organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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[Wang, F., Liu, D.-Y., Wang, H.-B., Meng, X.-S. & Kang, T.-G. (2011). Acta Cryst. E67, o810.]); Hashemian et al. (2011[Hashemian, S., Ghaeinee, V. & Notash, B. (2011). Acta Cryst. E67, o171.]); Singh & Singh (2010[Singh, V. P. & Singh, S. (2010). Acta Cryst. E66, o1172.]); Ahmad et al. (2010[Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o1022.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11N3O3

  • Mr = 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[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.976, Tmax = 0.982

  • 6959 measured reflections

  • 2298 independent reflections

  • 1606 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.97 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2 (1.5 for methyl group and O) times Ueq(C).

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
[Figure 1] 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.
[Figure 2] 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
C11H11N3O3Dx = 1.426 Mg m3
Mr = 233.23Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 1239 reflections
a = 4.8035 (14) Åθ = 2.4–24.5°
b = 9.470 (3) ŵ = 0.11 mm1
c = 23.884 (7) ÅT = 298 K
V = 1086.5 (5) Å3Block, colorless
Z = 40.23 × 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 tube1606 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ω scansθmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 66
Tmin = 0.976, Tmax = 0.982k = 1211
6959 measured reflectionsl = 3026
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H 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 parametersΔρmax = 0.18 e Å3
1 restraintΔρmin = 0.22 e Å3
Crystal data top
C11H11N3O3V = 1086.5 (5) Å3
Mr = 233.23Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.8035 (14) ŵ = 0.11 mm1
b = 9.470 (3) ÅT = 298 K
c = 23.884 (7) Å0.23 × 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)
Tmin = 0.976, Tmax = 0.982Rint = 0.058
6959 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0611 restraint
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.18 e Å3
2298 reflectionsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
N10.1059 (5)0.2286 (2)0.20121 (9)0.0327 (6)
N20.2854 (5)0.2894 (2)0.23995 (10)0.0357 (6)
N30.9714 (7)0.1500 (3)0.37043 (13)0.0710 (10)
O10.4649 (5)0.0612 (2)0.06598 (9)0.0509 (6)
O20.1150 (5)0.02087 (19)0.14348 (9)0.0437 (6)
H20.00040.05800.16410.066*
O30.4697 (5)0.0798 (2)0.26659 (8)0.0458 (6)
C10.2477 (6)0.2652 (3)0.13270 (11)0.0300 (7)
C20.2719 (6)0.1226 (3)0.11849 (11)0.0324 (7)
C30.4616 (6)0.0810 (3)0.07771 (12)0.0385 (8)
C40.6298 (7)0.1801 (3)0.05190 (13)0.0415 (8)
H40.75810.15220.02490.050*
C50.6059 (7)0.3220 (3)0.06656 (13)0.0425 (8)
H50.71950.38850.04930.051*
C60.4189 (6)0.3643 (3)0.10575 (12)0.0377 (7)
H60.40410.45950.11480.045*
C70.6697 (8)0.1109 (4)0.02719 (13)0.0619 (11)
H7A0.63690.06930.00890.093*
H7B0.65780.21180.02430.093*
H7C0.85180.08480.04020.093*
C80.0503 (6)0.3143 (3)0.17435 (12)0.0351 (7)
H80.03710.41060.18170.042*
C90.4540 (6)0.2074 (3)0.27092 (11)0.0316 (7)
C100.6117 (7)0.2931 (3)0.31379 (12)0.0392 (8)
H10A0.47980.33460.33980.047*
H10B0.70740.36970.29490.047*
C110.8123 (7)0.2116 (3)0.34494 (13)0.0412 (8)
H2A0.287 (8)0.3840 (11)0.2408 (13)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0339 (14)0.0275 (12)0.0369 (14)0.0044 (12)0.0030 (13)0.0002 (11)
N20.0430 (16)0.0253 (12)0.0388 (14)0.0027 (13)0.0097 (13)0.0028 (12)
N30.083 (3)0.0503 (18)0.080 (2)0.0227 (18)0.035 (2)0.0092 (16)
O10.0569 (16)0.0422 (12)0.0537 (14)0.0071 (10)0.0123 (12)0.0065 (10)
