2-(2-Chloro-phen-oxy)acetohydrazide.

In the title compound, C(8)H(9)ClN(2)O(2), the acetohydrazide group is approximately planar, with the maximum deviation of 0.031 (2) Å. In the crystal, the mol-ecules are linked by N-H⋯N, N-H⋯O and C-H⋯O hydrogen bonds, with the acetohydrazide O atom accepting two C-H⋯O links and one N-H⋯O link. This results in infinite sheets lying parallel to (100).

Related literature

For general background to and biological properties of hydrazine derivatives, see: Rando et al. (2008 ▶); Kumar et al. (2009 ▶); Kamal et al. (2007 ▶); Masunari & Tavares (2007 ▶); Rando et al. (2002 ▶). For related structures, see: Fun et al. (2009 ▶, 2010 ▶). For the preparation, see: Holla & Udupa (1992 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C8H9ClN2O2

M = 200.62

Monoclinic,

a = 15.2384 (5) Å

b = 3.9269 (1) Å

c = 16.8843 (6) Å

β = 117.269 (2)°

V = 898.07 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.39 mm−1

T = 100 K

0.28 × 0.10 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan SADABS (Bruker, 2005 ▶) T min = 0.897, T max = 0.965

11351 measured reflections

2662 independent reflections

2029 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.121

S = 1.05

2662 reflections

130 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051356/hb5257sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051356/hb5257Isup2.hkl

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

C8H9ClN2O2	F(000) = 416
Mr = 200.62	Dx = 1.484 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3388 reflections
a = 15.2384 (5) Å	θ = 2.4–30.1°
b = 3.9269 (1) Å	µ = 0.39 mm−1
c = 16.8843 (6) Å	T = 100 K
β = 117.269 (2)°	Block, colourless
V = 898.07 (5) Å3	0.28 × 0.10 × 0.09 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	2662 independent reflections
Radiation source: fine-focus sealed tube	2029 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 30.2°, θmin = 1.5°
Absorption correction: multi-scan SADABS (Bruker, 2005)	h = −21→20
Tmin = 0.897, Tmax = 0.965	k = −5→4
11351 measured reflections	l = −22→23

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.3771P] where P = (Fo2 + 2Fc2)/3
2662 reflections	(Δ/σ)max < 0.001
130 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.69094 (3)	0.22956 (13)	0.86423 (3)	0.02146 (15)
O1	0.83867 (8)	0.0410 (4)	0.81001 (8)	0.0174 (3)
O2	1.09342 (9)	−0.0760 (4)	0.87110 (8)	0.0183 (3)
N1	1.01406 (11)	0.2382 (4)	0.93081 (10)	0.0158 (3)
N2	1.10162 (11)	0.3687 (5)	1.00234 (10)	0.0175 (3)
C1	0.72527 (14)	−0.1775 (5)	0.66271 (12)	0.0192 (4)
H1A	0.7768	−0.2398	0.6506	0.023*
C2	0.62775 (14)	−0.2331 (5)	0.59963 (12)	0.0232 (4)
H2A	0.6144	−0.3314	0.5452	0.028*
C3	0.55039 (14)	−0.1436 (6)	0.61715 (13)	0.0236 (4)
H3A	0.4855	−0.1815	0.5746	0.028*
C4	0.57002 (12)	0.0024 (5)	0.69829 (12)	0.0197 (4)
H4A	0.5185	0.0633	0.7105	0.024*
C5	0.66699 (13)	0.0571 (5)	0.76107 (12)	0.0177 (4)
C6	0.74518 (12)	−0.0283 (5)	0.74390 (11)	0.0161 (4)
C7	0.91785 (12)	−0.0685 (5)	0.79289 (11)	0.0154 (4)
H7A	0.9113	0.0356	0.7383	0.018*
H7B	0.9149	−0.3137	0.7851	0.018*
C8	1.01638 (12)	0.0305 (5)	0.86985 (11)	0.0147 (4)
H1N1	0.9633 (17)	0.307 (5)	0.9322 (14)	0.014 (5)*
H1N2	1.1345 (16)	0.478 (6)	0.9761 (14)	0.018 (6)*
H2N2	1.1333 (17)	0.195 (6)	1.0302 (16)	0.022 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0139 (2)	0.0305 (3)	0.0168 (2)	0.00075 (17)	0.00427 (15)	−0.00393 (19)
O1	0.0092 (5)	0.0272 (8)	0.0117 (6)	−0.0005 (5)	0.0012 (4)	−0.0029 (5)
O2	0.0137 (6)	0.0242 (8)	0.0163 (6)	0.0013 (5)	0.0063 (5)	−0.0006 (5)
N1	0.0092 (6)	0.0219 (8)	0.0123 (7)	0.0002 (6)	0.0016 (5)	−0.0024 (6)
N2	0.0113 (6)	0.0238 (9)	0.0114 (7)	−0.0012 (6)	−0.0002 (6)	−0.0012 (6)
C1	0.0177 (8)	0.0214 (10)	0.0142 (8)	−0.0010 (7)	0.0035 (7)	−0.0001 (7)
C2	0.0226 (9)	0.0242 (10)	0.0136 (8)	−0.0030 (8)	0.0003 (7)	−0.0023 (8)
C3	0.0145 (8)	0.0259 (11)	0.0201 (9)	−0.0035 (7)	−0.0011 (7)	−0.0010 (8)
C4	0.0113 (7)	0.0224 (10)	0.0205 (9)	−0.0013 (7)	0.0029 (7)	0.0006 (8)
C5	0.0154 (8)	0.0184 (10)	0.0140 (8)	−0.0007 (7)	0.0023 (6)	0.0002 (7)
C6	0.0115 (7)	0.0175 (9)	0.0140 (8)	−0.0011 (7)	0.0012 (6)	0.0019 (7)
C7	0.0124 (7)	0.0195 (10)	0.0116 (7)	−0.0005 (7)	0.0031 (6)	−0.0007 (7)
C8	0.0142 (7)	0.0162 (9)	0.0115 (7)	0.0002 (7)	0.0041 (6)	0.0032 (6)

