2-Hydr­oxy-N′-[1-(3-methyl­pyrazin-2-yl)ethyl­idene]benzohydrazide

Xi-Shi, T.; Yi-Min, F.

doi:10.1107/S1600536808006697

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o707

doi:10.1107/S1600536808006697

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2-Hydroxy-N′-[1-(3-methylpyrazin-2-yl)ethylidene]benzohydrazide

Tai Xi-Shi ^a and Feng Yi-Min ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: taixishi@lzu.edu.cn

(Received 10 March 2008; accepted 10 March 2008; online 14 March 2008)

The molecule of the title compound, C₁₄H₁₄N₄O₂, is slightly twisted, with a dihedral angle of 10.06 (14)° between the aromatic rings. An intramolecular N—H⋯O and an intermolecular O—H⋯O hydrogen bond help to establish the crystal structure.

Related literature

For related literature, see: Tai et al. (2003 ).

Experimental

Crystal data

C₁₄H₁₄N₄O₂
M_r = 270.29
Orthorhombic, P b c n
a = 12.6326 (14) Å
b = 9.3346 (10) Å
c = 22.119 (3) Å
V = 2608.3 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.49 × 0.43 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.954, T_max = 0.979
12690 measured reflections
2303 independent reflections
1380 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.156
S = 1.07
2303 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.20 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
N1—H1⋯O2	0.86	1.95	2.624 (3)	134
O2—H2⋯O1ⁱ	0.82	1.82	2.631 (3)	168
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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/S1600536808006697/hb2708sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808006697/hb2708Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of the chemistry of aroylhydrazone ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

The molecule is slightly twisted, with a dihedral angle of 10.06 (14)° between the aromatic rings. An intramolecular N—H···O and an intermolecular O—H···O hydrogen bond help to establish the structure (Table 1).

Related literature top

For related literature, see: Tai et al. (2003).

Experimental top

10 mmol of 2-acetyl-3-methylpyrazine (10 mmol) was added to a solution of salicyloyl hydrazine (10 mmol) in 10 ml of ethanol. The mixture was continuously stirred for 3 h at refluxing temperature, evaporating some ethanol. Upon cooling, the solid product was collected by filtration and dried in vacuo (yield 62%). Colourless blocks of (I) were obtained by evaporation from a methanol solution after one week.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (I) showing 50% displacement ellipsoids. The hydrogen bond is indicated by a double-dashed line.

2-Hydroxy-N'-[1-(3-methylpyrazin-2-yl)ethylidene]benzohydrazide top

Crystal data top

C₁₄H₁₄N₄O₂	F(000) = 1136
M_r = 270.29	D_x = 1.377 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2332 reflections
a = 12.6326 (14) Å	θ = 2.5–23.7°
b = 9.3346 (10) Å	µ = 0.10 mm⁻¹
c = 22.119 (3) Å	T = 298 K
V = 2608.3 (5) Å³	Block, colourless
Z = 8	0.49 × 0.43 × 0.22 mm

Data collection top

Bruker SMART CCD diffractometer	2303 independent reflections
Radiation source: fine-focus sealed tube	1380 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −15→13
T_min = 0.954, T_max = 0.979	k = −11→10
12690 measured reflections	l = −26→24

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0649P)² + 1.2514P] where P = (F_o² + 2F_c²)/3
2303 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₄H₁₄N₄O₂	V = 2608.3 (5) Å³
M_r = 270.29	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 12.6326 (14) Å	µ = 0.10 mm⁻¹
b = 9.3346 (10) Å	T = 298 K
c = 22.119 (3) Å	0.49 × 0.43 × 0.22 mm

