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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o1905.
Published online 2010 July 3. doi:  10.1107/S1600536810024918
PMCID: PMC3007202

N′-(1-Allyl-2-oxoindolin-3-yl­idene)benzohydrazide

Abstract

In the title compound, C18H15N3O2, the dihedral angle between the ring systems is 15.1 (1)°. The amino H atom is hydrogen bonded to the exocyclic O atom of the five-membered ring, forming an S(6) motif.

Related literature

For the use of the title compound as the starting reactant for the synthesis of other heterocyclic systems, see: Alsubari et al. (2009 [triangle]). For a related structure, see: Ali et al. (2005a [triangle],b [triangle]).

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Object name is e-66-o1905-scheme1.jpg

Experimental

Crystal data

  • C18H15N3O2
  • M r = 305.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1905-efi1.jpg
  • a = 7.5921 (2) Å
  • b = 15.1968 (4) Å
  • c = 12.8716 (3) Å
  • β = 94.481 (2)°
  • V = 1480.53 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.35 × 0.30 × 0.20 mm

Data collection

  • Bruker X8 APEXII diffractometer
  • 17477 measured reflections
  • 3286 independent reflections
  • 2343 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.108
  • S = 1.00
  • 3286 reflections
  • 212 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024918/jh2174sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024918/jh2174Isup2.hkl

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

Acknowledgments

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

An earlier study reports the synthesis of oxindole derivatives bearing an oxazolidin-2-one sub-unit. The title Sciff base (Scheme I) is the starting reactant for the synthesis of other heterocyclic systems (Alsubari et al., 2009). We have previously determined the crystal structure of two modifications of the Schiff base derived by condensing isatin and benzoylhydrazine. In both, the amino unit of the five-membered ring functions as a hydrogen bond donor to carbonyl group of an adjacent molecule to generate a chain structure. Meanwhile, the amino –NH– unit forms an intramolecular hydrogen bond to the –C(═O)– unit of the five-membered ring (Ali et al., 2005a, 2005b). The molecule of C18H15N3O2 (Fig, 1) has a phenyl ring connected to a nine-membered fused-ring through the three-atom –C(═O)–N(H)–N═unit, whose amino H-atom is hydrogen bonded to the carbonyl group of the fused-ring. The two ring systems are aligned at 15.1 (1) °.

Experimental

1-Allylindoline-2,3-dione (0.5 g, 2.7 mmol) and benzoyl hydrazine (0.36 g, 2.7 mmol) were heated in ethanol (20 ml) for 2 h. The solvent was evaporated and the yellow solid was recrystallized from ethanol in 90% yield.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2Ueq(C).

The amino H-atom was located in a difference Fourier map; the N–H distance was restrained to 0.86±0.01 Å; the temperature factor of this hydrogen atom was freely refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the molecule of C18H15N3O2 at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radii.

Crystal data

C18H15N3O2F(000) = 640
Mr = 305.33Dx = 1.370 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3004 reflections
a = 7.5921 (2) Åθ = 2.7–25.0°
b = 15.1968 (4) ŵ = 0.09 mm1
c = 12.8716 (3) ÅT = 293 K
β = 94.481 (2)°Prism, yellow
V = 1480.53 (7) Å30.35 × 0.30 × 0.20 mm
Z = 4

Data collection

Bruker X8 APEXII diffractometer2343 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.059
graphiteθmax = 27.1°, θmin = 2.7°
[var phi] and ω scansh = −9→9
17477 measured reflectionsk = −19→19
3286 independent reflectionsl = −16→16

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.00w = 1/[σ2(Fo2) + (0.0463P)2 + 0.3757P] where P = (Fo2 + 2Fc2)/3
3286 reflections(Δ/σ)max = 0.001
212 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.21 e Å3

