2-Cyano-N'-(2-hy-droxy-3-meth-oxy-benzyl-idene)acetohydrazide.

The title compound, C(11)H(11)N(3)O(3), was obtained by the reaction of 3-meth-oxy-salicyl-aldehyde with cyano-acetohydrazide in methanol. There is an intra-molecular O-H⋯N hydrogen bond in the mol-ecule. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds, generating chains running along the b axis.

Related literature

For the structures of hydrazones, see: Wang et al. (2011 ▶); Hashemian et al. (2011 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶).

Experimental

Crystal data

C11H11N3O3

M = 233.23

Orthorhombic,

a = 4.8035 (14) Å

b = 9.470 (3) Å

c = 23.884 (7) Å

V = 1086.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.23 × 0.18 × 0.17 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.976, T max = 0.982

6959 measured reflections

2298 independent reflections

1606 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.114

S = 1.04

2298 reflections

159 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.22 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/S1600536811025451/qm2013sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025451/qm2013Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025451/qm2013Isup3.cml

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

C11H11N3O3	Dx = 1.426 Mg m−3
Mr = 233.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1239 reflections
a = 4.8035 (14) Å	θ = 2.4–24.5°
b = 9.470 (3) Å	µ = 0.11 mm−1
c = 23.884 (7) Å	T = 298 K
V = 1086.5 (5) Å3	Block, colorless
Z = 4	0.23 × 0.18 × 0.17 mm
F(000) = 488

Bruker SMART 1K CCD area-detector diffractometer	2298 independent reflections
Radiation source: fine-focus sealed tube	1606 reflections with I > 2σ(I)
graphite	Rint = 0.058
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −6→6
Tmin = 0.976, Tmax = 0.982	k = −12→11
6959 measured reflections	l = −30→26

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0452P)2] where P = (Fo2 + 2Fc2)/3
2298 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.22 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	−0.1059 (5)	0.2286 (2)	0.20121 (9)	0.0327 (6)
N2	−0.2854 (5)	0.2894 (2)	0.23995 (10)	0.0357 (6)
N3	−0.9714 (7)	0.1500 (3)	0.37043 (13)	0.0710 (10)
O1	0.4649 (5)	−0.0612 (2)	0.06598 (9)	0.0509 (6)
O2	0.1150 (5)	0.02087 (19)	0.14348 (9)	0.0437 (6)
H2	−0.0004	0.0580	0.1641	0.066*
O3	−0.4697 (5)	0.0798 (2)	0.26659 (8)	0.0458 (6)
C1	0.2477 (6)	0.2652 (3)	0.13270 (11)	0.0300 (7)
C2	0.2719 (6)	0.1226 (3)	0.11849 (11)	0.0324 (7)
C3	0.4616 (6)	0.0810 (3)	0.07771 (12)	0.0385 (8)
C4	0.6298 (7)	0.1801 (3)	0.05190 (13)	0.0415 (8)
H4	0.7581	0.1522	0.0249	0.050*
C5	0.6059 (7)	0.3220 (3)	0.06656 (13)	0.0425 (8)
H5	0.7195	0.3885	0.0493	0.051*
C6	0.4189 (6)	0.3643 (3)	0.10575 (12)	0.0377 (7)
H6	0.4041	0.4595	0.1148	0.045*
C7	0.6697 (8)	−0.1109 (4)	0.02719 (13)	0.0619 (11)
H7A	0.6369	−0.0693	−0.0089	0.093*
H7B	0.6578	−0.2118	0.0243	0.093*
H7C	0.8518	−0.0848	0.0402	0.093*
C8	0.0503 (6)	0.3143 (3)	0.17435 (12)	0.0351 (7)
H8	0.0371	0.4106	0.1817	0.042*
C9	−0.4540 (6)	0.2074 (3)	0.27092 (11)	0.0316 (7)
C10	−0.6117 (7)	0.2931 (3)	0.31379 (12)	0.0392 (8)
H10A	−0.4798	0.3346	0.3398	0.047*
H10B	−0.7074	0.3697	0.2949	0.047*
C11	−0.8123 (7)	0.2116 (3)	0.34494 (13)	0.0412 (8)
H2A	−0.287 (8)	0.3840 (11)	0.2408 (13)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0339 (14)	0.0275 (12)	0.0369 (14)	0.0044 (12)	0.0030 (13)	−0.0002 (11)
N2	0.0430 (16)	0.0253 (12)	0.0388 (14)	0.0027 (13)	0.0097 (13)	−0.0028 (12)
N3	0.083 (3)	0.0503 (18)	0.080 (2)	−0.0227 (18)	0.035 (2)	−0.0092 (16)
O1	0.0569 (16)	0.0422 (12)	0.0537 (14)	0.0071 (10)	0.0123 (12)	−0.0065 (10)
O2	0.0443 (14)	0.0327 (11)	0.0541 (15)	0.0032 (10)	0.0151 (11)	0.0019 (9)
O3	0.0572 (15)	0.0251 (11)	0.0550 (13)	−0.0026 (10)	0.0130 (12)	−0.0022 (9)
C1	0.0288 (17)	0.0325 (16)	0.0286 (15)	−0.0016 (13)	−0.0042 (14)	0.0050 (13)
C2	0.0312 (18)	0.0338 (16)	0.0322 (16)	−0.0022 (14)	−0.0034 (14)	0.0037 (13)
C3	0.038 (2)	0.0424 (17)	0.0352 (17)	0.0060 (15)	−0.0015 (15)	0.0005 (15)
C4	0.0328 (18)	0.061 (2)	0.0308 (16)	0.0050 (16)	0.0044 (16)	0.0033 (15)
C5	0.038 (2)	0.0487 (19)	0.0411 (19)	−0.0096 (15)	0.0006 (16)	0.0101 (15)
C6	0.0377 (18)	0.0363 (15)	0.0389 (17)	−0.0017 (15)	−0.0015 (16)	0.0039 (14)
C7	0.067 (3)	0.067 (2)	0.052 (2)	0.010 (2)	0.008 (2)	−0.0204 (18)
C8	0.038 (2)	0.0296 (14)	0.0381 (17)	0.0015 (13)	−0.0017 (15)	−0.0016 (13)
C9	0.0327 (18)	0.0301 (16)	0.0319 (16)	0.0041 (13)	−0.0035 (14)	−0.0012 (13)
C10	0.0435 (19)	0.0307 (16)	0.0434 (18)	−0.0014 (15)	0.0096 (16)	−0.0058 (14)
C11	0.047 (2)	0.0310 (16)	0.0454 (19)	−0.0010 (15)	0.0064 (18)	−0.0085 (15)

