1-Benzyl-5-bromo­indoline-2,3-dione

Kharbach, Y.; Kandri Rodi, Y.; Renard, C.; Essassi, E.M.; El Ammari, L.

doi:10.1107/S2414314616005599

organic compounds

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ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160559

doi:10.1107/S2414314616005599

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1-Benzyl-5-bromoindoline-2,3-dione

Yassine Kharbach,^a ^* Youssef Kandri Rodi,^a Catherine Renard,^b El Mokhtar Essassi ^c and Lahcen El Ammari ^d

^aLaboratoire de Chimie Organique Appliquée–Chimie Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fès, Morocco, ^bUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181, Ecole Nationale Supérieure de Chimie de Lille, Université Lille 1, 59650 Villeneuve d'Ascq Cedex, France, ^cLaboratoire de Chimie Organique Hétérocyclique URAC 21, Pôle de compétences Pharmacochimie, Mohammed V University in Rabat, BP 1014 Avenue Ibn Battouta, Rabat , Morocco, and ^dLaboratoire de Chimie du Solide Appliquée, Faculty of Sciences, Mohammed V University in Rabat, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: kharbachy26@gmail.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 31 March 2016; accepted 4 April 2016; online 8 April 2016)

In the title compound, C₁₅H₁₀BrNO₂, the indoline ring system, the two ketone O atoms and the Br atom lie in a common plane, with the largest deviation from the mean plane being 0.073 (1) Å for the Br atom. The fused-ring system is nearly perpendicular to the benzyl ring, as indicated by the dihedral angle between them of 74.58 (10)°. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds and by π–π interactions [inter-centroid distance = 3.625 (2) Å], forming a two-dimensional structure.

Keywords: crystal structure; indoline ring; hydrogen bonds; π–π interaction.

CCDC reference: 1472134

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Chemical scheme

Structure description

Isatins and analogous compounds have been the focus of much research due to their anticancer, anti-oxygenic, anticonvulsant, antibacterial and sedative activities (Sridhar et al., 2001a ,b ; Sarangapani et al., 1994 ; Verma et al., 2004 ; Pandeya et al., 1999 ; Aboul-Fadl et al., 2010 ). As a continuation of Qachchachi's research work devoted to the development of isatin (Qachchachi et al., 2013 , 2014a ,b ), we report in this paper the synthesis and crystal structure of 1-benzyl-5-bromoindoline-2,3-dione.

The title compound (Fig. 1) is built up from two fused five- and six-membered rings linked to two ketone atoms, a bromine atom and a benzyl group, as shown in Fig.1. The fused-ring system and the attached atoms lie in a common plane with a maximum deviation of 0.073 (1) Å for Br1. Moreover, the benzyl ring are nearly perpendicular to the indoline ring system, making a dihedral angle of 74.58 (10)°. The C10—C9—N1—C8 torsion angle is −77.3 (2) °.

Figure 1
The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds (Table 1) into chains running along the b axis. The chains are further connected by π–π interactions [inter-centroid distance = 3.625 (2) Å], forming layers in the ab plane (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1ⁱ	0.95	2.46	3.056 (2)	121
Symmetry code: (i) $[-x-1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
Molecules linked by C—H⋯O hydrogen bonds and π–π interactions, forming a two-dimensional network.

Synthesis and crystallization

To a solution of 5-bromoisatin (0.4 g, 1.76 mmol) dissolved in DMF (25 ml) was added potassium carbonate (0.6 g, 4.4 mmol), benzyl chloride (0.22 ml, 1.76 mmol) and a catalytic amount of tetra-n-butylammonium bromide (0.1 g, 0.4 mmol). The mixture was stirred for 48 h. After filtering, the reaction was monitored by thin layer chromatography. The title compound was obtained in 72% yield, m.p. = 427 K. The red crystals obtained were analysed by X-ray diffraction.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrNO₂
M_r	316.15
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	4.5205 (1), 13.4538 (3), 21.0436 (5)
V (Å³)	1279.83 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	3.21
Crystal size (mm)	0.36 × 0.32 × 0.21

Data collection
Diffractometer	Bruker X8 APEX
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.649, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	40933, 4484, 4045
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.755

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.058, 1.06
No. of reflections	4484
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.31
Absolute structure	Flack x determined using 1538 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.111 (2)
Computer programs: APEX2 and SAINT-Plus (Bruker, 2009), SHELXS2014 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 2012 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1472134

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616005599/bt4004sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616005599/bt4004Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616005599/bt4004Isup3.cml

checkCIF report

Comment top

Isatin derivatives have formed the nucleus of many-faceted research activities owing to the multitude of potential applications in clinical and medicinal aspects. They opened up a vista of promising prospects in synthetic organic chemistry owing to their biological and pharmacological properties. Isatins and many analogous compounds have formed a prospective avenue of research surrounding their anticancer, antioxygenic, anticonvulsant, antibacterial properties, and sedative activities (Sridhar et al., 2001a; 2001b Sarangapani et al., 1994; Varma et al., 2004; Pandeya et al., 1999; Aboul-Fadl et al., 2010). As a continuation of Qachchachi research work devoted to development of isatin (Qachchachi et al., 2013, 2014a, 2014b), we report in this paper the synthesis of 1-benzyl-5-bromoindoline-2,3-dione (Sheme 1).