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

xyzUiso*/Ueq
O10.63773 (15)0.55475 (7)0.60381 (8)0.0315 (3)
O20.68617 (16)0.66838 (8)0.24350 (8)0.0353 (3)
N10.76855 (17)0.41763 (9)0.62121 (10)0.0271 (3)
N20.75597 (16)0.53877 (8)0.38503 (9)0.0248 (3)
N30.67263 (17)0.61477 (9)0.40734 (10)0.0259 (3)
H30.638 (2)0.6205 (11)0.4710 (14)0.034 (5)*
C10.8544 (2)0.35920 (10)0.55565 (12)0.0261 (3)
C20.9222 (2)0.27683 (11)0.57850 (13)0.0318 (4)
H20.91620.25180.64410.038*
C31.0002 (2)0.23266 (11)0.49925 (14)0.0342 (4)
H3A1.04540.17650.51200.041*
C41.0126 (2)0.27008 (11)0.40166 (14)0.0338 (4)
H41.06830.23950.35090.041*
C50.9423 (2)0.35293 (11)0.37944 (12)0.0292 (4)
H50.94960.37810.31410.035*
C60.86100 (19)0.39725 (10)0.45682 (12)0.0248 (3)
C70.7178 (2)0.49230 (11)0.56872 (12)0.0258 (3)
C80.7558 (2)0.40781 (12)0.73353 (12)0.0306 (4)
H8A0.74900.34580.75050.037*
H8B0.64840.43590.75290.037*
C90.9114 (2)0.44791 (11)0.79466 (12)0.0302 (4)
H91.02330.42590.78500.036*
C100.8980 (3)0.51229 (13)0.86094 (14)0.0418 (5)
H10A0.78760.53540.87200.050*
H10B0.99880.53500.89710.050*
C110.77560 (19)0.48267 (10)0.46041 (11)0.0238 (3)
C120.6459 (2)0.67879 (11)0.33277 (11)0.0255 (3)
C130.5594 (2)0.76046 (10)0.36850 (11)0.0254 (3)
C140.5437 (2)0.78064 (11)0.47319 (12)0.0300 (4)
H140.58830.74200.52480.036*
C150.4623 (2)0.85771 (12)0.50059 (13)0.0351 (4)
H150.45230.87080.57050.042*
C160.3957 (2)0.91536 (11)0.42413 (14)0.0339 (4)
H160.33990.96690.44270.041*
C170.4119 (2)0.89656 (11)0.32019 (13)0.0338 (4)
H170.36770.93560.26890.041*
C180.4937 (2)0.81987 (11)0.29260 (13)0.0313 (4)
H180.50510.80770.22260.038*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0376 (6)0.0279 (6)0.0296 (6)0.0016 (5)0.0074 (5)−0.0031 (5)
O20.0445 (7)0.0378 (7)0.0243 (6)0.0041 (6)0.0065 (5)0.0008 (5)
N10.0309 (7)0.0272 (7)0.0234 (6)−0.0021 (6)0.0028 (5)−0.0006 (5)
N20.0254 (7)0.0229 (7)0.0258 (6)−0.0022 (5)0.0005 (5)−0.0037 (5)
N30.0325 (7)0.0226 (7)0.0230 (7)0.0006 (6)0.0036 (5)−0.0020 (6)
C10.0244 (8)0.0247 (8)0.0286 (8)−0.0056 (7)−0.0011 (6)−0.0035 (6)
C20.0336 (9)0.0272 (9)0.0338 (9)−0.0038 (7)−0.0015 (7)0.0037 (7)
C30.0342 (9)0.0223 (9)0.0452 (10)0.0013 (7)−0.0030 (8)−0.0014 (7)
C40.0323 (9)0.0284 (9)0.0402 (10)0.0022 (7)0.0003 (7)−0.0094 (7)
C50.0292 (8)0.0296 (9)0.0283 (8)−0.0014 (7)0.0000 (7)−0.0052 (7)
C60.0239 (7)0.0231 (8)0.0267 (8)−0.0042 (6)−0.0013 (6)−0.0028 (6)
C70.0260 (8)0.0260 (9)0.0254 (8)−0.0051 (7)0.0023 (6)−0.0018 (6)
C80.0366 (9)0.0315 (9)0.0241 (8)−0.0049 (7)0.0048 (7)0.0037 (7)
C90.0319 (9)0.0327 (10)0.0259 (8)0.0010 (7)0.0017 (7)0.0056 (7)
C100.0400 (10)0.0462 (12)0.0386 (10)−0.0019 (9)−0.0007 (8)−0.0081 (9)
C110.0237 (7)0.0225 (8)0.0249 (8)−0.0048 (6)0.0007 (6)−0.0036 (6)
C120.0251 (8)0.0273 (9)0.0237 (8)−0.0033 (7)0.0001 (6)−0.0002 (6)
C130.0258 (8)0.0239 (8)0.0262 (8)−0.0030 (6)0.0000 (6)0.0003 (6)
C140.0339 (9)0.0300 (9)0.0255 (8)0.0023 (7)−0.0005 (7)0.0028 (7)
C150.0401 (10)0.0343 (10)0.0309 (9)0.0022 (8)0.0034 (7)−0.0056 (7)
C160.0319 (9)0.0248 (9)0.0441 (10)0.0013 (7)−0.0018 (7)−0.0034 (7)
C170.0361 (9)0.0258 (9)0.0380 (9)−0.0011 (7)−0.0066 (7)0.0070 (7)
C180.0378 (9)0.0292 (9)0.0265 (8)−0.0036 (7)−0.0006 (7)0.0021 (7)

Geometric parameters (Å, °)

