4'-Fluoro-2'-hydroxy-acetophenone.

The title compound, C(8)H(7)FO(2), crystallizes as discrete mol-ecules, the conformation of which may be influenced by an intra-molecular hydr-oxy-carbonyl O-H⋯O hydrogen bond.

Related literature

For the crystal structures of other substituted acetophenones, see: Filarowski et al. (2004 ▶, 2005 ▶); Hibbs et al. (2003 ▶); Huang et al. (2004 ▶); Ng (2007 ▶); Xu et al. (2005 ▶).

Experimental

Crystal data

C8H7FO2

M = 154.14

Monoclinic,

a = 3.7978 (1) Å

b = 14.2421 (3) Å

c = 13.0092 (3) Å

β = 91.884 (2)°

V = 703.27 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 (2) K

0.16 × 0.14 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

8762 measured reflections

1601 independent reflections

1224 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.127

S = 1.05

1601 reflections

128 parameters

7 restraints

All H-atom parameters refined

Δρmax = 0.30 e Å−3

Δρmin = −0.28 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011173/lh2605sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011173/lh2605Isup2.hkl

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

C8H7FO2	F000 = 320
Mr = 154.14	Dx = 1.456 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1854 reflections
a = 3.7978 (1) Å	θ = 2.9–26.4º
b = 14.2421 (3) Å	µ = 0.12 mm−1
c = 13.0092 (3) Å	T = 100 (2) K
β = 91.884 (2)º	Prism, colorless
V = 703.27 (3) Å3	0.16 × 0.14 × 0.12 mm
Z = 4

Bruker SMART APEXII diffractometer	1224 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
Monochromator: graphite	θmax = 27.5º
T = 100(2) K	θmin = 2.1º
ω scans	h = −4→4
Absorption correction: none	k = −18→18
8762 measured reflections	l = −16→16
1601 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	All H-atom parameters refined
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0775P)2 + 0.0798P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
1601 reflections	Δρmax = 0.30 e Å−3
128 parameters	Δρmin = −0.28 e Å−3
7 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
F1	0.1828 (3)	0.50469 (6)	0.65495 (7)	0.0319 (3)
O1	0.4466 (3)	0.72547 (8)	0.40329 (8)	0.0325 (3)
O2	0.7055 (3)	0.88271 (8)	0.46250 (8)	0.0320 (3)
C1	0.5542 (4)	0.76649 (10)	0.58170 (11)	0.0196 (3)
C2	0.4380 (4)	0.70349 (10)	0.50349 (11)	0.0211 (3)
C3	0.3106 (4)	0.61483 (10)	0.52868 (11)	0.0229 (3)
C4	0.3051 (4)	0.59128 (10)	0.63045 (12)	0.0225 (4)
C5	0.4165 (4)	0.64954 (10)	0.71015 (11)	0.0235 (4)
C6	0.5398 (4)	0.73716 (10)	0.68410 (11)	0.0216 (4)
C7	0.6909 (4)	0.85914 (10)	0.55377 (11)	0.0227 (4)
C8	0.8132 (5)	0.92675 (11)	0.63595 (12)	0.0267 (4)
H1	0.519 (6)	0.7824 (9)	0.4037 (19)	0.066 (8)*
H3	0.221 (5)	0.5733 (10)	0.4729 (11)	0.029 (5)*
H5	0.412 (5)	0.6279 (11)	0.7807 (8)	0.023 (4)*
H6	0.616 (4)	0.7801 (10)	0.7398 (10)	0.024 (4)*
H81	0.602 (4)	0.9492 (14)	0.6716 (15)	0.051 (6)*
H82	0.968 (4)	0.8980 (12)	0.6899 (12)	0.033 (5)*
H83	0.937 (5)	0.9790 (11)	0.6047 (15)	0.044 (5)*

