organic compounds
1-(Prop-2-ynyl)indoline-2,3-dione
aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco, bInstitut National des Plantes Médicinales et Aromatiques, Université Sidi Mohamed Ben Abdallah, BP 2202 Fès, Morocco, cX-Ray Structure Analysis Unit, University of Regensburg, D-93053 Regensburg, Germany, and dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
*Correspondence e-mail: fatimazahrae_qachchachi@yahoo.fr
The structure of the title compound, C11H7NO2, is isotypic to that of its homologue, 1-octylindoline-2,3-dione [Qachchachi et al. (2013). Acta Cryst. E69, o1801]. The indoline ring and the two carbonyl O atoms are approximately coplanar, the largest deviation from the mean plane being 0.021 (1) Å for one of the O atoms. The mean plane through the fused ring system is nearly perpendicular to the propynyl group, as indicated by the N—C—C—C torsion angle of 77.9 (1)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds and π–π interactions between benzene rings [intercentroid distance = 3.5630 (10) Å], forming a three-dimensional structure.
CCDC reference: 988034
Related literature
For the biological activity of indoline derivatives, see: Malhotra et al. (2011); Ramachandran (2011); Smitha et al. (2008). For the structure of 1-octylindoline-2,3-dione, see: Qachchachi et al. (2013).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Agilent, 2013); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 988034
10.1107/S1600536814003973/tk5296sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814003973/tk5296Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814003973/tk5296Isup3.cml
Isatin (1H-indole-2,3-dione) is a synthetically versatile substrate,used for the synthesis of a large variety of
such as indoles and quinolines, and as a raw material for drug synthesis. Isatin has also been found in mammalian tissues, and its function as a modulator of biochemical processes has been the subject of several discussions. Isatin and its derivatives have aroused great attention in recent years due to their wide variety of biological activities, relevant to application as insecticides and fungicides and in a broad range of drug therapies, including as anti-cancer agents, anti-biotics and anti-depressants (Malhotra et al., 2011; Ramachandran, 2011; Smitha et al., 2008). In our work, we are interested in developing a new isatin derivative with the addition of alkyl halides to explore other applications (Scheme 1).The molecule of title compound is build up from a fused five- and six-membered rings linked, to the propynyl chain and to two carbonyl group O atoms as shown in Fig. 1. The indoline ring and the two carbonyl O atoms are nearly co-planar, with the largest deviation from the mean plane being 0.021 (1) Å for the O1 atom. The fused ring system plan is nearly perpendicular to the the propynyl chain as indicated by N1—C9—C10—C11 torsion angle of 77.9 (1)°. The structure of the title compound is similar to that of its homologue 1-octylindoline-2,3-dione (Qachchachi et al., 2013).
In the crystal, the molecules are linked by C—H···O1 hydrogen bonds, Table 1 and Fig. 2, to form layers in hte bc plane. Layers are connected by π—π interactions between centrosymmetrically related benzene rings [3.5630 (10) Å; -x, -y, -z] in the way to build a three-dimensional network.
To a solution of isatin (0.5 g, 3.4 mmol) dissolved in DMF (30 ml) was added potassium carbonate (0.61 g, 4.4 mmol), a catalytic quantity of tetra-n- butylammonium (0.1 g, 0.4 mmol) and 3-bromoprop-1-yne (0.3 ml, 3.7 mmol). The mixture was stirred for 48 h; the reaction was monitored by thin layer
