1,3-Difluoro-benzene.

The weak electrostatic and dispersive forces between C(δ+)-F(δ-) and H(δ+)-C(δ-) are at the borderline of the hydrogen-bond phenomenon and are poorly directional and further deformed in the presence of other dominant inter-actions, e.g. C-H⋯π. The title compound, C(6)H(4)F(2), Z' = 2, forms one-dimensional tapes along two homodromic C-H⋯F hydrogen bonds. The one-dimensional tapes are connected into corrugated two-dimensional sheets by further bi- or trifrucated C-H⋯F hydrogen bonds. Packing in the third dimension is controlled by C-H⋯π inter-actions.

Related literature

For C—H⋯F inter­actions, see: Althoff et al. (2006 ▶); Bats et al. (2000 ▶); Choudhury et al. (2004 ▶); D’Oria & Novoa (2008 ▶); Dunitz & Taylor (1997 ▶); Howard et al. (1996 ▶); Müller et al. (2007 ▶); O’Hagan (2008 ▶); Reichenbacher et al. (2005 ▶); Weiss et al. (1997 ▶). For the crystal structures of polyfluorinated benzenes, see: Thalladi et al. (1998 ▶). For crystallization techniques, see: Boese & Nussbaumer (1994 ▶).

Experimental

Crystal data

C6H4F2

M = 114.09

Monoclinic,

a = 24.6618 (13) Å

b = 12.2849 (5) Å

c = 7.2336 (4) Å

β = 106.842 (3)°

V = 2097.55 (18) Å3

Z = 16

Mo Kα radiation

μ = 0.13 mm−1

T = 153 K

0.30 × 0.30 × 0.30 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.876, T max = 0.961

7831 measured reflections

2099 independent reflections

1578 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.100

S = 1.01

2099 reflections

146 parameters

H-atom parameters not refined

Δρmax = 0.19 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2008 ▶) and GIMP (The GIMP team, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, glonal. DOI: 10.1107/S1600536809038987/ci2886sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038987/ci2886Isup2.hkl

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

C6H4F2	F(000) = 928
Mr = 114.09	Dx = 1.445 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2977 reflections
a = 24.6618 (13) Å	θ = 2.9–28.2°
b = 12.2849 (5) Å	µ = 0.13 mm−1
c = 7.2336 (4) Å	T = 153 K
β = 106.842 (3)°	Cylindric, colourless
V = 2097.55 (18) Å3	0.30 × 0.30 × 0.30 mm
Z = 16

Bruker SMART APEXII area-detector diffractometer	2099 independent reflections
Radiation source: fine-focus sealed tube	1578 reflections with I > 2σ(I)
graphite	Rint = 0.020
Detector resolution: 512 pixels mm-1	θmax = 28.3°, θmin = 1.9°
Data collection strategy APEX 2/COSMO with chi +/– 10° scans	h = −27→29
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −16→16
Tmin = 0.876, Tmax = 0.961	l = −9→8
7831 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)] = 0.032	H-atom parameters not refined
wR(F2) = 0.100	w = 1/[s2(Fo2) + (0.0494P)2 + 0.6228P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2099 reflections	Δρmax = 0.19 e Å−3
146 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXTL (Bruker, 2008), Fc*=kFc[1+0.001xFc2λ3sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0034 (7)

