8-Hydroxy-2-methylquinoline.

The asymmetric unit of the title compound, C(10)H(9)NO, contains two independent mol-ecules 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 ▶); Kushi & Fernando (1970 ▶); Rajeswaran et al. (2007 ▶); Toulokhonova et al. (2002 ▶); Yamaguchi et al. (2002a ▶,b ▶); Yuchi et al. (2003 ▶).

Experimental

Crystal data

C10H9NO

M = 159.18

Orthorhombic,

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

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

C10H9NO	F000 = 1344
Mr = 159.18	Dx = 1.286 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 15421 reflections
a = 12.6542 (5) Å	θ = 3.0–27.5º
b = 10.9976 (6) Å	µ = 0.08 mm−1
c = 23.6264 (10) Å	T = 295 (2) K
V = 3288.0 (3) Å3	Block, colourless
Z = 16	0.30 × 0.25 × 0.25 mm

Rigaku R-AXIS RAPID diffractometer	3769 independent reflections
Radiation source: fine-focus sealed tube	2055 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
Detector resolution: 10.000 pixels mm-1	θmax = 27.5º
T = 295(2) K	θmin = 3.0º
ω–scans	h = −16→16
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	k = −14→14
Tmin = 0.975, Tmax = 0.979	l = −30→26
30335 measured reflections

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)] = 0.053	H 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 reflections	Δρmax = 0.22 e Å−3
228 parameters	Δρmin = −0.21 e Å−3
2 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0065 (13)

	x	y	z	Uiso*/Ueq
O1	0.75378 (11)	0.58979 (15)	0.60707 (6)	0.0612 (4)
H1O	0.712 (2)	0.644 (2)	0.6204 (12)	0.117 (11)*
O2	0.49093 (12)	0.60686 (17)	0.66008 (6)	0.0703 (5)
H2O	0.534 (2)	0.650 (3)	0.6411 (12)	0.127 (12)*
N1	0.58151 (11)	0.69189 (15)	0.55393 (6)	0.0467 (4)
N2	0.66746 (12)	0.72562 (15)	0.70068 (7)	0.0501 (4)
C1	0.64032 (13)	0.60751 (17)	0.52540 (7)	0.0440 (4)
C2	0.72545 (14)	0.55220 (19)	0.55461 (8)	0.0474 (5)
C3	0.78109 (15)	0.4604 (2)	0.52974 (9)	0.0544 (5)
H3	0.8351	0.4222	0.5496	0.065*
C4	0.75763 (16)	0.4235 (2)	0.47477 (9)	0.0580 (6)
H4	0.7958	0.3601	0.4586	0.070*
C5	0.67994 (15)	0.4782 (2)	0.44415 (8)	0.0563 (5)
H5	0.6671	0.4546	0.4070	0.068*
C6	0.61901 (14)	0.57120 (19)	0.46936 (8)	0.0483 (5)
C7	0.53480 (15)	0.6315 (2)	0.44188 (8)	0.0574 (6)
H7	0.5183	0.6126	0.4046	0.069*
C8	0.47827 (16)	0.7167 (2)	0.46992 (9)	0.0577 (6)
H8	0.4236	0.7573	0.4517	0.069*
C9	0.50225 (14)	0.74416 (19)	0.52701 (8)	0.0511 (5)
C10	0.43762 (18)	0.8347 (2)	0.55908 (10)	0.0708 (7)
H10A	0.4510	0.8260	0.5989	0.106*
H10B	0.3640	0.8208	0.5517	0.106*
H10C	0.4563	0.9154	0.5473	0.106*
C11	0.60152 (14)	0.66840 (18)	0.73818 (8)	0.0482 (5)
C12	0.51288 (15)	0.6056 (2)	0.71618 (8)	0.0540 (5)
C13	0.44816 (16)	0.5426 (2)	0.75192 (9)	0.0651 (6)
H13	0.3903	0.5008	0.7374	0.078*
C14	0.4678 (2)	0.5401 (3)	0.81019 (10)	0.0758 (7)
H14	0.4230	0.4963	0.8338	0.091*
C15	0.5506 (2)	0.6003 (3)	0.83250 (9)	0.0727 (7)
H15	0.5624	0.5981	0.8713	0.087*
C16	0.61957 (15)	0.6667 (2)	0.79724 (8)	0.0563 (5)
C17	0.70723 (18)	0.7335 (2)	0.81663 (9)	0.0686 (7)
H17	0.7214	0.7378	0.8552	0.082*
C18	0.77087 (17)	0.7914 (2)	0.77952 (9)	0.0663 (6)
H18	0.8283	0.8360	0.7926	0.080*
C19	0.75035 (15)	0.7842 (2)	0.72081 (9)	0.0548 (5)
C20	0.82399 (19)	0.8427 (2)	0.67981 (10)	0.0756 (7)
H20A	0.8021	0.8239	0.6419	0.113*
H20B	0.8943	0.8126	0.6859	0.113*
H20C	0.8230	0.9292	0.6852	0.113*

