2-(4-Meth-oxy-phen-oxy)acetohydrazide.

The title compound, C(9)H(12)N(2)O(3), was synthesized by the reaction of ethyl 2-(4-meth-oxy-phen-oxy)acetate with hydrazine hydrate in ethanol. In the acetohydrazide group, the N-N bond is relatively short [1.413 (2) Å], suggesting some degree of electronic delocalization in the mol-ecule. In the crystal, mol-ecules are linked into sheets lying parallel to the ab plane by N-H⋯N and N-H⋯O hydrogen bonds.

Related literature

For general background to and the biological activity of hydrazides, see: Khattab (2005 ▶); Ozdemir et al. (2009 ▶); Ashiq et al. (2009 ▶); Zhang & Shi (2009 ▶). For related structures, see: Dutkiewicz et al. (2009 ▶); Fun et al. (2009 ▶, 2010a ▶,b ▶, 2011 ▶).

Experimental

Crystal data

C9H12N2O3

M = 196.21

Orthorhombic,

a = 4.0964 (17) Å

b = 6.382 (3) Å

c = 35.608 (14) Å

V = 930.9 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.30 × 0.25 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.969, T max = 0.981

4782 measured reflections

1631 independent reflections

1503 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.089

S = 0.88

1631 reflections

140 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.09 e Å−3

Δρmin = −0.15 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681202435X/rk2352sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202435X/rk2352Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681202435X/rk2352Isup3.cml

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

C9H12N2O3	F(000) = 416
Mr = 196.21	Dx = 1.400 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2044 reflections
a = 4.0964 (17) Å	θ = 2.3–25.2°
b = 6.382 (3) Å	µ = 0.11 mm−1
c = 35.608 (14) Å	T = 298 K
V = 930.9 (7) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.18 mm

Bruker SMART APEXII CCD diffractometer	1631 independent reflections
Radiation source: fine-focus sealed tube	1503 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.1°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −4→4
Tmin = 0.969, Tmax = 0.981	k = −7→7
4782 measured reflections	l = −42→37

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	w = 1/[σ2(Fo2) + (0.070P)2 + 0.087P] where P = (Fo2 + 2Fc2)/3
1631 reflections	(Δ/σ)max < 0.001
140 parameters	Δρmax = 0.09 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.7470 (4)	0.5028 (2)	0.28285 (3)	0.0575 (4)
O3	−0.2287 (3)	1.24787 (16)	0.45169 (3)	0.0492 (3)
O2	0.2900 (3)	0.86238 (18)	0.41321 (3)	0.0475 (3)
N1	−0.0331 (4)	0.9456 (2)	0.47495 (3)	0.0375 (3)
N2	−0.2052 (4)	0.9626 (2)	0.50921 (4)	0.0409 (4)
C1	0.9213 (6)	0.3121 (3)	0.28446 (6)	0.0622 (6)
H1A	1.1128	0.3301	0.2997	0.093*
H1B	0.9844	0.2712	0.2596	0.093*
H1C	0.7852	0.2055	0.2953	0.093*
C3	0.4850 (5)	0.7769 (3)	0.31370 (4)	0.0445 (4)
H3	0.4583	0.8404	0.2904	0.053*
C7	0.6851 (5)	0.4962 (3)	0.35087 (5)	0.0456 (4)
H7	0.7943	0.3690	0.3529	0.055*
C2	0.6424 (4)	0.5884 (3)	0.31602 (4)	0.0418 (4)
C6	0.5651 (4)	0.5936 (3)	0.38255 (4)	0.0434 (4)
H6	0.5952	0.5317	0.4059	0.052*
C9	−0.0652 (4)	1.0868 (2)	0.44833 (4)	0.0354 (4)
C5	0.4022 (4)	0.7803 (2)	0.38004 (4)	0.0373 (4)
C8	0.0994 (4)	1.0462 (2)	0.41147 (4)	0.0394 (4)
H8A	−0.0641	1.0315	0.3919	0.047*
H8B	0.2376	1.1643	0.4051	0.047*
C4	0.3656 (4)	0.8742 (3)	0.34537 (4)	0.0432 (4)
H4	0.2604	1.0029	0.3434	0.052*
H1	0.085 (6)	0.833 (3)	0.4716 (6)	0.060 (6)*
H2B	−0.073 (6)	1.041 (3)	0.5243 (5)	0.063 (6)*
H2A	−0.384 (6)	1.036 (3)	0.5048 (5)	0.059 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0747 (9)	0.0574 (7)	0.0404 (7)	0.0081 (7)	0.0097 (7)	−0.0019 (5)
O3	0.0573 (8)	0.0379 (6)	0.0523 (7)	0.0129 (6)	0.0001 (6)	0.0029 (5)
O2	0.0616 (8)	0.0476 (7)	0.0333 (6)	0.0157 (7)	0.0007 (6)	0.0033 (5)
N1	0.0445 (8)	0.0316 (7)	0.0364 (7)	0.0048 (6)	−0.0010 (6)	0.0002 (5)
N2	0.0459 (9)	0.0384 (8)	0.0385 (7)	−0.0022 (7)	0.0027 (7)	−0.0012 (6)
C1	0.0675 (14)	0.0622 (12)	0.0570 (12)	0.0038 (11)	0.0112 (11)	−0.0109 (9)
C3	0.0533 (11)	0.0464 (9)	0.0339 (8)	−0.0017 (9)	−0.0018 (8)	0.0082 (7)
C7	0.0549 (11)	0.0383 (8)	0.0437 (9)	0.0064 (8)	0.0028 (8)	0.0054 (7)
C2	0.0445 (10)	0.0438 (9)	0.0369 (9)	−0.0057 (8)	0.0030 (7)	−0.0010 (7)
C6	0.0536 (10)	0.0429 (9)	0.0337 (8)	0.0032 (9)	−0.0010 (7)	0.0079 (7)
C9	0.0363 (8)	0.0298 (7)	0.0401 (8)	−0.0019 (7)	−0.0087 (7)	−0.0011 (7)
C5	0.0396 (9)	0.0370 (8)	0.0354 (8)	−0.0015 (7)	−0.0014 (7)	0.0010 (6)
C8	0.0430 (9)	0.0361 (8)	0.0390 (8)	0.0026 (7)	−0.0032 (7)	0.0037 (7)
C4	0.0495 (10)	0.0386 (8)	0.0416 (9)	0.0032 (8)	−0.0021 (7)	0.0069 (7)

