N'-(2-Hy-droxy-benzyl-idene)-2-(hy-droxy-imino)-propano-hydrazide.

The mol-ecule of the title compound, C(10)H(11)N(3)O(3), adopts an all-trans conformation and is approxomately planar, the largest deviation from the least-squares plane through all non-H atoms being 0.261 (1) Å. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, the mol-ecules are packed into layers lying parallel to the ab plane by π-stacking inter-actions between the benzene ring of one molecule and the C-N bond of the oxime group of another molecule; the shortest inter-molecular C⋯C separation within the layer is 3.412 (1) Å. The layers are connected by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For the preparation and characterization of 3d metal complexes with related n class="Chemical">oxime derivatives, see: Kanderal et al. (2005 ▶); Moroz et al. (2010 ▶). For the crystal structures of similar oxime derivatives, see: Świątek-Kozłowska et al. (2000 ▶); Mokhir et al. (2002 ▶); Sachse et al. (2008 ▶). For 2-hy­droxy­imino­propanamide and amide derivatives of 2-hy­droxy­imino­propanoic acid, see: Onindo et al. (1995 ▶); Duda et al. (1997 ▶); Sliva et al. (1997 ▶). For the synthesis of 2-(hy­droxy­imino)­propane­hydrazide, see: Fritsky et al. (1998 ▶). For related structures, see: Krämer & Fritsky (2000 ▶); Wörl et al. (2005 ▶).

Experimental

Crystal data

C10H11N3O3

M = 221.22

Monoclinic,

a = 11.2296 (4) Å

b = 8.1905 (4) Å

c = 11.1000 (5) Å

β = 102.223 (2)°

V = 997.79 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.61 × 0.47 × 0.34 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.935, T max = 0.964

16456 measured reflections

2465 independent reflections

2383 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.086

S = 1.07

2465 reflections

148 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811045818/yk2025sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045818/yk2025Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045818/yk2025Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811045818/yk2025Isup4.cml

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

C10H11N3O3	F(000) = 464
Mr = 221.22	Dx = 1.473 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 9875 reflections
a = 11.2296 (4) Å	θ = 3.1–36.5°
b = 8.1905 (4) Å	µ = 0.11 mm−1
c = 11.1000 (5) Å	T = 100 K
β = 102.223 (2)°	Block, yellow
V = 997.79 (8) Å3	0.61 × 0.47 × 0.34 mm
Z = 4

Bruker Kappa APEXII DUO CCD diffractometer	2465 independent reflections
Radiation source: fine-focus sealed tube	2383 reflections with I > 2σ(I)
curved graphite crystal	Rint = 0.015
Detector resolution: 16 pixels mm-1	θmax = 36.6°, θmin = 3.1°
φ scans and ω scans with κ offset	h = −18→18
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	k = −13→13
Tmin = 0.935, Tmax = 0.964	l = −17→18
16456 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.0678P] where P = (Fo2 + 2Fc2)/3
2465 reflections	(Δ/σ)max < 0.001
148 parameters	Δρmax = 0.42 e Å−3
2 restraints	Δρmin = −0.22 e Å−3

Geometry. All s.u.'s (except the s.u.'s in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.43931 (7)	−0.17009 (9)	0.11307 (6)	0.01652 (13)
H1	0.4154	−0.0863	0.1446	0.025*
O2	0.34012 (7)	0.24663 (9)	0.12079 (6)	0.01761 (13)
O3	0.27014 (7)	0.63005 (9)	0.39602 (7)	0.01675 (13)
H3	0.2975	0.6608	0.4688	0.025*
N1	0.43375 (7)	0.03499 (9)	0.28832 (7)	0.01324 (13)
N2	0.39288 (7)	0.18082 (9)	0.32287 (6)	0.01328 (12)
H2	0.3983	0.2071	0.4007	0.016*
N3	0.32114 (7)	0.48105 (9)	0.37696 (7)	0.01365 (13)
C1	0.50374 (8)	−0.26684 (11)	0.20397 (8)	0.01297 (13)
C2	0.54689 (9)	−0.41516 (12)	0.16937 (8)	0.01686 (15)
H2A	0.5302	−0.4465	0.0851	0.020*
C3	0.61440 (9)	−0.51730 (12)	0.25817 (9)	0.01803 (16)
H3A	0.6450	−0.6173	0.2337	0.022*
C4	0.63779 (9)	−0.47511 (11)	0.38250 (9)	0.01695 (15)
H4	0.6840	−0.5455	0.4427	0.020*
C5	0.59273 (8)	−0.32933 (11)	0.41698 (8)	0.01476 (14)
H5	0.6073	−0.3011	0.5019	0.018*
C6	0.52600 (8)	−0.22227 (10)	0.32956 (7)	0.01217 (13)
C7	0.48236 (8)	−0.06904 (11)	0.37043 (7)	0.01343 (14)
H7	0.4897	−0.0466	0.4557	0.016*
C8	0.34332 (8)	0.28258 (10)	0.22951 (7)	0.01258 (13)
C9	0.29200 (7)	0.43934 (10)	0.26290 (7)	0.01256 (13)
C10	0.21336 (9)	0.53605 (12)	0.16288 (8)	0.01674 (15)
H10A	0.1476	0.5877	0.1948	0.025*
H10B	0.1784	0.4635	0.0943	0.025*
H10C	0.2625	0.6204	0.1339	0.025*

