3,4-Dimethyl­anilinium chloride monohydrate

Bouacida, S.; Belhouas, R.; Kechout, H.; Merazig, H.; Bénard-Rocherullé, P.

doi:10.1107/S1600536809006072

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Pages o628-o629

doi:10.1107/S1600536809006072

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3,4-Dimethylanilinium chloride monohydrate

Sofiane Bouacida,^a,^b ^* Ratiba Belhouas,^c Habiba Kechout,^b Hocine Merazig ^b and Patricia Bénard-Rocherullé ^d

^aDépartement de Chimie, Faculté des Sciences et Sciences de l'Ingénieur, Université A. Mira de Béjaia, Route Targua Ouzmour, 06000 Béjaia, Algeria, ^bLaboratoire de Chimie Moléculaire du Contrôle de l'Environnement et des Mesures Physico-Chimiques, Faculté des Sciences Exactes, Département de Chimie, Université Mentouri, Constantine 25000, Algeria, ^cFaculté de Chimie, USTHB, BP32, El-Alia, Bab-Ezzouar, Alger, Algeria, and ^dSciences Chimiques de Rennes (UMR CNRS 6226), Université de Rennes 1, Avenue du Général Leclerc, 35042 Rennes Cedex, France
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 11 February 2009; accepted 19 February 2009; online 28 February 2009)

The crystal structure of the title compound, C₈H₁₂N⁺·Cl⁻·H₂O, consists of hydrophobic layers of dimethylanilinium cations parallel to the bc plane alternated by hydrophilic layers of chloride anions and water molecules. The layers are linked by N—H⋯O and N—H⋯Cl hydrogen bonds involving the ammonium groups of the cations. The cohesion of the ionic structure is further stabilized by O—H⋯Cl hydrogen-bonding interactions.

Related literature

For crystal structures containing the dimethylanilinium cation, see: Bouacida (2008 ); Singh et al. (2002 ); Singh et al. (1995a ,b ); Linden et al. (1995 ); Fábry et al. (2001 , 2002 ). For the crystal structures of related protonated amines, see: Bouacida et al. (2005a ,b ,c , 2006 , 2007 ); Benslimane et al. (2007 ); Rademeyer (2004a ,b ).

Experimental

Crystal data

C₈H₁₂N⁺·Cl⁻·H₂O
M_r = 175.65
Orthorhombic, P c a 2₁
a = 18.230 (18) Å
b = 6.7854 (14) Å
c = 7.916 (2) Å
V = 979.2 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 295 K
0.1 × 0.04 × 0.02 mm

Data collection

Enraf–Nonius KappaCCD diffractometer
Absorption correction: none
10115 measured reflections
2181 independent reflections
1403 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.109
S = 1.15
2181 reflections
109 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 976 Friedel pairs
Flack parameter: 0.01 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1W	0.89	1.87	2.754 (5)	174
N1—H1B⋯Cl1ⁱ	0.89	2.30	3.177 (4)	167
N1—H1C⋯Cl1ⁱⁱ	0.89	2.31	3.181 (4)	167
O1W—H1W⋯Cl1	0.80 (6)	2.43 (6)	3.217 (5)	174 (7)
O1W—H2W⋯Cl1ⁱⁱⁱ	0.81 (5)	2.36 (5)	3.174 (5)	176 (2)
Symmetry codes: (i) $[-x, -y+1, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1; (iii) $[-x, -y+2, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997); and SCALEPACK program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg et al., 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809006072/rz2296sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809006072/rz2296Isup2.hkl

checkCIF report

Comment top

The title compound, was prepared as part of our ongoing studies of hydrogen-bonding interactions in the crystal structure of protonated amines (Bouacida et al., 2005a,b,c; Bouacida et al., 2006; Benslimane et al., 2007; Bouacida et al., 2007). Structures containing the dimethylanilinium cation have been already reported with tin chloride (Bouacida, 2008), sulfate (Singh et al., 2002), nitrate and perchlorate (Singh et al., 1995a,b), chloride (Linden et al., 1995), and dihydrogenphosphate (Fabry et al., 2001; Fábry et al., 2002).

