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

In the title compound, C(8)H(6)N(4)O(3), the ketone [C-C(=O)-C] and nitro groups are tilted with respect to the benzene ring by 18.92 (6) and 24.11 (15)°, respectively. In the crystal, mol-ecules are linked into inter-woven chains running parallel to the [100] direction by C-H⋯N hydrogen bonds and weak π-π stacking inter-actions, with centroid-centroid separations of 3.897 (3) Å.

Related literature

For the crystal structure of the related compound 2-azido-1-(4-fluoro­phen­yl)ethanone, see: Yousuf et al. (2012 ▶). For the biological activities of triazoles, see: Genin et al. (2000 ▶); Parmee et al. (2000 ▶); Koble et al. (1995 ▶); Moltzen et al. (1994 ▶).

Experimental

Crystal data

C8H6N4O3

M = 206.17

Orthorhombic,

a = 7.6307 (5) Å

b = 9.5168 (6) Å

c = 12.4097 (8) Å

V = 901.19 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 273 K

0.50 × 0.23 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.942, T max = 0.987

4914 measured reflections

1649 independent reflections

1461 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.074

S = 1.06

1649 reflections

136 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.11 e Å−3

Absolute structure: Flack (1983 ▶), 767 Friedel pairs

Flack parameter: 0.2 (14)

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/S1600536812021241/rz2752sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021241/rz2752Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021241/rz2752Isup3.cml

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

C8H6N4O3	F(000) = 424
Mr = 206.17	Dx = 1.520 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c 2ac	Cell parameters from 1557 reflections
a = 7.6307 (5) Å	θ = 3.3–24.2°
b = 9.5168 (6) Å	µ = 0.12 mm−1
c = 12.4097 (8) Å	T = 273 K
V = 901.19 (10) Å3	Block, colourles
Z = 4	0.50 × 0.23 × 0.11 mm

Bruker SMART APEX CCD area-detector diffractometer	1649 independent reflections
Radiation source: fine-focus sealed tube	1461 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scan	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.942, Tmax = 0.987	k = −11→11
4914 measured reflections	l = −15→15

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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0342P)2 + 0.0663P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1649 reflections	Δρmax = 0.11 e Å−3
136 parameters	Δρmin = −0.11 e Å−3
1 restraint	Absolute structure: Flack (1983), 767 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.2 (14)

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	0.9428 (3)	1.19359 (17)	0.40028 (13)	0.0815 (5)
O2	0.9798 (2)	1.30833 (17)	0.54808 (15)	0.0744 (5)
O3	0.6676 (2)	0.72287 (15)	0.81581 (12)	0.0673 (4)
N1	0.9448 (2)	1.20158 (19)	0.49879 (14)	0.0553 (5)
N2	0.7720 (3)	0.45389 (18)	0.76819 (14)	0.0603 (5)
N3	0.8183 (2)	0.45144 (17)	0.86298 (15)	0.0553 (4)
N4	0.8503 (3)	0.4344 (2)	0.95022 (17)	0.0740 (6)
C1	0.9238 (2)	0.9459 (2)	0.51250 (14)	0.0478 (5)
H1A	0.9657	0.9388	0.4423	0.057*
C2	0.8824 (3)	0.8273 (2)	0.57102 (15)	0.0472 (5)
H2B	0.8991	0.7389	0.5407	0.057*
C3	0.8160 (2)	0.83847 (19)	0.67466 (14)	0.0418 (4)
C4	0.7943 (2)	0.9715 (2)	0.71966 (14)	0.0474 (5)
H4A	0.7489	0.9796	0.7889	0.057*
C5	0.8386 (2)	1.0906 (2)	0.66373 (16)	0.0482 (4)
H5A	0.8264	1.1791	0.6946	0.058*
C6	0.9017 (2)	1.0752 (2)	0.56038 (14)	0.0438 (4)
C7	0.7632 (3)	0.7125 (2)	0.73869 (14)	0.0459 (4)
C8	0.8367 (3)	0.57217 (19)	0.70483 (15)	0.0520 (5)
H8A	0.8079	0.5563	0.6297	0.062*
H8B	0.9634	0.5754	0.7107	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.1121 (14)	0.0726 (11)	0.0598 (10)	−0.0001 (10)	0.0104 (9)	0.0177 (8)
O2	0.0870 (11)	0.0473 (9)	0.0889 (12)	−0.0090 (8)	−0.0091 (10)	0.0089 (9)
O3	0.0804 (11)	0.0609 (9)	0.0606 (8)	−0.0032 (7)	0.0250 (8)	0.0022 (7)
N1	0.0540 (10)	0.0514 (12)	0.0607 (12)	0.0034 (8)	−0.0015 (9)	0.0086 (9)
N2	0.0725 (12)	0.0476 (10)	0.0607 (10)	−0.0110 (9)	−0.0118 (9)	0.0040 (8)
N3	0.0606 (11)	0.0435 (9)	0.0617 (11)	−0.0068 (8)	−0.0014 (9)	0.0033 (8)
N4	0.0883 (14)	0.0733 (14)	0.0603 (11)	−0.0078 (11)	−0.0024 (11)	0.0088 (10)
C1	0.0507 (10)	0.0538 (13)	0.0390 (9)	0.0025 (9)	0.0020 (8)	−0.0012 (9)
C2	0.0520 (10)	0.0424 (11)	0.0472 (10)	0.0023 (9)	0.0000 (9)	−0.0059 (8)
C3	0.0402 (9)	0.0447 (11)	0.0406 (9)	−0.0012 (8)	−0.0020 (8)	−0.0021 (8)
C4	0.0498 (10)	0.0512 (12)	0.0413 (9)	−0.0013 (9)	0.0033 (8)	−0.0052 (9)
C5	0.0510 (10)	0.0419 (11)	0.0516 (10)	0.0002 (8)	−0.0032 (9)	−0.0080 (9)
C6	0.0399 (9)	0.0439 (11)	0.0475 (9)	−0.0005 (8)	−0.0050 (8)	0.0046 (9)
C7	0.0460 (9)	0.0490 (11)	0.0426 (9)	−0.0047 (9)	−0.0030 (9)	−0.0025 (8)
C8	0.0594 (12)	0.0456 (12)	0.0510 (10)	−0.0008 (10)	−0.0012 (10)	0.0031 (9)

