1,3-Bis(chloro-meth-yl)benzene.

The title compound, C8H8Cl2, used in the synthesis of many pharmaceutical inter-mediates, forms a three-dimensional network through chlorine-chlorine inter-actions in the solid-state that measure 3.513 (1) and 3.768 (3) Å.

Related literature

For background information on the applications of halogenated xylenes, see: Ito & Tada (2009 ▶); Zordan & Brammer (2006 ▶). For related structures, see: Castaner et al. (1991 ▶). For halogen–halogen inter­actions, see: Hathwar et al. (2010 ▶). For additional information on how the space group of the structure was solved, see Spek (2009 ▶).

Experimental

Crystal data

C8H8Cl2

M = 175.04

Orthorhombic,

a = 8.5174 (5) Å

b = 12.3094 (7) Å

c = 15.2597 (9) Å

V = 1599.89 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.73 mm−1

T = 100 K

0.51 × 0.50 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2011 ▶) T min = 0.665, T max = 0.746

17126 measured reflections

1949 independent reflections

1782 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.064

S = 1.04

1949 reflections

91 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2011 ▶); cell refinement: SAINT (Bruker, 2011 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalMaker (CrystalMaker Software, 2009 ▶); software used to prepare material for publication: enCIFer (Allen et al. 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813016383/mw2106sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016383/mw2106Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016383/mw2106Isup3.cml

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

C8H8Cl2	Dx = 1.453 Mg m−3Dm = 1.453 Mg m−3Dm measured by not measured
Mr = 175.04	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 120 reflections
a = 8.5174 (5) Å	θ = 2.7–28.2°
b = 12.3094 (7) Å	µ = 0.73 mm−1
c = 15.2597 (9) Å	T = 100 K
V = 1599.89 (16) Å3	Thick plate, colourless
Z = 8	0.51 × 0.50 × 0.10 mm
F(000) = 720

Bruker APEXII CCD diffractometer	1949 independent reflections
Radiation source: fine-focus sealed tube	1782 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.3333 pixels mm-1	θmax = 28.6°, θmin = 2.7°
ω and φ scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2011)	k = −15→15
Tmin = 0.665, Tmax = 0.746	l = −20→20
17126 measured reflections

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0356P)2 + 0.6168P] where P = (Fo2 + 2Fc2)/3
1949 reflections	(Δ/σ)max = 0.001
91 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.24 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
Cl1	0.61622 (3)	0.35365 (2)	1.030229 (18)	0.02078 (9)
Cl2	0.83843 (3)	0.32450 (2)	0.660472 (18)	0.02164 (10)
C1	0.81471 (14)	0.40672 (11)	1.02366 (8)	0.0210 (3)
H1A	0.8343	0.4563	1.0736	0.025*
H1B	0.8909	0.3462	1.0272	0.025*
C2	0.83655 (13)	0.46689 (10)	0.93903 (7)	0.0159 (2)
C3	0.90389 (13)	0.41528 (9)	0.86690 (8)	0.0161 (2)
H3	0.9394	0.3424	0.8722	0.019*
C4	0.91971 (13)	0.46956 (9)	0.78693 (7)	0.0165 (2)
C5	0.98635 (14)	0.41163 (11)	0.70880 (8)	0.0218 (3)
H5A	1.0779	0.3675	0.7269	0.026*
H5B	1.0224	0.4654	0.6650	0.026*
C6	0.78830 (13)	0.57490 (10)	0.93140 (8)	0.0182 (2)
H6	0.7434	0.6110	0.9804	0.022*
C7	0.80570 (15)	0.62972 (10)	0.85252 (8)	0.0209 (2)
H7	0.7736	0.7034	0.8478	0.025*
C8	0.87016 (14)	0.57693 (10)	0.78021 (8)	0.0196 (2)
H8	0.8803	0.6144	0.7261	0.024*

	U11	U22	U33	U12	U13	U23
Cl1	0.01567 (15)	0.02646 (17)	0.02020 (16)	−0.00530 (11)	0.00008 (10)	0.00373 (11)
Cl2	0.02070 (16)	0.02609 (17)	0.01814 (15)	−0.00366 (11)	0.00164 (10)	−0.00641 (11)
C1	0.0148 (5)	0.0300 (7)	0.0181 (6)	−0.0067 (5)	−0.0028 (4)	0.0046 (5)
C2	0.0113 (5)	0.0219 (6)	0.0145 (5)	−0.0039 (4)	−0.0025 (4)	0.0009 (4)
C3	0.0121 (5)	0.0165 (5)	0.0196 (6)	−0.0015 (4)	−0.0019 (4)	0.0000 (4)
C4	0.0117 (5)	0.0216 (6)	0.0162 (5)	−0.0028 (4)	−0.0004 (4)	−0.0022 (4)
C5	0.0150 (5)	0.0298 (7)	0.0206 (6)	−0.0035 (5)	0.0013 (4)	−0.0065 (5)
C6	0.0158 (5)	0.0216 (6)	0.0173 (5)	−0.0008 (4)	0.0018 (4)	−0.0041 (4)
C7	0.0209 (6)	0.0166 (6)	0.0250 (6)	0.0013 (4)	0.0000 (5)	0.0012 (5)
C8	0.0192 (5)	0.0227 (6)	0.0171 (5)	−0.0017 (5)	0.0000 (4)	0.0039 (5)

Cl1—C1	1.8152 (12)	C4—C8	1.3912 (17)
Cl2—C5	1.8115 (12)	C4—C5	1.5007 (16)
C1—C2	1.5004 (16)	C5—H5A	0.9900
C1—H1A	0.9900	C5—H5B	0.9900
C1—H1B	0.9900	C6—C7	1.3879 (17)
C2—C3	1.3944 (16)	C6—H6	0.9500
C2—C6	1.3964 (17)	C7—C8	1.3933 (17)
C3—C4	1.3978 (16)	C7—H7	0.9500
C3—H3	0.9500	C8—H8	0.9500
C2—C1—Cl1	109.92 (8)	C4—C5—Cl2	109.97 (8)
C2—C1—H1A	109.7	C4—C5—H5A	109.7
Cl1—C1—H1A	109.7	Cl2—C5—H5A	109.7
C2—C1—H1B	109.7	C4—C5—H5B	109.7
Cl1—C1—H1B	109.7	Cl2—C5—H5B	109.7
H1A—C1—H1B	108.2	H5A—C5—H5B	108.2
C3—C2—C6	119.28 (11)	C7—C6—C2	120.25 (11)
C3—C2—C1	120.37 (11)	C7—C6—H6	119.9
C6—C2—C1	120.35 (11)	C2—C6—H6	119.9
C2—C3—C4	120.73 (11)	C6—C7—C8	120.14 (11)
C2—C3—H3	119.6	C6—C7—H7	119.9
C4—C3—H3	119.6	C8—C7—H7	119.9
C8—C4—C3	119.29 (11)	C4—C8—C7	120.28 (11)
C8—C4—C5	120.50 (11)	C4—C8—H8	119.9
C3—C4—C5	120.19 (11)	C7—C8—H8	119.9