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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1789.
Published online 2008 August 20. doi:  10.1107/S1600536808026287
PMCID: PMC2960596

N′-(3-Phenyl­allyl­idene)isonicotino­hydrazide

Abstract

The asymmetric unit of the title compound, C15H13N3O, contains two similar mol­ecules. Each mol­ecule is non-planar, as indicated by the dihedral angles between the pyridine and benzene rings of 45.2 (2) and 56.6 (2)°. The crystal structure is consolidated by inter­molecular N—H(...)O hydrogen bonds.

Related literature

For related literature, see: Kahwa et al. (1986 [triangle]); Qian et al. (2006 [triangle]); Santos et al. (2001 [triangle]).

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Object name is e-64-o1789-scheme1.jpg

Experimental

Crystal data

  • C15H13N3O
  • M r = 251.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1789-efi1.jpg
  • a = 12.608 (8) Å
  • b = 11.023 (7) Å
  • c = 10.044 (7) Å
  • β = 105.94 (3)°
  • V = 1342.2 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 291 (2) K
  • 0.30 × 0.26 × 0.24 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.98, T max = 0.98
  • 11645 measured reflections
  • 3110 independent reflections
  • 2784 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.134
  • S = 1.01
  • 3110 reflections
  • 349 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SMART; data reduction: SAINT (Bruker, 2000 [triangle]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; 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/S1600536808026287/ez2136sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026287/ez2136Isup2.hkl

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

supplementary crystallographic information

Comment

Interest in the chemistry of Schiff bases has increased considerably in recent years, mainly due to their novel properties and their application in the development of various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). Structural information of Schiff base derivatives is useful in studying their coordination chemisty. As part of our research, we have synthesized the title compound (I) and report its crystal structure here.

The molecular structure is shown in Fig. 1. Each molecule is non-planar, with dihedral angles of 45.2 (2) and 56.6 (2)° between the pyridine ring and the benzene ring for the two molecules. Bond lengths and angles agree with those found for isonicotinohydrazide derivatives (Qian et al., 2006).

Intermolecular N—H···O hydrogen bonds link pairs of molecules.

Experimental

Pyridine-4-carboxylic acid hydrazide (1 mmol, 0.137 g) was dissolved in anhydrous methanol, whereafter H2SO4 (98%, 0.5 ml) was added and the mixture was stirred for several minutes at 351 K. A solution of cinnamaldehyde (1 mmol, 0.132 g) in methanol (8 ml) was then added dropwise and the mixture was stirred under reflux for 2 h. The product was isolated and recrystallized from dichloromethane, brown single crystals of (I) were obtained after 2 d.

Refinement

H atoms on N2 and N5 were identified by difference Fourier map and refined isotropically. All other H atoms were placed in calculated positions, with C-H=0.93Å (aromatic), N-H = 0.96Å, and with Uiso(H)=1.2Ueq(C,N). In the absence of significant anomalous scattering effects, 2686 Friedel pairs have been merged.

