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

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ISSN: 2056-9890

4-{(E)-[2-(Pyridin-3-ylcarbon­yl)hydrazinyl­­idene]meth­yl}phenyl acetate

aDepartment of Chemistry, Christ University, Hosur Road, Bangalore 560 029, India, bDepartment of Chemistry, Faculty of Science, Eastern University, Sri Lanka, Chenkalady, Sri Lanka, and cDepartment of Applied Chemistry, Cochin University of Science and Technology, Kochi 682 022, India
*Correspondence e-mail: eesans@yahoo.com

(Received 25 August 2013; accepted 9 September 2013; online 18 September 2013)

The title compound, C15H13N3O3, exists in the E conformation with respect to the azo­methane C=N double bond. The pyridyl and phenyl rings form dihedral angles of 35.67 (8) and 36.65 (7)°, respectively with the central C(=O)N2C unit. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds connect the mol­ecules into chains along the b axis. Another C—H⋯O inter­action connects mol­ecules along the c-axis direction, forming layers.

Related literature

For biological applications of benzohydrazones and their derivatives, see: Sreeja et al. (2004[Sreeja, P. B., Kurup, M. R. P., Kishore, A. & Jasmin, C. (2004). Polyhedron, 23, 575-581.]); Rakha et al. (1996[Rakha, T. H., Ibrahim, K. M., Abdallah, A. M. & Hassanian, M. M. (1996). Synth. React. Inorg. Met.-Org. Chem. 26, 1113-1123.]); Takahama (1996[Takahama, U. (1996). Physiol. Plant. 98, 731-736.]). For the synthesis of related compounds, see: Emmanuel et al. (2011[Emmanuel, J., Sithambaresan, M. & Kurup, M. R. P. (2011). Acta Cryst. E67, o3267.]). For related structures, see: Reshma et al. (2012[Reshma, P. R., Sithambaresan, M. & Kurup, M. R. P. (2012). Acta Cryst. E68, o2821-o2822.]).

[Scheme 1]

Experimental

Crystal data
  • C15H13N3O3

  • Mr = 283.28

  • Monoclinic, P 21 /n

  • a = 16.347 (4) Å

  • b = 5.0859 (10) Å

  • c = 18.408 (5) Å

  • β = 115.311 (9)°

  • V = 1383.6 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 296 K

  • 0.50 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.953, Tmax = 0.976

  • 9585 measured reflections

  • 3325 independent reflections

  • 2288 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.140

  • S = 1.04

  • 3325 reflections

  • 195 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2′⋯O1i 0.87 (1) 2.08 (1) 2.9107 (18) 162 (2)
C7—H7⋯O1i 0.93 2.48 3.251 (2) 140
C15—H15C⋯O3ii 0.96 2.55 3.469 (4) 161
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Hydrazone derivatives show excellent spectrum of biological activities (Sreeja et al., 2004). The chemical and pharmacological properties of aroylhydrazones have been extensively investigated recently owing to their potential application as antineoplastic, antiviral and antiinflammatory agents (Rakha et al., 1996; Takahama, 1996).

The compound (Fig. 1) crystallizes in the monoclinic space group P21/n. This molecule adopts an E configuration with respect to the C7=N3 bond and it exists in the amido form with a C6=O1 bond length of 1.2277 (18) Å which is very close to the reported C=O bond length of a related structure (Reshma et al., 2012). The O1 and N2 atoms are in a Z configuration with respect to C6–N2 having a torsion angle of 9.9 (3)°. The central C(=O)N2C unit has dihedral angles of 35.67 (8) and 36.65 (7)°, respectively with the pyridyl and the phenyl rings.

There is a classical intermolecular N–H···O hydrogen bond interaction between the H atom attached at the N2 and O1 atom of neighbouring molecule with D···A distance of 2.9107 (18) Å and two C–H···O hydrogen bond interactions (Fig. 2) between the H atoms attached at the C7 & C15 and O1 & O3 atoms of neighbouring molecules with D···A distances of 3.251 (2) and 3.469 (4) Å, respectively. The classical hydrogen bond together with C–H···O interaction connect the molecules along b axis while the other C–H···O interaction chain the molecules along c axis in the crystal system. Four types of C–H···π interactions are also found in the molecular system (Fig. 3) with H···Cg distances of 3.1267, 3.2825, 3.3911 and 3.1984 Å forming a three-dimensional-supramolecuar architecture together with the intermolecular hydrogen bonding interactions. Although there are very weak short ring interactions found in the crystal system, they are not significant to support the network since centroid-centroid distances are above 4 Å. Fig. 4 shows a packing diagram of the title compound viewed along the b axis.