Data collection top

Bruker SMART CCD diffractometer	2303 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1380 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.979	R_int = 0.052
12690 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.07	Δρ_max = 0.20 e Å⁻³
2303 reflections	Δρ_min = −0.17 e Å⁻³
181 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
N1	0.79886 (17)	0.1654 (2)	0.42259 (10)	0.0408 (6)
H1	0.8658	0.1773	0.4278	0.049*
N2	0.76327 (17)	0.0717 (2)	0.37945 (10)	0.0396 (6)
N3	0.8738 (2)	−0.1605 (3)	0.27123 (12)	0.0590 (8)
N4	0.6645 (2)	−0.2165 (3)	0.24385 (12)	0.0586 (8)
O1	0.63328 (14)	0.2289 (2)	0.44838 (9)	0.0553 (6)
O2	0.95222 (14)	0.2544 (2)	0.49322 (9)	0.0574 (6)
H2	1.0112	0.2679	0.5076	0.086*
C1	0.7298 (2)	0.2386 (3)	0.45667 (12)	0.0379 (7)
C2	0.77414 (19)	0.3353 (3)	0.50398 (11)	0.0356 (6)
C3	0.8809 (2)	0.3424 (3)	0.52082 (12)	0.0401 (7)
C4	0.9125 (2)	0.4359 (3)	0.56555 (13)	0.0478 (8)
H4	0.9834	0.4394	0.5767	0.057*
C5	0.8411 (2)	0.5234 (3)	0.59369 (13)	0.0498 (8)
H5	0.8638	0.5865	0.6235	0.060*
C6	0.7359 (2)	0.5186 (3)	0.57807 (13)	0.0465 (8)
H6	0.6872	0.5779	0.5973	0.056*
C7	0.7034 (2)	0.4253 (3)	0.53383 (12)	0.0425 (7)
H7	0.6321	0.4221	0.5235	0.051*
C8	0.9508 (2)	0.0190 (4)	0.35800 (17)	0.0733 (11)
H8A	0.9701	0.1181	0.3542	0.110*
H8B	0.9873	−0.0360	0.3278	0.110*
H8C	0.9701	−0.0150	0.3975	0.110*
C9	0.8340 (2)	0.0033 (3)	0.34940 (13)	0.0426 (7)
C10	0.7959 (2)	−0.0970 (3)	0.30201 (12)	0.0409 (7)
C11	0.6890 (2)	−0.1265 (3)	0.28871 (12)	0.0428 (7)
C12	0.5955 (2)	−0.0662 (4)	0.32156 (14)	0.0568 (9)
H12A	0.5317	−0.1066	0.3053	0.085*
H12B	0.5941	0.0360	0.3167	0.085*
H12C	0.6007	−0.0892	0.3638	0.085*
C13	0.7439 (3)	−0.2763 (4)	0.21323 (15)	0.0627 (9)
H13	0.7283	−0.3383	0.1815	0.075*
C14	0.8469 (3)	−0.2494 (4)	0.22696 (15)	0.0639 (10)
H14	0.8998	−0.2945	0.2048	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0318 (12)	0.0478 (15)	0.0428 (14)	−0.0032 (11)	−0.0015 (10)	−0.0074 (12)
N2	0.0381 (13)	0.0423 (14)	0.0382 (13)	−0.0022 (11)	0.0012 (10)	−0.0040 (11)
N3	0.0574 (17)	0.0631 (18)	0.0565 (17)	0.0068 (14)	0.0117 (13)	−0.0102 (15)
N4	0.0638 (18)	0.0608 (18)	0.0510 (16)	0.0056 (15)	−0.0092 (13)	−0.0135 (14)
O1	0.0312 (11)	0.0761 (16)	0.0585 (13)	−0.0021 (10)	−0.0003 (9)	−0.0172 (12)
O2	0.0328 (11)	0.0712 (15)	0.0684 (14)	0.0027 (10)	−0.0054 (9)	−0.0268 (12)
C1	0.0308 (15)	0.0439 (18)	0.0389 (15)	0.0007 (13)	0.0035 (12)	0.0038 (13)
C2	0.0336 (15)	0.0361 (16)	0.0372 (15)	−0.0018 (12)	0.0008 (11)	0.0032 (13)
C3	0.0343 (15)	0.0423 (17)	0.0437 (16)	−0.0006 (13)	0.0029 (12)	−0.0033 (14)
C4	0.0374 (16)	0.0539 (19)	0.0522 (18)	−0.0010 (15)	−0.0050 (13)	−0.0084 (16)
C5	0.0552 (19)	0.0469 (19)	0.0473 (17)	−0.0040 (15)	−0.0003 (15)	−0.0080 (15)
C6	0.0506 (18)	0.0431 (18)	0.0459 (17)	0.0047 (14)	0.0040 (14)	−0.0008 (14)
C7	0.0385 (15)	0.0449 (18)	0.0440 (16)	0.0039 (14)	0.0017 (13)	0.0027 (15)
C8	0.0386 (18)	0.087 (3)	0.094 (3)	0.0031 (18)	0.0004 (17)	−0.033 (2)
C9	0.0359 (15)	0.0455 (18)	0.0464 (17)	0.0021 (14)	0.0031 (13)	0.0001 (14)
C10	0.0453 (17)	0.0388 (17)	0.0386 (15)	0.0063 (13)	0.0041 (13)	0.0013 (13)
C11	0.0474 (17)	0.0437 (18)	0.0374 (16)	0.0061 (14)	−0.0021 (13)	0.0019 (14)
C12	0.0408 (17)	0.072 (2)	0.0576 (19)	0.0035 (16)	−0.0044 (14)	−0.0143 (17)
C13	0.078 (2)	0.061 (2)	0.0490 (19)	0.011 (2)	−0.0054 (18)	−0.0167 (17)
C14	0.068 (2)	0.069 (2)	0.055 (2)	0.013 (2)	0.0114 (17)	−0.0118 (19)

