2-[(Pyridin-3-yl-amino)-meth-yl]phenol.

In the title compound, C(12)H(12)N(2)O, the aromatic rings at either ends of the -CH(2)-NH- link are twisted by 68.79 (7)°. In the crystal, the hy-droxy substituent is a hydrogen-bond donor to the N atom of the pyridine ring of an adjacent mol-ecule, and the hydrogen bond generates a chain along the b axis; it is also a hydrogen-bond acceptor to the amino group of another adjacent mol-ecule. The two hydrogen bonds lead to the formation of a layer structure.

Related literature

For the N-salicyl­idene-3-amino­n class="Chemical">pyridine precursor, see: Csaszar (1990 ▶); Kaya & Guelel (2005 ▶); Robert et al. (2009 ▶). For a related structure, see: Xu et al. (2011 ▶).

Experimental

Crystal data

C12H12N2O

M = 200.24

Monoclinic,

a = 5.8386 (11) Å

b = 13.399 (3) Å

c = 13.169 (3) Å

β = 90.519 (6)°

V = 1030.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.21 × 0.12 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.983, T max = 0.990

9845 measured reflections

2358 independent reflections

1879 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.137

S = 1.08

2358 reflections

144 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 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/S160053681104685X/xu5384sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104685X/xu5384Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104685X/xu5384Isup3.cml

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

C12H12N2O	F(000) = 424
Mr = 200.24	Dx = 1.291 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5377 reflections
a = 5.8386 (11) Å	θ = 3.0–27.5°
b = 13.399 (3) Å	µ = 0.08 mm−1
c = 13.169 (3) Å	T = 293 K
β = 90.519 (6)°	Prism, colorless
V = 1030.1 (4) Å3	0.21 × 0.12 × 0.12 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2358 independent reflections
Radiation source: fine-focus sealed tube	1879 reflections with I > 2σ(I)
graphite	Rint = 0.042
ω scan	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→7
Tmin = 0.983, Tmax = 0.990	k = −17→17
9845 measured reflections	l = −17→16

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0752P)2 + 0.0952P] where P = (Fo2 + 2Fc2)/3
2358 reflections	(Δ/σ)max = 0.001
144 parameters	Δρmax = 0.26 e Å−3
2 restraints	Δρmin = −0.18 e Å−3

	x	y	z	Uiso*/Ueq
O1	1.17862 (17)	0.30493 (7)	0.38420 (7)	0.0517 (3)
H1O	1.249 (3)	0.2486 (9)	0.3790 (12)	0.073 (5)*
N1	0.6391 (2)	0.42170 (9)	0.32008 (9)	0.0512 (3)
H1N	0.534 (2)	0.3813 (10)	0.3444 (11)	0.059 (4)*
N2	0.61025 (18)	0.63154 (8)	0.14353 (8)	0.0493 (3)
C1	1.0374 (2)	0.30367 (9)	0.46539 (9)	0.0396 (3)
C2	1.0673 (2)	0.23629 (11)	0.54458 (10)	0.0499 (3)
H2	1.1882	0.1911	0.5429	0.060*
C3	0.9202 (3)	0.23577 (13)	0.62516 (10)	0.0591 (4)
H3	0.9407	0.1897	0.6773	0.071*
C4	0.7428 (3)	0.30289 (14)	0.62928 (11)	0.0669 (5)
H4	0.6418	0.3022	0.6835	0.080*
C5	0.7166 (3)	0.37110 (12)	0.55208 (11)	0.0597 (4)
H5	0.5982	0.4173	0.5557	0.072*
C6	0.8605 (2)	0.37334 (9)	0.46929 (9)	0.0431 (3)
C7	0.8270 (2)	0.44915 (10)	0.38681 (11)	0.0484 (3)
H7A	0.7961	0.5138	0.4169	0.058*
H7B	0.9664	0.4547	0.3477	0.058*
C8	0.5640 (2)	0.48446 (9)	0.24474 (9)	0.0416 (3)
C9	0.6833 (2)	0.57012 (10)	0.21638 (10)	0.0449 (3)
H9	0.8200	0.5850	0.2499	0.054*
C10	0.4163 (2)	0.61131 (11)	0.09441 (11)	0.0545 (4)
H10	0.3659	0.6543	0.0434	0.065*
C11	0.2877 (2)	0.52808 (12)	0.11717 (11)	0.0586 (4)
H11	0.1522	0.5152	0.0819	0.070*
C12	0.3611 (2)	0.46471 (11)	0.19197 (10)	0.0528 (4)
H12	0.2755	0.4083	0.2077	0.063*

