1-(Benzotriazol-1-yl)-2-bromoethanone.

In the title compound C(8)H(6)BrN(3)O, the benzotriazole ring is essentially planar (r.m.s. deviation = 0.0034 Å) and the bromo-acetyl unit is twisted at a dihedral angle of 15.24 (16)° with respect to it. In the crystal, pairs of C-H⋯O hydrogen bondings result in the formation of inversion dimers, forming R(2) (2)(12) rings, which are connected by further C-H⋯O inter-actions into chains extending along the b-axis direction.

Related literature

For the biological activity of the title compound, see: Nakagawa et al. (1973 ▶). For the crystal structure of a closely related compound, see: Selvarathy Grace et al. (2012 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H6BrN3O

M = 240.07

Monoclinic,

a = 12.4815 (4) Å

b = 4.7207 (1) Å

c = 15.4780 (5) Å

β = 103.468 (3)°

V = 886.91 (4) Å3

Z = 4

Cu Kα radiation

μ = 6.02 mm−1

T = 296 K

0.28 × 0.11 × 0.05 mm

Data collection

Agilent SuperNova Dual (Cu at zero) Atlas, CCD diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.284, T max = 0.753

4362 measured reflections

1833 independent reflections

1507 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.141

S = 1.07

1833 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.51 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and X-SEED (Barbour, 2001 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812042900/pv2595sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812042900/pv2595Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812042900/pv2595Isup3.cml

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

C8H6BrN3O	F(000) = 472
Mr = 240.07	Dx = 1.798 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 2295 reflections
a = 12.4815 (4) Å	θ = 3.6–76.0°
b = 4.7207 (1) Å	µ = 6.02 mm−1
c = 15.4780 (5) Å	T = 296 K
β = 103.468 (3)°	Plate, colorless
V = 886.91 (4) Å3	0.28 × 0.11 × 0.05 mm
Z = 4

Agilent SuperNova Dual (Cu at zero) Atlas, CCD diffractometer	1833 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1507 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
ω scans	θmax = 76.2°, θmin = 4.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −15→12
Tmin = 0.284, Tmax = 0.753	k = −5→5
4362 measured reflections	l = −19→19

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0838P)2 + 0.0945P] where P = (Fo2 + 2Fc2)/3
1833 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.84802 (3)	0.99732 (9)	−0.01180 (3)	0.0947 (2)
O1	0.63342 (16)	0.7775 (4)	0.02369 (12)	0.0717 (5)
N1	0.62518 (17)	1.0238 (4)	0.14622 (14)	0.0512 (5)
N2	0.67298 (17)	1.2209 (5)	0.20998 (14)	0.0603 (5)
N3	0.61989 (19)	1.2185 (5)	0.27134 (14)	0.0673 (6)
C1	0.5348 (2)	1.0227 (5)	0.25097 (18)	0.0582 (6)
C2	0.4553 (3)	0.9458 (7)	0.2965 (2)	0.0774 (8)
H2	0.4528	1.0294	0.3504	0.093*
C3	0.3809 (2)	0.7419 (8)	0.2586 (2)	0.0800 (9)
H3	0.3269	0.6862	0.2875	0.096*
C4	0.3843 (2)	0.6154 (7)	0.1776 (2)	0.0743 (7)
H4	0.3320	0.4787	0.1540	0.089*
C5	0.4624 (2)	0.6864 (5)	0.13167 (17)	0.0608 (6)
H5	0.4647	0.6012	0.0780	0.073*
C6	0.53792 (18)	0.8945 (5)	0.17058 (14)	0.0509 (5)
C7	0.6721 (2)	0.9628 (5)	0.07435 (16)	0.0518 (5)
C8	0.7682 (2)	1.1462 (6)	0.06834 (17)	0.0614 (6)
H8A	0.8172	1.1633	0.1268	0.074*
H8B	0.7419	1.3343	0.0489	0.074*

