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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o892.
Published online 2010 March 20. doi:  10.1107/S1600536810010020
PMCID: PMC2984034

N′-(2-Hydr­oxy-4-methoxy­benzyl­idene)isonicotinohydrazide

Abstract

The title compound, C14H13N3O3, was synthesized by the condensation reaction of 2-hydr­oxy-4-methoxy­benzaldehyde with isonicotinohydrazide in a methanol solution. The mol­ecule of the compound displays a trans configuration with respect to the C=N and C—N bonds. The dihedral angle between the benzene and the pyridine rings is 27.3 (2)°. In the crystal, mol­ecules are linked by N—H(...)N inter­actions into zigzag chains with graph-set notation C(7) along [010]. An intra­molecular O—H(...)N hydrogen bond is observed.

Related literature

For Schiff base compounds, see: Fan et al. (2007 [triangle]); Kim et al. (2005 [triangle]); Nimitsiriwat et al. (2004 [triangle]). For their biological activity, see: Chen et al. (1997 [triangle]); Ren et al. (2002 [triangle]). For related structures, see: Mohd Lair et al. (2009 [triangle]); Fun et al. (2008 [triangle]); Yang (2008 [triangle]); Zhi (2008 [triangle], 2009 [triangle]); Zhi & Yang (2007 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o892-scheme1.jpg

Experimental

Crystal data

  • C14H13N3O3
  • M r = 271.27
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o892-efi1.jpg
  • a = 8.4704 (11) Å
  • b = 10.6866 (15) Å
  • c = 14.848 (2) Å
  • β = 104.929 (5)°
  • V = 1298.7 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 K
  • 0.17 × 0.15 × 0.15 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.983, T max = 0.985
  • 7591 measured reflections
  • 2814 independent reflections
  • 2148 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.107
  • S = 1.05
  • 2814 reflections
  • 186 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010020/bx2271sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010020/bx2271Isup2.hkl

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

Acknowledgments

Financial support from the Third Affiliated Hospital of Suzhou University is acknowledged.

supplementary crystallographic information

Comment

Considerable interest has been focused on the Schiff base compounds (Fan et al., 2007; Kim et al., 2005; Nimitsiriwat et al., 2004). Some of the compounds have been found to have excellent pharmacological and antibacterial activity (Chen et al., 1997; Ren et al., 2002). we report here, the crystal structure of the title new Schiff base compound, Fig. 1, derived from the condensation reaction of 2-hydroxy-4-methoxybenzaldehyde with isonicotinohydrazide is reported. The molecular structure of the title compound displays a trans configuration with respect to the C═N and C–N bonds. There is an intramolecular O—H···N hydrogen bond in the molecule. The dihedral angle between the benzene ring and the pyridine ring is 27.3 (2)°. All the bond lengths are within normal ranges and comparable to those in other similar compounds (Mohd Lair et al., 2009; Fun et al., 2008; Yang, 2008; Zhi, 2008; Zhi & Yang, 2007; Zhi, 2009). In the crystal, molecules are linked by interactions N—H···N into zigzag chains with graph-set notation C(7) along [010] (Bernstein, et al., 1995 ). An intramolecular O—H···N hydrogen bond is observed. (Table 1 and Fig. 2).

Experimental

2-Hydroxy-4-methoxybenzaldehyde (0.01 mol, 1.52 g) and isonicotinohydrazide (0.01 mol, 1.37 g) were dissolved in a methanol solution (50 ml). The mixture was stirred at room temperature to give a clear colorless solution. Crystals of the title compound were formed by gradual evaporation of the solvent for a week at room temperature.

Refinement

H2 atom was located in a difference map and refined with N–H distance restrained to 0.90 (1) Å. All other H atoms were positioned geometrically [C–H = 0.93-0.96 Å, O–H = 0.82 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O1 and C14).

Figures

Fig. 1.
The structure of the title compound at the 30% probability level. Intramolecular O—H···N hydrogen bond is shown as a dashed line.
Fig. 2.
Molecular packing of the title compound, viewed along the a axis. Intermolecular hydrogen bonds are shown as dashed lines.

