PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o97.
Published online 2007 December 6. doi:  10.1107/S1600536807063246
PMCID: PMC2915051

8-Hydroxy-2-methylquinoline

Abstract

The asymmetric unit of the title compound, C10H9NO, contains two independent mol­ecules which are linked by a pair of O—H(...)N hydrogen bonds into a hydrogen-bonded dimer.

Related literature

Aluminium derivatives of 2-methyl-8-hydroxy­quinoline are light-emitting compounds. For their crystal structures, see: Iijima & Yamamoto (2006 [triangle]); Kushi & Fernando (1970 [triangle]); Rajeswaran et al. (2007 [triangle]); Toulokhonova et al. (2002 [triangle]); Yamaguchi et al. (2002a [triangle],b [triangle]); Yuchi et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-00o97-scheme1.jpg

Experimental

Crystal data

  • C10H9NO
  • M r = 159.18
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-00o97-efi1.jpg
  • a = 12.6542 (5) Å
  • b = 10.9976 (6) Å
  • c = 23.6264 (10) Å
  • V = 3288.0 (3) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 (2) K
  • 0.30 × 0.25 × 0.25 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.975, T max = 0.979
  • 30335 measured reflections
  • 3769 independent reflections
  • 2055 reflections with I > 2σ(I)
  • R int = 0.047

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.188
  • S = 1.10
  • 3769 reflections
  • 228 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2007 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063246/ci2524sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063246/ci2524Isup2.hkl

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

Acknowledgments

The authors thank Shahid Beheshti University, the Heilongjiang Province Natural Science Foundation (grant No. B200501), the Scientific Fund for Remarkable Teachers of Heilongjiang Province (grant No. 1054 G036), and the University of Malaya for supporting this work.

supplementary crystallographic information

Comment

The asymmetric unit of the title compound contains two molecules; the corresponding bond lengths and angles of these two molecules agree with each other. In the solid state, the two independent molecules exist as O—H···N hydrogen-bonded dimer; the mean planes through the non-hydrogen atoms of the two molecules form a dihedral angle of 77.98 (5)°.

Experimental

Commercially available 2-methyl-8-hydroxyquinoline was recrystallized from diethyl ether.

Refinement

Carbon- and oxygen-bound H atoms were placed in calculated positions [C—H 0.93–0.96 Å and Uiso(H) = 1.2–1.5Ueq(C)], and were included in the refinement in the riding-model approximation. The hydroxyl H-atoms were located in a difference Fourier map, and were refined with a O—H distance restraint of 0.85 (1) Å.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing the hydrogen-bonded dimeric structure. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C10H9NOF000 = 1344
Mr = 159.18Dx = 1.286 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 15421 reflections
a = 12.6542 (5) Åθ = 3.0–27.5º
b = 10.9976 (6) ŵ = 0.08 mm1
c = 23.6264 (10) ÅT = 295 (2) K
V = 3288.0 (3) Å3Block, colourless
Z = 160.30 × 0.25 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID diffractometer3769 independent reflections
Radiation source: fine-focus sealed tube2055 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
Detector resolution: 10.000 pixels mm-1θmax = 27.5º
T = 295(2) Kθmin = 3.0º
ω–scansh = −16→16
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)k = −14→14
Tmin = 0.975, Tmax = 0.979l = −30→26
30335 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.188  w = 1/[σ2(Fo2) + (0.1035P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
3769 reflectionsΔρmax = 0.22 e Å3
228 parametersΔρmin = −0.21 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0065 (13)