The mixture was filtered and the solvent removed under vacuum. The solid obtained was recrystallized from ethanol to afford the title compound as red crystals in 88% yield (M.pt: 423 K).Data collection: CrysAlis PRO (Agilent, 2013); cell
CrysAlis PRO (Agilent, 2013); data reduction: CrysAlis PRO (Agilent, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).Fig. 1. Molecular plot the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. Intermolecular hydrogen interactions in the title compound. Hydrogen bonds are shown as dashed lines. |
C11H7NO2 | Z = 2 |
Mr = 185.18 | F(000) = 192 |
Triclinic, P1 | Dx = 1.439 Mg m−3 |
Hall symbol: -P 1 | Melting point: 423 K |
a = 7.0939 (7) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 7.9452 (7) Å | Cell parameters from 1851 reflections |
c = 8.5658 (6) Å | θ = 5.2–73.3° |
α = 80.464 (7)° | µ = 0.83 mm−1 |
β = 85.760 (7)° | T = 123 K |
γ = 63.881 (9)° | Plate, red |
V = 427.50 (6) Å3 | 0.15 × 0.13 × 0.02 mm |
Agilent SuperNova (Single source at offset, Atlas) diffractometer | 1627 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 1438 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.029 |
Detector resolution: 10.3546 pixels mm-1 | θmax = 73.5°, θmin = 5.2° |
ω scans | h = −8→8 |
Absorption correction: analytical (Clark & Reid, 1995) | k = −9→9 |
Tmin = 0.910, Tmax = 0.981 | l = −7→10 |
3081 measured reflections |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0429P)2 + 0.0993P] where P = (Fo2 + 2Fc2)/3 |
1627 reflections | (Δ/σ)max < 0.001 |
127 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
C11H7NO2 | γ = 63.881 (9)° |
Mr = 185.18 | V = 427.50 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.0939 (7) Å | Cu Kα radiation |
b = 7.9452 (7) Å | µ = 0.83 mm−1 |
c = 8.5658 (6) Å | T = 123 K |
α = 80.464 (7)° | 0.15 × 0.13 × 0.02 mm |
β = 85.760 (7)° |
Agilent SuperNova (Single source at offset, Atlas) diffractometer | 1627 independent reflections |
Absorption correction: analytical (Clark & Reid, 1995) | 1438 reflections with I > 2σ(I) |
Tmin = 0.910, Tmax = 0.981 | Rint = 0.029 |
3081 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.20 e Å−3 |
1627 reflections | Δρmin = −0.22 e Å−3 |
127 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against all reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on all data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.25017 (19) | 0.06257 (19) | 0.05480 (16) | 0.0180 (3) | |
C2 | 0.1753 (2) | 0.2210 (2) | −0.05932 (17) | 0.0211 (3) | |
H2 | 0.1510 | 0.3421 | −0.0368 | 0.025* | |
C3 | 0.1367 (2) | 0.1959 (2) | −0.20994 (16) | 0.0225 (3) | |
H3 | 0.0847 | 0.3028 | −0.2906 | 0.027* | |
C4 | 0.1719 (2) | 0.0202 (2) | −0.24516 (16) | 0.0224 (3) | |
H4 | 0.1440 | 0.0084 | −0.3486 | 0.027* | |
C5 | 0.2481 (2) | −0.1391 (2) | −0.12896 (16) | 0.0204 (3) | |
H5 | 0.2729 | −0.2602 | −0.1517 | 0.025* | |
C6 | 0.2867 (2) | −0.11607 (19) | 0.02066 (16) | 0.0186 (3) | |
C7 | 0.3621 (2) | −0.25174 (19) | 0.16566 (16) | 0.0201 (3) | |
C8 | 0.3703 (2) | −0.1326 (2) | 0.29023 (16) | 0.0204 (3) | |
C9 | 0.2676 (2) | 0.2094 (2) | 0.29379 (16) | 0.0222 (3) | |
H9A | 0.2986 | 0.3039 | 0.2198 | 0.027* | |
H9B | 0.3644 | 0.1648 | 0.3849 | 0.027* | |
C10 | 0.0499 (2) | 0.29983 (19) | 0.34996 (16) | 0.0210 (3) | |
C11 | −0.1255 (2) | 0.3711 (2) | 0.39699 (17) | 0.0249 (3) | |
H11 | −0.2657 | 0.4280 | 0.4346 | 0.030* | |
N1 | 0.30354 (18) | 0.04896 (16) | 0.21361 (13) | 0.0203 (3) | |
O1 | 0.40885 (16) | −0.41925 (14) | 0.19499 (12) | 0.0263 (3) | |
O2 | 0.42444 (16) | −0.19092 (15) | 0.42712 (12) | 0.0262 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0119 (6) | 0.0223 (6) | 0.0210 (6) | −0.0082 (5) | 0.0020 (5) | −0.0050 (5) |