The title compound is built up from two fused five and six-membered rings linked to two ketone atoms, brome atom and to a benzyl group as shown in Fig.1. The fused ring system and the attached atoms lie in a common plane with the maximum deviation of 0.073 (1) Å for Br1. Moreover, the mean planes through the phenyl ring is more or less perpendicular to the indoline ring system as indicated by the torsion angle of C10—C9—N1—C8 = -77.3 (2) °.

In the crystal, molecules are linked by weak C—H···O hydrogen bonds to chains running along the b axis. The chains are further connected by π—π interactions [inter-centroid distance = 3.625 (2)Å], forming a two-dimensional layers in the ab plane (Fig. 2).

Experimental top

Structure description top

Isatins and analogous compounds have been the focus of much research due to their anticancer, anti-oxygenic, anticonvulsant, antibacterial and sedative activities (Sridhar et al., 2001a,b; Sarangapani et al., 1994; Verma et al., 2004; Pandeya et al., 1999; Aboul-Fadl et al., 2010). As a continuation of Qachchachi's research work devoted to the development of isatin (Qachchachi et al., 2013, 2014a,b), we report in this paper the synthesis of 1-benzyl-5-bromoindoline-2,3-dione.

The title compound is built up from two fused five- and six-membered rings linked to two ketone atoms, a bromine atom and a benzyl group, as shown in Fig.1. The fused-ring system and the attached atoms lie in a common plane with a maximum deviation of 0.073 (1) Å for Br1. Moreover, the mean planes through the phenyl ring are nearly perpendicular to the indoline ring system, making a dihedral angle of 74.58 (10)°. The C10—C9—N1—C8 torsion angle is -77.3 (2) °.

In the crystal, molecules are linked by weak C—H···O hydrogen bonds (Table 1) into chains running along the b axis. The chains are further connected by π–π interactions [inter-centroid distance = 3.625 (2) Å], forming layers in the ab plane (Fig. 2).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. Molecules linked by C—H···O hydrogen bonds and π–π interactions, forming a two-dimensional network.

1-Benzyl-5-bromoindoline-2,3-dione top

Crystal data top

C₁₅H₁₀BrNO₂	D_x = 1.641 Mg m⁻³
M_r = 316.15	Melting point: 427 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 4.5205 (1) Å	Cell parameters from 4483 reflections
b = 13.4538 (3) Å	θ = 1.8–32.4°
c = 21.0436 (5) Å	µ = 3.21 mm⁻¹
V = 1279.83 (5) Å³	T = 100 K
Z = 4	Block, red
F(000) = 632	0.36 × 0.32 × 0.21 mm

Data collection top

Bruker X8 APEX diffractometer	4484 independent reflections
Radiation source: fine-focus sealed tube	4045 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 32.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
T_min = 0.649, T_max = 0.746	k = −19→19
40933 measured reflections	l = −31→31

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.026	w = 1/[σ²(F_o²) + (0.0292P)² + 0.1626P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.058	(Δ/σ)_max = 0.002
S = 1.06	Δρ_max = 0.54 e Å⁻³
4484 reflections	Δρ_min = −0.31 e Å⁻³
172 parameters	Absolute structure: Flack x determined using 1538 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.111 (2)

Crystal data top

C₁₅H₁₀BrNO₂	V = 1279.83 (5) Å³
M_r = 316.15	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.5205 (1) Å	µ = 3.21 mm⁻¹
b = 13.4538 (3) Å	T = 100 K
c = 21.0436 (5) Å	0.36 × 0.32 × 0.21 mm

Data collection top

Bruker X8 APEX diffractometer	4484 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4045 reflections with I > 2σ(I)
T_min = 0.649, T_max = 0.746	R_int = 0.038
40933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.058	Δρ_max = 0.54 e Å⁻³
S = 1.06	Δρ_min = −0.31 e Å⁻³
4484 reflections	Absolute structure: Flack x determined using 1538 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
172 parameters	Absolute structure parameter: 0.111 (2)
0 restraints

