Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037117/hg2263sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037117/hg2263Isup2.hkl |
CCDC reference: 660193
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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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
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).
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.
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.
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).
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).
C7H10N+·Cl−·H2O | F(000) = 344 |
Mr = 161.63 | Dx = 1.205 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5072 reflections |
a = 8.1871 (5) Å | θ = 1.0–25.0° |
b = 7.4046 (4) Å | µ = 0.37 mm−1 |
c = 14.7415 (5) Å | T = 173 K |
β = 94.600 (4)° | Prism, red |
V = 890.78 (8) Å3 | 0.10 × 0.08 × 0.06 mm |
Z = 4 |
Nonius KappaCCD diffractometer | Rint = 0.016 |
Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
φ and ω scans | h = −9→9 |
2895 measured reflections | k = −8→8 |
1508 independent reflections | l = −16→16 |
1203 reflections with I > 2σ(I) |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H 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 reflections | Δρmax = 0.27 e Å−3 |
100 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.116 (18) |
C7H10N+·Cl−·H2O | V = 890.78 (8) Å3 |
Mr = 161.63 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.1871 (5) Å | µ = 0.37 mm−1 |
b = 7.4046 (4) Å | T = 173 K |
c = 14.7415 (5) Å | 0.10 × 0.08 × 0.06 mm |
β = 94.600 (4)° |
Nonius KappaCCD diffractometer | 1203 reflections with I > 2σ(I) |
2895 measured reflections | Rint = 0.016 |
1508 independent reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.141 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.27 e Å−3 |
1508 reflections | Δρmin = −0.19 e Å−3 |
100 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.2974 (2) | 0.3362 (2) | 0.44034 (12) | 0.0545 (6) | |
C1 | 0.1203 (3) | 0.3087 (3) | 0.44239 (15) | 0.0524 (7) | |
C2 | 0.0621 (3) | 0.2488 (3) | 0.52207 (15) | 0.0606 (8) | |
C3 | −0.1035 (3) | 0.2160 (4) | 0.5250 (2) | 0.0759 (10) | |
C4 | −0.2066 (3) | 0.2427 (4) | 0.4493 (2) | 0.0818 (11) | |
C5 | −0.1480 (4) | 0.3034 (4) | 0.3699 (2) | 0.0791 (11) | |
C6 | 0.0189 (3) | 0.3381 (3) | 0.36395 (16) | 0.0643 (9) | |
C7 | 0.0874 (4) | 0.4069 (5) | 0.27810 (17) | 0.0932 (11) | |
O1W | 0.4013 (3) | 0.0788 (3) | 0.32831 (14) | 0.0917 (9) | |
Cl1 | 0.50523 (7) | 0.17364 (8) | 0.13149 (3) | 0.0628 (3) | |
H1A | 0.34565 | 0.32473 | 0.49634 | 0.0817* | |
H1B | 0.31628 | 0.44633 | 0.41937 | 0.0817* | |
