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Acta Cryst. (2008). E64, o1026    [ doi:10.1107/S1600536808013093 ]

4-Amino-2-methylquinoline monohydrate

X.-S. Tai, J. Xu, Y.-M. Feng and Z.-P. Liang

Abstract top

The crystal structure of the title compound, C10H10N2·H2O, is stabilized by intermolecular O-H...N, N-H...O and N-H...N hydrogen bonds.

Comment top

As part of our ongoing studies of the coordination chemistry of ligands containing nitrogen (Tai et al., 2003; Tai, Yin & Feng, 2007; Tai, Yin, Feng & Kong, 2007; Tai, Yin & Hao, 2007; Tai & Feng, 2008; Tai, Feng & Zhang, 2008; Wang et al., 2007), we now report the structure of the title compound, (I), (Fig. 1).

In the molecule of (I), the geometrical parameters for (I) are normal. The packing is stabilized by the intermolecular O—H···N, N—H···O and N—H···N hydrogen bonds (Table 1).

Related literature top

For related literature, see: Tai et al. (2003); Tai et al. (2008); Tai, Yin & Feng (2007); Tai, Yin & Hao (2007); Tai, Yin et al. (2007); Tai & Feng (2008); Wang et al. (2007).

Experimental top

1 mmol of Ethyl benzoylacetate was added to a solution of 4-amino-2-methylquinoline (1 mmol) in 10 ml of 95% ethanol. The mixture was stirred for 2 h at refluxing temperature. Evaporating some ethanol, clear blocks of (I) were obtained after one weeks.

Refinement top

The H atoms were placed geometrically (C—H = 0.93–0.96 Å, O—H = 0.852 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2 or 1.5Ueq(carrier).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% displacement ellipsoids.
4-Amino-2-methylquinoline monohydrate top
Crystal data top
C10H10N2·H2O1F000 = 376
Mr = 176.22Dx = 1.223 Mg m−3
Orthorhombic, Pna21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 1365 reflections
a = 4.7432 (8) Åθ = 2.8–23.5º
b = 13.9070 (13) ŵ = 0.08 mm−1
c = 14.5129 (16) ÅT = 298 (2) K
V = 957.3 (2) Å3Block, colourless
Z = 40.43 × 0.35 × 0.32 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		882 independent reflections
Radiation source: fine-focus sealed tube716 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.029
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 2.0º
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −5→5
Tmin = 0.966, Tmax = 0.975k = −16→15
3925 measured reflectionsl = −14→17
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)] = 0.032H-atom parameters constrained
wR(F2) = 0.093  w = 1/[σ2(Fo2) + (0.0498P)2 + 0.1333P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
882 reflectionsΔρmax = 0.10 e Å−3
119 parametersΔρmin = −0.11 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C10H10N2·H2O1V = 957.3 (2) Å3
Mr = 176.22Z = 4
Orthorhombic, Pna21Mo Kα
a = 4.7432 (8) ŵ = 0.08 mm−1
b = 13.9070 (13) ÅT = 298 (2) K
c = 14.5129 (16) Å0.43 × 0.35 × 0.32 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		882 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		716 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.975Rint = 0.029
3925 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.093Δρmax = 0.10 e Å−3
S = 1.05Δρmin = −0.11 e Å−3
882 reflectionsAbsolute structure: ?
119 parametersFlack parameter: ?
1 restraintRogers parameter: ?
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.

