(E,E)-1-(2-Hydroxy-imino-1-phenyl-ethyl-idene)semicarbazide monohydrate.

In the title compound, C(9)H(10)N(4)O(2)·H(2)O, the oxime unit has an E configuration, and an intra-molecular N-H⋯N hydrogen bond results in the formation of a planar five-membered ring, which is oriented with respect to the aromatic ring at a dihedral angle of 74.82 (17)°. In the crystal structure, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules and R(2) (2)(8) ring motifs are apparent.

Related literature

For general background, see: Balsamo et al. (1990 ▶); Marsman et al. (1999 ▶); Karle et al. (1996 ▶); Etter et al. (1990 ▶). For related structures, see: Sarıkavaklı et al. (2007 ▶, 2008 ▶); Özel Güven et al. (2007 ▶); Hökelek, Batı et al. (2001 ▶); Hökelek, Zülfikaroğlu et al. (2001 ▶); Büyükgüngör et al. (2003 ▶); Hökelek et al. (2004 ▶); Hökelek et al. (2004a ▶,b ▶). For reference structural data, see: Allen et al. (1987 ▶). For ring motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H10N4O2·H2O

M = 224.23

Triclinic,

a = 5.5593 (2) Å

b = 8.2701 (3) Å

c = 12.6193 (5) Å

α = 71.900 (3)°

β = 89.998 (5)°

γ = 78.538 (5)°

V = 539.29 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 294 K

0.40 × 0.25 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.968, T max = 0.978

1953 measured reflections

1752 independent reflections

867 reflections with I > 2σ(I)

R int = 0.048

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.185

S = 1.05

1752 reflections

171 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013865/hb2932sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013865/hb2932Isup2.hkl

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

C9H10N4O2·H2O	Z = 2
Mr = 224.23	F(000) = 236
Triclinic, P1	Dx = 1.381 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5593 (2) Å	Cell parameters from 25 reflections
b = 8.2701 (3) Å	θ = 8.6–17.3°
c = 12.6193 (5) Å	µ = 0.11 mm−1
α = 71.900 (3)°	T = 294 K
β = 89.998 (5)°	Prism, colorless
γ = 78.538 (5)°	0.40 × 0.25 × 0.20 mm
V = 539.29 (4) Å3

Enraf–Nonius TurboCAD-4 diffractometer	867 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
graphite	θmax = 24.3°, θmin = 3.4°
Non–profiled ω scans	h = −6→0
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
Tmin = 0.968, Tmax = 0.978	l = −14→14
1953 measured reflections	3 standard reflections every 120 min
1752 independent reflections	intensity decay: 1%

