(E)-N′-Benzyl­idene-5-methyl­isoxazole-4-carbohydrazide

Jin, Y.-X.; Jia, W.-P.; Wu, J.-Y.; Yan, H.

doi:10.1107/S1600536809052969

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o123

doi:10.1107/S1600536809052969

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(E)-N′-Benzylidene-5-methylisoxazole-4-carbohydrazide

Yan-Xian Jin,^a ^* Wen-Ping Jia,^a Jun-Yong Wu ^a and Hua Yan ^a

^aSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Linhai 317000, People's Republic of China
^*Correspondence e-mail: snowflakej@gmail.com

(Received 4 December 2009; accepted 9 December 2009; online 12 December 2009)

The molecule of the title compound, C₁₂H₁₁N₃O₂, is approximately planar with an r.m.s. deviation of 0.0814 Å from the plane through all the non-H atoms. The dihedral angle formed by the benzene and isoxazole rings is 6.88 (16)°. The molecular conformation is stabilized by an intramolecular C—H⋯N hydrogen bond, forming an S(6) ring, and the molecule displays an E configuration with respect to the C=N double bond. In the crystal structure, intermolecular N—H⋯O hydrogen bonds form centrosymmetric dimers which are further linked by weak C—H⋯N interactions augmented by very weak C—H⋯π contacts, forming layers parallel to (120).

Related literature

For the biological activity and coordination ability of hydrazone compounds, see: Molina et al. (1994 ); Khattab (2005 ); Reiter et al. (1985 ). For the biological properties of isoxazole derivatives, see: Stevens & Albizati (1984 ). For related structures, see: Fun et al. (2008 ); Wei et al. (2009 ); Khaledi et al. (2008 ). For reference bond-length parameters, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₂H₁₁N₃O₂
M_r = 229.24
Triclinic, $[P \overline 1]$
a = 6.6562 (6) Å
b = 7.4874 (9) Å
c = 11.3051 (11) Å
α = 87.319 (8)°
β = 84.640 (7)°
γ = 87.878 (8)°
V = 560.04 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.22 × 0.19 × 0.08 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.979, T_max = 0.992
6763 measured reflections
1936 independent reflections
1219 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.095
wR(F²) = 0.302
S = 1.10
1936 reflections
159 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N3	0.93	2.39	2.893 (5)	114
N2—H2⋯O2ⁱ	0.90 (1)	1.98 (1)	2.867 (4)	170 (4)
C1—H1B⋯N1ⁱⁱ	0.96	2.67	3.598 (6)	162
C1—H1A⋯Cg1ⁱⁱⁱ	0.96	3.35	4.136 (7)	140
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1. Cg1 is the centroid of the C7–C12 ring.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809052969/sj2706sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052969/sj2706Isup2.hkl

checkCIF report

Comment top

A large number of hydrazone derivatives have been reported recently (Fun et al. 2008; Wei et al. 2009; Khaledi et al. 2008) and their biological activity (Molina et al. 1994; Khattab 2005) and coordination ability (Reiter et al.1985) have also been noted. Isoxazole compounds have also attracted much interest as they exhibit some fungicidal, plant-growth regulating and antibacterial activity (Stevens et al.1984). In order to study the properties of a new compound containing both the hydrazine and isoxazole groups, we synthesized the title compound and report its crystal structure here, Fig 1.

The title compound C₁₂H₁₁N₃O₂, is approximately planar (rms deviation 0.0814 from the plane through all non-hydrogen atoms)with a dihedral angle of 6.88 (16)°. between the C7···C12 benzene and C2···C4,N1,O1 isoxazole rings. The molecule displays an E configuration with respect to the C6═N3 double bond, with a C7—C6—N3—N2 torsion angle of -179.3 (3)°. The dihedral angle formed by the benzene and isoxazole rings is 2.457 (114)°. An intramolecular C—H···N hydrogen bond generates an S6 ring motif (Bernstein et al. 1997) and locks the molecule into a planar configuration. Bond lengths (Allen et al.,1987) and angles are unexceptional and similar to those found in related stuctures (Fun et al., 2008; Wei et al., 2009; Khaledi et al., 2008).

In the crystal structure (Fig. 2), intermolecular N2—H2···O2 hydrogen bonds form centrosymmetric dimers. These are further linked by weak C1—H1B···N1 interactions augmented by very weak, inversion related C1—H1A···Cg1 contacts to form layers parallel to [120] (Cg1 is the centroid of the C7···C12 phenyl ring).

