N′-(2-Meth­oxy­benzyl­idene)aceto­hydrazide

Yu, T.-M.; Lv, L.-P.

doi:10.1107/S1600536810038092

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2666

doi:10.1107/S1600536810038092

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N′-(2-Methoxybenzylidene)acetohydrazide

Tie-Ming Yu ^a and Lu-Ping Lv ^a ^*

^aLinjiang College, Hangzhou Vocational and Technical College, Hangzhou 310018, People's Republic of China
^*Correspondence e-mail: mailofllp@126.com

(Received 1 September 2010; accepted 24 September 2010; online 30 September 2010)

In the title molecule, C₁₀H₁₂N₂O₂, the acetohydrazide group is almost planar [within 0.0306 (12) Å] and forms a dihedral angle of 12.15 (14)° with the benzene ring. The methoxy group deviates from the attached benzene ring with a C—O—C—C torsion angle of 4.2 (4)°·The molecule adopts a trans configuration with respect to the C=N bond. In the crystal, molecules are linked into centrosymmetric dimers by pairs of N—H⋯O hydrogen bonds and intermolecular C—H⋯O interactions further stabilize the structure.

Related literature

For general background to Schiff bases, see: Cimerman et al. (1997 ); Offe et al. (1952 ); Richardson et al. (1988 ). For related structures, see: Li & Jian (2008 ); Tamboura et al. (2009 ).

Experimental

Crystal data

C₁₀H₁₂N₂O₂
M_r = 192.22
Triclinic, $[P \overline 1]$
a = 5.3865 (7) Å
b = 8.4609 (11) Å
c = 11.3301 (14) Å
α = 77.499 (4)°
β = 76.516 (5)°
γ = 89.101 (5)°
V = 489.90 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 223 K
0.19 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.982, T_max = 0.985
4827 measured reflections
1694 independent reflections
1489 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.163
S = 1.06
1694 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.86	2.07	2.899 (2)	163
C6—H6A⋯O1ⁱⁱ	0.96	2.59	3.491 (3)	157
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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 I, global. DOI: 10.1107/S1600536810038092/gw2092sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810038092/gw2092Isup2.hkl

checkCIF report

Comment top

Schiff bases have attracted much attention due to the possibility of their analytical applications (Cimerman et al., 1997). They are also important ligands, which have been reported to have mild bacteriostatic activity and are used as potential oral iron-chelating drugs for genetic disorders such as thalassemia (Offe et al., 1952; Richardson et al., 1988). Metal complexes based on Schiff bases have received considerable attention because they can be utilized as model compounds of active centres in various complexes (Tamboura et al., 2009). We report here the crystal structure of the title compound (Fig. 1).

The acetohydrazide group is planar and it forms a dihedral angle of 12.15 (14)° with the benzene ring. deviates from the attached benzene ring by 4.2 (4)°. [C6—O1—C5—C4 = 4.2 (4)°]. The molecule adopts a trans configuration with respect to the C═N bond. Bond lengths and angles are comparable to those observed for N'-[1-(4-methoxyphenyl)ethylidene]acetohydrazide (Li & Jian, 2008).

The molecules are linked by N—H···O hydrogen bonds into a centrosymmetric dimer. In addition, an intramolecular C—H···N hydrogen bond is observed.

Related literature top

For general background to Schiff bases, see: Cimerman et al. (1997); Offe et al. (1952); Richardson et al. (1988). For related structures, see: Li & Jian (2008); Tamboura et al. (2009).

Experimental top

2-Methoxybenzaldehyde (1.36 g, 0.01 mol) and acetohydrazide (0.74 g, 0.01 mol) were dissolved in stirred methanol (25 ml) and left for 2.5 h at room temperature. The resulting solid was filtered off and recrystallized from ethanol to give the title compound in 88% yield. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature (m.p. 465–467 K).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

N'-(2-Methoxybenzylidene)acetohydrazide top

Crystal data top

C₁₀H₁₂N₂O₂	Z = 2
M_r = 192.22	F(000) = 204
Triclinic, P1	D_x = 1.303 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3865 (7) Å	Cell parameters from 1694 reflections
b = 8.4609 (11) Å	θ = 1.9–25.0°
c = 11.3301 (14) Å	µ = 0.09 mm⁻¹
α = 77.499 (4)°	T = 223 K
β = 76.516 (5)°	Block, colourless
γ = 89.101 (5)°	0.19 × 0.17 × 0.15 mm
V = 489.90 (11) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	1694 independent reflections
Radiation source: fine-focus sealed tube	1489 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −6→6
T_min = 0.982, T_max = 0.985	k = −10→9
4827 measured reflections	l = −13→13

