5-Bromo­benzene-1,3-dicarbo­nitrile

Seidel, N.; Seichter, W.; Weber, E.

doi:10.1107/S1600536813028857

organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1732-o1733

doi:10.1107/S1600536813028857

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5-Bromobenzene-1,3-dicarbonitrile

Nadine Seidel,^a Wilhelm Seichter ^a and Edwin Weber ^a ^*

^aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
^*Correspondence e-mail: edwin.weber@chemie-tu.freiberg.de

(Received 25 September 2013; accepted 21 October 2013; online 6 November 2013)

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

CCDC reference: 967566

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_r = 207.03
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.078
S = 1.05
4198 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.58 e Å⁻³

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⋯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
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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).

Supporting information

CCDC reference: 967566

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813028857/zp2009sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813028857/zp2009Isup3.cml

checkCIF report

Comment top

Aromatic nitriles are important intermediate compounds in organic synthesis (Ishii et al., 2011). They can smoothly be converted into a great many of other functional groups, such as carboxylic acids, amidines, amines, esters and ketones (Sandier et al., 1983). Futhermore, they are used as functional materials, pharmaceuticals, dyes and liquid crystals (Fabiani et al., 1999). Recently, aromatic nitriles have also arisen interest for their capability of forming supramolecular interactions that turned out to good account in organic crystal engineering (Desiraju & Harlow, 1989; Reddy et al., 1993; Tiekink et al., 2010) or the construction of metal-organic framework structures (Leonard & MacGillivray, 2010). Relating to this latter topics, the title compound has been synthesized as a precursor and was identified by single-crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P2₁/c with two molecules in the asymmetric part of the unit cell (Fig. 1). The bond distances and angles within the aromatic rings agree well with those found in the crystal structure of 1,3,5-tricyanobenzene (Reddy et al., 1995). According to a tilt angle of 12.3 (1) ° between the independent molecules, the crystal structure is composed of undulated molecular layers with the molecules linked by C—H···N hydrogen bonds (Desiraju & Steiner, 1999) [d(H)···N) 2.61 - 2.72 Å; C—H···N 114 - 168 °]. In this coordination structure (Figs. 2 and 3), the nitrogen N1 acts as a bifurcated acceptor (Steiner, 2002). Moreover, the interatomic distances between N2 and the bromo substituents of neighbouring molecules [2.991 (2) and 3.099 (2) Å], being considerably shorter than the sum of van der Waals radii of the respective atoms (3.40 Å), indicate the presence of N···Br interactions (Rowland & Taylor, 1996). In direction of the stacking axis of the molecular sheets, the crystal is stabilized by offset face-to-face arene interactions [Cg_A···Cg_A = 3.768 (4) Å] (Dance, 2004).

Related literature top

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 top

The title compound was synthesized from 5-bromo-1,3-benzenedicarboxylic acid following the literature procedure (Doyle & Haseltine, 1994). Single crystals of X-ray diffraction quality were obtained as colourless plates via crystallization from acetone.

Computing details top

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

Figures top

	Fig. 1. Asymmetric unit of the title compound, showing the atom numbering scheme. Displacement ellipsoids for the non-H atoms are drawn at the 50% probability level.
	Fig. 2. Packing structure viewed along the c-axis. Relevant intermolecular interactions are indicated as broken lines.
	Fig. 3. A view along the b-axis showing the intermolecular contacts as broken lines.

5-Bromobenzene-1,3-dicarbonitrile top

Crystal data top

C₈H₃BrN₂	F(000) = 800
M_r = 207.03	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0289P)² + 1.0903P] where P = (F_o² + 2F_c²)/3
4198 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₈H₃BrN₂	V = 1555.19 (8) Å³
M_r = 207.03	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.3019 (4) Å	µ = 5.21 mm⁻¹
b = 15.7762 (5) Å	T = 173 K
c = 7.4265 (2) Å	0.45 × 0.43 × 0.08 mm
β = 93.719 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4198 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3436 reflections with I > 2σ(I)
T_min = 0.203, T_max = 0.681	R_int = 0.039
16811 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.078	H-atom parameters constrained
S = 1.05	Δρ_max = 0.60 e Å⁻³
4198 reflections	Δρ_min = −0.58 e Å⁻³
199 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2.

Acknowledgements

This work was performed within the Cluster of Excellence "Structure Design of Novel High-Performance Materials via Atomic Design and Defect Engineering (ADDE)" which is supported financially by the European Union (European Regional Development Fund) and by the Ministry of Science and Art of Saxony (SMWK).

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