	U11	U22	U33	U12	U13	U23
Br1	0.0844 (3)	0.1209 (5)	0.0895 (4)	0.00843 (18)	0.0419 (2)	−0.00526 (18)
O1	0.0855 (12)	0.0685 (12)	0.0622 (10)	−0.0108 (9)	0.0193 (9)	−0.0213 (9)
N1	0.0541 (10)	0.0483 (10)	0.0484 (10)	0.0024 (7)	0.0065 (8)	−0.0066 (7)
N2	0.0655 (11)	0.0525 (11)	0.0594 (11)	0.0003 (9)	0.0075 (9)	−0.0128 (9)
N3	0.0805 (13)	0.0640 (13)	0.0562 (11)	0.0053 (11)	0.0136 (10)	−0.0146 (9)
C1	0.0637 (14)	0.0573 (14)	0.0522 (13)	0.0132 (10)	0.0110 (11)	−0.0013 (9)
C2	0.087 (2)	0.0816 (19)	0.0684 (18)	0.0213 (16)	0.0281 (15)	0.0064 (14)
C3	0.0694 (15)	0.087 (2)	0.088 (2)	0.0074 (15)	0.0282 (15)	0.0204 (17)
C4	0.0606 (14)	0.0732 (18)	0.0864 (19)	−0.0028 (13)	0.0115 (13)	0.0139 (16)
C5	0.0592 (12)	0.0586 (14)	0.0600 (13)	−0.0012 (11)	0.0045 (10)	0.0011 (11)
C6	0.0535 (11)	0.0480 (11)	0.0486 (11)	0.0085 (9)	0.0066 (8)	0.0032 (9)
C7	0.0564 (12)	0.0495 (12)	0.0477 (12)	0.0042 (9)	0.0080 (9)	−0.0026 (8)
C8	0.0640 (13)	0.0619 (15)	0.0586 (13)	0.0006 (11)	0.0150 (10)	−0.0016 (11)

Br1—C8	1.897 (3)	C2—H2	0.9300
O1—C7	1.199 (3)	C3—C4	1.398 (5)
N1—C6	1.376 (3)	C3—H3	0.9300
N1—N2	1.386 (3)	C4—C5	1.374 (4)
N1—C7	1.402 (3)	C4—H4	0.9300
N2—N3	1.279 (3)	C5—C6	1.397 (3)
N3—C1	1.388 (4)	C5—H5	0.9300
C1—C2	1.391 (5)	C7—C8	1.500 (4)
C1—C6	1.392 (3)	C8—H8A	0.9700
C2—C3	1.371 (5)	C8—H8B	0.9700
C6—N1—N2	109.9 (2)	C3—C4—H4	118.9
C6—N1—C7	129.1 (2)	C4—C5—C6	115.9 (3)
N2—N1—C7	120.8 (2)	C4—C5—H5	122.0
N3—N2—N1	108.2 (2)	C6—C5—H5	122.0
N2—N3—C1	109.8 (2)	N1—C6—C1	104.0 (2)
N3—C1—C2	131.0 (3)	N1—C6—C5	133.8 (2)
N3—C1—C6	108.2 (2)	C1—C6—C5	122.3 (2)
C2—C1—C6	120.7 (3)	O1—C7—N1	119.3 (2)
C3—C2—C1	117.3 (3)	O1—C7—C8	125.9 (2)
C3—C2—H2	121.4	N1—C7—C8	114.8 (2)
C1—C2—H2	121.4	C7—C8—Br1	112.09 (18)
C2—C3—C4	121.6 (3)	C7—C8—H8A	109.2
C2—C3—H3	119.2	Br1—C8—H8A	109.2
C4—C3—H3	119.2	C7—C8—H8B	109.2
C5—C4—C3	122.2 (3)	Br1—C8—H8B	109.2
C5—C4—H4	118.9	H8A—C8—H8B	107.9
C6—N1—N2—N3	0.0 (3)	C7—N1—C6—C5	−6.4 (4)
C7—N1—N2—N3	−174.6 (2)	N3—C1—C6—N1	−0.6 (3)
N1—N2—N3—C1	−0.4 (3)	C2—C1—C6—N1	179.7 (2)
N2—N3—C1—C2	−179.7 (3)	N3—C1—C6—C5	−179.9 (2)
N2—N3—C1—C6	0.6 (3)	C2—C1—C6—C5	0.4 (4)
N3—C1—C2—C3	180.0 (3)	C4—C5—C6—N1	−179.1 (2)
C6—C1—C2—C3	−0.4 (4)	C4—C5—C6—C1	0.0 (3)
C1—C2—C3—C4	0.0 (5)	C6—N1—C7—O1	1.4 (4)
C2—C3—C4—C5	0.4 (5)	N2—N1—C7—O1	174.8 (2)
C3—C4—C5—C6	−0.4 (4)	C6—N1—C7—C8	−179.3 (2)
N2—N1—C6—C1	0.4 (2)	N2—N1—C7—C8	−5.9 (3)
C7—N1—C6—C1	174.4 (2)	O1—C7—C8—Br1	−14.7 (3)
N2—N1—C6—C5	179.6 (2)	N1—C7—C8—Br1	166.13 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.93	2.50	3.266 (3)	139
C8—H8B···O1ii	0.97	2.47	3.413 (4)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.50	3.266 (3)	139
C8—H8B⋯O1ii	0.97	2.47	3.413 (4)	163

Symmetry codes: (i) ; (ii) .