2-Azido-1-(4-fluoro-phen-yl)ethanone.

The crystal structure of the title compound, C(8)H(6)FN(3)O, is stabilized by C-H⋯O hydrogen bonds, which link the mol-ecules into chains running parallel to the a axis.

Related literature

The title compound is an inter­mediate obtained during an attempt to synthesize biologically active triazoles. For the biological activity of triazoles, see: Genin et al. (2000 ▶); Parmee et al. (2000 ▶); Koble et al. (1995 ▶); Moltzen et al. (1994 ▶). For standard bond lengths: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H6FN3O

M = 179.16

Orthorhombic,

a = 10.7985 (16) Å

b = 8.3971 (12) Å

c = 17.485 (3) Å

V = 1585.5 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 273 K

0.35 × 0.28 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.959, T max = 0.976

8606 measured reflections

1476 independent reflections

1239 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.06

1476 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013426/rz2730sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013426/rz2730Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013426/rz2730Isup3.cml

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

C8H6FN3O	F(000) = 736
Mr = 179.16	Dx = 1.501 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2831 reflections
a = 10.7985 (16) Å	θ = 2.3–27.8°
b = 8.3971 (12) Å	µ = 0.12 mm−1
c = 17.485 (3) Å	T = 273 K
V = 1585.5 (4) Å3	Block, colourless
Z = 8	0.35 × 0.28 × 0.20 mm

Bruker SMART APEX CCD area-detector diffractometer	1476 independent reflections
Radiation source: fine-focus sealed tube	1239 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω scan	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→13
Tmin = 0.959, Tmax = 0.976	k = −10→10
8606 measured reflections	l = −21→21

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0469P)2 + 0.2956P] where P = (Fo2 + 2Fc2)/3
1476 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
O1	0.61761 (8)	0.03188 (12)	0.73973 (5)	0.0358 (3)
N1	0.77319 (12)	−0.13811 (15)	0.83252 (7)	0.0361 (3)
N2	0.68380 (11)	−0.09577 (14)	0.87237 (7)	0.0336 (3)
N3	0.60363 (13)	−0.07646 (17)	0.91283 (7)	0.0451 (4)
C1	0.89336 (12)	0.19093 (16)	0.64990 (8)	0.0305 (3)
H1B	0.9536	0.1521	0.6830	0.037*
C2	0.92779 (14)	0.28254 (17)	0.58742 (8)	0.0348 (4)
H2A	1.0106	0.3060	0.5782	0.042*
C3	0.83684 (14)	0.33759 (17)	0.53966 (8)	0.0342 (3)
C4	0.71318 (14)	0.30861 (18)	0.55138 (8)	0.0366 (4)
H4A	0.6536	0.3492	0.5182	0.044*
C5	0.67981 (13)	0.21777 (17)	0.61363 (8)	0.0333 (3)
H5A	0.5965	0.1968	0.6227	0.040*
C6	0.76889 (12)	0.15677 (16)	0.66330 (7)	0.0273 (3)
C7	0.72692 (12)	0.05618 (16)	0.72799 (7)	0.0277 (3)
C8	0.82354 (13)	−0.01705 (17)	0.78080 (8)	0.0313 (3)
H8A	0.8882	−0.0650	0.7499	0.038*
H8B	0.8611	0.0669	0.8110	0.038*
F1	0.87045 (9)	0.42468 (11)	0.47751 (5)	0.0478 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0225 (6)	0.0481 (6)	0.0370 (5)	−0.0033 (4)	−0.0003 (4)	−0.0021 (5)
N1	0.0337 (7)	0.0341 (7)	0.0405 (7)	0.0037 (5)	0.0029 (6)	0.0004 (5)
N2	0.0346 (7)	0.0329 (7)	0.0333 (6)	−0.0019 (5)	−0.0049 (6)	0.0031 (5)
N3	0.0413 (8)	0.0548 (9)	0.0392 (7)	0.0024 (7)	0.0065 (6)	0.0069 (6)
C1	0.0248 (7)	0.0338 (8)	0.0328 (7)	0.0029 (6)	−0.0019 (6)	−0.0054 (6)
C2	0.0293 (8)	0.0374 (8)	0.0376 (7)	−0.0015 (6)	0.0049 (6)	−0.0064 (6)
C3	0.0414 (9)	0.0314 (7)	0.0299 (7)	−0.0013 (6)	0.0036 (6)	−0.0031 (6)
C4	0.0355 (9)	0.0378 (8)	0.0366 (8)	0.0021 (6)	−0.0068 (6)	−0.0006 (6)
C5	0.0260 (7)	0.0343 (8)	0.0394 (8)	0.0003 (6)	−0.0025 (6)	−0.0041 (6)
C6	0.0241 (7)	0.0274 (7)	0.0304 (7)	0.0011 (6)	0.0005 (5)	−0.0075 (5)
C7	0.0232 (7)	0.0287 (7)	0.0313 (7)	0.0004 (5)	−0.0009 (5)	−0.0098 (5)
C8	0.0254 (7)	0.0336 (7)	0.0348 (7)	−0.0004 (6)	0.0003 (6)	−0.0012 (6)
F1	0.0544 (6)	0.0501 (6)	0.0389 (5)	−0.0045 (4)	0.0040 (4)	0.0089 (4)