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0859P)2] where P = (Fo2 + 2Fc2)/3
1752 reflections	(Δ/σ)max < 0.001
171 parameters	Δρmax = 0.19 e Å−3
5 restraints	Δρmin = −0.34 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
O1	0.5650 (8)	−0.2847 (5)	0.9749 (4)	0.0635 (13)
O2	1.6136 (8)	−0.2215 (5)	0.5421 (4)	0.0583 (13)
H21	1.658 (12)	−0.131 (10)	0.490 (6)	0.09 (3)*
O3	0.2334 (12)	−0.0741 (10)	1.0657 (7)	0.132 (3)
H31	0.344 (10)	−0.122 (11)	1.028 (6)	0.125*
H32	0.088 (7)	−0.084 (10)	1.041 (7)	0.125*
N1	1.0377 (8)	−0.2812 (6)	0.7948 (4)	0.0456 (13)
N2	0.8573 (9)	−0.2253 (6)	0.8554 (4)	0.0498 (14)
H22	0.823 (9)	−0.128 (4)	0.863 (4)	0.040 (17)*
N3	0.7601 (11)	−0.4938 (7)	0.9070 (5)	0.0594 (16)
H3A	0.884 (8)	−0.531 (8)	0.872 (5)	0.08 (2)*
H3B	0.665 (11)	−0.578 (9)	0.942 (5)	0.08 (2)*
N4	1.4358 (8)	−0.1346 (5)	0.5950 (4)	0.0435 (13)
C1	1.0910 (10)	0.0218 (7)	0.7132 (5)	0.0389 (14)
C2	1.2415 (11)	0.0996 (7)	0.7590 (5)	0.0538 (17)
H2	1.3800	0.0317	0.8044	0.065*
C3	1.1895 (12)	0.2758 (8)	0.7384 (6)	0.0646 (19)
H3	1.2905	0.3257	0.7719	0.077*
C4	0.9938 (13)	0.3786 (8)	0.6700 (6)	0.0602 (18)
H4	0.9626	0.4987	0.6543	0.072*
C5	0.8426 (12)	0.3024 (8)	0.6244 (5)	0.065 (2)
H5	0.7064	0.3716	0.5778	0.078*
C6	0.8891 (12)	0.1243 (8)	0.6466 (5)	0.0591 (18)
H6	0.7829	0.0742	0.6162	0.071*
C7	1.1479 (10)	−0.1688 (6)	0.7314 (4)	0.0387 (14)
C8	0.7189 (11)	−0.3364 (7)	0.9167 (5)	0.0455 (15)
C9	1.3383 (11)	−0.2382 (8)	0.6696 (5)	0.0444 (15)
H9	1.374 (10)	−0.359 (9)	0.687 (5)	0.064 (19)*

	U11	U22	U33	U12	U13	U23
O1	0.066 (3)	0.051 (3)	0.078 (3)	−0.018 (2)	0.036 (3)	−0.024 (2)
O2	0.062 (3)	0.044 (3)	0.064 (3)	−0.005 (2)	0.026 (2)	−0.014 (2)
O3	0.106 (5)	0.148 (6)	0.173 (7)	0.002 (5)	0.008 (5)	−0.111 (5)
N1	0.049 (3)	0.041 (3)	0.048 (3)	−0.012 (2)	0.017 (3)	−0.013 (2)
N2	0.058 (3)	0.036 (3)	0.057 (3)	−0.015 (3)	0.019 (3)	−0.014 (3)
N3	0.065 (4)	0.043 (3)	0.076 (4)	−0.022 (3)	0.030 (3)	−0.019 (3)
N4	0.046 (3)	0.037 (3)	0.046 (3)	−0.006 (2)	0.009 (2)	−0.012 (2)
C1	0.038 (3)	0.035 (3)	0.041 (3)	−0.007 (3)	0.011 (3)	−0.010 (3)
C2	0.050 (4)	0.042 (4)	0.066 (4)	−0.005 (3)	−0.008 (3)	−0.014 (3)
C3	0.062 (4)	0.046 (4)	0.089 (5)	−0.016 (4)	−0.003 (4)	−0.024 (4)
C4	0.074 (5)	0.035 (3)	0.071 (5)	−0.013 (4)	0.013 (4)	−0.016 (3)
C5	0.068 (5)	0.045 (4)	0.067 (5)	0.010 (4)	−0.011 (4)	−0.007 (4)
C6	0.060 (4)	0.045 (4)	0.065 (4)	−0.008 (3)	−0.014 (4)	−0.010 (3)
C7	0.043 (3)	0.032 (3)	0.037 (3)	−0.009 (3)	0.002 (3)	−0.005 (3)
C8	0.049 (4)	0.035 (3)	0.046 (4)	−0.009 (3)	0.012 (3)	−0.005 (3)
C9	0.051 (4)	0.031 (3)	0.051 (4)	−0.011 (3)	0.007 (3)	−0.012 (3)

