3-(1H-Indol-3-yl)-2-benzo­furan-1(3H)-one

Anil Kumar, R.; Naveen, S.; Abdul Rahiman, M.; Mahadevan, K.M.; Kumara, M.N.; Lokanath, N.K.; Warad, I.

doi:10.1107/S2414314617001079

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 1| January 2017| x170107

https://doi.org/10.1107/S2414314617001079

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3-(1H-Indol-3-yl)-2-benzofuran-1(3H)-one

R. Anil Kumar,^a S. Naveen,^b M. Abdul Rahiman,^c K. M. Mahadevan,^a M. N. Kumara,^d N. K. Lokanath ^e ^* and Ismail Warad ^f ^*

^aDepartment of Chemistry, Kuvempu University, PG Centre, Kadur 577 548, India, ^bInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, ^cDepartment of PG Studies in Chemistry, Government Science College, Hassan 573 201, India, ^dDepartment of Chemistry, Yuvarajas College, University of Mysore, Mysuru 570 005, India, ^eDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, and ^fDepartment of Chemistry, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian Territories
^*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in, khalil.i@najah.edu

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 20 January 2017; accepted 21 January 2017; online 24 January 2017)

In the title compound, C₁₆H₁₁NO₂, the benzofuran and indole ring systems are nearly orthogonal, subtending a dihedral angle of 86.55 (4)°. The crystal structure features an N—H⋯O hydrogen bond, which leads to the formation of chains propagating along the a-axis direction.

Keywords: crystal structure; indoles; hydrogen bonding.

CCDC reference: 1528890

Structure description

The indole subunit is widely observed in a plethora of natural and synthetic compounds characterized by a variety of biological and pharmacological activities (Mahboobi et al., 2006 ). Indole derivatives form the basis of a range of pharmaceuticals and a high level of activity continues in the search for new indole-based medicinal agents (Anil Kumar et al., 2016a ). In view of the broad spectrum of applications associated with indoles and as a part of our ongoing work on such molecules (Anil Kumar et al., 2016b ), we report herein the synthesis and crystal structure of the title compound.

The structure of the molecule is shown in Fig. 1. The dihedral angle value of 86.55 (4)° between the planes of the benzofuran and indole ring systems indicates that they are nearly orthogonal to one another. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, forming chains propagating along the a-axis direction (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.86	2.07	2.8398 (16)	149
Symmetry code: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids for the non-H atoms are drawn at the 50% probability level.

Figure 2
Packing of the molecules viewed along the c axis, with N—H⋯O hydrogen bonds drawn as blue lines.

Synthesis and crystallization

The synthesis of the title compound was accomplished by condensation reaction between commercially available indole and 2-formylbenzoic acid in glacial acetic acid at room temperature for 4–6 h. The resultant crude product was purified by recrystallization by using methanol as solvent to get colorless crystals. Yield: 83%, m.p. 174–176 °C.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₆H₁₁NO₂
M_r	249.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	16.522 (3), 7.6439 (14), 19.331 (4)
V (Å³)	2441.4 (8)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	0.73
Crystal size (mm)	0.30 × 0.28 × 0.25

Data collection
Diffractometer	Bruker X8 Proteum
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.811, 0.839
No. of measured, independent and observed [I > 2σ(I)] reflections	11928, 1999, 1970
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.585

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.086, 1.09
No. of reflections	1999
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1528890

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617001079/xu4022sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001079/xu4022Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617001079/xu4022Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

3-(1H-Indol-3-yl)-2-benzofuran-1(3H)-one top

Crystal data top

C₁₆H₁₁NO₂	F(000) = 1040
M_r = 249.26	D_x = 1.356 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1970 reflections
a = 16.522 (3) Å	θ = 5.3–64.3°
b = 7.6439 (14) Å	µ = 0.73 mm⁻¹
c = 19.331 (4) Å	T = 296 K
V = 2441.4 (8) Å³	Rectangle, white
Z = 8	0.30 × 0.28 × 0.25 mm

Data collection top

Bruker X8 Proteum diffractometer	1999 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1970 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.036
Detector resolution: 18.4 pixels mm^-1	θ_max = 64.3°, θ_min = 5.3°
φ and ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −8→7
T_min = 0.811, T_max = 0.839	l = −22→22
11928 measured reflections

Refinement top

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0342P)² + 1.1739P] where P = (F_o² + 2F_c²)/3
1999 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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.

