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

The planes of the aromatic rings of the title compound, C(12)H(12)N(2)O, are twisted by 50.33 (15)°. The phenol O atom is a hydrogen-bond donor to the pyridine N atom, resulting in the formation of an eight-membered ring in the mol-ecule. The amino N atom is a hydrogen-bond donor to the phenol O atom of an adjacent mol-ecule; this hydrogen bond leads to the formation of a helical chain that runs along the a axis.

Related literature

For the related compound 2-{[(pyrazin-2-yl)amino]­meth­yl}­phenol, see: Gao & Ng (2012 ▶). For 2-[(pyridin-3-yl­amino)­meth­yl]phenol, see: Xu et al. (2011 ▶). For the metal adducts of 2-[(pyridin-2-yl­amino)­meth­yl]phenol, see: Yalçın et al. (2007 ▶).

Experimental

Crystal data

C12H12N2O

M = 200.24

Orthorhombic,

a = 6.3331 (4) Å

b = 10.6761 (9) Å

c = 15.3714 (10) Å

V = 1039.30 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.25 × 0.19 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.979, T max = 0.988

10221 measured reflections

1391 independent reflections

887 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.131

S = 1.04

1391 reflections

144 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.18 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/S1600536812031340/xu5581sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031340/xu5581Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031340/xu5581Isup3.cml

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

C12H12N2O	F(000) = 424
Mr = 200.24	Dx = 1.280 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6231 reflections
a = 6.3331 (4) Å	θ = 3.3–27.4°
b = 10.6761 (9) Å	µ = 0.08 mm−1
c = 15.3714 (10) Å	T = 295 K
V = 1039.30 (13) Å3	Prism, faint yellow
Z = 4	0.25 × 0.19 × 0.15 mm

Rigaku R-AXIS RAPID IP diffractometer	1391 independent reflections
Radiation source: fine-focus sealed tube	887 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω scan	θmax = 27.4°, θmin = 3.3°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
Tmin = 0.979, Tmax = 0.988	k = −13→13
10221 measured reflections	l = −19→19

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0773P)2] where P = (Fo2 + 2Fc2)/3
1391 reflections	(Δ/σ)max = 0.001
144 parameters	Δρmax = 0.13 e Å−3
2 restraints	Δρmin = −0.18 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.6052 (3)	0.1233 (2)	0.18887 (14)	0.0752 (7)
N1	0.8839 (3)	0.0670 (2)	0.06566 (14)	0.0570 (6)
N2	1.1470 (4)	0.1185 (3)	0.16368 (15)	0.0672 (8)
C1	0.8251 (6)	0.0489 (3)	−0.01804 (18)	0.0672 (8)
H1A	0.6882	0.0212	−0.0286	0.081*
C2	0.9537 (6)	0.0687 (3)	−0.0877 (2)	0.0762 (9)
H2A	0.9069	0.0534	−0.1441	0.091*
C3	1.1575 (6)	0.1126 (3)	−0.0720 (2)	0.0706 (9)
H3	1.2483	0.1294	−0.1181	0.085*
C4	1.2220 (5)	0.1305 (3)	0.01124 (19)	0.0636 (8)
H4	1.3573	0.1600	0.0227	0.076*
C5	1.0823 (4)	0.1041 (3)	0.08020 (17)	0.0542 (7)
C6	1.0371 (5)	0.0617 (3)	0.23756 (18)	0.0652 (8)
H6A	1.1414	0.0269	0.2769	0.078*
H6B	0.9513	−0.0071	0.2163	0.078*
C7	0.8978 (4)	0.1498 (3)	0.28793 (17)	0.0564 (7)
C8	0.9675 (5)	0.2047 (3)	0.36466 (18)	0.0672 (9)
H8	1.1032	0.1872	0.3843	0.081*
C9	0.8415 (6)	0.2848 (3)	0.4129 (2)	0.0761 (9)
H9	0.8911	0.3193	0.4645	0.091*
C10	0.6432 (6)	0.3126 (3)	0.3835 (2)	0.0763 (10)
H10	0.5583	0.3673	0.4150	0.092*
C11	0.5680 (5)	0.2601 (3)	0.30782 (18)	0.0692 (8)
H11	0.4334	0.2801	0.2881	0.083*
C12	0.6935 (4)	0.1769 (3)	0.26072 (17)	0.0567 (7)
H1	0.694 (5)	0.093 (4)	0.153 (2)	0.119 (17)*
H2	1.2851 (18)	0.126 (4)	0.167 (2)	0.092 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0449 (10)	0.1083 (19)	0.0723 (13)	−0.0019 (12)	−0.0022 (11)	−0.0175 (13)
N1	0.0441 (11)	0.0614 (15)	0.0655 (13)	0.0003 (11)	−0.0053 (11)	−0.0049 (11)
N2	0.0426 (12)	0.099 (2)	0.0599 (14)	−0.0044 (13)	−0.0005 (11)	−0.0014 (13)
C1	0.0658 (18)	0.068 (2)	0.0680 (18)	−0.0014 (15)	−0.0109 (16)	−0.0112 (15)
C2	0.094 (2)	0.073 (2)	0.0620 (16)	−0.001 (2)	−0.0054 (19)	−0.0145 (16)
C3	0.084 (2)	0.064 (2)	0.0638 (18)	0.0032 (17)	0.0141 (16)	−0.0084 (14)
C4	0.0585 (16)	0.0609 (19)	0.0715 (19)	−0.0017 (15)	0.0113 (15)	−0.0067 (14)
C5	0.0471 (14)	0.0553 (17)	0.0601 (14)	0.0020 (13)	0.0012 (13)	−0.0030 (13)
C6	0.0544 (15)	0.078 (2)	0.0634 (16)	0.0060 (15)	−0.0075 (14)	0.0105 (15)
C7	0.0471 (14)	0.0667 (19)	0.0555 (14)	−0.0064 (13)	0.0017 (13)	0.0094 (13)
C8	0.0610 (17)	0.082 (2)	0.0581 (15)	−0.0153 (17)	−0.0026 (15)	0.0086 (15)
C9	0.090 (2)	0.077 (2)	0.0616 (16)	−0.022 (2)	0.0027 (18)	−0.0032 (17)
C10	0.087 (2)	0.071 (2)	0.0709 (18)	−0.0049 (19)	0.0184 (18)	−0.0051 (16)
C11	0.0581 (16)	0.078 (2)	0.0713 (17)	0.0046 (17)	0.0107 (15)	0.0055 (17)
C12	0.0497 (14)	0.0644 (19)	0.0561 (15)	−0.0075 (13)	0.0031 (13)	−0.0002 (13)