Geometric parameters (Å, º) top

N1—C1	1.340 (3)	C5—H5	0.9300
N1—N2	1.370 (3)	C6—C7	1.373 (4)
N1—H1	0.8600	C6—H6	0.9300
N2—C9	1.284 (3)	C7—H7	0.9300
N3—C14	1.328 (4)	C8—C9	1.495 (4)
N3—C10	1.335 (3)	C8—H8A	0.9600
N4—C13	1.332 (4)	C8—H8B	0.9600
N4—C11	1.336 (4)	C8—H8C	0.9600
O1—C1	1.236 (3)	C9—C10	1.485 (4)
O2—C3	1.364 (3)	C10—C11	1.409 (4)
O2—H2	0.8200	C11—C12	1.497 (4)
C1—C2	1.492 (4)	C12—H12A	0.9600
C2—C7	1.393 (4)	C12—H12B	0.9600
C2—C3	1.400 (3)	C12—H12C	0.9600
C3—C4	1.378 (4)	C13—C14	1.359 (5)
C4—C5	1.367 (4)	C13—H13	0.9300
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.374 (4)

C1—N1—N2	120.2 (2)	C9—C8—H8A	109.5
C1—N1—H1	119.9	C9—C8—H8B	109.5
N2—N1—H1	119.9	H8A—C8—H8B	109.5
C9—N2—N1	116.7 (2)	C9—C8—H8C	109.5
C14—N3—C10	117.7 (3)	H8A—C8—H8C	109.5
C13—N4—C11	117.8 (3)	H8B—C8—H8C	109.5
C3—O2—H2	109.5	N2—C9—C10	117.0 (2)
O1—C1—N1	121.5 (3)	N2—C9—C8	124.9 (3)
O1—C1—C2	121.2 (2)	C10—C9—C8	118.1 (2)
N1—C1—C2	117.3 (2)	N3—C10—C11	120.8 (3)
C7—C2—C3	117.6 (2)	N3—C10—C9	113.7 (3)
C7—C2—C1	117.2 (2)	C11—C10—C9	125.5 (2)
C3—C2—C1	125.2 (2)	N4—C11—C10	120.0 (3)
O2—C3—C4	120.7 (2)	N4—C11—C12	114.4 (3)
O2—C3—C2	119.3 (2)	C10—C11—C12	125.5 (3)
C4—C3—C2	120.0 (3)	C11—C12—H12A	109.5
C5—C4—C3	120.9 (3)	C11—C12—H12B	109.5
C5—C4—H4	119.6	H12A—C12—H12B	109.5
C3—C4—H4	119.6	C11—C12—H12C	109.5
C4—C5—C6	120.3 (3)	H12A—C12—H12C	109.5
C4—C5—H5	119.9	H12B—C12—H12C	109.5
C6—C5—H5	119.9	N4—C13—C14	121.9 (3)
C7—C6—C5	119.3 (3)	N4—C13—H13	119.0
C7—C6—H6	120.3	C14—C13—H13	119.0
C5—C6—H6	120.3	N3—C14—C13	121.7 (3)
C6—C7—C2	121.9 (3)	N3—C14—H14	119.2
C6—C7—H7	119.1	C13—C14—H14	119.2
C2—C7—H7	119.1