Related literature top

For biological applications of benzohydrazones and their derivatives, see: Sreeja et al. (2004); Rakha et al. (1996); Takahama (1996). For the synthesis of related compounds, see: Emmanuel et al. (2011). For related structures, see: Reshma et al. (2012).

Experimental top

The title compound was prepared by adapting a reported procedure (Emmanuel et al., 2011). A solution of pyridine-3-carbohydrazide (0.137 g, 1 mmol) in ethanol (10 ml) was mixed with a methanolic solution (10 ml) of 4-formylphenyl acetate (0.164 g, 1 mmol). The mixture was refluxed for 6 h after adding few drops of glacial acetic acid and then cooled to room temperature. The formed crystals were collected, washed with few drops of methanol and dried over P4O10 in vacuo. Colorless block shaped crystals, suitable for SXRD studies, were obtained after slow evaporation of the solution in air for a few days.

Refinement top

The atom H2' was located from a difference Fourier map and N—H3' distance was restrained to 0.88±0.01 Å. The H atoms on C were placed in calculated positions, guided by difference maps, with C–H bond distances 0.93–0.96 Å. H atoms were assigned as Uiso(H)=1.2Ueq(carrier) or 1.5Ueq (methyl C). Omitted owing to bad disagreement were the reflections (0 0 2) and (-1 0 1).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. ORTEP view of the title compound drawn with 50% probability displacement ellipsoids for the non-H atoms.
[Figure 2] Fig. 2. Hydrogen-bonding interactions in the crystal structure of C15H13N3O3.
[Figure 3] Fig. 3. π···π interactions in the crystal structure of C15H13N3O3.
[Figure 4] Fig. 4. Packing diagram of the compound along the b axis.
4-{(E)-[2-(Pyridin-3-ylcarbonyl)hydrazinylidene]methyl}phenyl acetate top
Crystal data top
C15H13N3O3F(000) = 592
Mr = 283.28Dx = 1.360 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2983 reflections
a = 16.347 (4) Åθ = 2.8–26.9°
b = 5.0859 (10) ŵ = 0.10 mm1
c = 18.408 (5) ÅT = 296 K
β = 115.311 (9)°Block, colorless
V = 1383.6 (6) Å30.50 × 0.30 × 0.25 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3325 independent reflections
Radiation source: fine-focus sealed tube2288 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
Detector resolution: 8.33 pixels mm-1θmax = 28.0°, θmin = 2.2°
ω and ϕ scanh = 2119
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
k = 66
Tmin = 0.953, Tmax = 0.976l = 2324
9585 measured reflections
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0632P)2 + 0.3098P]
where P = (Fo2 + 2Fc2)/3
3325 reflections(Δ/σ)max < 0.001
195 parametersΔρmax = 0.31 e Å3
1 restraintΔρmin = 0.25 e Å3
Crystal data top
C15H13N3O3V = 1383.6 (6) Å3
Mr = 283.28Z = 4
Monoclinic, P21/nMo Kα radiation
a = 16.347 (4) ŵ = 0.10 mm1
b = 5.0859 (10) ÅT = 296 K
c = 18.408 (5) Å0.50 × 0.30 × 0.25 mm
β = 115.311 (9)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3325 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
2288 reflections with I > 2σ(I)
Tmin = 0.953, Tmax = 0.976Rint = 0.023
9585 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0491 restraint
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.31 e Å3
3325 reflectionsΔρmin = 0.25 e Å3
