2-(Pyrimidin-2-yl-oxy)phenol.

The pyrimidine and benzene rings in the title compound, C(10)H(8)N(2)O(2), form a dihedral angle of 71.03 (7)°, with the roughly orthogonal benzene ring being folded towards one of the pyrimidine N atoms. In the crystal, pairs of O-H⋯N hydrogen bonds connect mol-ecules related by twofold symmetry into dimeric aggregates. These associate into a supra-molecular chain propagating along the b axis by way of C-H⋯π contacts. The chains are cross-linked by π-π inter-actions that occur between pyrimidine rings [ring centroid-centroid distances = 3.5393 (9) and 3.5697 (9) Å].

Related literature

For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001 ▶); Abdullah (2005 ▶). For a related structure, see: Nasir et al. (2010 ▶).

Experimental

Crystal data

C10H8N2O2

M = 188.18

Monoclinic,

a = 18.0849 (18) Å

b = 7.3293 (8) Å

c = 13.3983 (14) Å

β = 92.521 (1)°

V = 1774.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.32 × 0.30 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.901, T max = 1.000

8265 measured reflections

2048 independent reflections

1569 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.112

S = 1.01

2048 reflections

130 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030448/hb5592sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030448/hb5592Isup2.hkl

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

C10H8N2O2	F(000) = 784
Mr = 188.18	Dx = 1.409 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2567 reflections
a = 18.0849 (18) Å	θ = 3.0–26.9°
b = 7.3293 (8) Å	µ = 0.10 mm−1
c = 13.3983 (14) Å	T = 293 K
β = 92.521 (1)°	Block, colourless
V = 1774.2 (3) Å3	0.32 × 0.30 × 0.10 mm
Z = 8

Bruker SMART APEX CCD diffractometer	2048 independent reflections
Radiation source: fine-focus sealed tube	1569 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.901, Tmax = 1.000	k = −9→9
8265 measured reflections	l = −17→15

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.4928P] where P = (Fo2 + 2Fc2)/3
2048 reflections	(Δ/σ)max = 0.001
130 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

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
O1	0.44378 (5)	0.18501 (12)	0.65018 (7)	0.0445 (3)
O2	0.38586 (6)	0.06384 (16)	0.82550 (8)	0.0622 (3)
H2o	0.4144 (10)	0.156 (2)	0.8229 (16)	0.093*
N1	0.39630 (6)	0.47232 (14)	0.61828 (9)	0.0431 (3)
N2	0.52544 (6)	0.41044 (15)	0.63993 (8)	0.0423 (3)
C1	0.45408 (7)	0.36583 (16)	0.63476 (9)	0.0356 (3)
C2	0.41257 (8)	0.64865 (19)	0.60601 (12)	0.0523 (4)
H2	0.3740	0.7306	0.5935	0.063*
C3	0.48369 (9)	0.71379 (19)	0.61104 (12)	0.0542 (4)
H3	0.4940	0.8371	0.6031	0.065*
C4	0.53883 (8)	0.5881 (2)	0.62839 (10)	0.0491 (3)
H4	0.5877	0.6283	0.6323	0.059*
C5	0.37173 (7)	0.11373 (16)	0.64788 (10)	0.0396 (3)
C6	0.33142 (8)	0.09337 (19)	0.55923 (12)	0.0537 (4)
H6	0.3495	0.1381	0.5001	0.064*
C7	0.26364 (9)	0.0057 (2)	0.55871 (14)	0.0651 (5)
H7	0.2356	−0.0076	0.4993	0.078*
C8	0.23810 (8)	−0.0614 (2)	0.64619 (15)	0.0653 (5)
H8	0.1927	−0.1212	0.6456	0.078*
C9	0.27880 (8)	−0.0416 (2)	0.73537 (13)	0.0575 (4)
H9	0.2609	−0.0885	0.7941	0.069*
C10	0.34627 (7)	0.04819 (17)	0.73708 (11)	0.0438 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0343 (5)	0.0366 (5)	0.0623 (6)	0.0010 (4)	−0.0025 (4)	0.0077 (4)
O2	0.0621 (7)	0.0705 (7)	0.0534 (6)	−0.0158 (5)	−0.0041 (5)	0.0089 (5)
N1	0.0372 (6)	0.0360 (6)	0.0557 (7)	0.0015 (4)	−0.0036 (5)	−0.0019 (5)
N2	0.0337 (6)	0.0490 (6)	0.0441 (6)	−0.0023 (5)	0.0010 (4)	0.0043 (5)
C1	0.0352 (6)	0.0372 (6)	0.0343 (6)	−0.0008 (5)	−0.0012 (5)	0.0006 (5)
C2	0.0516 (8)	0.0359 (7)	0.0686 (10)	0.0031 (6)	−0.0070 (7)	−0.0024 (6)
C3	0.0606 (9)	0.0385 (7)	0.0634 (9)	−0.0089 (6)	0.0005 (7)	0.0007 (6)
C4	0.0423 (7)	0.0553 (8)	0.0499 (8)	−0.0131 (6)	0.0026 (6)	0.0023 (6)
C5	0.0336 (6)	0.0292 (6)	0.0554 (8)	0.0001 (5)	−0.0040 (5)	0.0032 (5)
C6	0.0587 (9)	0.0440 (8)	0.0570 (9)	−0.0057 (6)	−0.0124 (7)	0.0083 (6)
C7	0.0621 (10)	0.0485 (8)	0.0818 (12)	−0.0098 (7)	−0.0306 (9)	0.0079 (8)
C8	0.0411 (8)	0.0475 (8)	0.1058 (14)	−0.0096 (6)	−0.0125 (8)	0.0084 (9)
C9	0.0461 (8)	0.0508 (9)	0.0759 (11)	−0.0063 (6)	0.0066 (7)	0.0076 (7)
C10	0.0397 (7)	0.0364 (6)	0.0550 (8)	0.0006 (5)	−0.0014 (6)	0.0018 (6)

