3-Fluoro-4-(4-hy-droxy-phen-oxy)benzonitrile.

The title compound, C(13)H(8)FNO(2), was synthesized from 3,4-difluoro-benzonitrile and hydro-quinone. The dihedral angle between the two aromatic rings is 70.9 (2)°. In the crystal structure, mol-ecules are linked by O-H⋯N hydrogen bonds, forming zigzag chains.

Related literature

For the herbicidal actvity of hydro­quinone derivatives, see: Bao et al. (2007 ▶); Liu (2002 ▶). For related structures, see: Sørensen et al. (2009 ▶); Luo et al. (2009 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C13H8FNO2

M = 229.20

Orthorhombic,

a = 6.1932 (4) Å

b = 8.8109 (5) Å

c = 20.5269 (12) Å

V = 1120.11 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.39 × 0.31 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.959, T max = 0.976

10999 measured reflections

1498 independent reflections

928 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.117

S = 1.01

1498 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia,1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810024360/im2202sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024360/im2202Isup2.hkl

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

C13H8FNO2	F(000) = 472
Mr = 229.20	Dx = 1.359 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6842 reflections
a = 6.1932 (4) Å	θ = 3.0–27.4°
b = 8.8109 (5) Å	µ = 0.10 mm−1
c = 20.5269 (12) Å	T = 295 K
V = 1120.11 (12) Å3	Chunk, colorless
Z = 4	0.39 × 0.31 × 0.22 mm

Rigaku R-AXIS RAPID diffractometer	1498 independent reflections
Radiation source: rolling anode	928 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
Tmin = 0.959, Tmax = 0.976	l = −26→26
10999 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.2503P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1498 reflections	Δρmax = 0.17 e Å−3
156 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.8260 (4)	0.8262 (3)	0.91021 (10)	0.0842 (7)
F1	0.7477 (4)	0.5751 (2)	0.84401 (10)	0.0994 (7)
C3	0.2965 (5)	0.7967 (4)	0.78841 (13)	0.0647 (8)
C13	0.1155 (6)	0.7849 (4)	0.74589 (16)	0.0797 (10)
C7	0.8277 (5)	0.9255 (4)	0.96363 (13)	0.0662 (8)
O2	0.8846 (4)	1.2010 (3)	1.12504 (11)	0.0890 (8)
H201	0.7775	1.1944	1.1484	0.134*
C4	0.3341 (5)	0.9302 (4)	0.82157 (14)	0.0706 (8)
H4	0.2411	1.0120	0.8158	0.085*
C10	0.8605 (5)	1.1076 (3)	1.07184 (13)	0.0647 (8)
C1	0.6082 (5)	0.6918 (4)	0.83712 (14)	0.0689 (8)
C8	0.6707 (5)	0.9204 (4)	1.01045 (14)	0.0720 (8)
H8	0.5543	0.8546	1.0059	0.086*
C6	0.6460 (5)	0.8233 (4)	0.87182 (13)	0.0648 (8)
C2	0.4369 (5)	0.6748 (4)	0.79642 (14)	0.0712 (8)
H2	0.4141	0.5839	0.7744	0.085*
C9	0.6853 (5)	1.0130 (4)	1.06440 (14)	0.0718 (9)
H9	0.5769	1.0115	1.0958	0.086*
C11	1.0188 (6)	1.1111 (4)	1.02514 (15)	0.0789 (10)
H11	1.1376	1.1745	1.0301	0.095*
C12	1.0011 (6)	1.0202 (4)	0.97087 (15)	0.0805 (10)
H12	1.1076	1.0231	0.9390	0.097*
C5	0.5080 (6)	0.9438 (4)	0.86314 (14)	0.0710 (9)
H5	0.5319	1.0344	0.8853	0.085*
N1	−0.0310 (6)	0.7800 (4)	0.71268 (15)	0.1078 (12)

	U11	U22	U33	U12	U13	U23
O1	0.0678 (14)	0.1042 (16)	0.0805 (13)	0.0258 (14)	−0.0173 (12)	−0.0286 (13)
F1	0.0986 (16)	0.0867 (12)	0.1129 (14)	0.0398 (13)	−0.0214 (12)	−0.0218 (12)
C3	0.0581 (18)	0.083 (2)	0.0534 (14)	−0.0009 (17)	−0.0006 (13)	0.0069 (16)
C13	0.076 (2)	0.092 (2)	0.0710 (19)	−0.009 (2)	−0.0057 (19)	0.0122 (18)
C7	0.0610 (18)	0.0736 (17)	0.0642 (15)	0.0089 (17)	−0.0031 (16)	−0.0066 (15)
O2	0.0893 (19)	0.0916 (15)	0.0861 (15)	−0.0181 (15)	0.0185 (13)	−0.0244 (14)
C4	0.069 (2)	0.0754 (19)	0.0671 (16)	0.0133 (18)	−0.0032 (17)	0.0033 (16)
C10	0.066 (2)	0.0648 (17)	0.0632 (15)	−0.0042 (16)	0.0052 (16)	−0.0025 (14)
C1	0.068 (2)	0.0692 (18)	0.0697 (17)	0.0159 (17)	0.0009 (16)	−0.0051 (17)
C8	0.065 (2)	0.0776 (18)	0.0733 (17)	−0.0135 (18)	0.0016 (17)	−0.0006 (17)
C6	0.0592 (19)	0.0778 (18)	0.0572 (15)	0.0090 (17)	0.0002 (14)	−0.0069 (15)
C2	0.072 (2)	0.0751 (19)	0.0665 (17)	0.0011 (18)	−0.0016 (16)	−0.0044 (17)
C9	0.068 (2)	0.084 (2)	0.0632 (16)	−0.0165 (19)	0.0125 (16)	−0.0001 (16)
C11	0.063 (2)	0.094 (2)	0.0801 (19)	−0.0177 (19)	0.0167 (18)	−0.0068 (19)
C12	0.066 (2)	0.107 (2)	0.0689 (17)	−0.004 (2)	0.0148 (18)	−0.0094 (19)
C5	0.072 (2)	0.0706 (18)	0.0706 (17)	0.0124 (17)	−0.0058 (17)	−0.0094 (17)
N1	0.094 (2)	0.128 (3)	0.101 (2)	−0.030 (2)	−0.031 (2)	0.034 (2)

