N'-(4-Cyano-benzyl-idene)furan-2-carbohydrazide monohydrate.

In the title compound, C(13)H(9)N(3)O(2)·H(2)O, the dihedral angle between the aromatic rings is 10.7 (4)° and an intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, the components are linked by N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds.

Related literature

For a related structure and background references, see: Li et al. (2010 ▶).

Experimental

Crystal data

C13H9N3O2·H2O

M = 257.25

Monoclinic,

a = 7.0501 (14) Å

b = 14.295 (3) Å

c = 12.640 (3) Å

β = 103.38 (3)°

V = 1239.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

11389 measured reflections

2834 independent reflections

1568 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.135

S = 0.98

2834 reflections

180 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022221/hb5490sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022221/hb5490Isup2.hkl

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

C13H9N3O2·H2O	F(000) = 536
Mr = 257.25	Dx = 1.379 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1568 reflections
a = 7.0501 (14) Å	θ = 2.7–25.5°
b = 14.295 (3) Å	µ = 0.10 mm−1
c = 12.640 (3) Å	T = 293 K
β = 103.38 (3)°	Block, colorless
V = 1239.3 (4) Å3	0.22 × 0.20 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	1568 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
graphite	θmax = 27.5°, θmin = 3.3°
φ and ω scans	h = −8→9
11389 measured reflections	k = −18→18
2834 independent reflections	l = −16→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0694P)2] where P = (Fo2 + 2Fc2)/3
2834 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.16 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
N2	0.2572 (2)	0.42473 (10)	0.51829 (12)	0.0431 (4)
N1	0.2142 (2)	0.34390 (9)	0.45997 (12)	0.0440 (4)
H1A	0.1704	0.3458	0.3906	0.053*
O1	0.10154 (18)	0.19128 (9)	0.33670 (10)	0.0526 (4)
C6	0.2239 (3)	0.50009 (12)	0.46228 (15)	0.0461 (5)
H6A	0.1747	0.4964	0.3875	0.055*
C4	0.1844 (3)	0.17816 (13)	0.44486 (15)	0.0442 (5)
O3	0.0883 (2)	0.37589 (11)	0.22607 (12)	0.0654 (5)
C13	0.3865 (3)	0.85907 (14)	0.65549 (17)	0.0548 (5)
O2	0.3075 (2)	0.25365 (9)	0.61179 (11)	0.0595 (4)
C12	0.3138 (3)	0.60216 (13)	0.62661 (16)	0.0525 (5)
H12A	0.3218	0.5497	0.6709	0.063*
C7	0.2620 (3)	0.59186 (12)	0.51417 (15)	0.0420 (4)
C5	0.2414 (3)	0.26093 (12)	0.51272 (15)	0.0436 (4)
C8	0.2453 (3)	0.67132 (13)	0.44979 (16)	0.0518 (5)
H8A	0.2069	0.6655	0.3746	0.062*
C11	0.3534 (3)	0.68908 (13)	0.67294 (16)	0.0551 (5)
H11A	0.3887	0.6952	0.7482	0.066*
C10	0.3405 (3)	0.76786 (12)	0.60708 (16)	0.0453 (5)
C2	0.0589 (3)	0.10477 (13)	0.29261 (18)	0.0566 (6)
H2B	0.0003	0.0931	0.2200	0.068*
N3	0.4234 (3)	0.93164 (12)	0.69148 (17)	0.0721 (6)
C1	0.1133 (3)	0.03943 (15)	0.36854 (18)	0.0654 (6)
H1B	0.1006	−0.0249	0.3588	0.078*
C9	0.2850 (3)	0.75903 (13)	0.49571 (16)	0.0521 (5)
H9A	0.2741	0.8118	0.4516	0.062*
C3	0.1943 (3)	0.08674 (13)	0.46686 (18)	0.0617 (6)
H3A	0.2449	0.0593	0.5342	0.074*
H3B	0.025 (5)	0.438 (3)	0.208 (3)	0.156 (14)*
H3C	−0.005 (4)	0.337 (2)	0.197 (3)	0.120 (12)*

