2'-(3-Hydroxy-benzyl-idene)pyrazine-2-carbohydrazide monohydrate.

The title compound, C(12)H(10)N(4)O(2)·H(2)O, was synthesized by the reaction of pyrazine-2-carboxylic acid hydrazide and 3-hydroxy-benzaldehyde in ethanol. In the crystal structure, the organic mol-ecules are linked into extended chains by inter-molecular N(amide)-H⋯O(hydr-oxy) hydrogen bonds. Additional hydrogen bonds between the water mol-ecule and three adjacent organic mol-ecules, as well as face-to-face π-π stacking inter-actions between the benzene and pyrazine rings [centroid-to-centroid separation = 3.669 (2) Å and offset = 1.362 Å], link the mol-ecules into a three-dimensional framework.

Related literature

For pharmacological and photochromic properties of hydrazone­carbonyl compounds, see: Parashar et al. (1988 ▶); Hadjoudis et al. (1987 ▶). For related pyrazinecarboxylic acid hydrazones, see: Gardner et al. (1956 ▶);

Experimental

Crystal data

C12H10N4O2·H2O

M = 260.26

Triclinic,

a = 8.062 (3) Å

b = 8.186 (3) Å

c = 9.449 (3) Å

α = 95.122 (6)°

β = 103.169 (6)°

γ = 99.827 (7)°

V = 592.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 294 (2) K

0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.962, T max = 0.981

3017 measured reflections

2083 independent reflections

1112 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.140

S = 1.02

2083 reflections

184 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807062708/ln2011sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062708/ln2011Isup2.hkl

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

C12H10N4O2·H2O	Z = 2
Mr = 260.26	F000 = 272
Triclinic, P1	Dx = 1.458 Mg m−3
a = 8.062 (3) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.186 (3) Å	Cell parameters from 658 reflections
c = 9.449 (3) Å	θ = 2.2–23.0º
α = 95.122 (6)º	µ = 0.11 mm−1
β = 103.169 (6)º	T = 294 (2) K
γ = 99.827 (7)º	Block, colourless
V = 592.9 (4) Å3	0.24 × 0.22 × 0.18 mm

Bruker CCD area-detector diffractometer	2083 independent reflections
Radiation source: fine-focus sealed tube	1112 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 294(2) K	θmax = 25.0º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.962, Tmax = 0.981	k = −9→4
3017 measured reflections	l = −10→11

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0631P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2083 reflections	Δρmax = 0.20 e Å−3
184 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.4727 (3)	0.5725 (3)	0.7739 (2)	0.0587 (7)
O2	0.0678 (3)	1.0884 (3)	0.3575 (3)	0.0567 (7)
H2	−0.014 (5)	1.134 (5)	0.314 (4)	0.085*
N1	0.4525 (3)	0.1480 (3)	0.6449 (2)	0.0392 (7)
N2	0.6326 (3)	0.1543 (3)	0.9355 (3)	0.0472 (7)
N3	0.3179 (4)	0.4148 (3)	0.5600 (3)	0.0397 (7)
H3	0.299 (4)	0.322 (4)	0.513 (3)	0.048*
N4	0.2524 (3)	0.5480 (3)	0.5068 (3)	0.0402 (7)
C1	0.5113 (4)	0.0166 (4)	0.6931 (3)	0.0448 (9)
H1	0.4921	−0.0808	0.6281	0.054*
C2	0.6005 (4)	0.0195 (4)	0.8370 (3)	0.0465 (9)
H2A	0.6393	−0.0760	0.8658	0.056*
C3	0.5740 (4)	0.2865 (4)	0.8871 (3)	0.0444 (8)
H3A	0.5930	0.3836	0.9525	0.053*
C4	0.4858 (4)	0.2849 (4)	0.7429 (3)	0.0337 (7)
C5	0.4252 (4)	0.4375 (4)	0.6954 (3)	0.0398 (8)
C6	0.1605 (4)	0.5199 (4)	0.3753 (3)	0.0388 (8)
H6	0.1440	0.4139	0.3235	0.047*
C7	0.0801 (4)	0.6459 (4)	0.3024 (3)	0.0355 (8)
C8	−0.0298 (4)	0.5994 (4)	0.1629 (3)	0.0434 (9)
H8	−0.0512	0.4892	0.1188	0.052*
C9	−0.1069 (4)	0.7147 (4)	0.0899 (3)	0.0501 (9)
H9	−0.1803	0.6823	−0.0034	0.060*
C10	−0.0764 (4)	0.8785 (4)	0.1537 (3)	0.0450 (9)
H10	−0.1286	0.9565	0.1035	0.054*
C11	0.0317 (4)	0.9261 (4)	0.2922 (3)	0.0378 (8)
C12	0.1093 (4)	0.8114 (4)	0.3664 (3)	0.0385 (8)
H12	0.1818	0.8444	0.4600	0.046*
O3	0.1948 (3)	0.7733 (3)	0.7579 (2)	0.0590 (7)
H3B	0.242 (5)	0.816 (4)	0.847 (3)	0.088*
H3C	0.246 (5)	0.708 (4)	0.708 (4)	0.088*