O1—C6	1.365 (4)	C10—C11	1.371 (4)
O1—C7	1.403 (4)	C10—C9	1.377 (4)
F1—C1	1.350 (3)	C1—C2	1.359 (4)
C3—C4	1.379 (5)	C1—C6	1.380 (4)
C3—C2	1.391 (4)	C8—C9	1.378 (4)
C3—C13	1.425 (4)	C8—H8	0.9300
C13—N1	1.135 (4)	C6—C5	1.375 (4)
C7—C12	1.368 (5)	C2—H2	0.9300
C7—C8	1.368 (4)	C9—H9	0.9300
O2—C10	1.375 (3)	C11—C12	1.376 (4)
O2—H201	0.8200	C11—H11	0.9300
C4—C5	1.379 (4)	C12—H12	0.9300
C4—H4	0.9300	C5—H5	0.9300
C6—O1—C7	118.0 (2)	C9—C8—H8	120.0
C4—C3—C2	119.7 (3)	O1—C6—C5	124.6 (3)
C4—C3—C13	119.8 (3)	O1—C6—C1	116.9 (3)
C2—C3—C13	120.5 (3)	C5—C6—C1	118.4 (3)
N1—C13—C3	177.8 (5)	C1—C2—C3	118.4 (3)
C12—C7—C8	120.1 (3)	C1—C2—H2	120.8
C12—C7—O1	118.1 (3)	C3—C2—H2	120.8
C8—C7—O1	121.6 (3)	C10—C9—C8	119.9 (3)
C10—O2—H201	109.5	C10—C9—H9	120.0
C5—C4—C3	120.7 (3)	C8—C9—H9	120.0
C5—C4—H4	119.6	C10—C11—C12	119.7 (3)
C3—C4—H4	119.6	C10—C11—H11	120.1
C11—C10—O2	117.7 (3)	C12—C11—H11	120.1
C11—C10—C9	119.9 (3)	C7—C12—C11	120.3 (3)
O2—C10—C9	122.4 (3)	C7—C12—H12	119.8
F1—C1—C2	118.7 (3)	C11—C12—H12	119.8
F1—C1—C6	118.5 (3)	C6—C5—C4	119.9 (3)
C2—C1—C6	122.8 (3)	C6—C5—H5	120.0
C7—C8—C9	119.9 (3)	C4—C5—H5	120.0
C7—C8—H8	120.0
C6—O1—C7—C12	−129.3 (3)	C4—C3—C2—C1	0.0 (5)
C6—O1—C7—C8	56.0 (4)	C13—C3—C2—C1	179.5 (3)
C2—C3—C4—C5	−0.7 (5)	C11—C10—C9—C8	0.8 (5)
C13—C3—C4—C5	179.8 (3)	O2—C10—C9—C8	−179.2 (3)
C12—C7—C8—C9	1.2 (5)	C7—C8—C9—C10	−1.6 (5)
O1—C7—C8—C9	175.8 (3)	O2—C10—C11—C12	−179.7 (3)
C7—O1—C6—C5	27.9 (4)	C9—C10—C11—C12	0.3 (5)
C7—O1—C6—C1	−155.4 (3)	C8—C7—C12—C11	−0.1 (5)
F1—C1—C6—O1	1.0 (4)	O1—C7—C12—C11	−174.8 (3)
C2—C1—C6—O1	−179.0 (3)	C10—C11—C12—C7	−0.7 (5)
F1—C1—C6—C5	177.9 (3)	O1—C6—C5—C4	178.0 (3)
C2—C1—C6—C5	−2.1 (5)	C1—C6—C5—C4	1.4 (5)
F1—C1—C2—C3	−178.6 (3)	C3—C4—C5—C6	0.0 (5)
C6—C1—C2—C3	1.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H201···N1i	0.82	2.03	2.839 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H201⋯N1i	0.82	2.03	2.839 (4)	168

Symmetry code: (i) .