N′-[1-(4-Methoxy­phen­yl)ethyl­idene]acetohydrazide

Li, Y.-F.; Jian, F.-F.

doi:10.1107/S1600536808037677

organic compounds

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Volume 64| Part 12| December 2008| Page o2409

doi:10.1107/S1600536808037677

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N′-[1-(4-Methoxyphenyl)ethylidene]acetohydrazide

Yu-Feng Li ^a and Fang-Fang Jian ^a ^*

^aMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: ffjian2008@163.com

(Received 20 October 2008; accepted 13 November 2008; online 22 November 2008)

The title compound, C₁₁H₁₄N₂O₂, was prepared by the reaction of acetohydrazide and 1-(4-methoxyphenyl)ethanone. In the molecule, all bond lengths and angles are within normal ranges. In the crystal structure, adjacent molecules are linked into a centrosymmetric dimer by intermolecular N—H⋯O hydrogen bonding.

Related literature

For related literature, see: Cimerman et al. (1997 ); Girgis (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₄N₂O₂
M_r = 206.24
Monoclinic, P 2₁ /n
a = 13.282 (3) Å
b = 4.9923 (10) Å
c = 16.854 (3) Å
β = 98.88 (3)°
V = 1104.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.25 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
6830 measured reflections
2681 independent reflections
1228 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.196
S = 0.93
2681 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.86	2.12	2.956 (3)	166
Symmetry code: (i) -x+2, -y, -z+2.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037677/at2657sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037677/at2657Isup2.hkl

checkCIF report

Comment top

Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman et al., 1997). As part of our search for new Schiff base compounds we synthesized the title compound (I), and describe its structure here.

In the title compound (Fig. 1), all bond lengths and angles are within normal ranges (Allen et al., 1987). The C8—N1 bond length of 1.278 (3)Å is comparable with C—N double bond [1.281 (2) Å] reported (Girgis, 2006).

In the crystal structure, adjacent molecules are linked into a centro-symmetric supra-molecular dimer by intermolecular N—H···O hydrogen bonding (Table 1, Fig. 2).

Related literature top

For related literature, see: Cimerman et al. (1997); Girgis (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of the acetohydrazide (0.1 mol), and 1-(4-methoxyphenyl)ethanone (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.080 mol, yield 80%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Part of the crystal structure of the title compound showing the formation of a cyclic centrosymmetric dimer. For the sake of clarity, H atoms not involved in hydrogen bonding have been omitted.

N'-[1-(4-Methoxyphenyl)ethylidene]acetohydrazide top

Crystal data top

C₁₁H₁₄N₂O₂	F(000) = 440
M_r = 206.24	D_x = 1.241 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 831 reflections
a = 13.282 (3) Å	θ = 2.4–24.0°
b = 4.9923 (10) Å	µ = 0.09 mm⁻¹
c = 16.854 (3) Å	T = 293 K
β = 98.88 (3)°	Block, yellow
V = 1104.2 (4) Å³	0.25 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	1228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 28.3°, θ_min = 1.8°
ϕ and ω scans	h = −17→15
6830 measured reflections	k = −6→6
2681 independent reflections	l = −16→22

