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The asymmetric unit of the title compound, C7H10N+·Cl-·H2O, contains a 2-methyl­anilinium cation, a chloride anion and one mol­ecule of water. The crystal structure consists of alternating layers of hydro­phobic and hydro­philic zones of o-toluidine along the c axis. The water mol­ecules and the chloride anions are sandwiched between these layers. A large number of cation-anion, cation-water and water-anion hydrogen bonds result in a two-dimensional network which reinforces the cohesion of the ionic structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037117/hg2263sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037117/hg2263Isup2.hkl
Contains datablock I

CCDC reference: 660193

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.141
  • Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT245_ALERT_2_C U(iso) H1W Smaller than U(eq) O1W by ... 0.04 AngSq PLAT245_ALERT_2_C U(iso) H2W Smaller than U(eq) O1W by ... 0.04 AngSq
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: Benslimane and Dembri: synthesis, Bouacida, Merazig and Beghidja: structure determination and preparation of paper, Ouahab: data collection and structure determination.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

Comment top

Organic–inorganic hybrid materials have attracted a great deal of attention over the past few decades (Koutselas et al., 1996; Mitzi et al., 1998; Mayer et al., 1999; Mazeaud et al., 2000) because of their ionic, electrical, magnetic and optical properties (Hill, 1998; Kagan et al., 1999; Raptopoulou et al., 2002).

The methylanilinium is already reported with nitrate (Benali-Cherif et al., 2007), picrate (Muthamizhchelvan et al., 2005) and dihydrogenphosphate (Fábry et al., 2002).

In the course of our ongoing program related to the synthesis and structural study of hybrid compounds based on tin and amines (Bouacida et al., 2007; Bouacida et al., 2006; Bouacida et al., 2005a; Bouacida et al., 2005b; Bouacida et al., 2005c), we report here the synthesis and crystal structure of 2-Methylanilinium chloride monohydrate, (I).

The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The asymmetric unit of the title compound consist of a2-methylanilinium cation, a chloride anion and one molecule of water. The crystal structure consists of alternating layers of 2-methylanilinium. The chloride ions and water molecules are sandwiched between layers of hydrophobic and hydrophilic zones of 2-methylanilinium(Fig. 2). In this structure, three types of classical hydrogen bonds are observed, viz.cation–anion, cation–water and water-anion, with the N atom of the cation and O of water acting as donors (Fig.3, Table 1).

Related literature top

For related literature, see: Benali-Cherif et al. (2007); Bouacida et al. (2005a, 2005b, 2005c, 2006, 2007); Fábry et al. (2002); Hill (1998); Kagan et al. (1999); Koutselas et al. (1996); Mayer et al. (1999); Mazeaud et al. (2000); Mitzi et al. (1998); Muthamizhchelvan et al. (2005); Raptopoulou et al. (2002).

Experimental top

Crystals were grown from aqueous solutions that were obtained by dissolving 1 mmol SnCl2·2H2O, 2 mmol 2-methylaniline in hydrochloric acid. The solutions were slowly evaporated to dryness for a couple of weeks. Some red crystals were carefully isolated under polarizing microscope for analysis by X-ray diffraction.

Refinement top

All H atoms were localized in Fourier maps but introduced in calculated positions and treated as riding on their parent C and N atoms with C—H = 0.93–0.96 Å and N—H = 0.89 Å and Uiso(H) =1.2–1.5 (carrier atom), except for H1W and H2W were located in a difference Fourier map and refined isotropically.

Structure description top

Organic–inorganic hybrid materials have attracted a great deal of attention over the past few decades (Koutselas et al., 1996; Mitzi et al., 1998; Mayer et al., 1999; Mazeaud et al., 2000) because of their ionic, electrical, magnetic and optical properties (Hill, 1998; Kagan et al., 1999; Raptopoulou et al., 2002).

The methylanilinium is already reported with nitrate (Benali-Cherif et al., 2007), picrate (Muthamizhchelvan et al., 2005) and dihydrogenphosphate (Fábry et al., 2002).

In the course of our ongoing program related to the synthesis and structural study of hybrid compounds based on tin and amines (Bouacida et al., 2007; Bouacida et al., 2006; Bouacida et al., 2005a; Bouacida et al., 2005b; Bouacida et al., 2005c), we report here the synthesis and crystal structure of 2-Methylanilinium chloride monohydrate, (I).

The molecular geometry and the atom-numbering scheme of (I) are shown in Fig. 1. The asymmetric unit of the title compound consist of a2-methylanilinium cation, a chloride anion and one molecule of water. The crystal structure consists of alternating layers of 2-methylanilinium. The chloride ions and water molecules are sandwiched between layers of hydrophobic and hydrophilic zones of 2-methylanilinium(Fig. 2). In this structure, three types of classical hydrogen bonds are observed, viz.cation–anion, cation–water and water-anion, with the N atom of the cation and O of water acting as donors (Fig.3, Table 1).

