(1-Naphthyl-meth-yl)ammonium chloride.

The reaction of 1-naphthyl-methyl-amine and hydro-chloric acid in a 1:1 molar ratio resulted in the formation of the 1:1 proton-transfer compound, C(11)H(12)N(+)·Cl(-). In the crystal, the ions are linked by N-H⋯Cl hydrogen bonds into a sheet pattern in the ab plane such that each Cl(-) ion is bonded to three NH groups from the naphthylmethylammonium ion.

Related literature

For 1-naphthyl­methyl­ammonium salts, see: Sada et al. (2004 ▶).

Experimental

Crystal data

C11H12N+·Cl−

M = 193.67

Monoclinic,

a = 5.3395 (7) Å

b = 9.3355 (15) Å

c = 10.1432 (13) Å

β = 100.864 (10)°

V = 496.55 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 298 K

0.35 × 0.13 × 0.11 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: numerical (X-RED and X-SHAPE; Stoe & Cie, 2005 ▶) T min = 0.952, T max = 0.968

5801 measured reflections

2677 independent reflections

2098 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.100

S = 1.19

2677 reflections

130 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 245 Friedel pairs

Flack parameter: 0.09 (10)

Data collection: X-AREA; cell refinement: X-AREA; data reduction: X-AREA; 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000334X/om2314sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000334X/om2314Isup2.hkl

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

C11H12N+·Cl−	F(000) = 204
Mr = 193.67	Dx = 1.295 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1056 reflections
a = 5.3395 (7) Å	θ = 2.0–29.2°
b = 9.3355 (15) Å	µ = 0.34 mm−1
c = 10.1432 (13) Å	T = 298 K
β = 100.864 (10)°	Prism, colorless
V = 496.55 (12) Å3	0.35 × 0.13 × 0.11 mm
Z = 2

Stoe IPDS II diffractometer	2098 reflections with I > 2σ(I)
rotation method scans	Rint = 0.065
Absorption correction: numerical (X-RED and X-SHAPE; Stoe & Cie, 2005)	θmax = 29.2°, θmin = 2.0°
Tmin = 0.952, Tmax = 0.968	h = −7→6
5801 measured reflections	k = −12→12
2677 independent reflections	l = −13→13

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0155P)2 + 0.2107P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.054	(Δ/σ)max = 0.002
wR(F2) = 0.100	Δρmax = 0.28 e Å−3
S = 1.19	Δρmin = −0.17 e Å−3
2677 reflections	Absolute structure: Flack (1983), 1245 Friedel pairs
130 parameters	Flack parameter: 0.09 (10)
1 restraint

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	0.6260 (6)	0.3230 (3)	0.7737 (3)	0.0472 (8)
H1A	0.5852	0.2242	0.7487	0.057*
H1B	0.7793	0.3481	0.7406	0.057*
C2	0.4110 (5)	0.4171 (3)	0.7057 (3)	0.0387 (6)
C3	0.2613 (6)	0.4950 (3)	0.7758 (3)	0.0442 (7)
H3	0.2941	0.4919	0.8691	0.053*
C4	0.0597 (6)	0.5793 (4)	0.7084 (4)	0.0505 (8)
H4	−0.0375	0.6326	0.7577	0.061*
C5	0.0047 (6)	0.5840 (3)	0.5736 (3)	0.0501 (8)
H5	−0.1313	0.6396	0.531	0.06*
C6	0.1509 (5)	0.5057 (3)	0.4954 (3)	0.0409 (7)
C7	0.0961 (7)	0.5081 (3)	0.3544 (4)	0.0529 (9)
H7	−0.0423	0.561	0.3104	0.063*
C8	0.2421 (8)	0.4342 (4)	0.2810 (4)	0.0591 (9)
H8	0.2043	0.4373	0.1877	0.071*
C9	0.4484 (7)	0.3540 (4)	0.3465 (4)	0.0571 (9)
H9	0.5481	0.3039	0.2962	0.069*
C10	0.5064 (6)	0.3476 (3)	0.4826 (4)	0.0486 (8)
H10	0.6454	0.2933	0.5238	0.058*
C11	0.3593 (5)	0.4221 (3)	0.5631 (3)	0.0395 (6)
N1	0.6799 (6)	0.3336 (3)	0.9219 (3)	0.0495 (7)
H1C	0.708 (8)	0.418 (5)	0.955 (4)	0.069 (12)*
H1D	0.835 (7)	0.288 (3)	0.957 (3)	0.046 (9)*
H1E	0.546 (8)	0.298 (4)	0.957 (4)	0.065 (12)*
Cl1	0.79683 (14)	0.66025 (10)	1.01767 (8)	0.04759 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0375 (17)	0.0408 (16)	0.062 (2)	0.0020 (14)	0.0058 (15)	0.0015 (15)
C2	0.0302 (14)	0.0284 (13)	0.0570 (18)	0.0001 (11)	0.0074 (13)	0.0007 (12)
C3	0.0404 (16)	0.0394 (15)	0.0531 (19)	0.0020 (13)	0.0096 (14)	0.0017 (13)
C4	0.0441 (18)	0.0429 (16)	0.067 (2)	0.0118 (14)	0.0171 (16)	0.0025 (16)
C5	0.0401 (17)	0.0416 (16)	0.068 (2)	0.0088 (14)	0.0095 (16)	0.0115 (15)
C6	0.0335 (16)	0.0328 (13)	0.056 (2)	−0.0042 (11)	0.0083 (13)	0.0032 (13)
C7	0.050 (2)	0.0468 (18)	0.060 (2)	−0.0081 (15)	0.0048 (16)	0.0078 (16)
C8	0.069 (2)	0.056 (2)	0.053 (2)	−0.0188 (19)	0.0126 (18)	−0.0009 (17)
C9	0.061 (2)	0.0467 (18)	0.069 (2)	−0.0062 (16)	0.0242 (19)	−0.0125 (17)
C10	0.0424 (18)	0.0398 (16)	0.064 (2)	0.0014 (13)	0.0104 (16)	−0.0065 (15)
C11	0.0308 (14)	0.0318 (13)	0.0561 (18)	−0.0066 (11)	0.0087 (13)	−0.0008 (13)
N1	0.0387 (16)	0.0421 (16)	0.0640 (19)	0.0032 (13)	0.0002 (14)	0.0029 (14)
Cl1	0.0426 (3)	0.0466 (3)	0.0527 (4)	−0.0046 (4)	0.0067 (3)	−0.0113 (4)

