Crystal structure of (2-chloro­eth­yl)[2-(methyl­sulfan­yl)benz­yl]ammonium chloride

Raghavendra Kumar, P.; Shailesh, U.; Palakshamurthy, B.S.

doi:10.1107/S2056989015008221

research communications

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 71| Part 6| June 2015| Pages 621-623

doi:10.1107/S2056989015008221

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Crystal structure of (2-chloroethyl)[2-(methylsulfanyl)benzyl]ammonium chloride

P. Raghavendra Kumar,^a ^* Upereti Shailesh ^b and B. S. Palakshamurthy ^c

^aDepartment of Chemistry, UCS, Tumkur University, Tumkur 572 103, Karnataka, India, ^bDepartment of Chemistry, Indian Institute of Technology, Delhi, New Delhi 110 016, India, and ^cDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: raghukp1@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 31 January 2015; accepted 26 April 2015; online 13 May 2015)

In the title molecular salt, C₁₀H₁₅ClNS⁺·Cl⁻, the cation is [R′R"NH₂]⁺, where R′ is 2-MeS-C₆H₄CH₂– and R" is –CH₂CH₂Cl, and the anion is Cl⁻. In the cation, the N atom is protonated with sp³-hybridization and with a tetrahedral geometry. In the crystal, the anions are connected to the cations through two pairs of N—H⋯Cl hydrogen bonds, generating a four-centred inversion dimer with an R₄²(8) ring motif.

Keywords: crystal structure; chloroethyl; S and N donors; amine hydrochloride; N—H⋯Cl hydrogen bonds.

CCDC reference: 299500

1. Chemical context

Chloroethyl-functionalized derivatives containing S- and N-donor sites are used for the preparation of (S, N, S/Se/Te/P/As/Sb)-type tridentate hybrid ligands by nucleophilic substitution of the chloro (Cl⁻) group by RS⁻, ArSe⁻, ArTe⁻, Ph₂P⁻, Ar₂As⁻ (Kumar et al., 2008a ; Singh et al., 1999 ; Singh & Singh, 2010 , 2012 ; Kumar et al., 2008b ). Metal complexes of this type of hybrid ligand are important and have found applications as catalysts in organic synthesis (Singh et al., 2013 ). Keeping this in mind, it was thought worthwhile to synthesise and characterise the title molecular salt. We report herein on its synthesis, by chlorination of 2-(2-methylthio)benzylamino)ethanol using thionyl chloride, and on its crystal structure.

2. Structural commentary

In the cation of the title molecular salt (Fig. 1), the –CH₂–N⁺H₂–CH₂–CH₂–Cl substituent has an extended conformation with all of the non-H atoms lying in a plane [maximum deviation = 0.032 (4) Å for atom C8]. The N1 atom is protonated with sp³-hybridization and has a tetrahedral geometry. The S1 atom lies in the plane of the benzene ring to which it is attached while the methyl C10 atom is displaced from the plane of the benzene ring by 1.773 (5) Å.

Figure 1
The molecular structure of the title molecular salt, showing the atom labelling. The displacement ellipsoids are drawn at the 50% probability level.

The title molecular salt was also characterised by NMR and FT–IR spectroscopy. In the proton NMR spectrum, the signals for the NCH₂ and CH₂Cl protons gave two triplets at 3.25 and 3.9 p.p.m., respectively. The [C₁₀H₁₅ClSN]⁺ cation is a secondary ammonium ion in which the N atom is protonated and hence undergoes sp³ hybridization, resulting in a tetrahedral geometry around the N atom. This was confirmed by NMR as the 〉NH₂⁺ protons are highly deshielded and are observed as a broad singlet at 10.03 p.p.m. In the FT–IR spectrum of title salt, the N–H stretching band was observed at 1569 cm⁻¹.