	U11	U22	U33	U12	U13	U23
N2	0.0504 (9)	0.0360 (8)	0.0404 (9)	0.0034 (7)	0.0056 (7)	−0.0056 (7)
N1	0.0572 (9)	0.0360 (8)	0.0346 (9)	0.0018 (7)	0.0023 (7)	−0.0016 (6)
O1	0.0708 (9)	0.0435 (7)	0.0389 (8)	−0.0040 (7)	0.0030 (6)	0.0018 (6)
C6	0.0560 (11)	0.0405 (10)	0.0384 (11)	0.0028 (9)	0.0037 (8)	−0.0023 (8)
C4	0.0466 (10)	0.0473 (11)	0.0366 (11)	0.0005 (9)	0.0052 (8)	0.0017 (8)
O3	0.0897 (11)	0.0468 (9)	0.0497 (9)	−0.0047 (9)	−0.0044 (8)	0.0021 (7)
C13	0.0600 (12)	0.0438 (11)	0.0576 (13)	0.0031 (10)	0.0073 (10)	−0.0013 (10)
O2	0.0829 (10)	0.0532 (8)	0.0369 (8)	0.0059 (7)	0.0026 (7)	0.0064 (6)
C12	0.0739 (14)	0.0408 (10)	0.0418 (11)	0.0062 (10)	0.0114 (10)	0.0024 (8)
C7	0.0435 (10)	0.0381 (10)	0.0428 (11)	0.0050 (8)	0.0072 (8)	−0.0002 (8)
C5	0.0451 (10)	0.0468 (11)	0.0377 (11)	0.0064 (9)	0.0074 (8)	0.0064 (8)
C8	0.0653 (12)	0.0467 (11)	0.0392 (12)	0.0028 (9)	0.0038 (9)	−0.0003 (8)
C11	0.0768 (14)	0.0483 (11)	0.0369 (11)	0.0042 (10)	0.0064 (10)	−0.0036 (9)
C10	0.0469 (10)	0.0383 (10)	0.0490 (12)	0.0020 (8)	0.0077 (8)	−0.0048 (8)
C2	0.0708 (14)	0.0460 (11)	0.0488 (12)	−0.0087 (10)	0.0052 (10)	−0.0062 (9)
N3	0.0868 (14)	0.0448 (11)	0.0786 (14)	−0.0037 (10)	0.0064 (11)	−0.0129 (9)
C1	0.0812 (15)	0.0401 (11)	0.0656 (15)	−0.0037 (11)	−0.0021 (12)	−0.0018 (10)
C9	0.0625 (12)	0.0396 (10)	0.0513 (13)	0.0008 (9)	0.0075 (10)	0.0067 (9)
C3	0.0757 (14)	0.0430 (11)	0.0575 (14)	0.0020 (10)	−0.0030 (11)	0.0125 (9)

N2—C6	1.281 (2)	C12—C11	1.374 (3)
N2—N1	1.3664 (18)	C12—C7	1.391 (3)
N1—C5	1.352 (2)	C12—H12A	0.9300
N1—H1A	0.8600	C7—C8	1.386 (2)
O1—C2	1.361 (2)	C8—C9	1.383 (2)
O1—C4	1.370 (2)	C8—H8A	0.9300
C6—C7	1.464 (2)	C11—C10	1.391 (3)
C6—H6A	0.9300	C11—H11A	0.9300
C4—C3	1.335 (2)	C10—C9	1.377 (3)
C4—C5	1.462 (2)	C2—C1	1.331 (3)
O3—H3B	1.00 (4)	C2—H2B	0.9300
O3—H3C	0.87 (3)	C1—C3	1.414 (3)
C13—N3	1.139 (2)	C1—H1B	0.9300
C13—C10	1.445 (3)	C9—H9A	0.9300
O2—C5	1.235 (2)	C3—H3A	0.9300
C6—N2—N1	115.07 (15)	C9—C8—C7	121.00 (18)
C5—N1—N2	119.16 (15)	C9—C8—H8A	119.5
C5—N1—H1A	120.4	C7—C8—H8A	119.5
N2—N1—H1A	120.4	C12—C11—C10	119.89 (18)
C2—O1—C4	106.68 (15)	C12—C11—H11A	120.1
N2—C6—C7	121.01 (17)	C10—C11—H11A	120.1
N2—C6—H6A	119.5	C9—C10—C11	120.09 (17)
C7—C6—H6A	119.5	C9—C10—C13	119.90 (17)
C3—C4—O1	109.38 (16)	C11—C10—C13	120.01 (18)
C3—C4—C5	132.55 (18)	C1—C2—O1	110.06 (19)
O1—C4—C5	118.07 (15)	C1—C2—H2B	125.0
H3B—O3—H3C	102 (3)	O1—C2—H2B	125.0
N3—C13—C10	178.5 (2)	C2—C1—C3	106.77 (19)
C11—C12—C7	120.69 (17)	C2—C1—H1B	126.6
C11—C12—H12A	119.7	C3—C1—H1B	126.6
C7—C12—H12A	119.7	C10—C9—C8	119.63 (17)
C8—C7—C12	118.66 (16)	C10—C9—H9A	120.2
C8—C7—C6	119.31 (17)	C8—C9—H9A	120.2
C12—C7—C6	122.03 (16)	C4—C3—C1	107.11 (19)
O2—C5—N1	123.42 (16)	C4—C3—H3A	126.4
O2—C5—C4	120.96 (16)	C1—C3—H3A	126.4
N1—C5—C4	115.60 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.33	2.692 (2)	106
N1—H1A···O3	0.86	2.07	2.920 (2)	169
O3—H3B···N3i	1.00 (4)	1.99 (4)	2.980 (2)	172 (3)
O3—H3C···O2ii	0.88 (3)	1.98 (3)	2.848 (2)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	2.33	2.692 (2)	106
N1—H1A⋯O3	0.86	2.07	2.920 (2)	169
O3—H3B⋯N3i	1.00 (4)	1.99 (4)	2.980 (2)	172 (3)
O3—H3C⋯O2ii	0.88 (3)	1.98 (3)	2.848 (2)	171 (3)

Symmetry codes: (i) ; (ii) .