O1—C8	1.226 (6)	C2—H2	0.9300
O2—N4	1.399 (5)	C3—H3	0.9300
O2—H21	0.91 (8)	C4—C3	1.352 (9)
O3—H31	0.88 (7)	C4—C5	1.368 (9)
O3—H32	0.90 (3)	C4—H4	0.9300
N1—C7	1.281 (6)	C5—C6	1.381 (8)
N2—N1	1.357 (6)	C5—H5	0.9300
N2—C8	1.369 (7)	C6—H6	0.9300
N2—H22	0.82 (3)	C7—C1	1.489 (7)
N3—H3A	0.88 (3)	C8—N3	1.320 (7)
N3—H3B	0.96 (7)	C9—N4	1.264 (7)
C1—C2	1.376 (8)	C9—C7	1.447 (7)
C1—C6	1.365 (8)	C9—H9	0.94 (6)
C2—C3	1.368 (8)
N4—O2—H21	101 (4)	C3—C4—C5	118.6 (6)
H31—O3—H32	105 (4)	C3—C4—H4	120.7
C7—N1—N2	118.1 (5)	C5—C4—H4	120.7
N1—N2—C8	120.5 (5)	C4—C5—C6	121.0 (6)
N1—N2—H22	126 (4)	C4—C5—H5	119.5
C8—N2—H22	113 (4)	C6—C5—H5	119.5
C8—N3—H3A	122 (4)	C1—C6—C5	120.0 (6)
C8—N3—H3B	123 (4)	C1—C6—H6	120.0
H3A—N3—H3B	115 (6)	C5—C6—H6	120.0
C9—N4—O2	112.3 (4)	N1—C7—C1	126.4 (5)
C2—C1—C7	121.7 (5)	N1—C7—C9	114.9 (5)
C6—C1—C2	118.6 (5)	C9—C7—C1	118.7 (5)
C6—C1—C7	119.7 (5)	O1—C8—N2	119.1 (5)
C1—C2—H2	119.7	O1—C8—N3	124.4 (6)
C3—C2—C1	120.7 (6)	N3—C8—N2	116.5 (5)
C3—C2—H2	119.7	N4—C9—C7	119.3 (5)
C2—C3—H3	119.5	N4—C9—H9	125 (4)
C4—C3—C2	121.1 (6)	C7—C9—H9	116 (3)
C4—C3—H3	119.5
N2—N1—C7—C1	−2.8 (8)	C5—C4—C3—C2	2.2 (10)
N2—N1—C7—C9	179.9 (5)	C3—C4—C5—C6	−0.6 (10)
C8—N2—N1—C7	174.2 (5)	C4—C5—C6—C1	−1.2 (10)
N1—N2—C8—O1	176.6 (5)	N1—C7—C1—C2	106.3 (7)
N1—N2—C8—N3	−4.4 (8)	N1—C7—C1—C6	−75.8 (8)
C6—C1—C2—C3	0.1 (9)	C9—C7—C1—C2	−76.5 (7)
C7—C1—C2—C3	178.0 (6)	C9—C7—C1—C6	101.4 (6)
C2—C1—C6—C5	1.4 (9)	N4—C9—C7—N1	171.4 (5)
C7—C1—C6—C5	−176.5 (6)	N4—C9—C7—C1	−6.1 (8)
C1—C2—C3—C4	−2.0 (10)	C7—C9—N4—O2	−179.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1	0.88 (3)	2.32 (6)	2.647 (8)	102 (5)
O3—H31···O1	0.88 (7)	1.92 (8)	2.776 (9)	164 (8)
O3—H32···O3i	0.90 (3)	2.17 (7)	2.909 (11)	140 (7)
N2—H22···O3ii	0.82 (3)	2.10 (4)	2.901 (10)	162 (5)
N3—H3B···O1iii	0.96 (7)	1.96 (6)	2.909 (8)	169 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1	0.88 (3)	2.32 (6)	2.647 (8)	102 (5)
O3—H31⋯O1	0.88 (7)	1.92 (8)	2.776 (9)	164 (8)
O3—H32⋯O3i	0.90 (3)	2.17 (7)	2.909 (11)	140 (7)
N2—H22⋯O3ii	0.82 (3)	2.10 (4)	2.901 (10)	162 (5)
N3—H3B⋯O1iii	0.96 (7)	1.96 (6)	2.909 (8)	169 (6)

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