3. Supramolecular features

In the crystal, the cation and anion are connected through two pairs of N—H⋯Cl hydrogen bonds. These hydrogen bonds result in the formation of four-centred inversion dimers with an $[R_{4}^{2}]$ (8) ring motif (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Cl2	0.89	2.21	3.090 (3)	169
N1—H1A⋯Cl2ⁱ	0.89	2.32	3.163 (3)	158
Symmetry code: (i) -x+1, -y, -z.

Figure 2
The crystal packing of the title molecular salt, viewed along the a axis. The N—H⋯Cl hydrogen bonds are shown as dashed lines (see Table 1

for details).

4. Database survey

A search of the Cambridge Structural Database (Version 5.36; Groom & Allen, 2014 ) found no hits for similar compounds. However, tridentate (S, N, S/Se/Te)-type ligands containing the cationic part of the title salt and their Pd^II and Ru^II complexes have been synthesised and structurally characterized (Kumar et al., 2008a; Singh & Singh, 2012; Singh et al., 2012 ).

5. Synthesis and crystallization

The synthesis of the title compound is illustrated in Fig. 3. 2-(2-Methylthio)benzylamino)ethanol (2 g, 10 mmol) was dissolved in 20 ml of dry chloroform and the solution was cooled in an ice bath. Freshly distilled SOCl₂ (3 ml, 40 mmol) dissolved in 20 ml of dry chloroform was added to it dropwise over a period of 15 min. When the addition was complete, the temperature of the reaction mixture was increased slowly and the mixture was stirred under reflux for 6 h. Thereafter, the reaction mixture was cooled and concentrated to 10 ml on a rotary evaporator, giving a light-brown solid. The solid was dissolved in 10 ml of methanol, boiled with a pinch of activated charcoal and filtered. The filtrate was treated with 20 ml of diethyl ether. It gave a white crystalline product (caution: eye and skin irritant), which was filtered, washed with diethyl ether (10 ml × 4) and dried between the folds of filter paper. Colourless prisms of the title compound were grown in ethanol by slow evaporation of the solvent (yield: 70%; m.p.: 413 K; Λ_M = 3.0 cm² mol⁻¹ ohm⁻¹. Elemental analysis, found (calc.): C, 47.87 (47.68), H, 5.95 (5.99), N, 5.68 (5.55) %; ¹H NMR (CDCl₃, 298 K): δ (vs TMS): 2.55 (s, 3H, SCH₃), 3.25 (t, J = 6.09 Hz, 2H, H₁), 3.9 (t, J = 6,6 Hz, 2H, H₂), 4.94 (s, 2H, H₃), 7.26 (t, J = 6.96 Hz, 1H, H₈), 7.34–7.46 (m, 2H, H_6,7), 7.72–7.74 (d, J = 7.5 Hz, 1H, H₉), 10.03 (bs, 2H, NH₂⁺). ¹³C{¹H} NMR (CDCl₃, 298 K): δ (vs TMS): 16.85 (SCH₃), 48.17 (C₂), 49.27 (C₁), 57.12 (C₃), 126.26 (C₆), 127.89 (C₇) , 128.87 (C₄), 130.25 (C₈), 131.50 (C₉), 138.95 (C₅). FT–IR (KBr, cm⁻¹): 3415 (s), 1569 (b) (N–H), 1590 (C–N), 763 (C–S).

Figure 3
The synthesis of the title molecular salt.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydrogen atoms attached to atom N1 were located in a difference Fourier map. In the final cycles of refinement they were included in calculated positions, as were the C-bound H atoms, and treated as riding atoms: N—H = 0.89 Å, C—H = 0.93–0.97 Å with U_iso(H) = 1.5U_eq(C) for methyl H atoms and = 1.2U_eq(N,C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₁₅ClNS⁺·Cl⁻
M_r	252.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.5717 (10), 11.8058 (17), 16.201 (2)
β (°)	97.374 (3)
V (Å³)	1246.5 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.65
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.839, 0.881
No. of measured, independent and observed [I > 2σ(I)] reflections	9002, 2255, 1584
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.158, 1.04
No. of reflections	2255
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.23
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 299500

