2-Cyano-N'-[1-(2-hy-droxy-phen-yl)ethyl-idene]acetohydrazide monohydrate.

The title compound, C(11)H(11)N(3)O(2)·H(2)O, was obtained by the reaction of 2-acetyl-phenol with cyano-acetohydrazide in methanol. The asymmetric unit contains two hydrazone mol-ecules and two water mol-ecules of crystallization. There is an intra-molecular O-H⋯N hydrogen bond in each hydrazone mol-ecule. The crystal structure is stabilized by inter-molecular N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds.

Related literature

For the structures of hydrazones, see: Wang et al. (2011 ▶); Hashemian et al. (2011 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶). For compounds we have reported on recently, see: Li & Ni (2011 ▶); Li & Chen (2011 ▶).

Experimental

Crystal data

C11H11N3O2·H2O

M = 235.24

Monoclinic,

a = 17.387 (3) Å

b = 7.576 (2) Å

c = 17.855 (3) Å

β = 90.962 (2)°

V = 2351.7 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.981, T max = 0.983

14877 measured reflections

4994 independent reflections

2551 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.147

S = 1.02

4994 reflections

329 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042565/qm2036sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042565/qm2036Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042565/qm2036Isup3.cml

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

C11H11N3O2·H2O	F(000) = 992
Mr = 235.24	Dx = 1.329 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 17.387 (3) Å	Cell parameters from 2383 reflections
b = 7.576 (2) Å	θ = 2.3–24.5°
c = 17.855 (3) Å	µ = 0.10 mm−1
β = 90.962 (2)°	T = 298 K
V = 2351.7 (8) Å3	Block, colorless
Z = 8	0.20 × 0.18 × 0.17 mm

Bruker SMART 1K CCD area-detector diffractometer	4994 independent reflections
Radiation source: fine-focus sealed tube	2551 reflections with I > 2σ(I)
graphite	Rint = 0.060
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −22→22
Tmin = 0.981, Tmax = 0.983	k = −9→9
14877 measured reflections	l = −22→21

