6-Bromo­quinoline-8-carbo­nitrile

In the title compound, C₁₀H₅BrN₂, the whole mol­ecule is essentially planar (r.m.s. deviation = 0.005 Å). The crystal packing features face-to-face π–π stacking inter­actions [centroid–centroid distance = 3.755 (3) Å] between the pyridine and benzene rings of the quinoline ring systems of adjacent mol­ecules, along the a-axis direction. Short Br...Br contacts of 3.5908 (12) Å (compared to a van der Waals separation of 3.70 Å) are also observed.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.058
• wR factor = 0.120
• Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0076 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     11.528 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.302 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br1    ..  Br1     ..       3.59 Ang.
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          5 Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   1 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, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP3for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

6-Bromoquinoline-8-carbonitrile

Crystal data

C10H5BrN2	F(000) = 456
Mr = 233.07	Dx = 1.767 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 3.8484 (8) Å	Cell parameters from 9362 reflections
b = 12.634 (3) Å	θ = 3.2–25.3°
c = 18.042 (4) Å	µ = 4.64 mm^−1
β = 92.918 (7)°	T = 296 K
V = 876.0 (3) Å^3	Prism, colourless
Z = 4	0.15 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	1501 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.073
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	θmax = 28.5°, θmin = 3.2°
Tmin = 0.565, Tmax = 0.746	h = −4→5
26227 measured reflections	k = −16→16
2203 independent reflections	l = −24→24

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.120	w = 1/[σ^2(Fo^2) + (0.0088P)^2 + 3.5104P] where P = (Fo^2 + 2Fc^2)/3
S = 1.22	(Δ/σ)max < 0.001
2203 reflections	Δρmax = 0.53 e Å^−3
118 parameters	Δρmin = −0.61 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.

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

	x	y	z	Uiso*/Ueq
C1	0.0305 (16)	0.4253 (5)	0.8151 (3)	0.0491 (15)
H1	−0.0601	0.4759	0.8462	0.059*
C2	0.1004 (16)	0.3254 (5)	0.8451 (3)	0.0482 (15)
H2	0.0526	0.3104	0.8940	0.058*
C3	0.2403 (15)	0.2500 (5)	0.8014 (3)	0.0449 (14)
H3	0.2927	0.1832	0.8206	0.054*
C4	0.3047 (14)	0.2741 (4)	0.7272 (3)	0.0346 (11)
C5	0.4372 (14)	0.1998 (4)	0.6781 (3)	0.0375 (12)
H5	0.4966	0.1322	0.6948	0.045*
C6	0.4792 (14)	0.2268 (4)	0.6057 (3)	0.0339 (11)
C7	0.3995 (14)	0.3287 (4)	0.5793 (3)	0.0371 (12)
H7	0.4317	0.3460	0.5300	0.045*
C8	0.2738 (14)	0.4027 (4)	0.6266 (3)	0.0337 (11)
C9	0.2174 (13)	0.3781 (4)	0.7021 (2)	0.0332 (10)
C10	0.1862 (16)	0.5105 (5)	0.5988 (3)	0.0438 (14)
N1	0.0822 (12)	0.4542 (4)	0.7461 (2)	0.0412 (11)
N2	0.1305 (16)	0.5879 (4)	0.5762 (3)	0.0606 (15)
Br1	0.63809 (18)	0.12498 (5)	0.53862 (3)	0.0525 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.052 (4)	0.058 (4)	0.038 (3)	−0.006 (3)	0.006 (3)	−0.015 (3)
C2	0.049 (4)	0.068 (4)	0.028 (3)	−0.008 (3)	0.006 (2)	−0.003 (3)
C3	0.049 (4)	0.050 (3)	0.035 (3)	−0.003 (3)	0.002 (2)	0.008 (2)
C4	0.035 (3)	0.036 (3)	0.031 (2)	−0.005 (2)	−0.004 (2)	0.000 (2)
C5	0.039 (3)	0.033 (3)	0.040 (3)	−0.002 (2)	0.001 (2)	0.002 (2)
C6	0.033 (3)	0.033 (3)	0.035 (2)	−0.002 (2)	0.001 (2)	−0.003 (2)
C7	0.037 (3)	0.043 (3)	0.031 (2)	−0.001 (2)	0.003 (2)	0.001 (2)
C8	0.037 (3)	0.030 (3)	0.034 (2)	−0.004 (2)	−0.004 (2)	0.0005 (19)
C9	0.036 (3)	0.033 (2)	0.031 (2)	−0.003 (2)	0.0006 (19)	−0.002 (2)
C10	0.056 (4)	0.047 (3)	0.029 (2)	0.002 (3)	0.007 (2)	−0.001 (2)
N1	0.043 (3)	0.043 (3)	0.038 (2)	−0.004 (2)	0.004 (2)	−0.0097 (19)
N2	0.085 (5)	0.047 (3)	0.051 (3)	0.010 (3)	0.011 (3)	−0.001 (2)
Br1	0.0572 (4)	0.0517 (4)	0.0490 (3)	0.0076 (3)	0.0052 (2)	−0.0145 (3)

