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

Alsubari, A.; Moussaif, A.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810024918

organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page o1905

https://doi.org/10.1107/S1600536810024918

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

Abdulsalam Alsubari,^a Ahmed Moussaif,^a Hafid Zouihri,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bCNRST Division UATRS, Angle Allal Fassi/FAR, BP 8027 Hay Riad, Rabat, Morocco, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 21 June 2010; accepted 25 June 2010; online 3 July 2010)

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 ). For a related structure, see: Ali et al. (2005a ,b ).

Experimental

Crystal data

C₁₈H₁₅N₃O₂
M_r = 305.33
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.108
S = 1.00
3286 reflections
212 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	0.88 (2)	1.98 (2)	2.721 (2)	141 (2)

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810024918/jh2174Isup2.hkl

checkCIF report

Comment top

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) °.

Related literature top

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

Experimental top

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.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

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.

N'-(1-Allyl-2-oxoindolin-3-ylidene)benzohydrazide top

Crystal data top

C₁₈H₁₅N₃O₂	F(000) = 640
M_r = 305.33	D_x = 1.370 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3004 reflections
a = 7.5921 (2) Å	θ = 2.7–25.0°
b = 15.1968 (4) Å	µ = 0.09 mm⁻¹
c = 12.8716 (3) Å	T = 293 K
β = 94.481 (2)°	Prism, yellow
V = 1480.53 (7) Å³	0.35 × 0.30 × 0.20 mm
Z = 4