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.2161P] where P = (Fo2 + 2Fc2)/3
4994 reflections	(Δ/σ)max < 0.001
329 parameters	Δρmax = 0.19 e Å−3
8 restraints	Δρmin = −0.18 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
N1	0.04236 (11)	0.8041 (3)	0.03832 (12)	0.0382 (5)
N2	0.11383 (11)	0.8825 (3)	0.04497 (12)	0.0384 (6)
N3	0.23967 (15)	1.1713 (4)	0.24440 (16)	0.0695 (8)
N4	0.52913 (12)	0.2797 (3)	1.02064 (12)	0.0413 (6)
N5	0.52601 (12)	0.3436 (3)	1.09279 (13)	0.0448 (6)
N6	0.7097 (2)	0.4674 (6)	1.28277 (19)	0.1359 (17)
O1	−0.07228 (11)	0.6992 (3)	0.11129 (11)	0.0655 (6)
H1	−0.0294	0.7422	0.1060	0.098*
O2	0.09556 (10)	0.9093 (3)	0.16978 (10)	0.0584 (6)
O3	0.61680 (9)	0.1973 (3)	0.91423 (10)	0.0626 (6)
H3A	0.6061	0.2342	0.9560	0.094*
O4	0.65614 (10)	0.3548 (3)	1.10066 (11)	0.0614 (6)
O5	0.10243 (14)	0.9509 (4)	0.32426 (12)	0.0823 (8)
O6	0.76091 (12)	0.0749 (3)	0.05910 (11)	0.0669 (7)
C1	−0.06363 (13)	0.6818 (3)	−0.02411 (15)	0.0364 (6)
C2	−0.10201 (15)	0.6524 (4)	0.04338 (17)	0.0452 (7)
C3	−0.17375 (16)	0.5708 (4)	0.04299 (19)	0.0577 (8)
H3	−0.1992	0.5539	0.0878	0.069*
C4	−0.20720 (16)	0.5150 (4)	−0.0231 (2)	0.0608 (9)
H4	−0.2546	0.4582	−0.0225	0.073*
C5	−0.17115 (17)	0.5424 (4)	−0.0898 (2)	0.0580 (9)
H5C	−0.1940	0.5052	−0.1346	0.070*
C6	−0.10039 (15)	0.6262 (4)	−0.08989 (16)	0.0480 (8)
H6	−0.0766	0.6460	−0.1354	0.058*
C7	0.01282 (13)	0.7672 (3)	−0.02630 (15)	0.0345 (6)
C8	0.05050 (15)	0.8057 (4)	−0.09932 (15)	0.0515 (8)
H8A	0.0888	0.8957	−0.0921	0.077*
H8B	0.0125	0.8457	−0.1350	0.077*
H8C	0.0744	0.7004	−0.1177	0.077*
C9	0.13657 (14)	0.9254 (4)	0.11518 (17)	0.0406 (7)
C10	0.21757 (14)	0.9977 (4)	0.12086 (16)	0.0496 (8)
H10A	0.2539	0.9009	0.1186	0.060*
H10B	0.2267	1.0749	0.0786	0.060*
C11	0.23035 (14)	1.0954 (4)	0.19022 (18)	0.0471 (8)
C12	0.47824 (13)	0.1629 (3)	0.90922 (15)	0.0389 (7)
C13	0.55132 (15)	0.1436 (4)	0.87800 (15)	0.0465 (8)
C14	0.55919 (17)	0.0688 (4)	0.80791 (17)	0.0619 (9)
H14	0.6080	0.0552	0.7882	0.074*
C15	0.4960 (2)	0.0143 (4)	0.76702 (17)	0.0643 (9)
H15	0.5023	−0.0372	0.7202	0.077*
C16	0.42393 (19)	0.0356 (4)	0.79496 (19)	0.0624 (9)
H16	0.3810	0.0012	0.7669	0.075*
C17	0.41539 (16)	0.1081 (4)	0.86462 (18)	0.0536 (8)
H17	0.3660	0.1215	0.8831	0.064*
C18	0.46728 (14)	0.2340 (3)	0.98523 (15)	0.0400 (7)
C19	0.38820 (15)	0.2469 (5)	1.01681 (17)	0.0688 (10)
H19A	0.3919	0.2576	1.0703	0.103*
H19B	0.3595	0.1427	1.0040	0.103*
H19C	0.3625	0.3487	0.9964	0.103*
C20	0.59330 (16)	0.3755 (4)	1.12859 (15)	0.0443 (7)
C21	0.58370 (16)	0.4428 (4)	1.20823 (15)	0.0546 (8)
H21A	0.5595	0.5582	1.2065	0.066*
H21B	0.5499	0.3637	1.2348	0.066*
C22	0.6557 (2)	0.4559 (5)	1.24854 (19)	0.0759 (11)
H2	0.1463 (13)	0.880 (4)	0.0059 (11)	0.080*
H5	0.4823 (10)	0.368 (4)	1.1171 (15)	0.080*