	U11	U22	U33	U12	U13	U23
O1	0.0610 (8)	0.0722 (11)	0.0505 (8)	0.0135 (7)	−0.0151 (7)	−0.0101 (7)
O2	0.0653 (9)	0.0976 (14)	0.0480 (8)	−0.0233 (9)	−0.0058 (7)	−0.0011 (8)
N1	0.0446 (8)	0.0474 (10)	0.0480 (9)	−0.0003 (7)	−0.0025 (7)	−0.0011 (7)
N2	0.0519 (9)	0.0510 (10)	0.0472 (9)	0.0005 (7)	−0.0025 (7)	0.0006 (7)
C1	0.0424 (9)	0.0459 (11)	0.0436 (10)	−0.0044 (8)	0.0001 (8)	0.0012 (8)
C2	0.0453 (10)	0.0522 (13)	0.0447 (10)	−0.0002 (8)	−0.0032 (8)	−0.0014 (9)
C3	0.0496 (10)	0.0569 (14)	0.0569 (12)	0.0058 (9)	−0.0013 (9)	−0.0021 (10)
C4	0.0551 (11)	0.0561 (13)	0.0629 (13)	0.0015 (10)	0.0084 (10)	−0.0107 (10)
C5	0.0572 (11)	0.0649 (15)	0.0468 (11)	−0.0067 (10)	0.0012 (9)	−0.0092 (10)
C6	0.0469 (10)	0.0535 (12)	0.0444 (10)	−0.0077 (9)	−0.0015 (8)	0.0006 (8)
C7	0.0580 (11)	0.0683 (15)	0.0457 (11)	−0.0061 (10)	−0.0076 (9)	0.0024 (10)
C8	0.0523 (11)	0.0643 (14)	0.0565 (12)	0.0021 (10)	−0.0112 (9)	0.0088 (11)
C9	0.0456 (10)	0.0498 (12)	0.0580 (12)	−0.0007 (9)	−0.0035 (9)	0.0054 (9)
C10	0.0630 (12)	0.0677 (17)	0.0816 (16)	0.0154 (11)	−0.0038 (11)	−0.0077 (13)
C11	0.0507 (10)	0.0497 (12)	0.0443 (10)	0.0064 (9)	0.0006 (8)	−0.0018 (8)
C12	0.0521 (10)	0.0619 (14)	0.0482 (11)	−0.0001 (9)	0.0016 (9)	−0.0026 (9)
C13	0.0565 (12)	0.0762 (17)	0.0625 (14)	−0.0072 (11)	0.0075 (10)	0.0017 (12)
C14	0.0747 (15)	0.087 (2)	0.0660 (15)	0.0006 (13)	0.0227 (12)	0.0095 (13)
C15	0.0825 (16)	0.090 (2)	0.0458 (12)	0.0035 (14)	0.0082 (11)	0.0029 (12)
C16	0.0632 (12)	0.0614 (14)	0.0441 (10)	0.0094 (10)	−0.0013 (9)	−0.0026 (10)
C17	0.0759 (14)	0.0834 (18)	0.0465 (12)	0.0016 (13)	−0.0129 (11)	−0.0078 (11)
C18	0.0664 (13)	0.0716 (17)	0.0608 (13)	−0.0041 (12)	−0.0157 (11)	−0.0100 (11)
C19	0.0539 (11)	0.0508 (13)	0.0595 (12)	0.0017 (9)	−0.0057 (10)	−0.0016 (10)
C20	0.0762 (15)	0.0700 (17)	0.0804 (16)	−0.0200 (12)	−0.0057 (12)	0.0064 (13)