Figures

Fig. 1.
ORTEP plot of (I) showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C15H13N3OF000 = 528
Mr = 251.28Dx = 1.244 Mg m3
Monoclinic, PcMo Kα radiation λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 940 reflections
a = 12.608 (8) Åθ = 2.5–20.5º
b = 11.023 (7) ŵ = 0.08 mm1
c = 10.044 (7) ÅT = 291 (2) K
β = 105.94 (3)ºBlock, brown
V = 1342.2 (15) Å30.30 × 0.26 × 0.24 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer3110 independent reflections
Radiation source: sealed tube2784 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.044
T = 291(2) Kθmax = 27.7º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −16→16
Tmin = 0.98, Tmax = 0.98k = −13→14
11645 measured reflectionsl = −13→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134  w = 1/[σ2(Fo2) + (0.05P)2 + 0.88P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3110 reflectionsΔρmax = 0.20 e Å3
349 parametersΔρmin = −0.29 e Å3
2 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
C11.2011 (4)0.4816 (5)0.8674 (5)0.0472 (10)
H11.22380.55620.84200.057*
C21.2551 (4)0.4303 (4)0.9917 (5)0.0457 (10)
H21.31390.47161.05050.055*
C31.2239 (4)0.3174 (4)1.0323 (5)0.0417 (9)
H31.26090.28381.11730.050*
C41.1362 (4)0.2566 (4)0.9422 (4)0.0418 (10)
H41.11480.18090.96660.050*
C51.0805 (4)0.3081 (5)0.8167 (4)0.0469 (11)
H51.02190.26720.75710.056*
C61.1126 (3)0.4217 (4)0.7798 (5)0.0421 (9)
C71.0508 (3)0.4875 (4)0.6585 (5)0.0426 (10)
H71.06940.56720.64460.051*
C80.9646 (4)0.4321 (4)0.5637 (5)0.0436 (10)
H80.94510.35210.57470.052*
C90.9049 (4)0.5050 (4)0.4446 (4)0.0435 (10)
H90.91750.58700.43330.052*
C100.6810 (4)0.4686 (4)0.1451 (4)0.0391 (9)
C110.5998 (4)0.5425 (4)0.0516 (4)0.0438 (10)
C120.5471 (3)0.5017 (4)−0.0823 (4)0.0356 (8)
H120.55870.4233−0.10930.043*
C130.4793 (4)0.5778 (4)−0.1716 (5)0.0413 (9)
H130.44380.5497−0.25990.050*
C140.5136 (4)0.7372 (4)−0.0082 (4)0.0427 (9)
H140.50250.81650.01650.051*
C150.5845 (3)0.6620 (4)0.0872 (4)0.0432 (10)
H150.62160.69140.17430.052*
C160.4052 (4)0.0511 (4)−0.2985 (4)0.0424 (9)
H160.4482−0.0181−0.27280.051*
C170.3238 (3)0.0544 (4)−0.4232 (4)0.0400 (9)
H170.3127−0.0128−0.48140.048*
C180.2588 (4)0.1560 (4)−0.4623 (5)0.0455 (10)
H180.20390.1569−0.54590.055*
C190.2761 (4)0.2580 (4)−0.3752 (4)0.0417 (9)
H190.23280.3269−0.40150.050*
C200.3577 (3)0.2565 (4)−0.2498 (4)0.0356 (8)
H200.36890.3242−0.19230.043*
C210.4226 (4)0.1536 (4)−0.2104 (4)0.0462 (10)
C220.5026 (4)0.1586 (4)−0.0775 (5)0.0462 (10)
H220.50190.2227−0.01750.055*
C230.5807 (4)0.0677 (4)−0.0391 (4)0.0433 (10)
H230.59310.0067−0.09700.052*
C240.6411 (3)0.0828 (4)0.1081 (4)0.0398 (9)
H240.64230.15330.15940.048*
C250.8300 (4)−0.1108 (5)0.3489 (5)0.0502 (11)
C260.8954 (4)−0.0909 (4)0.4904 (5)0.0441 (10)
C270.9750 (4)−0.0014 (4)0.5288 (5)0.0405 (9)
H270.98220.05700.46500.049*
C281.0442 (4)0.0012 (5)0.6632 (5)0.0505 (11)
H281.09650.06230.69040.061*
C290.9555 (3)−0.1774 (4)0.7183 (4)0.0421 (9)
H290.9483−0.23600.78190.051*
C300.8865 (3)−0.1796 (3)0.5848 (4)0.0337 (8)
