(1-Naphthyl­meth­yl)ammonium chloride

Salimi, A.R.; Azizpoor Fard, M.; Eshtiagh-Hosseini, H.; Amini, M.M.; Khavasi, H.R.

doi:10.1107/S160053681000334X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o509

doi:10.1107/S160053681000334X

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(1-Naphthylmethyl)ammonium chloride

Ali R. Salimi,^a Mahmood Azizpoor Fard,^b Hossein Eshtiagh-Hosseini,^a Mostafa M. Amini ^b and Hamid R. Khavasi ^b ^*

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 917791436, Iran, and ^bDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran
^*Correspondence e-mail: h-khavasi@sbu.ac.ir

(Received 4 January 2010; accepted 27 January 2010; online 3 February 2010)

The reaction of 1-naphthylmethylamine and hydrochloric acid in a 1:1 molar ratio resulted in the formation of the 1:1 proton-transfer compound, C₁₁H₁₂N⁺·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_r = 193.67
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.100
S = 1.19
2677 reflections
130 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 245 Friedel pairs
Flack parameter: 0.09 (10)

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) $[-x+2, y-{\script{1\over 2}}, -z+2]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+2]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

1-naphthylmethylamine has been recognized as a suitable agent in the synthesis of proton-transfer systems (Sada et al., 2004). We report here the synthesis and characterization of the title salt, 1-naphthylmethylammonium chloride. The structure shows the presence of a 1-naphthylmethylammonium species that arises from the protonation of the amine group (Fig. 1). Hydrogen bonds play a very important role in the structure. As it is clear from Figure 2, chloride atoms engage in three hydrogen bonds with the amine group in which the chloride is in the center of triangle from three H atoms from three different cations.

Related literature top

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

Experimental top

A solution of 2.5 ml of 2M hydrochloric acid was added to a solution of 5 mmol 1-naphthalenemethylamine (0.73 ml) in 30 ml pyridine. The resulting solution was stirred at 373 K for 5 h and at ambient temperature for 24 h. A pale brown solution resulted. After drying the remaining brown solid was dissolved in pure methanol. X-ray quality crystals were obtained by slow evaporation at room temperature.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); 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).

Figures top

	Fig. 1. The molecular staucture with the atom-numbering scheme. Displacement ellipsoids are drawn at 30% probability level.
	Fig. 2. A packing diagram of the title compound in thr b-direction. Hydrogen bonds are shown as dashed lines.

(1-Naphthylmethyl)ammonium chloride top

Crystal data top

C₁₁H₁₂N⁺·Cl⁻	F(000) = 204
M_r = 193.67	D_x = 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

Data collection top

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

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0155P)² + 0.2107P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.054	(Δ/σ)_max = 0.002
wR(F²) = 0.100	Δρ_max = 0.28 e Å⁻³
S = 1.19	Δρ_min = −0.17 e Å⁻³
2677 reflections	Absolute structure: Flack (1983), 1245 Friedel pairs
130 parameters	Absolute structure parameter: 0.09 (10)
1 restraint

Crystal data top

C₁₁H₁₂N⁺·Cl⁻	V = 496.55 (12) Å³
M_r = 193.67	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.3395 (7) Å	µ = 0.34 mm⁻¹
b = 9.3355 (15) Å	T = 298 K
c = 10.1432 (13) Å	0.35 × 0.13 × 0.11 mm
β = 100.864 (10)°

Data collection top

Stoe IPDS II diffractometer	2677 independent reflections
Absorption correction: numerical (X-RED and X-SHAPE; Stoe & Cie, 2005)	2098 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.968	R_int = 0.065
5801 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.100	Δρ_max = 0.28 e Å⁻³
S = 1.19	Δρ_min = −0.17 e Å⁻³
2677 reflections	Absolute structure: Flack (1983), 1245 Friedel pairs
130 parameters	Absolute structure parameter: 0.09 (10)
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, y−1/2, −z+2; (ii) −x+1, y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N⁺·Cl⁻
M_r	193.67
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	5.3395 (7), 9.3355 (15), 10.1432 (13)
β (°)	100.864 (10)
V (Å³)	496.55 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.35 × 0.13 × 0.11

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Numerical (X-RED and X-SHAPE; Stoe & Cie, 2005)
T_min, T_max	0.952, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	5801, 2677, 2098
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.100, 1.19
No. of reflections	2677
No. of parameters	130
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.17
Absolute structure	Flack (1983), 1245 Friedel pairs
Absolute structure parameter	0.09 (10)

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) −x+2, y−1/2, −z+2; (ii) −x+1, y−1/2, −z+2.

Acknowledgements

The authors wish to acknowledge Shahid Beheshti University, GC, for financial support.

References

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