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

	x	y	z	U_iso*/U_eq
O1	0.43433 (5)	0.84507 (12)	0.28595 (4)	0.0232 (3)
O2	0.31751 (6)	0.89685 (13)	0.34137 (5)	0.0285 (3)
N1	0.70014 (7)	0.92519 (16)	0.26536 (6)	0.0284 (4)
C1	0.68634 (8)	0.97689 (17)	0.33228 (7)	0.0237 (4)
C2	0.73445 (8)	1.07594 (18)	0.37663 (8)	0.0310 (4)
C3	0.70652 (9)	1.10207 (19)	0.44267 (8)	0.0335 (4)
C4	0.63269 (8)	1.03069 (19)	0.46506 (8)	0.0297 (4)
C5	0.58456 (8)	0.93417 (17)	0.42091 (7)	0.0223 (4)
C6	0.61104 (8)	0.90567 (16)	0.35301 (7)	0.0194 (3)
C7	0.58029 (8)	0.80951 (17)	0.29459 (6)	0.0204 (3)
C8	0.63688 (8)	0.82481 (18)	0.24342 (7)	0.0253 (4)
C9	0.50181 (7)	0.71623 (17)	0.28822 (6)	0.0209 (4)
C10	0.47770 (8)	0.59775 (17)	0.34676 (6)	0.0192 (4)
C11	0.51687 (8)	0.45282 (17)	0.37444 (7)	0.0227 (4)
C12	0.47774 (9)	0.36276 (19)	0.42680 (7)	0.0275 (4)
C13	0.40181 (9)	0.41450 (19)	0.45134 (7)	0.0295 (4)
C14	0.36326 (8)	0.55958 (18)	0.42418 (7)	0.0251 (4)
C15	0.40316 (8)	0.65007 (17)	0.37214 (6)	0.0201 (4)
C16	0.37754 (8)	0.80699 (17)	0.33410 (6)	0.0213 (4)
H1	0.74200	0.95180	0.24110	0.0340*
H2	0.78360	1.12250	0.36210	0.0370*
H3	0.73720	1.16850	0.47330	0.0400*
H4	0.61590	1.04880	0.51040	0.0360*
H5	0.53540	0.88880	0.43600	0.0270*
H8	0.63280	0.77400	0.19980	0.0300*
H9	0.50180	0.64880	0.24510	0.0250*
H11	0.56740	0.41770	0.35840	0.0270*
H12	0.50260	0.26520	0.44620	0.0330*
H13	0.37700	0.35060	0.48630	0.0350*
H14	0.31270	0.59500	0.44010	0.0300*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0225 (5)	0.0239 (5)	0.0233 (5)	0.0029 (4)	−0.0018 (4)	0.0050 (4)
O2	0.0240 (5)	0.0306 (6)	0.0310 (5)	0.0070 (4)	−0.0031 (4)	0.0005 (4)
N1	0.0230 (6)	0.0315 (7)	0.0307 (6)	0.0013 (5)	0.0091 (5)	0.0100 (5)
C1	0.0221 (7)	0.0171 (6)	0.0320 (7)	0.0032 (5)	0.0024 (5)	0.0068 (6)
C2	0.0209 (7)	0.0194 (7)	0.0527 (9)	−0.0016 (6)	−0.0012 (6)	0.0034 (6)
C3	0.0274 (7)	0.0232 (7)	0.0498 (9)	0.0008 (6)	−0.0110 (7)	−0.0100 (7)
C4	0.0304 (7)	0.0278 (8)	0.0309 (7)	0.0055 (6)	−0.0038 (6)	−0.0082 (6)
C5	0.0213 (6)	0.0205 (7)	0.0251 (7)	0.0014 (5)	0.0005 (5)	−0.0005 (5)
C6	0.0195 (6)	0.0148 (6)	0.0238 (6)	0.0025 (5)	−0.0002 (5)	0.0040 (5)
C7	0.0230 (6)	0.0193 (6)	0.0188 (6)	0.0031 (5)	0.0011 (5)	0.0039 (5)
C8	0.0274 (7)	0.0271 (7)	0.0215 (6)	0.0062 (6)	0.0028 (5)	0.0055 (6)
C9	0.0232 (7)	0.0208 (7)	0.0187 (6)	0.0038 (5)	−0.0013 (5)	−0.0005 (5)
C10	0.0222 (6)	0.0186 (7)	0.0168 (6)	−0.0026 (5)	−0.0027 (5)	−0.0035 (5)
C11	0.0231 (7)	0.0220 (7)	0.0230 (7)	0.0025 (5)	−0.0018 (5)	−0.0017 (5)
C12	0.0327 (7)	0.0232 (7)	0.0265 (7)	0.0035 (6)	−0.0027 (6)	0.0047 (6)
C13	0.0335 (8)	0.0301 (8)	0.0248 (7)	−0.0030 (6)	0.0030 (6)	0.0065 (6)
C14	0.0239 (7)	0.0276 (7)	0.0239 (7)	−0.0008 (6)	0.0019 (5)	−0.0015 (6)
C15	0.0222 (6)	0.0195 (7)	0.0185 (6)	−0.0010 (5)	−0.0041 (5)	−0.0034 (5)
C16	0.0210 (6)	0.0232 (7)	0.0196 (6)	−0.0015 (6)	−0.0037 (5)	−0.0029 (5)

