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

In the mol-ecule of the title compound, C(9)H(9)N(3)O, the angle formed by the least-squares line through the azide group with the normal to the plane of the benzene plane ring is 46.62 (16)°. The crystal structure features C-H⋯O hydrogen bonds, which link the mol-ecules into zigzag chains running parallel to [010].

Related literature

For a related structure, see: Yousuf et al. (2012 ▶). For the biological activity of triazoles, see: Genin et al. (2000 ▶); Parmee et al. (2000 ▶); Koble et al. (1995 ▶); Moltzen et al. (1994 ▶).

Experimental

Crystal data

C9H9N3O

M = 175.19

Monoclinic,

a = 7.696 (3) Å

b = 9.025 (3) Å

c = 14.248 (4) Å

β = 118.726 (15)°

V = 867.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 273 K

0.30 × 0.21 × 0.17 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.973, T max = 0.985

4915 measured reflections

1595 independent reflections

1464 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.07

1595 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.28 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/S1600536812018491/rz2744sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018491/rz2744Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018491/rz2744Isup3.cml

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

C9H9N3O	F(000) = 368
Mr = 175.19	Dx = 1.341 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3299 reflections
a = 7.696 (3) Å	θ = 2.8–25.5°
b = 9.025 (3) Å	µ = 0.09 mm−1
c = 14.248 (4) Å	T = 273 K
β = 118.726 (15)°	Block, colourless
V = 867.8 (5) Å3	0.30 × 0.21 × 0.17 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1595 independent reflections
Radiation source: fine-focus sealed tube	1464 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω scan	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.973, Tmax = 0.985	k = −10→10
4915 measured reflections	l = −16→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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.1892P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1595 reflections	Δρmax = 0.24 e Å−3
120 parameters	Δρmin = −0.28 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (4)

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	0.37626 (11)	0.32286 (8)	0.67821 (6)	0.0259 (2)
N1	0.30617 (13)	0.53889 (11)	0.79105 (8)	0.0250 (3)
N2	0.46826 (13)	0.49335 (10)	0.86119 (7)	0.0220 (2)
N3	0.60533 (15)	0.45093 (11)	0.93395 (8)	0.0285 (3)
C1	0.27074 (15)	0.33313 (12)	0.45933 (9)	0.0225 (3)
H1B	0.3054	0.2413	0.4929	0.027*
C2	0.22351 (15)	0.34548 (12)	0.35311 (9)	0.0234 (3)
H2A	0.2257	0.2615	0.3159	0.028*
C3	0.17253 (15)	0.48218 (12)	0.30073 (9)	0.0217 (3)
C4	0.17304 (15)	0.60668 (12)	0.35936 (9)	0.0238 (3)
H4B	0.1425	0.6991	0.3264	0.029*
C5	0.21797 (15)	0.59490 (12)	0.46497 (9)	0.0226 (3)
H5A	0.2157	0.6789	0.5022	0.027*
C6	0.26701 (14)	0.45736 (11)	0.51680 (9)	0.0198 (3)
C7	0.31704 (14)	0.43963 (11)	0.63045 (9)	0.0201 (3)
C8	0.29227 (16)	0.57461 (12)	0.68730 (9)	0.0224 (3)
H8A	0.3935	0.6468	0.6981	0.027*
H8B	0.1643	0.6195	0.6418	0.027*
C9	0.11424 (17)	0.49495 (13)	0.18444 (9)	0.0275 (3)
H9A	0.1646	0.5861	0.1723	0.041*
H9B	−0.0276	0.4939	0.1426	0.041*
H9C	0.1684	0.4130	0.1640	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0310 (4)	0.0219 (4)	0.0239 (4)	0.0038 (3)	0.0125 (4)	0.0038 (3)
N1	0.0204 (5)	0.0313 (5)	0.0230 (5)	0.0014 (4)	0.0103 (4)	−0.0017 (4)
N2	0.0254 (5)	0.0220 (5)	0.0229 (5)	−0.0032 (4)	0.0151 (5)	−0.0038 (4)
N3	0.0296 (5)	0.0333 (6)	0.0225 (5)	0.0008 (4)	0.0125 (5)	0.0017 (4)
C1	0.0214 (5)	0.0199 (5)	0.0245 (6)	0.0039 (4)	0.0097 (4)	0.0022 (4)
C2	0.0226 (5)	0.0233 (6)	0.0239 (6)	0.0029 (4)	0.0109 (4)	−0.0020 (4)
C3	0.0155 (5)	0.0282 (6)	0.0222 (6)	−0.0008 (4)	0.0096 (4)	0.0014 (4)
C4	0.0234 (5)	0.0198 (5)	0.0261 (6)	−0.0005 (4)	0.0104 (5)	0.0045 (4)
C5	0.0227 (5)	0.0187 (5)	0.0246 (6)	−0.0018 (4)	0.0100 (5)	−0.0016 (4)
C6	0.0152 (5)	0.0204 (5)	0.0222 (6)	−0.0010 (4)	0.0076 (4)	−0.0001 (4)
C7	0.0152 (5)	0.0212 (5)	0.0219 (6)	−0.0014 (4)	0.0074 (4)	0.0001 (4)
C8	0.0215 (5)	0.0224 (5)	0.0209 (6)	−0.0002 (4)	0.0083 (4)	−0.0014 (4)
C9	0.0270 (6)	0.0333 (6)	0.0254 (6)	0.0025 (5)	0.0151 (5)	0.0041 (5)

