organic compounds
1-Benzyl-5-bromoindoline-2,3-dione
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
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
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 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) °.
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).
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 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 .
details are summarized in Table 2Structural data
CCDC reference: 1472134
10.1107/S2414314616005599/bt4004sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616005599/bt4004Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616005599/bt4004Isup3.cml
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
The title compound was obtained in 72% yield, m.p. = 427 K. The red crystals obtained were analysed by X-ray diffraction.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).
Data collection: APEX2 (Bruker, 2009); cell
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).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. |
C15H10BrNO2 | Dx = 1.641 Mg m−3 |
Mr = 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 |
Bruker X8 APEX diffractometer | 4484 independent reflections |
Radiation source: fine-focus sealed tube | 4045 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 32.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −6→6 |
Tmin = 0.649, Tmax = 0.746 | k = −19→19 |
40933 measured reflections | l = −31→31 |
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(Fo2) + (0.0292P)2 + 0.1626P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.058 | (Δ/σ)max = 0.002 |
S = 1.06 | Δρmax = 0.54 e Å−3 |
4484 reflections | Δρmin = −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) |
C15H10BrNO2 | V = 1279.83 (5) Å3 |
Mr = 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 |
Bruker X8 APEX diffractometer | 4484 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4045 reflections with I > 2σ(I) |
Tmin = 0.649, Tmax = 0.746 | Rint = 0.038 |
40933 measured reflections |
R[F2 > 2σ(F2)] = 0.026 | H-atom parameters constrained |
wR(F2) = 0.058 | Δρmax = 0.54 e Å−3 |
S = 1.06 | Δρmin = −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 |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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 |
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. |
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 |
Mr | 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) |
Tmin, Tmax | 0.649, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 40933, 4484, 4045 |
Rint | 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 |
Δρmax, Δρmin (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).
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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).