195 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
O10.62319 (9)0.2235 (2)0.00860 (7)0.0554 (4)
O20.64307 (10)0.4099 (3)0.44141 (7)0.0639 (4)
N10.72016 (12)0.3431 (3)0.15907 (10)0.0597 (4)
N20.62677 (10)0.2123 (3)0.01908 (8)0.0427 (3)
N30.62691 (10)0.1739 (3)0.09359 (8)0.0420 (3)
C10.70076 (13)0.2839 (3)0.09748 (10)0.0477 (4)
H10.72530.38940.05190.057*
C20.68290 (15)0.1905 (4)0.22385 (11)0.0603 (5)
H20.69490.22920.26770.072*
C30.62814 (14)0.0194 (4)0.22982 (11)0.0596 (5)
H30.60350.11910.27660.071*
C40.61008 (12)0.0806 (4)0.16510 (10)0.0493 (4)
H40.57410.22440.16710.059*
C50.64659 (11)0.0761 (3)0.09706 (9)0.0365 (4)
C60.63100 (11)0.0061 (3)0.02519 (10)0.0380 (4)
C70.60960 (11)0.3795 (3)0.12422 (10)0.0403 (4)
H70.59280.53340.09420.048*
C80.61583 (10)0.3768 (3)0.20592 (9)0.0373 (4)
C90.66527 (12)0.1856 (3)0.26163 (10)0.0457 (4)
H90.69340.05160.24640.055*
C100.67294 (12)0.1932 (4)0.33914 (10)0.0510 (4)
H100.70640.06600.37620.061*
C110.63065 (12)0.3906 (4)0.36095 (10)0.0477 (4)
C120.58098 (13)0.5817 (4)0.30759 (12)0.0537 (5)
H120.55220.71300.32320.064*
C130.57459 (13)0.5752 (3)0.23019 (11)0.0485 (4)
H130.54220.70560.19390.058*
C140.59039 (13)0.2668 (4)0.46456 (11)0.0568 (5)
C150.61036 (14)0.3114 (5)0.55032 (11)0.0647 (6)
H15A0.61150.49680.56050.097*
H15B0.66810.23620.58400.097*
H15C0.56430.22990.56190.097*
H2'0.6234 (12)0.369 (2)0.0002 (10)0.048 (5)*
O30.53569 (15)0.1229 (5)0.41928 (11)0.1332 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0910 (10)0.0271 (6)0.0590 (8)0.0011 (6)0.0423 (7)0.0038 (5)
O20.0756 (9)0.0812 (10)0.0411 (7)0.0283 (8)0.0308 (7)0.0160 (7)
N10.0870 (12)0.0523 (9)0.0551 (9)0.0080 (8)0.0450 (9)0.0004 (8)
N20.0680 (9)0.0283 (7)0.0422 (8)0.0018 (6)0.0335 (7)0.0051 (6)
N30.0589 (9)0.0354 (7)0.0401 (7)0.0009 (6)0.0292 (6)0.0034 (6)
C10.0674 (11)0.0391 (9)0.0435 (9)0.0065 (8)0.0304 (9)0.0046 (7)
C20.0835 (14)0.0644 (12)0.0435 (10)0.0063 (11)0.0373 (10)0.0064 (9)
C30.0724 (13)0.0663 (13)0.0356 (9)0.0018 (10)0.0189 (9)0.0102 (9)
C40.0540 (10)0.0445 (9)0.0458 (10)0.0027 (8)0.0180 (8)0.0067 (8)
C50.0452 (8)0.0296 (7)0.0353 (8)0.0060 (6)0.0178 (7)0.0034 (6)
C60.0484 (9)0.0280 (8)0.0399 (8)0.0014 (6)0.0209 (7)0.0037 (6)
C70.0502 (9)0.0336 (8)0.0426 (9)0.0010 (7)0.0252 (7)0.0053 (7)
C80.0429 (8)0.0349 (8)0.0403 (8)0.0055 (6)0.0237 (7)0.0007 (6)
C90.0494 (9)0.0449 (9)0.0471 (10)0.0039 (7)0.0248 (8)0.0017 (8)
C100.0560 (10)0.0550 (11)0.0404 (9)0.0027 (8)0.0190 (8)0.0061 (8)
C110.0543 (10)0.0549 (11)0.0384 (9)0.0167 (8)0.0240 (8)0.0100 (8)
C120.0691 (12)0.0469 (10)0.0570 (11)0.0012 (9)0.0384 (10)0.0091 (9)
C130.0602 (11)0.0388 (9)0.0513 (10)0.0034 (8)0.0285 (8)0.0018 (8)
C140.0563 (11)0.0758 (13)0.0406 (9)0.0116 (10)0.0230 (8)0.0064 (9)
C150.0679 (13)0.0904 (16)0.0411 (10)0.0038 (11)0.0282 (9)0.0026 (10)
O30.1493 (18)0.203 (2)0.0656 (11)0.1225 (18)0.0636 (12)0.0513 (13)
Geometric parameters (Å, º) top
O1—C61.2277 (18)C7—C81.463 (2)
O2—C141.329 (2)C7—H70.9300
O2—C111.410 (2)C8—C131.389 (2)
N1—C21.332 (3)C8—C91.394 (2)
N1—C11.336 (2)C9—C101.378 (2)
N2—C61.348 (2)C9—H90.9300
N2—N31.3844 (19)C10—C111.373 (3)
N2—H2'0.866 (9)C10—H100.9300
N3—C71.276 (2)C11—C121.374 (3)
C1—C51.381 (2)C12—C131.384 (3)
C1—H10.9300C12—H120.9300