Data collection top

Bruker X8 APEXII diffractometer	2343 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.059
Graphite monochromator	θ_max = 27.1°, θ_min = 2.7°
φ and ω scans	h = −9→9
17477 measured reflections	k = −19→19
3286 independent reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0463P)² + 0.3757P] where P = (F_o² + 2F_c²)/3
3286 reflections	(Δ/σ)_max = 0.001
212 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₈H₁₅N₃O₂	V = 1480.53 (7) Å³
M_r = 305.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.5921 (2) Å	µ = 0.09 mm⁻¹
b = 15.1968 (4) Å	T = 293 K
c = 12.8716 (3) Å	0.35 × 0.30 × 0.20 mm
β = 94.481 (2)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.18 e Å⁻³
3286 reflections	Δρ_min = −0.21 e Å⁻³
212 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.63773 (15)	0.55475 (7)	0.60381 (8)	0.0315 (3)
O2	0.68617 (16)	0.66838 (8)	0.24350 (8)	0.0353 (3)
N1	0.76855 (17)	0.41763 (9)	0.62121 (10)	0.0271 (3)
N2	0.75597 (16)	0.53877 (8)	0.38503 (9)	0.0248 (3)
N3	0.67263 (17)	0.61477 (9)	0.40734 (10)	0.0259 (3)
H3	0.638 (2)	0.6205 (11)	0.4710 (14)	0.034 (5)*
C1	0.8544 (2)	0.35920 (10)	0.55565 (12)	0.0261 (3)
C2	0.9222 (2)	0.27683 (11)	0.57850 (13)	0.0318 (4)
H2	0.9162	0.2518	0.6441	0.038*
C3	1.0002 (2)	0.23266 (11)	0.49925 (14)	0.0342 (4)
H3A	1.0454	0.1765	0.5120	0.041*
C4	1.0126 (2)	0.27008 (11)	0.40166 (14)	0.0338 (4)
H4	1.0683	0.2395	0.3509	0.041*
C5	0.9423 (2)	0.35293 (11)	0.37944 (12)	0.0292 (4)
H5	0.9496	0.3781	0.3141	0.035*
C6	0.86100 (19)	0.39725 (10)	0.45682 (12)	0.0248 (3)
C7	0.7178 (2)	0.49230 (11)	0.56872 (12)	0.0258 (3)
C8	0.7558 (2)	0.40781 (12)	0.73353 (12)	0.0306 (4)
H8A	0.7490	0.3458	0.7505	0.037*
H8B	0.6484	0.4359	0.7529	0.037*
C9	0.9114 (2)	0.44791 (11)	0.79466 (12)	0.0302 (4)
H9	1.0233	0.4259	0.7850	0.036*
C10	0.8980 (3)	0.51229 (13)	0.86094 (14)	0.0418 (5)
H10A	0.7876	0.5354	0.8720	0.050*
H10B	0.9988	0.5350	0.8971	0.050*
C11	0.77560 (19)	0.48267 (10)	0.46041 (11)	0.0238 (3)
C12	0.6459 (2)	0.67879 (11)	0.33277 (11)	0.0255 (3)
C13	0.5594 (2)	0.76046 (10)	0.36850 (11)	0.0254 (3)
C14	0.5437 (2)	0.78064 (11)	0.47319 (12)	0.0300 (4)
H14	0.5883	0.7420	0.5248	0.036*
C15	0.4623 (2)	0.85771 (12)	0.50059 (13)	0.0351 (4)
H15	0.4523	0.8708	0.5705	0.042*
C16	0.3957 (2)	0.91536 (11)	0.42413 (14)	0.0339 (4)
H16	0.3399	0.9669	0.4427	0.041*
C17	0.4119 (2)	0.89656 (11)	0.32019 (13)	0.0338 (4)
H17	0.3677	0.9356	0.2689	0.041*
C18	0.4937 (2)	0.81987 (11)	0.29260 (13)	0.0313 (4)
H18	0.5051	0.8077	0.2226	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0376 (6)	0.0279 (6)	0.0296 (6)	0.0016 (5)	0.0074 (5)	−0.0031 (5)
O2	0.0445 (7)	0.0378 (7)	0.0243 (6)	0.0041 (6)	0.0065 (5)	0.0008 (5)
N1	0.0309 (7)	0.0272 (7)	0.0234 (6)	−0.0021 (6)	0.0028 (5)	−0.0006 (5)
N2	0.0254 (7)	0.0229 (7)	0.0258 (6)	−0.0022 (5)	0.0005 (5)	−0.0037 (5)
N3	0.0325 (7)	0.0226 (7)	0.0230 (7)	0.0006 (6)	0.0036 (5)	−0.0020 (6)
C1	0.0244 (8)	0.0247 (8)	0.0286 (8)	−0.0056 (7)	−0.0011 (6)	−0.0035 (6)
C2	0.0336 (9)	0.0272 (9)	0.0338 (9)	−0.0038 (7)	−0.0015 (7)	0.0037 (7)
C3	0.0342 (9)	0.0223 (9)	0.0452 (10)	0.0013 (7)	−0.0030 (8)	−0.0014 (7)
C4	0.0323 (9)	0.0284 (9)	0.0402 (10)	0.0022 (7)	0.0003 (7)	−0.0094 (7)
C5	0.0292 (8)	0.0296 (9)	0.0283 (8)	−0.0014 (7)	0.0000 (7)	−0.0052 (7)
C6	0.0239 (7)	0.0231 (8)	0.0267 (8)	−0.0042 (6)	−0.0013 (6)	−0.0028 (6)
C7	0.0260 (8)	0.0260 (9)	0.0254 (8)	−0.0051 (7)	0.0023 (6)	−0.0018 (6)
C8	0.0366 (9)	0.0315 (9)	0.0241 (8)	−0.0049 (7)	0.0048 (7)	0.0037 (7)
C9	0.0319 (9)	0.0327 (10)	0.0259 (8)	0.0010 (7)	0.0017 (7)	0.0056 (7)
C10	0.0400 (10)	0.0462 (12)	0.0386 (10)	−0.0019 (9)	−0.0007 (8)	−0.0081 (9)
C11	0.0237 (7)	0.0225 (8)	0.0249 (8)	−0.0048 (6)	0.0007 (6)	−0.0036 (6)
C12	0.0251 (8)	0.0273 (9)	0.0237 (8)	−0.0033 (7)	0.0001 (6)	−0.0002 (6)
C13	0.0258 (8)	0.0239 (8)	0.0262 (8)	−0.0030 (6)	0.0000 (6)	0.0003 (6)
C14	0.0339 (9)	0.0300 (9)	0.0255 (8)	0.0023 (7)	−0.0005 (7)	0.0028 (7)
C15	0.0401 (10)	0.0343 (10)	0.0309 (9)	0.0022 (8)	0.0034 (7)	−0.0056 (7)
C16	0.0319 (9)	0.0248 (9)	0.0441 (10)	0.0013 (7)	−0.0018 (7)	−0.0034 (7)
C17	0.0361 (9)	0.0258 (9)	0.0380 (9)	−0.0011 (7)	−0.0066 (7)	0.0070 (7)
C18	0.0378 (9)	0.0292 (9)	0.0265 (8)	−0.0036 (7)	−0.0006 (7)	0.0021 (7)

