Crystal structure of (5-methyl-imidazo[1,2-a]pyridin-2-yl)methanol.

In the title compound, C9H10N2O, the imidazo[1,2-a]pyridine moiety is approximately planar (r.m.s. deviation = 0.024 Å). The methanol group is nearly perpendicular to its mean plane as indicated by the C-C-C-O and N-C-C-O torsion angles of 80.04 (16) and -96.30 (17)°, respectively. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds, forming inversion dimers with an R (2) 2(10) ring motif. The dimers are liked via C-H⋯O hydrogen bonds, enclosing R (2) 2(10) ring motifs and forming ribbons along [201]. The ribbons are linked via a number of π-π inter-actions [centroid-centroid distances vary from 3.4819 (8) to 3.7212 (8) Å], forming a three-dimensional structure.

Related literature

For the biological activities of derivatives of the title compound, see: Silvestre et al. (1998 ▶); Hamdouchi et al. (1999 ▶); Lhassani et al. (1999 ▶); Ertl et al. (2000 ▶). For the synthesis, see: Öhler et al. (1983 ▶); Chavignon et al. (1992 ▶).

Experimental

Crystal data

C9H10N2O

M = 162.19

Triclinic,

a = 7.3637 (2) Å

b = 8.1589 (2) Å

c = 8.3966 (2) Å

α = 62.355 (1)°

β = 67.291 (2)°

γ = 88.386 (2)°

V = 405.14 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.38 × 0.32 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer

10226 measured reflections

2089 independent reflections

1865 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.123

S = 1.04

2089 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814023022/su5007sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814023022/su5007Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814023022/su5007Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814023022/su5007fig1.tif

A view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S1600536814023022/su5007fig2.tif

A partial view perpendicular to a axis of the crystal packing of the title compound, showing a layer of mol­ecules linked by hydrogen bonds (dashed lines; see Table 1 for details).

CCDC reference: 1029873

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H10N2O	Z = 2
Mr = 162.19	F(000) = 172
Triclinic, P1	Dx = 1.330 Mg m−3
Hall symbol: -p 1	Melting point: 413 K
a = 7.3637 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1589 (2) Å	Cell parameters from 2089 reflections
c = 8.3966 (2) Å	θ = 2.9–28.7°
α = 62.355 (1)°	µ = 0.09 mm−1
β = 67.291 (2)°	T = 296 K
γ = 88.386 (2)°	Block, colourless
V = 405.14 (2) Å3	0.38 × 0.32 × 0.27 mm

Bruker X8 APEX diffractometer	1865 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 28.7°, θmin = 2.9°
φ and ω scans	h = −9→9
10226 measured reflections	k = −11→10
2089 independent reflections	l = −11→11

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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.0845P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2089 reflections	Δρmax = 0.24 e Å−3
110 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.061 (14)

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.

	x	y	z	Uiso*/Ueq
C1	0.23574 (17)	0.88694 (15)	0.02939 (17)	0.0374 (3)
C2	0.3772 (2)	0.8861 (2)	−0.1413 (2)	0.0487 (3)
H2	0.3890	0.7743	−0.1456	0.058*
C3	0.49565 (19)	1.0507 (2)	−0.29887 (19)	0.0502 (3)
H3	0.5907	1.0510	−0.4110	0.060*
C4	0.47630 (19)	1.22086 (19)	−0.29465 (18)	0.0466 (3)
H4	0.5601	1.3318	−0.4038	0.056*
C5	0.33794 (18)	1.22657 (16)	−0.13469 (16)	0.0399 (3)
C9	0.3049 (2)	1.39916 (18)	−0.1173 (2)	0.0565 (4)
H9B	0.3236	1.3850	−0.0049	0.085*
H9A	0.1709	1.4183	−0.1004	0.085*
H9C	0.3987	1.5057	−0.2355	0.085*
C6	0.07560 (16)	1.02021 (15)	0.21002 (15)	0.0363 (3)
H6	0.0311	1.1066	0.2529	0.044*
C7	0.01244 (16)	0.82991 (15)	0.31517 (16)	0.0383 (3)
C8	−0.1332 (2)	0.71513 (18)	0.52658 (18)	0.0496 (3)
H8A	−0.2211	0.7936	0.5652	0.060*
H8B	−0.2151	0.6140	0.5406	0.060*
N1	0.10972 (15)	0.74701 (14)	0.20387 (15)	0.0420 (3)
N2	0.21944 (13)	1.05816 (12)	0.02646 (13)	0.0339 (2)
O1	−0.03554 (17)	0.63769 (13)	0.65406 (14)	0.0566 (3)
H1	−0.0705	0.5229	0.7180	0.085*

