2-(4-Bromo-phen-yl)acetohydrazide.

In the title compound, C(8)H(9)BrN(2)O, the 1-bromo-4-methyl-benzene group and the formic hydrazide moiety [r.m.s. deviations of 0.0129 and 0.0038 Å] are oriented at a dihedral angle of 80.66 (11)°. In the crystal, mol-ecules are linked via strong N-H⋯O hydrogen bonds, leading to the formation of chains in the [010] direction. These chains are linked via weaker N-H⋯N and N-H⋯O hydrogen bonds, with R(2) (2)(7) and R(3) (2)(7) ring motifs, forming a two-dimensional network parallel to (001).

Related literature

For background literature and the crystal structure of 2-chloro­benzohydrazide, see: Ahmad et al. (2012 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H9BrN2O

M = 229.07

Monoclinic,

a = 6.0798 (2) Å

b = 4.8565 (1) Å

c = 15.1126 (5) Å

β = 98.003 (2)°

V = 441.88 (2) Å3

Z = 2

Mo Kα radiation

μ = 4.60 mm−1

T = 296 K

0.36 × 0.23 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.298, T max = 0.366

4331 measured reflections

1814 independent reflections

1677 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.059

S = 1.06

1814 reflections

115 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 583 Friedel pairs

Flack parameter: 0.007 (11)

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027006/su2429sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027006/su2429Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027006/su2429Isup3.cml

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

C8H9BrN2O	F(000) = 228
Mr = 229.07	Dx = 1.722 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1677 reflections
a = 6.0798 (2) Å	θ = 2.7–28.3°
b = 4.8565 (1) Å	µ = 4.60 mm−1
c = 15.1126 (5) Å	T = 296 K
β = 98.003 (2)°	Rod, colourless
V = 441.88 (2) Å3	0.36 × 0.23 × 0.22 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	1814 independent reflections
Radiation source: fine-focus sealed tube	1677 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 7.50 pixels mm-1	θmax = 28.3°, θmin = 2.7°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −6→4
Tmin = 0.298, Tmax = 0.366	l = −20→20
4331 measured 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)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.024P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1814 reflections	Δρmax = 0.44 e Å−3
115 parameters	Δρmin = −0.47 e Å−3
1 restraint	Absolute structure: Flack (1983), 583 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.007 (11)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Br1	0.42290 (4)	0.23371 (7)	0.07962 (1)	0.0435 (1)
O1	−0.1520 (3)	0.7065 (5)	0.38909 (13)	0.0457 (6)
N1	−0.2370 (4)	1.1385 (4)	0.42196 (15)	0.0364 (7)
N2	−0.3296 (5)	1.0741 (6)	0.49999 (17)	0.0420 (8)
C1	0.2739 (4)	0.4860 (5)	0.14603 (16)	0.0315 (8)
C2	0.0587 (5)	0.5632 (6)	0.11262 (19)	0.0395 (9)
C3	−0.0499 (4)	0.7519 (8)	0.16041 (16)	0.0407 (8)
C4	0.0518 (5)	0.8638 (5)	0.23979 (17)	0.0362 (8)
C5	0.2669 (5)	0.7798 (7)	0.27159 (17)	0.0416 (12)
C6	0.3788 (5)	0.5900 (6)	0.22578 (17)	0.0381 (8)
C7	−0.0693 (6)	1.0694 (6)	0.2896 (2)	0.0494 (10)
C8	−0.1528 (4)	0.9529 (5)	0.37211 (16)	0.0289 (7)
H1	−0.23523	1.30826	0.40587	0.0437*
H2	−0.01156	0.49007	0.05918	0.0474*
H2A	−0.416 (5)	0.940 (8)	0.491 (2)	0.0503*
H2B	−0.230 (6)	1.040 (8)	0.531 (2)	0.0503*
H3	−0.19442	0.80410	0.13848	0.0488*
H5	0.33752	0.85271	0.32499	0.0500*
H6	0.52191	0.53407	0.24842	0.0457*
H7A	−0.19487	1.14063	0.24952	0.0591*
H7B	0.02941	1.22250	0.30749	0.0591*