O1—C7	1.2154 (16)	C3—C4	1.373 (2)
N1—N2	1.2425 (17)	C4—C5	1.377 (2)
N1—C8	1.4652 (19)	C4—H4A	0.9300
N2—N3	1.1296 (17)	C5—C6	1.3936 (19)
C1—C2	1.387 (2)	C5—H5A	0.9300
C1—C6	1.3942 (19)	C6—C7	1.4826 (19)
C1—H1B	0.9300	C7—C8	1.5229 (19)
C2—C3	1.370 (2)	C8—H8A	0.9700
C2—H2A	0.9300	C8—H8B	0.9700
C3—F1	1.3591 (16)
N2—N1—C8	115.85 (12)	C4—C5—H5A	119.5
N3—N2—N1	170.98 (14)	C6—C5—H5A	119.5
C2—C1—C6	120.33 (13)	C5—C6—C1	119.02 (13)
C2—C1—H1B	119.8	C5—C6—C7	118.29 (12)
C6—C1—H1B	119.8	C1—C6—C7	122.69 (12)
C3—C2—C1	118.38 (13)	O1—C7—C6	121.43 (12)
C3—C2—H2A	120.8	O1—C7—C8	119.67 (12)
C1—C2—H2A	120.8	C6—C7—C8	118.90 (11)
F1—C3—C2	118.53 (13)	N1—C8—C7	113.59 (12)
F1—C3—C4	118.33 (13)	N1—C8—H8A	108.8
C2—C3—C4	123.14 (14)	C7—C8—H8A	108.8
C3—C4—C5	118.09 (14)	N1—C8—H8B	108.8
C3—C4—H4A	121.0	C7—C8—H8B	108.8
C5—C4—H4A	121.0	H8A—C8—H8B	107.7
C4—C5—C6	121.04 (13)
C6—C1—C2—C3	−0.2 (2)	C2—C1—C6—C7	178.42 (12)
C1—C2—C3—F1	−178.68 (12)	C5—C6—C7—O1	−2.87 (19)
C1—C2—C3—C4	1.1 (2)	C1—C6—C7—O1	177.86 (12)
F1—C3—C4—C5	178.78 (12)	C5—C6—C7—C8	177.46 (12)
C2—C3—C4—C5	−1.0 (2)	C1—C6—C7—C8	−1.81 (18)
C3—C4—C5—C6	−0.1 (2)	N2—N1—C8—C7	−54.22 (16)
C4—C5—C6—C1	1.0 (2)	O1—C7—C8—N1	11.84 (17)
C4—C5—C6—C7	−178.34 (12)	C6—C7—C8—N1	−168.49 (11)
C2—C1—C6—C5	−0.84 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1i	0.93	2.45	3.3722 (17)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1i	0.93	2.45	3.3722 (17)	174

Symmetry code: (i) .