(2E)-2-(3-Eth-oxy-2-hy-droxy-benzyl-idene)hydrazinecarboxamide.

The title compound, C10H13N3O3, adopts an E conformation with respect to the azomethine bond and crystallizes in the amide form. A classical intra-molecular O-H⋯N hydrogen bond is present. The two N atoms of the hydrazinecarboxamide unit are also involved in inter-molecular N-H⋯O hydrogen bonds, with the O atom of the hydrazinecarboxamide group acting as the acceptor. Pairs of N-H⋯O hydrogen bond link the mol-ecules into centrosymmetric dimers, which are linked by further N-H⋯O hydrogen bonds into chains along the b axis. The chains are linked by C-H⋯π inter-actions.

Related literature

For biological applications of hydrazinecarboxamide and its derivatives, see: Afrasiabi et al. (2005 ▶); Siji et al. (2010 ▶); Beraldo & Gambino (2004 ▶). For related structures and background references, see: Sithambaresan & Kurup (2011 ▶); Noblía et al. (2004, ▶ 2005 ▶); Benítez et al. (2009 ▶, 2011 ▶); Rivadeneira et al. (2009 ▶); Gambino et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶); Kala et al. (2007 ▶). For the synthesis, see: Sreekanth et al. (2004 ▶).

Experimental

Crystal data

C10H13N3O3

M = 223.23

Triclinic,

a = 5.0676 (4) Å

b = 7.0426 (7) Å

c = 15.8394 (15) Å

α = 97.509 (4)°

β = 98.819 (3)°

γ = 105.790 (4)°

V = 528.62 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.969, T max = 0.979

2559 measured reflections

1794 independent reflections

1496 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.109

S = 1.05

1794 reflections

163 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2010 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007617/fj2621sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007617/fj2621Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007617/fj2621Isup3.cml

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

C10H13N3O3	Z = 2
Mr = 223.23	F(000) = 236.0
Triclinic, P1	Dx = 1.403 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0676 (4) Å	Cell parameters from 1468 reflections
b = 7.0426 (7) Å	θ = 3.1–27.8°
c = 15.8394 (15) Å	µ = 0.11 mm−1
α = 97.509 (4)°	T = 296 K
β = 98.819 (3)°	Needle, colorless
γ = 105.790 (4)°	0.30 × 0.25 × 0.20 mm
V = 528.62 (8) Å3

Bruker Kappa APEXII CCD diffractometer	1794 independent reflections
Radiation source: fine-focus sealed tube	1496 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
Detector resolution: 8.33 pixels mm-1	θmax = 25.0°, θmin = 2.7°
ω and φ scan	h = −4→6
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −8→7
Tmin = 0.969, Tmax = 0.979	l = −18→18
2559 measured reflections

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0603P)2 + 0.0879P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1794 reflections	Δρmax = 0.15 e Å−3
163 parameters	Δρmin = −0.18 e Å−3
5 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (11)