Crystal data

C14H13N3O3F(000) = 568
Mr = 271.27Dx = 1.387 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.4704 (11) ÅCell parameters from 2534 reflections
b = 10.6866 (15) Åθ = 2.4–29.9°
c = 14.848 (2) ŵ = 0.10 mm1
β = 104.929 (5)°T = 298 K
V = 1298.7 (3) Å3Block, colourless
Z = 40.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer2814 independent reflections
Radiation source: fine-focus sealed tube2148 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→10
Tmin = 0.983, Tmax = 0.985k = −11→13
7591 measured reflectionsl = −18→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0491P)2 + 0.2097P] where P = (Fo2 + 2Fc2)/3
2814 reflections(Δ/σ)max < 0.001
186 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = −0.17 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)

xyzUiso*/Ueq
N10.10385 (14)0.87232 (11)0.12848 (8)0.0425 (3)
N20.01859 (14)0.78408 (11)0.16392 (8)0.0422 (3)
N3−0.26459 (16)0.40486 (11)0.24523 (9)0.0491 (3)
O10.28189 (15)0.93517 (9)0.01927 (8)0.0554 (3)
H10.22840.88810.04360.083*
O20.12526 (15)0.62775 (10)0.09488 (9)0.0624 (3)
O30.40498 (14)1.36738 (9)0.00218 (8)0.0550 (3)
C10.17894 (16)1.08276 (12)0.11284 (10)0.0404 (3)
C20.26792 (16)1.05413 (12)0.04800 (9)0.0386 (3)
C30.34625 (17)1.14692 (12)0.01077 (10)0.0410 (3)
H30.40721.1263−0.03100.049*
C40.33345 (17)1.27035 (12)0.03599 (10)0.0421 (3)
C50.24469 (19)1.30187 (14)0.09935 (12)0.0518 (4)
H50.23561.38500.11590.062*
C60.17066 (19)1.20882 (14)0.13711 (11)0.0512 (4)
H60.11291.23010.18030.061*
C70.09706 (17)0.98671 (13)0.15257 (10)0.0446 (3)
H70.03931.00820.19580.054*
C80.03539 (16)0.66264 (13)0.14180 (9)0.0410 (3)
C9−0.06727 (16)0.57305 (12)0.17959 (9)0.0365 (3)
C10−0.12509 (18)0.46540 (13)0.13050 (10)0.0437 (3)
H10−0.09900.44720.07480.052*
C11−0.22227 (19)0.38542 (14)0.16569 (11)0.0493 (4)
H11−0.26070.31350.13190.059*
C12−0.20463 (18)0.50811 (13)0.29267 (10)0.0454 (3)
H12−0.23040.52310.34890.054*
C13−0.10710 (17)0.59344 (12)0.26321 (9)0.0395 (3)
H13−0.06840.66380.29890.047*
C140.4899 (2)1.34231 (15)−0.06713 (12)0.0585 (4)
H14A0.58171.2890−0.04150.088*
H14B0.52761.4196−0.08730.088*
H14C0.41771.3015−0.11930.088*
H2−0.0540 (19)0.8096 (18)0.1945 (12)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0453 (7)0.0384 (6)0.0492 (7)−0.0015 (5)0.0219 (5)0.0052 (5)
N20.0459 (7)0.0376 (6)0.0506 (7)−0.0014 (5)0.0261 (5)0.0030 (5)
N30.0577 (8)0.0419 (7)0.0544 (7)−0.0031 (6)0.0266 (6)0.0045 (6)
O10.0798 (8)0.0316 (5)0.0704 (7)−0.0041 (5)0.0477 (6)−0.0036 (5)
O20.0732 (7)0.0502 (6)0.0831 (8)−0.0044 (5)0.0549 (7)−0.0083 (6)
O30.0653 (7)0.0335 (5)0.0721 (7)−0.0032 (5)0.0281 (6)0.0067 (5)
C10.0385 (7)0.0357 (7)0.0496 (8)0.0020 (6)0.0161 (6)0.0012 (6)
C20.0426 (7)0.0323 (7)0.0424 (7)0.0012 (5)0.0135 (6)0.0006 (6)
C30.0459 (7)0.0371 (7)0.0429 (7)0.0003 (6)0.0167 (6)0.0019 (6)
C40.0420 (7)0.0330 (7)0.0497 (8)0.0006 (6)0.0091 (6)0.0053 (6)
C50.0568 (9)0.0310 (7)0.0722 (10)0.0026 (6)0.0247 (8)−0.0039 (7)
C60.0523 (9)0.0426 (8)0.0665 (10)0.0040 (6)0.0294 (8)−0.0051 (7)
C70.0439 (8)0.0442 (8)0.0516 (8)0.0013 (6)0.0230 (7)0.0001 (6)
C80.0429 (7)0.0412 (8)0.0436 (7)0.0006 (6)0.0198 (6)0.0002 (6)
C90.0361 (7)0.0347 (7)0.0416 (7)0.0045 (5)0.0155 (6)0.0028 (5)
C100.0521 (8)0.0404 (7)0.0445 (8)0.0008 (6)0.0231 (7)−0.0031 (6)
C110.0574 (9)0.0406 (8)0.0541 (9)−0.0066 (7)0.0217 (7)−0.0048 (7)
C120.0557 (9)0.0456 (8)0.0408 (8)0.0036 (7)0.0231 (7)0.0041 (6)
C130.0461 (8)0.0366 (7)0.0380 (7)0.0019 (6)0.0148 (6)−0.0003 (6)
C140.0664 (10)0.0444 (9)0.0713 (11)−0.0039 (7)0.0301 (9)0.0107 (8)

