 (14)
C2—C3—H3A	119.8	C10—C9—H9A	120.3
C4—C3—H3A	119.8	C8—C9—H9A	120.3
C5—C4—C3	120.62 (15)	C9—C10—C1	122.68 (12)
C5—C4—H4A	119.7	C9—C10—N1	118.88 (12)
C3—C4—H4A	119.7	C1—C10—N1	118.44 (12)
C10—C1—C2—C3	179.52 (14)	C5—C6—C7—C8	179.64 (16)
C6—C1—C2—C3	−0.4 (2)	C1—C6—C7—C8	−0.4 (2)
C1—C2—C3—C4	0.0 (2)	C6—C7—C8—C9	−0.1 (3)
C2—C3—C4—C5	0.2 (3)	C7—C8—C9—C10	0.2 (2)
C3—C4—C5—C6	0.1 (3)	C8—C9—C10—C1	0.2 (2)
C4—C5—C6—C7	179.52 (17)	C8—C9—C10—N1	−179.85 (13)
C4—C5—C6—C1	−0.4 (2)	C2—C1—C10—C9	179.46 (14)
C10—C1—C6—C7	0.7 (2)	C6—C1—C10—C9	−0.6 (2)
C2—C1—C6—C7	−179.35 (14)	C2—C1—C10—N1	−0.53 (19)
C10—C1—C6—C5	−179.33 (13)	C6—C1—C10—N1	179.41 (12)
C2—C1—C6—C5	0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.89	2.41	3.1824 (11)	145.
N1—H1B···Cl1ii	0.89	2.27	3.1355 (11)	164.
N1—H1C···Cl1	0.89	2.24	3.1225 (11)	170.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.89	2.41	3.1824 (11)	145
N1—H1B⋯Cl1ii	0.89	2.27	3.1355 (11)	164
N1—H1C⋯Cl1	0.89	2.24	3.1225 (11)	170

Symmetry codes: (i) ; (ii) .