C1—N1—N2—C9	−178.6 (3)	N1—N2—C9—C10	−179.2 (2)
N2—N1—C1—O1	−3.4 (4)	N1—N2—C9—C8	−0.2 (4)
N2—N1—C1—C2	178.2 (2)	C14—N3—C10—C11	1.6 (4)
O1—C1—C2—C7	−6.7 (4)	C14—N3—C10—C9	−178.4 (3)
N1—C1—C2—C7	171.7 (2)	N2—C9—C10—N3	177.8 (3)
O1—C1—C2—C3	173.1 (3)	C8—C9—C10—N3	−1.3 (4)
N1—C1—C2—C3	−8.6 (4)	N2—C9—C10—C11	−2.2 (4)
C7—C2—C3—O2	179.0 (2)	C8—C9—C10—C11	178.7 (3)
C1—C2—C3—O2	−0.7 (4)	C13—N4—C11—C10	0.4 (4)
C7—C2—C3—C4	0.1 (4)	C13—N4—C11—C12	−178.9 (3)
C1—C2—C3—C4	−179.6 (3)	N3—C10—C11—N4	−1.6 (4)
O2—C3—C4—C5	−179.4 (3)	C9—C10—C11—N4	178.4 (3)
C2—C3—C4—C5	−0.6 (4)	N3—C10—C11—C12	177.6 (3)
C3—C4—C5—C6	0.6 (5)	C9—C10—C11—C12	−2.4 (5)
C4—C5—C6—C7	−0.2 (4)	C11—N4—C13—C14	0.8 (5)
C5—C6—C7—C2	−0.2 (4)	C10—N3—C14—C13	−0.4 (5)
C3—C2—C7—C6	0.3 (4)	N4—C13—C14—N3	−0.9 (6)
C1—C2—C7—C6	−180.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.95	2.624 (3)	134
O2—H2···O1ⁱ	0.82	1.82	2.631 (3)	168

Symmetry code: (i) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₄O₂
M_r	270.29
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	12.6326 (14), 9.3346 (10), 22.119 (3)
V (Å³)	2608.3 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.49 × 0.43 × 0.22

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.954, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	12690, 2303, 1380
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.156, 1.07
No. of reflections	2303
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.17

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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
N1—H1···O2	0.86	1.95	2.624 (3)	134
O2—H2···O1ⁱ	0.82	1.82	2.631 (3)	168

Symmetry code: (i) x+1/2, −y+1/2, −z+1.

Acknowledgements

The authors thank the National Natural Science Foundation of China (20671073), the National Natural Science Foundation of Shandong, the Science and Technology Foundation of Weifang and Weifang University for research grants.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tai, X.-S., Yin, X.-H., Tan, M.-Y. & Li, Y.-Z. (2003). Acta Cryst. E59, o681–o682. Web of Science CSD CrossRef IUCr Journals Google Scholar