	U11	U22	U33	U12	U13	U23
O1	0.0596 (6)	0.0440 (5)	0.0517 (6)	0.0094 (4)	0.0165 (5)	0.0042 (4)
N1	0.0588 (7)	0.0428 (6)	0.0519 (6)	−0.0104 (5)	−0.0083 (5)	0.0094 (5)
N2	0.0515 (6)	0.0442 (6)	0.0522 (6)	−0.0019 (5)	0.0093 (5)	0.0090 (5)
C1	0.0424 (6)	0.0385 (6)	0.0380 (6)	0.0015 (5)	0.0016 (5)	−0.0046 (5)
C2	0.0494 (7)	0.0527 (8)	0.0476 (7)	0.0131 (6)	0.0022 (6)	0.0037 (6)
C3	0.0645 (9)	0.0721 (10)	0.0408 (7)	0.0146 (7)	0.0030 (6)	0.0107 (6)
C4	0.0663 (9)	0.0880 (12)	0.0467 (8)	0.0213 (8)	0.0168 (7)	0.0033 (7)
C5	0.0570 (8)	0.0670 (10)	0.0551 (8)	0.0241 (7)	0.0097 (7)	−0.0013 (7)
C6	0.0448 (6)	0.0413 (7)	0.0432 (6)	0.0053 (5)	−0.0032 (5)	−0.0040 (5)
C7	0.0465 (7)	0.0396 (7)	0.0589 (8)	0.0025 (5)	−0.0045 (6)	0.0019 (6)
C8	0.0473 (6)	0.0377 (6)	0.0400 (6)	−0.0011 (5)	0.0038 (5)	−0.0009 (5)
C9	0.0403 (6)	0.0434 (7)	0.0511 (7)	−0.0022 (5)	0.0045 (5)	0.0029 (5)
C10	0.0592 (8)	0.0578 (8)	0.0465 (7)	0.0034 (6)	0.0008 (6)	0.0120 (6)
C11	0.0558 (8)	0.0701 (10)	0.0498 (8)	−0.0095 (7)	−0.0094 (6)	0.0057 (7)
C12	0.0584 (8)	0.0518 (8)	0.0481 (7)	−0.0169 (6)	−0.0026 (6)	0.0037 (6)

O1—C1	1.3562 (15)	C4—H4	0.9300
O1—H1O	0.86 (1)	C5—C6	1.383 (2)
N1—C8	1.3695 (16)	C5—H5	0.9300
N1—C7	1.4472 (17)	C6—C7	1.4986 (17)
N1—H1N	0.88 (1)	C7—H7A	0.9700
N2—C10	1.3269 (18)	C7—H7B	0.9700
N2—C9	1.3312 (16)	C8—C12	1.3936 (18)
C1—C2	1.3892 (18)	C8—C9	1.3953 (18)
C1—C6	1.3933 (17)	C9—H9	0.9300
C2—C3	1.371 (2)	C10—C11	1.379 (2)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.373 (2)	C11—C12	1.366 (2)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.374 (2)	C12—H12	0.9300
C1—O1—H1O	110.3 (12)	C1—C6—C7	121.29 (12)
C8—N1—C7	121.31 (11)	N1—C7—C6	111.17 (11)
C8—N1—H1N	114.9 (10)	N1—C7—H7A	109.4
C7—N1—H1N	117.6 (10)	C6—C7—H7A	109.4
C10—N2—C9	119.43 (11)	N1—C7—H7B	109.4
O1—C1—C2	121.78 (11)	C6—C7—H7B	109.4
O1—C1—C6	118.47 (11)	H7A—C7—H7B	108.0
C2—C1—C6	119.73 (12)	N1—C8—C12	120.65 (11)
C3—C2—C1	120.58 (12)	N1—C8—C9	122.81 (11)
C3—C2—H2	119.7	C12—C8—C9	116.54 (12)
C1—C2—H2	119.7	N2—C9—C8	122.96 (12)
C2—C3—C4	120.35 (13)	N2—C9—H9	118.5
C2—C3—H3	119.8	C8—C9—H9	118.5
C4—C3—H3	119.8	N2—C10—C11	121.55 (12)
C3—C4—C5	119.01 (14)	N2—C10—H10	119.2
C3—C4—H4	120.5	C11—C10—H10	119.2
C5—C4—H4	120.5	C12—C11—C10	119.44 (13)
C4—C5—C6	122.24 (13)	C12—C11—H11	120.3
C4—C5—H5	118.9	C10—C11—H11	120.3
C6—C5—H5	118.9	C11—C12—C8	120.07 (12)
C5—C6—C1	118.05 (12)	C11—C12—H12	120.0
C5—C6—C7	120.66 (11)	C8—C12—H12	120.0
O1—C1—C2—C3	−179.14 (13)	C5—C6—C7—N1	−77.50 (16)
C6—C1—C2—C3	1.9 (2)	C1—C6—C7—N1	102.91 (14)
C1—C2—C3—C4	−0.9 (2)	C7—N1—C8—C12	−169.54 (13)
C2—C3—C4—C5	−0.7 (3)	C7—N1—C8—C9	10.6 (2)
C3—C4—C5—C6	1.2 (3)	C10—N2—C9—C8	−0.4 (2)
C4—C5—C6—C1	−0.2 (2)	N1—C8—C9—N2	−179.66 (12)
C4—C5—C6—C7	−179.76 (14)	C12—C8—C9—N2	0.5 (2)
O1—C1—C6—C5	179.63 (12)	C9—N2—C10—C11	0.2 (2)
C2—C1—C6—C5	−1.41 (19)	N2—C10—C11—C12	0.0 (2)
O1—C1—C6—C7	−0.77 (17)	C10—C11—C12—C8	0.1 (2)
C2—C1—C6—C7	178.19 (11)	N1—C8—C12—C11	179.81 (14)
C8—N1—C7—C6	174.01 (12)	C9—C8—C12—C11	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N2i	0.862 (14)	1.797 (14)	2.6568 (16)	175.0 (16)
N1—H1n···O1ii	0.881 (13)	2.376 (12)	3.2296 (17)	163.2 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N2i	0.86 (1)	1.80 (1)	2.6568 (16)	175 (2)
N1—H1n⋯O1ii	0.88 (1)	2.38 (1)	3.2296 (17)	163 (1)

Symmetry codes: (i) ; (ii) .