2-Cyano-N′-(2-hy­droxy-3-meth­oxy­benzyl­idene)acetohydrazide

Li, H.; Chen, P.

doi:10.1107/S1600536811025451

organic compounds

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Volume 67| Part 8| August 2011| Page o2001

doi:10.1107/S1600536811025451

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2-Cyano-N′-(2-hydroxy-3-methoxybenzylidene)acetohydrazide

Hongbo Li ^a ^* and Peng Chen ^a

^aCollege of Chemistry and Biology Engineering, Yancheng Institute of Technology, Yancheng 224051, People's Republic of China
^*Correspondence e-mail: hbli@ycit.edu.cn

(Received 25 June 2011; accepted 28 June 2011; online 9 July 2011)

The title compound, C₁₁H₁₁N₃O₃, was obtained by the reaction of 3-methoxysalicylaldehyde with cyanoacetohydrazide in methanol. There is an intramolecular O—H⋯N hydrogen bond in the molecule. In the crystal, molecules 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_r = 233.23
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.114
S = 1.04
2298 reflections
159 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) $[-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811025451/qm2013sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811025451/qm2013Isup3.cml

checkCIF report

Comment top

Recently, a great number of hydrazones derived from the reaction of salicylaldehyde and its derivatives with benzohydrazides (Wang et al., 2011; Hashemian et al., 2011; Singh & Singh, 2010; Ahmad et al., 2010). To the best of our knowledge, the hydrazones derived from cyanoacetohydrazide have never been reported so far. In this paper, the title new hydrazone compound, (I), is reported.

There is an intramolecular O—H···N hydrogen bond (Table 1) in the molecule of (I), Fig. 1. The non-hydrogen atoms of the compound are approximately coplanar, with mean deviation from the least-squares plane of 0.026 (3) Å. In the crystal structure, molecules are linked by N—H···O hydrogen bonds (Table 1), generating chains running along the b axis (Fig. 2).

Related literature top

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

Experimental top

The title compound was obtained by the reaction of equimolar quantities (1.0 mmol each) of 3-methoxysalicylaldehyde with cyanoacetohydrazide in methanol. Single crystals suitable for X-ray diffraction were obtained by the slow evaporation of the solution containing the compound in open air.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. Intramolecular O—H···N hydrogen bond is shown as a dashed line.
	Fig. 2. The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

2-Cyano-N'-(2-hydroxy-3-methoxybenzylidene)acetohydrazide top

Crystal data top

C₁₁H₁₁N₃O₃	D_x = 1.426 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0452P)²] where P = (F_o² + 2F_c²)/3
2298 reflections	(Δ/σ)_max < 0.001
159 parameters	Δρ_max = 0.18 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₁H₁₁N₃O₃	V = 1086.5 (5) Å³
M_r = 233.23	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.8035 (14) Å	µ = 0.11 mm⁻¹
b = 9.470 (3) Å	T = 298 K
c = 23.884 (7) Å	0.23 × 0.18 × 0.17 mm

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	2298 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1606 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.982	R_int = 0.058
6959 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	1 restraint
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.18 e Å⁻³
2298 reflections	Δρ_min = −0.22 e Å⁻³
159 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x−1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁N₃O₃
M_r	233.23
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	4.8035 (14), 9.470 (3), 23.884 (7)
V (Å³)	1086.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.23 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.976, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	6959, 2298, 1606
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.114, 1.04
No. of reflections	2298
No. of parameters	159
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.22

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.896 (10)	2.20 (2)	2.995 (3)	148 (3)
O2—H2···N1	0.82	1.91	2.626 (3)	145

Symmetry code: (i) −x−1, y+1/2, −z+1/2.

References

Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o1022. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hashemian, S., Ghaeinee, V. & Notash, B. (2011). Acta Cryst. E67, o171. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, V. P. & Singh, S. (2010). Acta Cryst. E66, o1172. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, F., Liu, D.-Y., Wang, H.-B., Meng, X.-S. & Kang, T.-G. (2011). Acta Cryst. E67, o810. Web of Science CSD CrossRef IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2001

doi:10.1107/S1600536811025451

Open

access