Geometric parameters (Å, º) top

O1—C9	1.4882 (15)	C10—C11	1.3901 (19)
O1—C16	1.3533 (15)	C11—C12	1.384 (2)
O2—C16	1.2146 (17)	C12—C13	1.398 (2)
N1—C1	1.3717 (18)	C13—C14	1.382 (2)
N1—C8	1.3642 (18)	C14—C15	1.3875 (19)
N1—H1	0.8600	C15—C16	1.4692 (18)
C1—C2	1.393 (2)	C2—H2	0.9300
C1—C6	1.4159 (19)	C3—H3	0.9300
C2—C3	1.372 (2)	C4—H4	0.9300
C3—C4	1.405 (2)	C5—H5	0.9300
C4—C5	1.380 (2)	C8—H8	0.9300
C5—C6	1.4006 (19)	C9—H9	0.9800
C6—C7	1.4401 (18)	C11—H11	0.9300
C7—C9	1.4849 (18)	C12—H12	0.9300
C7—C8	1.3661 (18)	C13—H13	0.9300
C9—C10	1.5032 (18)	C14—H14	0.9300
C10—C15	1.3847 (19)

C9—O1—C16	110.90 (9)	C10—C15—C16	108.34 (11)
C1—N1—C8	109.14 (11)	C14—C15—C16	129.27 (12)
C8—N1—H1	125.00	C10—C15—C14	122.38 (12)
C1—N1—H1	125.00	O2—C16—C15	129.72 (12)
C2—C1—C6	122.43 (13)	O1—C16—O2	121.61 (11)
N1—C1—C2	129.96 (13)	O1—C16—C15	108.67 (11)
N1—C1—C6	107.59 (11)	C1—C2—H2	121.00
C1—C2—C3	117.38 (13)	C3—C2—H2	121.00
C2—C3—C4	121.48 (14)	C2—C3—H3	119.00
C3—C4—C5	121.16 (14)	C4—C3—H3	119.00
C4—C5—C6	118.86 (12)	C3—C4—H4	119.00
C1—C6—C5	118.68 (12)	C5—C4—H4	119.00
C5—C6—C7	134.76 (12)	C4—C5—H5	121.00
C1—C6—C7	106.52 (11)	C6—C5—H5	121.00
C6—C7—C9	128.19 (11)	N1—C8—H8	125.00
C6—C7—C8	106.42 (12)	C7—C8—H8	125.00
C8—C7—C9	125.36 (11)	O1—C9—H9	109.00
N1—C8—C7	110.33 (12)	C7—C9—H9	109.00
O1—C9—C7	109.81 (10)	C10—C9—H9	109.00
C7—C9—C10	117.28 (10)	C10—C11—H11	121.00
O1—C9—C10	102.85 (9)	C12—C11—H11	121.00
C9—C10—C15	109.17 (11)	C11—C12—H12	119.00
C11—C10—C15	120.52 (12)	C13—C12—H12	119.00
C9—C10—C11	130.28 (12)	C12—C13—H13	120.00
C10—C11—C12	117.41 (12)	C14—C13—H13	120.00
C11—C12—C13	121.76 (13)	C13—C14—H14	121.00
