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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160381
doi:10.1107/S2414314616003813

1-Benzyl-5-methyl­indoline-2,3-dione

N. Sharmila,a T. V. Sundar,a* G. Satishb and P. Venkatesanb

aPostgraduate and Research Department of Physics, National College (Autonomous), Tiruchirappalli 620 001, Tamilnadu, India, and bSchool of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamilnadu, India
*Correspondence e-mail: sunvag@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 23 February 2016; accepted 7 March 2016; online 15 March 2016)

The title compound, C16H13NO2, is an isatin (indole-2,3-dione) derivative. The isatin moiety is almost planar with an r.m.s. deviation of 0.022 Å, and its mean plane makes a dihedral angle of 74.19 (12)° with the benzyl ring. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds, forming C(6) chains propagating along the a-axis direction. The chains are linked via C—H⋯π inter­actions, forming slabs parallel to the ab plane. Within the slabs there are weak π–π inter­actions present involving inversion-related isatin moieties.

CCDC reference: 1458273

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Isatins (indoline-2,3-diones) are an important family of heterocyclic compounds which are biologically active and of significant importance in medicinal chemistry. A variety of biological activities are associated with isatins including CNS (central nervous system) activities as potentiation of pentobarbitone induced necrosis. They also display analgesic, anti­convulsant, anti­depressant, anti-inflammatory and anti­microbial effects on the central nervous system. Isatins are capable of crossing the blood–brain barrier (Bhrigu et al., 2010[Bhrigu, B., Pathak, D., Siddiqui, N., Alam, M. S. & Ahsan, W. (2010). Int. J. Pharm. Sci. Drug. Res. 2, 229-235.]; Fathimunnisa et al., 2015[Fathimunnisa, M., Manikandan, H., Selvanayagam, S. & Sridhar, B. (2015). Acta Cryst. E71, 915-918.]; Gürsoy & Karali, 2003[Gürsoy, A. & Karali, N. (2003). Eur. J. Med. Chem. 38, 633-643.]; Ilangovan & Satish, 2014[Ilangovan, A. & Satish, G. (2014). J. Org. Chem. 79, 4984-4991.]; Mathur & Nain, 2014[Mathur, G. & Nain, S. (2014). Med. Chem. 4, 417-427.]; Verma et al., 2004[Verma, M., Pandeya, S. N., Singh, K. N. & Stables, J. P. (2004). Acta Pharm. 54, 49-56.]). As part of our inter­est in the structural investigations of isatin derivatives, we report herein on the crystal structure determination and the geometry optimization of the title compound (I). Theoretical calculations of the mol­ecular structure using MOPAC2012′s PM7 geometry optimization algorithm (Stewart, 2012[Stewart, J. J. P. (2012). Comput. Chem. 66 Version 15.286W, web: https://OpenMOPAC.net.]; Maia et al., 2012[Maia, J. D. C., Carvalho, G. A. U., Mangueira, C. P. Jr, Santana, S. R., Cabral, L. A. F. & Rocha, G. B. (2012). J. Chem. Theory Comput. 8, 3072-3081.]) are in satisfactory agreement with the results of the X-ray crystal structure analysis.