O1—C1	1.3554 (15)	C4—H4	0.9300
O1—C5	1.4029 (14)	C5—C6	1.3741 (18)
O2—C10	1.3619 (17)	C5—C10	1.385 (2)
O2—H2o	0.852 (16)	C6—C7	1.384 (2)
N1—C1	1.3151 (16)	C6—H6	0.9300
N1—C2	1.3372 (17)	C7—C8	1.370 (3)
N2—C1	1.3302 (16)	C7—H7	0.9300
N2—C4	1.3347 (18)	C8—C9	1.383 (2)
C2—C3	1.371 (2)	C8—H8	0.9300
C2—H2	0.9300	C9—C10	1.3857 (19)
C3—C4	1.370 (2)	C9—H9	0.9300
C3—H3	0.9300
C1—O1—C5	119.64 (9)	C6—C5—O1	121.09 (12)
C10—O2—H2o	109.1 (15)	C10—C5—O1	116.98 (11)
C1—N1—C2	114.63 (11)	C5—C6—C7	119.40 (14)
C1—N2—C4	114.48 (11)	C5—C6—H6	120.3
N1—C1—N2	128.66 (12)	C7—C6—H6	120.3
N1—C1—O1	119.50 (11)	C8—C7—C6	119.62 (15)
N2—C1—O1	111.84 (10)	C8—C7—H7	120.2
N1—C2—C3	122.80 (13)	C6—C7—H7	120.2
N1—C2—H2	118.6	C7—C8—C9	120.99 (14)
C3—C2—H2	118.6	C7—C8—H8	119.5
C4—C3—C2	116.65 (13)	C9—C8—H8	119.5
C4—C3—H3	121.7	C8—C9—C10	119.92 (15)
C2—C3—H3	121.7	C8—C9—H9	120.0
N2—C4—C3	122.77 (13)	C10—C9—H9	120.0
N2—C4—H4	118.6	O2—C10—C5	122.64 (12)
C3—C4—H4	118.6	O2—C10—C9	118.89 (13)
C6—C5—C10	121.62 (12)	C5—C10—C9	118.44 (13)
C2—N1—C1—N2	−0.6 (2)	C10—C5—C6—C7	0.1 (2)
C2—N1—C1—O1	178.72 (12)	O1—C5—C6—C7	173.48 (13)
C4—N2—C1—N1	1.30 (19)	C5—C6—C7—C8	−0.8 (2)
C4—N2—C1—O1	−178.02 (11)	C6—C7—C8—C9	0.5 (3)
C5—O1—C1—N1	0.31 (17)	C7—C8—C9—C10	0.4 (2)
C5—O1—C1—N2	179.70 (10)	C6—C5—C10—O2	178.77 (13)
C1—N1—C2—C3	−0.5 (2)	O1—C5—C10—O2	5.17 (18)
N1—C2—C3—C4	0.7 (2)	C6—C5—C10—C9	0.8 (2)
C1—N2—C4—C3	−1.0 (2)	O1—C5—C10—C9	−172.84 (12)
C2—C3—C4—N2	0.1 (2)	C8—C9—C10—O2	−179.10 (14)
C1—O1—C5—C6	73.64 (16)	C8—C9—C10—C5	−1.0 (2)
C1—O1—C5—C10	−112.73 (13)

Cg1 is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···N2i	0.85 (2)	2.21 (1)	3.0292 (16)	163 (2)
C2—H2···Cg1ii	0.93	2.62	3.4424 (16)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯N2i	0.85 (2)	2.21 (1)	3.0292 (16)	163 (2)
C2—H2⋯Cg1ii	0.93	2.62	3.4424 (16)	148

Symmetry codes: (i) ; (ii) .