For related literature, see: Benali-Cherif et al. (2007); Bouacida et al. (2005a, 2005b, 2005c, 2006, 2007); Fábry et al. (2002); Hill (1998); Kagan et al. (1999); Koutselas et al. (1996); Mayer et al. (1999); Mazeaud et al. (2000); Mitzi et al. (1998); Muthamizhchelvan et al. (2005); Raptopoulou et al. (2002).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed down the C axis, showing layers of molecule.
[Figure 3] Fig. 3. A view of the ionic stacking, showing the hydrogen bonds as dashed lines.
2-Methylanilinium chloride monohydrate top
Crystal data top
C7H10N+·Cl·H2OF(000) = 344
Mr = 161.63Dx = 1.205 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5072 reflections
a = 8.1871 (5) Åθ = 1.0–25.0°
b = 7.4046 (4) ŵ = 0.37 mm1
c = 14.7415 (5) ÅT = 173 K
β = 94.600 (4)°Prism, red
V = 890.78 (8) Å30.10 × 0.08 × 0.06 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
Rint = 0.016
Graphite monochromatorθmax = 25.0°, θmin = 2.5°
φ and ω scansh = 99
2895 measured reflectionsk = 88
1508 independent reflectionsl = 1616
1203 reflections with I > 2σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.141 w = 1/[σ2(Fo2) + (0.0907P)2 + 0.0493P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
1508 reflectionsΔρmax = 0.27 e Å3
100 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.116 (18)
Crystal data top
C7H10N+·Cl·H2OV = 890.78 (8) Å3
Mr = 161.63Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.1871 (5) ŵ = 0.37 mm1
b = 7.4046 (4) ÅT = 173 K
c = 14.7415 (5) Å0.10 × 0.08 × 0.06 mm
β = 94.600 (4)°
Data collection top
Nonius KappaCCD
diffractometer
1203 reflections with I > 2σ(I)
2895 measured reflectionsRint = 0.016
1508 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.27 e Å3
1508 reflectionsΔρmin = 0.19 e Å3
100 parameters
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