The molecular structure of the title compound is illustrated in Fig. 1. A l l bond distances and angles are within the ranges of accepted values. The amino N atom is protonated as in other aminoacids (Bouacida et al., 2006; Rademeyer 2004a,b). A diagram of the layered crystal packing of title compound is shown in Fig. 2, in which the cations are arranged to form zigzag layers parallel the ab plane, with the chloride ions and water molecules located between these layers. The structure may be also described as formed by hydrophobic layers parallel to the bc plane of dimethylanilinium cations alternated by hydrophilic layers of chloride anions and water molecules. In this structure, three types of classical hydrogen bonds are observed, viz. cation–anion, cation–water and water–anion (Fig. 3, Table 1). All three ammonium H atoms are involved in hydrogen bonds. These interactions link the molecules within the layers and also link the layers together, forming a three-dimensional network and reinforcing the cohesion of the ionic structure.

Related literature top

For crystal structures containing the dimethylanilinium cation, see: Bouacida (2008); Singh et al. (2002); Singh et al. (1995a,b); Linden et al. (1995); Fábry et al. (2001, 2002). For the crystal structures of related protonated amines, see: Bouacida et al. (2005a,b,c, 2006, 2007); Benslimane et al. (2007); Rademeyer (2004a,b).

Experimental top

An aqueous solution of SnCl₂.2H₂O (1 mmol) and 3,4-dimethylaniline (2 mmol) in hydrochloric acid was slowly evaporated to dryness for two weeks. White single crystals of the title compound were carefully isolated under polarizing microscope for X-ray diffraction analysis

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg et al., 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The structure of the title compound with the atomic labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A diagram of the layered crystal packing in the title comound, viewed down the a axis.
	Fig. 3. Crystal packing of the title compound viewed down the b axis. H bonds are shown as dashed lines.

3,4-Dimethylanilinium chloride monohydrate top

Crystal data top

C₈H₁₂N⁺·Cl⁻·H₂O	F(000) = 376
M_r = 175.65	D_x = 1.191 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 9401 reflections
a = 18.230 (18) Å	θ = 3.7–27.5°
b = 6.7854 (14) Å	µ = 0.34 mm⁻¹
c = 7.916 (2) Å	T = 295 K
V = 979.2 (10) Å³	Stalk, white
Z = 4	0.1 × 0.04 × 0.02 mm

Data collection top

Enraf–Nonius KappaCCD diffractometer	R_int = 0.078
CCD rotation images, thick slices scans	θ_max = 27.5°, θ_min = 3.7°
10115 measured reflections	h = −23→23
2181 independent reflections	k = −8→8
1403 reflections with I > 2σ(I)	l = −10→9

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) + (0.0307P)² + 0.3106P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.059	(Δ/σ)_max < 0.001
wR(F²) = 0.109	Δρ_max = 0.20 e Å⁻³
S = 1.15	Δρ_min = −0.22 e Å⁻³
2181 reflections	Absolute structure: Flack (1983), 976 Friedel pairs
109 parameters	Absolute structure parameter: 0.01 (11)
1 restraint

Crystal data top

C₈H₁₂N⁺·Cl⁻·H₂O	V = 979.2 (10) Å³
M_r = 175.65	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 18.230 (18) Å	µ = 0.34 mm⁻¹
b = 6.7854 (14) Å	T = 295 K
c = 7.916 (2) Å	0.1 × 0.04 × 0.02 mm

Data collection top

Enraf–Nonius KappaCCD diffractometer	1403 reflections with I > 2σ(I)
10115 measured reflections	R_int = 0.078
2181 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	Δρ_max = 0.20 e Å⁻³
S = 1.15	Δρ_min = −0.22 e Å⁻³
2181 reflections	Absolute structure: Flack (1983), 976 Friedel pairs
109 parameters	Absolute structure parameter: 0.01 (11)
1 restraint

