2-{[(Pyrazin-2-yl)amino]-meth-yl}phenol.

The two aromatic rings of the title compound, C(11)H(11)N(3)O, are nearly perpendicular to one another, with a dihedral angle between their planes of 80.52 (18)°. In the crystal, the amino N atom is a hydrogen-bond donor to the pyrazine N(1) atom of an inversion-related mol-ecule and the hy-droxy O atom is a hydrogen-bond donor to the pyrazine N(4) atom of another mol-ecule. The two hydrogen bonds lead to the formation of a helical chain that runs along the b axis.

Related literature

For the related compound 2-(anilinometh­yl)phenol, see: Qu et al. (2007 ▶).

Experimental

Crystal data

C11H11N3O

M = 201.23

Monoclinic,

a = 9.7021 (14) Å

b = 13.0937 (17) Å

c = 7.8806 (13) Å

β = 95.746 (5)°

V = 996.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.26 × 0.22 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.977, T max = 0.985

7686 measured reflections

1751 independent reflections

858 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.191

S = 1.06

1751 reflections

144 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031339/xu5580sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031339/xu5580Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031339/xu5580Isup3.cml

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

C11H11N3O	F(000) = 424
Mr = 201.23	Dx = 1.342 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3450 reflections
a = 9.7021 (14) Å	θ = 3.0–27.5°
b = 13.0937 (17) Å	µ = 0.09 mm−1
c = 7.8806 (13) Å	T = 295 K
β = 95.746 (5)°	Prism, colorless
V = 996.1 (3) Å3	0.26 × 0.22 × 0.17 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	1751 independent reflections
Radiation source: fine-focus sealed tube	858 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
ω scan	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.977, Tmax = 0.985	k = −15→15
7686 measured reflections	l = −9→9

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0862P)2 + 0.1018P] where P = (Fo2 + 2Fc2)/3
1751 reflections	(Δ/σ)max = 0.001
144 parameters	Δρmax = 0.18 e Å−3
2 restraints	Δρmin = −0.20 e Å−3

	x	y	z	Uiso*/Ueq
O1	−0.0468 (3)	0.63270 (19)	0.2017 (3)	0.0656 (8)
N1	0.4697 (3)	0.3661 (2)	0.0705 (4)	0.0578 (8)
N2	0.2758 (3)	0.2358 (2)	0.1926 (4)	0.0691 (9)
N3	0.3227 (3)	0.5014 (2)	0.0842 (4)	0.0654 (9)
C1	0.4925 (4)	0.2662 (3)	0.0949 (5)	0.0684 (11)
H1A	0.5772	0.2396	0.0707	0.082*
C2	0.3983 (4)	0.2013 (3)	0.1530 (5)	0.0724 (12)
H2	0.4193	0.1322	0.1654	0.087*
C3	0.2500 (4)	0.3333 (3)	0.1698 (5)	0.0650 (10)
H3A	0.1651	0.3589	0.1953	0.078*
C4	0.3470 (3)	0.4010 (3)	0.1077 (4)	0.0530 (9)
C5	0.1935 (4)	0.5509 (3)	0.1131 (5)	0.0642 (10)
H5A	0.1176	0.5081	0.0658	0.077*
H5B	0.1875	0.6149	0.0508	0.077*
C6	0.1742 (3)	0.5727 (2)	0.2970 (5)	0.0521 (9)
C7	0.2751 (4)	0.5529 (3)	0.4289 (5)	0.0649 (11)
H7	0.3577	0.5226	0.4051	0.078*
C8	0.2562 (5)	0.5771 (3)	0.5957 (6)	0.0791 (13)
H8	0.3241	0.5620	0.6839	0.095*
C9	0.1347 (5)	0.6239 (3)	0.6285 (5)	0.0824 (13)
H9	0.1218	0.6427	0.7396	0.099*
C10	0.0329 (4)	0.6431 (3)	0.5000 (5)	0.0697 (11)
H10	−0.0494	0.6737	0.5242	0.084*
C11	0.0521 (4)	0.6171 (2)	0.3347 (5)	0.0524 (9)
H1	−0.116 (2)	0.661 (2)	0.239 (5)	0.077 (13)*
H3	0.388 (3)	0.538 (2)	0.040 (4)	0.070 (12)*