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

xyzUiso*/Ueq
O10.75378 (11)0.58979 (15)0.60707 (6)0.0612 (4)
H1O0.712 (2)0.644 (2)0.6204 (12)0.117 (11)*
O20.49093 (12)0.60686 (17)0.66008 (6)0.0703 (5)
H2O0.534 (2)0.650 (3)0.6411 (12)0.127 (12)*
N10.58151 (11)0.69189 (15)0.55393 (6)0.0467 (4)
N20.66746 (12)0.72562 (15)0.70068 (7)0.0501 (4)
C10.64032 (13)0.60751 (17)0.52540 (7)0.0440 (4)
C20.72545 (14)0.55220 (19)0.55461 (8)0.0474 (5)
C30.78109 (15)0.4604 (2)0.52974 (9)0.0544 (5)
H30.83510.42220.54960.065*
C40.75763 (16)0.4235 (2)0.47477 (9)0.0580 (6)
H40.79580.36010.45860.070*
C50.67994 (15)0.4782 (2)0.44415 (8)0.0563 (5)
H50.66710.45460.40700.068*
C60.61901 (14)0.57120 (19)0.46936 (8)0.0483 (5)
C70.53480 (15)0.6315 (2)0.44188 (8)0.0574 (6)
H70.51830.61260.40460.069*
C80.47827 (16)0.7167 (2)0.46992 (9)0.0577 (6)
H80.42360.75730.45170.069*
C90.50225 (14)0.74416 (19)0.52701 (8)0.0511 (5)
C100.43762 (18)0.8347 (2)0.55908 (10)0.0708 (7)
H10A0.45100.82600.59890.106*
H10B0.36400.82080.55170.106*
H10C0.45630.91540.54730.106*
C110.60152 (14)0.66840 (18)0.73818 (8)0.0482 (5)
C120.51288 (15)0.6056 (2)0.71618 (8)0.0540 (5)
C130.44816 (16)0.5426 (2)0.75192 (9)0.0651 (6)
H130.39030.50080.73740.078*
C140.4678 (2)0.5401 (3)0.81019 (10)0.0758 (7)
H140.42300.49630.83380.091*
C150.5506 (2)0.6003 (3)0.83250 (9)0.0727 (7)
H150.56240.59810.87130.087*
C160.61957 (15)0.6667 (2)0.79724 (8)0.0563 (5)
C170.70723 (18)0.7335 (2)0.81663 (9)0.0686 (7)
H170.72140.73780.85520.082*
C180.77087 (17)0.7914 (2)0.77952 (9)0.0663 (6)
H180.82830.83600.79260.080*
C190.75035 (15)0.7842 (2)0.72081 (9)0.0548 (5)
C200.82399 (19)0.8427 (2)0.67981 (10)0.0756 (7)
H20A0.80210.82390.64190.113*
H20B0.89430.81260.68590.113*
H20C0.82300.92920.68520.113*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0610 (8)0.0722 (11)0.0505 (8)0.0135 (7)−0.0151 (7)−0.0101 (7)
O20.0653 (9)0.0976 (14)0.0480 (8)−0.0233 (9)−0.0058 (7)−0.0011 (8)
N10.0446 (8)0.0474 (10)0.0480 (9)−0.0003 (7)−0.0025 (7)−0.0011 (7)
N20.0519 (9)0.0510 (10)0.0472 (9)0.0005 (7)−0.0025 (7)0.0006 (7)
C10.0424 (9)0.0459 (11)0.0436 (10)−0.0044 (8)0.0001 (8)0.0012 (8)
C20.0453 (10)0.0522 (13)0.0447 (10)−0.0002 (8)−0.0032 (8)−0.0014 (9)
C30.0496 (10)0.0569 (14)0.0569 (12)0.0058 (9)−0.0013 (9)−0.0021 (10)
C40.0551 (11)0.0561 (13)0.0629 (13)0.0015 (10)0.0084 (10)−0.0107 (10)
C50.0572 (11)0.0649 (15)0.0468 (11)−0.0067 (10)0.0012 (9)−0.0092 (10)
C60.0469 (10)0.0535 (12)0.0444 (10)−0.0077 (9)−0.0015 (8)0.0006 (8)
C70.0580 (11)0.0683 (15)0.0457 (11)−0.0061 (10)−0.0076 (9)0.0024 (10)
C80.0523 (11)0.0643 (14)0.0565 (12)0.0021 (10)−0.0112 (9)0.0088 (11)
C90.0456 (10)0.0498 (12)0.0580 (12)−0.0007 (9)−0.0035 (9)0.0054 (9)
C100.0630 (12)0.0677 (17)0.0816 (16)0.0154 (11)−0.0038 (11)−0.0077 (13)
C110.0507 (10)0.0497 (12)0.0443 (10)0.0064 (9)0.0006 (8)−0.0018 (8)
C120.0521 (10)0.0619 (14)0.0482 (11)−0.0001 (9)0.0016 (9)−0.0026 (9)
C130.0565 (12)0.0762 (17)0.0625 (14)−0.0072 (11)0.0075 (10)0.0017 (12)
C140.0747 (15)0.087 (2)0.0660 (15)0.0006 (13)0.0227 (12)0.0095 (13)
C150.0825 (16)0.090 (2)0.0458 (12)0.0035 (14)0.0082 (11)0.0029 (12)
C160.0632 (12)0.0614 (14)0.0441 (10)0.0094 (10)−0.0013 (9)−0.0026 (10)
C170.0759 (14)0.0834 (18)0.0465 (12)0.0016 (13)−0.0129 (11)−0.0078 (11)
C180.0664 (13)0.0716 (17)0.0608 (13)−0.0041 (12)−0.0157 (11)−0.0100 (11)
C190.0539 (11)0.0508 (13)0.0595 (12)0.0017 (9)−0.0057 (10)−0.0016 (10)
C200.0762 (15)0.0700 (17)0.0804 (16)−0.0200 (12)−0.0057 (12)0.0064 (13)