	U11	U22	U33	U12	U13	U23
F1	0.0427 (6)	0.0200 (5)	0.0331 (5)	−0.0081 (4)	0.0043 (4)	0.0043 (4)
O1	0.0514 (8)	0.0275 (6)	0.0182 (6)	−0.0115 (6)	−0.0021 (5)	0.0018 (4)
O2	0.0457 (8)	0.0252 (6)	0.0254 (6)	−0.0091 (5)	0.0038 (5)	0.0027 (4)
C1	0.0191 (8)	0.0176 (7)	0.0221 (7)	0.0013 (5)	0.0012 (6)	−0.0019 (5)
C2	0.0223 (8)	0.0221 (8)	0.0187 (7)	−0.0003 (6)	0.0002 (6)	0.0003 (5)
C3	0.0235 (8)	0.0207 (7)	0.0244 (8)	−0.0012 (6)	−0.0003 (6)	−0.0023 (6)
C4	0.0227 (8)	0.0146 (7)	0.0304 (8)	−0.0005 (6)	0.0045 (6)	0.0030 (6)
C5	0.0266 (9)	0.0240 (8)	0.0201 (7)	0.0020 (6)	0.0028 (6)	0.0026 (6)
C6	0.0226 (8)	0.0205 (7)	0.0217 (7)	0.0022 (6)	0.0007 (6)	−0.0022 (5)
C7	0.0231 (8)	0.0204 (7)	0.0247 (8)	0.0006 (6)	0.0021 (6)	−0.0004 (6)
C8	0.0277 (9)	0.0220 (8)	0.0304 (8)	−0.0035 (6)	0.0026 (7)	−0.0032 (6)

F1—C4	1.3594 (16)	C3—H3	0.988 (9)
O1—C2	1.3420 (17)	C4—C5	1.383 (2)
O1—H1	0.857 (10)	C5—C6	1.379 (2)
O2—C7	1.2370 (18)	C5—H5	0.969 (9)
C1—C6	1.399 (2)	C6—H6	0.984 (9)
C1—C2	1.416 (2)	C7—C8	1.501 (2)
C1—C7	1.468 (2)	C8—H81	0.993 (10)
C2—C3	1.395 (2)	C8—H82	0.989 (9)
C3—C4	1.367 (2)	C8—H83	0.977 (10)
C2—O1—H1	103.5 (17)	C6—C5—H5	122.5 (10)
C6—C1—C2	118.29 (13)	C4—C5—H5	120.3 (10)
C6—C1—C7	121.96 (13)	C5—C6—C1	121.90 (13)
C2—C1—C7	119.74 (13)	C5—C6—H6	118.4 (10)
O1—C2—C3	117.32 (13)	C1—C6—H6	119.7 (10)
O1—C2—C1	122.21 (13)	O2—C7—C1	120.59 (13)
C3—C2—C1	120.47 (13)	O2—C7—C8	119.14 (14)
C4—C3—C2	117.78 (14)	C1—C7—C8	120.27 (13)
C4—C3—H3	123.3 (11)	C7—C8—H81	107.6 (13)
C2—C3—H3	118.9 (10)	C7—C8—H82	113.7 (11)
F1—C4—C3	117.77 (13)	H81—C8—H82	105.8 (17)
F1—C4—C5	117.83 (13)	C7—C8—H83	109.5 (12)
C3—C4—C5	124.40 (14)	H81—C8—H83	111.0 (18)
C6—C5—C4	117.17 (13)	H82—C8—H83	109.2 (17)
C6—C1—C2—O1	−179.20 (14)	C3—C4—C5—C6	0.2 (2)
C7—C1—C2—O1	−0.3 (2)	C4—C5—C6—C1	−0.3 (2)
C6—C1—C2—C3	0.4 (2)	C2—C1—C6—C5	0.0 (2)
C7—C1—C2—C3	179.37 (14)	C7—C1—C6—C5	−178.94 (14)
O1—C2—C3—C4	179.15 (14)	C6—C1—C7—O2	178.92 (14)
C1—C2—C3—C4	−0.5 (2)	C2—C1—C7—O2	0.0 (2)
C2—C3—C4—F1	−179.64 (13)	C6—C1—C7—C8	−1.4 (2)
C2—C3—C4—C5	0.2 (2)	C2—C1—C7—C8	179.68 (14)
F1—C4—C5—C6	−179.97 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.857 (10)	1.76 (1)	2.554 (2)	154 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.857 (10)	1.76 (1)	2.554 (2)	154 (2)