O1—C12	1.364 (3)	C4—H4	0.9300
O1—H1	0.851 (10)	C6—C7	1.504 (4)
N1—C5	1.336 (4)	C6—H6A	0.9700
N1—C1	1.353 (3)	C6—H6B	0.9700
N2—C5	1.356 (3)	C7—C8	1.389 (4)
N2—C6	1.464 (4)	C7—C12	1.390 (4)
N2—H2	0.879 (10)	C8—C9	1.384 (5)
C1—C2	1.362 (5)	C8—H8	0.9300
C1—H1A	0.9300	C9—C10	1.367 (5)
C2—C3	1.395 (5)	C9—H9	0.9300
C2—H2A	0.9300	C10—C11	1.377 (4)
C3—C4	1.357 (4)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.394 (4)
C4—C5	1.409 (4)	C11—H11	0.9300
C12—O1—H1	114 (3)	C7—C6—H6A	108.6
C5—N1—C1	117.4 (3)	N2—C6—H6B	108.6
C5—N2—C6	122.9 (3)	C7—C6—H6B	108.6
C5—N2—H2	111 (2)	H6A—C6—H6B	107.5
C6—N2—H2	118 (2)	C8—C7—C12	117.6 (3)
N1—C1—C2	124.1 (3)	C8—C7—C6	121.0 (3)
N1—C1—H1A	118.0	C12—C7—C6	121.4 (3)
C2—C1—H1A	118.0	C9—C8—C7	122.1 (3)
C1—C2—C3	118.0 (3)	C9—C8—H8	118.9
C1—C2—H2A	121.0	C7—C8—H8	118.9
C3—C2—H2A	121.0	C10—C9—C8	119.1 (3)
C4—C3—C2	119.3 (3)	C10—C9—H9	120.4
C4—C3—H3	120.4	C8—C9—H9	120.4
C2—C3—H3	120.4	C9—C10—C11	120.5 (3)
C3—C4—C5	119.5 (3)	C9—C10—H10	119.7
C3—C4—H4	120.2	C11—C10—H10	119.7
C5—C4—H4	120.2	C10—C11—C12	120.1 (3)
N1—C5—N2	118.4 (2)	C10—C11—H11	120.0
N1—C5—C4	121.6 (3)	C12—C11—H11	120.0
N2—C5—C4	120.0 (2)	O1—C12—C7	122.5 (3)
N2—C6—C7	114.8 (3)	O1—C12—C11	117.0 (3)
N2—C6—H6A	108.6	C7—C12—C11	120.5 (3)
C5—N1—C1—C2	−1.4 (5)	N2—C6—C7—C12	82.9 (4)
N1—C1—C2—C3	−1.3 (5)	C12—C7—C8—C9	−0.6 (4)
C1—C2—C3—C4	1.8 (5)	C6—C7—C8—C9	−179.1 (3)
C2—C3—C4—C5	0.2 (5)	C7—C8—C9—C10	−1.1 (5)
C1—N1—C5—N2	−177.7 (3)	C8—C9—C10—C11	1.1 (5)
C1—N1—C5—C4	3.6 (4)	C9—C10—C11—C12	0.6 (5)
C6—N2—C5—N1	18.7 (5)	C8—C7—C12—O1	−176.6 (3)
C6—N2—C5—C4	−162.5 (3)	C6—C7—C12—O1	1.9 (4)
C3—C4—C5—N1	−3.0 (5)	C8—C7—C12—C11	2.3 (4)
C3—C4—C5—N2	178.2 (3)	C6—C7—C12—C11	−179.2 (3)
C5—N2—C6—C7	−101.6 (3)	C10—C11—C12—O1	176.6 (3)
N2—C6—C7—C8	−98.6 (3)	C10—C11—C12—C7	−2.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.85 (1)	1.83 (2)	2.658 (3)	166 (5)
N2—H2···O1i	0.88 (1)	2.06 (1)	2.928 (3)	172 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.85 (1)	1.83 (2)	2.658 (3)	166 (5)
N2—H2⋯O1i	0.88 (1)	2.06 (1)	2.928 (3)	172 (3)

Symmetry code: (i) .