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0812P)² + 0.265P] where P = (F_o² + 2F_c²)/3
1694 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₀H₁₂N₂O₂	γ = 89.101 (5)°
M_r = 192.22	V = 489.90 (11) Å³
Triclinic, P1	Z = 2
a = 5.3865 (7) Å	Mo Kα radiation
b = 8.4609 (11) Å	µ = 0.09 mm⁻¹
c = 11.3301 (14) Å	T = 223 K
α = 77.499 (4)°	0.19 × 0.17 × 0.15 mm
β = 76.516 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1694 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1489 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.985	R_int = 0.018
4827 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.06	Δρ_max = 0.40 e Å⁻³
1694 reflections	Δρ_min = −0.33 e Å⁻³
128 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.3030 (3)	0.1576 (2)	0.41553 (14)	0.0617 (5)
C10	0.6401 (4)	0.2210 (3)	−0.2060 (2)	0.0533 (6)
H10A	0.5000	0.2686	−0.1579	0.080*
H10B	0.5753	0.1429	−0.2424	0.080*
H10C	0.7390	0.3041	−0.2707	0.080*
N1	0.5212 (3)	0.2232 (2)	0.04470 (16)	0.0430 (5)
N2	0.7383 (3)	0.1459 (2)	−0.00176 (16)	0.0461 (5)
H2	0.8319	0.1014	0.0474	0.055*
C1	0.1048 (5)	0.3982 (3)	0.1500 (2)	0.0522 (6)
H1	0.1575	0.4195	0.0637	0.063*
C2	−0.1084 (5)	0.4724 (3)	0.2049 (2)	0.0576 (6)
H2A	−0.1987	0.5420	0.1560	0.069*
C3	−0.1852 (5)	0.4423 (3)	0.3321 (2)	0.0572 (6)
H3	−0.3285	0.4917	0.3696	0.069*
C4	−0.0514 (5)	0.3388 (3)	0.4053 (2)	0.0562 (6)
H4	−0.1048	0.3197	0.4915	0.067*
C5	0.1626 (4)	0.2634 (3)	0.3506 (2)	0.0462 (5)
C6	0.2348 (6)	0.1311 (4)	0.5483 (2)	0.0720 (8)
H6A	0.3527	0.0593	0.5823	0.108*
H6B	0.0651	0.0835	0.5791	0.108*
H6C	0.2408	0.2326	0.5725	0.108*
C7	0.2427 (4)	0.2924 (3)	0.22085 (19)	0.0418 (5)
C8	0.4680 (4)	0.2133 (3)	0.16151 (19)	0.0421 (5)
H8	0.5719	0.1559	0.2096	0.050*
C9	0.8059 (4)	0.1389 (3)	−0.12303 (19)	0.0424 (5)
O2	0.9982 (3)	0.0679 (2)	−0.16141 (14)	0.0528 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0686 (11)	0.0756 (12)	0.0348 (8)	0.0287 (9)	−0.0062 (7)	−0.0076 (8)
C10	0.0497 (13)	0.0723 (16)	0.0378 (12)	0.0158 (11)	−0.0097 (10)	−0.0134 (11)
N1	0.0414 (9)	0.0489 (11)	0.0373 (9)	0.0120 (7)	−0.0048 (7)	−0.0116 (8)
N2	0.0431 (10)	0.0589 (12)	0.0350 (9)	0.0181 (8)	−0.0073 (7)	−0.0107 (8)
C1	0.0573 (13)	0.0584 (14)	0.0412 (12)	0.0157 (11)	−0.0123 (10)	−0.0118 (10)
C2	0.0562 (14)	0.0611 (15)	0.0585 (15)	0.0213 (11)	−0.0178 (11)	−0.0166 (12)
C3	0.0508 (13)	0.0610 (15)	0.0602 (15)	0.0174 (11)	−0.0046 (11)	−0.0242 (12)
C4	0.0582 (14)	0.0650 (15)	0.0409 (12)	0.0131 (11)	0.0008 (10)	−0.0162 (11)
C5	0.0486 (12)	0.0489 (12)	0.0391 (11)	0.0084 (9)	−0.0070 (9)	−0.0098 (9)
C6	0.094 (2)	0.083 (2)	0.0359 (13)	0.0288 (16)	−0.0138 (13)	−0.0109 (12)
C7	0.0422 (11)	0.0440 (12)	0.0387 (11)	0.0064 (9)	−0.0070 (9)	−0.0114 (9)
C8	0.0447 (11)	0.0444 (11)	0.0360 (11)	0.0088 (9)	−0.0078 (9)	−0.0088 (9)
C9	0.0394 (11)	0.0494 (12)	0.0357 (11)	0.0065 (9)	−0.0039 (8)	−0.0091 (9)
O2	0.0479 (9)	0.0689 (11)	0.0396 (8)	0.0221 (7)	−0.0051 (7)	−0.0143 (7)