O1—N1	1.225 (2)	C2—H2B	0.9300
O2—N1	1.216 (2)	C3—C4	1.393 (3)
O3—C7	1.207 (2)	C3—C7	1.493 (3)
N1—C6	1.462 (2)	C4—C5	1.372 (3)
N2—N3	1.229 (2)	C4—H4A	0.9300
N2—C8	1.459 (2)	C5—C6	1.378 (3)
N3—N4	1.122 (2)	C5—H5A	0.9300
C1—C6	1.377 (3)	C7—C8	1.508 (3)
C1—C2	1.379 (3)	C8—H8A	0.9700
C1—H1A	0.9300	C8—H8B	0.9700
C2—C3	1.386 (2)
O2—N1—O1	123.83 (18)	C3—C4—H4A	119.4
O2—N1—C6	118.28 (16)	C4—C5—C6	118.00 (18)
O1—N1—C6	117.89 (18)	C4—C5—H5A	121.0
N3—N2—C8	115.67 (17)	C6—C5—H5A	121.0
N4—N3—N2	171.7 (2)	C1—C6—C5	122.64 (18)
C6—C1—C2	118.44 (17)	C1—C6—N1	118.80 (16)
C6—C1—H1A	120.8	C5—C6—N1	118.55 (18)
C2—C1—H1A	120.8	O3—C7—C3	121.29 (19)
C1—C2—C3	120.62 (18)	O3—C7—C8	121.17 (19)
C1—C2—H2B	119.7	C3—C7—C8	117.52 (15)
C3—C2—H2B	119.7	N2—C8—C7	114.03 (16)
C2—C3—C4	119.02 (17)	N2—C8—H8A	108.7
C2—C3—C7	122.04 (17)	C7—C8—H8A	108.7
C4—C3—C7	118.93 (15)	N2—C8—H8B	108.7
C5—C4—C3	121.25 (16)	C7—C8—H8B	108.7
C5—C4—H4A	119.4	H8A—C8—H8B	107.6
C8—N2—N3—N4	−176.5 (17)	O2—N1—C6—C1	−156.72 (18)
C6—C1—C2—C3	1.5 (3)	O1—N1—C6—C1	23.6 (2)
C1—C2—C3—C4	−1.0 (3)	O2—N1—C6—C5	24.0 (2)
C1—C2—C3—C7	177.54 (16)	O1—N1—C6—C5	−155.73 (18)
C2—C3—C4—C5	−0.6 (3)	C2—C3—C7—O3	−161.46 (19)
C7—C3—C4—C5	−179.14 (16)	C4—C3—C7—O3	17.1 (3)
C3—C4—C5—C6	1.5 (3)	C2—C3—C7—C8	19.8 (2)
C2—C1—C6—C5	−0.6 (3)	C4—C3—C7—C8	−161.67 (16)
C2—C1—C6—N1	−179.83 (16)	N3—N2—C8—C7	−67.2 (3)
C4—C5—C6—C1	−0.9 (3)	O3—C7—C8—N2	4.1 (3)
C4—C5—C6—N1	178.33 (16)	C3—C7—C8—N2	−177.17 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···N2i	0.97	2.48	3.422 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯N2i	0.97	2.48	3.422 (3)	165

Symmetry code: (i) .