	U11	U22	U33	U12	U13	U23
O1	0.0572 (17)	0.0852 (18)	0.0555 (17)	0.0224 (13)	0.0117 (14)	−0.0003 (13)
N1	0.0494 (18)	0.0610 (19)	0.065 (2)	0.0002 (13)	0.0146 (15)	0.0000 (15)
N2	0.071 (2)	0.071 (2)	0.065 (2)	−0.0179 (17)	0.0064 (19)	0.0054 (16)
N3	0.054 (2)	0.066 (2)	0.080 (2)	0.0043 (16)	0.0281 (18)	0.0083 (17)
C1	0.060 (2)	0.069 (3)	0.078 (3)	0.0030 (19)	0.015 (2)	−0.002 (2)
C2	0.074 (3)	0.066 (2)	0.078 (3)	−0.004 (2)	0.010 (2)	0.004 (2)
C3	0.051 (2)	0.082 (3)	0.064 (3)	−0.0058 (19)	0.017 (2)	0.004 (2)
C4	0.046 (2)	0.066 (2)	0.048 (2)	−0.0072 (16)	0.0078 (17)	−0.0019 (17)
C5	0.054 (2)	0.077 (2)	0.064 (3)	0.0078 (18)	0.016 (2)	0.0054 (19)
C6	0.051 (2)	0.0549 (19)	0.051 (2)	−0.0027 (16)	0.0072 (18)	0.0043 (16)
C7	0.055 (2)	0.071 (2)	0.068 (3)	−0.0020 (18)	0.001 (2)	0.001 (2)
C8	0.087 (3)	0.084 (3)	0.063 (3)	−0.006 (2)	−0.015 (3)	0.004 (2)
C9	0.112 (4)	0.087 (3)	0.049 (3)	0.007 (3)	0.008 (3)	−0.012 (2)
C10	0.084 (3)	0.077 (3)	0.050 (3)	0.016 (2)	0.017 (2)	−0.001 (2)
C11	0.058 (2)	0.051 (2)	0.049 (2)	0.0017 (16)	0.0087 (19)	0.0025 (16)

O1—C11	1.363 (4)	C5—C6	1.507 (5)
O1—H1	0.844 (10)	C5—H5A	0.9700
N1—C4	1.336 (4)	C5—H5B	0.9700
N1—C1	1.337 (4)	C6—C7	1.379 (5)
N2—C3	1.311 (4)	C6—C11	1.379 (5)
N2—C2	1.337 (4)	C7—C8	1.382 (5)
N3—C4	1.345 (4)	C7—H7	0.9300
N3—C5	1.449 (4)	C8—C9	1.375 (6)
N3—H3	0.888 (10)	C8—H8	0.9300
C1—C2	1.361 (5)	C9—C10	1.365 (5)
C1—H1A	0.9300	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.377 (5)
C3—C4	1.415 (5)	C10—H10	0.9300
C3—H3A	0.9300
C11—O1—H1	109 (3)	N3—C5—H5B	108.4
C4—N1—C1	116.2 (3)	C6—C5—H5B	108.4
C3—N2—C2	117.3 (3)	H5A—C5—H5B	107.5
C4—N3—C5	123.9 (3)	C7—C6—C11	118.5 (3)
C4—N3—H3	117 (2)	C7—C6—C5	122.8 (3)
C5—N3—H3	119 (2)	C11—C6—C5	118.6 (3)
N1—C1—C2	123.6 (3)	C6—C7—C8	121.4 (4)
N1—C1—H1A	118.2	C6—C7—H7	119.3
C2—C1—H1A	118.2	C8—C7—H7	119.3
N2—C2—C1	120.7 (4)	C9—C8—C7	118.6 (4)
N2—C2—H2	119.7	C9—C8—H8	120.7
C1—C2—H2	119.7	C7—C8—H8	120.7
N2—C3—C4	122.3 (3)	C10—C9—C8	120.9 (4)
N2—C3—H3A	118.9	C10—C9—H9	119.6
C4—C3—H3A	118.9	C8—C9—H9	119.6
N1—C4—N3	116.9 (3)	C9—C10—C11	120.0 (4)
N1—C4—C3	120.0 (3)	C9—C10—H10	120.0
N3—C4—C3	123.2 (3)	C11—C10—H10	120.0
N3—C5—C6	115.4 (3)	O1—C11—C10	122.6 (3)
N3—C5—H5A	108.4	O1—C11—C6	116.8 (3)
C6—C5—H5A	108.4	C10—C11—C6	120.5 (4)
C4—N1—C1—C2	0.4 (6)	N3—C5—C6—C11	−178.2 (3)
C3—N2—C2—C1	1.3 (6)	C11—C6—C7—C8	−0.4 (5)
N1—C1—C2—N2	−1.2 (7)	C5—C6—C7—C8	177.7 (3)
C2—N2—C3—C4	−0.7 (6)	C6—C7—C8—C9	−1.4 (6)
C1—N1—C4—N3	179.9 (3)	C7—C8—C9—C10	2.2 (6)
C1—N1—C4—C3	0.2 (5)	C8—C9—C10—C11	−1.2 (6)
C5—N3—C4—N1	177.9 (3)	C9—C10—C11—O1	178.8 (3)
C5—N3—C4—C3	−2.5 (6)	C9—C10—C11—C6	−0.7 (6)
N2—C3—C4—N1	−0.1 (6)	C7—C6—C11—O1	−178.0 (3)
N2—C3—C4—N3	−179.7 (4)	C5—C6—C11—O1	3.8 (4)
C4—N3—C5—C6	78.5 (5)	C7—C6—C11—C10	1.4 (5)
N3—C5—C6—C7	3.7 (5)	C5—C6—C11—C10	−176.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.84 (1)	1.96 (1)	2.796 (4)	174 (4)
N3—H3···N1ii	0.89 (1)	2.12 (1)	3.007 (4)	175 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2i	0.84 (1)	1.96 (1)	2.796 (4)	174 (4)
N3—H3⋯N1ii	0.89 (1)	2.12 (1)	3.007 (4)	175 (3)

Symmetry codes: (i) ; (ii) .