5-Bromo-benzene-1,3-dicarbo-nitrile.

The asymmetric unit of the title compound, C8H3BrN2, consists of two mol-ecules. The crystal structure features undulating mol-ecular sheets with the mol-ecules linked by C-H⋯N hydrogen bonds with one N atom acting as a bifurcated acceptor. N⋯Br inter-actions also occur [N⋯Br = 2.991 (3) and 3.099 (3) Å]. Inter-layer association is accomplished by offset face-to-face arene inter-actions [centroid-centroid distance = 3.768 (4) Å].

Related literature

For use of aromatic nitrils in organic synthesis and for their industrial applications, see: Fabiani (1999 ▶); Ishii et al. (2011 ▶); Sandier & Karo (1983 ▶). For uses of aromatic nitrils in crystal engineering and the construction of metal-organic frameworks, see: Desiraju & Harlow (1989 ▶); Leonard & MacGillivray (2010 ▶); Reddy et al. (1993 ▶); Tiekink et al. (2010 ▶). For the X-ray structure of 1,3,5-tri­cyano­benzene, see: Reddy et al. (1995 ▶). For non-covalant C—H⋯N and N⋯Br inter­actions as well as arene⋯arene stacking contacts, see: Desiraju & Steiner (1999 ▶); Dance (2004 ▶); Rowland & Taylor (1996 ▶); Steiner (2002 ▶). For the preparation of the title compound, see: Doyle & Haseltine (1994 ▶).

Experimental

Crystal data

C8H3BrN2

M = 207.03

Monoclinic,

a = 13.3019 (4) Å

b = 15.7762 (5) Å

c = 7.4265 (2) Å

β = 93.719 (2)°

V = 1555.19 (8) Å3

Z = 8

Mo Kα radiation

μ = 5.21 mm−1

T = 173 K

0.45 × 0.43 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.203, T max = 0.681

16811 measured reflections

4198 independent reflections

3436 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.078

S = 1.05

4198 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-NT (Bruker, 2007 ▶); data reduction: SAINT-NT; 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, 2012 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813028857/zp2009sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028857/zp2009Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028857/zp2009Isup3.cml

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

C8H3BrN2	F(000) = 800
Mr = 207.03	Dx = 1.768 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7273 reflections
a = 13.3019 (4) Å	θ = 2.6–29.1°
b = 15.7762 (5) Å	µ = 5.21 mm−1
c = 7.4265 (2) Å	T = 173 K
β = 93.719 (2)°	Plate, colourless
V = 1555.19 (8) Å3	0.45 × 0.43 × 0.08 mm
Z = 8

Bruker APEXII CCD area-detector diffractometer	4198 independent reflections
Radiation source: fine-focus sealed tube	3436 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
phi and ω scans	θmax = 29.2°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −18→18
Tmin = 0.203, Tmax = 0.681	k = −21→21
16811 measured reflections	l = −8→10