Cl1—C5	1.7443 (19)	C1—H1A	0.9300
O1—C6	1.3756 (19)	C2—C3	1.386 (3)
O1—C7	1.430 (2)	C2—H2A	0.9300
O2—C8	1.237 (2)	C3—C4	1.385 (3)
N1—C8	1.326 (2)	C3—H3A	0.9300
N1—N2	1.4231 (19)	C4—C5	1.385 (2)
N1—H1N1	0.83 (2)	C4—H4A	0.9300
N2—H1N2	0.91 (2)	C5—C6	1.390 (3)
N2—H2N2	0.84 (2)	C7—C8	1.519 (2)
C1—C6	1.391 (3)	C7—H7A	0.9700
C1—C2	1.393 (2)	C7—H7B	0.9700
C6—O1—C7	115.63 (14)	C5—C4—H4A	120.3
C8—N1—N2	122.15 (15)	C3—C4—H4A	120.3
C8—N1—H1N1	125.4 (15)	C4—C5—C6	121.25 (17)
N2—N1—H1N1	112.5 (15)	C4—C5—Cl1	119.09 (15)
N1—N2—H1N2	105.5 (13)	C6—C5—Cl1	119.65 (13)
N1—N2—H2N2	104.8 (16)	O1—C6—C5	116.80 (16)
H1N2—N2—H2N2	110 (2)	O1—C6—C1	124.09 (17)
C6—C1—C2	119.63 (18)	C5—C6—C1	119.11 (16)
C6—C1—H1A	120.2	O1—C7—C8	110.19 (14)
C2—C1—H1A	120.2	O1—C7—H7A	109.6
C3—C2—C1	120.73 (18)	C8—C7—H7A	109.6
C3—C2—H2A	119.6	O1—C7—H7B	109.6
C1—C2—H2A	119.6	C8—C7—H7B	109.6
C4—C3—C2	119.78 (17)	H7A—C7—H7B	108.1
C4—C3—H3A	120.1	O2—C8—N1	123.86 (16)
C2—C3—H3A	120.1	O2—C8—C7	119.11 (16)
C5—C4—C3	119.50 (18)	N1—C8—C7	117.00 (15)
C6—C1—C2—C3	−0.5 (3)	C4—C5—C6—C1	−1.3 (3)
C1—C2—C3—C4	−0.1 (3)	Cl1—C5—C6—C1	177.58 (15)
C2—C3—C4—C5	0.0 (3)	C2—C1—C6—O1	−179.16 (18)
C3—C4—C5—C6	0.7 (3)	C2—C1—C6—C5	1.1 (3)
C3—C4—C5—Cl1	−178.13 (16)	C6—O1—C7—C8	178.73 (15)
C7—O1—C6—C5	176.26 (16)	N2—N1—C8—O2	2.4 (3)
C7—O1—C6—C1	−3.5 (3)	N2—N1—C8—C7	−175.28 (16)
C4—C5—C6—O1	179.00 (18)	O1—C7—C8—O2	172.20 (16)
Cl1—C5—C6—O1	−2.1 (2)	O1—C7—C8—N1	−10.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2i	0.83 (3)	2.20 (2)	2.930 (3)	148 (2)
N2—H1N2···O2ii	0.91 (3)	2.36 (2)	3.070 (2)	134 (2)
C1—H1A···O2iii	0.93	2.54	3.443 (3)	164
C7—H7A···O2iv	0.97	2.37	3.317 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2i	0.83 (3)	2.20 (2)	2.930 (3)	148 (2)
N2—H1N2⋯O2ii	0.91 (3)	2.36 (2)	3.070 (2)	134 (2)
C1—H1A⋯O2iii	0.93	2.54	3.443 (3)	164
C7—H7A⋯O2iv	0.97	2.37	3.317 (2)	165

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