1-Allyl-5-chloro­indoline-2,3-dione

Tribak, Z.; Kandri Rodi, Y.; Haoudi, A.; Essassi, E.M.; Capet, F.; Zouihri, H.

doi:10.1107/S2414314616008622

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 6| June 2016| x160862

doi:10.1107/S2414314616008622

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1-Allyl-5-chloroindoline-2,3-dione

Zineb Tribak,^a Youssef Kandri Rodi,^a Amal Haoudi,^a ^* El Mokhtar Essassi,^b Fréderic Capet ^c and Hafid Zouihri ^d

^aLaboratoire de Chimie Organique Appliquée-Chimie Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fès, Morocco, ^bLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat, Morocco, ^cUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181, Ecole Nationale Supérieure de Chimie de Lille, France, and ^dDépartement de Chimie, Faculté des Sciences, Université Ibn Zohr, BP 8106, Cité Dakhla, 80000 Agadir, Morocco
^*Correspondence e-mail: haoudi_amal@yahoo.fr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 26 May 2016; accepted 28 May 2016; online 17 June 2016)

In the title compound, C₁₁H₈ClNO₂, the allyl side chain is almost perpendicular to the 5-chloroindoline-2,3-dione ring system, with a dihedral angle of 88.0 (3)°. In the crystal, C—H⋯O interactions link the molecules into layers lying parallel to the bc plane.

Keywords: crystal structure; hydrogen bonds; layers; indoline.

CCDC reference: 1482398

Structure description

As part of our ongoing studies of 5-chloroisatin derivatives (Kharbach et al., 2016 ), we now describe the structure of the title compound, C₁₁H₈ClNO₂ (Fig. 1), which was obtained by reaction of 5-chloroisatin with allyl bromide in phase-transfer catalysis conditions.

Figure 1
The molecular structure of the title molecule, showing displacement ellipsoids drawn at the 30% probability level.

The allyl group is almost perpendicular to the 5-chloroindoline-2,3-dione ring system (r.m.s. deviation = 0.034 Å) with a dihedral angle of 88.0 (3)°: the N1—C9—C10—C11 torsion angle is −5.7 (5)°. In the crystal, C—H⋯O interactions (Fig. 2, Table 1) link molecules into layers running parallel to the bc plane (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.96 (2)	2.42 (2)	3.283 (2)	151.0 (19)
C11—H11A⋯O2ⁱⁱ	1.02 (4)	2.39 (3)	3.377 (3)	165 (3)
C11—H11B⋯O2ⁱⁱⁱ	1.04 (3)	2.55 (3)	3.572 (3)	167 (2)
Symmetry codes: (i) x, y+1, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
The crystal structure of the title compound, viewed along the c axis, showing layers parallel to the bc plane linked by C—H⋯O hydrogen bonds (dashed lines). For the sake of clarity, H atoms not involved in the hydrogen bonds have been omitted.

Figure 3
The crystal structure of the title compound, viewed along the b axis, showing chains parallel to the bc plane linked by C—H⋯O hydrogen bonds (dashed lines). For the sake of clarity, H atoms not involved in the hydrogen bonds have been omitted.

Synthesis and crystallization

To a solution of 5-chloro-1H-indole-2,3-dione (0.4 g, 2,20 mmol) in DMF (25 ml) was added K₂CO₃ (0.5 g, 3,30 mmol) as a base, tetra-n-butylammoium bromide (0.1 g, 0,3 mmol) as catalyst and then 3-bromoprop-1-ene (0.34 ml, 2.97 mmol). The reaction mixture was stirred for 48 h at room temperature; once the reaction was complete, the solvent was evaporated in vacuo. The title compound obtained was recrystallized from ethanol solution to afford red crystals (yield: 89%, m.p.: 415 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₁H₈ClNO₂
M_r	221.63
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	296
a, b, c (Å)	31.2222 (6), 7.9107 (2), 8.3373 (2)
V (Å³)	2059.23 (8)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.35
Crystal size (mm)	0.53 × 0.30 × 0.28

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS, Bruker, 2015 )
T_min, T_max	0.705, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	33452, 2554, 1889
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.146, 1.02
No. of reflections	2554
No. of parameters	168
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.20
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1482398

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616008622/hb4053sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616008622/hb4053Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616008622/hb4053Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

1-Allyl-5-chloroindoline-2,3-dione top

Crystal data top

C₁₁H₈ClNO₂	D_x = 1.430 Mg m⁻³
M_r = 221.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 9899 reflections
a = 31.2222 (6) Å	θ = 2.7–26.7°
b = 7.9107 (2) Å	µ = 0.35 mm⁻¹
c = 8.3373 (2) Å	T = 296 K
V = 2059.23 (8) Å³	Block, red
Z = 8	0.53 × 0.30 × 0.28 mm
F(000) = 912

Data collection top

Bruker APEXII CCD diffractometer	1889 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.030
Absorption correction: multi-scan (SADABS, Bruker, 2015)	θ_max = 28.3°, θ_min = 2.6°
T_min = 0.705, T_max = 0.746	h = −41→41
33452 measured reflections	k = −10→10
2554 independent reflections	l = −11→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	All H-atom parameters refined
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0718P)² + 0.7243P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2554 reflections	Δρ_max = 0.28 e Å⁻³
168 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints

Special details top

Experimental. SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0610 before and 0.0436 after correction. The Ratio of minimum to maximum transmission is 0.9447. The λ/2 correction factor is Not present.