The mol­ecular structure of the title compound, (I), is illustrated in Fig. 1[link]. In the isatin (indoline-2,3-dione) moiety, which is almost planar [r.m.s. deviation of 0.022 Å; maximum deviation of 0.036 (2) Å for atom C7]. Its mean plane makes a dihedral angle of 74.19 (12)° with the benzyl ring (C10–C15). This is similar to the values observed in related structures, for example {1-benzyl-4,5,6- tri­meth­oxy­indoline-2,3-dione (II), [73.04 (7)°] and 1-benzyl- 5-fluoro­indoline-2,3-dione (III), [76.82 (11)°]} (Sharmila et al., 2015[Sharmila, N., Sundar, T. V., Satish, G., Ilangovan, A. & Venkatesan, P. (2015). Acta Cryst. C71, 975-978.]). The superimposed fit (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graphics Modell. 19, 557-559.]) of the isatin group of the title compound (I) (atoms C1–C8, N1, O1 and O2) gives an r.m.s deviation of 0.065 Å with mol­ecule (II) and 0.034 Å with mol­ecule (III), while that with its energy-minimized counterpart gives 0.057 Å. The bond lengths and bond angles of the isatin moiety of compound (I) are also comparable with the values observed for related structures (Helliwell et al., 2012[Helliwell, M., Baradarani, M. M., Mohammadnejadaghdam, R., Afghan, A. & Joule, J. A. (2012). Acta Cryst. E68, o233.]; Lötter et al., 2007[Lötter, A. N. C., Fernandes, M. A., van Otterlo, W. A. L. & de Koning, C. B. (2007). Acta Cryst. C63, o157-o159.]). The sum of the angles around the N atom is 360°, indicating the absence of an sp3 lone pair.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound (I), showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds, forming chains propagating along the a-axis direction (Table 1[link] and Fig. 2[link]). The chains are linked by C—H⋯π inter­actions, forming slabs lying parallel to the ab plane. Within the slabs there are weak slipped parallel π–π inter­actions present involving inversion-related indoline ring systems [Cg1⋯Cg2i = 3.843 (1) Å, shortest inter-planar distance = 3.291 (1) Å, slippage 1.884 Å; Cg1 and Cg2 are the centroids of rings N1/C1/C6–C8 and C1–C6, respectively; symmetry code: (i) −x, −y + 1, −z + 1].

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the benzyl ring, C10–C15.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯O2i 0.93 2.53 3.446 (3) 169
C5—H5⋯Cg3ii 0.93 2.91 3.818 (3) 165
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (ii) -x, -y+1, -z+1.
[Figure 2]
Figure 2
Crystal packing of the title compound (I), viewed along the b axis, showing the C—H⋯O hydrogen bonds as dashed lines (see Table 1[link]), and C—H⋯π inter­actions as black lines. H atoms not involved in these inter­actions have been omitted for clarity.

A geometry optimization of (I) with Parameterized Model 7 computation was performed using MOPAC2012. Hartree–Fock closed-shell (restricted) wavefunctions were used for calculations. The HOMO and LUMO energy levels were found to be −8.962 and −1.158 eV, respectively. The total energy and dipole moment of the title mol­ecule are −2916.87 eV and 5.244 Debye, respectively. When compared with the crystal structure, in the geometry optimized structure it is observed that the N1—C1 and N1—C8 bond lengths changed from 1.414 and 1.370 Å to 1.411 and 1.419 Å, respectively. The C8—N1—C1 and C8—N1—C9 bond angles decreased from 110.60 and 123.4°, respectively, to 110.12 and 122.27 °, respectively.

The relative conformation about the bond joining the isatin moiety and the benzyl group of the structure is defined by the C1—N1—C9—C10 torsion angle. It shows an anti-clinal conformation [98.2 (3)°] in the crystal structure (I), but takes a syn-clinal conformation (72.38 °) in the optimized structure. However, the torsion angle C8—N1—C9—C10 remained almost the same, −81.4 (3) and −87.36°, respectively. A superimposed fit of (I) with its energy-minimized mol­ecular structure gives an r.m.s. deviation of 0.473 Å (Fig. 3[link]). This indicates a greater twist leading to further separation between the isatin moiety and the benzene ring. This suggests that the crystal packing is influenced by the collective effect of the inter­molecular inter­actions.

[Figure 3]
Figure 3
A superimposed fit of the title compound (red) and its energy-minimized counterpart (blue).