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.196	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0986P)² + 0.0719P] where P = (F_o² + 2F_c²)/3
2681 reflections	(Δ/σ)_max < 0.001
137 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₁H₁₄N₂O₂	V = 1104.2 (4) Å³
M_r = 206.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.282 (3) Å	µ = 0.09 mm⁻¹
b = 4.9923 (10) Å	T = 293 K
c = 16.854 (3) Å	0.25 × 0.20 × 0.18 mm
β = 98.88 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1228 reflections with I > 2σ(I)
6830 measured reflections	R_int = 0.035
2681 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.196	H-atom parameters constrained
S = 0.93	Δρ_max = 0.17 e Å⁻³
2681 reflections	Δρ_min = −0.17 e Å⁻³
137 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
O2	0.98272 (13)	0.2016 (4)	0.91643 (10)	0.0761 (6)
O1	1.64324 (12)	0.8045 (4)	1.19345 (10)	0.0788 (6)
N2	1.12429 (14)	0.2219 (4)	1.00666 (11)	0.0631 (6)
H2A	1.1037	0.0925	1.0338	0.076*
N1	1.21780 (14)	0.3415 (4)	1.03226 (11)	0.0608 (5)
C5	1.36778 (17)	0.4053 (4)	1.12310 (13)	0.0559 (6)
C10	1.06577 (19)	0.3085 (5)	0.93934 (14)	0.0606 (6)
C8	1.26860 (17)	0.2683 (4)	1.09940 (13)	0.0572 (6)
C2	1.55227 (16)	0.6811 (5)	1.16686 (13)	0.0588 (6)
C7	1.51710 (18)	0.5048 (5)	1.21885 (14)	0.0675 (7)
H7A	1.5547	0.4775	1.2695	0.081*
C3	1.49509 (19)	0.7215 (5)	1.09293 (15)	0.0739 (8)
H3A	1.5174	0.8408	1.0570	0.089*
C4	1.40476 (19)	0.5860 (6)	1.07177 (14)	0.0752 (8)
H4A	1.3671	0.6163	1.0213	0.090*
C6	1.42740 (18)	0.3683 (5)	1.19720 (13)	0.0632 (7)
H6A	1.4061	0.2477	1.2333	0.076*
C11	1.1030 (2)	0.5331 (5)	0.89359 (15)	0.0754 (7)
H11A	1.0532	0.5729	0.8475	0.113*
H11B	1.1660	0.4828	0.8764	0.113*
H11C	1.1137	0.6886	0.9273	0.113*
C9	1.2343 (2)	0.0599 (6)	1.15380 (17)	0.0931 (10)
H9A	1.1689	0.1090	1.1668	0.159 (16)*
H9B	1.2828	0.0482	1.2022	0.239*
H9C	1.2292	−0.1105	1.1271	0.239*
C1	1.68123 (19)	0.9957 (5)	1.14314 (16)	0.0807 (8)
H1B	1.7453	1.0639	1.1695	0.121*
H1C	1.6335	1.1404	1.1324	0.121*
H1D	1.6906	0.9120	1.0935	0.121*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0790 (12)	0.0801 (12)	0.0670 (11)	−0.0227 (10)	0.0048 (9)	0.0087 (9)
O1	0.0687 (11)	0.0908 (13)	0.0735 (12)	−0.0172 (10)	0.0003 (9)	0.0073 (10)
N2	0.0729 (13)	0.0604 (12)	0.0562 (12)	−0.0161 (10)	0.0109 (10)	0.0038 (9)
N1	0.0651 (12)	0.0615 (12)	0.0562 (12)	−0.0126 (9)	0.0107 (9)	−0.0025 (9)
C5	0.0640 (13)	0.0541 (13)	0.0515 (13)	−0.0032 (11)	0.0153 (11)	−0.0005 (10)
C10	0.0718 (16)	0.0557 (14)	0.0558 (14)	−0.0084 (12)	0.0145 (12)	−0.0020 (11)
C8	0.0674 (15)	0.0560 (14)	0.0506 (13)	−0.0047 (12)	0.0162 (11)	−0.0009 (11)
C2	0.0598 (14)	0.0620 (14)	0.0549 (13)	0.0000 (11)	0.0097 (11)	0.0000 (11)
C7	0.0722 (15)	0.0773 (16)	0.0510 (13)	−0.0031 (14)	0.0033 (11)	0.0059 (12)
C3	0.0746 (16)	0.0863 (19)	0.0598 (15)	−0.0177 (15)	0.0072 (13)	0.0196 (14)
C4	0.0759 (16)	0.0917 (19)	0.0542 (14)	−0.0197 (15)	−0.0016 (12)	0.0178 (13)
C6	0.0768 (16)	0.0603 (14)	0.0533 (14)	−0.0024 (12)	0.0130 (12)	0.0081 (11)
C11	0.0877 (17)	0.0683 (16)	0.0696 (16)	−0.0160 (14)	0.0099 (13)	0.0132 (13)
C9	0.101 (2)	0.097 (2)	0.0798 (19)	−0.0350 (18)	0.0105 (16)	0.0259 (17)
C1	0.0726 (16)	0.0842 (19)	0.0872 (18)	−0.0190 (15)	0.0183 (14)	0.0019 (16)

