3,3'-Difluoro-4,4'-(p-phenyl-enedi-oxy)dibenzonitrile.

The title compound, C(20)H(10)F(2)N(2)O(2), was synthesized from hydro-quinone and 3,4-difluoro-benzonitrile. The centroid of the central aromatic ring is on a crystallographic center of inversion. The dihedral angle between the central and terminal rings is 77.8 (3)°. In the crystal, chains linked by C-H⋯N bond occur.

Related literature

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

Experimental

Crystal data

C20H10F2N2O2

M = 348.30

Triclinic,

a = 6.980 (1) Å

b = 7.615 (1) Å

c = 8.294 (1) Å

α = 106.376 (3)°

β = 93.698 (3)°

γ = 109.085 (3)°

V = 393.7 (1) Å3

Z = 1

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.42 × 0.37 × 0.32 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.782, T max = 1.000

2165 measured reflections

1529 independent reflections

1259 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.137

S = 1.07

1529 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809035247/im2138sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809035247/im2138Isup2.hkl

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

C20H10F2N2O2	Z = 1
Mr = 348.30	F(000) = 178
Triclinic, P1	Dx = 1.469 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.980 (1) Å	Cell parameters from 1140 reflections
b = 7.615 (1) Å	θ = 5.2–54.9°
c = 8.294 (1) Å	µ = 0.11 mm−1
α = 106.376 (3)°	T = 293 K
β = 93.698 (3)°	Prismatic, colorless
γ = 109.085 (3)°	0.42 × 0.37 × 0.32 mm
V = 393.7 (1) Å3

Bruker SMART CCD area-detector diffractometer	1529 independent reflections
Radiation source: fine-focus sealed tube	1259 reflections with I > 2σ(I)
graphite	Rint = 0.065
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.782, Tmax = 1.000	k = −9→8
2165 measured reflections	l = −10→10

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.137	w = 1/[σ2(Fo2) + (0.0836P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1529 reflections	Δρmax = 0.19 e Å−3
119 parameters	Δρmin = −0.21 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: 0.027 (6)

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	0.31400 (15)	0.41880 (17)	0.64633 (14)	0.0546 (4)
N1	0.2645 (2)	0.0341 (2)	1.2835 (2)	0.0706 (5)
F1	0.21076 (16)	0.59370 (13)	0.94706 (13)	0.0663 (4)
C1	0.2380 (2)	0.4219 (2)	0.9251 (2)	0.0463 (4)
C2	0.2823 (2)	0.3307 (2)	0.77070 (18)	0.0443 (4)
C3	0.3137 (2)	0.1573 (2)	0.7484 (2)	0.0520 (4)
H3	0.3429	0.0941	0.6448	0.062*
C4	0.3023 (2)	0.0761 (2)	0.8780 (2)	0.0524 (4)
H4	0.3229	−0.0419	0.8619	0.063*
C5	0.2601 (2)	0.1714 (2)	1.03224 (18)	0.0460 (4)
C6	0.2256 (2)	0.3453 (2)	1.05636 (19)	0.0483 (4)
H6	0.1949	0.4084	1.1592	0.058*
C7	0.2590 (2)	0.0934 (2)	1.1718 (2)	0.0535 (4)
C8	0.1518 (2)	0.4580 (2)	0.57622 (16)	0.0424 (4)
C9	−0.0514 (2)	0.3477 (2)	0.56761 (18)	0.0478 (4)
H9	−0.0856	0.2450	0.6129	0.057*
C10	0.2042 (2)	0.6087 (2)	0.50919 (18)	0.0472 (4)
H10	0.3420	0.6816	0.5152	0.057*