O1—C71.2318 (18)C7—C111.501 (2)
O2—C121.2223 (18)C8—C91.497 (2)
N1—C71.361 (2)C8—H8A0.9700
N1—C11.418 (2)C8—H8B0.9700
N1—C81.4641 (19)C9—C101.307 (2)
N2—C111.2915 (19)C9—H90.9300
N2—N31.3584 (18)C10—H10A0.9300
N3—C121.371 (2)C10—H10B0.9300
N3—H30.883 (18)C12—C131.493 (2)
C1—C21.377 (2)C13—C181.394 (2)
C1—C61.402 (2)C13—C141.396 (2)
C2—C31.392 (2)C14—C151.383 (2)
C2—H20.9300C14—H140.9300
C3—C41.389 (2)C15—C161.383 (2)
C3—H3A0.9300C15—H150.9300
C4—C51.388 (2)C16—C171.383 (2)
C4—H40.9300C16—H160.9300
C5—C61.387 (2)C17—C181.380 (2)
C5—H50.9300C17—H170.9300
C6—C111.453 (2)C18—H180.9300
C7—N1—C1110.61 (12)C9—C8—H8B109.3
C7—N1—C8122.50 (13)H8A—C8—H8B108.0
C1—N1—C8126.35 (14)C10—C9—C8123.28 (16)
C11—N2—N3115.52 (13)C10—C9—H9118.4
N2—N3—C12120.10 (13)C8—C9—H9118.4
N2—N3—H3117.1 (11)C9—C10—H10A120.0
C12—N3—H3122.8 (11)C9—C10—H10B120.0
C2—C1—C6121.98 (15)H10A—C10—H10B120.0
C2—C1—N1128.60 (15)N2—C11—C6126.25 (14)
C6—C1—N1109.42 (14)N2—C11—C7127.48 (14)
C1—C2—C3117.11 (15)C6—C11—C7106.27 (13)
C1—C2—H2121.4O2—C12—N3122.15 (15)
C3—C2—H2121.4O2—C12—C13123.06 (14)
C4—C3—C2121.89 (16)N3—C12—C13114.77 (13)
C4—C3—H3A119.1C18—C13—C14118.77 (15)
C2—C3—H3A119.1C18—C13—C12117.67 (14)
C5—C4—C3120.37 (16)C14—C13—C12123.55 (14)
C5—C4—H4119.8C15—C14—C13120.38 (15)
C3—C4—H4119.8C15—C14—H14119.8
C6—C5—C4118.56 (15)C13—C14—H14119.8
C6—C5—H5120.7C14—C15—C16120.05 (16)
C4—C5—H5120.7C14—C15—H15120.0
C5—C6—C1120.06 (15)C16—C15—H15120.0
C5—C6—C11132.96 (15)C17—C16—C15120.14 (16)
C1—C6—C11106.97 (13)C17—C16—H16119.9
O1—C7—N1126.09 (14)C15—C16—H16119.9
O1—C7—C11127.17 (14)C18—C17—C16119.95 (16)
N1—C7—C11106.74 (13)C18—C17—H17120.0
N1—C8—C9111.54 (13)C16—C17—H17120.0
N1—C8—H8A109.3C17—C18—C13120.69 (15)
C9—C8—H8A109.3C17—C18—H18119.7
N1—C8—H8B109.3C13—C18—H18119.7
C11—N2—N3—C12179.73 (14)N3—N2—C11—C7−0.3 (2)
C7—N1—C1—C2−178.87 (15)C5—C6—C11—N20.6 (3)
C8—N1—C1—C29.5 (3)C1—C6—C11—N2179.33 (14)
C7—N1—C1—C60.38 (17)C5—C6—C11—C7−178.78 (16)
C8—N1—C1—C6−171.30 (14)C1—C6—C11—C7−0.03 (16)
C6—C1—C2—C30.7 (2)O1—C7—C11—N21.9 (3)
N1—C1—C2—C3179.84 (15)N1—C7—C11—N2−179.10 (14)
C1—C2—C3—C41.1 (2)O1—C7—C11—C6−178.79 (15)
C2—C3—C4—C5−1.7 (3)N1—C7—C11—C60.26 (16)
C3—C4—C5—C60.4 (2)N2—N3—C12—O24.0 (2)
C4—C5—C6—C11.4 (2)N2—N3—C12—C13−177.63 (12)
C4—C5—C6—C11179.98 (16)O2—C12—C13—C1811.9 (2)
C2—C1—C6—C5−1.9 (2)N3—C12—C13—C18−166.38 (14)
N1—C1—C6—C5178.75 (13)O2—C12—C13—C14−167.09 (15)
C2—C1—C6—C11179.12 (14)N3—C12—C13—C1414.6 (2)
N1—C1—C6—C11−0.19 (16)C18—C13—C14—C150.8 (2)
C1—N1—C7—O1178.68 (15)C12—C13—C14—C15179.84 (15)
C8—N1—C7—O1−9.3 (2)C13—C14—C15—C160.0 (3)
C1—N1—C7—C11−0.38 (16)C14—C15—C16—C17−0.6 (3)
C8—N1—C7—C11171.67 (13)C15—C16—C17—C180.4 (3)
C7—N1—C8—C9−83.08 (19)C16—C17—C18—C130.5 (3)
C1—N1—C8—C987.67 (19)C14—C13—C18—C17−1.1 (2)
N1—C8—C9—C10119.36 (18)C12—C13—C18—C17179.85 (14)
N3—N2—C11—C6−179.51 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3···O10.88 (2)1.98 (2)2.721 (2)141 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2174).

References

  • Ali, H. M., Abdul Halim, S. N. & Ng, S. W. (2005a). Acta Cryst. E61, o3285–o3286.
  • Ali, H. M., Abdul Halim, S. N. & Ng, S. W. (2005b). Acta Cryst. E61, o3287–o3288.
  • Alsubari, A., Bouhfid, R. & Essassi, E. M. (2009). ARKIVOC, xii, 337–346.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA..
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920-925.

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