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
F1	0.20034 (3)	0.21738 (6)	0.63089 (12)	0.0520 (3)
F2	0.01617 (3)	0.35397 (7)	0.49907 (14)	0.0587 (3)
C1	0.16251 (5)	0.29864 (9)	0.56491 (16)	0.0349 (3)
C2	0.10797 (6)	0.28273 (9)	0.56876 (17)	0.0372 (3)
H2	0.0966	0.2170	0.6188	0.045*
C3	0.07043 (6)	0.36645 (10)	0.49742 (18)	0.0370 (3)
C4	0.08585 (6)	0.46202 (9)	0.42616 (17)	0.0378 (3)
H4	0.0586	0.5187	0.3775	0.045*
C5	0.14156 (6)	0.47408 (9)	0.42727 (16)	0.0370 (3)
H5	0.1531	0.5394	0.3793	0.044*
C6	0.18102 (6)	0.39238 (9)	0.49720 (17)	0.0355 (3)
H6	0.2199	0.4008	0.4989	0.043*
F11	0.23615 (3)	0.09707 (6)	0.01979 (13)	0.0571 (3)
F12	0.05258 (4)	−0.03682 (6)	−0.08892 (13)	0.0625 (3)
C11	0.18189 (6)	0.11273 (10)	0.01807 (17)	0.0365 (3)
C12	0.14440 (6)	0.02770 (9)	−0.03976 (17)	0.0382 (3)
H12	0.1558	−0.0409	−0.0800	0.046*
C13	0.08994 (6)	0.04613 (9)	−0.03803 (18)	0.0385 (3)
C14	0.07131 (6)	0.14411 (9)	0.01511 (18)	0.0380 (3)
H14	0.0325	0.1545	0.0122	0.046*
C15	0.11075 (6)	0.22716 (9)	0.07194 (17)	0.0383 (3)
H15	0.0992	0.2961	0.1105	0.046*
C16	0.16634 (6)	0.21260 (9)	0.07456 (18)	0.0392 (3)
H16	0.1934	0.2705	0.1133	0.047*

	U11	U22	U33	U12	U13	U23
F1	0.0441 (6)	0.0416 (4)	0.0679 (5)	0.0105 (3)	0.0124 (4)	0.0059 (3)
F2	0.0295 (6)	0.0668 (5)	0.0841 (6)	−0.0076 (4)	0.0234 (5)	−0.0023 (4)
C1	0.0343 (9)	0.0338 (5)	0.0352 (6)	0.0013 (5)	0.0078 (6)	−0.0017 (4)
C2	0.0397 (9)	0.0341 (6)	0.0401 (6)	−0.0071 (5)	0.0153 (6)	−0.0012 (4)
C3	0.0257 (9)	0.0455 (6)	0.0411 (6)	−0.0062 (5)	0.0118 (6)	−0.0064 (5)
C4	0.0346 (9)	0.0382 (6)	0.0379 (6)	0.0027 (5)	0.0064 (6)	0.0002 (5)
C5	0.0405 (9)	0.0351 (6)	0.0362 (6)	−0.0046 (5)	0.0123 (6)	0.0017 (4)
C6	0.0267 (9)	0.0421 (6)	0.0395 (6)	−0.0053 (5)	0.0122 (6)	−0.0038 (5)
F11	0.0289 (6)	0.0654 (5)	0.0794 (6)	0.0116 (4)	0.0195 (5)	0.0076 (4)
F12	0.0502 (6)	0.0499 (5)	0.0894 (6)	−0.0173 (4)	0.0235 (5)	−0.0145 (4)
C11	0.0242 (9)	0.0468 (6)	0.0392 (6)	0.0077 (5)	0.0100 (6)	0.0073 (5)
C12	0.0425 (9)	0.0346 (6)	0.0402 (6)	0.0064 (5)	0.0161 (6)	0.0016 (5)
C13	0.0370 (9)	0.0375 (6)	0.0416 (6)	−0.0045 (5)	0.0122 (6)	−0.0014 (5)
C14	0.0283 (9)	0.0452 (6)	0.0433 (7)	0.0049 (5)	0.0149 (6)	0.0019 (5)
C15	0.0403 (9)	0.0357 (6)	0.0409 (6)	0.0049 (5)	0.0150 (6)	−0.0018 (4)
C16	0.0355 (9)	0.0381 (6)	0.0423 (7)	−0.0041 (5)	0.0086 (6)	−0.0017 (5)