	U11	U22	U33	U12	U13	U23
O1	0.0475 (6)	0.0766 (8)	0.0542 (7)	0.0254 (5)	0.0116 (5)	0.0384 (6)
N1	0.0775 (11)	0.0788 (11)	0.0601 (9)	0.0206 (8)	0.0085 (8)	0.0390 (8)
F1	0.0825 (8)	0.0573 (7)	0.0671 (7)	0.0349 (5)	0.0118 (5)	0.0209 (5)
C1	0.0428 (8)	0.0463 (8)	0.0503 (9)	0.0176 (6)	0.0023 (6)	0.0158 (7)
C2	0.0385 (7)	0.0561 (9)	0.0407 (8)	0.0150 (6)	0.0028 (6)	0.0222 (7)
C3	0.0585 (9)	0.0626 (10)	0.0412 (8)	0.0290 (8)	0.0095 (7)	0.0172 (7)
C4	0.0578 (9)	0.0548 (9)	0.0510 (9)	0.0258 (7)	0.0070 (7)	0.0206 (7)
C5	0.0397 (8)	0.0560 (9)	0.0429 (8)	0.0144 (6)	0.0018 (6)	0.0211 (7)
C6	0.0451 (8)	0.0586 (9)	0.0389 (8)	0.0177 (7)	0.0049 (6)	0.0141 (7)
C7	0.0481 (9)	0.0621 (10)	0.0496 (9)	0.0149 (7)	0.0036 (7)	0.0238 (8)
C8	0.0453 (8)	0.0489 (8)	0.0338 (7)	0.0167 (6)	0.0029 (6)	0.0160 (6)
C9	0.0496 (9)	0.0461 (8)	0.0472 (9)	0.0093 (6)	0.0032 (6)	0.0247 (7)
C10	0.0401 (8)	0.0512 (9)	0.0454 (8)	0.0058 (6)	0.0033 (6)	0.0217 (7)

O1—C2	1.3731 (16)	C4—H4	0.9300
O1—C8	1.3943 (16)	C5—C6	1.385 (2)
N1—C7	1.143 (2)	C5—C7	1.442 (2)
F1—C1	1.3469 (17)	C6—H6	0.9300
C1—C6	1.368 (2)	C8—C10	1.3678 (19)
C1—C2	1.381 (2)	C8—C9	1.377 (2)
C2—C3	1.372 (2)	C9—C10i	1.385 (2)
C3—C4	1.378 (2)	C9—H9	0.9300
C3—H3	0.9300	C10—C9i	1.385 (2)
C4—C5	1.384 (2)	C10—H10	0.9300
C2—O1—C8	118.23 (11)	C6—C5—C7	119.29 (14)
F1—C1—C6	119.41 (14)	C1—C6—C5	118.30 (14)
F1—C1—C2	118.49 (13)	C1—C6—H6	120.8
C6—C1—C2	122.08 (14)	C5—C6—H6	120.8
C3—C2—O1	119.59 (13)	N1—C7—C5	177.94 (17)
C3—C2—C1	118.81 (13)	C10—C8—C9	120.96 (13)
O1—C2—C1	121.32 (13)	C10—C8—O1	116.41 (12)
C2—C3—C4	120.60 (14)	C9—C8—O1	122.58 (12)
C2—C3—H3	119.7	C8—C9—C10i	119.29 (13)
C4—C3—H3	119.7	C8—C9—H9	120.4
C3—C4—C5	119.53 (15)	C10i—C9—H9	120.4
C3—C4—H4	120.2	C8—C10—C9i	119.75 (13)
C5—C4—H4	120.2	C8—C10—H10	120.1
C4—C5—C6	120.67 (13)	C9i—C10—H10	120.1
C4—C5—C7	120.00 (15)
C8—O1—C2—C3	123.31 (15)	C2—C1—C6—C5	0.4 (2)
C8—O1—C2—C1	−62.84 (18)	C4—C5—C6—C1	−1.1 (2)
F1—C1—C2—C3	178.88 (13)	C7—C5—C6—C1	176.65 (13)
C6—C1—C2—C3	0.4 (2)	C4—C5—C7—N1	80 (5)
F1—C1—C2—O1	5.0 (2)	C6—C5—C7—N1	−98 (5)
C6—C1—C2—O1	−173.52 (13)	C2—O1—C8—C10	154.42 (13)
O1—C2—C3—C4	173.66 (13)	C2—O1—C8—C9	−28.1 (2)
C1—C2—C3—C4	−0.3 (2)	C10—C8—C9—C10i	−0.4 (2)
C2—C3—C4—C5	−0.4 (2)	O1—C8—C9—C10i	−177.78 (13)
C3—C4—C5—C6	1.2 (2)	C9—C8—C10—C9i	0.4 (2)
C3—C4—C5—C7	−176.60 (14)	O1—C8—C10—C9i	177.93 (12)
F1—C1—C6—C5	−178.13 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N1ii	0.93	2.50	3.410 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯N1i	0.93	2.50	3.410 (2)	166

Symmetry code: (i) .