(E)-N'-Benzyl-idene-5-methyl-isoxazole-4-carbohydrazide.

The mol-ecule of the title compound, C(12)H(11)N(3)O(2), 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 mol-ecular conformation is stabilized by an intra-molecular C-H⋯N hydrogen bond, forming an S(6) ring, and the mol-ecule displays an E configuration with respect to the C=N double bond. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds form centrosymmetric dimers which are further linked by weak C-H⋯N inter-actions 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 = 229.24

Triclinic,

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[F 2 > 2σ(F 2)] = 0.095

wR(F 2) = 0.302

S = 1.10

1936 reflections

159 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.34 e Å−3

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.

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

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

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

C12H11N3O2	Z = 2
Mr = 229.24	F(000) = 240
Triclinic, P1	Dx = 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

Bruker APEXII area-detector diffractometer	1936 independent reflections
Radiation source: fine-focus sealed tube	1219 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→7
Tmin = 0.979, Tmax = 0.992	k = −8→8
6763 measured reflections	l = −13→13

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(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3
1936 reflections	(Δ/σ)max = 0.004
159 parameters	Δρmax = 0.53 e Å−3
1 restraint	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) ; (iii) . Cg1 is the centroid of the C7–C12 ring.