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	0.0222 (2)	0.77360 (18)	0.14679 (8)	0.0535 (4)
O2	0.4871 (2)	0.95529 (17)	0.25818 (8)	0.0507 (4)
N3	1.1509 (3)	1.3215 (2)	0.44231 (10)	0.0451 (4)
N1	0.9230 (2)	0.92842 (19)	0.36957 (8)	0.0378 (3)
N2	1.1846 (3)	1.0000 (2)	0.42199 (9)	0.0415 (4)
O3	1.5573 (2)	1.25778 (16)	0.48904 (8)	0.0484 (3)
C1	0.4059 (3)	0.7519 (2)	0.24373 (10)	0.0380 (4)
C2	0.1566 (3)	0.6509 (2)	0.18340 (10)	0.0409 (4)
C3	0.0673 (3)	0.4439 (3)	0.16548 (11)	0.0482 (4)
H3	−0.0981	0.3773	0.1258	0.058*
C4	0.2212 (4)	0.3340 (3)	0.20585 (12)	0.0518 (5)
H4	0.1593	0.1945	0.1932	0.062*
C5	0.4660 (3)	0.4317 (3)	0.26476 (11)	0.0460 (4)
H5	0.5691	0.3576	0.2916	0.055*
C6	0.5613 (3)	0.6415 (2)	0.28465 (9)	0.0374 (4)
C7	0.8283 (3)	0.7384 (2)	0.34449 (9)	0.0383 (4)
H7	0.9336	0.6587	0.3652	0.046*
C8	1.3056 (3)	1.1985 (2)	0.45241 (9)	0.0359 (4)
C9	−0.2192 (3)	0.6811 (3)	0.07918 (11)	0.0510 (5)
H9A	−0.3608	0.5872	0.1005	0.061*
H9B	−0.1694	0.6088	0.0307	0.061*
C10	−0.3277 (4)	0.8456 (3)	0.05117 (13)	0.0641 (6)
H10A	−0.3775	0.9153	0.0996	0.096*
H10B	−0.4897	0.7890	0.0054	0.096*
H10C	−0.1854	0.9378	0.0305	0.096*
H2	1.274 (3)	0.917 (2)	0.4371 (11)	0.045 (5)*
H2'	0.642 (3)	0.984 (3)	0.2920 (12)	0.079 (7)*
H3A	1.223 (3)	1.4467 (15)	0.4605 (12)	0.061 (6)*
H3B	0.975 (2)	1.278 (3)	0.4271 (13)	0.068 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0390 (6)	0.0514 (8)	0.0589 (7)	0.0127 (5)	−0.0154 (5)	0.0016 (6)
O2	0.0410 (7)	0.0387 (7)	0.0609 (8)	0.0109 (5)	−0.0143 (5)	−0.0013 (5)
N3	0.0284 (7)	0.0373 (8)	0.0621 (9)	0.0075 (6)	−0.0051 (6)	0.0045 (7)
N1	0.0270 (7)	0.0419 (8)	0.0375 (7)	0.0069 (5)	−0.0039 (5)	0.0016 (6)
N2	0.0284 (7)	0.0392 (8)	0.0493 (8)	0.0102 (6)	−0.0094 (5)	0.0010 (6)
O3	0.0246 (6)	0.0407 (7)	0.0695 (8)	0.0063 (5)	−0.0086 (5)	0.0021 (5)
C1	0.0323 (8)	0.0383 (9)	0.0383 (8)	0.0081 (7)	0.0016 (6)	0.0009 (6)
C2	0.0315 (8)	0.0461 (10)	0.0405 (8)	0.0107 (7)	−0.0008 (6)	0.0029 (7)
C3	0.0345 (9)	0.0492 (10)	0.0474 (9)	0.0026 (7)	−0.0057 (7)	−0.0013 (7)
C4	0.0468 (10)	0.0385 (9)	0.0569 (10)	0.0015 (8)	−0.0026 (8)	0.0018 (8)
C5	0.0434 (9)	0.0411 (9)	0.0471 (9)	0.0086 (7)	−0.0022 (7)	0.0075 (7)
C6	0.0316 (8)	0.0418 (9)	0.0341 (8)	0.0075 (7)	0.0018 (6)	0.0032 (6)
C7	0.0341 (8)	0.0392 (9)	0.0381 (8)	0.0108 (7)	−0.0012 (6)	0.0050 (7)
C8	0.0270 (7)	0.0386 (8)	0.0382 (8)	0.0075 (6)	0.0006 (6)	0.0053 (6)
C9	0.0367 (9)	0.0647 (12)	0.0425 (9)	0.0128 (8)	−0.0072 (7)	−0.0004 (8)
C10	0.0483 (11)	0.0769 (14)	0.0604 (12)	0.0167 (10)	−0.0099 (9)	0.0168 (10)

