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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1026.
Published online 2008 May 10. doi:  10.1107/S1600536808013093
PMCID: PMC2961557

4-Amino-2-methyl­quinoline monohydrate

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-o1026-scheme1.jpg

Experimental

Crystal data

  • C10H10N2·H2O
  • M r = 176.22
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1026-efi1.jpg
  • a = 4.7432 (8) Å
  • b = 13.9070 (13) Å
  • c = 14.5129 (16) Å
  • V = 957.3 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 298 (2) K
  • 0.43 × 0.35 × 0.32 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.966, T max = 0.975
  • 3925 measured reflections
  • 882 independent reflections
  • 716 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.093
  • S = 1.04
  • 882 reflections
  • 119 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.10 e Å−3
  • Δρmin = −0.11 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013093/at2564sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013093/at2564Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

Fig. 1.
The molecular structure of (I) showing 30% displacement ellipsoids.

Crystal data

C10H10N2·H2O1F000 = 376
Mr = 176.22Dx = 1.223 Mg m3
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 mm1
c = 14.5129 (16) ÅT = 298 (2) K
V = 957.3 (2) Å3Block, colourless
Z = 40.43 × 0.35 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer882 independent reflections
Radiation source: fine-focus sealed tube716 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.029
T = 298(2) Kθmax = 25.0º
[var phi] 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

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 Å3
119 parametersΔρmin = −0.11 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2564).

References

  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tai, X. S. & Feng, Y. M. (2008). Acta Cryst. E64, o707. [PMC free article] [PubMed]
  • Tai, X.-S., Feng, Y.-M. & Zhang, H.-X. (2008). Acta Cryst. E64, m502. [PMC free article] [PubMed]
  • 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.

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