5-Methyl-N'-(3-nitrobenzylidene)isoxazole-4-carbohydrazide.

The mol-ecule of the title compound, C(12)H(10)N(4)O(4), displays an E configuration about the C=N bond. The dihedral angle between the benzene and isoxazole rings is 1.36 (5)° and the mol-ecular conformation is stabilized by the an intra-molecular C-H⋯N hydrogen bond. In the crystal structure, centrosymmetrically related mol-ecules are connected by pairs of N-H⋯O hydrogen bonds into dimers, which are further linked into a three-dimensional network by inter-molecular C-H⋯O hydrogen bonds and by π⋯π stacking inter-actions involving adjacent benzene and isoxazole rings, with a centroid-centroid separation of 3.861 (3) Å.

Related literature

For the biological activity and coordination ability of hydrazone compounds, see: Khattab (2005 ▶); Reiter et al. (1985 ▶). For the properties of isoxazole derivatives, see: Stevens & Albizati (1984 ▶). For examples of crystal structures of hydrazone compounds, see: Fun et al. (2008 ▶); Wei et al. (2009 ▶); Khaledi et al. (2008 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H10N4O4

M = 274.24

Monoclinic,

a = 4.8668 (8) Å

b = 25.202 (4) Å

c = 10.257 (2) Å

β = 100.721 (12)°

V = 1236.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.66 × 0.30 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.951, T max = 0.971

10436 measured reflections

2828 independent reflections

1943 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.129

S = 1.10

2828 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.24 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 General, I. DOI: 10.1107/S1600536809051733/rz2400sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051733/rz2400Isup2.hkl

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

C12H10N4O4	F(000) = 568
Mr = 274.24	Dx = 1.474 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2571 reflections
a = 4.8668 (8) Å	θ = 2.6–23.7°
b = 25.202 (4) Å	µ = 0.11 mm−1
c = 10.257 (2) Å	T = 293 K
β = 100.721 (12)°	Block, colourless
V = 1236.1 (4) Å3	0.66 × 0.30 × 0.14 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2828 independent reflections
Radiation source: sealed tube	1943 reflections with I > 2σ(I)
graphite	Rint = 0.034
phi and ω scans	θmax = 27.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −5→6
Tmin = 0.951, Tmax = 0.971	k = −32→30
10436 measured reflections	l = −13→12