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	U_iso*/U_eq
N1	0.06494 (14)	0.5513 (4)	0.2268 (4)	0.0433 (10)
C1	0.14146 (17)	0.4809 (5)	0.2159 (4)	0.0395 (11)
C2	0.1556 (2)	0.3036 (6)	0.1426 (5)	0.0447 (12)
C3	0.22856 (19)	0.2362 (5)	0.1269 (4)	0.0430 (13)
C4	0.28449 (18)	0.3555 (5)	0.1893 (5)	0.0444 (11)
C5	0.2677 (2)	0.5332 (6)	0.2641 (5)	0.0517 (14)
C6	0.1959 (2)	0.5966 (5)	0.2776 (5)	0.0467 (12)
C7	0.2432 (3)	0.0413 (6)	0.0454 (6)	0.0670 (19)
C8	0.3636 (2)	0.2894 (7)	0.1744 (7)	0.0693 (16)
O1W	0.0447 (3)	0.8297 (5)	0.4757 (4)	0.0818 (13)
Cl1	0.04002 (5)	0.77733 (12)	0.87943 (11)	0.0507 (3)
H1A	0.06154	0.64300	0.30678	0.0650*
H1B	0.03559	0.45076	0.25217	0.0650*
H1C	0.05158	0.60253	0.12795	0.0650*
H2	0.11712	0.22655	0.10264	0.0534*
H5	0.30525	0.61175	0.30623	0.0620*
H6	0.18505	0.71675	0.32834	0.0559*
H7A	0.27619	0.05896	−0.04794	0.1007*
H7B	0.19792	−0.01381	0.00532	0.1007*
H7C	0.26488	−0.04643	0.12637	0.1007*
H8A	0.39537	0.39319	0.21227	0.1038*
H8B	0.37436	0.25867	0.05870	0.1038*
H8C	0.37112	0.17444	0.24296	0.1038*
H1W	0.046 (3)	0.824 (9)	0.576 (7)	0.1038*
H2W	0.022 (3)	0.927 (8)	0.447 (7)	0.1038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0455 (16)	0.0461 (17)	0.0383 (18)	0.0025 (13)	−0.0007 (14)	0.0048 (14)
C1	0.0384 (18)	0.044 (2)	0.0361 (19)	0.0062 (16)	0.0041 (17)	0.0089 (18)
C2	0.051 (2)	0.043 (2)	0.040 (2)	−0.0076 (17)	0.0008 (19)	0.0070 (18)
C3	0.060 (3)	0.039 (2)	0.0300 (17)	0.0022 (17)	0.004 (2)	0.0089 (17)
C4	0.047 (2)	0.051 (2)	0.0353 (19)	0.0013 (17)	0.0013 (19)	0.010 (2)
C5	0.052 (2)	0.051 (2)	0.052 (3)	−0.0056 (18)	−0.006 (2)	0.002 (2)
C6	0.049 (2)	0.045 (2)	0.046 (2)	0.0024 (18)	−0.0018 (19)	0.0034 (18)
C7	0.097 (4)	0.048 (3)	0.056 (3)	0.012 (2)	0.008 (3)	0.000 (2)
C8	0.052 (2)	0.082 (3)	0.074 (3)	0.009 (2)	0.007 (3)	0.011 (3)
O1W	0.127 (3)	0.066 (2)	0.0523 (18)	0.037 (2)	−0.004 (2)	−0.0054 (17)
Cl1	0.0555 (4)	0.0492 (5)	0.0475 (4)	0.0042 (4)	−0.0028 (6)	0.0044 (6)