H5A	0.1041 (17)	0.937 (4)	0.2772 (6)	0.080*
H6A	0.7337 (16)	0.163 (3)	0.0707 (15)	0.080*
H5B	0.1286 (16)	1.039 (3)	0.3379 (15)	0.080*
H6B	0.7723 (17)	0.019 (3)	0.0987 (11)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0374 (12)	0.0357 (14)	0.0415 (15)	0.0014 (10)	−0.0027 (10)	0.0008 (12)
N2	0.0390 (12)	0.0451 (15)	0.0310 (15)	0.0014 (10)	−0.0022 (10)	−0.0015 (12)
N3	0.0771 (19)	0.074 (2)	0.057 (2)	−0.0111 (15)	−0.0134 (15)	−0.0057 (17)
N4	0.0430 (13)	0.0508 (15)	0.0303 (14)	0.0010 (11)	0.0024 (10)	0.0005 (12)
N5	0.0449 (14)	0.0549 (16)	0.0348 (15)	0.0034 (12)	0.0067 (11)	−0.0013 (13)
N6	0.092 (3)	0.233 (5)	0.082 (3)	−0.017 (3)	−0.021 (2)	−0.051 (3)
O1	0.0614 (13)	0.0916 (18)	0.0436 (14)	−0.0126 (12)	0.0070 (10)	0.0058 (12)
O2	0.0450 (11)	0.0912 (17)	0.0389 (13)	−0.0068 (10)	0.0018 (9)	−0.0022 (11)
O3	0.0386 (10)	0.1050 (18)	0.0441 (13)	0.0030 (11)	0.0005 (9)	−0.0131 (13)
O4	0.0458 (11)	0.0855 (17)	0.0530 (14)	−0.0069 (11)	0.0077 (9)	−0.0082 (12)
O5	0.0884 (17)	0.108 (2)	0.0508 (15)	−0.0382 (14)	0.0206 (13)	−0.0045 (15)
O6	0.0567 (13)	0.090 (2)	0.0542 (15)	0.0036 (11)	0.0051 (11)	0.0093 (13)
C1	0.0382 (14)	0.0330 (16)	0.0378 (17)	0.0080 (12)	−0.0024 (12)	0.0038 (14)
C2	0.0454 (15)	0.0450 (19)	0.045 (2)	0.0040 (14)	−0.0027 (14)	0.0052 (16)
C3	0.0477 (17)	0.060 (2)	0.065 (2)	−0.0003 (15)	0.0080 (16)	0.0150 (19)
C4	0.0408 (16)	0.049 (2)	0.092 (3)	−0.0020 (14)	−0.0071 (18)	0.009 (2)
C5	0.0531 (18)	0.053 (2)	0.067 (2)	−0.0006 (15)	−0.0208 (17)	−0.0009 (18)
C6	0.0485 (16)	0.0470 (19)	0.048 (2)	0.0045 (14)	−0.0059 (14)	0.0026 (15)
C7	0.0385 (14)	0.0317 (16)	0.0334 (17)	0.0075 (11)	−0.0017 (12)	0.0033 (13)
C8	0.0453 (15)	0.067 (2)	0.0417 (19)	−0.0043 (14)	−0.0018 (13)	0.0024 (16)
C9	0.0366 (14)	0.0436 (18)	0.0415 (19)	0.0054 (12)	−0.0011 (13)	0.0041 (15)
C10	0.0384 (15)	0.066 (2)	0.045 (2)	0.0052 (14)	−0.0032 (13)	−0.0046 (16)
C11	0.0392 (15)	0.055 (2)	0.047 (2)	−0.0027 (13)	−0.0065 (14)	0.0077 (17)
C12	0.0426 (15)	0.0383 (17)	0.0357 (17)	−0.0015 (12)	−0.0007 (12)	0.0086 (14)
C13	0.0465 (16)	0.060 (2)	0.0327 (18)	0.0011 (14)	−0.0028 (13)	0.0050 (16)
C14	0.0600 (19)	0.087 (3)	0.038 (2)	0.0016 (17)	0.0045 (15)	−0.0049 (19)
C15	0.090 (3)	0.070 (2)	0.033 (2)	−0.0125 (19)	−0.0023 (18)	0.0001 (17)
C16	0.071 (2)	0.064 (2)	0.052 (2)	−0.0215 (18)	−0.0126 (17)	0.0075 (19)
C17	0.0477 (17)	0.061 (2)	0.052 (2)	−0.0074 (15)	−0.0003 (15)	0.0073 (18)
C18	0.0392 (15)	0.0393 (18)	0.0414 (18)	0.0016 (12)	0.0012 (13)	0.0083 (14)
C19	0.0436 (17)	0.098 (3)	0.065 (2)	−0.0001 (17)	0.0098 (15)	−0.010 (2)
C20	0.0498 (17)	0.0450 (19)	0.0383 (18)	−0.0031 (14)	0.0052 (14)	0.0070 (15)
C21	0.0664 (19)	0.057 (2)	0.0404 (19)	−0.0009 (16)	0.0021 (15)	−0.0048 (16)
C22	0.074 (2)	0.105 (3)	0.049 (2)	−0.012 (2)	0.0000 (19)	−0.021 (2)