C2—C31.367 (3)C13—H130.9300
C2—H20.9300C14—O31.180 (2)
C3—C41.380 (3)C14—C151.486 (3)
C3—H30.9300C15—H15A0.9600
C4—C51.386 (2)C15—H15B0.9600
C4—H40.9300C15—H15C0.9600
C5—C61.493 (2)
C14—O2—C11118.47 (14)C13—C8—C9118.60 (16)
C2—N1—C1116.41 (17)C13—C8—C7119.60 (15)
C6—N2—N3120.70 (13)C9—C8—C7121.75 (15)
C6—N2—H2'118.8 (12)C10—C9—C8120.64 (16)
N3—N2—H2'120.5 (12)C10—C9—H9119.7
C7—N3—N2114.55 (13)C8—C9—H9119.7
N1—C1—C5124.26 (16)C11—C10—C9119.27 (17)
N1—C1—H1117.9C11—C10—H10120.4
C5—C1—H1117.9C9—C10—H10120.4
N1—C2—C3124.06 (18)C10—C11—C12121.74 (16)
N1—C2—H2118.0C10—C11—O2119.60 (17)
C3—C2—H2118.0C12—C11—O2118.53 (17)
C2—C3—C4118.76 (17)C11—C12—C13118.72 (17)
C2—C3—H3120.6C11—C12—H12120.6
C4—C3—H3120.6C13—C12—H12120.6
C3—C4—C5118.82 (18)C12—C13—C8121.02 (17)
C3—C4—H4120.6C12—C13—H13119.5
C5—C4—H4120.6C8—C13—H13119.5
C1—C5—C4117.67 (16)O3—C14—O2120.82 (18)
C1—C5—C6122.69 (14)O3—C14—C15126.92 (19)
C4—C5—C6119.53 (15)O2—C14—C15112.26 (17)
O1—C6—N2123.50 (15)C14—C15—H15A109.5
O1—C6—C5121.50 (14)C14—C15—H15B109.5
N2—C6—C5115.00 (13)H15A—C15—H15B109.5
N3—C7—C8121.05 (14)C14—C15—H15C109.5
N3—C7—H7119.5H15A—C15—H15C109.5
C8—C7—H7119.5H15B—C15—H15C109.5
C6—N2—N3—C7170.37 (15)N3—C7—C8—C13163.02 (16)
C2—N1—C1—C50.9 (3)N3—C7—C8—C919.6 (2)
C1—N1—C2—C30.7 (3)C13—C8—C9—C100.1 (2)
N1—C2—C3—C40.4 (3)C7—C8—C9—C10177.51 (15)
C2—C3—C4—C51.3 (3)C8—C9—C10—C110.5 (3)
N1—C1—C5—C40.0 (3)C9—C10—C11—C120.2 (3)
N1—C1—C5—C6176.14 (16)C9—C10—C11—O2175.82 (15)
C3—C4—C5—C11.1 (2)C14—O2—C11—C1085.1 (2)
C3—C4—C5—C6177.41 (16)C14—O2—C11—C1299.2 (2)
N3—N2—C6—O19.9 (3)C10—C11—C12—C130.7 (3)
N3—N2—C6—C5169.77 (13)O2—C11—C12—C13174.95 (16)
C1—C5—C6—O1144.25 (18)C11—C12—C13—C81.3 (3)
C4—C5—C6—O131.8 (2)C9—C8—C13—C121.0 (3)
C1—C5—C6—N235.5 (2)C7—C8—C13—C12178.50 (16)
C4—C5—C6—N2148.44 (16)C11—O2—C14—O31.5 (3)
N2—N3—C7—C8174.03 (14)C11—O2—C14—C15179.02 (17)
Hydrogen-bond geometry (Å, º) top
Cg1and Cg2 are the centroids of the C8–C13 and C1–C5/N1 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.87 (1)2.08 (1)2.9107 (18)162 (2)
C7—H7···O1i0.932.483.251 (2)140
C15—H15C···O3ii0.962.553.469 (4)161
C4—H4···Cg1iii0.933.133.821 (2)133
C13—H13···Cg2iii0.933.283.860 (3)122
C15—H15A···Cg2iv0.963.393.734 (3)104
C15—H15B···Cg2iv0.963.203.734 (3)117
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+1; (iii) x+1, y, z; (iv) x+3/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg1and Cg2 are the centroids of the C8–C13 and C1–C5/N1 rings, respectively.
D—H···AD—HH···AD···AD—H···A
N2—H2'···O1i0.866 (9)2.076 (11)2.9107 (18)161.5 (17)
C7—H7···O1i0.92932.48203.251 (2)140
C15—H15C···O3ii0.95992.54863.469 (4)161
C4—H4···Cg1iii0.93003.12673.821 (2)133
C13—H13···Cg2iii0.93003.28253.860 (3)122
C15—H15A···Cg2iv0.96003.39113.734 (3)104
C15—H15B···Cg2iv0.96003.19843.734 (3)117
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+1; (iii) x+1, y, z; (iv) x+3/2, y+1/2, z+1/2.
 

Acknowledgements

The authors are grateful to the Sophisticated Analytical Instruments Facility, Cochin University of Science and Technology, Kochi-22, India, for the diffraction measurements. RV and RD thank Christ University, Bangalore, India, for financial support.

References

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