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.74155 (2)	0.50698 (9)	0.57033 (8)	0.0830 (3)
O1	0.63056 (6)	0.04791 (17)	0.2249 (2)	0.0740 (5)
N1	0.59967 (5)	0.4519 (2)	0.10974 (19)	0.0534 (4)
O2	0.56737 (5)	0.2127 (2)	0.0112 (2)	0.0819 (5)
C6	0.65189 (5)	0.3371 (2)	0.2739 (2)	0.0442 (4)
C1	0.63365 (6)	0.4861 (2)	0.2156 (2)	0.0442 (4)
C7	0.62735 (6)	0.1975 (2)	0.2048 (2)	0.0527 (5)
C5	0.68569 (6)	0.3403 (2)	0.3809 (2)	0.0503 (4)
C2	0.64914 (7)	0.6414 (2)	0.2625 (2)	0.0536 (5)
C8	0.59347 (6)	0.2826 (3)	0.0950 (2)	0.0573 (5)
C4	0.70061 (6)	0.4964 (3)	0.4293 (2)	0.0545 (5)
C3	0.68305 (7)	0.6445 (3)	0.3703 (3)	0.0568 (5)
C9	0.57319 (8)	0.5799 (4)	0.0313 (3)	0.0660 (6)
C10	0.53684 (8)	0.6399 (4)	0.1317 (3)	0.0751 (7)
C11	0.52504 (9)	0.5846 (4)	0.2675 (3)	0.0843 (8)
H2	0.6377 (7)	0.744 (3)	0.220 (3)	0.066 (6)*
H5	0.6966 (7)	0.247 (3)	0.423 (2)	0.058 (6)*
H3	0.6932 (7)	0.743 (3)	0.409 (3)	0.072 (7)*
H9A	0.5617 (9)	0.529 (3)	−0.069 (3)	0.086 (8)*
H11A	0.5430 (13)	0.501 (4)	0.331 (4)	0.116 (11)*
H10	0.5239 (13)	0.753 (6)	0.133 (5)	0.162 (15)*
H11B	0.5002 (10)	0.641 (4)	0.330 (4)	0.102 (9)*
H9B	0.5925 (9)	0.678 (4)	0.002 (4)	0.095 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0629 (4)	0.1088 (6)	0.0774 (4)	−0.0004 (3)	−0.0143 (3)	−0.0100 (3)
O1	0.0905 (11)	0.0387 (7)	0.0928 (11)	−0.0027 (7)	0.0278 (9)	−0.0023 (7)
N1	0.0521 (8)	0.0554 (9)	0.0527 (8)	0.0046 (7)	0.0032 (7)	−0.0018 (7)
O2	0.0649 (9)	0.0938 (12)	0.0869 (11)	−0.0134 (8)	0.0027 (8)	−0.0329 (10)
C6	0.0468 (9)	0.0383 (8)	0.0474 (9)	0.0017 (6)	0.0135 (7)	0.0007 (7)
C1	0.0446 (8)	0.0434 (8)	0.0447 (8)	0.0027 (7)	0.0098 (7)	0.0011 (7)
C7	0.0584 (10)	0.0418 (9)	0.0578 (10)	−0.0020 (7)	0.0238 (9)	−0.0051 (8)
C5	0.0493 (9)	0.0487 (10)	0.0529 (10)	0.0093 (8)	0.0106 (8)	0.0057 (8)
C2	0.0616 (11)	0.0372 (9)	0.0620 (11)	0.0050 (8)	0.0098 (9)	0.0021 (8)
C8	0.0499 (9)	0.0625 (12)	0.0595 (11)	−0.0044 (9)	0.0136 (9)	−0.0139 (9)
C4	0.0457 (9)	0.0652 (12)	0.0525 (10)	−0.0001 (8)	0.0050 (8)	−0.0041 (9)
C3	0.0572 (11)	0.0482 (10)	0.0651 (12)	−0.0076 (8)	0.0097 (9)	−0.0097 (9)
C9	0.0627 (13)	0.0810 (15)	0.0543 (11)	0.0172 (11)	−0.0011 (10)	0.0087 (11)
C10	0.0705 (14)	0.0852 (17)	0.0695 (14)	0.0262 (12)	−0.0011 (11)	0.0013 (12)
C11	0.0718 (15)	0.111 (2)	0.0702 (16)	0.0296 (15)	0.0040 (13)	−0.0046 (15)