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
N10.0728 (5)0.56239 (17)0.32460 (17)0.0508 (7)
N20.2819 (6)0.33360 (19)0.49988 (18)0.0612 (7)
H2A0.19960.32880.55250.073*
H2B0.40340.29110.48320.073*
O10.9245 (4)0.69712 (15)0.18915 (16)0.0582 (6)
H11.07020.73260.19140.070*
H20.95100.65520.23090.070*
C1−0.2458 (8)0.6300 (2)0.4362 (3)0.0672 (9)
H1A−0.24910.68020.39070.101*
H1B−0.18910.65630.49450.101*
H1C−0.43060.60240.44170.101*
C2−0.0410 (6)0.5538 (2)0.4074 (2)0.0488 (8)
C30.0273 (7)0.4782 (2)0.46651 (19)0.0485 (7)
H3−0.06000.47460.52380.058*
C40.2193 (6)0.4091 (2)0.44254 (18)0.0452 (7)
C50.3470 (6)0.4156 (2)0.35341 (19)0.0429 (7)
C60.5474 (7)0.3508 (2)0.3196 (2)0.0523 (8)
H60.60300.29920.35620.063*
C70.6634 (8)0.3615 (3)0.2340 (2)0.0608 (9)
H70.79520.31750.21240.073*
C80.5828 (7)0.4388 (3)0.1796 (3)0.0631 (9)
H80.66240.44640.12150.076*
C90.3892 (7)0.5037 (2)0.20989 (19)0.0568 (9)
H90.33820.55490.17220.068*
C100.2654 (6)0.4944 (2)0.29716 (19)0.0455 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0487 (14)0.0540 (14)0.0498 (15)−0.0009 (12)−0.0061 (12)0.0071 (12)
N20.0754 (19)0.0656 (16)0.0428 (14)0.0058 (15)0.0043 (13)0.0133 (12)
O10.0614 (12)0.0590 (11)0.0544 (12)−0.0011 (11)−0.0117 (12)0.0083 (10)
C10.062 (2)0.066 (2)0.074 (2)0.0027 (18)0.0037 (19)−0.0011 (17)
C20.0423 (17)0.0539 (17)0.0502 (18)−0.0078 (14)−0.0049 (14)−0.0016 (15)
C30.0465 (16)0.0590 (18)0.0401 (16)−0.0100 (15)0.0010 (13)−0.0024 (14)
C40.0428 (17)0.0520 (16)0.0406 (15)−0.0113 (14)−0.0062 (13)0.0053 (13)
C50.0404 (15)0.0502 (16)0.0381 (14)−0.0100 (13)−0.0040 (12)0.0022 (11)
C60.0500 (17)0.0549 (17)0.0519 (18)−0.0033 (14)−0.0021 (15)0.0059 (14)
C70.056 (2)0.070 (2)0.056 (2)−0.0027 (16)0.0065 (17)−0.0026 (16)
C80.059 (2)0.084 (2)0.0464 (16)−0.0094 (18)0.0060 (17)0.0093 (18)
C90.0569 (18)0.069 (2)0.0440 (19)−0.0077 (18)−0.0041 (14)0.0147 (14)
C100.0416 (15)0.0540 (17)0.0408 (15)−0.0100 (13)−0.0067 (13)0.0042 (13)
Geometric parameters (Å, °) top
N1—C21.322 (4)C3—H30.9300
N1—C101.374 (4)C4—C51.431 (4)
N2—C41.372 (4)C5—C61.399 (4)
N2—H2A0.8600C5—C101.420 (4)
N2—H2B0.8600C6—C71.367 (5)
O1—H10.8500C6—H60.9300
O1—H20.8499C7—C81.387 (5)
C1—C21.497 (5)C7—H70.9300
C1—H1A0.9600C8—C91.361 (5)
C1—H1B0.9600C8—H80.9300
C1—H1C0.9600C9—C101.402 (4)
C2—C31.396 (4)C9—H90.9300
C3—C41.369 (4)
C2—N1—C10118.2 (2)N2—C4—C5120.3 (3)
C4—N2—H2A120.0C6—C5—C10118.7 (3)
C4—N2—H2B120.0C6—C5—C4124.3 (3)
