2-(4-Meth­oxy­phen­oxy)acetohydrazide

Liu, G.; Gao, J.

doi:10.1107/S160053681202435X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1969

doi:10.1107/S160053681202435X

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2-(4-Methoxyphenoxy)acetohydrazide

Gang Liu ^a ^* and Jie Gao ^a

^aCollege of Food Engineering, Jilin Teachers' Institute of Engineering and Technology, 130052 Changchun, Jilin, People's Republic of China
^*Correspondence e-mail: lg2003915@163.com

(Received 5 April 2012; accepted 28 May 2012; online 31 May 2012)

The title compound, C₉H₁₂N₂O₃, was synthesized by the reaction of ethyl 2-(4-methoxyphenoxy)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 molecule. In the crystal, molecules 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_r = 196.21
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.030
wR(F²) = 0.089
S = 0.88
1631 reflections
140 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.15 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681202435X/rk2352sup1.cif

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

Supporting information file. DOI: 10.1107/S160053681202435X/rk2352Isup3.cml

checkCIF report

Comment top

Hydrazides have been of great interest for many years because they have different biological activities and been used for the synthesis of various heterocyclic compounds (Khattab, 2005; Dutkiewicz et al., 2009; Ozdemir et al., 2009; Ashiq et al., 2009; Zhang & Shi, 2009; Fun et al., 2009, 2010a,b, 2011). In order to search for new hydrazide compounds with higher bioactivity, the title compound, was synthesized. Its molecular and crystal structures were determined. The molecular structure is shown in Fig. 1. In the crystal structure (Fig. 2), molecules are linked into infinite two-dimensional networks by the classical intermolecular N–H···N and N–H···O hydrogen bonds. For parameters of these interactions, see Table 1.

Related literature top

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 top

The title compound was synthesized by the reaction of 2-(4-methoxyphenoxy)acetate (1 mmol) with hydrazine hydrate 85% (1.1 mmol) in ethanol (15 ml) under reflux conditions (338 K) for 5 h. The solvent was removed and the solid product recrystallized from ethanol. After six days colourless crystals suitable for X-ray diffraction study were obtained.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The structure of the infinite two-dimensional networks formed via hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonds have been omitted for clarity.

2-(4-Methoxyphenoxy)acetohydrazide top

Crystal data top

C₉H₁₂N₂O₃	F(000) = 416
M_r = 196.21	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.070P)² + 0.087P] where P = (F_o² + 2F_c²)/3
1631 reflections	(Δ/σ)_max < 0.001
140 parameters	Δρ_max = 0.09 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₉H₁₂N₂O₃	V = 930.9 (7) Å³
M_r = 196.21	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.0964 (17) Å	µ = 0.11 mm⁻¹
b = 6.382 (3) Å	T = 298 K
c = 35.608 (14) Å	0.30 × 0.25 × 0.18 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	1631 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1503 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.981	R_int = 0.021
4782 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	Δρ_max = 0.09 e Å⁻³
1631 reflections	Δρ_min = −0.15 e Å⁻³
140 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+5/2, −z+1; (ii) x+1/2, −y+3/2, −z+1; (iii) x+1/2, −y+5/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₉H₁₂N₂O₃
M_r	196.21
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	4.0964 (17), 6.382 (3), 35.608 (14)
V (Å³)	930.9 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.25 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.969, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	4782, 1631, 1503
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.089, 0.88
No. of reflections	1631
No. of parameters	140
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.15

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+5/2, −z+1; (ii) x+1/2, −y+3/2, −z+1; (iii) x+1/2, −y+5/2, −z+1.

References

Ashiq, U., Jamal, R. A., Tahir, M. N., Yousuf, S. & Khan, I. U. (2009). Acta Cryst. E65, o1551. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dutkiewicz, G., Chidan Kumar, C. S., Narayana, B., Yathirajan, H. S. & Kubicki, M. (2009). Acta Cryst. E65, o3189. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Isloor, A. M., Sunil, D. & Shetty, P. (2010a). Acta Cryst. E66, o31–o32. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Isloor, A. M., Sunil, D. & Shetty, P. (2010b). Acta Cryst. E66, o53–o54. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Malladi, S. M. V. A. & Isloor, A. M. (2011). Acta Cryst. E67, o165. Web of Science CrossRef IUCr Journals Google Scholar
Fun, H.-K., Quah, C. K., Sujith, K. V. & Kalluraya, B. (2009). Acta Cryst. E65, o1184–o1185. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khattab, S. N. (2005). Molecules, 10, 1218-1228. Web of Science CrossRef PubMed CAS Google Scholar
Ozdemir, A., Turan-Zitouni, G., Kaplancikli, Z. A. & Tunali, Y. (2009). J. Enzyme Inhib. Med. Chem. 24, 825-831. Web of Science PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Y.-X. & Shi, Z.-Q. (2009). Acta Cryst. E65, o1538. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 6| June 2012| Page o1969

doi:10.1107/S160053681202435X

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