Geometric parameters (Å, º) top

O1W—H2W	0.81 (5)	C4—C5	1.378 (6)
O1W—H1W	0.80 (6)	C5—C6	1.382 (5)
N1—C1	1.477 (4)	C2—H2	0.9300
N1—H1A	0.8900	C5—H5	0.9300
N1—H1C	0.8900	C6—H6	0.9300
N1—H1B	0.8900	C7—H7B	0.9600
C1—C2	1.360 (5)	C7—H7C	0.9600
C1—C6	1.356 (5)	C7—H7A	0.9600
C2—C3	1.412 (5)	C8—H8C	0.9600
C3—C7	1.496 (6)	C8—H8A	0.9600
C3—C4	1.392 (5)	C8—H8B	0.9600
C4—C8	1.515 (5)

Cl1···O1W	3.217 (5)	C8···H7A	2.8400
Cl1···N1ⁱ	3.181 (4)	H1A···H2W	2.3400
Cl1···N1ⁱⁱ	3.177 (4)	H1A···O1W	1.8700
Cl1···O1Wⁱⁱⁱ	3.174 (5)	H1A···H6	2.3100
Cl1···H1W	2.43 (6)	H1A···H1W	2.4800
Cl1···H1Cⁱ	2.3100	H1B···Cl1^vi	2.3000
Cl1···H1Bⁱⁱ	2.3000	H1B···H2	2.4300
Cl1···H5^iv	3.0900	H1C···Cl1^vii	2.3100
Cl1···H2Wⁱⁱⁱ	2.36 (5)	H1W···H1A	2.4800
O1W···Cl1^v	3.174 (5)	H1W···Cl1	2.43 (6)
O1W···N1	2.754 (5)	H2···H1B	2.4300
O1W···Cl1	3.217 (5)	H2···H7B	2.3300
O1W···H1A	1.8700	H2W···Cl1^v	2.36 (5)
O1W···H6	2.9100	H2W···H1A	2.3400
N1···Cl1^vi	3.177 (4)	H5···H8A	2.3300
N1···Cl1^vii	3.181 (4)	H5···Cl1^viii	3.0900
N1···O1W	2.754 (5)	H6···H1A	2.3100
C3···C5^viii	3.509 (6)	H6···C7^xi	3.0800
C3···C4^viii	3.565 (6)	H6···O1W	2.9100
C4···C3^iv	3.565 (6)	H7A···H8B	2.4000
C4···C7^iv	3.570 (7)	H7A···C8	2.8400
C5···C3^iv	3.509 (6)	H7A···C3^viii	2.8400
C7···C4^viii	3.570 (7)	H7A···C4^viii	3.1000
C3···H7A^iv	2.8400	H7B···H2	2.3300
C4···H7A^iv	3.1000	H7C···C8	2.9300
C5···H7C^ix	3.0500	H7C···C5^xii	3.0500
C6···H7C^ix	2.9800	H7C···C6^xii	2.9800
C7···H8B	2.8100	H8A···H5	2.3300
C7···H8C	2.9500	H8B···C7	2.8100
C7···H6^x	3.0800	H8B···H7A	2.4000
C8···H7C	2.9300	H8C···C7	2.9500

H1W—O1W—H2W	110 (6)	C3—C2—H2	120.00
H1A—N1—H1B	109.00	C1—C2—H2	120.00
H1A—N1—H1C	109.00	C4—C5—H5	120.00
C1—N1—H1B	109.00	C6—C5—H5	119.00
C1—N1—H1C	109.00	C5—C6—H6	121.00
H1B—N1—H1C	109.00	C1—C6—H6	120.00
C1—N1—H1A	109.00	C3—C7—H7A	109.00
N1—C1—C2	119.3 (3)	C3—C7—H7B	109.00
C2—C1—C6	121.8 (3)	H7A—C7—H7B	109.00
N1—C1—C6	118.9 (3)	H7A—C7—H7C	109.00
C1—C2—C3	120.2 (3)	C3—C7—H7C	110.00
C2—C3—C4	118.1 (3)	H7B—C7—H7C	109.00
C2—C3—C7	119.5 (4)	C4—C8—H8B	109.00
C4—C3—C7	122.4 (3)	C4—C8—H8C	109.00
C3—C4—C8	119.8 (3)	C4—C8—H8A	109.00
C5—C4—C8	120.3 (3)	H8A—C8—H8C	109.00
C3—C4—C5	119.9 (3)	H8B—C8—H8C	109.00
C4—C5—C6	121.1 (3)	H8A—C8—H8B	110.00
C1—C6—C5	119.0 (3)