O1—C2	1.355 (2)	C9—C10	1.494 (3)
O1—H1O	0.86 (3)	C10—H10A	0.96
O2—C12	1.354 (2)	C10—H10B	0.96
O2—H2O	0.85 (3)	C10—H10C	0.96
N1—C9	1.319 (2)	C11—C16	1.414 (3)
N1—C1	1.367 (2)	C11—C12	1.416 (3)
N2—C19	1.320 (2)	C12—C13	1.365 (3)
N2—C11	1.370 (2)	C13—C14	1.399 (3)
C1—C6	1.409 (2)	C13—H13	0.93
C1—C2	1.417 (2)	C14—C15	1.348 (3)
C2—C3	1.364 (3)	C14—H14	0.93
C3—C4	1.393 (3)	C15—C16	1.410 (3)
C3—H3	0.93	C15—H15	0.93
C4—C5	1.361 (3)	C16—C17	1.407 (3)
C4—H4	0.93	C17—C18	1.350 (3)
C5—C6	1.412 (3)	C17—H17	0.930
C5—H5	0.93	C18—C19	1.413 (3)
C6—C7	1.413 (3)	C18—H18	0.93
C7—C8	1.352 (3)	C19—C20	1.490 (3)
C7—H7	0.93	C20—H20A	0.96
C8—C9	1.415 (3)	C20—H20B	0.96
C8—H8	0.93	C20—H20C	0.96
C2—O1—H1O	113 (2)	H10A—C10—H10C	109.5
C12—O2—H2O	113 (2)	H10B—C10—H10C	109.5
C9—N1—C1	118.15 (16)	N2—C11—C16	123.07 (17)
C19—N2—C11	118.38 (17)	N2—C11—C12	117.97 (17)
N1—C1—C6	123.48 (16)	C16—C11—C12	118.93 (18)
N1—C1—C2	117.72 (16)	O2—C12—C13	119.17 (19)
C6—C1—C2	118.79 (17)	O2—C12—C11	121.11 (18)
O1—C2—C3	118.90 (17)	C13—C12—C11	119.72 (19)
O1—C2—C1	121.06 (17)	C12—C13—C14	120.8 (2)
C3—C2—C1	120.04 (18)	C12—C13—H13	119.6
C2—C3—C4	120.50 (18)	C14—C13—H13	119.6
C2—C3—H3	119.8	C15—C14—C13	120.9 (2)
C4—C3—H3	119.8	C15—C14—H14	119.6
C5—C4—C3	121.4 (2)	C13—C14—H14	119.6
C5—C4—H4	119.3	C14—C15—C16	120.3 (2)
C3—C4—H4	119.3	C14—C15—H15	119.8
C4—C5—C6	119.38 (19)	C16—C15—H15	119.8
C4—C5—H5	120.3	C17—C16—C15	124.4 (2)
C6—C5—H5	120.3	C17—C16—C11	116.22 (19)
C1—C6—C5	119.80 (17)	C15—C16—C11	119.33 (19)
C1—C6—C7	116.30 (18)	C18—C17—C16	120.33 (19)
C5—C6—C7	123.90 (19)	C18—C17—H17	119.8
C8—C7—C6	119.93 (19)	C16—C17—H17	119.8
C8—C7—H7	120.0	C17—C18—C19	120.1 (2)
C6—C7—H7	120.0	C17—C18—H18	119.9
C7—C8—C9	120.10 (18)	C19—C18—H18	119.9
C7—C8—H8	120.0	N2—C19—C18	121.8 (2)
C9—C8—H8	120.0	N2—C19—C20	118.26 (18)
N1—C9—C8	121.96 (19)	C18—C19—C20	119.95 (19)
N1—C9—C10	117.50 (18)	C19—C20—H20A	109.5
C8—C9—C10	120.53 (18)	C19—C20—H20B	109.5
C9—C10—H10A	109.5	H20A—C20—H20B	109.5
C9—C10—H10B	109.5	C19—C20—H20C	109.5
H10A—C10—H10B	109.5	H20A—C20—H20C	109.5
C9—C10—H10C	109.5	H20B—C20—H20C	109.5
C9—N1—C1—C6	−1.7 (3)	C19—N2—C11—C16	−1.6 (3)
C9—N1—C1—C2	179.80 (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—O1	175.38 (17)	C16—C11—C12—O2	178.49 (19)
N1—C1—C2—C3	174.58 (17)	N2—C11—C12—C13	176.9 (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—C4	2.5 (3)	C11—C12—C13—C14	0.6 (4)
C2—C3—C4—C5	0.7 (3)	C12—C13—C14—C15	0.4 (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—C17	179.2 (2)
C2—C1—C6—C5	2.2 (3)	C14—C15—C16—C11	−0.7 (4)
N1—C1—C6—C7	3.0 (3)	N2—C11—C16—C17	3.4 (3)
C2—C1—C6—C7	−178.55 (17)	C12—C11—C16—C17	−178.32 (19)
C4—C5—C6—C1	1.0 (3)	N2—C11—C16—C15	−176.7 (2)
C4—C5—C6—C7	−178.21 (19)	C12—C11—C16—C15	1.6 (3)
C1—C6—C7—C8	−1.5 (3)	C15—C16—C17—C18	177.9 (2)
C5—C6—C7—C8	177.73 (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—C10	179.00 (17)	C11—N2—C19—C20	177.9 (2)
C7—C8—C9—N1	2.4 (3)	C17—C18—C19—N2	2.5 (4)
C7—C8—C9—C10	−177.6 (2)	C17—C18—C19—C20	−176.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N2	0.86 (3)	2.17 (2)	2.884 (2)	140 (3)
O2—H2O···N1	0.85 (3)	2.19 (2)	2.912 (2)	142 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N2	0.86 (3)	2.17 (2)	2.884 (2)	140 (3)
O2—H2O⋯N1	0.85 (3)	2.19 (2)	2.912 (2)	142 (3)