3-Bromo­pyridine-2-carbo­nitrile

The title compound, C₆H₃BrN₂, also known as 3-bromo­picolino­nitrile, was synthesized by cyanation of 2,3-di­bromo­pyridine. In the solid state, short inter­molecular Br...N contacts are observed. Additionally, the crystal packing is consolidated by π–π stacking inter­actions with centroid–centroid distances of 3.7893 (9) Å.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.016
• wR factor = 0.042
• Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    Br1      --C2       .        8.2 s.u.

Alert level G
PLAT431_ALERT_2_G Short Inter HL..A Contact  Br1      ..N2       .       3.12 Ang.
                                            1-x,1/2+y,1/2-z  =      2_655 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).

3-Bromopyridine-2-carbonitrile

Crystal data

C6H3BrN2	F(000) = 352
Mr = 183.01	Dx = 1.936 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.8821 (2) Å	Cell parameters from 9981 reflections
b = 11.7480 (3) Å	θ = 2.8–28.8°
c = 7.4169 (2) Å	µ = 6.44 mm^−1
β = 113.906 (1)°	T = 150 K
V = 627.88 (3) Å^3	Part of a needle, colourless
Z = 4	0.43 × 0.39 × 0.22 mm

Data collection

Bruker Kappa APEXII DUO diffractometer	1637 independent reflections
Radiation source: fine-focus sealed tube	1577 reflections with I > 2σ(I)
Curved graphite monochromator	Rint = 0.020
Detector resolution: 8.3333 pixels mm^-1	θmax = 28.8°, θmin = 3.3°
ω and phi scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −15→15
Tmin = 0.17, Tmax = 0.34	l = −10→8
18621 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.016	H-atom parameters constrained
wR(F^2) = 0.042	w = 1/[σ^2(Fo^2) + (0.0198P)^2 + 0.3045P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.001
1637 reflections	Δρmax = 0.38 e Å^−3
82 parameters	Δρmin = −0.37 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The H atoms were refined as riding, with C–H = 0.95 Å and U_iso(H) = -1.2U_eq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.30145 (2)	0.36783 (2)	0.19853 (2)	0.02306 (6)
C1	0.0879 (2)	0.16246 (12)	0.1697 (2)	0.0229 (3)
C2	0.08389 (19)	0.28060 (12)	0.1631 (2)	0.0219 (3)
C3	−0.0811 (2)	0.33623 (13)	0.1323 (2)	0.0272 (3)
H3	−0.0885	0.4170	0.1274	0.033*
C4	−0.2344 (2)	0.27070 (14)	0.1088 (2)	0.0286 (3)
H4	−0.3499	0.3058	0.0860	0.034*
C5	−0.2173 (2)	0.15295 (14)	0.1192 (3)	0.0287 (3)
H5	−0.3235	0.1090	0.1037	0.034*
C6	0.2574 (2)	0.10001 (14)	0.2049 (2)	0.0274 (3)
N1	−0.05951 (18)	0.09830 (12)	0.1497 (2)	0.0280 (3)
N2	0.3907 (2)	0.05012 (14)	0.2363 (2)	0.0384 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02029 (8)	0.02140 (8)	0.02829 (9)	−0.00458 (5)	0.01069 (6)	−0.00295 (5)
C1	0.0233 (6)	0.0217 (6)	0.0235 (7)	0.0023 (5)	0.0094 (5)	0.0002 (5)
C2	0.0219 (6)	0.0213 (6)	0.0222 (6)	−0.0009 (5)	0.0087 (5)	−0.0011 (5)
C3	0.0277 (7)	0.0211 (6)	0.0314 (8)	0.0040 (5)	0.0104 (6)	0.0003 (6)
C4	0.0226 (6)	0.0301 (8)	0.0330 (8)	0.0053 (6)	0.0110 (6)	0.0015 (6)
C5	0.0231 (7)	0.0278 (7)	0.0354 (8)	0.0006 (6)	0.0121 (6)	0.0022 (6)
C6	0.0273 (7)	0.0238 (7)	0.0320 (8)	0.0017 (6)	0.0129 (6)	−0.0017 (6)
N1	0.0255 (6)	0.0233 (6)	0.0362 (7)	0.0013 (5)	0.0136 (5)	0.0023 (5)
N2	0.0311 (7)	0.0354 (8)	0.0485 (9)	0.0077 (6)	0.0161 (7)	−0.0040 (7)

Geometric parameters (Å, º)

Br1—C2	1.9220 (14)	C3—H3	0.9500
C1—N1	1.3418 (19)	C4—C5	1.389 (2)
C1—C2	1.389 (2)	C4—H4	0.9500
C1—C6	1.452 (2)	C5—N1	1.335 (2)
C2—C3	1.390 (2)	C5—H5	0.9500
C3—C4	1.382 (2)	C6—N2	1.141 (2)
N1—C1—C2	123.46 (14)	C3—C4—C5	119.18 (14)
N1—C1—C6	115.37 (13)	C3—C4—H4	120.4
C2—C1—C6	121.15 (14)	C5—C4—H4	120.4
C1—C2—C3	118.83 (13)	N1—C5—C4	123.44 (15)
C1—C2—Br1	121.45 (11)	N1—C5—H5	118.3
C3—C2—Br1	119.71 (11)	C4—C5—H5	118.3
C4—C3—C2	118.08 (14)	N2—C6—C1	178.55 (19)
C4—C3—H3	121.0	C5—N1—C1	117.00 (14)
C2—C3—H3	121.0
N1—C1—C2—C3	−0.6 (2)	C2—C3—C4—C5	0.7 (2)
C6—C1—C2—C3	−178.91 (14)	C3—C4—C5—N1	−0.4 (3)
N1—C1—C2—Br1	178.61 (11)	C4—C5—N1—C1	−0.5 (2)
C6—C1—C2—Br1	0.3 (2)	C2—C1—N1—C5	1.0 (2)
C1—C2—C3—C4	−0.3 (2)	C6—C1—N1—C5	179.35 (14)
Br1—C2—C3—C4	−179.52 (12)