2-[(Pyrimidin-2-yl-amino)-meth-yl]phenol.

In the title compound, C(11)H(11)N(3)O, the aromatic rings at either ends of the -CH(2)-NH- link are twisted by 72.58 (8)°; the hy-droxy substituent is a hydrogen-bond donor to an N atom of the pyrimidine ring. The other N atom of the pyrimidine ring is a hydrogen-bond acceptor to the amino group of an inversion-related mol-ecule.

Related literature

For the N-salicyl­idene-2-amino­pyrimidine precursor, see: El-Haty et al. (1990 ▶); Issa et al. (2011 ▶); Shalabi & Abdel-Ghani (1990 ▶). For a related structure, see: Xu et al. (2011 ▶).

Experimental

Crystal data

C11H11N3O

M = 201.23

Monoclinic,

a = 5.8625 (4) Å

b = 9.3610 (7) Å

c = 18.4058 (13) Å

β = 95.208 (2)°

V = 1005.92 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.22 × 0.17 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.981, T max = 0.987

9626 measured reflections

2296 independent reflections

1476 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.149

S = 1.12

2296 reflections

144 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.15 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/S1600536811046848/xu5383sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046848/xu5383Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046848/xu5383Isup3.cml

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

C11H11N3O	F(000) = 424
Mr = 201.23	Dx = 1.329 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6005 reflections
a = 5.8625 (4) Å	θ = 3.1–27.4°
b = 9.3610 (7) Å	µ = 0.09 mm−1
c = 18.4058 (13) Å	T = 293 K
β = 95.208 (2)°	Prism, colorless
V = 1005.92 (12) Å3	0.22 × 0.17 × 0.15 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	2296 independent reflections
Radiation source: fine-focus sealed tube	1476 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scan	θmax = 27.4°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→6
Tmin = 0.981, Tmax = 0.987	k = −12→12
9626 measured reflections	l = −23→23

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0796P)2 + 0.034P] where P = (Fo2 + 2Fc2)/3
2296 reflections	(Δ/σ)max = 0.001
144 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.15 e Å−3

	x	y	z	Uiso*/Ueq
O1	1.0476 (2)	0.91985 (13)	0.62203 (7)	0.0630 (4)
N1	0.5979 (2)	0.67826 (16)	0.53868 (8)	0.0571 (4)
N2	0.9251 (2)	0.77099 (14)	0.49494 (7)	0.0534 (4)
N3	0.7438 (2)	0.55875 (14)	0.44465 (7)	0.0517 (4)
C1	0.9836 (3)	0.82174 (16)	0.67131 (9)	0.0488 (4)
C2	1.1341 (3)	0.79323 (18)	0.73237 (9)	0.0554 (4)
H2	1.2718	0.8428	0.7393	0.066*
C3	1.0819 (3)	0.69305 (19)	0.78229 (10)	0.0622 (5)
H3	1.1850	0.6737	0.8225	0.075*
C4	0.8756 (3)	0.62029 (19)	0.77307 (10)	0.0646 (5)
H4	0.8405	0.5512	0.8066	0.078*
C5	0.7224 (3)	0.65110 (18)	0.71357 (10)	0.0581 (4)
H5	0.5827	0.6034	0.7081	0.070*
C6	0.7718 (2)	0.75136 (16)	0.66180 (9)	0.0500 (4)
C7	0.5997 (3)	0.78265 (19)	0.59729 (9)	0.0580 (4)
H7A	0.4480	0.7868	0.6143	0.070*
H7B	0.6329	0.8760	0.5779	0.070*
C8	0.7604 (2)	0.66981 (16)	0.49207 (8)	0.0478 (4)
C9	1.0801 (3)	0.75831 (19)	0.44642 (10)	0.0574 (4)
H9	1.1954	0.8266	0.4466	0.069*
C10	1.0780 (3)	0.65013 (19)	0.39651 (9)	0.0593 (5)
H10	1.1880	0.6432	0.3633	0.071*
C11	0.9034 (3)	0.55172 (19)	0.39818 (9)	0.0550 (4)
H11	0.8973	0.4766	0.3650	0.066*
H1O	1.000 (4)	0.889 (3)	0.5791 (8)	0.117 (9)*
H1N	0.501 (3)	0.6073 (14)	0.5417 (10)	0.062 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0674 (8)	0.0543 (7)	0.0667 (8)	−0.0114 (5)	0.0032 (6)	0.0017 (6)
N1	0.0425 (7)	0.0658 (9)	0.0629 (8)	−0.0070 (6)	0.0040 (6)	−0.0127 (7)
N2	0.0488 (7)	0.0504 (8)	0.0601 (8)	−0.0022 (6)	0.0006 (6)	0.0040 (6)
N3	0.0495 (7)	0.0547 (8)	0.0500 (7)	0.0018 (6)	0.0006 (6)	−0.0008 (6)
C1	0.0492 (8)	0.0404 (8)	0.0572 (9)	0.0000 (6)	0.0070 (7)	−0.0069 (7)
C2	0.0488 (8)	0.0575 (10)	0.0590 (10)	−0.0035 (7)	−0.0001 (8)	−0.0112 (8)
C3	0.0656 (11)	0.0631 (11)	0.0563 (10)	0.0039 (8)	−0.0026 (8)	−0.0032 (8)
C4	0.0772 (12)	0.0569 (10)	0.0611 (10)	−0.0049 (9)	0.0134 (9)	0.0010 (8)
C5	0.0504 (9)	0.0557 (10)	0.0694 (11)	−0.0077 (7)	0.0120 (8)	−0.0116 (8)
C6	0.0427 (8)	0.0484 (9)	0.0591 (10)	0.0026 (6)	0.0064 (7)	−0.0118 (7)
C7	0.0446 (8)	0.0635 (10)	0.0652 (10)	0.0062 (7)	0.0016 (8)	−0.0130 (8)
C8	0.0426 (8)	0.0499 (9)	0.0494 (8)	0.0026 (6)	−0.0039 (7)	0.0025 (7)
C9	0.0523 (9)	0.0568 (10)	0.0629 (10)	−0.0025 (7)	0.0042 (8)	0.0124 (8)
C10	0.0572 (10)	0.0637 (11)	0.0581 (10)	0.0031 (8)	0.0100 (8)	0.0067 (8)
C11	0.0581 (9)	0.0561 (10)	0.0503 (9)	0.0067 (8)	0.0019 (8)	0.0012 (7)