C12—C13—C14	120.76 (13)	C15—C14—H14	121.00
C13—C14—C15	117.15 (12)

C16—O1—C9—C7	−127.15 (10)	C6—C7—C9—O1	69.43 (16)
C16—O1—C9—C10	−1.57 (12)	C6—C7—C9—C10	−47.42 (19)
C9—O1—C16—O2	179.41 (11)	C8—C7—C9—O1	−108.12 (14)
C9—O1—C16—C15	0.14 (13)	C8—C7—C9—C10	135.03 (13)
C8—N1—C1—C2	178.09 (14)	O1—C9—C10—C11	−179.29 (13)
C8—N1—C1—C6	−0.05 (14)	O1—C9—C10—C15	2.50 (13)
C1—N1—C8—C7	0.51 (16)	C7—C9—C10—C11	−58.72 (18)
N1—C1—C2—C3	−177.39 (14)	C7—C9—C10—C15	123.07 (12)
C6—C1—C2—C3	0.5 (2)	C9—C10—C11—C12	−176.83 (13)
N1—C1—C6—C5	177.48 (12)	C15—C10—C11—C12	1.21 (19)
N1—C1—C6—C7	−0.40 (14)	C9—C10—C15—C14	176.57 (12)
C2—C1—C6—C5	−0.8 (2)	C9—C10—C15—C16	−2.51 (14)
C2—C1—C6—C7	−178.71 (12)	C11—C10—C15—C14	−1.9 (2)
C1—C2—C3—C4	0.5 (2)	C11—C10—C15—C16	179.07 (12)
C2—C3—C4—C5	−1.3 (2)	C10—C11—C12—C13	−0.1 (2)
C3—C4—C5—C6	0.9 (2)	C11—C12—C13—C14	−0.5 (2)
C4—C5—C6—C1	0.09 (19)	C12—C13—C14—C15	−0.1 (2)
C4—C5—C6—C7	177.22 (14)	C13—C14—C15—C10	1.2 (2)
C1—C6—C7—C8	0.70 (14)	C13—C14—C15—C16	−179.89 (13)
C1—C6—C7—C9	−177.22 (12)	C10—C15—C16—O1	1.51 (14)
C5—C6—C7—C8	−176.68 (15)	C10—C15—C16—O2	−177.68 (13)
C5—C6—C7—C9	5.4 (2)	C14—C15—C16—O1	−177.49 (13)
C6—C7—C8—N1	−0.75 (15)	C14—C15—C16—O2	3.3 (2)
C9—C7—C8—N1	177.24 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.07	2.8398 (16)	149

Symmetry code: (i) x+1/2, y, −z+1/2.

Acknowledgements

The authors are grateful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, India, for providing the single-crystal X-ray diffractometer facility. RAK thanks UGC for financial assistance from BSR fellowship.

References

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