Geometric parameters (Å, °)

O1—C21.355 (2)C9—C101.494 (3)
O1—H1O0.86 (3)C10—H10A0.96
O2—C121.354 (2)C10—H10B0.96
O2—H2O0.85 (3)C10—H10C0.96
N1—C91.319 (2)C11—C161.414 (3)
N1—C11.367 (2)C11—C121.416 (3)
N2—C191.320 (2)C12—C131.365 (3)
N2—C111.370 (2)C13—C141.399 (3)
C1—C61.409 (2)C13—H130.93
C1—C21.417 (2)C14—C151.348 (3)
C2—C31.364 (3)C14—H140.93
C3—C41.393 (3)C15—C161.410 (3)
C3—H30.93C15—H150.93
C4—C51.361 (3)C16—C171.407 (3)
C4—H40.93C17—C181.350 (3)
C5—C61.412 (3)C17—H170.930
C5—H50.93C18—C191.413 (3)
C6—C71.413 (3)C18—H180.93
C7—C81.352 (3)C19—C201.490 (3)
C7—H70.93C20—H20A0.96
C8—C91.415 (3)C20—H20B0.96
C8—H80.93C20—H20C0.96
C2—O1—H1O113 (2)H10A—C10—H10C109.5
C12—O2—H2O113 (2)H10B—C10—H10C109.5
C9—N1—C1118.15 (16)N2—C11—C16123.07 (17)
C19—N2—C11118.38 (17)N2—C11—C12117.97 (17)
N1—C1—C6123.48 (16)C16—C11—C12118.93 (18)
N1—C1—C2117.72 (16)O2—C12—C13119.17 (19)
C6—C1—C2118.79 (17)O2—C12—C11121.11 (18)
O1—C2—C3118.90 (17)C13—C12—C11119.72 (19)
O1—C2—C1121.06 (17)C12—C13—C14120.8 (2)
C3—C2—C1120.04 (18)C12—C13—H13119.6
C2—C3—C4120.50 (18)C14—C13—H13119.6
C2—C3—H3119.8C15—C14—C13120.9 (2)
C4—C3—H3119.8C15—C14—H14119.6
C5—C4—C3121.4 (2)C13—C14—H14119.6
C5—C4—H4119.3C14—C15—C16120.3 (2)
C3—C4—H4119.3C14—C15—H15119.8
C4—C5—C6119.38 (19)C16—C15—H15119.8
C4—C5—H5120.3C17—C16—C15124.4 (2)
C6—C5—H5120.3C17—C16—C11116.22 (19)
C1—C6—C5119.80 (17)C15—C16—C11119.33 (19)
C1—C6—C7116.30 (18)C18—C17—C16120.33 (19)
C5—C6—C7123.90 (19)C18—C17—H17119.8
C8—C7—C6119.93 (19)C16—C17—H17119.8
C8—C7—H7120.0C17—C18—C19120.1 (2)
C6—C7—H7120.0C17—C18—H18119.9
C7—C8—C9120.10 (18)C19—C18—H18119.9
C7—C8—H8120.0N2—C19—C18121.8 (2)
C9—C8—H8120.0N2—C19—C20118.26 (18)
N1—C9—C8121.96 (19)C18—C19—C20119.95 (19)
N1—C9—C10117.50 (18)C19—C20—H20A109.5
C8—C9—C10120.53 (18)C19—C20—H20B109.5
C9—C10—H10A109.5H20A—C20—H20B109.5
C9—C10—H10B109.5C19—C20—H20C109.5
H10A—C10—H10B109.5H20A—C20—H20C109.5
C9—C10—H10C109.5H20B—C20—H20C109.5
C9—N1—C1—C6−1.7 (3)C19—N2—C11—C16−1.6 (3)
C9—N1—C1—C2179.80 (17)C19—N2—C11—C12−179.91 (18)