	U11	U22	U33	U12	U13	U23
O1	0.0769 (18)	0.0433 (15)	0.0455 (14)	0.0237 (13)	−0.0117 (13)	−0.0016 (12)
O2	0.0651 (17)	0.0367 (14)	0.0564 (15)	0.0197 (12)	−0.0147 (12)	0.0016 (11)
N1	0.0441 (16)	0.0446 (17)	0.0289 (14)	0.0186 (14)	0.0008 (12)	0.0061 (13)
N2	0.0529 (18)	0.0528 (19)	0.0355 (16)	0.0205 (15)	−0.0003 (13)	0.0138 (14)
N3	0.0492 (17)	0.0342 (16)	0.0355 (16)	0.0202 (15)	0.0004 (13)	0.0076 (12)
N4	0.0455 (16)	0.0401 (16)	0.0378 (16)	0.0203 (14)	0.0037 (13)	0.0139 (13)
C1	0.055 (2)	0.044 (2)	0.0365 (19)	0.0190 (18)	0.0060 (16)	0.0072 (16)
C2	0.055 (2)	0.048 (2)	0.040 (2)	0.0218 (19)	0.0064 (17)	0.0158 (17)
C3	0.051 (2)	0.045 (2)	0.0348 (19)	0.0150 (17)	0.0024 (16)	0.0059 (16)
C4	0.0332 (17)	0.0430 (19)	0.0275 (17)	0.0159 (15)	0.0051 (14)	0.0083 (15)
C5	0.0407 (19)	0.046 (2)	0.0343 (19)	0.0171 (17)	0.0045 (16)	0.0085 (17)
C6	0.047 (2)	0.0365 (19)	0.0335 (19)	0.0132 (16)	0.0068 (16)	0.0080 (14)
C7	0.0358 (18)	0.0397 (19)	0.0338 (18)	0.0164 (16)	0.0049 (15)	0.0120 (15)
C8	0.056 (2)	0.0376 (19)	0.0332 (19)	0.0139 (17)	0.0012 (16)	0.0039 (15)
C9	0.063 (2)	0.051 (2)	0.0303 (18)	0.0224 (19)	−0.0075 (16)	0.0037 (16)
C10	0.051 (2)	0.047 (2)	0.0360 (19)	0.0238 (18)	−0.0039 (16)	0.0116 (16)
C11	0.0393 (19)	0.0331 (19)	0.0390 (19)	0.0111 (16)	0.0025 (15)	0.0059 (15)
C12	0.0388 (19)	0.042 (2)	0.0324 (18)	0.0129 (16)	−0.0016 (15)	0.0079 (15)
O3	0.0716 (18)	0.0561 (17)	0.0466 (15)	0.0334 (14)	−0.0036 (13)	0.0000 (13)