O1—C1	1.367 (2)	C3—H3	0.9300
O1—H1O	0.863 (10)	C4—C5	1.382 (3)
N1—C8	1.341 (2)	C4—H4	0.9300
N1—C7	1.455 (2)	C5—C6	1.387 (2)
N1—H1N	0.878 (9)	C5—H5	0.9300
N2—C9	1.336 (2)	C6—C7	1.515 (2)
N2—C8	1.350 (2)	C7—H7A	0.9700
N3—C11	1.325 (2)	C7—H7B	0.9700
N3—C8	1.3552 (19)	C9—C10	1.367 (2)
C1—C2	1.390 (2)	C9—H9	0.9300
C1—C6	1.402 (2)	C10—C11	1.380 (2)
C2—C3	1.367 (2)	C10—H10	0.9300
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.385 (3)
C1—O1—H1O	107.4 (18)	C5—C6—C1	118.05 (15)
C8—N1—C7	123.78 (14)	C5—C6—C7	120.21 (15)
C8—N1—H1N	119.7 (12)	C1—C6—C7	121.74 (15)
C7—N1—H1N	115.0 (12)	N1—C7—C6	114.25 (13)
C9—N2—C8	116.03 (14)	N1—C7—H7A	108.7
C11—N3—C8	116.12 (14)	C6—C7—H7A	108.7
O1—C1—C2	118.23 (14)	N1—C7—H7B	108.7
O1—C1—C6	121.74 (14)	C6—C7—H7B	108.7
C2—C1—C6	120.03 (15)	H7A—C7—H7B	107.6
C3—C2—C1	120.70 (15)	N1—C8—N2	118.73 (14)
C3—C2—H2	119.7	N1—C8—N3	116.33 (14)
C1—C2—H2	119.7	N2—C8—N3	124.93 (15)
C2—C3—C4	120.10 (16)	N2—C9—C10	123.37 (16)
C2—C3—H3	120.0	N2—C9—H9	118.3
C4—C3—H3	120.0	C10—C9—H9	118.3
C5—C4—C3	119.47 (17)	C9—C10—C11	116.19 (16)
C5—C4—H4	120.3	C9—C10—H10	121.9
C3—C4—H4	120.3	C11—C10—H10	121.9
C4—C5—C6	121.60 (16)	N3—C11—C10	123.36 (16)
C4—C5—H5	119.2	N3—C11—H11	118.3
C6—C5—H5	119.2	C10—C11—H11	118.3
O1—C1—C2—C3	−178.05 (15)	C5—C6—C7—N1	−79.8 (2)
C6—C1—C2—C3	2.4 (2)	C1—C6—C7—N1	100.33 (18)
C1—C2—C3—C4	−1.1 (3)	C7—N1—C8—N2	−6.1 (2)
C2—C3—C4—C5	−0.8 (3)	C7—N1—C8—N3	174.43 (14)
C3—C4—C5—C6	1.4 (3)	C9—N2—C8—N1	−178.93 (13)
C4—C5—C6—C1	0.0 (2)	C9—N2—C8—N3	0.4 (2)
C4—C5—C6—C7	−179.92 (15)	C11—N3—C8—N1	179.28 (13)
O1—C1—C6—C5	178.65 (14)	C11—N3—C8—N2	−0.1 (2)
C2—C1—C6—C5	−1.8 (2)	C8—N2—C9—C10	−0.5 (2)
O1—C1—C6—C7	−1.5 (2)	N2—C9—C10—C11	0.2 (2)
C2—C1—C6—C7	178.06 (14)	C8—N3—C11—C10	−0.2 (2)
C8—N1—C7—C6	−74.7 (2)	C9—C10—C11—N3	0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N2	0.86 (1)	1.92 (1)	2.761 (2)	164 (2)
N1—H1n···N3i	0.88 (1)	2.15 (1)	3.023 (2)	176 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N2	0.86 (1)	1.92 (1)	2.761 (2)	164 (2)
N1—H1n⋯N3i	0.88 (1)	2.15 (1)	3.023 (2)	176 (2)

Symmetry code: (i) .