Special details top

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
C1	−0.4855 (5)	0.52077 (16)	0.26022 (11)	0.0228 (5)
C2	−0.2947 (6)	0.53887 (15)	0.32114 (11)	0.0240 (5)
C3	−0.1280 (5)	0.44646 (15)	0.33040 (10)	0.0188 (4)
C4	0.0679 (6)	0.41672 (15)	0.37752 (10)	0.0215 (4)
H4	0.1217	0.4599	0.4113	0.026*
C5	0.1815 (5)	0.32134 (16)	0.37318 (9)	0.0188 (4)
C6	0.1060 (5)	0.25767 (15)	0.32387 (10)	0.0193 (4)
H6	0.1891	0.1928	0.3224	0.023*
C7	−0.0907 (5)	0.28774 (14)	0.27636 (9)	0.0179 (4)
H7	−0.1428	0.2447	0.2424	0.022*
C8	−0.2063 (5)	0.38247 (14)	0.28070 (10)	0.0167 (4)
C9	−0.5340 (5)	0.38185 (15)	0.18194 (10)	0.0203 (4)
H9A	−0.7186	0.4165	0.1698	0.024*
H9B	−0.5837	0.3115	0.1906	0.024*
C10	−0.3180 (5)	0.38661 (16)	0.12731 (10)	0.0191 (4)
C11	−0.1799 (5)	0.30103 (15)	0.10502 (10)	0.0204 (4)
H11	−0.2225	0.2387	0.1241	0.024*
C12	0.0198 (5)	0.30618 (17)	0.05502 (10)	0.0243 (4)
H12	0.1159	0.2477	0.0405	0.029*
C13	0.0785 (6)	0.39639 (19)	0.02647 (11)	0.0301 (5)
H13	0.2132	0.3997	−0.0081	0.036*
C14	−0.0587 (7)	0.48221 (18)	0.04813 (11)	0.0314 (5)
H14	−0.0176	0.5442	0.0284	0.038*
C15	−0.2550 (6)	0.47753 (18)	0.09839 (11)	0.0255 (5)
H15	−0.3475	0.5365	0.1133	0.031*
Br1	0.44066 (5)	0.27424 (2)	0.43746 (2)	0.02327 (6)
N1	−0.4148 (4)	0.42721 (12)	0.23980 (8)	0.0189 (3)
O1	−0.6580 (5)	0.57789 (13)	0.23682 (9)	0.0341 (4)
O2	−0.2970 (5)	0.61533 (13)	0.35125 (9)	0.0359 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0233 (11)	0.0170 (9)	0.0281 (11)	0.0025 (8)	0.0062 (9)	0.0024 (8)
C2	0.0264 (11)	0.0164 (10)	0.0291 (11)	−0.0002 (9)	0.0055 (10)	−0.0018 (8)
C3	0.0215 (11)	0.0137 (8)	0.0211 (9)	−0.0023 (7)	0.0044 (8)	−0.0027 (7)
C4	0.0232 (10)	0.0203 (9)	0.0211 (9)	−0.0044 (9)	0.0029 (10)	−0.0037 (7)
C5	0.0165 (9)	0.0227 (10)	0.0172 (9)	−0.0007 (9)	0.0012 (8)	0.0017 (7)
C6	0.0195 (10)	0.0161 (9)	0.0223 (9)	0.0030 (7)	0.0026 (8)	−0.0003 (7)
C7	0.0198 (10)	0.0143 (8)	0.0197 (8)	−0.0010 (8)	0.0009 (8)	−0.0017 (6)
C8	0.0159 (9)	0.0150 (9)	0.0193 (9)	−0.0011 (8)	0.0037 (8)	0.0005 (7)
C9	0.0167 (9)	0.0206 (9)	0.0235 (9)	−0.0015 (8)	−0.0009 (9)	0.0012 (7)
C10	0.0159 (9)	0.0221 (10)	0.0193 (9)	−0.0017 (8)	−0.0032 (8)	0.0023 (8)
C11	0.0191 (9)	0.0207 (10)	0.0214 (9)	−0.0018 (8)	−0.0034 (9)	0.0007 (7)
C12	0.0225 (10)	0.0291 (10)	0.0214 (10)	−0.0021 (8)	−0.0004 (9)	−0.0028 (8)
C13	0.0294 (12)	0.0394 (13)	0.0216 (10)	−0.0062 (12)	0.0026 (11)	0.0036 (9)
C14	0.0376 (12)	0.0279 (11)	0.0287 (11)	−0.0056 (12)	0.0018 (11)	0.0101 (9)
C15	0.0272 (12)	0.0223 (10)	0.0269 (11)	−0.0017 (9)	−0.0018 (9)	0.0041 (9)
Br1	0.02127 (10)	0.03034 (11)	0.01820 (9)	−0.00156 (9)	−0.00057 (9)	0.00275 (8)
N1	0.0196 (9)	0.0146 (7)	0.0224 (8)	0.0003 (7)	0.0014 (8)	0.0011 (6)
O1	0.0394 (10)	0.0225 (8)	0.0403 (10)	0.0128 (8)	0.0027 (9)	0.0045 (7)
O2	0.0460 (12)	0.0182 (8)	0.0434 (11)	0.0034 (8)	0.0027 (10)	−0.0095 (7)