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S2056989015008221/su5075sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015008221/su5075Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015008221/su5075Isup3.cml

checkCIF report

Chemical context top

Chloroethyl-functionalized derivatives containing S- and N-donor sites are used for the preparation of (S, N, S/Se/Te/P/As/Sb)-type tridentate hybrid ligands by nucleophilic substitution of the chloro (Cl^-) group by RS^-, ArSe^-, ArTe^- , Ph₂P^-, Ar₂As^- (Kumar et al., 2008a; Singh et al., 1999; Singh & Singh, 2010, 2012; Kumar et al., 2008b). Metal complexes of this type of hybrid ligand are important and have found applications as catalysts in organic synthesis (Singh et al., 2013). Keeping this in mind, it was thought worthwhile to synthesise and characterise the title molecular salt. We report herein on its synthesis, by chlorination of 2-(2-methylthio)benzylamino)ethanol using thionyl chloride, and on its crystal structure.

Structural commentary top

In the cation of the title molecular salt, the –CH₂–N⁺H₂–CH₂–CH₂–Cl substituent has an extended conformation with all of the non-H atoms lying in a plane [maximum deviation = 0.032 (4) Å for atom C8]. The N1 atom is protonated with sp³-hybridization and has a tetrahedral geometry. The S1 atom lies in the plane of the benzene ring to which it is attached while the methyl C10 atom is displaced from the plane of the benzene ring by 1.773 (5) Å.

Supramolecular features top

In the crystal, the cation and anion are connected through two pairs of N—H···Cl hydrogen bonds. These hydrogen bonds result in the formation of four-centred inversion dimers with an R₄²(8) ring motif (Table 1 and Fig. 2).

Database survey top

A search of the Cambridge Structural Database (Version 5.36; Groom & Allen, 2014) found no hits for similar compounds. However, tridentate (S, N, S/Se/Te)-type ligands containing the cationic part of the title salt and their Pd^II and Ru^II complexes have been synthesised and structurally characterized (Kumar et al., 2008a; Singh & Singh, 2012; Singh et al., 2012).

Synthesis and crystallization top

The synthesis of the title compound is illustrated in Fig. 3. 2-(2-Methylthio)benzylamino)ethanol (2 g, 10 mmol) was dissolved in 20 ml of dry chloroform and the solution was cooled in an ice bath. Freshly distilled SOCl₂ (3 ml, 40 mmol) dissolved in 20 ml of dry chloroform was added to it dropwise over a period of 15 min. When the addition was complete, the temperature of reaction mixture was increased slowly and the mixture was stirred under reflux for 6 h. Thereafter, the reaction mixture was cooled and concentrated to 10 ml on a rotary evaporator, giving a light-brown solid. The solid was dissolved in 10 ml of methanol, boiled with a pinch of activated charcoal and filtered. The filtrate was treated with 20 ml of diethyl ether. It gave a white crystalline product (caution: eye and skin irritant), which was filtered, washed with diethyl ether (10 ml × 4) and dried between the folds of filter paper. Colourless prisms of the title compound were grown in ethanol by slow evaporation of the solvent (yield: 70%; m.p.: 413 K; Λ_M = 3.0 cm² mol^-1 ohm^-1. Elemental analysis, found (calc.): C, 47.87 (47.68), H, 5.95 (5.99), N, 5.68 (5.55) %; ¹H NMR (CDCl₃, 298 K): δ (vs TMS): 2.55 (s, 3H, SCH₃), 3.25 (t, J = 6.09 Hz, 2H, H₁), 3.9 (t, J = 6,6 Hz, 2H, H₂), 4.94 (s, 2H, H₃), 7.26 (t, J = 6.96 Hz, 1H, H₈), 7.34–7.46 (m, 2H, H_6,7), 7.72–7.74 (d, J = 7.5 Hz, 1H, H₉), 10.03 (bs, 2H, NH₂⁺). ¹³C{¹H} NMR (CDCl₃, 298 K): δ (vs TMS): 16.85 (SCH₃), 48.17 (C₂), 49.27 (C₁), 57.12 (C₃), 126.26 (C₆), 127.89 (C₇ ), 128.87 (C₄), 130.25 (C₈), 131.50 (C₉), 138.95 (C₅). FT–IR (KBr, cm^-1): 3415 (s), 1569 (b) (N–H), 1590 (C–N), 763 (C–S).