H300.8341−0.24070.55820.040*
N10.8334 (3)0.4414 (3)0.3586 (4)0.0397 (8)
N20.7663 (3)0.5206 (4)0.2548 (4)0.0423 (9)
H2A0.777 (4)0.598 (5)0.259 (5)0.051*
N30.4603 (3)0.6964 (3)−0.1372 (3)0.0392 (8)
N40.6918 (3)−0.0162 (3)0.1548 (4)0.0424 (8)
N50.7800 (3)−0.0023 (3)0.2797 (3)0.0368 (8)
H5A0.833 (4)0.042 (4)0.259 (5)0.044*
N61.0342 (3)−0.0891 (4)0.7569 (4)0.0491 (9)
O10.6774 (2)0.3578 (3)0.1322 (3)0.0434 (7)
O20.8172 (2)−0.2090 (3)0.2914 (3)0.0440 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.042 (2)0.052 (3)0.051 (3)−0.006 (2)0.019 (2)0.004 (2)
C20.042 (2)0.048 (2)0.049 (3)−0.0034 (19)0.017 (2)−0.011 (2)
C30.043 (2)0.044 (2)0.043 (2)0.0020 (18)0.0214 (19)−0.0022 (18)
C40.048 (2)0.042 (2)0.042 (2)−0.0146 (18)0.0227 (19)0.0100 (17)
C50.037 (2)0.071 (3)0.035 (2)−0.014 (2)0.0134 (17)−0.010 (2)
C60.0332 (18)0.050 (2)0.046 (2)0.0070 (18)0.0149 (17)−0.0088 (19)
C70.037 (2)0.043 (2)0.054 (3)0.0071 (18)0.0238 (19)−0.014 (2)
C80.040 (2)0.041 (2)0.053 (3)0.0142 (18)0.0167 (19)0.0057 (19)
C90.051 (2)0.050 (2)0.0264 (19)0.003 (2)0.0053 (17)−0.0123 (18)
C100.044 (2)0.036 (2)0.040 (2)−0.0233 (18)0.0151 (17)0.0063 (17)
C110.054 (3)0.041 (2)0.038 (2)−0.006 (2)0.0163 (19)−0.0013 (18)
C120.0331 (19)0.038 (2)0.043 (2)0.0074 (16)0.0221 (16)−0.0088 (16)
C130.042 (2)0.046 (2)0.040 (2)−0.0041 (19)0.0172 (18)−0.0042 (18)
C140.048 (2)0.042 (2)0.037 (2)−0.0053 (19)0.0103 (18)−0.0103 (18)
C150.041 (2)0.056 (3)0.032 (2)−0.0076 (19)0.0092 (17)−0.0133 (18)
C160.051 (2)0.045 (2)0.031 (2)−0.005 (2)0.0121 (17)0.0038 (17)
C170.036 (2)0.046 (2)0.036 (2)−0.0121 (17)0.0074 (17)−0.0079 (17)
C180.047 (2)0.047 (2)0.043 (2)−0.0120 (19)0.0108 (19)−0.013 (2)
C190.049 (2)0.043 (2)0.034 (2)−0.0036 (19)0.0128 (18)−0.0051 (17)
C200.0386 (19)0.036 (2)0.037 (2)−0.0144 (16)0.0175 (16)0.0037 (16)
C210.055 (3)0.051 (3)0.037 (2)−0.004 (2)0.0198 (19)0.0099 (19)
C220.046 (2)0.044 (2)0.051 (3)0.0147 (19)0.018 (2)−0.0061 (19)
C230.044 (2)0.045 (2)0.040 (2)0.0018 (19)0.0095 (18)−0.0135 (18)
C240.0314 (18)0.052 (2)0.037 (2)−0.0043 (17)0.0113 (16)−0.0110 (18)
C250.050 (2)0.052 (3)0.054 (3)0.013 (2)0.022 (2)0.003 (2)
C260.047 (2)0.045 (2)0.049 (3)0.003 (2)0.028 (2)0.005 (2)
C270.038 (2)0.046 (2)0.044 (2)0.0001 (17)0.0225 (18)0.0012 (18)
C280.050 (2)0.063 (3)0.038 (2)−0.011 (2)0.0126 (19)−0.009 (2)
C290.040 (2)0.047 (2)0.044 (2)0.0067 (18)0.0202 (18)−0.0077 (18)
C300.0285 (16)0.0339 (19)0.044 (2)0.0102 (14)0.0190 (15)−0.0027 (16)
N10.0374 (17)0.0327 (17)0.0451 (19)−0.0052 (14)0.0045 (14)0.0001 (14)
N20.0305 (17)0.045 (2)0.0435 (19)−0.0151 (15)−0.0034 (14)0.0138 (16)
N30.0488 (19)0.0410 (19)0.0321 (17)0.0031 (16)0.0182 (14)0.0002 (15)
N40.055 (2)0.0406 (19)0.0303 (17)−0.0081 (17)0.0093 (16)−0.0039 (15)
N50.0338 (17)0.0399 (18)0.0350 (18)−0.0151 (14)0.0064 (14)−0.0011 (14)
N60.043 (2)0.062 (2)0.049 (2)−0.0020 (18)0.0230 (17)−0.0041 (19)
O10.0396 (15)0.0449 (17)0.0474 (17)−0.0096 (13)0.0152 (13)−0.0059 (13)
O20.0434 (15)0.0455 (17)0.0413 (16)0.0001 (13)0.0084 (12)0.0034 (14)