Geometric parameters (Å, º) top

O2—C10	1.232 (3)	C7—H7A	0.9300
O1—C2	1.369 (3)	C3—C4	1.376 (3)
O1—C1	1.420 (3)	C3—H3A	0.9300
N2—C10	1.344 (3)	C4—H4A	0.9300
N2—N1	1.386 (2)	C6—H6A	0.9300
N2—H2A	0.8600	C11—H11A	0.9600
N1—C8	1.278 (3)	C11—H11B	0.9600
C5—C6	1.384 (3)	C11—H11C	0.9600
C5—C4	1.391 (3)	C9—H9A	0.9600
C5—C8	1.483 (3)	C9—H9B	0.9600
C10—C11	1.488 (3)	C9—H9C	0.9600
C8—C9	1.503 (3)	C1—H1B	0.9600
C2—C3	1.370 (3)	C1—H1C	0.9600
C2—C7	1.374 (3)	C1—H1D	0.9600
C7—C6	1.372 (3)

C2—O1—C1	118.96 (19)	C3—C4—H4A	118.8
C10—N2—N1	119.9 (2)	C5—C4—H4A	118.8
C10—N2—H2A	120.1	C7—C6—C5	121.7 (2)
N1—N2—H2A	120.1	C7—C6—H6A	119.1
C8—N1—N2	118.54 (19)	C5—C6—H6A	119.1
C6—C5—C4	116.1 (2)	C10—C11—H11A	109.5
C6—C5—C8	122.8 (2)	C10—C11—H11B	109.5
C4—C5—C8	121.0 (2)	H11A—C11—H11B	109.5
O2—C10—N2	119.9 (2)	C10—C11—H11C	109.5
O2—C10—C11	121.1 (2)	H11A—C11—H11C	109.5
N2—C10—C11	119.0 (2)	H11B—C11—H11C	109.5
N1—C8—C5	115.6 (2)	C8—C9—H9A	109.5
N1—C8—C9	124.7 (2)	C8—C9—H9B	109.5
C5—C8—C9	119.7 (2)	H9A—C9—H9B	109.5
O1—C2—C3	124.7 (2)	C8—C9—H9C	109.5
O1—C2—C7	116.7 (2)	H9A—C9—H9C	109.5
C3—C2—C7	118.6 (2)	H9B—C9—H9C	109.5
C6—C7—C2	121.0 (2)	O1—C1—H1B	109.5
C6—C7—H7A	119.5	O1—C1—H1C	109.5
C2—C7—H7A	119.5	H1B—C1—H1C	109.5
C2—C3—C4	120.1 (2)	O1—C1—H1D	109.5
C2—C3—H3A	119.9	H1B—C1—H1D	109.5
C4—C3—H3A	119.9	H1C—C1—H1D	109.5
C3—C4—C5	122.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.12	2.956 (3)	166
C4—H4A···N1	0.93	2.44	2.755 (3)	100

Symmetry code: (i) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄N₂O₂
M_r	206.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.282 (3), 4.9923 (10), 16.854 (3)
β (°)	98.88 (3)
V (Å³)	1104.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6830, 2681, 1228
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.196, 0.93
No. of reflections	2681
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.17

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.12	2.956 (3)	166

Symmetry code: (i) −x+2, −y, −z+2.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153. CrossRef CAS Web of Science Google Scholar
Girgis, A. S. (2006). J. Chem. Res. pp. 81–85. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2409

doi:10.1107/S1600536808037677

Open

access