N1—C8	1.278 (3)	C3—C4	1.384 (4)
N1—N2	1.390 (3)	C4—C5	1.393 (4)
N2—C9	1.344 (4)	C4—H4	0.9300
N2—H2A	0.896 (10)	C5—C6	1.358 (4)
N3—C11	1.138 (4)	C5—H5	0.9300
O1—C3	1.376 (3)	C6—H6	0.9300
O1—C7	1.431 (4)	C7—H7A	0.9600
O2—C2	1.361 (3)	C7—H7B	0.9600
O2—H2	0.8200	C7—H7C	0.9600
O3—C9	1.215 (3)	C8—H8	0.9300
C1—C2	1.396 (4)	C9—C10	1.510 (4)
C1—C6	1.404 (4)	C10—C11	1.442 (4)
C1—C8	1.451 (4)	C10—H10A	0.9700
C2—C3	1.391 (4)	C10—H10B	0.9700
C8—N1—N2	115.8 (2)	C5—C6—H6	119.8
C9—N2—N1	120.1 (2)	C1—C6—H6	119.8
C9—N2—H2A	124 (2)	O1—C7—H7A	109.5
N1—N2—H2A	116 (2)	O1—C7—H7B	109.5
C3—O1—C7	117.5 (2)	H7A—C7—H7B	109.5
C2—O2—H2	109.5	O1—C7—H7C	109.5
C2—C1—C6	119.1 (3)	H7A—C7—H7C	109.5
C2—C1—C8	122.1 (2)	H7B—C7—H7C	109.5
C6—C1—C8	118.8 (3)	N1—C8—C1	121.6 (3)
O2—C2—C3	118.0 (2)	N1—C8—H8	119.2
O2—C2—C1	122.1 (2)	C1—C8—H8	119.2
C3—C2—C1	119.9 (2)	O3—C9—N2	124.4 (3)
O1—C3—C4	124.5 (3)	O3—C9—C10	124.1 (3)
O1—C3—C2	115.3 (3)	N2—C9—C10	111.4 (2)
C4—C3—C2	120.1 (3)	C11—C10—C9	113.4 (2)
C3—C4—C5	119.6 (3)	C11—C10—H10A	108.9
C3—C4—H4	120.2	C9—C10—H10A	108.9
C5—C4—H4	120.2	C11—C10—H10B	108.9
C6—C5—C4	120.8 (3)	C9—C10—H10B	108.9
C6—C5—H5	119.6	H10A—C10—H10B	107.7
C4—C5—H5	119.6	N3—C11—C10	178.2 (3)
C5—C6—C1	120.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.90 (1)	2.20 (2)	2.995 (3)	148 (3)
O2—H2···N1	0.82	1.91	2.626 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.90 (1)	2.20 (2)	2.995 (3)	148 (3)
O2—H2⋯N1	0.82	1.91	2.626 (3)	145

Symmetry code: (i) .