Geometric parameters (Å, º)

C1—N1	1.321 (7)	C5—H5	0.9300
C1—C2	1.394 (8)	C6—C7	1.401 (7)
C1—H1	0.9300	C6—Br1	1.889 (5)
C2—C3	1.364 (8)	C7—C8	1.371 (7)
C2—H2	0.9300	C7—H7	0.9300
C3—C4	1.408 (7)	C8—C9	1.425 (6)
C3—H3	0.9300	C8—C10	1.484 (7)
C4—C5	1.404 (7)	C9—N1	1.366 (6)
C4—C9	1.425 (7)	C10—N2	1.077 (7)
C5—C6	1.368 (7)
N1—C1—C2	125.5 (5)	C5—C6—C7	121.3 (5)
N1—C1—H1	117.3	C5—C6—Br1	120.0 (4)
C2—C1—H1	117.3	C7—C6—Br1	118.7 (4)
C3—C2—C1	118.8 (5)	C8—C7—C6	119.5 (4)
C3—C2—H2	120.6	C8—C7—H7	120.2
C1—C2—H2	120.6	C6—C7—H7	120.2
C2—C3—C4	119.5 (5)	C7—C8—C9	121.5 (4)
C2—C3—H3	120.3	C7—C8—C10	119.8 (4)
C4—C3—H3	120.3	C9—C8—C10	118.7 (4)
C5—C4—C3	122.9 (5)	N1—C9—C8	118.9 (4)
C5—C4—C9	120.2 (4)	N1—C9—C4	123.7 (4)
C3—C4—C9	116.8 (5)	C8—C9—C4	117.4 (4)
C6—C5—C4	120.0 (5)	N2—C10—C8	177.0 (6)
C6—C5—H5	120.0	C1—N1—C9	115.7 (5)
C4—C5—H5	120.0
N1—C1—C2—C3	1.4 (10)	C7—C8—C9—N1	−178.1 (5)
C1—C2—C3—C4	−1.1 (9)	C10—C8—C9—N1	0.5 (7)
C2—C3—C4—C5	−177.9 (5)	C7—C8—C9—C4	1.5 (8)
C2—C3—C4—C9	0.0 (8)	C10—C8—C9—C4	−179.9 (5)
C3—C4—C5—C6	177.0 (5)	C5—C4—C9—N1	178.9 (5)
C9—C4—C5—C6	−0.8 (8)	C3—C4—C9—N1	1.0 (8)
C4—C5—C6—C7	1.5 (8)	C5—C4—C9—C8	−0.6 (7)
C4—C5—C6—Br1	−177.2 (4)	C3—C4—C9—C8	−178.6 (5)
C5—C6—C7—C8	−0.6 (8)	C2—C1—N1—C9	−0.4 (9)
Br1—C6—C7—C8	178.0 (4)	C8—C9—N1—C1	178.8 (5)
C6—C7—C8—C9	−0.9 (8)	C4—C9—N1—C1	−0.8 (8)
C6—C7—C8—C10	−179.5 (5)