H1C | 0.33783 | 0.25419 | 0.40409 | 0.0817* | |
H2 | 0.13360 | 0.23052 | 0.57350 | 0.0727* | |
H3 | −0.14423 | 0.17583 | 0.57859 | 0.0910* | |
H4 | −0.31794 | 0.21978 | 0.45120 | 0.0981* | |
H5 | −0.22082 | 0.32174 | 0.31904 | 0.0949* | |
H7A | 0.14965 | 0.51482 | 0.29157 | 0.1397* | |
H7B | −0.00103 | 0.43297 | 0.23328 | 0.1397* | |
H7C | 0.15715 | 0.31644 | 0.25498 | 0.1397* | |
H1W | 0.424 (3) | 0.098 (3) | 0.2830 (17) | 0.0500* | |
H2W | 0.442 (3) | −0.008 (4) | 0.3448 (16) | 0.0500* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0624 (12) | 0.0549 (11) | 0.0463 (10) | 0.0004 (8) | 0.0053 (8) | −0.0004 (7) |
C1 | 0.0586 (13) | 0.0458 (12) | 0.0527 (12) | 0.0065 (9) | 0.0035 (9) | −0.0069 (8) |
C2 | 0.0653 (15) | 0.0590 (14) | 0.0581 (13) | 0.0029 (11) | 0.0096 (10) | −0.0041 (10) |
C3 | 0.0702 (18) | 0.0810 (18) | 0.0789 (18) | −0.0004 (13) | 0.0212 (13) | −0.0104 (13) |
C4 | 0.0610 (16) | 0.088 (2) | 0.097 (2) | 0.0064 (14) | 0.0095 (14) | −0.0251 (16) |
C5 | 0.0688 (17) | 0.0814 (19) | 0.0839 (19) | 0.0181 (13) | −0.0132 (14) | −0.0224 (13) |
C6 | 0.0764 (17) | 0.0592 (14) | 0.0559 (14) | 0.0133 (11) | −0.0042 (11) | −0.0084 (9) |
C7 | 0.117 (2) | 0.104 (2) | 0.0556 (16) | 0.0058 (19) | −0.0109 (14) | 0.0130 (14) |
O1W | 0.142 (2) | 0.0740 (13) | 0.0642 (12) | 0.0295 (13) | 0.0406 (12) | 0.0094 (10) |
Cl1 | 0.0757 (5) | 0.0641 (5) | 0.0492 (4) | 0.0006 (3) | 0.0085 (3) | −0.0042 (2) |
O1W—H1W | 0.72 (3) | C4—C5 | 1.376 (4) |
O1W—H2W | 0.76 (3) | C5—C6 | 1.400 (4) |
N1—C1 | 1.467 (3) | C6—C7 | 1.513 (4) |
N1—H1B | 0.8900 | C2—H2 | 0.9300 |
N1—H1A | 0.8900 | C3—H3 | 0.9300 |
N1—H1C | 0.8900 | C4—H4 | 0.9300 |
C1—C2 | 1.376 (3) | C5—H5 | 0.9300 |
C1—C6 | 1.386 (3) | C7—H7C | 0.9600 |
C2—C3 | 1.381 (3) | C7—H7A | 0.9600 |
C3—C4 | 1.359 (4) | C7—H7B | 0.9600 |
Cl1···N1i | 3.2015 (17) | C6···C2v | 3.578 (3) |
Cl1···O1W | 3.167 (2) | C7···H1C | 2.8800 |
Cl1···N1ii | 3.1736 (18) | C7···H1B | 2.7000 |
Cl1···O1Wiii | 3.141 (2) | H1A···Cl1iv | 2.2900 |
Cl1···H2Wiii | 2.42 (3) | H1A···H2 | 2.2600 |
Cl1···H1W | 2.45 (2) | H1B···C7 | 2.7000 |
Cl1···H1Aii | 2.2900 | H1B···Cl1iii | 2.3900 |
Cl1···H1Bi | 2.3900 | H1B···H7A | 2.2900 |
O1W···C1 | 3.412 (3) | H1C···H7C | 2.5900 |
O1W···Cl1 | 3.167 (2) | H1C···H2W | 2.3200 |
O1W···N1 | 2.704 (3) | H1C···C7 | 2.8800 |
O1W···Cl1i | 3.141 (2) | H1C···H1W | 2.2900 |
O1W···H7C | 2.8100 | H1C···O1W | 1.8200 |
O1W···H1C | 1.8200 | H1W···H1C | 2.2900 |
N1···O1W | 2.704 (3) | H1W···Cl1 | 2.45 (2) |
N1···Cl1iv | 3.1736 (18) | H2···H1A | 2.2600 |
N1···Cl1iii | 3.2015 (17) | H2W···Cl1i | 2.42 (3) |
N1···H7C | 2.8800 | H2W···H1C | 2.3200 |
N1···H7A | 2.7600 | H5···H7B | 2.4200 |