Geometric parameters (Å, °)

N1—C71.2791 (18)C4—C51.388 (2)
N1—N21.3724 (15)C5—C61.370 (2)
N2—C81.3552 (18)C5—H50.9300
N2—H20.896 (9)C6—H60.9300
N3—C111.3358 (19)C7—H70.9300
N3—C121.3369 (19)C8—C91.4963 (18)
O1—C21.3558 (16)C9—C101.3823 (19)
O1—H10.8200C9—C131.3852 (18)
O2—C81.2153 (16)C10—C111.379 (2)
O3—C41.3606 (16)C10—H100.9300
O3—C141.4247 (19)C11—H110.9300
C1—C61.401 (2)C12—C131.3753 (19)
C1—C21.4009 (19)C12—H120.9300
C1—C71.4468 (19)C13—H130.9300
C2—C31.3849 (19)C14—H14A0.9600
C3—C41.3831 (19)C14—H14B0.9600
C3—H30.9300C14—H14C0.9600
C7—N1—N2118.91 (12)N1—C7—H7119.9
C8—N2—N1117.81 (11)C1—C7—H7119.9
C8—N2—H2122.9 (13)O2—C8—N2123.59 (13)
N1—N2—H2118.9 (13)O2—C8—C9121.93 (13)
C11—N3—C12116.24 (12)N2—C8—C9114.48 (11)
C2—O1—H1109.5C10—C9—C13117.94 (12)
C4—O3—C14118.62 (11)C10—C9—C8119.73 (12)
C6—C1—C2117.28 (13)C13—C9—C8122.33 (12)
C6—C1—C7121.09 (13)C11—C10—C9118.74 (13)
C2—C1—C7121.63 (12)C11—C10—H10120.6
O1—C2—C3117.14 (12)C9—C10—H10120.6
O1—C2—C1121.81 (12)N3—C11—C10124.11 (14)
C3—C2—C1121.05 (12)N3—C11—H11117.9
C4—C3—C2119.72 (13)C10—C11—H11117.9
C4—C3—H3120.1N3—C12—C13123.88 (13)
C2—C3—H3120.1N3—C12—H12118.1
O3—C4—C3123.60 (13)C13—C12—H12118.1
O3—C4—C5115.81 (12)C12—C13—C9119.06 (13)
C3—C4—C5120.58 (13)C12—C13—H13120.5
C6—C5—C4119.07 (13)C9—C13—H13120.5
C6—C5—H5120.5O3—C14—H14A109.5
C4—C5—H5120.5O3—C14—H14B109.5
C5—C6—C1122.28 (14)H14A—C14—H14B109.5
C5—C6—H6118.9O3—C14—H14C109.5
C1—C6—H6118.9H14A—C14—H14C109.5
N1—C7—C1120.22 (13)H14B—C14—H14C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···N3i0.90 (1)2.22 (1)3.1000 (17)169 (2)
O1—H1···N10.821.852.5720 (15)146

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2271).

References

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