Related literature top

For the biological activity and coordination ability of hydrazone compounds, see: Molina et al. (1994); Khattab (2005); Reiter et al. (1985). For the biological properties of isoxazole derivatives, see: Stevens & Albizati (1984). For related structures, see: Fun et al. (2008); Wei et al. (2009); Khaledi et al. (2008). For reference bond-length parameters, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

Benzaldehyde (4.6 g,0.02 mol) and 5-methylisoxazole-4-carbonyl hydrazine (2.8 g, 0.02 mol) was mixed with glacial acetic acid (50 ml). The mixture was heated at 65° C for 3 h, the precipitate collected by filtration and washed with water, chloroform and ethanol. The product was recrystallized from ethanol, then dried under reduced pressure to give the title compound in 85% yield. Colourless, block-shaped crystals were obtained by slow evaporation of a dimethylformamide solution.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of of the title compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Packing diagram of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

(E)-N'-Benzylidene-5-methylisoxazole-4-carbohydrazide top

Crystal data top

C₁₂H₁₁N₃O₂	Z = 2
M_r = 229.24	F(000) = 240
Triclinic, P1	D_x = 1.359 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6562 (6) Å	Cell parameters from 1711 reflections
b = 7.4874 (9) Å	θ = 2.7–23.4°
c = 11.3051 (11) Å	µ = 0.10 mm⁻¹
α = 87.319 (8)°	T = 293 K
β = 84.640 (7)°	Block, colourless
γ = 87.878 (8)°	0.22 × 0.19 × 0.08 mm
V = 560.04 (10) Å³

Data collection top

Bruker APEXII area-detector diffractometer	1936 independent reflections
Radiation source: fine-focus sealed tube	1219 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→7
T_min = 0.979, T_max = 0.992	k = −8→8
6763 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)] = 0.095	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.302	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
1936 reflections	(Δ/σ)_max = 0.004
159 parameters	Δρ_max = 0.53 e Å⁻³
1 restraint	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₂H₁₁N₃O₂	γ = 87.878 (8)°
M_r = 229.24	V = 560.04 (10) Å³
Triclinic, P1	Z = 2
a = 6.6562 (6) Å	Mo Kα radiation
b = 7.4874 (9) Å	µ = 0.10 mm⁻¹
c = 11.3051 (11) Å	T = 293 K
α = 87.319 (8)°	0.22 × 0.19 × 0.08 mm
β = 84.640 (7)°