Synthesis and crystallization

To a mixture of benzyl-(2-ethynyl-4-methyl­phen­yl)-amine (100 mg, 0.451 mmol) and I2 (22.9 mg, 0.09 mmol), dimethyl sulfoxide (3 ml) was added at ambient temperature and the mixture was heated at 373 K for 5 h in air. Progress of the reaction was monitored by thin layer chromatography. Upon completion, the reaction mixture was allowed to cool to ambient temperature and quenched with aq. sodium thio­sulfate and ethyl acetate. The organic phase was separated, dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel column chromatography using hexane-ethyl acetate (9:1 v/v) as eluent. The title compound was obtained as a red solid (yield: 85%, 96.5 mg; mp: 416–418 K). It was dissolved in an hexa­ne–ethyl acetate mixture (9:1 v/v) and subjected to slow evaporation at room temperature (298 K), giving red block-like crystals after 2 d. Spectroscopic analysis: 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 7.44 (s, 1H), 7.39–7.29 (m, 6H), 6.68 (d, J = 8.0 Hz, 1H), 4.93 (s, 2H), 2.32 (s, 3H); 13CNMR (100 MHz, CDCl3, δ, p.p.m.): 183.5, 158.4, 148.5, 138.7,134.7, 133.7, 129.0, 128.1, 127.4, 125.7, 117.7, 110.8, 44.0, 20.6.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C16H13NO2
Mr 251.27
Crystal system, space group Orthorhombic, Pbca
Temperature (K) 293
a, b, c (Å) 14.6122 (15), 8.3882 (9), 20.911 (2)
V (Å3) 2563.1 (5)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.35 × 0.30 × 0.25
 
Data collection
Diffractometer Bruker Kappa APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.970, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections 18203, 3091, 1652
Rint 0.051
(sin θ/λ)max (Å−1) 0.666
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.164, 1.05
No. of reflections 3091
No. of parameters 173
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.19, −0.16
Computer programs: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), QMOL (Gans & Shalloway, 2001[Gans, J. & Shalloway, D. (2001). J. Mol. Graphics Modell. 19, 557-559.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), MOPAC (Stewart, 2012[Stewart, J. J. P. (2012). Comput. Chem. 66 Version 15.286W, web: https://OpenMOPAC.net.]), WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data

CCDC reference: 1458273

Crystal structure: contains datablocks I, Global. DOI: 10.1107/S2414314616003813/su4017sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616003813/su4017Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616003813/su4017Isup3.cml

checkCIF report


Experimental top

To a mixture of benzyl-(2-ethynyl-4-methylphenyl)-amine (100 mg, 0.451 mmol) and I2 (22.9 mg, 0.09 mmol), dimethyl sulfoxide (3 ml) was added at ambient temperature and the mixture was heated at 373 K for 5 h in air. Progress of the reaction was monitored by thin layer chromatography. Upon completion, the reaction mixture was allowed to cool to ambient temperature and quenched with aq. sodium thiosulfate and ethyl acetate. The organic phase was separated, dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel column chromatography using hexane-ethyl acetate (9:1 v/v) as eluent. The title compound was obtained as a red solid (yield: 85%, 96.5 mg; mp: 416–418 K). It was dissolved in an hexane–ethyl acetate mixture (9:1 v/v) and subjected to slow evaporation at room temperature (298 K), giving red block-like crystals after 2 d. Spectroscopy analysis: 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 7.44 (s, 1H), 7.39–7.29 (m, 6H), 6.68 (d, J = 8.0 Hz, 1H), 4.93 (s, 2H), 2.32 (s, 3H); 13CNMR (100 MHz, CDCl3, δ, p.p.m.): 183.5, 158.4, 148.5, 138.7,134.7, 133.7, 129.0, 128.1, 127.4, 125.7, 117.7, 110.8, 44.0, 20.6.

Refinement top

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

Structure description top

Isatins (indoline-2,3-diones) are an important family of heterocyclic compounds which are biologically active and of significant importance in medicinal chemistry. A variety of biological activities are associated with isatins including CNS activities as potentiation of pentobarbitone induces necrosis, analgesic, anticonvulsant, antidepressant, anti-inflammatory and antimicrobial effects on the central nervous system. Isatins are capable of crossing the blood–brain barrier (Bhrigu et al., 2010; Fathimunnisa et al., 2015; Gürsoy & Karali, 2003; Ilangovan & Satish, 2014; Mathur & Nain, 2014; Verma et al., 2004). As part of our interest in the structural investigations of isatin derivatives, we report herein on the crystal structure determination and the geometry optimization of the title compound (I). Theoretical calculations of the molecular structure using MOPAC2012's PM7 geometry optimization algorithm (Stewart, 2012; Maia et al., 2012) are in satisfactory agreement with the results of the X-ray crystal structure analysis.