Refinement top

Related literature top

For related literature, see: Groom & Allen (2014); Kumar et al. (2008a, 2008b); Singh & Singh (2010, 2012); Singh et al. (1999, 2013); Singh, Das, Kumar & Singh (2012).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecular salt, showing the atom labelling. The displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title molecular salt, viewed along the a axis. The N—H···Cl hydrogen bonds are shown as dashed lines (see Table 1 for details).
	Fig. 3. The synthesis of the title molecular salt.

(2-Chloroethyl)[2-(methylsulfanyl)benzyl]ammonium chloride top

Crystal data top

C₁₀H₁₅ClNS⁺·Cl⁻	F(000) = 528
M_r = 252.19	D_x = 1.344 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.5717 (10) Å	θ = 2.1–25.0°
b = 11.8058 (17) Å	µ = 0.65 mm⁻¹
c = 16.201 (2) Å	T = 298 K
β = 97.374 (3)°	Prism, colourless
V = 1246.5 (3) Å³	0.28 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1584 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.100
phi and ω scans	θ_max = 25.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −7→7
T_min = 0.839, T_max = 0.881	k = −14→14
9002 measured reflections	l = −19→19
2255 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.065	H-atom parameters constrained
wR(F²) = 0.158	w = 1/[σ²(F_o²) + (0.0727P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2255 reflections	Δρ_max = 0.50 e Å⁻³
128 parameters	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₁₅ClNS⁺·Cl⁻	V = 1246.5 (3) Å³
M_r = 252.19	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.5717 (10) Å	µ = 0.65 mm⁻¹
b = 11.8058 (17) Å	T = 298 K
c = 16.201 (2) Å	0.28 × 0.24 × 0.20 mm
β = 97.374 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2255 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	1584 reflections with I > 2σ(I)
T_min = 0.839, T_max = 0.881	R_int = 0.100
9002 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.04	Δρ_max = 0.50 e Å⁻³
2255 reflections	Δρ_min = −0.23 e Å⁻³
128 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.73384 (17)	−0.10230 (10)	0.26820 (8)	0.0632 (4)
Cl1	0.2925 (2)	0.37387 (9)	0.02280 (9)	0.0769 (4)