O20.0443 (14)0.0327 (11)0.0541 (15)0.0032 (10)0.0151 (11)0.0019 (9)
O30.0572 (15)0.0251 (11)0.0550 (13)0.0026 (10)0.0130 (12)0.0022 (9)
C10.0288 (17)0.0325 (16)0.0286 (15)0.0016 (13)0.0042 (14)0.0050 (13)
C20.0312 (18)0.0338 (16)0.0322 (16)0.0022 (14)0.0034 (14)0.0037 (13)
C30.038 (2)0.0424 (17)0.0352 (17)0.0060 (15)0.0015 (15)0.0005 (15)
C40.0328 (18)0.061 (2)0.0308 (16)0.0050 (16)0.0044 (16)0.0033 (15)
C50.038 (2)0.0487 (19)0.0411 (19)0.0096 (15)0.0006 (16)0.0101 (15)
C60.0377 (18)0.0363 (15)0.0389 (17)0.0017 (15)0.0015 (16)0.0039 (14)
C70.067 (3)0.067 (2)0.052 (2)0.010 (2)0.008 (2)0.0204 (18)
C80.038 (2)0.0296 (14)0.0381 (17)0.0015 (13)0.0017 (15)0.0016 (13)
C90.0327 (18)0.0301 (16)0.0319 (16)0.0041 (13)0.0035 (14)0.0012 (13)
C100.0435 (19)0.0307 (16)0.0434 (18)0.0014 (15)0.0096 (16)0.0058 (14)
C110.047 (2)0.0310 (16)0.0454 (19)0.0010 (15)0.0064 (18)0.0085 (15)
Geometric parameters (Å, º) top
N1—C81.278 (3)C3—C41.384 (4)
N1—N21.390 (3)C4—C51.393 (4)
N2—C91.344 (4)C4—H40.9300
N2—H2A0.896 (10)C5—C61.358 (4)
N3—C111.138 (4)C5—H50.9300
O1—C31.376 (3)C6—H60.9300
O1—C71.431 (4)C7—H7A0.9600
O2—C21.361 (3)C7—H7B0.9600
O2—H20.8200C7—H7C0.9600
O3—C91.215 (3)C8—H80.9300
C1—C21.396 (4)C9—C101.510 (4)
C1—C61.404 (4)C10—C111.442 (4)
C1—C81.451 (4)C10—H10A0.9700
C2—C31.391 (4)C10—H10B0.9700
C8—N1—N2115.8 (2)C5—C6—H6119.8
C9—N2—N1120.1 (2)C1—C6—H6119.8
C9—N2—H2A124 (2)O1—C7—H7A109.5
N1—N2—H2A116 (2)O1—C7—H7B109.5
C3—O1—C7117.5 (2)H7A—C7—H7B109.5
C2—O2—H2109.5O1—C7—H7C109.5
C2—C1—C6119.1 (3)H7A—C7—H7C109.5
C2—C1—C8122.1 (2)H7B—C7—H7C109.5
C6—C1—C8118.8 (3)N1—C8—C1121.6 (3)
O2—C2—C3118.0 (2)N1—C8—H8119.2
O2—C2—C1122.1 (2)C1—C8—H8119.2
C3—C2—C1119.9 (2)O3—C9—N2124.4 (3)
O1—C3—C4124.5 (3)O3—C9—C10124.1 (3)
O1—C3—C2115.3 (3)N2—C9—C10111.4 (2)
C4—C3—C2120.1 (3)C11—C10—C9113.4 (2)
C3—C4—C5119.6 (3)C11—C10—H10A108.9
C3—C4—H4120.2C9—C10—H10A108.9
C5—C4—H4120.2C11—C10—H10B108.9
C6—C5—C4120.8 (3)C9—C10—H10B108.9
C6—C5—H5119.6H10A—C10—H10B107.7
C4—C5—H5119.6N3—C11—C10178.2 (3)
C5—C6—C1120.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O3i0.90 (1)2.20 (2)2.995 (3)148 (3)
O2—H2···N10.821.912.626 (3)145
Symmetry code: (i) x1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC11H11N3O3
Mr233.23
Crystal system, space groupOrthorhombic, P212121
Temperature (K)298
a, b, c (Å)4.8035 (14), 9.470 (3), 23.884 (7)
V3)1086.5 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.23 × 0.18 × 0.17
Data collection
DiffractometerBruker SMART 1K CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.976, 0.982
No. of measured, independent and
observed [I > 2σ(I)] reflections
6959, 2298, 1606
Rint0.058
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.114, 1.04
No. of reflections2298
No. of parameters159
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.18, 0.22

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O3i0.896 (10)2.20 (2)2.995 (3)148 (3)
O2—H2···N10.821.912.626 (3)145
Symmetry code: (i) x1, y+1/2, z+1/2.
 

References

First citationAhmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o1022.  Web of Science CSD CrossRef IUCr Journals
First citationBruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationHashemian, S., Ghaeinee, V. & Notash, B. (2011). Acta Cryst. E67, o171.  Web of Science CrossRef IUCr Journals
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSingh, V. P. & Singh, S. (2010). Acta Cryst. E66, o1172.  Web of Science CSD CrossRef IUCr Journals
First citationWang, 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

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ISSN: 2056-9890
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