Geometric parameters (Å, °)

C1—C21.369 (7)C16—H160.9300
C1—C61.385 (7)C17—C181.379 (7)
C1—H10.9300C17—H170.9300
C2—C31.400 (6)C18—C191.405 (6)
C2—H20.9300C18—H180.9300
C3—C41.394 (6)C19—C201.391 (6)
C3—H30.9300C19—H190.9300
C4—C51.386 (6)C20—C211.391 (6)
C4—H40.9300C20—H200.9300
C5—C61.397 (7)C21—C221.437 (6)
C5—H50.9300C22—C231.383 (6)
C6—C71.447 (7)C22—H220.9300
C7—C81.375 (7)C23—C241.475 (6)
C7—H70.9300C23—H230.9300
C8—C91.467 (6)C24—N41.287 (6)
C8—H80.9300C24—H240.9300
C9—N11.273 (5)C25—O21.216 (6)
C9—H90.9300C25—N51.439 (6)
C10—O11.228 (5)C25—C261.451 (7)
C10—N21.432 (5)C26—C271.385 (6)
C10—C111.437 (6)C26—C301.388 (6)
C11—C151.393 (6)C27—C281.391 (7)
C11—C121.400 (6)C27—H270.9300
C12—C131.347 (6)C28—N61.399 (7)
C12—H120.9300C28—H280.9300
C13—N31.390 (6)C29—N61.368 (6)
C13—H130.9300C29—C301.384 (6)
C14—N31.362 (5)C29—H290.9300
C14—C151.390 (7)C30—H300.9300
C14—H140.9300N1—N21.442 (5)
C15—H150.9300N2—H2A0.86 (5)
C16—C171.385 (6)N4—N51.437 (5)
C16—C211.415 (7)N5—H5A0.90 (5)
C2—C1—C6119.7 (5)C16—C17—H17119.6
C2—C1—H1120.1C17—C18—C19119.6 (4)
C6—C1—H1120.1C17—C18—H18120.2
C1—C2—C3121.6 (4)C19—C18—H18120.2
C1—C2—H2119.2C20—C19—C18120.3 (4)
C3—C2—H2119.2C20—C19—H19119.9
C4—C3—C2118.4 (4)C18—C19—H19119.9
C4—C3—H3120.8C21—C20—C19119.9 (4)
C2—C3—H3120.8C21—C20—H20120.1
C5—C4—C3120.5 (4)C19—C20—H20120.1
C5—C4—H4119.8C20—C21—C16119.7 (4)
C3—C4—H4119.8C20—C21—C22116.2 (4)
C4—C5—C6119.9 (4)C16—C21—C22124.1 (4)
C4—C5—H5120.1C23—C22—C21119.7 (4)
C6—C5—H5120.1C23—C22—H22120.1
C1—C6—C5120.0 (4)C21—C22—H22120.1
C1—C6—C7116.7 (5)C22—C23—C24109.2 (4)
C5—C6—C7123.0 (4)C22—C23—H23125.4
C8—C7—C6120.0 (4)C24—C23—H23125.4
C8—C7—H7120.0N4—C24—C23109.7 (4)
C6—C7—H7120.0N4—C24—H24125.1
C7—C8—C9116.9 (4)C23—C24—H24125.1
C7—C8—H8121.5O2—C25—N5121.8 (5)
C9—C8—H8121.5O2—C25—C26124.4 (4)
N1—C9—C8111.1 (4)N5—C25—C26113.8 (4)
N1—C9—H9124.4C27—C26—C30120.0 (4)
C8—C9—H9124.4C27—C26—C25123.7 (4)
O1—C10—N2118.5 (4)C30—C26—C25115.6 (4)
O1—C10—C11119.7 (4)C26—C27—C28119.9 (4)
N2—C10—C11121.7 (4)C26—C27—H27120.1
C15—C11—C12119.1 (4)C28—C27—H27120.1
C15—C11—C10119.5 (4)C27—C28—N6119.3 (4)
C12—C11—C10120.7 (4)C27—C28—H28120.3
C13—C12—C11119.1 (4)N6—C28—H28120.3
C13—C12—H12120.4N6—C29—C30120.1 (4)
C11—C12—H12120.4N6—C29—H29120.0
C12—C13—N3122.8 (4)C30—C29—H29120.0
C12—C13—H13118.6C29—C30—C26120.2 (4)
N3—C13—H13118.6C29—C30—H30119.9
N3—C14—C15121.0 (4)C26—C30—H30119.9
N3—C14—H14119.5C9—N1—N2108.8 (4)
C15—C14—H14119.5C10—N2—N1118.8 (3)
C14—C15—C11119.7 (4)C10—N2—H2A121 (3)
C14—C15—H15120.1N1—N2—H2A121 (3)
C11—C15—H15120.1C14—N3—C13118.2 (4)
C17—C16—C21119.6 (4)C24—N4—N5114.5 (3)
C17—C16—H16120.2N4—N5—C25117.7 (4)
C21—C16—H16120.2N4—N5—H5A108 (3)
C18—C17—C16120.9 (4)C25—N5—H5A108 (3)
C18—C17—H17119.6C29—N6—C28120.5 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.86 (5)2.19 (5)3.050 (6)174 (3)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2136).

References

  • Bruker (2000). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Kahwa, I. A., Selbin, I., Hsieh, T. C. Y. & Laine, R. A. (1986). Inorg. Chim. Acta, 118, 179–185.
  • Qian, H.-Y., Yin, Z.-G., Jia, J., Liu, S.-M. & Feng, L.-Q. (2006). Acta Cryst. E62, o3623–o3624.
  • Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838–844.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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