F1—C1	1.3553 (13)	F11—C11	1.3486 (14)
F2—C3	1.3506 (15)	F12—C13	1.3515 (14)
C1—C2	1.3673 (18)	C11—C12	1.3773 (17)
C1—C6	1.3797 (15)	C11—C16	1.3820 (16)
C2—C3	1.3800 (17)	C12—C13	1.3656 (18)
C2—H2	0.96	C12—H12	0.96
C3—C4	1.3793 (16)	C13—C14	1.3821 (16)
C4—C5	1.3794 (18)	C14—C15	1.3872 (17)
C4—H4	0.96	C14—H14	0.96
C5—C6	1.3874 (17)	C15—C16	1.3772 (18)
C5—H5	0.95	C15—H15	0.96
C6—H6	0.96	C16—H16	0.96
F1—C1—C2	117.92 (10)	F11—C11—C12	118.14 (11)
F1—C1—C6	118.36 (11)	F11—C11—C16	118.92 (11)
C2—C1—C6	123.71 (11)	C12—C11—C16	122.94 (12)
C1—C2—C3	116.30 (10)	C13—C12—C11	116.54 (11)
C1—C2—H2	121.7	C13—C12—H12	121.6
C3—C2—H2	122.0	C11—C12—H12	121.8
F2—C3—C2	118.12 (10)	F12—C13—C12	117.85 (10)
F2—C3—C4	118.76 (12)	F12—C13—C14	118.50 (11)
C2—C3—C4	123.12 (12)	C12—C13—C14	123.65 (11)
C3—C4—C5	118.11 (11)	C13—C14—C15	117.50 (12)
C3—C4—H4	121.0	C13—C14—H14	121.3
C5—C4—H4	120.9	C15—C14—H14	121.2
C4—C5—C6	121.10 (11)	C16—C15—C14	121.22 (11)
C4—C5—H5	119.5	C16—C15—H15	119.3
C6—C5—H5	119.4	C14—C15—H15	119.5
C1—C6—C5	117.64 (12)	C15—C16—C11	118.14 (11)
C1—C6—H6	121.2	C15—C16—H16	120.8
C5—C6—H6	121.2	C11—C16—H16	121.0

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F12i	0.96	2.72	3.3750 (14)	126
C4—H4···F2ii	0.96	2.76	3.5386 (16)	139
C5—H5···F11iii	0.95	2.71	3.2948 (16)	121
C6—H6···F11iii	0.96	2.66	3.2644 (15)	121
C6—H6···F1iv	0.96	2.82	3.5789 (17)	137
C12—H12···F1v	0.96	2.70	3.3919 (14)	130
C14—H14···F2vi	0.96	2.72	3.3442 (16)	123
C14—H14···F12vii	0.96	2.73	3.5075 (18)	138
C15—H15···F2vi	0.96	2.81	3.3995 (17)	120
C16—H16···F11viii	0.96	2.75	3.5591 (16)	142
C2—H2···Cg2ix	0.96	2.96	3.6653 (13)	131
C12—H12···Cg2v	0.96	2.99	3.6547 (13)	127
C5—H5···Cg1x	0.95	2.83	3.5153 (12)	130
C15—H15···Cg1	0.96	2.87	3.5283 (13)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯F12i	0.96	2.72	3.3750 (14)	126
C4—H4⋯F2ii	0.96	2.76	3.5386 (16)	139
C5—H5⋯F11iii	0.95	2.71	3.2948 (16)	121
C6—H6⋯F11iii	0.96	2.66	3.2644 (15)	121
C6—H6⋯F1iv	0.96	2.82	3.5789 (17)	137
C12—H12⋯F1v	0.96	2.70	3.3919 (14)	130
C14—H14⋯F2vi	0.96	2.72	3.3442 (16)	123
C14—H14⋯F12vii	0.96	2.73	3.5075 (18)	138
C15—H15⋯F2vi	0.96	2.81	3.3995 (17)	120
C16—H16⋯F11viii	0.96	2.75	3.5591 (16)	142
C2—H2⋯Cg2ix	0.96	2.96	3.6653 (13)	131
C12—H12⋯Cg2v	0.96	2.99	3.6547 (13)	127
C5—H5⋯Cg1x	0.95	2.83	3.5153 (12)	130
C15—H15⋯Cg1	0.96	2.87	3.5283 (13)	127

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) . Cg1 and Cg2 are the centroids of the C1–C6 and C11–C16 rings, respectively.