C1···O1W | 3.412 (3) | H7A···H1B | 2.2900 |
C1···C3v | 3.556 (4) | H7A···N1 | 2.7600 |
C2···C6v | 3.578 (3) | H7B···H5 | 2.4200 |
C2···C3vi | 3.533 (4) | H7C···O1W | 2.8100 |
C3···C2vi | 3.533 (4) | H7C···N1 | 2.8800 |
C3···C1v | 3.556 (4) | H7C···H1C | 2.5900 |
H1W—O1W—H2W | 109 (3) | C5—C6—C7 | 122.9 (2) |
H1B—N1—H1C | 109.00 | C3—C2—H2 | 120.00 |
C1—N1—H1C | 109.00 | C1—C2—H2 | 120.00 |
C1—N1—H1A | 109.00 | C2—C3—H3 | 120.00 |
C1—N1—H1B | 110.00 | C4—C3—H3 | 120.00 |
H1A—N1—H1B | 109.00 | C5—C4—H4 | 120.00 |
H1A—N1—H1C | 109.00 | C3—C4—H4 | 120.00 |
C2—C1—C6 | 122.5 (2) | C4—C5—H5 | 119.00 |
N1—C1—C6 | 119.2 (2) | C6—C5—H5 | 119.00 |
N1—C1—C2 | 118.2 (2) | C6—C7—H7B | 109.00 |
C1—C2—C3 | 119.4 (2) | C6—C7—H7C | 109.00 |
C2—C3—C4 | 119.7 (3) | C6—C7—H7A | 109.00 |
C3—C4—C5 | 120.7 (3) | H7A—C7—H7C | 109.00 |
C4—C5—C6 | 121.5 (3) | H7B—C7—H7C | 109.00 |
C1—C6—C5 | 116.2 (2) | H7A—C7—H7B | 109.00 |
C1—C6—C7 | 120.9 (2) | ||
N1—C1—C2—C3 | −177.9 (2) | C1—C2—C3—C4 | 0.2 (4) |
C6—C1—C2—C3 | 0.1 (4) | C2—C3—C4—C5 | −0.5 (4) |
N1—C1—C6—C5 | 177.9 (2) | C3—C4—C5—C6 | 0.6 (5) |
N1—C1—C6—C7 | −3.1 (3) | C4—C5—C6—C1 | −0.3 (4) |
C2—C1—C6—C5 | 0.0 (3) | C4—C5—C6—C7 | −179.3 (3) |
C2—C1—C6—C7 | 179.0 (2) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+1/2, z−1/2; (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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1iv | 0.8900 | 2.2900 | 3.1736 (18) | 170.00 |
N1—H1B···Cl1iii | 0.8900 | 2.3900 | 3.2015 (17) | 152.00 |
N1—H1C···O1W | 0.8900 | 1.8200 | 2.704 (3) | 175.00 |
O1W—H1W···Cl1 | 0.72 (3) | 2.45 (2) | 3.167 (2) | 177.9 (14) |
O1W—H2W···Cl1i | 0.76 (3) | 2.42 (3) | 3.141 (2) | 161 (3) |
Symmetry codes: (i) −x+1, y−1/2, −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 formula | C7H10N+·Cl−·H2O |
Mr | 161.63 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 173 |
a, b, c (Å) | 8.1871 (5), 7.4046 (4), 14.7415 (5) |
β (°) | 94.600 (4) |
V (Å3) | 890.78 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.10 × 0.08 × 0.06 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2895, 1508, 1203 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.141, 1.11 |
No. of reflections | 1508 |
No. of parameters | 100 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1i | 0.8900 | 2.2900 | 3.1736 (18) | 170.00 |
N1—H1B···Cl1ii | 0.8900 | 2.3900 | 3.2015 (17) | 152.00 |
N1—H1C···O1W | 0.8900 | 1.8200 | 2.704 (3) | 175.00 |
O1W—H1W···Cl1 | 0.72 (3) | 2.45 (2) | 3.167 (2) | 177.9 (14) |
O1W—H2W···Cl1iii | 0.76 (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, y−1/2, −z+1/2. |
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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).