The molecular structure of the title compound, (I), is illustrated in Fig. 1. In the isatin (indoline-2,3-dione) moiety, which is almost planar [r.m.s. deviation of 0.022 Å; maximum deviation of 0.036 (2) Å for atom C7]. Its mean plane makes a dihedral angle of 74.19 (12)° with the benzyl ring (C10–C15). This is similar to the values observed in related structures, for example {1-benzyl-4,5,6- trimethoxyindoline-2,3-dione (II), [73.04 (7)°] and 1-benzyl- 5-fluoroindoline-2,3-dione (III), [76.82 (11)°]} (Sharmila et al., 2015). The superimposed fit (Gans & Shalloway, 2001) of the isatin group of the title compound (I) (atoms C1–C8, N1, O1 and O2) gives an r.m.s deviation of 0.065 Å with molecule (II) and 0.034 Å with molecule (III), while that with its energy-minimized counterpart gives 0.057 Å. The bond lengths and bond angles of the isatin moiety of compound (I) are also comparable with the values observed for related structures (Helliwell et al., 2012; Lötter et al., 2007). The sum of the angles around the N atom is 360°, indicating the absence of an sp3 lone pair.

In the crystal, molecules are linked via C—H···O hydrogen bonds, forming chains propagating along the a-axis direction (Table 1 and Fig. 2). The chains are linked by C—H···π interactions, forming slabs lying parallel to the ab plane. Within the slabs there are weak slipped parallel π–π interactions present involving inversion-related indoline ring systems [Cg1···Cg2i = 3.843 (1) Å, shortest inter-planar distance = 3.291 (1) Å, slippage 1.884 Å; Cg1 and Cg2 are the centroids of rings N1/C1/C6–C8 and C1–C6, respectively; symmetry code: (i) −x, −y + 1, −z + 1].

A geometry optimization of (I) with Parameterized Model 7 computation was performed using MOPAC2012. Hartree–Fock closed-shell (restricted) wavefunctions were used for calculations. The HOMO and LUMO energy levels were found to be −8.962 and −1.158 eV, respectively. The total energy and dipole moment of the title molecule are −2916.87 eV and 5.244 Debye, respectively. When compared with the crystal structure, in the geometry optimized structure it is observed that the N1—C1 and N1—C8 bond lengths changed from 1.414 and 1.370 Å to 1.411 and 1.419 Å, respectively. The C8—N1—C1 and C8—N1—C9 bond angles decreased from 110.60 and 123.4°, respectively, to 110.12 and 122.27 °, respectively.