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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.2974 (2)0.3362 (2)0.44034 (12)0.0545 (6)
C10.1203 (3)0.3087 (3)0.44239 (15)0.0524 (7)
C20.0621 (3)0.2488 (3)0.52207 (15)0.0606 (8)
C30.1035 (3)0.2160 (4)0.5250 (2)0.0759 (10)
C40.2066 (3)0.2427 (4)0.4493 (2)0.0818 (11)
C50.1480 (4)0.3034 (4)0.3699 (2)0.0791 (11)
C60.0189 (3)0.3381 (3)0.36395 (16)0.0643 (9)
C70.0874 (4)0.4069 (5)0.27810 (17)0.0932 (11)
O1W0.4013 (3)0.0788 (3)0.32831 (14)0.0917 (9)
Cl10.50523 (7)0.17364 (8)0.13149 (3)0.0628 (3)
H1A0.345650.324730.496340.0817*
H1B0.316280.446330.419370.0817*
H1C0.337830.254190.404090.0817*
H20.133600.230520.573500.0727*
H30.144230.175830.578590.0910*
H40.317940.219780.451200.0981*
H50.220820.321740.319040.0949*
H7A0.149650.514820.291570.1397*
H7B0.001030.432970.233280.1397*
H7C0.157150.316440.254980.1397*
H1W0.424 (3)0.098 (3)0.2830 (17)0.0500*
H2W0.442 (3)0.008 (4)0.3448 (16)0.0500*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0624 (12)0.0549 (11)0.0463 (10)0.0004 (8)0.0053 (8)0.0004 (7)
C10.0586 (13)0.0458 (12)0.0527 (12)0.0065 (9)0.0035 (9)0.0069 (8)
C20.0653 (15)0.0590 (14)0.0581 (13)0.0029 (11)0.0096 (10)0.0041 (10)
C30.0702 (18)0.0810 (18)0.0789 (18)0.0004 (13)0.0212 (13)0.0104 (13)
C40.0610 (16)0.088 (2)0.097 (2)0.0064 (14)0.0095 (14)0.0251 (16)
C50.0688 (17)0.0814 (19)0.0839 (19)0.0181 (13)0.0132 (14)0.0224 (13)
C60.0764 (17)0.0592 (14)0.0559 (14)0.0133 (11)0.0042 (11)0.0084 (9)
C70.117 (2)0.104 (2)0.0556 (16)0.0058 (19)0.0109 (14)0.0130 (14)
O1W0.142 (2)0.0740 (13)0.0642 (12)0.0295 (13)0.0406 (12)0.0094 (10)
Cl10.0757 (5)0.0641 (5)0.0492 (4)0.0006 (3)0.0085 (3)0.0042 (2)
Geometric parameters (Å, º) top
O1W—H1W0.72 (3)C4—C51.376 (4)
O1W—H2W0.76 (3)C5—C61.400 (4)
N1—C11.467 (3)C6—C71.513 (4)
N1—H1B0.8900C2—H20.9300
N1—H1A0.8900C3—H30.9300
N1—H1C0.8900C4—H40.9300
C1—C21.376 (3)C5—H50.9300
C1—C61.386 (3)C7—H7C0.9600
C2—C31.381 (3)C7—H7A0.9600
C3—C41.359 (4)C7—H7B0.9600
Cl1···N1i3.2015 (17)C6···C2v3.578 (3)
Cl1···O1W3.167 (2)C7···H1C2.8800
Cl1···N1ii3.1736 (18)C7···H1B2.7000
Cl1···O1Wiii3.141 (2)H1A···Cl1iv2.2900
Cl1···H2Wiii2.42 (3)H1A···H22.2600
Cl1···H1W2.45 (2)H1B···C72.7000
Cl1···H1Aii2.2900H1B···Cl1iii2.3900
Cl1···H1Bi2.3900H1B···H7A2.2900
O1W···C13.412 (3)H1C···H7C2.5900
O1W···Cl13.167 (2)H1C···H2W2.3200
O1W···N12.704 (3)H1C···C72.8800
O1W···Cl1i3.141 (2)H1C···H1W2.2900
O1W···H7C2.8100H1C···O1W1.8200
O1W···H1C1.8200H1W···H1C2.2900
N1···O1W2.704 (3)H1W···Cl12.45 (2)
N1···Cl1iv3.1736 (18)H2···H1A2.2600
N1···Cl1iii3.2015 (17)H2W···Cl1i2.42 (3)
N1···H7C2.8800H2W···H1C2.3200
N1···H7A2.7600H5···H7B2.4200
C1···O1W3.412 (3)H7A···H1B2.2900
C1···C3v3.556 (4)H7A···N12.7600
C2···C6v3.578 (3)H7B···H52.4200
C2···C3vi3.533 (4)H7C···O1W2.8100
C3···C2vi3.533 (4)H7C···N12.8800
C3···C1v3.556 (4)H7C···H1C2.5900
H1W—O1W—H2W109 (3)C5—C6—C7122.9 (2)
H1B—N1—H1C109.00C3—C2—H2120.00
C1—N1—H1C109.00C1—C2—H2120.00
C1—N1—H1A109.00C2—C3—H3120.00
C1—N1—H1B110.00C4—C3—H3120.00
H1A—N1—H1B109.00C5—C4—H4120.00
H1A—N1—H1C109.00C3—C4—H4120.00
C2—C1—C6122.5 (2)C4—C5—H5119.00
N1—C1—C6119.2 (2)C6—C5—H5119.00
N1—C1—C2118.2 (2)C6—C7—H7B109.00
C1—C2—C3119.4 (2)C6—C7—H7C109.00
C2—C3—C4119.7 (3)C6—C7—H7A109.00
C3—C4—C5120.7 (3)H7A—C7—H7C109.00
C4—C5—C6121.5 (3)H7B—C7—H7C109.00
C1—C6—C5116.2 (2)H7A—C7—H7B109.00
C1—C6—C7120.9 (2)
N1—C1—C2—C3177.9 (2)C1—C2—C3—C40.2 (4)
C6—C1—C2—C30.1 (4)C2—C3—C4—C50.5 (4)
N1—C1—C6—C5177.9 (2)C3—C4—C5—C60.6 (5)
N1—C1—C6—C73.1 (3)C4—C5—C6—C10.3 (4)
C2—C1—C6—C50.0 (3)C4—C5—C6—C7179.3 (3)
C2—C1—C6—C7179.0 (2)
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1/2, z1/2; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z+1/2; (v) x, y+1, z+1; (vi) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1iv0.89002.29003.1736 (18)170.00
N1—H1B···Cl1iii0.89002.39003.2015 (17)152.00
N1—H1C···O1W0.89001.82002.704 (3)175.00
O1W—H1W···Cl10.72 (3)2.45 (2)3.167 (2)177.9 (14)
O1W—H2W···Cl1i0.76 (3)2.42 (3)3.141 (2)161 (3)
Symmetry codes: (i) x+1, y1/2, z+1/2; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC7H10N+·Cl·H2O
Mr161.63
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)8.1871 (5), 7.4046 (4), 14.7415 (5)
β (°) 94.600 (4)
V3)890.78 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.37
Crystal size (mm)0.10 × 0.08 × 0.06
Data collection
DiffractometerNonius KappaCCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2895, 1508, 1203
Rint0.016
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.141, 1.11
No. of reflections1508
No. of parameters100
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.19

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl1i0.89002.29003.1736 (18)170.00
N1—H1B···Cl1ii0.89002.39003.2015 (17)152.00
N1—H1C···O1W0.89001.82002.704 (3)175.00
O1W—H1W···Cl10.72 (3)2.45 (2)3.167 (2)177.9 (14)
O1W—H2W···Cl1iii0.76 (3)2.42 (3)3.141 (2)161 (3)
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y1/2, z+1/2.
 

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