N1	0.3518 (5)	0.0518 (2)	0.10476 (19)	0.0437 (8)
H1A	0.2751	0.0208	0.0613	0.052*
H1B	0.4827	0.0411	0.0980	0.052*
C1	0.3504 (6)	−0.1317 (3)	0.1757 (2)	0.0442 (9)
C2	0.5336 (6)	−0.1815 (3)	0.2109 (2)	0.0443 (9)
C4	0.4120 (7)	−0.3622 (4)	0.1571 (3)	0.0615 (12)
H4	0.4340	−0.4393	0.1503	0.074*
C3	0.5612 (7)	−0.2969 (3)	0.2011 (3)	0.0557 (11)
H3	0.6828	−0.3307	0.2247	0.067*
C5	0.2319 (8)	−0.3142 (4)	0.1233 (3)	0.0675 (13)
H5	0.1301	−0.3584	0.0940	0.081*
C6	0.2013 (7)	−0.1992 (4)	0.1330 (3)	0.0612 (12)
H6	0.0777	−0.1669	0.1102	0.073*
C8	0.3102 (6)	0.1754 (3)	0.1051 (3)	0.0497 (10)
H8A	0.4013	0.2113	0.1493	0.060*
H8B	0.1701	0.1884	0.1157	0.060*
C7	0.3103 (6)	−0.0073 (3)	0.1812 (2)	0.0489 (10)
H7A	0.1683	0.0047	0.1896	0.059*
H7B	0.3968	0.0241	0.2287	0.059*
C9	0.3421 (8)	0.2266 (3)	0.0230 (3)	0.0657 (13)
H9A	0.2511	0.1906	−0.0212	0.079*
H9B	0.4822	0.2136	0.0125	0.079*
C10	0.6669 (8)	−0.1210 (4)	0.3711 (3)	0.0762 (15)
H10A	0.5336	−0.0892	0.3741	0.114*
H10B	0.7662	−0.0834	0.4104	0.114*
H10C	0.6651	−0.2003	0.3840	0.114*
Cl2	0.80532 (15)	0.04958 (9)	0.07270 (6)	0.0537 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0557 (7)	0.0679 (8)	0.0632 (8)	−0.0149 (6)	−0.0034 (6)	0.0005 (6)
Cl1	0.0879 (9)	0.0413 (7)	0.1012 (10)	0.0074 (6)	0.0111 (7)	0.0136 (6)
N1	0.0465 (19)	0.0362 (18)	0.0467 (19)	0.0002 (14)	−0.0010 (15)	−0.0050 (15)
C1	0.053 (2)	0.038 (2)	0.042 (2)	0.0005 (19)	0.0068 (19)	0.0023 (17)
C2	0.050 (2)	0.041 (2)	0.040 (2)	0.0010 (18)	−0.0013 (18)	0.0014 (18)
C4	0.088 (4)	0.035 (2)	0.060 (3)	0.005 (2)	0.005 (3)	0.005 (2)
C3	0.064 (3)	0.042 (2)	0.058 (3)	0.011 (2)	−0.003 (2)	0.004 (2)
C5	0.088 (4)	0.050 (3)	0.058 (3)	−0.018 (3)	−0.011 (3)	0.001 (2)
C6	0.054 (3)	0.058 (3)	0.066 (3)	−0.005 (2)	−0.013 (2)	0.005 (2)
C8	0.049 (2)	0.032 (2)	0.067 (3)	0.0023 (18)	0.006 (2)	−0.001 (2)
C7	0.056 (2)	0.043 (2)	0.048 (2)	0.0082 (19)	0.007 (2)	0.0038 (18)
C9	0.085 (3)	0.037 (2)	0.071 (3)	0.002 (2)	−0.003 (3)	0.004 (2)
C10	0.084 (4)	0.084 (4)	0.058 (3)	−0.020 (3)	−0.001 (3)	−0.014 (3)
Cl2	0.0499 (6)	0.0577 (7)	0.0524 (6)	0.0044 (5)	0.0020 (5)	−0.0074 (5)