N1—C7	1.286 (3)	C5—H5C	0.9300
N1—N2	1.381 (3)	C6—H6	0.9300
N2—C9	1.348 (3)	C7—C8	1.498 (3)
N2—H2	0.904 (10)	C8—H8A	0.9600
N3—C11	1.135 (3)	C8—H8B	0.9600
N4—C18	1.286 (3)	C8—H8C	0.9600
N4—N5	1.378 (3)	C9—C10	1.513 (3)
N5—C20	1.346 (3)	C10—C11	1.457 (4)
N5—H5	0.901 (10)	C10—H10A	0.9700
N6—C22	1.115 (4)	C10—H10B	0.9700
O1—C2	1.357 (3)	C12—C13	1.404 (3)
O1—H1	0.8200	C12—C17	1.404 (4)
O2—C9	1.224 (3)	C12—C18	1.476 (3)
O3—C13	1.362 (3)	C13—C14	1.383 (4)
O3—H3A	0.8200	C14—C15	1.372 (4)
O4—C20	1.219 (3)	C14—H14	0.9300
O5—H5A	0.848 (10)	C15—C16	1.367 (4)
O5—H5B	0.845 (10)	C15—H15	0.9300
O6—H6A	0.848 (10)	C16—C17	1.370 (4)
O6—H6B	0.843 (10)	C16—H16	0.9300
C1—C6	1.393 (3)	C17—H17	0.9300
C1—C2	1.405 (4)	C18—C19	1.498 (3)
C1—C7	1.480 (3)	C19—H19A	0.9600
C2—C3	1.392 (4)	C19—H19B	0.9600
C3—C4	1.373 (4)	C19—H19C	0.9600
C3—H3	0.9300	C20—C21	1.523 (4)
C4—C5	1.372 (4)	C21—C22	1.437 (4)
C4—H4	0.9300	C21—H21A	0.9700
C5—C6	1.384 (4)	C21—H21B	0.9700
C7—N1—N2	121.1 (2)	C11—C10—H10A	109.3
C9—N2—N1	115.7 (2)	C9—C10—H10A	109.3
C9—N2—H2	123.0 (19)	C11—C10—H10B	109.3
N1—N2—H2	119.9 (19)	C9—C10—H10B	109.3
C18—N4—N5	120.6 (2)	H10A—C10—H10B	107.9
C20—N5—N4	117.4 (2)	N3—C11—C10	179.4 (3)
C20—N5—H5	117.9 (19)	C13—C12—C17	116.4 (3)
N4—N5—H5	124.7 (19)	C13—C12—C18	122.3 (2)
C2—O1—H1	109.5	C17—C12—C18	121.2 (2)
C13—O3—H3A	109.5	O3—C13—C14	117.2 (2)
H5A—O5—H5B	111 (2)	O3—C13—C12	122.4 (3)
H6A—O6—H6B	108 (2)	C14—C13—C12	120.4 (3)
C6—C1—C2	117.2 (2)	C15—C14—C13	121.0 (3)
C6—C1—C7	120.6 (2)	C15—C14—H14	119.5
C2—C1—C7	122.1 (2)	C13—C14—H14	119.5
O1—C2—C3	116.6 (3)	C16—C15—C14	120.1 (3)
O1—C2—C1	123.1 (2)	C16—C15—H15	120.0
C3—C2—C1	120.3 (3)	C14—C15—H15	120.0
C4—C3—C2	120.5 (3)	C15—C16—C17	119.5 (3)
C4—C3—H3	119.7	C15—C16—H16	120.2
C2—C3—H3	119.7	C17—C16—H16	120.2
C5—C4—C3	120.5 (3)	C16—C17—C12	122.6 (3)
C5—C4—H4	119.8	C16—C17—H17	118.7
C3—C4—H4	119.8	C12—C17—H17	118.7
C4—C5—C6	119.3 (3)	N4—C18—C12	115.5 (2)
C4—C5—H5C	120.4	N4—C18—C19	124.2 (3)
C6—C5—H5C	120.4	C12—C18—C19	120.2 (2)
C5—C6—C1	122.2 (3)	C18—C19—H19A	109.5
C5—C6—H6	118.9	C18—C19—H19B	109.5
C1—C6—H6	118.9	H19A—C19—H19B	109.5
N1—C7—C1	114.6 (2)	C18—C19—H19C	109.5
N1—C7—C8	124.4 (2)	H19A—C19—H19C	109.5
C1—C7—C8	121.0 (2)	H19B—C19—H19C	109.5
C7—C8—H8A	109.5	O4—C20—N5	124.1 (3)
C7—C8—H8B	109.5	O4—C20—C21	122.6 (3)
H8A—C8—H8B	109.5	N5—C20—C21	113.3 (2)
C7—C8—H8C	109.5	C22—C21—C20	112.5 (3)
H8A—C8—H8C	109.5	C22—C21—H21A	109.1
H8B—C8—H8C	109.5	C20—C21—H21A	109.1
O2—C9—N2	123.5 (2)	C22—C21—H21B	109.1
O2—C9—C10	122.5 (3)	C20—C21—H21B	109.1
N2—C9—C10	114.1 (2)	H21A—C21—H21B	107.8
C11—C10—C9	111.7 (2)	N6—C22—C21	176.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6B···N6i	0.84 (1)	2.17 (2)	2.975 (4)	159 (3)
O5—H5B···O3ii	0.85 (1)	2.43 (2)	3.120 (4)	140 (3)
O6—H6A···O4iii	0.85 (1)	2.06 (1)	2.900 (3)	173 (3)
O5—H5A···O2	0.85 (1)	1.93 (1)	2.777 (3)	174 (3)
N5—H5···O5iv	0.90 (1)	1.93 (1)	2.820 (3)	171 (3)
N2—H2···O6v	0.90 (1)	2.03 (1)	2.905 (3)	162 (3)
O3—H3A···N4	0.82	1.82	2.534 (3)	145.
O1—H1···N1	0.82	1.81	2.528 (3)	145.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6B⋯N6i	0.84 (1)	2.17 (2)	2.975 (4)	159 (3)
O5—H5B⋯O3ii	0.85 (1)	2.43 (2)	3.120 (4)	140 (3)
O6—H6A⋯O4iii	0.85 (1)	2.06 (1)	2.900 (3)	173 (3)
O5—H5A⋯O2	0.85 (1)	1.93 (1)	2.777 (3)	174 (3)
N5—H5⋯O5iv	0.90 (1)	1.93 (1)	2.820 (3)	171 (3)
N2—H2⋯O6v	0.90 (1)	2.03 (1)	2.905 (3)	162 (3)
O3—H3A⋯N4	0.82	1.82	2.534 (3)	145
O1—H1⋯N1	0.82	1.81	2.528 (3)	145

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