	U11	U22	U33	U12	U13	U23
Br1	0.0503 (2)	0.0403 (2)	0.0433 (1)	0.0101 (2)	0.0184 (1)	−0.0001 (2)
O1	0.0663 (11)	0.0214 (11)	0.0547 (10)	0.0035 (12)	0.0269 (9)	0.0049 (11)
N1	0.0533 (14)	0.0226 (11)	0.0367 (11)	0.0007 (9)	0.0184 (10)	0.0019 (8)
N2	0.0511 (16)	0.0378 (14)	0.0407 (14)	0.0000 (12)	0.0193 (12)	−0.0020 (11)
C1	0.0367 (13)	0.0284 (14)	0.0315 (12)	0.0012 (10)	0.0123 (10)	0.0007 (10)
C2	0.0393 (14)	0.0426 (17)	0.0356 (13)	0.0034 (12)	0.0021 (12)	−0.0016 (12)
C3	0.0373 (11)	0.0407 (16)	0.0442 (12)	0.0084 (16)	0.0063 (10)	0.0062 (17)
C4	0.0523 (16)	0.0247 (13)	0.0352 (13)	0.0029 (11)	0.0185 (12)	0.0034 (10)
C5	0.0488 (14)	0.044 (3)	0.0321 (11)	−0.0038 (14)	0.0061 (11)	−0.0051 (12)
C6	0.0344 (14)	0.0440 (16)	0.0355 (13)	0.0028 (12)	0.0040 (12)	0.0009 (12)
C7	0.077 (2)	0.0298 (16)	0.0479 (17)	0.0083 (15)	0.0319 (16)	0.0057 (13)
C8	0.0312 (12)	0.0221 (13)	0.0338 (12)	0.0001 (10)	0.0064 (10)	−0.0008 (9)

Br1—C1	1.893 (2)	C4—C5	1.390 (4)
O1—C8	1.224 (3)	C4—C7	1.503 (4)
N1—N2	1.411 (4)	C5—C6	1.387 (4)
N1—C8	1.323 (3)	C7—C8	1.520 (4)
N1—H1	0.8600	C2—H2	0.9300
N2—H2B	0.73 (3)	C3—H3	0.9300
N2—H2A	0.84 (4)	C5—H5	0.9300
C1—C2	1.387 (4)	C6—H6	0.9300
C1—C6	1.379 (4)	C7—H7A	0.9700
C2—C3	1.389 (4)	C7—H7B	0.9700
C3—C4	1.382 (4)
N2—N1—C8	123.8 (2)	O1—C8—C7	123.0 (2)
C8—N1—H1	118.00	N1—C8—C7	114.4 (2)
N2—N1—H1	118.00	O1—C8—N1	122.5 (2)
N1—N2—H2B	101 (3)	C1—C2—H2	121.00
H2A—N2—H2B	112 (4)	C3—C2—H2	121.00
N1—N2—H2A	111 (2)	C2—C3—H3	119.00
Br1—C1—C2	118.61 (19)	C4—C3—H3	119.00
Br1—C1—C6	120.2 (2)	C4—C5—H5	119.00
C2—C1—C6	121.2 (2)	C6—C5—H5	119.00
C1—C2—C3	118.8 (2)	C1—C6—H6	121.00
C2—C3—C4	121.5 (3)	C5—C6—H6	121.00
C3—C4—C7	120.3 (3)	C4—C7—H7A	109.00
C3—C4—C5	118.1 (3)	C4—C7—H7B	109.00
C5—C4—C7	121.6 (3)	C8—C7—H7A	109.00
C4—C5—C6	121.7 (3)	C8—C7—H7B	109.00
C1—C6—C5	118.7 (3)	H7A—C7—H7B	108.00
C4—C7—C8	114.0 (2)
N2—N1—C8—O1	1.3 (4)	C2—C3—C4—C7	179.5 (3)
N2—N1—C8—C7	178.1 (3)	C3—C4—C5—C6	0.1 (4)
Br1—C1—C2—C3	−178.9 (2)	C7—C4—C5—C6	179.9 (3)
C6—C1—C2—C3	1.0 (4)	C3—C4—C7—C8	104.7 (3)
Br1—C1—C6—C5	178.4 (2)	C5—C4—C7—C8	−75.1 (4)
C2—C1—C6—C5	−1.5 (4)	C4—C5—C6—C1	1.0 (4)
C1—C2—C3—C4	0.2 (5)	C4—C7—C8—O1	−10.6 (4)
C2—C3—C4—C5	−0.7 (4)	C4—C7—C8—N1	172.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.02	2.863 (3)	165
N2—H2A···N2ii	0.84 (4)	2.37 (4)	3.192 (4)	167 (3)
N2—H2B···O1iii	0.73 (3)	2.59 (4)	3.230 (3)	147 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.02	2.863 (3)	165
N2—H2A⋯N2ii	0.84 (4)	2.37 (4)	3.192 (4)	167 (3)
N2—H2B⋯O1iii	0.73 (3)	2.59 (4)	3.230 (3)	147 (4)

Symmetry codes: (i) ; (ii) ; (iii) .