5-Bromo-2-hy-droxy-benzonitrile.

The title compound, C(7)H(4)BrNO, crystallizes with two mol-ecules in the asymmetric unit. The two molecules exhibit nearly linear C-C N nitrile bond angles of 179.1 (4) and 177.1 (4)°. In the crystal, the mol-ecules are linked into a one-dimensional hydrogen-bonded chain by inter-actions between the phenol H atom and the nitrile N atom [N⋯O = 2.805 (4) and 2.810 (4) Å].

Related literature

For information on the synthesis of the title compound, see: Anwar & Hansen (2008 ▶); Bonnichon et al. (1999 ▶); Oberhauser (1997 ▶); Tamilselvan et al. (2009 ▶). For use as a synthetic reagent, see: Jiang et al. (2011 ▶); Tsuhako et al. (2012 ▶); Wetzel et al. (2011 ▶). For a related crystal structure, see: Beswick et al. (1996 ▶).

Experimental

Crystal data

C7H4BrNO

M = 198.01

Triclinic,

a = 3.8422 (3) Å

b = 8.5166 (7) Å

c = 21.6507 (18) Å

α = 97.074 (1)°

β = 91.991 (1)°

γ = 97.068 (1)°

V = 696.83 (10) Å3

Z = 4

Mo Kα radiation

μ = 5.82 mm−1

T = 125 K

0.20 × 0.07 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.389, T max = 0.845

11040 measured reflections

4213 independent reflections

3254 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.100

S = 1.03

4213 reflections

187 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.67 e Å−3

Δρmin = −0.57 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812031716/rk2372sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031716/rk2372Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031716/rk2372Isup3.cml

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

C7H4BrNO	Z = 4
Mr = 198.01	F(000) = 384
Triclinic, P1	Dx = 1.888 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8422 (3) Å	Cell parameters from 5206 reflections
b = 8.5166 (7) Å	θ = 2.5–30.5°
c = 21.6507 (18) Å	µ = 5.82 mm−1
α = 97.074 (1)°	T = 125 K
β = 91.991 (1)°	Needle, colourless
γ = 97.068 (1)°	0.20 × 0.07 × 0.03 mm
V = 696.83 (10) Å3

Bruker APEXII CCD diffractometer	4213 independent reflections
Radiation source: fine-focus sealed tube	3254 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 30.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −5→5
Tmin = 0.389, Tmax = 0.845	k = −12→12
11040 measured reflections	l = −30→30

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.050P)2 + 0.6935P] where P = (Fo2 + 2Fc2)/3
4213 reflections	(Δ/σ)max = 0.001
187 parameters	Δρmax = 1.67 e Å−3
2 restraints	Δρmin = −0.57 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 > 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	0.18318 (9)	0.28671 (4)	0.512507 (15)	0.02561 (10)
Br2	0.29449 (9)	0.79771 (4)	0.004330 (16)	0.02483 (10)
O1	0.5299 (7)	0.0480 (3)	0.25051 (11)	0.0272 (5)
H1	0.477 (12)	0.107 (5)	0.2245 (17)	0.041*
O2	−0.0783 (7)	0.5153 (3)	0.23932 (11)	0.0256 (5)
H2	−0.155 (11)	0.581 (4)	0.2658 (16)	0.038*
N1	0.6255 (9)	−0.2737 (4)	0.32638 (14)	0.0297 (7)
N2	0.2873 (9)	0.2144 (4)	0.15707 (14)	0.0284 (7)
C1	0.5484 (9)	−0.1490 (4)	0.33933 (15)	0.0219 (6)
C2	0.4527 (8)	0.0091 (4)	0.35481 (15)	0.0198 (6)
C3	0.4427 (9)	0.1083 (4)	0.30815 (15)	0.0205 (6)
C4	0.3500 (9)	0.2610 (4)	0.32282 (16)	0.0243 (7)
H4A	0.3393	0.3289	0.2913	0.029*
C5	0.2735 (9)	0.3141 (4)	0.38330 (16)	0.0224 (6)
H5A	0.2114	0.4185	0.3933	0.027*
C6	0.2875 (8)	0.2141 (4)	0.42964 (15)	0.0200 (6)
C7	0.3737 (8)	0.0620 (4)	0.41583 (14)	0.0192 (6)
H7A	0.3793	−0.0061	0.4473	0.023*
C8	0.2157 (9)	0.3355 (4)	0.14778 (15)	0.0213 (6)
C9	0.1384 (8)	0.4920 (4)	0.13853 (15)	0.0188 (6)
C10	−0.0049 (8)	0.5841 (4)	0.18745 (15)	0.0196 (6)
C11	−0.0606 (9)	0.7398 (4)	0.17991 (15)	0.0211 (6)
H11A	−0.1568	0.8038	0.2124	0.025*
C12	0.0238 (9)	0.8011 (4)	0.12526 (16)	0.0218 (6)
H12A	−0.0129	0.9073	0.1205	0.026*
C13	0.1624 (8)	0.7076 (4)	0.07722 (15)	0.0190 (6)
C14	0.2219 (8)	0.5542 (4)	0.08324 (15)	0.0196 (6)
H14A	0.3182	0.4913	0.0504	0.023*

	U11	U22	U33	U12	U13	U23
Br1	0.02688 (19)	0.02853 (19)	0.02188 (17)	0.00764 (14)	0.00549 (13)	−0.00014 (13)
Br2	0.02437 (18)	0.02336 (17)	0.02838 (18)	0.00123 (13)	0.00333 (13)	0.01102 (13)
O1	0.0410 (15)	0.0240 (13)	0.0186 (11)	0.0098 (11)	0.0007 (10)	0.0047 (9)
O2	0.0380 (14)	0.0226 (12)	0.0173 (11)	0.0072 (11)	0.0050 (10)	0.0026 (9)
N1	0.0419 (19)	0.0259 (16)	0.0231 (15)	0.0104 (13)	0.0048 (13)	0.0035 (12)
N2	0.0417 (18)	0.0210 (15)	0.0223 (14)	0.0063 (13)	−0.0009 (13)	0.0004 (11)
C1	0.0268 (17)	0.0235 (17)	0.0159 (14)	0.0034 (13)	0.0015 (12)	0.0046 (12)
C2	0.0197 (15)	0.0184 (15)	0.0215 (15)	0.0034 (12)	0.0004 (12)	0.0024 (12)
C3	0.0193 (15)	0.0231 (16)	0.0184 (15)	0.0016 (12)	−0.0005 (12)	0.0018 (12)
C4	0.0289 (18)	0.0220 (16)	0.0230 (16)	0.0050 (13)	−0.0003 (13)	0.0058 (13)
C5	0.0246 (16)	0.0196 (15)	0.0235 (16)	0.0057 (12)	0.0008 (13)	0.0025 (12)
C6	0.0177 (15)	0.0242 (16)	0.0182 (15)	0.0036 (12)	0.0014 (12)	0.0023 (12)
C7	0.0204 (15)	0.0205 (15)	0.0170 (14)	0.0028 (12)	−0.0005 (12)	0.0040 (12)
C8	0.0268 (16)	0.0213 (16)	0.0154 (14)	0.0021 (13)	0.0010 (12)	0.0017 (12)
C9	0.0207 (15)	0.0170 (14)	0.0185 (14)	0.0031 (12)	−0.0004 (12)	0.0016 (11)
C10	0.0199 (15)	0.0179 (15)	0.0198 (15)	0.0002 (11)	−0.0021 (12)	0.0009 (12)
C11	0.0235 (16)	0.0183 (15)	0.0201 (15)	0.0026 (12)	−0.0008 (12)	−0.0021 (12)
C12	0.0218 (16)	0.0170 (15)	0.0260 (16)	0.0023 (12)	−0.0043 (13)	0.0025 (12)
C13	0.0175 (14)	0.0184 (15)	0.0209 (15)	−0.0009 (11)	0.0002 (12)	0.0051 (12)
C14	0.0167 (14)	0.0196 (15)	0.0214 (15)	0.0005 (11)	0.0003 (12)	0.0004 (12)

Br1—C6	1.897 (3)	C5—C6	1.397 (4)
Br2—C13	1.896 (3)	C5—H5A	0.9500
O1—C3	1.359 (4)	C6—C7	1.376 (4)
O1—H1	0.834 (19)	C7—H7A	0.9500
O2—C10	1.352 (4)	C8—C9	1.436 (4)
O2—H2	0.836 (19)	C9—C14	1.399 (4)
N1—C1	1.142 (4)	C9—C10	1.408 (4)
N2—C8	1.139 (4)	C10—C11	1.396 (4)
C1—C2	1.442 (4)	C11—C12	1.384 (5)
C2—C3	1.397 (4)	C11—H11A	0.9500
C2—C7	1.398 (4)	C12—C13	1.392 (5)
C3—C4	1.393 (5)	C12—H12A	0.9500
C4—C5	1.385 (5)	C13—C14	1.375 (4)
C4—H4A	0.9500	C14—H14A	0.9500
C3—O1—H1	110 (3)	C2—C7—H7A	120.4
C10—O2—H2	110 (3)	N2—C8—C9	177.1 (4)
N1—C1—C2	179.1 (4)	C14—C9—C10	120.9 (3)
C3—C2—C7	120.8 (3)	C14—C9—C8	120.4 (3)
C3—C2—C1	119.0 (3)	C10—C9—C8	118.6 (3)
C7—C2—C1	120.2 (3)	O2—C10—C11	124.1 (3)
O1—C3—C4	124.0 (3)	O2—C10—C9	117.3 (3)
O1—C3—C2	116.7 (3)	C11—C10—C9	118.7 (3)
C4—C3—C2	119.3 (3)	C12—C11—C10	120.2 (3)
C5—C4—C3	120.1 (3)	C12—C11—H11A	119.9
C5—C4—H4A	119.9	C10—C11—H11A	119.9
C3—C4—H4A	119.9	C11—C12—C13	120.2 (3)
C4—C5—C6	120.0 (3)	C11—C12—H12A	119.9
C4—C5—H5A	120.0	C13—C12—H12A	119.9
C6—C5—H5A	120.0	C14—C13—C12	121.0 (3)
C7—C6—C5	120.7 (3)	C14—C13—Br2	119.6 (2)
C7—C6—Br1	119.2 (2)	C12—C13—Br2	119.3 (2)
C5—C6—Br1	120.1 (2)	C13—C14—C9	118.9 (3)
C6—C7—C2	119.1 (3)	C13—C14—H14A	120.5
C6—C7—H7A	120.4	C9—C14—H14A	120.5
C7—C2—C3—O1	178.8 (3)	C14—C9—C10—O2	−180.0 (3)
C1—C2—C3—O1	−0.8 (5)	C8—C9—C10—O2	−3.4 (4)
C7—C2—C3—C4	−0.5 (5)	C14—C9—C10—C11	−0.4 (5)
C1—C2—C3—C4	179.9 (3)	C8—C9—C10—C11	176.2 (3)
O1—C3—C4—C5	−178.4 (3)	O2—C10—C11—C12	179.7 (3)
C2—C3—C4—C5	0.9 (5)	C9—C10—C11—C12	0.1 (5)
C3—C4—C5—C6	−0.3 (5)	C10—C11—C12—C13	0.5 (5)
C4—C5—C6—C7	−0.6 (5)	C11—C12—C13—C14	−0.8 (5)
C4—C5—C6—Br1	179.9 (3)	C11—C12—C13—Br2	−177.3 (2)
C5—C6—C7—C2	1.0 (5)	C12—C13—C14—C9	0.5 (5)
Br1—C6—C7—C2	−179.6 (2)	Br2—C13—C14—C9	177.0 (2)
C3—C2—C7—C6	−0.4 (5)	C10—C9—C14—C13	0.1 (5)
C1—C2—C7—C6	179.2 (3)	C8—C9—C14—C13	−176.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.83 (2)	1.98 (2)	2.805 (4)	170 (5)
O2—H2···N1i	0.84 (2)	1.98 (2)	2.810 (4)	175 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.83 (2)	1.98 (2)	2.805 (4)	170 (5)
O2—H2⋯N1i	0.84 (2)	1.98 (2)	2.810 (4)	175 (5)

Symmetry code: (i) .