Data collection top

Bruker APEXII area-detector diffractometer	1936 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1219 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.992	R_int = 0.040
6763 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.095	1 restraint
wR(F²) = 0.302	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.53 e Å⁻³
1936 reflections	Δρ_min = −0.34 e Å⁻³
159 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
C1	0.1634 (6)	0.4088 (7)	0.0931 (4)	0.0719 (13)
H1A	0.1434	0.5364	0.0932	0.108*
H1B	0.0435	0.3528	0.1282	0.108*
H1C	0.1922	0.3726	0.0128	0.108*
C2	0.3348 (5)	0.3544 (5)	0.1625 (3)	0.0564 (11)
C3	0.5697 (5)	0.2840 (6)	0.2794 (3)	0.0617 (11)
H3	0.6344	0.2629	0.3484	0.074*
C4	0.3642 (5)	0.3410 (5)	0.2793 (3)	0.0504 (10)
C5	0.2072 (5)	0.3862 (5)	0.3748 (3)	0.0522 (10)
C6	0.4198 (6)	0.2675 (5)	0.6388 (3)	0.0569 (10)
H6	0.3092	0.3072	0.6882	0.068*
C7	0.5963 (6)	0.1885 (5)	0.6923 (3)	0.0535 (10)
C8	0.7688 (6)	0.1292 (6)	0.6238 (4)	0.0636 (11)
H8	0.7727	0.1374	0.5413	0.076*
C9	0.9325 (6)	0.0591 (6)	0.6767 (4)	0.0726 (13)
H9	1.0466	0.0202	0.6299	0.087*
C10	0.9299 (7)	0.0456 (6)	0.7985 (4)	0.0741 (13)
H10	1.0417	−0.0017	0.8342	0.089*
C11	0.7604 (7)	0.1027 (6)	0.8669 (4)	0.0785 (14)
H11	0.7569	0.0934	0.9493	0.094*
C12	0.5962 (7)	0.1736 (6)	0.8140 (4)	0.0684 (12)
H12	0.4826	0.2122	0.8613	0.082*
H2	0.150 (5)	0.408 (5)	0.545 (3)	0.075 (12)*
N1	0.6576 (5)	0.2644 (5)	0.1742 (3)	0.0742 (12)
N2	0.2397 (4)	0.3615 (4)	0.4894 (3)	0.0578 (9)
N3	0.4137 (5)	0.2831 (4)	0.5270 (3)	0.0546 (9)
O1	0.5060 (4)	0.3099 (4)	0.0977 (2)	0.0689 (10)
O2	0.0417 (4)	0.4503 (4)	0.3494 (2)	0.0672 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.052 (2)	0.111 (3)	0.051 (2)	0.007 (2)	−0.0067 (19)	0.012 (2)
C2	0.039 (2)	0.072 (2)	0.054 (2)	0.0057 (17)	0.0052 (16)	0.0055 (18)
C3	0.041 (2)	0.095 (3)	0.046 (2)	0.0154 (19)	0.0029 (16)	−0.0016 (19)
C4	0.0349 (19)	0.065 (2)	0.049 (2)	0.0093 (15)	0.0018 (15)	0.0009 (16)
C5	0.037 (2)	0.068 (2)	0.051 (2)	0.0094 (16)	0.0003 (15)	−0.0050 (17)
C6	0.045 (2)	0.072 (2)	0.051 (2)	0.0075 (17)	0.0048 (17)	−0.0029 (17)
C7	0.050 (2)	0.062 (2)	0.047 (2)	0.0037 (17)	0.0017 (16)	−0.0022 (16)
C8	0.054 (2)	0.084 (3)	0.051 (2)	0.010 (2)	0.0017 (18)	−0.0024 (19)
C9	0.053 (2)	0.086 (3)	0.077 (3)	0.017 (2)	−0.002 (2)	−0.003 (2)
C10	0.066 (3)	0.080 (3)	0.078 (3)	0.015 (2)	−0.021 (2)	0.004 (2)
C11	0.078 (3)	0.099 (3)	0.057 (3)	0.020 (3)	−0.011 (2)	0.002 (2)
C12	0.065 (3)	0.087 (3)	0.052 (2)	0.016 (2)	0.0003 (19)	−0.004 (2)
N1	0.0411 (19)	0.121 (3)	0.057 (2)	0.0189 (18)	0.0007 (15)	0.0025 (19)
N2	0.0372 (17)	0.087 (2)	0.0468 (19)	0.0153 (15)	0.0002 (13)	−0.0059 (16)
N3	0.0408 (17)	0.073 (2)	0.0486 (19)	0.0090 (14)	−0.0024 (13)	−0.0020 (14)
O1	0.0457 (16)	0.113 (2)	0.0448 (16)	0.0136 (14)	0.0042 (12)	0.0022 (14)
O2	0.0419 (16)	0.104 (2)	0.0547 (17)	0.0250 (14)	−0.0063 (12)	−0.0128 (14)

Geometric parameters (Å, º) top

C1—C2	1.478 (5)	C7—C12	1.375 (5)
C1—H1A	0.9600	C7—C8	1.394 (5)
C1—H1B	0.9600	C8—C9	1.368 (5)
C1—H1C	0.9600	C8—H8	0.9300
C2—O1	1.337 (4)	C9—C10	1.374 (6)
C2—C4	1.352 (5)	C9—H9	0.9300
C3—N1	1.288 (5)	C10—C11	1.373 (6)
C3—C4	1.417 (5)	C10—H10	0.9300
C3—H3	0.9300	C11—C12	1.373 (6)
C4—C5	1.473 (5)	C11—H11	0.9300
C5—O2	1.239 (4)	C12—H12	0.9300
C5—N2	1.336 (5)	N1—O1	1.412 (4)
C6—N3	1.269 (5)	N2—N3	1.373 (4)
C6—C7	1.464 (5)	N2—H2	0.902 (10)
C6—H6	0.9300