H2A—N2—H2B120.0C10—C5—C4116.9 (3)
H1—O1—H2104.5C7—C6—C5121.4 (3)
C2—C1—H1A109.5C7—C6—H6119.3
C2—C1—H1B109.5C5—C6—H6119.3
H1A—C1—H1B109.5C6—C7—C8119.4 (3)
C2—C1—H1C109.5C6—C7—H7120.3
H1A—C1—H1C109.5C8—C7—H7120.3
H1B—C1—H1C109.5C9—C8—C7121.1 (3)
N1—C2—C3122.1 (3)C9—C8—H8119.4
N1—C2—C1117.0 (3)C7—C8—H8119.4
C3—C2—C1120.8 (3)C8—C9—C10120.8 (3)
C4—C3—C2121.8 (3)C8—C9—H9119.6
C4—C3—H3119.1C10—C9—H9119.6
C2—C3—H3119.1N1—C10—C9118.4 (3)
C3—C4—N2121.8 (3)N1—C10—C5123.1 (3)
C3—C4—C5117.9 (3)C9—C10—C5118.5 (3)
C10—N1—C2—C3−0.4 (4)C5—C6—C7—C80.6 (5)
C10—N1—C2—C1178.8 (3)C6—C7—C8—C9−0.4 (5)
N1—C2—C3—C40.9 (4)C7—C8—C9—C100.1 (5)
C1—C2—C3—C4−178.3 (3)C2—N1—C10—C9−179.3 (2)
C2—C3—C4—N2−178.6 (3)C2—N1—C10—C50.1 (4)
C2—C3—C4—C5−1.0 (4)C8—C9—C10—N1179.5 (3)
C3—C4—C5—C6179.6 (3)C8—C9—C10—C50.1 (4)
N2—C4—C5—C6−2.8 (4)C6—C5—C10—N1−179.2 (3)
C3—C4—C5—C100.7 (4)C4—C5—C10—N1−0.2 (4)
N2—C4—C5—C10178.3 (2)C6—C5—C10—C90.1 (4)
C10—C5—C6—C7−0.5 (4)C4—C5—C10—C9179.1 (2)
C4—C5—C6—C7−179.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.851.942.791 (3)174
O1—H2···N1ii0.851.962.805 (3)171
N2—H2A···O1iii0.862.102.947 (4)168
N2—H2B···N2iv0.862.513.321 (4)158
Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x+1, y, z; (iii) −x+1, −y+1, z+1/2; (iv) x+1/2, −y+1/2, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O1i0.851.942.791 (3)174
O1—H2···N1ii0.851.962.805 (3)171
N2—H2A···O1iii0.862.102.947 (4)168
N2—H2B···N2iv0.862.513.321 (4)158
Symmetry codes: (i) x+1/2, −y+3/2, z; (ii) x+1, y, z; (iii) −x+1, −y+1, z+1/2; (iv) x+1/2, −y+1/2, z.
Acknowledgements top

The authors thank the National Natural Science Foundation of China (20671073), the National Natural Science Foundation of Shandong (Y2007B60), the Science and Technology Foundation of Weifang and Weifang University for research grants.

references
References top

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Tai, X. S. & Feng, Y. M. (2008). Acta Cryst. E64, o707.

Tai, X.-S., Feng, Y.-M. & Zhang, H.-X. (2008). Acta Cryst. E64, m502.

Tai, X. S., Yin, J. & Feng, Y. M. (2007). Z. Kristallogr. New Cryst. Struct. 222, 398–400.

Tai, X. S., Yin, J., Feng, Y. M. & Kong, F. Y. (2007). Chin. J. Inorg. Chem. 23, 1812–1814.

Tai, X.-S., Yin, J. & Hao, M.-Y. (2007). Acta Cryst. E63, m1061–m1062.

Tai, X.-S., Yin, X.-H., Tan, M.-Y. & Li, Y.-Z. (2003). Acta Cryst. E59, o681–o682.

Wang, L.-H., Yin, J. & Tai, X.-S. (2007). Acta Cryst. E63, m1664.