2-(4-Bromo-phen-oxy)propanohydrazide.

The title compound, C(9)H(11)BrN(2)O(2), is an important inter-mediate for the synthesis of heterocyclic compounds such as azoles, 2,5-disubstituted-1,3,4-oxadiazo-les and 5-substituted 2-mercapto-1,3,4-oxadiazo-les. The bromo-phen-oxy group subtends a dihedral angle of 82.81 (7)° with the plane passing through the propanohydrazide moiety. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds that form columns extending along the b axis.

Related literature

For carboxy­hydrazide derivatives with biological activities, see: Belkadi & Othman (2006 ▶); Goswami et al. (1984 ▶); Akhtar et al. (2008 ▶); Akhtar, Hameed et al. (2007 ▶); Ahmad et al. (1996 ▶); Akhtar et al. (2006 ▶); For related structures, see: Akhtar, Khawar Rauf et al. (2007 ▶); Zheng (2008 ▶).

Experimental

Crystal data

C9H11BrN2O2

M = 259.11

Monoclinic,

a = 10.2598 (14) Å

b = 4.8009 (7) Å

c = 23.322 (3) Å

β = 112.712 (6)°

V = 1059.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.86 mm−1

T = 113 (2) K

0.50 × 0.30 × 0.20 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer

Absorption correction: integration (NUMABS; Higashi, 1999) T min = 0.531, T max = 0.759

8296 measured reflections

2418 independent reflections

2201 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.076

S = 1.20

2418 reflections

137 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.59 e Å−3

Δρmin = −0.75 e Å−3

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and TEXSAN.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003134/si2151sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003134/si2151Isup2.hkl

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

C9H11BrN2O2	F(000) = 520
Mr = 259.11	Dx = 1.624 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 2804 reflections
a = 10.2598 (14) Å	θ = 3.4–27.5°
b = 4.8009 (7) Å	µ = 3.86 mm−1
c = 23.322 (3) Å	T = 113 K
β = 112.712 (6)°	Block, colorless
V = 1059.7 (3) Å3	0.50 × 0.30 × 0.20 mm
Z = 4

Rigaku/MSC Mercury CCD diffractometer	2201 reflections with I > 2σ(I)
Detector resolution: 14.62 pixels mm-1	Rint = 0.039
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: integration (NUMABS; Higashi, 1999)	h = −13→11
Tmin = 0.531, Tmax = 0.759	k = −6→4
8296 measured reflections	l = −26→30
2418 independent reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.20	w = 1/[σ2(Fo2) + (0.0037P)2 + 1.6325P] where P = (Fo2 + 2Fc2)/3
2418 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.59 e Å−3
0 restraints	Δρmin = −0.75 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 > 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
C1	0.4780 (3)	0.1909 (5)	0.40801 (12)	0.0143 (5)
O1	0.4868 (2)	−0.0616 (4)	0.41874 (9)	0.0203 (4)
N1	0.5635 (2)	0.3771 (4)	0.44658 (11)	0.0162 (5)
H1	0.551 (3)	0.551 (6)	0.4399 (14)	0.019*
N2	0.6750 (3)	0.3047 (5)	0.50307 (11)	0.0200 (5)
H2A	0.643 (3)	0.205 (7)	0.5240 (15)	0.024*
H2B	0.740 (3)	0.209 (6)	0.4928 (14)	0.024*
C2	0.3698 (3)	0.3120 (6)	0.34780 (13)	0.0188 (6)
H2	0.3260	0.4839	0.3568	0.023*
O2	0.2635 (2)	0.1095 (4)	0.31761 (9)	0.0199 (4)
C3	0.1643 (3)	0.0534 (5)	0.34207 (13)	0.0164 (5)
C4	0.0672 (3)	−0.1518 (6)	0.31070 (12)	0.0180 (5)
H4	0.0761	−0.2460	0.2766	0.022*
C5	−0.0425 (3)	−0.2199 (6)	0.32900 (13)	0.0205 (6)
H5	−0.1092	−0.3595	0.3076	0.025*
C6	−0.0528 (3)	−0.0808 (6)	0.37882 (14)	0.0222 (6)
C7	0.0439 (3)	0.1215 (6)	0.41093 (14)	0.0218 (6)
H7	0.0353	0.2140	0.4453	0.026*
C8	0.1534 (3)	0.1881 (6)	0.39257 (13)	0.0190 (6)
H8	0.2208	0.3256	0.4145	0.023*
Br1	−0.20430 (4)	−0.16915 (9)	0.403569 (18)	0.04154 (13)
C9	0.4395 (4)	0.3772 (7)	0.30247 (15)	0.0332 (8)
H9A	0.4827	0.2076	0.2943	0.050*
H9B	0.5125	0.5194	0.3204	0.050*
H9C	0.3682	0.4466	0.2634	0.050*