C2—C1—H1A	109.5	C8—C7—C6	122.2 (3)
C2—C1—H1B	109.5	C9—C8—C7	120.7 (4)
H1A—C1—H1B	109.5	C9—C8—H8	119.7
C2—C1—H1C	109.5	C7—C8—H8	119.7
H1A—C1—H1C	109.5	C8—C9—C10	120.6 (4)
H1B—C1—H1C	109.5	C8—C9—H9	119.7
O1—C2—C4	109.7 (3)	C10—C9—H9	119.7
O1—C2—C1	115.1 (3)	C11—C10—C9	119.2 (4)
C4—C2—C1	135.3 (4)	C11—C10—H10	120.4
N1—C3—C4	113.2 (3)	C9—C10—H10	120.4
N1—C3—H3	123.4	C12—C11—C10	120.3 (4)
C4—C3—H3	123.4	C12—C11—H11	119.9
C2—C4—C3	103.5 (3)	C10—C11—H11	119.9
C2—C4—C5	123.5 (3)	C11—C12—C7	121.3 (4)
C3—C4—C5	133.0 (3)	C11—C12—H12	119.4
O2—C5—N2	118.7 (3)	C7—C12—H12	119.4
O2—C5—C4	119.9 (3)	C3—N1—O1	104.4 (3)
N2—C5—C4	121.4 (3)	C5—N2—N3	123.3 (3)
N3—C6—C7	121.8 (3)	C5—N2—H2	119 (3)
N3—C6—H6	119.1	N3—N2—H2	118 (3)
C7—C6—H6	119.1	C6—N3—N2	115.5 (3)
C12—C7—C8	117.9 (4)	C2—O1—N1	109.3 (3)
C12—C7—C6	119.8 (4)

O1—C2—C4—C3	0.0 (4)	C7—C8—C9—C10	0.0 (7)
C1—C2—C4—C3	−178.5 (5)	C8—C9—C10—C11	0.3 (7)
O1—C2—C4—C5	178.0 (3)	C9—C10—C11—C12	−0.4 (8)
C1—C2—C4—C5	−0.5 (8)	C10—C11—C12—C7	0.3 (8)
N1—C3—C4—C2	0.0 (5)	C8—C7—C12—C11	0.1 (7)
N1—C3—C4—C5	−177.7 (4)	C6—C7—C12—C11	−179.0 (4)
C2—C4—C5—O2	−4.5 (6)	C4—C3—N1—O1	0.0 (5)
C3—C4—C5—O2	172.8 (4)	O2—C5—N2—N3	176.6 (3)
C2—C4—C5—N2	176.3 (4)	C4—C5—N2—N3	−4.2 (6)
C3—C4—C5—N2	−6.4 (7)	C7—C6—N3—N2	−179.3 (3)
N3—C6—C7—C12	−179.8 (4)	C5—N2—N3—C6	−179.1 (4)
N3—C6—C7—C8	1.2 (6)	C4—C2—O1—N1	0.0 (5)
C12—C7—C8—C9	−0.2 (7)	C1—C2—O1—N1	178.8 (3)
C6—C7—C8—C9	178.8 (4)	C3—N1—O1—C2	0.0 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N3	0.93	2.39	2.893 (5)	114
N2—H2···O2ⁱ	0.90 (1)	1.98 (1)	2.867 (4)	170 (4)
C1—H1B···N1ⁱⁱ	0.96	2.67	3.598 (6)	162
C1—H1A···Cg1ⁱⁱⁱ	0.96	3.35	4.136 (7)	140

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁N₃O₂
M_r	229.24
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.6562 (6), 7.4874 (9), 11.3051 (11)
α, β, γ (°)	87.319 (8), 84.640 (7), 87.878 (8)
V (Å³)	560.04 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.22 × 0.19 × 0.08

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.979, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	6763, 1936, 1219
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.095, 0.302, 1.10
No. of reflections	1936
No. of parameters	159
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.34

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N3	0.93	2.39	2.893 (5)	113.7
N2—H2···O2ⁱ	0.902 (10)	1.975 (13)	2.867 (4)	170 (4)
C1—H1B···N1ⁱⁱ	0.96	2.67	3.598 (6)	161.8
C1—H1A···Cg1ⁱⁱⁱ	0.96	3.352	4.136 (7)	140.2

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

Acknowledgements

The authors acknowledge financial support by the Zhejiang Provincial Natural Science Foundation of China (No. Y406049).

References

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