O1—C2	1.3701 (19)	C3—C2	1.367 (2)
O1—C1	1.412 (2)	C3—C4	1.377 (2)
O3—C9	1.2329 (18)	C3—H3	0.9300
O2—C5	1.3714 (19)	C7—C6	1.379 (2)
O2—C8	1.410 (2)	C7—C2	1.384 (2)
N1—C9	1.314 (2)	C7—H7	0.9300
N1—N2	1.413 (2)	C6—C5	1.368 (2)
N1—H1	0.88 (2)	C6—H6	0.9300
N2—H2B	0.91 (2)	C9—C8	1.498 (2)
N2—H2A	0.89 (2)	C5—C4	1.380 (2)
C1—H1A	0.9600	C8—H8A	0.9700
C1—H1B	0.9600	C8—H8B	0.9700
C1—H1C	0.9600	C4—H4	0.9300
C2—O1—C1	117.82 (13)	C3—C2—C7	119.18 (15)
C5—O2—C8	117.75 (11)	O1—C2—C7	124.33 (16)
C9—N1—N2	121.34 (14)	C5—C6—C7	120.86 (14)
C9—N1—H1	121.3 (13)	C5—C6—H6	119.6
N2—N1—H1	117.2 (14)	C7—C6—H6	119.6
N1—N2—H2B	104.8 (14)	O3—C9—N1	123.78 (15)
N1—N2—H2A	107.4 (13)	O3—C9—C8	118.28 (13)
H2B—N2—H2A	107.8 (19)	N1—C9—C8	117.92 (13)
O1—C1—H1A	109.5	C6—C5—O2	116.09 (13)
O1—C1—H1B	109.5	C6—C5—C4	119.31 (14)
H1A—C1—H1B	109.5	O2—C5—C4	124.59 (14)
O1—C1—H1C	109.5	O2—C8—C9	110.77 (12)
H1A—C1—H1C	109.5	O2—C8—H8A	109.5
H1B—C1—H1C	109.5	C9—C8—H8A	109.5
C2—C3—C4	120.96 (14)	O2—C8—H8B	109.5
C2—C3—H3	119.5	C9—C8—H8B	109.5
C4—C3—H3	119.5	H8A—C8—H8B	108.1
C6—C7—C2	119.79 (16)	C3—C4—C5	119.86 (15)
C6—C7—H7	120.1	C3—C4—H4	120.1
C2—C7—H7	120.1	C5—C4—H4	120.1
C3—C2—O1	116.49 (14)
C4—C3—C2—O1	178.88 (17)	C7—C6—C5—C4	−1.7 (3)
C4—C3—C2—C7	−0.8 (3)	C8—O2—C5—C6	−175.24 (14)
C1—O1—C2—C3	177.62 (16)	C8—O2—C5—C4	5.8 (2)
C1—O1—C2—C7	−2.7 (3)	C5—O2—C8—C9	167.00 (14)
C6—C7—C2—C3	0.9 (3)	O3—C9—C8—O2	176.64 (14)
C6—C7—C2—O1	−178.80 (17)	N1—C9—C8—O2	−4.9 (2)
C2—C7—C6—C5	0.4 (3)	C2—C3—C4—C5	−0.5 (3)
N2—N1—C9—O3	4.3 (2)	C6—C5—C4—C3	1.7 (3)
N2—N1—C9—C8	−174.01 (14)	O2—C5—C4—C3	−179.35 (17)
C7—C6—C5—O2	179.31 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.89 (2)	2.51 (2)	3.155 (2)	130.4 (16)
N1—H1···N2ii	0.88 (2)	2.18 (2)	2.984 (2)	152.2 (18)
N2—H2B···O3iii	0.91 (2)	2.13 (2)	3.027 (2)	167.5 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.89 (2)	2.51 (2)	3.155 (2)	130.4 (16)
N1—H1⋯N2ii	0.88 (2)	2.18 (2)	2.984 (2)	152.2 (18)
N2—H2B⋯O3iii	0.91 (2)	2.13 (2)	3.027 (2)	167.5 (18)

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