O1—C7	1.2180 (13)	C4—C5	1.3765 (17)
N1—N2	1.2350 (14)	C4—H4B	0.9300
N1—C8	1.4659 (15)	C5—C6	1.4003 (16)
N2—N3	1.1327 (14)	C5—H5A	0.9300
C1—C2	1.3806 (16)	C6—C7	1.4821 (16)
C1—C6	1.3968 (16)	C7—C8	1.5247 (15)
C1—H1B	0.9300	C8—H8A	0.9700
C2—C3	1.3970 (16)	C8—H8B	0.9700
C2—H2A	0.9300	C9—H9A	0.9600
C3—C4	1.3991 (16)	C9—H9B	0.9600
C3—C9	1.4984 (17)	C9—H9C	0.9600
N2—N1—C8	116.42 (9)	C1—C6—C7	119.08 (10)
N3—N2—N1	170.84 (11)	C5—C6—C7	122.31 (10)
C2—C1—C6	120.60 (10)	O1—C7—C6	122.33 (10)
C2—C1—H1B	119.7	O1—C7—C8	120.22 (10)
C6—C1—H1B	119.7	C6—C7—C8	117.45 (9)
C1—C2—C3	121.02 (10)	N1—C8—C7	113.13 (9)
C1—C2—H2A	119.5	N1—C8—H8A	109.0
C3—C2—H2A	119.5	C7—C8—H8A	109.0
C2—C3—C4	118.09 (10)	N1—C8—H8B	109.0
C2—C3—C9	121.11 (10)	C7—C8—H8B	109.0
C4—C3—C9	120.79 (10)	H8A—C8—H8B	107.8
C5—C4—C3	121.19 (10)	C3—C9—H9A	109.5
C5—C4—H4B	119.4	C3—C9—H9B	109.5
C3—C4—H4B	119.4	H9A—C9—H9B	109.5
C4—C5—C6	120.49 (10)	C3—C9—H9C	109.5
C4—C5—H5A	119.8	H9A—C9—H9C	109.5
C6—C5—H5A	119.8	H9B—C9—H9C	109.5
C1—C6—C5	118.60 (11)
C6—C1—C2—C3	0.53 (16)	C4—C5—C6—C7	179.79 (9)
C1—C2—C3—C4	0.77 (16)	C1—C6—C7—O1	5.82 (15)
C1—C2—C3—C9	−177.81 (9)	C5—C6—C7—O1	−173.48 (10)
C2—C3—C4—C5	−1.46 (16)	C1—C6—C7—C8	−174.32 (9)
C9—C3—C4—C5	177.13 (10)	C5—C6—C7—C8	6.38 (14)
C3—C4—C5—C6	0.84 (16)	N2—N1—C8—C7	65.13 (12)
C2—C1—C6—C5	−1.16 (15)	O1—C7—C8—N1	−11.81 (14)
C2—C1—C6—C7	179.51 (9)	C6—C7—C8—N1	168.33 (8)
C4—C5—C6—C1	0.48 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O1i	0.97	2.40	3.2404 (19)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1i	0.97	2.40	3.2404 (19)	145

Symmetry code: (i) .