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0289P)2 + 1.0903P] where P = (Fo2 + 2Fc2)/3
4198 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.58 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
Br1	−0.117304 (18)	0.402498 (14)	0.12147 (3)	0.03315 (8)
N1	−0.15740 (18)	0.79184 (15)	0.2893 (4)	0.0560 (7)
N2	0.27771 (15)	0.56650 (13)	0.4706 (3)	0.0366 (5)
C1	−0.05428 (17)	0.50150 (13)	0.2166 (3)	0.0265 (4)
C2	0.04561 (16)	0.49766 (13)	0.2815 (3)	0.0251 (4)
H2	0.0823	0.4461	0.2787	0.030*
C3	0.09102 (17)	0.57163 (13)	0.3513 (3)	0.0243 (4)
C4	0.03878 (16)	0.64751 (13)	0.3566 (3)	0.0266 (4)
H4	0.0703	0.6971	0.4059	0.032*
C5	−0.06113 (17)	0.64919 (14)	0.2879 (3)	0.0288 (4)
C6	−0.10855 (17)	0.57649 (14)	0.2169 (3)	0.0292 (4)
H6	−0.1766	0.5784	0.1697	0.035*
C7	−0.11580 (18)	0.72847 (15)	0.2884 (4)	0.0377 (6)
C8	0.19580 (17)	0.56869 (13)	0.4179 (3)	0.0272 (4)
Br1A	0.370700 (19)	0.099566 (15)	0.08217 (4)	0.03739 (8)
N1A	0.37898 (18)	0.49595 (14)	0.0782 (3)	0.0460 (6)
N2A	0.78226 (14)	0.24025 (12)	0.3862 (3)	0.0319 (4)
C1A	0.44634 (16)	0.19863 (13)	0.1352 (3)	0.0264 (4)
C2A	0.40402 (17)	0.27736 (14)	0.1025 (3)	0.0277 (4)
H2A	0.3364	0.2823	0.0543	0.033*
C3A	0.46205 (16)	0.34971 (13)	0.1413 (3)	0.0257 (4)
C4A	0.56122 (16)	0.34354 (13)	0.2127 (3)	0.0252 (4)
H4A	0.6006	0.3929	0.2381	0.030*
C5A	0.60110 (15)	0.26273 (13)	0.2458 (3)	0.0233 (4)
C6A	0.54470 (16)	0.18963 (12)	0.2074 (3)	0.0247 (4)
H6A	0.5729	0.1350	0.2300	0.030*
C7A	0.41674 (18)	0.43201 (15)	0.1068 (3)	0.0317 (5)
C8A	0.70312 (17)	0.25181 (12)	0.3230 (3)	0.0262 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.03797 (14)	0.02912 (13)	0.03247 (13)	−0.01325 (9)	0.00308 (10)	−0.00301 (8)
N1	0.0359 (12)	0.0372 (12)	0.095 (2)	0.0070 (10)	0.0032 (13)	0.0007 (13)
N2	0.0309 (10)	0.0297 (10)	0.0483 (13)	0.0062 (8)	−0.0035 (9)	−0.0032 (9)
C1	0.0320 (11)	0.0244 (10)	0.0234 (10)	−0.0081 (8)	0.0047 (8)	0.0003 (7)
C2	0.0310 (11)	0.0209 (9)	0.0236 (10)	−0.0016 (8)	0.0042 (8)	0.0012 (7)
C3	0.0262 (10)	0.0238 (9)	0.0229 (10)	−0.0008 (8)	0.0029 (8)	0.0012 (7)
C4	0.0270 (11)	0.0223 (10)	0.0304 (11)	−0.0021 (8)	0.0023 (9)	−0.0009 (8)
C5	0.0253 (11)	0.0262 (10)	0.0350 (12)	0.0005 (8)	0.0039 (9)	0.0013 (8)
C6	0.0226 (10)	0.0322 (11)	0.0328 (11)	−0.0035 (9)	0.0026 (9)	0.0022 (9)
C7	0.0263 (12)	0.0314 (12)	0.0554 (16)	0.0004 (10)	0.0024 (11)	0.0001 (11)
C8	0.0297 (11)	0.0200 (9)	0.0319 (11)	0.0014 (8)	0.0016 (9)	−0.0015 (8)
Br1A	0.03607 (14)	0.03308 (13)	0.04293 (15)	−0.01449 (9)	0.00186 (10)	−0.00027 (9)
N1A	0.0482 (14)	0.0387 (12)	0.0506 (14)	0.0124 (10)	−0.0004 (11)	0.0062 (10)
N2A	0.0297 (10)	0.0259 (9)	0.0394 (11)	0.0012 (8)	−0.0039 (9)	0.0011 (8)
C1A	0.0275 (11)	0.0265 (10)	0.0256 (10)	−0.0053 (8)	0.0053 (8)	−0.0007 (8)
C2A	0.0222 (10)	0.0366 (12)	0.0244 (10)	−0.0015 (9)	0.0022 (8)	0.0013 (8)
C3A	0.0280 (11)	0.0254 (10)	0.0237 (10)	0.0039 (8)	0.0018 (8)	0.0007 (8)
C4A	0.0289 (11)	0.0226 (10)	0.0240 (10)	0.0000 (8)	0.0005 (8)	−0.0009 (8)
C5A	0.0233 (10)	0.0253 (10)	0.0212 (10)	0.0006 (8)	0.0017 (8)	−0.0001 (7)
C6A	0.0268 (10)	0.0218 (9)	0.0262 (10)	−0.0004 (8)	0.0056 (8)	0.0004 (7)
C7A	0.0316 (12)	0.0330 (12)	0.0302 (11)	0.0032 (10)	0.0003 (9)	0.0018 (9)
C8A	0.0308 (11)	0.0194 (9)	0.0282 (11)	0.0002 (8)	0.0013 (9)	0.0004 (7)