The relative conformation about the bond joining the isatin moiety and the benzyl group of the structure is defined by the C1—N1—C9—C10 torsion angle. It shows an anti-clinal conformation [98.2 (3)°] in the crystal structure (I), but takes a syn-clinal conformation (72.38 °) in the optimized structure. However, the torsion angle C8—N1—C9—C10 remained almost the same, −81.4 (3) and −87.36°, respectively. A superimposed fit of (I) with its energy-minimized molecular structure gives an r.m.s. deviation of 0.473 Å (Fig. 3). This indicates a greater twist leading to further separation between the isatin moiety and the benzene ring. This suggests that the crystal packing is influenced by the collective effect of the intermolecular interactions.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: QMOL (Gans & Shalloway, 2001), Mercury (Macrae et al., 2008) and MOPAC (Stewart, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (I), showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound (I), viewed along the b axis, showing the C—H···O hydrogen bonds as dashed lines (see Table 1), and C—H···π interactions as black lines. H atoms not involved in these interactions have been omitted for clarity.
[Figure 3] Fig. 3. A superimposed fit of the title compound (red) and its energy-minimized counterpart (blue).
1-Benzyl-5-methylindoline-2,3-dione top
Crystal data top
C16H13NO2Dx = 1.302 Mg m−3
Mr = 251.27Melting point < 418 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 14.6122 (15) ÅCell parameters from 2925 reflections
b = 8.3882 (9) Åθ = 5.6–44.9°
c = 20.911 (2) ŵ = 0.09 mm−1
V = 2563.1 (5) Å3T = 293 K
Z = 8Block, red
F(000) = 10560.35 × 0.30 × 0.25 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3091 independent reflections
Radiation source: fine-focus sealed tube1652 reflections with I > 2σ(I)
Grapite monochromatorRint = 0.051
ω and φ scanθmax = 28.3°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −11→18
Tmin = 0.970, Tmax = 0.979k = −11→11
18203 measured reflectionsl = −27→27
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0579P)2 + 0.8201P]
where P = (Fo2 + 2Fc2)/3
3091 reflections(Δ/σ)max = 0.001
173 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.16 e Å−3
Crystal data top
C16H13NO2V = 2563.1 (5) Å3
Mr = 251.27Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 14.6122 (15) ŵ = 0.09 mm−1
b = 8.3882 (9) ÅT = 293 K
c = 20.911 (2) Å0.35 × 0.30 × 0.25 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer		3091 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		1652 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.979Rint = 0.051
18203 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0570 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 1.05Δρmax = 0.19 e Å−3
3091 reflectionsΔρmin = −0.16 e Å−3
173 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.08992 (12)0.2173 (2)0.53228 (9)0.0517 (5)
O1−0.04615 (12)0.0928 (2)0.55743 (9)0.0698 (5)
O2−0.11076 (11)0.2770 (2)0.44577 (9)0.0714 (5)
C10.11891 (14)0.3272 (2)0.48514 (11)0.0454 (5)
C20.20581 (15)0.3881 (3)0.47456 (11)0.0507 (6)
H20.25530.35700.49960.061*
C30.21631 (15)0.4966 (3)0.42539 (11)0.0512 (6)