Geometric parameters (Å, º) top

Cl1—C4	1.739 (2)	C5—H5	0.89 (2)
O1—C7	1.200 (2)	C2—C3	1.389 (3)
N1—C1	1.406 (2)	C2—H2	0.95 (2)
N1—C8	1.359 (3)	C4—C3	1.384 (3)
N1—C9	1.461 (3)	C3—H3	0.91 (3)
O2—C8	1.208 (2)	C9—C10	1.487 (3)
C6—C1	1.396 (2)	C9—H9A	1.00 (3)
C6—C7	1.462 (3)	C9—H9B	1.01 (3)
C6—C5	1.382 (3)	C10—C11	1.269 (4)
C1—C2	1.377 (3)	C10—H10	0.98 (5)
C7—C8	1.552 (3)	C11—H11A	1.02 (4)
C5—C4	1.380 (3)	C11—H11B	1.04 (3)

C1—N1—C9	125.07 (18)	O2—C8—C7	127.1 (2)
C8—N1—C1	110.69 (16)	C5—C4—Cl1	119.25 (16)
C8—N1—C9	124.2 (2)	C5—C4—C3	121.34 (19)
C1—C6—C7	106.63 (16)	C3—C4—Cl1	119.40 (16)
C5—C6—C1	121.35 (16)	C2—C3—H3	121.0 (15)
C5—C6—C7	131.98 (16)	C4—C3—C2	121.12 (18)
C6—C1—N1	111.36 (15)	C4—C3—H3	117.8 (15)
C2—C1—N1	127.91 (17)	N1—C9—C10	113.65 (19)
C2—C1—C6	120.73 (17)	N1—C9—H9A	107.4 (16)
O1—C7—C6	130.2 (2)	N1—C9—H9B	107.7 (17)
O1—C7—C8	124.55 (19)	C10—C9—H9A	109.1 (16)
C6—C7—C8	105.22 (15)	C10—C9—H9B	110.3 (17)
C6—C5—H5	122.0 (14)	H9A—C9—H9B	109 (2)
C4—C5—C6	117.58 (17)	C9—C10—H10	128 (3)
C4—C5—H5	120.3 (14)	C11—C10—C9	127.8 (2)
C1—C2—C3	117.86 (18)	C11—C10—H10	101 (3)
C1—C2—H2	121.4 (14)	C10—C11—H11A	122 (2)
C3—C2—H2	120.7 (14)	C10—C11—H11B	121.3 (16)
N1—C8—C7	106.07 (16)	H11A—C11—H11B	116 (3)
O2—C8—N1	126.8 (2)

Cl1—C4—C3—C2	−177.33 (15)	C1—C2—C3—C4	−0.3 (3)
O1—C7—C8—N1	177.91 (18)	C7—C6—C1—N1	−1.66 (18)
O1—C7—C8—O2	−3.3 (3)	C7—C6—C1—C2	178.41 (16)
N1—C1—C2—C3	179.47 (17)	C7—C6—C5—C4	−176.80 (17)
N1—C9—C10—C11	−5.7 (5)	C5—C6—C1—N1	−179.56 (15)
C6—C1—C2—C3	−0.6 (3)	C5—C6—C1—C2	0.5 (3)
C6—C7—C8—N1	−1.16 (18)	C5—C6—C7—O1	0.3 (3)
C6—C7—C8—O2	177.59 (18)	C5—C6—C7—C8	179.26 (17)
C6—C5—C4—Cl1	177.25 (13)	C5—C4—C3—C2	1.3 (3)
C6—C5—C4—C3	−1.4 (3)	C8—N1—C1—C6	0.9 (2)
C1—N1—C8—O2	−178.56 (18)	C8—N1—C1—C2	−179.15 (18)
C1—N1—C8—C7	0.19 (19)	C8—N1—C9—C10	92.4 (3)
C1—N1—C9—C10	−84.7 (3)	C9—N1—C1—C6	178.33 (17)
C1—C6—C7—O1	−177.32 (19)	C9—N1—C1—C2	−1.7 (3)
C1—C6—C7—C8	1.67 (17)	C9—N1—C8—O2	4.0 (3)
C1—C6—C5—C4	0.5 (3)	C9—N1—C8—C7	−177.24 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.96 (2)	2.42 (2)	3.283 (2)	151.0 (19)
C11—H11A···O2ⁱⁱ	1.02 (4)	2.39 (3)	3.377 (3)	165 (3)
C11—H11B···O2ⁱⁱⁱ	1.04 (3)	2.55 (3)	3.572 (3)	167 (2)

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

References

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