C2 | 0.0172 (6) | 0.0193 (6) | 0.0270 (7) | −0.0082 (5) | 0.0014 (5) | −0.0040 (5) |
C3 | 0.0177 (6) | 0.0251 (7) | 0.0230 (7) | −0.0093 (5) | 0.0003 (5) | 0.0010 (5) |
C4 | 0.0196 (7) | 0.0296 (7) | 0.0192 (6) | −0.0116 (6) | 0.0015 (5) | −0.0050 (5) |
C5 | 0.0161 (6) | 0.0230 (7) | 0.0230 (6) | −0.0085 (5) | 0.0023 (5) | −0.0066 (5) |
C6 | 0.0143 (6) | 0.0196 (6) | 0.0218 (6) | −0.0073 (5) | 0.0015 (5) | −0.0039 (5) |
C7 | 0.0142 (6) | 0.0222 (7) | 0.0229 (6) | −0.0073 (5) | 0.0008 (5) | −0.0033 (5) |
C8 | 0.0150 (6) | 0.0247 (7) | 0.0223 (7) | −0.0096 (5) | 0.0014 (5) | −0.0031 (5) |
C9 | 0.0219 (7) | 0.0248 (7) | 0.0240 (7) | −0.0120 (6) | −0.0005 (5) | −0.0089 (5) |
C10 | 0.0260 (7) | 0.0204 (6) | 0.0193 (6) | −0.0117 (6) | −0.0025 (5) | −0.0042 (5) |
C11 | 0.0240 (7) | 0.0240 (7) | 0.0271 (7) | −0.0103 (6) | 0.0003 (6) | −0.0057 (5) |
N1 | 0.0196 (6) | 0.0213 (6) | 0.0204 (6) | −0.0085 (5) | −0.0003 (4) | −0.0051 (4) |
O1 | 0.0261 (5) | 0.0193 (5) | 0.0307 (5) | −0.0079 (4) | −0.0018 (4) | −0.0012 (4) |
O2 | 0.0266 (5) | 0.0343 (6) | 0.0197 (5) | −0.0153 (5) | −0.0027 (4) | −0.0016 (4) |
C1—C2 | 1.379 (2) | C6—C7 | 1.4622 (18) |
C1—C6 | 1.4034 (18) | C7—O1 | 1.2072 (17) |
C1—N1 | 1.4131 (17) | C7—C8 | 1.5589 (18) |
C2—C3 | 1.402 (2) | C8—O2 | 1.2111 (18) |
C2—H2 | 0.9500 | C8—N1 | 1.3663 (18) |
C3—C4 | 1.387 (2) | C9—N1 | 1.4631 (17) |
C3—H3 | 0.9500 | C9—C10 | 1.470 (2) |
C4—C5 | 1.394 (2) | C9—H9A | 0.9900 |
C4—H4 | 0.9500 | C9—H9B | 0.9900 |
C5—C6 | 1.3872 (19) | C10—C11 | 1.188 (2) |
C5—H5 | 0.9500 | C11—H11 | 0.9500 |
C2—C1—C6 | 121.15 (12) | O1—C7—C6 | 131.72 (13) |
C2—C1—N1 | 128.42 (13) | O1—C7—C8 | 123.44 (12) |
C6—C1—N1 | 110.42 (12) | C6—C7—C8 | 104.83 (11) |
C1—C2—C3 | 117.21 (13) | O2—C8—N1 | 127.55 (13) |
C1—C2—H2 | 121.4 | O2—C8—C7 | 126.40 (13) |
C3—C2—H2 | 121.4 | N1—C8—C7 | 106.05 (11) |
C4—C3—C2 | 122.21 (13) | N1—C9—C10 | 111.50 (11) |
C4—C3—H3 | 118.9 | N1—C9—H9A | 109.3 |
C2—C3—H3 | 118.9 | C10—C9—H9A | 109.3 |
C3—C4—C5 | 120.08 (12) | N1—C9—H9B | 109.3 |
C3—C4—H4 | 120.0 | C10—C9—H9B | 109.3 |
C5—C4—H4 | 120.0 | H9A—C9—H9B | 108.0 |
C6—C5—C4 | 118.27 (13) | C11—C10—C9 | 179.14 (16) |
C6—C5—H5 | 120.9 | C10—C11—H11 | 180.0 |
C4—C5—H5 | 120.9 | C8—N1—C1 | 111.08 (11) |
C5—C6—C1 | 121.08 (13) | C8—N1—C9 | 123.22 (12) |
C5—C6—C7 | 131.32 (13) | C1—N1—C9 | 125.25 (12) |
C1—C6—C7 | 107.60 (11) | ||
C6—C1—C2—C3 | 0.27 (19) | O1—C7—C8—O2 | 0.7 (2) |
N1—C1—C2—C3 | 179.20 (13) | C6—C7—C8—O2 | 179.86 (13) |
C1—C2—C3—C4 | −0.2 (2) | O1—C7—C8—N1 | −179.02 (13) |
C2—C3—C4—C5 | 0.0 (2) | C6—C7—C8—N1 | 0.16 (14) |
C3—C4—C5—C6 | 0.04 (19) | O2—C8—N1—C1 | −178.89 (13) |
C4—C5—C6—C1 | 0.04 (19) | C7—C8—N1—C1 | 0.81 (14) |
C4—C5—C6—C7 | 178.89 (13) | O2—C8—N1—C9 | −6.2 (2) |
C2—C1—C6—C5 | −0.20 (19) | C7—C8—N1—C9 | 173.50 (11) |
N1—C1—C6—C5 | −179.30 (12) | C2—C1—N1—C8 | 179.43 (13) |
C2—C1—C6—C7 | −179.30 (12) | C6—C1—N1—C8 | −1.55 (16) |
N1—C1—C6—C7 | 1.60 (15) | C2—C1—N1—C9 | 6.9 (2) |
C5—C6—C7—O1 | −0.9 (3) | C6—C1—N1—C9 | −174.06 (12) |
C1—C6—C7—O1 | 178.03 (14) | C10—C9—N1—C8 | −90.49 (15) |
C5—C6—C7—C8 | 179.97 (14) | C10—C9—N1—C1 | 81.16 (16) |
C1—C6—C7—C8 | −1.05 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.95 | 2.62 | 3.3901 (17) | 139 |
C9—H9A···O1ii | 0.99 | 2.61 | 3.4747 (18) | 146 |
C9—H9B···O2iii | 0.99 | 2.37 | 3.2987 (17) | 156 |
Symmetry codes: (i) −x+1, −y−1, −z; (ii) x, y+1, z; (iii) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.95 | 2.62 | 3.3901 (17) | 139 |
C9—H9A···O1ii | 0.99 | 2.61 | 3.4747 (18) | 146 |
C9—H9B···O2iii | 0.99 | 2.37 | 3.2987 (17) | 156 |
Symmetry codes: (i) −x+1, −y−1, −z; (ii) x, y+1, z; (iii) −x+1, −y, −z+1. |
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