O1—C5	1.224 (4)	C4—C5	1.486 (4)
O2—C11	1.368 (4)	C6—C7	1.453 (4)
O2—H2	0.86 (4)	C6—H6	0.9300
N1—C1	1.324 (4)	C7—C8	1.390 (4)
N1—C4	1.336 (3)	C7—C12	1.391 (4)
N2—C2	1.327 (4)	C8—C9	1.369 (4)
N2—C3	1.330 (4)	C8—H8	0.9300
N3—C5	1.348 (4)	C9—C10	1.377 (4)
N3—N4	1.376 (3)	C9—H9	0.9300
N3—H3	0.82 (3)	C10—C11	1.377 (4)
N4—C6	1.272 (3)	C10—H10	0.9300
C1—C2	1.382 (4)	C11—C12	1.373 (4)
C1—H1	0.9300	C12—H12	0.9300
C2—H2A	0.9300	O3—H3B	0.86 (2)
C3—C4	1.384 (4)	O3—H3C	0.89 (2)
C3—H3A	0.9300
C11—O2—H2	106 (3)	N4—C6—C7	122.9 (3)
C1—N1—C4	116.3 (3)	N4—C6—H6	118.5
C2—N2—C3	115.9 (3)	C7—C6—H6	118.5
C5—N3—N4	119.2 (3)	C8—C7—C12	118.7 (3)
C5—N3—H3	117 (2)	C8—C7—C6	118.7 (3)
N4—N3—H3	124 (2)	C12—C7—C6	122.6 (3)
C6—N4—N3	115.7 (3)	C9—C8—C7	120.5 (3)
N1—C1—C2	122.1 (3)	C9—C8—H8	119.8
N1—C1—H1	118.9	C7—C8—H8	119.8
C2—C1—H1	118.9	C8—C9—C10	120.4 (3)
N2—C2—C1	122.1 (3)	C8—C9—H9	119.8
N2—C2—H2A	119.0	C10—C9—H9	119.8
C1—C2—H2A	119.0	C9—C10—C11	119.7 (3)
N2—C3—C4	122.4 (3)	C9—C10—H10	120.1
N2—C3—H3A	118.8	C11—C10—H10	120.1
C4—C3—H3A	118.8	O2—C11—C12	118.5 (3)
N1—C4—C3	121.3 (3)	O2—C11—C10	121.2 (3)
N1—C4—C5	119.0 (3)	C12—C11—C10	120.3 (3)
C3—C4—C5	119.7 (3)	C11—C12—C7	120.4 (3)
O1—C5—N3	123.6 (3)	C11—C12—H12	119.8
O1—C5—C4	121.7 (3)	C7—C12—H12	119.8
N3—C5—C4	114.7 (3)	H3B—O3—H3C	122 (4)
C5—N3—N4—C6	176.0 (3)	C3—C4—C5—N3	−170.0 (3)
C4—N1—C1—C2	0.8 (4)	N3—N4—C6—C7	179.4 (3)
C3—N2—C2—C1	−0.2 (5)	N4—C6—C7—C8	−174.7 (3)
N1—C1—C2—N2	0.0 (5)	N4—C6—C7—C12	5.6 (5)
C2—N2—C3—C4	−0.3 (5)	C12—C7—C8—C9	0.3 (4)
C1—N1—C4—C3	−1.3 (4)	C6—C7—C8—C9	−179.4 (3)
C1—N1—C4—C5	179.2 (3)	C7—C8—C9—C10	0.0 (5)
N2—C3—C4—N1	1.1 (5)	C8—C9—C10—C11	−0.3 (5)
N2—C3—C4—C5	−179.4 (3)	C9—C10—C11—O2	178.6 (3)
N4—N3—C5—O1	−2.0 (5)	C9—C10—C11—C12	0.2 (5)
N4—N3—C5—C4	179.0 (3)	O2—C11—C12—C7	−178.2 (3)
N1—C4—C5—O1	−169.5 (3)	C10—C11—C12—C7	0.2 (5)
C3—C4—C5—O1	11.0 (5)	C8—C7—C12—C11	−0.5 (4)
N1—C4—C5—N3	9.5 (4)	C6—C7—C12—C11	179.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.86 (4)	1.78 (4)	2.634 (3)	174 (4)
N3—H3···N1	0.82 (3)	2.31 (3)	2.705 (3)	110 (3)
N3—H3···O2ii	0.82 (3)	2.51 (3)	3.218 (4)	145 (3)
O3—H3B···N2iii	0.86 (2)	2.04 (3)	2.873 (3)	163 (4)
O3—H3C···N4	0.89 (2)	2.22 (3)	3.043 (3)	152 (3)
O3—H3C···O1	0.89 (2)	2.29 (3)	2.982 (3)	134 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.86 (4)	1.78 (4)	2.634 (3)	174 (4)
N3—H3⋯N1	0.82 (3)	2.31 (3)	2.705 (3)	110 (3)
N3—H3⋯O2ii	0.82 (3)	2.51 (3)	3.218 (4)	145 (3)
O3—H3B⋯N2iii	0.86 (2)	2.04 (3)	2.873 (3)	163 (4)
O3—H3C⋯N4	0.89 (2)	2.22 (3)	3.043 (3)	152 (3)
O3—H3C⋯O1	0.89 (2)	2.29 (3)	2.982 (3)	134 (3)

Symmetry codes: (i) ; (ii) ; (iii) .