C1—N1	1.480 (5)	C6—C11	1.425 (4)
C1—C2	1.506 (4)	C7—C8	1.363 (5)
C1—H1A	0.97	C7—H7	0.93
C1—H1B	0.97	C8—C9	1.393 (5)
C2—C3	1.374 (4)	C8—H8	0.93
C2—C11	1.421 (4)	C9—C10	1.357 (5)
C3—C4	1.402 (4)	C9—H9	0.93
C3—H3	0.93	C10—C11	1.418 (4)
C4—C5	1.344 (5)	C10—H10	0.93
C4—H4	0.93	N1—H1C	0.86 (4)
C5—C6	1.416 (4)	N1—H1D	0.94 (3)
C5—H5	0.93	N1—H1E	0.92 (4)
C6—C7	1.405 (5)
N1—C1—C2	114.3 (3)	C8—C7—C6	121.1 (3)
N1—C1—H1A	108.7	C8—C7—H7	119.4
C2—C1—H1A	108.7	C6—C7—H7	119.4
N1—C1—H1B	108.7	C7—C8—C9	119.6 (3)
C2—C1—H1B	108.7	C7—C8—H8	120.2
H1A—C1—H1B	107.6	C9—C8—H8	120.2
C3—C2—C11	119.2 (3)	C10—C9—C8	121.2 (3)
C3—C2—C1	122.7 (3)	C10—C9—H9	119.4
C11—C2—C1	118.1 (3)	C8—C9—H9	119.4
C2—C3—C4	120.9 (3)	C9—C10—C11	121.3 (3)
C2—C3—H3	119.6	C9—C10—H10	119.4
C4—C3—H3	119.6	C11—C10—H10	119.4
C5—C4—C3	121.0 (3)	C10—C11—C2	123.2 (3)
C5—C4—H4	119.5	C10—C11—C6	117.3 (3)
C3—C4—H4	119.5	C2—C11—C6	119.5 (3)
C4—C5—C6	121.0 (3)	C1—N1—H1C	116 (3)
C4—C5—H5	119.5	C1—N1—H1D	110.2 (19)
C6—C5—H5	119.5	H1C—N1—H1D	101 (3)
C7—C6—C5	122.0 (3)	C1—N1—H1E	111 (2)
C7—C6—C11	119.5 (3)	H1C—N1—H1E	106 (4)
C5—C6—C11	118.4 (3)	H1D—N1—H1E	113 (3)
N1—C1—C2—C3	−6.2 (4)	C8—C9—C10—C11	0.1 (5)
N1—C1—C2—C11	175.2 (3)	C9—C10—C11—C2	179.2 (3)
C11—C2—C3—C4	−0.1 (5)	C9—C10—C11—C6	−1.0 (5)
C1—C2—C3—C4	−178.8 (3)	C3—C2—C11—C10	178.7 (3)
C2—C3—C4—C5	1.2 (5)	C1—C2—C11—C10	−2.6 (4)
C3—C4—C5—C6	−0.9 (5)	C3—C2—C11—C6	−1.1 (4)
C4—C5—C6—C7	179.5 (3)	C1—C2—C11—C6	177.6 (3)
C4—C5—C6—C11	−0.4 (5)	C7—C6—C11—C10	1.6 (4)
C5—C6—C7—C8	178.7 (3)	C5—C6—C11—C10	−178.5 (3)
C11—C6—C7—C8	−1.4 (4)	C7—C6—C11—C2	−178.5 (3)
C6—C7—C8—C9	0.4 (5)	C5—C6—C11—C2	1.4 (4)
C7—C8—C9—C10	0.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Cl1	0.86 (5)	2.37 (5)	3.226 (3)	172 (3)
N1—H1D···Cl1i	0.94 (4)	2.27 (4)	3.187 (3)	164 (3)
N1—H1E···Cl1ii	0.92 (4)	2.29 (4)	3.172 (3)	161 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯Cl1	0.86 (5)	2.37 (5)	3.226 (3)	172 (3)
N1—H1D⋯Cl1i	0.94 (4)	2.27 (4)	3.187 (3)	164 (3)
N1—H1E⋯Cl1ii	0.92 (4)	2.29 (4)	3.172 (3)	161 (3)

Symmetry codes: (i) ; (ii) .