Br1—C1	1.888 (2)	Br1A—C1A	1.886 (2)
N1—C7	1.143 (3)	N1A—C7A	1.141 (3)
N2—C8	1.134 (3)	N2A—C8A	1.139 (3)
C1—C2	1.385 (3)	C1A—C2A	1.379 (3)
C1—C6	1.386 (3)	C1A—C6A	1.389 (3)
C2—C3	1.398 (3)	C2A—C3A	1.397 (3)
C2—H2	0.9500	C2A—H2A	0.9500
C3—C4	1.386 (3)	C3A—C4A	1.393 (3)
C3—C8	1.449 (3)	C3A—C7A	1.447 (3)
C4—C5	1.393 (3)	C4A—C5A	1.397 (3)
C4—H4	0.9500	C4A—H4A	0.9500
C5—C6	1.396 (3)	C5A—C6A	1.395 (3)
C5—C7	1.447 (3)	C5A—C8A	1.449 (3)
C6—H6	0.9500	C6A—H6A	0.9500
C2—C1—C6	121.65 (19)	C2A—C1A—C6A	121.60 (19)
C2—C1—Br1	119.13 (16)	C2A—C1A—Br1A	120.23 (16)
C6—C1—Br1	119.21 (17)	C6A—C1A—Br1A	118.18 (15)
C1—C2—C3	118.31 (19)	C1A—C2A—C3A	119.1 (2)
C1—C2—H2	120.8	C1A—C2A—H2A	120.5
C3—C2—H2	120.8	C3A—C2A—H2A	120.5
C4—C3—C2	121.7 (2)	C4A—C3A—C2A	121.22 (19)
C4—C3—C8	119.39 (19)	C4A—C3A—C7A	120.2 (2)
C2—C3—C8	118.86 (19)	C2A—C3A—C7A	118.6 (2)
C3—C4—C5	118.3 (2)	C3A—C4A—C5A	118.05 (19)
C3—C4—H4	120.8	C3A—C4A—H4A	121.0
C5—C4—H4	120.8	C5A—C4A—H4A	121.0
C4—C5—C6	121.3 (2)	C6A—C5A—C4A	121.71 (19)
C4—C5—C7	118.9 (2)	C6A—C5A—C8A	117.39 (18)
C6—C5—C7	119.8 (2)	C4A—C5A—C8A	120.90 (18)
C1—C6—C5	118.6 (2)	C1A—C6A—C5A	118.36 (19)
C1—C6—H6	120.7	C1A—C6A—H6A	120.8
C5—C6—H6	120.7	C5A—C6A—H6A	120.8
N1—C7—C5	178.8 (3)	N1A—C7A—C3A	178.4 (3)
N2—C8—C3	179.7 (3)	N2A—C8A—C5A	177.3 (2)
C6—C1—C2—C3	1.1 (3)	C6A—C1A—C2A—C3A	0.7 (3)
Br1—C1—C2—C3	179.95 (15)	Br1A—C1A—C2A—C3A	−179.35 (16)
C1—C2—C3—C4	0.0 (3)	C1A—C2A—C3A—C4A	−0.2 (3)
C1—C2—C3—C8	−179.33 (19)	C1A—C2A—C3A—C7A	−179.9 (2)
C2—C3—C4—C5	−0.8 (3)	C2A—C3A—C4A—C5A	−0.5 (3)
C8—C3—C4—C5	178.5 (2)	C7A—C3A—C4A—C5A	179.2 (2)
C3—C4—C5—C6	0.7 (3)	C3A—C4A—C5A—C6A	0.7 (3)
C3—C4—C5—C7	−178.5 (2)	C3A—C4A—C5A—C8A	−178.87 (19)
C2—C1—C6—C5	−1.3 (3)	C2A—C1A—C6A—C5A	−0.4 (3)
Br1—C1—C6—C5	179.87 (17)	Br1A—C1A—C6A—C5A	179.62 (15)
C4—C5—C6—C1	0.4 (3)	C4A—C5A—C6A—C1A	−0.3 (3)
C7—C5—C6—C1	179.5 (2)	C8A—C5A—C6A—C1A	179.29 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C4A—H4A···N2i	0.95	2.69	3.388 (3)	130
C4—H4···N2Ai	0.95	2.61	3.444 (3)	147
C6A—H6A···N1Aii	0.95	2.67	3.563 (3)	157
C2—H2···N1iii	0.95	2.69	3.624 (3)	168
C2A—H2A···N1iii	0.95	2.72	3.435 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4A—H4A⋯N2i	0.95	2.69	3.388 (3)	130
C4—H4⋯N2A i	0.95	2.61	3.444 (3)	147
C6A—H6A⋯N1A ii	0.95	2.67	3.563 (3)	157
C2—H2⋯N1iii	0.95	2.69	3.624 (3)	168
C2A—H2A⋯N1iii	0.95	2.72	3.435 (3)	133

Symmetry codes: (i) ; (ii) ; (iii) .