N1—C1—C2—C3	178.3 (3)	C2—C3—C4—C8	−179.7 (4)
C6—C1—C2—C3	−0.9 (6)	C7—C3—C4—C5	−179.6 (4)
N1—C1—C6—C5	−178.5 (3)	C7—C3—C4—C8	0.5 (6)
C2—C1—C6—C5	0.6 (6)	C3—C4—C5—C6	−0.4 (6)
C1—C2—C3—C4	0.4 (5)	C8—C4—C5—C6	179.5 (4)
C1—C2—C3—C7	−179.8 (4)	C4—C5—C6—C1	0.0 (6)
C2—C3—C4—C5	0.2 (5)

Symmetry codes: (i) x, y, z+1; (ii) −x, −y+1, z+1/2; (iii) −x, −y+2, z+1/2; (iv) −x+1/2, y, z+1/2; (v) −x, −y+2, z−1/2; (vi) −x, −y+1, z−1/2; (vii) x, y, z−1; (viii) −x+1/2, y, z−1/2; (ix) x, y+1, z; (x) −x+1/2, y−1, z−1/2; (xi) −x+1/2, y+1, z+1/2; (xii) x, y−1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1W	0.8900	1.8700	2.754 (5)	174.00
N1—H1B···Cl1^vi	0.8900	2.3000	3.177 (4)	167.00
N1—H1C···Cl1^vii	0.8900	2.3100	3.181 (4)	167.00
O1W—H1W···Cl1	0.80 (6)	2.43 (6)	3.217 (5)	174 (7)
O1W—H2W···Cl1^v	0.81 (5)	2.36 (5)	3.174 (5)	176 (2)

Symmetry codes: (v) −x, −y+2, z−1/2; (vi) −x, −y+1, z−1/2; (vii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	C₈H₁₂N⁺·Cl⁻·H₂O
M_r	175.65
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	295
a, b, c (Å)	18.230 (18), 6.7854 (14), 7.916 (2)
V (Å³)	979.2 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.1 × 0.04 × 0.02

Data collection
Diffractometer	Enraf–Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10115, 2181, 1403
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.109, 1.15
No. of reflections	2181
No. of parameters	109
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)	0.20, −0.22
Absolute structure	Flack (1983), 976 Friedel pairs
Absolute structure parameter	0.01 (11)

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg et al., 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1W	0.8900	1.8700	2.754 (5)	174.00
N1—H1B···Cl1ⁱ	0.8900	2.3000	3.177 (4)	167.00
N1—H1C···Cl1ⁱⁱ	0.8900	2.3100	3.181 (4)	167.00
O1W—H1W···Cl1	0.80 (6)	2.43 (6)	3.217 (5)	174 (7)
O1W—H2W···Cl1ⁱⁱⁱ	0.81 (5)	2.36 (5)	3.174 (5)	176 (2)

Symmetry codes: (i) −x, −y+1, z−1/2; (ii) x, y, z−1; (iii) −x, −y+2, z−1/2.

Acknowledgements

The authors are grateful to Dr Thierry Roisnel, Centre de Diffractométrie X (CDIFX) de Rennes, Université de Rennes 1, France, for the data collection facilities. SB thanks Université A. Mira de Béjaia, Algéria, for financial support.

References

Benslimane, M., Merazig, H., Bouacida, S., Denbri, S., Beghidja, A. & Ouahab, L. (2007). Acta Cryst. E63, o3682–o3683. Web of Science CSD CrossRef IUCr Journals Google Scholar
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