H30.27430.53830.41800.061*
C40.14499 (15)0.5465 (3)0.38655 (11)0.0513 (6)
C50.05881 (15)0.4812 (3)0.39747 (11)0.0509 (6)
H50.00960.51070.37190.061*
C60.04655 (13)0.3728 (3)0.44619 (11)0.0462 (5)
C7−0.03384 (15)0.2825 (3)0.46708 (11)0.0522 (6)
C8−0.00124 (16)0.1836 (3)0.52531 (12)0.0545 (6)
C90.14700 (17)0.1481 (3)0.58222 (13)0.0619 (7)
H9A0.21050.15250.56890.074*
H9B0.13070.03680.58770.074*
C100.13695 (15)0.2328 (3)0.64541 (12)0.0555 (6)
C110.0863 (2)0.1681 (4)0.69456 (16)0.0836 (9)
H110.05960.06840.68930.100*
C120.0745 (2)0.2489 (6)0.75132 (17)0.1014 (12)
H120.03970.20380.78380.122*
C130.1143 (2)0.3966 (6)0.76008 (16)0.0959 (11)
H130.10730.45020.79870.115*
C140.1636 (2)0.4628 (4)0.71219 (16)0.0877 (9)
H140.18940.56330.71750.105*
C150.17557 (18)0.3809 (4)0.65538 (14)0.0709 (8)
H150.21050.42670.62310.085*
C160.15996 (18)0.6691 (3)0.33497 (13)0.0728 (8)
H16A0.15220.62020.29380.109*
H16B0.22080.71130.33840.109*
H16C0.11640.75390.33980.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0366 (11)0.0446 (11)0.0739 (13)0.0017 (8)−0.0005 (8)−0.0055 (10)
O10.0533 (11)0.0584 (11)0.0978 (14)−0.0094 (9)0.0173 (9)−0.0061 (10)
O20.0309 (9)0.0824 (13)0.1009 (13)−0.0079 (8)−0.0058 (8)−0.0110 (11)
C10.0340 (12)0.0393 (12)0.0629 (14)0.0024 (9)0.0021 (9)−0.0144 (10)
C20.0306 (12)0.0482 (13)0.0732 (15)0.0031 (9)−0.0054 (10)−0.0107 (12)
C30.0335 (12)0.0478 (14)0.0724 (16)−0.0018 (10)0.0057 (10)−0.0117 (12)
C40.0403 (14)0.0526 (15)0.0609 (15)0.0040 (10)0.0061 (10)−0.0112 (11)
C50.0347 (13)0.0600 (16)0.0580 (14)0.0078 (10)−0.0015 (9)−0.0152 (12)
C60.0300 (11)0.0466 (13)0.0622 (14)0.0011 (9)0.0014 (9)−0.0183 (11)
C70.0326 (12)0.0508 (14)0.0733 (15)0.0013 (10)0.0037 (10)−0.0214 (12)
C80.0412 (14)0.0425 (13)0.0799 (16)−0.0041 (10)0.0109 (11)−0.0168 (12)
C90.0467 (15)0.0422 (14)0.097 (2)0.0067 (11)−0.0007 (12)0.0067 (13)
C100.0364 (13)0.0557 (15)0.0743 (17)0.0056 (11)−0.0050 (10)0.0184 (13)
C110.069 (2)0.088 (2)0.094 (2)−0.0067 (16)−0.0008 (16)0.038 (2)
C120.084 (2)0.147 (4)0.072 (2)0.001 (2)0.0058 (18)0.039 (2)
C130.073 (2)0.148 (4)0.067 (2)0.019 (2)−0.0126 (16)−0.003 (2)
C140.077 (2)0.100 (3)0.087 (2)−0.0068 (18)−0.0110 (17)−0.009 (2)
C150.0583 (17)0.076 (2)0.0782 (19)−0.0132 (14)0.0028 (13)0.0065 (16)
C160.0578 (18)0.086 (2)0.0751 (17)0.0021 (14)0.0087 (13)0.0009 (16)
Geometric parameters (Å, º) top
N1—C81.370 (3)C9—C101.508 (4)
N1—C11.414 (3)C9—H9A0.9700
N1—C91.457 (3)C9—H9B0.9700
O1—C81.209 (3)C10—C111.378 (4)
O2—C71.210 (3)C10—C151.380 (4)
C1—C21.386 (3)C11—C121.377 (5)
C1—C61.388 (3)C11—H110.9300
C2—C31.382 (3)C12—C131.381 (5)
C2—H20.9300C12—H120.9300
C3—C41.386 (3)C13—C141.353 (5)
C3—H30.9300C13—H130.9300
C4—C51.392 (3)C14—C151.384 (4)
C4—C161.506 (3)C14—H140.9300
C5—C61.377 (3)C15—H150.9300
C5—H50.9300C16—H16A0.9600
C6—C71.464 (3)C16—H16B0.9600
C7—C81.549 (3)C16—H16C0.9600
C8—N1—C1110.60 (19)C10—C9—H9A109.1
C8—N1—C9123.4 (2)N1—C9—H9B109.1
C1—N1—C9126.00 (19)C10—C9—H9B109.1
C2—C1—C6120.2 (2)H9A—C9—H9B107.8
C2—C1—N1128.7 (2)C11—C10—C15117.5 (3)
C6—C1—N1111.11 (19)C11—C10—C9121.4 (3)
C3—C2—C1117.6 (2)C15—C10—C9121.1 (2)
C3—C2—H2121.2C12—C11—C10121.1 (3)
C1—C2—H2121.2C12—C11—H11119.5