N1—C1—C2—O1−6.1 (3)N2—C11—C12—O2−3.1 (3)
C6—C1—C2—O1175.38 (17)C16—C11—C12—O2178.49 (19)
N1—C1—C2—C3174.58 (17)N2—C11—C12—C13176.9 (2)
C6—C1—C2—C3−3.9 (3)C16—C11—C12—C13−1.5 (3)
O1—C2—C3—C4−176.79 (19)O2—C12—C13—C14−179.4 (2)
C1—C2—C3—C42.5 (3)C11—C12—C13—C140.6 (4)
C2—C3—C4—C50.7 (3)C12—C13—C14—C150.4 (4)
C3—C4—C5—C6−2.5 (3)C13—C14—C15—C16−0.3 (4)
N1—C1—C6—C5−176.28 (17)C14—C15—C16—C17179.2 (2)
C2—C1—C6—C52.2 (3)C14—C15—C16—C11−0.7 (4)
N1—C1—C6—C73.0 (3)N2—C11—C16—C173.4 (3)
C2—C1—C6—C7−178.55 (17)C12—C11—C16—C17−178.32 (19)
C4—C5—C6—C11.0 (3)N2—C11—C16—C15−176.7 (2)
C4—C5—C6—C7−178.21 (19)C12—C11—C16—C151.6 (3)
C1—C6—C7—C8−1.5 (3)C15—C16—C17—C18177.9 (2)
C5—C6—C7—C8177.73 (19)C11—C16—C17—C18−2.2 (3)
C6—C7—C8—C9−1.0 (3)C16—C17—C18—C19−0.6 (4)
C1—N1—C9—C8−1.0 (3)C11—N2—C19—C18−1.4 (3)
C1—N1—C9—C10179.00 (17)C11—N2—C19—C20177.9 (2)
C7—C8—C9—N12.4 (3)C17—C18—C19—N22.5 (4)
C7—C8—C9—C10−177.6 (2)C17—C18—C19—C20−176.7 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O···N20.86 (3)2.17 (2)2.884 (2)140 (3)
O2—H2O···N10.85 (3)2.19 (2)2.912 (2)142 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2524).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Iijima, T. & Yamamoto, T. (2006). J. Organomet. Chem.691, 5016–5023. Publ.
  • Kushi, Y. & Fernando, Q. (1970). J. Am. Chem. Soc.92, 91–96.
  • Rajeswaran, M., Place, D. W., Bakos, V. W., Deaton, J. C., Brown, C. T. & Lenhard, W. C. (2007). Acta Cryst. E63, m54–m56.
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (1997). SHELXL97 and SHELXS97 University of Göttingen, Germany.
  • Toulokhonova, I. S., Guzei, I. A., Kavana, M. & West, R. (2002). Main Group Met. Chem.25, 489–495.
  • Westrip, S. P. (2007). publCIF In preparation.
  • Yamaguchi, I., Iijima, T. & Yamamoto, T. (2002a). J. Organomet. Chem.654, 229–232.
  • Yamaguchi, I., Iijima, T. & Yamamoto, T. (2002b). J. Organomet. Chem.658, 281.
  • Yuchi, A., Hiramatsu, H., Ohara, M. & Ohata, N. (2003). Anal. Sci.19, 1177–1181. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography