2-Bromo-benzaldehyde cyano-hydrin.

The title compound [alternatively called (2-bromo-phen-yl)-(hydr-oxy)acetonitrile], C(8)H(6)BrNO, is the reaction product of 2-bromo-benzaldehyde and hydrogen cyanide. Bond lengths and angles are normal. In the crystal structure, an intermolecular hydrogen bond between the hydr-oxy group and the nitrile N atom is established. In agreement with bonding considerations, a linear C-N⋯H acceptor geometry is observed. Each mol-ecule is a single donor and a single acceptor; extended hydrogen-bonded chains are formed along [100].

Related literature

For the synthesis of the title compound, see: Becker et al. (2001 ▶). For the crystal structure of a related compound, see: Flores-Morales et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H6BrNO

M = 212.05

Orthorhombic,

a = 8.0538 (3) Å

b = 13.9970 (5) Å

c = 14.2969 (5) Å

V = 1611.68 (10) Å3

Z = 8

Mo Kα radiation

μ = 5.04 mm−1

T = 200 (2) K

0.14 × 0.09 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.624, T max = 0.86

19593 measured reflections

1844 independent reflections

1351 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.083

S = 1.02

1844 reflections

102 parameters

Only H-atom displacement parameters refined

Δρmax = 0.29 e Å−3

Δρmin = −0.59 e Å−3

Data collection: COLLECT (Nonius, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807049604/lh2526sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807049604/lh2526Isup2.hkl

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

C8H6BrNO	F000 = 832
Mr = 212.05	Dx = 1.748 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 10818 reflections
a = 8.0538 (3) Å	θ = 3.1–27.5º
b = 13.9970 (5) Å	µ = 5.04 mm−1
c = 14.2969 (5) Å	T = 200 (2) K
V = 1611.68 (10) Å3	Platelet, colourless
Z = 8	0.14 × 0.09 × 0.03 mm

Nonius KappaCCD diffractometer	1844 independent reflections
Radiation source: rotating anode	1351 reflections with I > 2σ(I)
Monochromator: MONTEL, graded multilayered X-ray optics	Rint = 0.040
T = 200(2) K	θmax = 27.5º
CCD; rotation images; thick slices scans	θmin = 3.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.624, Tmax = 0.86	k = −18→15
19593 measured reflections	l = −18→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Only H-atom displacement parameters refined
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.038P)2 + 1.1081P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1844 reflections	Δρmax = 0.29 e Å−3
102 parameters	Δρmin = −0.59 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
Br	0.25307 (3)	0.16689 (2)	0.310767 (19)	0.04887 (13)
O	0.1470 (3)	0.09045 (13)	0.01121 (14)	0.0533 (5)
H82	0.0823	0.1302	−0.0135	0.055 (3)*
N	0.4211 (3)	0.26649 (17)	0.05011 (16)	0.0501 (6)
C1	0.3312 (3)	0.20716 (18)	0.07017 (16)	0.0367 (5)
C2	0.2128 (3)	0.12902 (19)	0.09341 (17)	0.0364 (5)
H2	0.1206	0.1552	0.1327	0.055 (3)*
C3	0.3037 (3)	0.05167 (17)	0.14759 (16)	0.0309 (5)
C4	0.3299 (3)	0.05819 (17)	0.24325 (16)	0.0330 (5)
C5	0.4107 (3)	−0.01275 (19)	0.29246 (18)	0.0410 (6)
H5	0.4253	−0.0075	0.3582	0.055 (3)*
C6	0.4697 (4)	−0.09138 (18)	0.2449 (2)	0.0469 (7)
H6	0.5261	−0.1405	0.2779	0.055 (3)*
C7	0.4473 (3)	−0.09931 (18)	0.1491 (2)	0.0443 (6)
H7	0.4899	−0.1531	0.1164	0.055 (3)*
C8	0.3623 (3)	−0.02833 (17)	0.10115 (18)	0.0392 (6)
H8	0.3442	−0.0347	0.0358	0.055 (3)*