	U11	U22	U33	U12	U13	U23
O1	0.0240 (3)	0.0136 (3)	0.0116 (2)	0.0019 (2)	0.0029 (2)	0.0001 (2)
O2	0.0277 (3)	0.0146 (3)	0.0108 (2)	0.0026 (2)	0.0044 (2)	−0.0002 (2)
O3	0.0226 (3)	0.0130 (3)	0.0146 (2)	0.0040 (2)	0.0037 (2)	−0.0023 (2)
N1	0.0175 (3)	0.0093 (3)	0.0132 (3)	0.0009 (2)	0.0040 (2)	−0.0002 (2)
N2	0.0185 (3)	0.0099 (3)	0.0115 (2)	0.0019 (2)	0.0034 (2)	−0.0002 (2)
N3	0.0167 (3)	0.0111 (3)	0.0132 (3)	0.0007 (2)	0.0034 (2)	−0.0006 (2)
C1	0.0156 (3)	0.0117 (3)	0.0121 (3)	−0.0010 (2)	0.0040 (2)	−0.0008 (2)
C2	0.0217 (4)	0.0137 (3)	0.0161 (3)	0.0011 (3)	0.0062 (3)	−0.0024 (3)
C3	0.0201 (4)	0.0137 (3)	0.0215 (4)	0.0026 (3)	0.0071 (3)	−0.0018 (3)
C4	0.0176 (4)	0.0136 (3)	0.0198 (3)	0.0023 (3)	0.0042 (3)	0.0016 (3)
C5	0.0169 (3)	0.0125 (3)	0.0142 (3)	0.0007 (3)	0.0019 (3)	0.0011 (2)
C6	0.0149 (3)	0.0102 (3)	0.0115 (3)	−0.0006 (2)	0.0030 (2)	0.0002 (2)
C7	0.0169 (3)	0.0113 (3)	0.0117 (3)	0.0007 (3)	0.0023 (2)	−0.0006 (2)
C8	0.0155 (3)	0.0102 (3)	0.0121 (3)	−0.0001 (2)	0.0028 (2)	0.0004 (2)
C9	0.0145 (3)	0.0109 (3)	0.0123 (3)	0.0000 (2)	0.0029 (2)	0.0001 (2)
C10	0.0178 (4)	0.0173 (4)	0.0145 (3)	0.0039 (3)	0.0019 (3)	0.0022 (3)

O1—C1	1.3640 (11)	C3—C4	1.3926 (14)
O1—H1	0.8400	C3—H3A	0.9500
O2—C8	1.2352 (10)	C4—C5	1.3822 (13)
O3—N3	1.3832 (10)	C4—H4	0.9500
O3—H3	0.8400	C5—C6	1.4014 (11)
N1—C7	1.2822 (10)	C5—H5	0.9500
N1—N2	1.3634 (10)	C6—C7	1.4543 (12)
N2—C8	1.3543 (10)	C7—H7	0.9500
N2—H2	0.8800	C8—C9	1.4861 (12)
N3—C9	1.2850 (11)	C9—C10	1.4916 (12)
C1—C2	1.3917 (12)	C10—H10A	0.9800
C1—C6	1.4113 (11)	C10—H10B	0.9800
C2—C3	1.3891 (14)	C10—H10C	0.9800
C2—H2A	0.9500
C1—O1—H1	109.5	C4—C5—H5	119.3
N3—O3—H3	109.5	C6—C5—H5	119.3
C7—N1—N2	120.02 (7)	C5—C6—C1	118.62 (7)
C8—N2—N1	115.60 (7)	C5—C6—C7	119.34 (7)
C8—N2—H2	122.2	C1—C6—C7	122.03 (7)
N1—N2—H2	122.2	N1—C7—C6	118.21 (7)
C9—N3—O3	110.98 (7)	N1—C7—H7	120.9
O1—C1—C2	117.65 (7)	C6—C7—H7	120.9
O1—C1—C6	122.40 (7)	O2—C8—N2	121.54 (8)
C2—C1—C6	119.95 (8)	O2—C8—C9	121.13 (7)
C3—C2—C1	119.97 (8)	N2—C8—C9	117.32 (7)
C3—C2—H2A	120.0	N3—C9—C8	116.37 (7)
C1—C2—H2A	120.0	N3—C9—C10	125.40 (8)
C2—C3—C4	120.92 (9)	C8—C9—C10	118.22 (7)
C2—C3—H3A	119.5	C9—C10—H10A	109.5
C4—C3—H3A	119.5	C9—C10—H10B	109.5
C5—C4—C3	119.05 (8)	H10A—C10—H10B	109.5
C5—C4—H4	120.5	C9—C10—H10C	109.5
C3—C4—H4	120.5	H10A—C10—H10C	109.5
C4—C5—C6	121.48 (8)	H10B—C10—H10C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84	1.85	2.5808 (10)	144.
O3—H3···O2i	0.84	1.82	2.6518 (9)	171.
N2—H2···O1ii	0.88	2.32	3.1535 (9)	157.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84	1.85	2.5808 (10)	144
O3—H3⋯O2i	0.84	1.82	2.6518 (9)	171
N2—H2⋯O1ii	0.88	2.32	3.1535 (9)	157

Symmetry codes: (i) ; (ii) .