Geometric parameters (Å, º) top

O1—C7	1.2318 (18)	C7—C11	1.501 (2)
O2—C12	1.2223 (18)	C8—C9	1.497 (2)
N1—C7	1.361 (2)	C8—H8A	0.9700
N1—C1	1.418 (2)	C8—H8B	0.9700
N1—C8	1.4641 (19)	C9—C10	1.307 (2)
N2—C11	1.2915 (19)	C9—H9	0.9300
N2—N3	1.3584 (18)	C10—H10A	0.9300
N3—C12	1.371 (2)	C10—H10B	0.9300
N3—H3	0.883 (18)	C12—C13	1.493 (2)
C1—C2	1.377 (2)	C13—C18	1.394 (2)
C1—C6	1.402 (2)	C13—C14	1.396 (2)
C2—C3	1.392 (2)	C14—C15	1.383 (2)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.389 (2)	C15—C16	1.383 (2)
C3—H3A	0.9300	C15—H15	0.9300
C4—C5	1.388 (2)	C16—C17	1.383 (2)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.387 (2)	C17—C18	1.380 (2)
C5—H5	0.9300	C17—H17	0.9300
C6—C11	1.453 (2)	C18—H18	0.9300

C7—N1—C1	110.61 (12)	C9—C8—H8B	109.3
C7—N1—C8	122.50 (13)	H8A—C8—H8B	108.0
C1—N1—C8	126.35 (14)	C10—C9—C8	123.28 (16)
C11—N2—N3	115.52 (13)	C10—C9—H9	118.4
N2—N3—C12	120.10 (13)	C8—C9—H9	118.4
N2—N3—H3	117.1 (11)	C9—C10—H10A	120.0
C12—N3—H3	122.8 (11)	C9—C10—H10B	120.0
C2—C1—C6	121.98 (15)	H10A—C10—H10B	120.0
C2—C1—N1	128.60 (15)	N2—C11—C6	126.25 (14)
C6—C1—N1	109.42 (14)	N2—C11—C7	127.48 (14)
C1—C2—C3	117.11 (15)	C6—C11—C7	106.27 (13)
C1—C2—H2	121.4	O2—C12—N3	122.15 (15)
C3—C2—H2	121.4	O2—C12—C13	123.06 (14)
C4—C3—C2	121.89 (16)	N3—C12—C13	114.77 (13)
C4—C3—H3A	119.1	C18—C13—C14	118.77 (15)
C2—C3—H3A	119.1	C18—C13—C12	117.67 (14)
C5—C4—C3	120.37 (16)	C14—C13—C12	123.55 (14)
C5—C4—H4	119.8	C15—C14—C13	120.38 (15)
C3—C4—H4	119.8	C15—C14—H14	119.8
C6—C5—C4	118.56 (15)	C13—C14—H14	119.8
C6—C5—H5	120.7	C14—C15—C16	120.05 (16)
C4—C5—H5	120.7	C14—C15—H15	120.0
C5—C6—C1	120.06 (15)	C16—C15—H15	120.0
C5—C6—C11	132.96 (15)	C17—C16—C15	120.14 (16)
C1—C6—C11	106.97 (13)	C17—C16—H16	119.9
O1—C7—N1	126.09 (14)	C15—C16—H16	119.9
O1—C7—C11	127.17 (14)	C18—C17—C16	119.95 (16)
N1—C7—C11	106.74 (13)	C18—C17—H17	120.0
N1—C8—C9	111.54 (13)	C16—C17—H17	120.0
N1—C8—H8A	109.3	C17—C18—C13	120.69 (15)
C9—C8—H8A	109.3	C17—C18—H18	119.7
N1—C8—H8B	109.3	C13—C18—H18	119.7