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.054P)2 + 0.2908P] where P = (Fo2 + 2Fc2)/3
2828 reflections	(Δ/σ)max = 0.012
186 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.24 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	−0.2323 (5)	0.37462 (8)	0.4047 (2)	0.0542 (5)
H1A	−0.4117	0.3672	0.4267	0.081*
H1B	−0.1073	0.3871	0.4823	0.081*
H1C	−0.1581	0.3429	0.3729	0.081*
C2	−0.2629 (4)	0.41576 (7)	0.30054 (17)	0.0410 (4)
C3	−0.2693 (4)	0.47950 (7)	0.15576 (17)	0.0457 (5)
H3A	−0.2179	0.5097	0.1142	0.055*
C4	−0.1173 (4)	0.45970 (7)	0.27849 (16)	0.0378 (4)
C5	0.1366 (4)	0.47775 (7)	0.36822 (16)	0.0367 (4)
C6	0.3416 (4)	0.59572 (7)	0.23565 (16)	0.0415 (5)
H6	0.4994	0.5997	0.3017	0.050*
C7	0.2862 (4)	0.63497 (7)	0.12970 (16)	0.0377 (4)
C8	0.0622 (4)	0.63082 (7)	0.02243 (17)	0.0438 (5)
H8	−0.0627	0.6027	0.0188	0.053*
C9	0.0253 (4)	0.66798 (8)	−0.07759 (18)	0.0500 (5)
H9	−0.1237	0.6646	−0.1485	0.060*
C10	0.2072 (4)	0.71022 (7)	−0.07375 (17)	0.0471 (5)
H10	0.1832	0.7354	−0.1412	0.057*
C11	0.4254 (4)	0.71402 (7)	0.03287 (16)	0.0405 (4)
C12	0.4682 (4)	0.67752 (7)	0.13459 (16)	0.0404 (4)
H12	0.6168	0.6814	0.2054	0.049*
H2	0.426 (3)	0.5310 (8)	0.4040 (16)	0.053 (6)*
N1	−0.4859 (4)	0.45108 (7)	0.10830 (15)	0.0544 (5)
N2	0.2682 (3)	0.52281 (6)	0.34603 (13)	0.0406 (4)
N3	0.1809 (3)	0.55618 (6)	0.24086 (13)	0.0395 (4)
N4	0.6224 (4)	0.75843 (6)	0.03927 (15)	0.0503 (4)
O1	−0.4845 (3)	0.40961 (5)	0.20178 (13)	0.0512 (4)
O2	0.2363 (3)	0.45160 (5)	0.46820 (11)	0.0462 (4)
O3	0.7959 (4)	0.76447 (7)	0.14015 (15)	0.0811 (6)
O4	0.6048 (4)	0.78753 (6)	−0.05611 (14)	0.0689 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0540 (14)	0.0443 (11)	0.0618 (12)	−0.0070 (9)	0.0046 (10)	0.0082 (9)
C2	0.0369 (11)	0.0402 (9)	0.0438 (9)	0.0012 (8)	0.0017 (8)	−0.0035 (7)
C3	0.0446 (12)	0.0445 (10)	0.0426 (9)	−0.0046 (8)	−0.0061 (8)	0.0023 (8)
C4	0.0351 (10)	0.0382 (9)	0.0377 (8)	0.0008 (7)	0.0009 (7)	−0.0005 (7)
C5	0.0345 (10)	0.0374 (9)	0.0361 (8)	0.0010 (7)	0.0013 (7)	0.0012 (7)
C6	0.0413 (12)	0.0424 (10)	0.0378 (8)	−0.0047 (8)	−0.0006 (8)	0.0023 (7)
C7	0.0405 (11)	0.0370 (9)	0.0351 (8)	0.0000 (7)	0.0058 (7)	−0.0003 (7)
C8	0.0433 (12)	0.0427 (10)	0.0431 (9)	−0.0045 (8)	0.0018 (8)	−0.0004 (7)
C9	0.0503 (13)	0.0523 (11)	0.0417 (9)	−0.0012 (9)	−0.0061 (9)	0.0032 (8)
C10	0.0554 (14)	0.0451 (10)	0.0389 (9)	0.0026 (9)	0.0037 (9)	0.0055 (8)
C11	0.0492 (12)	0.0344 (9)	0.0380 (8)	−0.0025 (8)	0.0087 (8)	−0.0026 (7)
C12	0.0452 (11)	0.0407 (9)	0.0335 (8)	−0.0032 (8)	0.0023 (8)	−0.0013 (7)
N1	0.0526 (11)	0.0535 (10)	0.0494 (9)	−0.0058 (8)	−0.0108 (8)	0.0045 (7)
N2	0.0383 (9)	0.0419 (8)	0.0369 (7)	−0.0062 (7)	−0.0052 (7)	0.0070 (6)
N3	0.0408 (9)	0.0392 (8)	0.0361 (7)	−0.0012 (7)	0.0005 (6)	0.0045 (6)
N4	0.0657 (13)	0.0404 (9)	0.0448 (8)	−0.0076 (8)	0.0105 (8)	−0.0011 (7)
O1	0.0437 (9)	0.0487 (7)	0.0558 (8)	−0.0099 (6)	−0.0047 (6)	−0.0022 (6)
O2	0.0435 (8)	0.0460 (7)	0.0436 (6)	−0.0060 (6)	−0.0065 (6)	0.0122 (5)
O3	0.1020 (15)	0.0733 (11)	0.0575 (9)	−0.0453 (10)	−0.0124 (9)	0.0048 (8)
O4	0.0948 (14)	0.0547 (9)	0.0567 (8)	−0.0164 (8)	0.0131 (8)	0.0157 (7)