	U11	U22	U33	U12	U13	U23
Br	0.0455 (2)	0.0566 (2)	0.04446 (19)	0.00087 (13)	−0.00098 (12)	−0.01748 (11)
O	0.0627 (14)	0.0467 (11)	0.0505 (12)	0.0086 (9)	−0.0308 (10)	−0.0072 (9)
N	0.0567 (15)	0.0477 (14)	0.0458 (13)	−0.0024 (12)	0.0043 (11)	0.0100 (11)
C1	0.0415 (14)	0.0352 (13)	0.0334 (12)	0.0049 (12)	0.0002 (11)	0.0049 (10)
C2	0.0362 (13)	0.0366 (13)	0.0363 (12)	0.0030 (11)	−0.0045 (10)	−0.0020 (11)
C3	0.0259 (10)	0.0319 (11)	0.0350 (12)	−0.0025 (9)	−0.0007 (10)	0.0051 (10)
C4	0.0272 (12)	0.0357 (12)	0.0361 (12)	−0.0071 (10)	0.0011 (10)	−0.0009 (10)
C5	0.0396 (14)	0.0482 (15)	0.0352 (12)	−0.0121 (12)	−0.0060 (11)	0.0110 (11)
C6	0.0435 (16)	0.0375 (14)	0.0596 (18)	−0.0003 (12)	−0.0086 (14)	0.0154 (13)
C7	0.0455 (16)	0.0302 (13)	0.0573 (17)	0.0032 (11)	−0.0012 (13)	−0.0015 (12)
C8	0.0427 (14)	0.0371 (14)	0.0378 (12)	−0.0015 (11)	0.0004 (11)	0.0001 (10)

Br—C4	1.905 (2)	C4—C5	1.380 (3)
O—C2	1.398 (3)	C5—C6	1.379 (4)
O—H82	0.8400	C5—H5	0.9500
N—C1	1.138 (3)	C6—C7	1.386 (4)
C1—C2	1.489 (4)	C6—H6	0.9500
C2—C3	1.519 (3)	C7—C8	1.387 (4)
C2—H2	1.0000	C7—H7	0.9500
C3—C8	1.385 (3)	C8—H8	0.9500
C3—C4	1.387 (3)
C2—O—H82	109.5	C3—C4—Br	120.18 (17)
N—C1—C2	178.3 (3)	C6—C5—C4	119.0 (2)
O—C2—C1	109.8 (2)	C6—C5—H5	120.5
O—C2—C3	109.6 (2)	C4—C5—H5	120.5
C1—C2—C3	109.2 (2)	C5—C6—C7	120.5 (2)
O—C2—H2	109.4	C5—C6—H6	119.8
C1—C2—H2	109.4	C7—C6—H6	119.8
C3—C2—H2	109.4	C6—C7—C8	119.7 (2)
C8—C3—C4	118.3 (2)	C6—C7—H7	120.2
C8—C3—C2	119.7 (2)	C8—C7—H7	120.2
C4—C3—C2	122.0 (2)	C3—C8—C7	120.7 (2)
C5—C4—C3	121.8 (2)	C3—C8—H8	119.6
C5—C4—Br	118.01 (19)	C7—C8—H8	119.6
O—C2—C3—C8	22.9 (3)	C3—C4—C5—C6	1.3 (4)
C1—C2—C3—C8	−97.4 (3)	Br—C4—C5—C6	−178.99 (19)
O—C2—C3—C4	−156.8 (2)	C4—C5—C6—C7	−0.4 (4)
C1—C2—C3—C4	82.9 (3)	C5—C6—C7—C8	−1.1 (4)
C8—C3—C4—C5	−0.6 (3)	C4—C3—C8—C7	−1.0 (4)
C2—C3—C4—C5	179.1 (2)	C2—C3—C8—C7	179.3 (2)
C8—C3—C4—Br	179.68 (18)	C6—C7—C8—C3	1.8 (4)
C2—C3—C4—Br	−0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O—H82···Ni	0.84	2.01	2.844 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O—H82⋯Ni	0.84	2.01	2.844 (3)	170

Symmetry code: (i) .