2-Bromo-pyridine-3-carboxylic acid.

The carboxylic acid residue in the title compound, C(6)H(4)BrNO(2), is twisted out of the plane of the other atoms, as indicated by the (Br)C-C-C-O(carbon-yl) torsion angle of -20.1 (9)°. In the crystal, supra-molecular chains mediated by O-H⋯N hydrogen bonds are formed with base vector [201] and C-H⋯O inter-actions reinforce the packing.

Related literature

For the biological activity of N-heterocylic compounds, see: de Souza (2005 ▶); Cunico et al. (2006 ▶). For related structures, see: Wright & King (1953 ▶); Kutoglu & Scheringer (1983 ▶); de Souza et al. (2005 ▶); Kaiser et al. (2009 ▶). For the synthesis, see: Bradlow & van der Werf (1949 ▶).

Experimental

Crystal data

C6H4BrNO2

M = 202.01

Monoclinic,

a = 3.9286 (3) Å

b = 12.9737 (9) Å

c = 12.8570 (8) Å

β = 96.695 (4)°

V = 650.83 (8) Å3

Z = 4

Mo Kα radiation

μ = 6.24 mm−1

T = 120 K

0.10 × 0.09 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.453, T max = 0.607

7699 measured reflections

1147 independent reflections

882 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.093

S = 1.06

1147 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.86 e Å−3

Δρmin = −0.62 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DEn class="Chemical">NZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003314/hb5318sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003314/hb5318Isup2.hkl

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

C6H4BrNO2	F(000) = 392
Mr = 202.01	Dx = 2.062 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 24006 reflections
a = 3.9286 (3) Å	θ = 2.9–27.5°
b = 12.9737 (9) Å	µ = 6.24 mm−1
c = 12.8570 (8) Å	T = 120 K
β = 96.695 (4)°	Block, colourless
V = 650.83 (8) Å3	0.10 × 0.09 × 0.08 mm
Z = 4

Nonius KappaCCD area-detector diffractometer	1147 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	882 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.070
Detector resolution: 9.091 pixels mm-1	θmax = 25.0°, θmin = 3.2°
φ and ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −15→15
Tmin = 0.453, Tmax = 0.607	l = −15→13
7699 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0439P)2 + 1.1585P] where P = (Fo2 + 2Fc2)/3
1147 reflections	(Δ/σ)max = 0.001
92 parameters	Δρmax = 0.86 e Å−3
0 restraints	Δρmin = −0.62 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Br	0.26644 (13)	0.59770 (4)	0.89357 (4)	0.0284 (2)
O1	−0.1485 (10)	0.8088 (3)	0.6204 (3)	0.0329 (9)
H1	−0.2563	0.7783	0.5691	0.049*
O2	0.0225 (11)	0.6488 (3)	0.6647 (3)	0.0484 (12)
N1	0.5499 (10)	0.7843 (3)	0.9471 (3)	0.0257 (10)
C2	0.3563 (13)	0.7384 (4)	0.8676 (4)	0.0237 (11)
C3	0.2287 (12)	0.7899 (4)	0.7756 (4)	0.0246 (11)
C4	0.3069 (14)	0.8942 (4)	0.7698 (4)	0.0303 (12)
H4	0.2193	0.9327	0.7098	0.036*
C5	0.5111 (13)	0.9428 (4)	0.8507 (4)	0.0252 (12)
H5	0.5688	1.0137	0.8461	0.030*
C6	0.6276 (13)	0.8854 (4)	0.9378 (4)	0.0268 (12)
H6	0.7679	0.9179	0.9935	0.032*
C7	0.0240 (13)	0.7406 (4)	0.6822 (4)	0.0290 (12)

	U11	U22	U33	U12	U13	U23
Br	0.0342 (3)	0.0217 (3)	0.0277 (3)	−0.0033 (2)	−0.0029 (2)	0.0016 (2)
O1	0.042 (2)	0.030 (2)	0.025 (2)	0.0023 (18)	−0.0059 (17)	−0.0007 (16)
O2	0.072 (3)	0.027 (2)	0.041 (2)	0.009 (2)	−0.018 (2)	−0.0066 (19)
N1	0.031 (2)	0.024 (2)	0.023 (2)	0.0023 (19)	0.0034 (19)	−0.0008 (19)
C2	0.021 (2)	0.024 (3)	0.026 (3)	0.002 (2)	0.005 (2)	−0.001 (2)
C3	0.023 (3)	0.026 (3)	0.024 (3)	0.005 (2)	0.002 (2)	−0.003 (2)
C4	0.035 (3)	0.025 (3)	0.029 (3)	0.003 (2)	−0.003 (2)	0.003 (2)
C5	0.030 (3)	0.020 (3)	0.026 (3)	−0.001 (2)	0.003 (2)	−0.003 (2)
C6	0.027 (3)	0.028 (3)	0.024 (3)	0.000 (2)	−0.002 (2)	−0.007 (2)
C7	0.028 (3)	0.031 (3)	0.027 (3)	0.003 (2)	0.000 (2)	0.002 (2)

Br—C2	1.897 (5)	C3—C4	1.392 (7)
O1—C7	1.322 (6)	C3—C7	1.507 (7)
O1—H1	0.8400	C4—C5	1.388 (7)
O2—C7	1.213 (6)	C4—H4	0.9500
N1—C2	1.340 (6)	C5—C6	1.378 (7)
N1—C6	1.356 (6)	C5—H5	0.9500
C2—C3	1.400 (7)	C6—H6	0.9500
C7—O1—H1	109.5	C3—C4—H4	119.5
C2—N1—C6	118.4 (4)	C6—C5—C4	118.1 (5)
N1—C2—C3	123.3 (5)	C6—C5—H5	121.0
N1—C2—Br	113.2 (3)	C4—C5—H5	121.0
C3—C2—Br	123.5 (4)	N1—C6—C5	122.6 (4)
C4—C3—C2	116.7 (5)	N1—C6—H6	118.7
C4—C3—C7	118.1 (4)	C5—C6—H6	118.7
C2—C3—C7	125.2 (4)	O2—C7—O1	123.7 (5)
C5—C4—C3	120.9 (5)	O2—C7—C3	123.8 (5)
C5—C4—H4	119.5	O1—C7—C3	112.6 (4)
C2—C3—C7—O1	161.1 (5)	C2—C3—C7—O2	−20.1 (9)
C4—C3—C7—O1	−20.7 (7)	C4—C3—C7—O2	158.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.84	1.85	2.685 (5)	173
C5—H5···O2ii	0.95	2.39	3.258 (7)	152
C6—H6···O2iii	0.95	2.47	3.171 (6)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.84	1.85	2.685 (5)	173
C5—H5⋯O2ii	0.95	2.39	3.258 (7)	152
C6—H6⋯O2iii	0.95	2.47	3.171 (6)	131

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