C1—C2	1.476 (2)	C7—C8	1.401 (2)
C1—H1A	0.9600	C8—C9	1.376 (3)
C1—H1B	0.9600	C8—H8	0.9300
C1—H1C	0.9600	C9—C10	1.381 (3)
C2—O1	1.344 (2)	C9—H9	0.9300
C2—C4	1.356 (3)	C10—C11	1.379 (3)
C3—N1	1.292 (2)	C10—H10	0.9300
C3—C4	1.426 (2)	C11—C12	1.377 (2)
C3—H3A	0.9300	C11—N4	1.468 (2)
C4—C5	1.469 (2)	C12—H12	0.9300
C5—O2	1.2394 (19)	N1—O1	1.417 (2)
C5—N2	1.344 (2)	N2—N3	1.3714 (19)
C6—N3	1.274 (2)	N2—H2	0.901 (10)
C6—C7	1.457 (2)	N4—O4	1.213 (2)
C6—H6	0.9300	N4—O3	1.217 (2)
C7—C12	1.386 (2)
C2—C1—H1A	109.5	C9—C8—C7	120.61 (18)
C2—C1—H1B	109.5	C9—C8—H8	119.7
H1A—C1—H1B	109.5	C7—C8—H8	119.7
C2—C1—H1C	109.5	C8—C9—C10	120.63 (17)
H1A—C1—H1C	109.5	C8—C9—H9	119.7
H1B—C1—H1C	109.5	C10—C9—H9	119.7
O1—C2—C4	109.83 (15)	C11—C10—C9	118.12 (16)
O1—C2—C1	115.04 (16)	C11—C10—H10	120.9
C4—C2—C1	135.13 (16)	C9—C10—H10	120.9
N1—C3—C4	113.03 (17)	C12—C11—C10	122.69 (17)
N1—C3—H3A	123.5	C12—C11—N4	118.03 (16)
C4—C3—H3A	123.5	C10—C11—N4	119.27 (15)
C2—C4—C3	103.39 (15)	C11—C12—C7	118.94 (16)
C2—C4—C5	123.58 (15)	C11—C12—H12	120.5
C3—C4—C5	133.03 (16)	C7—C12—H12	120.5
O2—C5—N2	117.65 (15)	C3—N1—O1	104.65 (14)
O2—C5—C4	120.52 (16)	C5—N2—N3	124.32 (14)
N2—C5—C4	121.83 (14)	C5—N2—H2	117.0 (13)
N3—C6—C7	122.18 (16)	N3—N2—H2	118.7 (13)
N3—C6—H6	118.9	C6—N3—N2	114.20 (14)
C7—C6—H6	118.9	O4—N4—O3	122.94 (17)
C12—C7—C8	119.00 (15)	O4—N4—C11	118.53 (16)
C12—C7—C6	118.04 (15)	O3—N4—C11	118.53 (15)
C8—C7—C6	122.94 (16)	C2—O1—N1	109.09 (14)
O1—C2—C4—C3	−0.7 (2)	C9—C10—C11—N4	179.80 (18)
C1—C2—C4—C3	179.0 (2)	C10—C11—C12—C7	0.4 (3)
O1—C2—C4—C5	179.85 (17)	N4—C11—C12—C7	−179.30 (17)
C1—C2—C4—C5	−0.5 (4)	C8—C7—C12—C11	−0.9 (3)
N1—C3—C4—C2	0.5 (2)	C6—C7—C12—C11	177.65 (17)
N1—C3—C4—C5	179.9 (2)	C4—C3—N1—O1	−0.1 (2)
C2—C4—C5—O2	2.7 (3)	O2—C5—N2—N3	−179.10 (16)
C3—C4—C5—O2	−176.56 (19)	C4—C5—N2—N3	0.6 (3)
C2—C4—C5—N2	−176.99 (18)	C7—C6—N3—N2	178.84 (16)
C3—C4—C5—N2	3.7 (3)	C5—N2—N3—C6	−177.51 (18)
N3—C6—C7—C12	178.03 (18)	C12—C11—N4—O4	172.21 (18)
N3—C6—C7—C8	−3.5 (3)	C10—C11—N4—O4	−7.5 (3)
C12—C7—C8—C9	0.9 (3)	C12—C11—N4—O3	−7.9 (3)
C6—C7—C8—C9	−177.58 (19)	C10—C11—N4—O3	172.4 (2)
C7—C8—C9—C10	−0.4 (3)	C4—C2—O1—N1	0.6 (2)
C8—C9—C10—C11	−0.1 (3)	C1—C2—O1—N1	−179.08 (16)
C9—C10—C11—C12	0.1 (3)	C3—N1—O1—C2	−0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···N3	0.93	2.43	2.930 (2)	114
C12—H12···O4i	0.93	2.58	3.240 (2)	128
N2—H2···O2ii	0.90 (1)	1.95 (1)	2.855 (2)	179 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯N3	0.93	2.43	2.930 (2)	114
C12—H12⋯O4i	0.93	2.58	3.240 (2)	128
N2—H2⋯O2ii	0.90 (1)	1.95 (1)	2.855 (2)	179 (1)

Symmetry codes: (i) ; (ii) .