O1—C2	1.3697 (19)	C3—C4	1.386 (2)
O1—C9	1.4319 (18)	C3—H3	0.9300
O2—C1	1.3558 (19)	C4—C5	1.377 (2)
O2—H2'	0.837 (10)	C4—H4	0.9300
N3—C8	1.326 (2)	C5—C6	1.400 (2)
N3—H3A	0.849 (9)	C5—H5	0.9300
N3—H3B	0.846 (9)	C6—C7	1.459 (2)
N1—C7	1.278 (2)	C7—H7	0.9300
N1—N2	1.3749 (17)	C9—C10	1.499 (3)
N2—C8	1.352 (2)	C9—H9A	0.9700
N2—H2	0.869 (9)	C9—H9B	0.9700
O3—C8	1.2481 (17)	C10—H10A	0.9600
C1—C6	1.397 (2)	C10—H10B	0.9600
C1—C2	1.407 (2)	C10—H10C	0.9600
C2—C3	1.380 (2)
C2—O1—C9	117.61 (13)	C6—C5—H5	119.7
C1—O2—H2'	102.2 (16)	C1—C6—C5	119.31 (14)
C8—N3—H3A	120.2 (13)	C1—C6—C7	121.94 (14)
C8—N3—H3B	121.7 (13)	C5—C6—C7	118.68 (14)
H3A—N3—H3B	117.1 (17)	N1—C7—C6	122.59 (14)
C7—N1—N2	116.34 (13)	N1—C7—H7	118.7
C8—N2—N1	121.45 (13)	C6—C7—H7	118.7
C8—N2—H2	118.6 (12)	O3—C8—N3	122.89 (15)
N1—N2—H2	120.0 (12)	O3—C8—N2	118.66 (13)
O2—C1—C6	122.85 (14)	N3—C8—N2	118.45 (13)
O2—C1—C2	117.48 (14)	O1—C9—C10	107.13 (15)
C6—C1—C2	119.66 (15)	O1—C9—H9A	110.3
O1—C2—C3	125.56 (14)	C10—C9—H9A	110.3
O1—C2—C1	114.78 (14)	O1—C9—H9B	110.3
C3—C2—C1	119.66 (14)	C10—C9—H9B	110.3
C2—C3—C4	120.82 (15)	H9A—C9—H9B	108.5
C2—C3—H3	119.6	C9—C10—H10A	109.5
C4—C3—H3	119.6	C9—C10—H10B	109.5
C5—C4—C3	119.85 (16)	H10A—C10—H10B	109.5
C5—C4—H4	120.1	C9—C10—H10C	109.5
C3—C4—H4	120.1	H10A—C10—H10C	109.5
C4—C5—C6	120.70 (15)	H10B—C10—H10C	109.5
C4—C5—H5	119.7
C7—N1—N2—C8	−179.98 (14)	C2—C1—C6—C5	0.1 (2)
C9—O1—C2—C3	−5.3 (2)	O2—C1—C6—C7	−1.8 (2)
C9—O1—C2—C1	174.53 (14)	C2—C1—C6—C7	176.94 (13)
O2—C1—C2—O1	−0.8 (2)	C4—C5—C6—C1	−0.3 (3)
C6—C1—C2—O1	−179.55 (13)	C4—C5—C6—C7	−177.26 (14)
O2—C1—C2—C3	179.03 (14)	N2—N1—C7—C6	−176.32 (13)
C6—C1—C2—C3	0.3 (2)	C1—C6—C7—N1	6.9 (2)
O1—C2—C3—C4	179.43 (16)	C5—C6—C7—N1	−176.21 (15)
C1—C2—C3—C4	−0.4 (3)	N1—N2—C8—O3	−169.81 (13)
C2—C3—C4—C5	0.1 (3)	N1—N2—C8—N3	10.5 (2)
C3—C4—C5—C6	0.2 (3)	C2—O1—C9—C10	179.40 (14)
O2—C1—C6—C5	−178.64 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O3i	0.85 (1)	2.06 (1)	2.9034 (19)	173 (2)
O2—H2′···N1	0.84 (1)	1.89 (1)	2.6736 (15)	155 (2)
N2—H2···O3ii	0.87 (1)	2.06 (1)	2.8965 (17)	161 (2)
C9—H9A···Cgiii	0.97	2.75	3.5896 (19)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O3i	0.85 (1)	2.06 (1)	2.9034 (19)	173 (2)
O2—H2′⋯N1	0.84 (1)	1.89 (1)	2.6736 (15)	155 (2)
N2—H2⋯O3ii	0.87 (1)	2.06 (1)	2.8965 (17)	161 (2)
C9—H9A⋯Cg iii	0.97	2.75	3.5896 (19)	145

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