Geometric parameters (Å, º) top

C1—O1	1.201 (3)	C9—N1	1.465 (3)
C1—N1	1.368 (3)	C9—C10	1.510 (3)
C1—C2	1.564 (3)	C9—H9A	0.9900
C2—O2	1.208 (3)	C9—H9B	0.9900
C2—C3	1.467 (3)	C10—C11	1.391 (3)
C3—C4	1.388 (3)	C10—C15	1.396 (3)
C3—C8	1.400 (3)	C11—C12	1.388 (3)
C4—C5	1.385 (3)	C11—H11	0.9500
C4—H4	0.9500	C12—C13	1.380 (3)
C5—C6	1.388 (3)	C12—H12	0.9500
C5—Br1	1.898 (2)	C13—C14	1.388 (4)
C6—C7	1.398 (3)	C13—H13	0.9500
C6—H6	0.9500	C14—C15	1.382 (3)
C7—C8	1.381 (3)	C14—H14	0.9500
C7—H7	0.9500	C15—H15	0.9500
C8—N1	1.411 (3)

O1—C1—N1	127.7 (2)	C10—C9—H9A	109.2
O1—C1—C2	126.5 (2)	N1—C9—H9B	109.2
N1—C1—C2	105.78 (18)	C10—C9—H9B	109.2
O2—C2—C3	131.0 (2)	H9A—C9—H9B	107.9
O2—C2—C1	123.9 (2)	C11—C10—C15	119.1 (2)
C3—C2—C1	105.08 (18)	C11—C10—C9	120.78 (19)
C4—C3—C8	121.17 (19)	C15—C10—C9	120.1 (2)
C4—C3—C2	131.8 (2)	C12—C11—C10	120.4 (2)
C8—C3—C2	107.0 (2)	C12—C11—H11	119.8
C5—C4—C3	117.15 (19)	C10—C11—H11	119.8
C5—C4—H4	121.4	C13—C12—C11	119.9 (2)
C3—C4—H4	121.4	C13—C12—H12	120.0
C4—C5—C6	122.0 (2)	C11—C12—H12	120.0
C4—C5—Br1	119.41 (16)	C12—C13—C14	120.2 (2)
C6—C5—Br1	118.58 (16)	C12—C13—H13	119.9
C5—C6—C7	120.82 (19)	C14—C13—H13	119.9
C5—C6—H6	119.6	C15—C14—C13	120.0 (2)
C7—C6—H6	119.6	C15—C14—H14	120.0
C8—C7—C6	117.44 (19)	C13—C14—H14	120.0
C8—C7—H7	121.3	C14—C15—C10	120.3 (2)
C6—C7—H7	121.3	C14—C15—H15	119.8
C7—C8—C3	121.4 (2)	C10—C15—H15	119.8
C7—C8—N1	127.32 (19)	C1—N1—C8	110.91 (18)
C3—C8—N1	111.23 (18)	C1—N1—C9	123.96 (19)
N1—C9—C10	112.18 (18)	C8—N1—C9	125.09 (17)
N1—C9—H9A	109.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱ	0.95	2.46	3.056 (2)	121

Symmetry code: (i) −x−1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱ	0.95	2.46	3.056 (2)	120.9

Symmetry code: (i) −x−1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrNO₂
M_r	316.15
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	4.5205 (1), 13.4538 (3), 21.0436 (5)
V (Å³)	1279.83 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.21
Crystal size (mm)	0.36 × 0.32 × 0.21

Data collection
Diffractometer	Bruker X8 APEX
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.649, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	40933, 4484, 4045
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.755

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.058, 1.06
No. of reflections	4484
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.31
Absolute structure	Flack x determined using 1538 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Absolute structure parameter	0.111 (2)

Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS2014 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

References

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ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160559

doi:10.1107/S2414314616005599

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

1-Benzyl-5-bromo­indoline-2,3-dione

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

1-Benzyl-5-bromoindoline-2,3-dione