	U11	U22	U33	U12	U13	U23
C1	0.0427 (6)	0.0355 (5)	0.0412 (6)	0.0108 (4)	−0.0231 (5)	−0.0201 (4)
C2	0.0558 (7)	0.0532 (7)	0.0519 (7)	0.0214 (6)	−0.0269 (6)	−0.0342 (6)
C3	0.0463 (6)	0.0690 (9)	0.0402 (6)	0.0161 (6)	−0.0178 (5)	−0.0310 (6)
C4	0.0450 (6)	0.0538 (7)	0.0341 (5)	0.0009 (5)	−0.0155 (5)	−0.0170 (5)
C5	0.0445 (6)	0.0379 (6)	0.0335 (5)	0.0009 (4)	−0.0176 (5)	−0.0134 (4)
C9	0.0760 (9)	0.0358 (6)	0.0433 (6)	−0.0035 (6)	−0.0164 (6)	−0.0147 (5)
C6	0.0392 (5)	0.0342 (5)	0.0336 (5)	0.0073 (4)	−0.0146 (4)	−0.0158 (4)
C7	0.0388 (5)	0.0343 (5)	0.0381 (5)	0.0057 (4)	−0.0178 (4)	−0.0139 (4)
C8	0.0488 (7)	0.0407 (6)	0.0411 (6)	0.0028 (5)	−0.0115 (5)	−0.0119 (5)
N1	0.0494 (6)	0.0332 (5)	0.0445 (5)	0.0086 (4)	−0.0222 (4)	−0.0179 (4)
N2	0.0376 (5)	0.0325 (4)	0.0329 (4)	0.0063 (3)	−0.0171 (4)	−0.0151 (4)
O1	0.0880 (7)	0.0361 (5)	0.0419 (5)	0.0043 (4)	−0.0303 (5)	−0.0136 (4)

C1—N1	1.3299 (15)	C9—H9A	0.9600
C1—N2	1.3884 (14)	C9—H9C	0.9600
C1—C2	1.4126 (17)	C6—C7	1.3631 (15)
C2—C3	1.356 (2)	C6—N2	1.3815 (13)
C2—H2	0.9300	C6—H6	0.9300
C3—C4	1.407 (2)	C7—N1	1.3735 (15)
C3—H3	0.9300	C7—C8	1.4907 (16)
C4—C5	1.3576 (17)	C8—O1	1.4154 (16)
C4—H4	0.9300	C8—H8A	0.9700
C5—N2	1.3823 (14)	C8—H8B	0.9700
C5—C9	1.4857 (18)	O1—H1	0.8200
C9—H9B	0.9600
N1—C1—N2	110.57 (10)	H9B—C9—H9C	109.5
N1—C1—C2	131.10 (11)	H9A—C9—H9C	109.5
N2—C1—C2	118.32 (11)	C7—C6—N2	105.70 (10)
C3—C2—C1	119.09 (12)	C7—C6—H6	127.1
C3—C2—H2	120.5	N2—C6—H6	127.1
C1—C2—H2	120.5	C6—C7—N1	111.22 (10)
C2—C3—C4	120.76 (12)	C6—C7—C8	127.34 (11)
C2—C3—H3	119.6	N1—C7—C8	121.36 (11)
C4—C3—H3	119.6	O1—C8—C7	111.84 (10)
C5—C4—C3	121.41 (12)	O1—C8—H8A	109.2
C5—C4—H4	119.3	C7—C8—H8A	109.2
C3—C4—H4	119.3	O1—C8—H8B	109.2
C4—C5—N2	117.59 (11)	C7—C8—H8B	109.2
C4—C5—C9	125.31 (11)	H8A—C8—H8B	107.9
N2—C5—C9	117.10 (10)	C1—N1—C7	105.62 (9)
C5—C9—H9B	109.5	C6—N2—C5	130.27 (10)
C5—C9—H9A	109.5	C6—N2—C1	106.89 (9)
H9B—C9—H9A	109.5	C5—N2—C1	122.79 (10)
C5—C9—H9C	109.5	C8—O1—H1	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.98	2.7734 (17)	163
C6—H6···O1ii	0.93	2.55	3.4395 (18)	160

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1N1i	0.82	1.98	2.7734(17)	163
C6H6O1ii	0.93	2.55	3.4395(18)	160

Symmetry codes: (i) ; (ii) .