C2—C3—C4123.5 (2)C10—C11—H11119.5
C2—C3—H3118.3C11—C12—C13120.2 (3)
C4—C3—H3118.3C11—C12—H12119.9
C3—C4—C5117.7 (2)C13—C12—H12119.9
C3—C4—C16121.1 (2)C14—C13—C12119.6 (3)
C5—C4—C16121.2 (2)C14—C13—H13120.2
C6—C5—C4119.9 (2)C12—C13—H13120.2
C6—C5—H5120.0C13—C14—C15119.9 (3)
C4—C5—H5120.0C13—C14—H14120.0
C5—C6—C1121.1 (2)C15—C14—H14120.0
C5—C6—C7131.8 (2)C10—C15—C14121.7 (3)
C1—C6—C7107.1 (2)C10—C15—H15119.2
O2—C7—C6130.9 (2)C14—C15—H15119.2
O2—C7—C8123.7 (2)C4—C16—H16A109.5
C6—C7—C8105.36 (19)C4—C16—H16B109.5
O1—C8—N1126.8 (2)H16A—C16—H16B109.5
O1—C8—C7127.4 (2)C4—C16—H16C109.5
N1—C8—C7105.78 (19)H16A—C16—H16C109.5
N1—C9—C10112.60 (19)H16B—C16—H16C109.5
N1—C9—H9A109.1
C8—N1—C1—C2−178.0 (2)C1—N1—C8—O1179.0 (2)
C9—N1—C1—C22.3 (3)C9—N1—C8—O1−1.3 (4)
C8—N1—C1—C61.5 (2)C1—N1—C8—C70.2 (2)
C9—N1—C1—C6−178.2 (2)C9—N1—C8—C7179.89 (19)
C6—C1—C2—C31.4 (3)O2—C7—C8—O1−1.6 (4)
N1—C1—C2—C3−179.2 (2)C6—C7—C8—O1179.5 (2)
C1—C2—C3—C4−0.2 (3)O2—C7—C8—N1177.2 (2)
C2—C3—C4—C5−1.0 (3)C6—C7—C8—N1−1.7 (2)
C2—C3—C4—C16178.1 (2)C8—N1—C9—C10−81.4 (3)
C3—C4—C5—C61.0 (3)C1—N1—C9—C1098.2 (3)
C16—C4—C5—C6−178.1 (2)N1—C9—C10—C11103.5 (3)
C4—C5—C6—C10.2 (3)N1—C9—C10—C15−74.2 (3)
C4—C5—C6—C7−177.8 (2)C15—C10—C11—C120.2 (4)
C2—C1—C6—C5−1.4 (3)C9—C10—C11—C12−177.5 (3)
N1—C1—C6—C5179.02 (19)C10—C11—C12—C13−0.5 (5)
C2—C1—C6—C7176.97 (19)C11—C12—C13—C141.1 (5)
N1—C1—C6—C7−2.6 (2)C12—C13—C14—C15−1.4 (5)
C5—C6—C7—O21.9 (4)C11—C10—C15—C14−0.5 (4)
C1—C6—C7—O2−176.2 (2)C9—C10—C15—C14177.2 (2)
C5—C6—C7—C8−179.3 (2)C13—C14—C15—C101.2 (5)
C1—C6—C7—C82.6 (2)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the benzyl ring, C10–C15.
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.533.446 (3)169
C5—H5···Cg3ii0.932.913.818 (3)165
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the benzyl ring, C10–C15.
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.533.446 (3)169
C5—H5···Cg3ii0.932.913.818 (3)165
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC16H13NO2
Mr251.27
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)14.6122 (15), 8.3882 (9), 20.911 (2)
V (Å3)2563.1 (5)
Z8
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.35 × 0.30 × 0.25
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.970, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections		18203, 3091, 1652
Rint0.051
(sin θ/λ)max (Å−1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.164, 1.05
No. of reflections3091
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.19, −0.16

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), QMOL (Gans & Shalloway, 2001), Mercury (Macrae et al., 2008) and MOPAC (Stewart, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

 

Acknowledgements

NS thanks the Sophisticated Analytical Instrument Facility (SAIF), Sophisticated Test and Instrumentation Centre (STIC), Cochin University, Cochin, Kerala, India, for help with the data collection and Professor A. Ilangovan, School of Chemistry, Bharathidasan University, India, for fruitful discussions.

References

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160381
doi:10.1107/S2414314616003813
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