Geometric parameters (Å, º) top

S1—C2	1.776 (4)	C3—H3	0.9300
S1—C10	1.792 (5)	C5—C6	1.384 (6)
Cl1—C9	1.768 (4)	C5—H5	0.9300
N1—C7	1.477 (5)	C6—H6	0.9300
N1—C8	1.485 (5)	C8—C9	1.501 (6)
N1—H1A	0.8900	C8—H8A	0.9700
N1—H1B	0.8900	C8—H8B	0.9700
C1—C6	1.378 (5)	C7—H7A	0.9700
C1—C2	1.394 (5)	C7—H7B	0.9700
C1—C7	1.496 (5)	C9—H9A	0.9700
C2—C3	1.386 (5)	C9—H9B	0.9700
C4—C5	1.362 (6)	C10—H10A	0.9600
C4—C3	1.373 (6)	C10—H10B	0.9600
C4—H4	0.9300	C10—H10C	0.9600

C2—S1—C10	99.7 (2)	N1—C8—C9	110.2 (3)
C7—N1—C8	114.0 (3)	N1—C8—H8A	109.6
C7—N1—H1A	108.8	C9—C8—H8A	109.6
C8—N1—H1A	108.8	N1—C8—H8B	109.6
C7—N1—H1B	108.8	C9—C8—H8B	109.6
C8—N1—H1B	108.8	H8A—C8—H8B	108.1
H1A—N1—H1B	107.6	N1—C7—C1	111.1 (3)
C6—C1—C2	118.8 (4)	N1—C7—H7A	109.4
C6—C1—C7	118.6 (4)	C1—C7—H7A	109.4
C2—C1—C7	122.6 (3)	N1—C7—H7B	109.4
C3—C2—C1	119.1 (4)	C1—C7—H7B	109.4
C3—C2—S1	118.6 (3)	H7A—C7—H7B	108.0
C1—C2—S1	122.3 (3)	C8—C9—Cl1	110.5 (3)
C5—C4—C3	120.1 (4)	C8—C9—H9A	109.5
C5—C4—H4	120.0	Cl1—C9—H9A	109.5
C3—C4—H4	120.0	C8—C9—H9B	109.5
C4—C3—C2	121.1 (4)	Cl1—C9—H9B	109.5
C4—C3—H3	119.5	H9A—C9—H9B	108.1
C2—C3—H3	119.5	S1—C10—H10A	109.5
C4—C5—C6	119.6 (4)	S1—C10—H10B	109.5
C4—C5—H5	120.2	H10A—C10—H10B	109.5
C6—C5—H5	120.2	S1—C10—H10C	109.5
C1—C6—C5	121.3 (4)	H10A—C10—H10C	109.5
C1—C6—H6	119.3	H10B—C10—H10C	109.5
C5—C6—H6	119.3

C6—C1—C2—C3	0.7 (6)	C3—C4—C5—C6	0.6 (7)
C7—C1—C2—C3	−178.2 (4)	C2—C1—C6—C5	−1.2 (6)
C6—C1—C2—S1	−179.2 (3)	C7—C1—C6—C5	177.8 (4)
C7—C1—C2—S1	1.9 (5)	C4—C5—C6—C1	0.5 (7)
C10—S1—C2—C3	−87.1 (4)	C7—N1—C8—C9	−175.9 (3)
C10—S1—C2—C1	92.8 (4)	C8—N1—C7—C1	178.6 (3)
C5—C4—C3—C2	−1.1 (7)	C6—C1—C7—N1	−81.3 (5)
C1—C2—C3—C4	0.4 (6)	C2—C1—C7—N1	97.7 (4)
S1—C2—C3—C4	−179.7 (3)	N1—C8—C9—Cl1	179.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cl2	0.89	2.21	3.090 (3)	169
N1—H1A···Cl2ⁱ	0.89	2.32	3.163 (3)	158

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cl2	0.89	2.21	3.090 (3)	169
N1—H1A···Cl2ⁱ	0.89	2.32	3.163 (3)	158

Symmetry code: (i) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₅ClNS⁺·Cl⁻
M_r	252.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	6.5717 (10), 11.8058 (17), 16.201 (2)
β (°)	97.374 (3)
V (Å³)	1246.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2013)
T_min, T_max	0.839, 0.881
No. of measured, independent and observed [I > 2σ(I)] reflections	9002, 2255, 1584
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.158, 1.04
No. of reflections	2255
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.23

Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2013), SHELXS97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Acknowledgements

PRK thanks Professor Ajai K. Singh of IIT Delhi, India, for his valuable guidance during his PhD studies. BSP thanks Dr H. C. Devarajegowda, Department of Physics, Yuvarajas College (constituent), University of Mysore, for his support.

References

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Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. Web of Science CrossRef CAS Google Scholar
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Volume 71| Part 6| June 2015| Pages 621-623

doi:10.1107/S2056989015008221

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (2-chloro­eth­yl)[2-(methyl­sulfan­yl)benz­yl]ammonium chloride

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Crystal structure of (2-chloroethyl)[2-(methylsulfanyl)benzyl]ammonium chloride

3. Supramolecular features