C11—N2—N3—C12	179.73 (14)	N3—N2—C11—C7	−0.3 (2)
C7—N1—C1—C2	−178.87 (15)	C5—C6—C11—N2	0.6 (3)
C8—N1—C1—C2	9.5 (3)	C1—C6—C11—N2	179.33 (14)
C7—N1—C1—C6	0.38 (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—C3	0.7 (2)	O1—C7—C11—N2	1.9 (3)
N1—C1—C2—C3	179.84 (15)	N1—C7—C11—N2	−179.10 (14)
C1—C2—C3—C4	1.1 (2)	O1—C7—C11—C6	−178.79 (15)
C2—C3—C4—C5	−1.7 (3)	N1—C7—C11—C6	0.26 (16)
C3—C4—C5—C6	0.4 (2)	N2—N3—C12—O2	4.0 (2)
C4—C5—C6—C1	1.4 (2)	N2—N3—C12—C13	−177.63 (12)
C4—C5—C6—C11	179.98 (16)	O2—C12—C13—C18	11.9 (2)
C2—C1—C6—C5	−1.9 (2)	N3—C12—C13—C18	−166.38 (14)
N1—C1—C6—C5	178.75 (13)	O2—C12—C13—C14	−167.09 (15)
C2—C1—C6—C11	179.12 (14)	N3—C12—C13—C14	14.6 (2)
N1—C1—C6—C11	−0.19 (16)	C18—C13—C14—C15	0.8 (2)
C1—N1—C7—O1	178.68 (15)	C12—C13—C14—C15	179.84 (15)
C8—N1—C7—O1	−9.3 (2)	C13—C14—C15—C16	0.0 (3)
C1—N1—C7—C11	−0.38 (16)	C14—C15—C16—C17	−0.6 (3)
C8—N1—C7—C11	171.67 (13)	C15—C16—C17—C18	0.4 (3)
C7—N1—C8—C9	−83.08 (19)	C16—C17—C18—C13	0.5 (3)
C1—N1—C8—C9	87.67 (19)	C14—C13—C18—C17	−1.1 (2)
N1—C8—C9—C10	119.36 (18)	C12—C13—C18—C17	179.85 (14)
N3—N2—C11—C6	−179.51 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.88 (2)	1.98 (2)	2.721 (2)	141 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅N₃O₂
M_r	305.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.5921 (2), 15.1968 (4), 12.8716 (3)
β (°)	94.481 (2)
V (Å³)	1480.53 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.30 × 0.20

Data collection
Diffractometer	Bruker X8 APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17477, 3286, 2343
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.642

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.108, 1.00
No. of reflections	3286
No. of parameters	212
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.88 (2)	1.98 (2)	2.721 (2)	141 (2)

Acknowledgements

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

References

Ali, H. M., Abdul Halim, S. N. & Ng, S. W. (2005a). Acta Cryst. E61, o3285–o3286. Web of Science CSD CrossRef IUCr Journals Google Scholar
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