	U11	U22	U33	U12	U13	U23
C1	0.0158 (13)	0.0134 (12)	0.0163 (13)	−0.0004 (10)	0.0090 (11)	0.0010 (10)
O1	0.0227 (11)	0.0116 (9)	0.0254 (11)	−0.0004 (8)	0.0079 (9)	0.0015 (8)
N1	0.0194 (12)	0.0079 (10)	0.0167 (12)	0.0010 (9)	0.0020 (10)	0.0014 (9)
N2	0.0196 (12)	0.0209 (12)	0.0168 (12)	0.0003 (10)	0.0041 (10)	0.0026 (10)
C2	0.0176 (13)	0.0184 (13)	0.0176 (14)	−0.0041 (11)	0.0035 (11)	0.0023 (11)
O2	0.0209 (10)	0.0220 (10)	0.0152 (10)	−0.0090 (8)	0.0053 (8)	−0.0031 (8)
C3	0.0145 (13)	0.0166 (13)	0.0146 (13)	0.0008 (10)	0.0017 (11)	0.0041 (10)
C4	0.0186 (13)	0.0177 (13)	0.0140 (13)	0.0000 (11)	0.0023 (11)	−0.0006 (11)
C5	0.0178 (14)	0.0194 (14)	0.0194 (15)	−0.0039 (11)	0.0018 (11)	0.0008 (11)
C6	0.0165 (14)	0.0272 (15)	0.0218 (15)	0.0005 (11)	0.0062 (12)	0.0047 (12)
C7	0.0212 (15)	0.0216 (15)	0.0200 (15)	0.0031 (11)	0.0049 (12)	−0.0021 (11)
C8	0.0159 (13)	0.0182 (13)	0.0176 (14)	−0.0010 (11)	0.0006 (11)	−0.0019 (11)
Br1	0.02723 (18)	0.0649 (3)	0.0383 (2)	−0.01613 (17)	0.01901 (15)	−0.01174 (19)
C9	0.0321 (18)	0.043 (2)	0.0216 (16)	−0.0163 (15)	0.0075 (14)	0.0044 (14)

C1—O1	1.234 (3)	C4—C5	1.389 (4)
C1—N1	1.330 (3)	C4—H4	0.9500
C1—C2	1.529 (4)	C5—C6	1.379 (4)
N1—N2	1.415 (3)	C5—H5	0.9500
N1—H1	0.85 (3)	C6—C7	1.384 (4)
N2—H2A	0.83 (3)	C6—Br1	1.903 (3)
N2—H2B	0.92 (3)	C7—C8	1.385 (4)
C2—O2	1.427 (3)	C7—H7	0.9500
C2—C9	1.520 (4)	C8—H8	0.9500
C2—H2	1.0000	C9—H9A	0.9800
O2—C3	1.372 (3)	C9—H9B	0.9800
C3—C8	1.385 (4)	C9—H9C	0.9800
C3—C4	1.392 (4)
O1—C1—N1	123.1 (2)	C5—C4—H4	119.8
O1—C1—C2	122.0 (2)	C3—C4—H4	119.8
N1—C1—C2	114.9 (2)	C6—C5—C4	118.7 (3)
C1—N1—N2	123.4 (2)	C6—C5—H5	120.7
C1—N1—H1	121 (2)	C4—C5—H5	120.7
N2—N1—H1	115 (2)	C5—C6—C7	121.6 (3)
N1—N2—H2A	109 (2)	C5—C6—Br1	119.0 (2)
N1—N2—H2B	107 (2)	C7—C6—Br1	119.4 (2)
H2A—N2—H2B	111 (3)	C6—C7—C8	119.5 (3)
O2—C2—C9	105.8 (2)	C6—C7—H7	120.3
O2—C2—C1	109.9 (2)	C8—C7—H7	120.3
C9—C2—C1	110.3 (2)	C3—C8—C7	119.8 (3)
O2—C2—H2	110.3	C3—C8—H8	120.1
C9—C2—H2	110.3	C7—C8—H8	120.1
C1—C2—H2	110.3	C2—C9—H9A	109.5
C3—O2—C2	118.5 (2)	C2—C9—H9B	109.5
O2—C3—C8	125.4 (2)	H9A—C9—H9B	109.5
O2—C3—C4	114.6 (2)	C2—C9—H9C	109.5
C8—C3—C4	120.1 (3)	H9A—C9—H9C	109.5
C5—C4—C3	120.4 (3)	H9B—C9—H9C	109.5
O1—C1—N1—N2	1.5 (4)	O2—C3—C4—C5	−177.1 (2)
C2—C1—N1—N2	−176.7 (2)	C8—C3—C4—C5	1.1 (4)
O1—C1—C2—O2	15.9 (4)	C3—C4—C5—C6	−0.2 (4)
N1—C1—C2—O2	−165.9 (2)	C4—C5—C6—C7	−0.6 (4)
O1—C1—C2—C9	−100.3 (3)	C4—C5—C6—Br1	179.2 (2)
N1—C1—C2—C9	77.9 (3)	C5—C6—C7—C8	0.4 (4)
C9—C2—O2—C3	−166.8 (2)	Br1—C6—C7—C8	−179.3 (2)
C1—C2—O2—C3	74.1 (3)	O2—C3—C8—C7	176.8 (2)
C2—O2—C3—C8	3.5 (4)	C4—C3—C8—C7	−1.3 (4)
C2—O2—C3—C4	−178.3 (2)	C6—C7—C8—C3	0.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.85 (3)	1.97 (3)	2.812 (3)	170 (3)
N2—H2A···O1ii	0.83 (3)	2.33 (3)	3.127 (3)	161 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.85 (3)	1.97 (3)	2.812 (3)	170 (3)
N2—H2A⋯O1ii	0.83 (3)	2.33 (3)	3.127 (3)	161 (3)

Symmetry codes: (i) ; (ii) .