Geometric parameters (Å, º) top

O1—C5	1.367 (3)	C2—C3	1.371 (3)
O1—C6	1.430 (3)	C2—H2A	0.9300
C10—C9	1.501 (3)	C3—C4	1.385 (4)
C10—H10A	0.9600	C3—H3	0.9300
C10—H10B	0.9600	C4—C5	1.391 (3)
C10—H10C	0.9600	C4—H4	0.9300
N1—C8	1.272 (3)	C5—C7	1.399 (3)
N1—N2	1.382 (2)	C6—H6A	0.9600
N2—C9	1.351 (3)	C6—H6B	0.9600
N2—H2	0.8600	C6—H6C	0.9600
C1—C2	1.383 (3)	C7—C8	1.470 (3)
C1—C7	1.394 (3)	C8—H8	0.9300
C1—H1	0.9300	C9—O2	1.227 (2)

C5—O1—C6	117.66 (19)	C3—C4—H4	119.8
C9—C10—H10A	109.5	C5—C4—H4	119.8
C9—C10—H10B	109.5	O1—C5—C4	124.3 (2)
H10A—C10—H10B	109.5	O1—C5—C7	116.03 (19)
C9—C10—H10C	109.5	C4—C5—C7	119.7 (2)
H10A—C10—H10C	109.5	O1—C6—H6A	109.5
H10B—C10—H10C	109.5	O1—C6—H6B	109.5
C8—N1—N2	115.56 (18)	H6A—C6—H6B	109.5
C9—N2—N1	121.13 (17)	O1—C6—H6C	109.5
C9—N2—H2	119.4	H6A—C6—H6C	109.5
N1—N2—H2	119.4	H6B—C6—H6C	109.5
C2—C1—C7	121.7 (2)	C1—C7—C5	118.4 (2)
C2—C1—H1	119.2	C1—C7—C8	121.2 (2)
C7—C1—H1	119.2	C5—C7—C8	120.42 (19)
C3—C2—C1	119.2 (2)	N1—C8—C7	120.22 (19)
C3—C2—H2A	120.4	N1—C8—H8	119.9
C1—C2—H2A	120.4	C7—C8—H8	119.9
C2—C3—C4	120.6 (2)	O2—C9—N2	119.71 (19)
C2—C3—H3	119.7	O2—C9—C10	122.64 (19)
C4—C3—H3	119.7	N2—C9—C10	117.65 (18)
C3—C4—C5	120.4 (2)

C8—N1—N2—C9	175.77 (19)	O1—C5—C7—C1	179.4 (2)
C7—C1—C2—C3	0.5 (4)	C4—C5—C7—C1	0.5 (4)
C1—C2—C3—C4	0.0 (4)	O1—C5—C7—C8	−0.9 (3)
C2—C3—C4—C5	−0.3 (4)	C4—C5—C7—C8	−179.8 (2)
C6—O1—C5—C4	−4.2 (4)	N2—N1—C8—C7	179.40 (17)
C6—O1—C5—C7	176.9 (2)	C1—C7—C8—N1	−9.4 (3)
C3—C4—C5—O1	−178.8 (2)	C5—C7—C8—N1	171.0 (2)
C3—C4—C5—C7	0.0 (4)	N1—N2—C9—O2	−179.23 (19)
C2—C1—C7—C5	−0.8 (4)	N1—N2—C9—C10	1.3 (3)
C2—C1—C7—C8	179.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···N1	0.96	2.27	2.766 (3)	111
N2—H2···O2ⁱ	0.86	2.07	2.899 (2)	163
C6—H6A···O1ⁱⁱ	0.96	2.59	3.491 (3)	157

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂N₂O₂
M_r	192.22
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	5.3865 (7), 8.4609 (11), 11.3301 (14)
α, β, γ (°)	77.499 (4), 76.516 (5), 89.101 (5)
V (Å³)	489.90 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.19 × 0.17 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.982, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	4827, 1694, 1489
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.163, 1.06
No. of reflections	1694
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.33

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
C10—H10A···N1	0.96	2.27	2.766 (3)	110.9
N2—H2···O2ⁱ	0.86	2.07	2.899 (2)	162.6
C6—H6A···O1ⁱⁱ	0.96	2.59	3.491 (3)	156.5

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z+1.

Acknowledgements

The authors thank Hangzhou Vocational and Technical College for financial support.

References

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