2-(6-Hy­droxy-1-benzo­furan-3-yl)acetamide

Arunakumar, D.B.; Krishnaswamy, G.; Sreenivasa, S.; Pampa, K.J.; Lokanath, N.K.; Suchetan, P.A.

doi:10.1107/S1600536813033436

organic compounds

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Volume 70| Part 1| January 2014| Page o87

https://doi.org/10.1107/S1600536813033436

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2-(6-Hydroxy-1-benzofuran-3-yl)acetamide

D. B. Arunakumar,^a G. Krishnaswamy,^a S. Sreenivasa,^a K. J. Pampa,^b N. K. Lokanath ^b and P. A. Suchetan ^c ^*

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^bDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, and ^cDepartment of Studies and Research in Chemistry,U.C.S, Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: pasuchetan@yahoo.co.in

(Received 8 December 2013; accepted 10 December 2013; online 24 December 2013)

In the title compound, C₁₀H₉NO₃, the dihedral angle between the benzofuran ring system (r.m.s. deviation for the non-H atoms = 0.009 Å) and the –C—C(O)—N– segment is 83.76 (1)°. In the crystal, molecules are linked by N—H⋯O and O—H⋯O hydrogen bonds, generating (001) sheets, which feature C(4) and C(10) chains.

CCDC reference: 976208

Related literature

For a related structure and background to benzofurans, see: Arunakumar et al. (2014 ).

Experimental

Crystal data

C₁₀H₉NO₃
M_r = 191.18
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.0939 (3) Å
b = 9.3629 (5) Å
c = 18.7422 (10) Å
V = 893.88 (9) Å³
Z = 4
Cu Kα radiation
μ = 0.89 mm⁻¹
T = 293 K
0.36 × 0.29 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.770, T_max = 0.808
8714 measured reflections
1459 independent reflections
1446 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.081
S = 1.14
1459 reflections
136 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 1927 Friedel pairs
Absolute structure parameter: −0.2 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—HO3⋯O1ⁱ	0.82	1.92	2.7006 (16)	158
N1—H1N⋯O3ⁱⁱ	0.92 (3)	2.08 (3)	2.969 (2)	162 (2)
N1—H2N⋯O1ⁱⁱⁱ	0.92 (3)	2.03 (3)	2.8958 (18)	156 (2)
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) x, y-1, z; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); 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: SHELXL97.

Supporting information

CCDC reference: 976208

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536813033436/hb7172sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813033436/hb7172Isup2.hkl

checkCIF report

Comment top

As part of our ongoing structural studies of functionalsied benzofuran ring systems at the C-2 position (Arunakumar et al., 2014), we now describe the structure of the title compound, (I).

In the title compound, C₁₀H₉NO₃, the benzofuran ring is almost planar ((r.m.s. deviation for the non-H atoms = 0.009 Å) (Fig. 1). The dihedral angle between the the two planes defined by the benzofuran ring and the –C—C(O)—N– segment is 96.24 (1)°. Compared to this, the dihedral angle between the benzofuran ring and the –C—C—N—O segment in the related structure (Arunakumar et al., 2014) is 2.85 (1)°. In the crystal structure, the molecules are linked to one another through strong N1—H1N···O3 and N1—H2N···O1 hydrogen bonds generating C(4) and C(10) chains (Fig. 2). The molecules are further connected into C(10) chains through strong O3—HO3···O1 hydrogen bonds forming helical structure (Fig. 3). Linking of molecules in zig zag pattern through N1—H1N···O3 H-bonds is shown in Fig. 4.

Related literature top

For a related structure and background to benzofurans, see: Arunakumar et al. (2014).

Experimental top

(6-Hydroxy-1-benzofuran-3-yl)acetic acid (0.015 mmol) was taken in a round bottom flask containing N,N-dimethyl formamide (15 ml)·To this 1, 1-carbonydiimadazole (0.023 mmol) was added at 273 K. The reaction mixture was stirred for 45 minutes. Ammonium acetate (0.046 mmol) and triethyl amine (1 ml) were added, the reaction mixture was stirred at room temperature overnight. The completion of the reaction was monitored by thin layer chromatography. After completion of the reaction, the reaction mixture was diluted with ethylacetate and the organic layer was washed with water followed by brine solution. The organic layer was dried over anhydrous sodium sulfate and concentrated to give the crude product. It was further purified by column chromatography by using Ethyl acetate and petroleum ether (8:2) as eluent.

Colourless prisms were obtained from the solvent system: ethyl acetate / methanol (4:1) at room temperature.

Structure description top

As part of our ongoing structural studies of functionalsied benzofuran ring systems at the C-2 position (Arunakumar et al., 2014), we now describe the structure of the title compound, (I).

For a related structure and background to benzofurans, see: Arunakumar et al. (2014).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Linking of molecules in the crystal structure through N—H···O hydrogen bonds into C(4) and C(10) chains. H-atoms not involved in H-bonding are omitted for clarity.
	Fig. 3. Formation of helical structure through O—H···O hydrogen bonds.
	Fig. 4. Zig-zag pattern observed in the crystal structure.

2-(6-Hydroxy-1-benzofuran-3-yl)acetamide top

Crystal data top

C₁₀H₉NO₃	Prism
M_r = 191.18	D_x = 1.421 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Melting point: 533 K
Hall symbol: P 2ac 2ab	Cu Kα radiation, λ = 1.54178 Å
a = 5.0939 (3) Å	Cell parameters from 1234 reflections
b = 9.3629 (5) Å	θ = 4.7–64.3°
c = 18.7422 (10) Å	µ = 0.89 mm⁻¹
V = 893.88 (9) Å³	T = 293 K
Z = 4	Prism, colourless
F(000) = 400	0.36 × 0.29 × 0.24 mm

Data collection top

Bruker APEXII CCD diffractometer	1459 independent reflections
Radiation source: fine-focus sealed tube	1446 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
φ and ω scans	θ_max = 64.3°, θ_min = 4.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
T_min = 0.770, T_max = 0.808	k = −10→10
8714 measured reflections	l = −21→21

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.081	w = 1/[σ²(F_o²) + (0.0488P)² + 0.1043P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max < 0.001
1459 reflections	Δρ_max = 0.15 e Å⁻³
136 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1927 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.2 (2)

Crystal data top

C₁₀H₉NO₃	V = 893.88 (9) Å³
M_r = 191.18	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 5.0939 (3) Å	µ = 0.89 mm⁻¹
b = 9.3629 (5) Å	T = 293 K
c = 18.7422 (10) Å	0.36 × 0.29 × 0.24 mm

Data collection top

Bruker APEXII CCD diffractometer	1459 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1446 reflections with I > 2σ(I)
T_min = 0.770, T_max = 0.808	R_int = 0.036
8714 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.081	Δρ_max = 0.15 e Å⁻³
S = 1.14	Δρ_min = −0.28 e Å⁻³
1459 reflections	Absolute structure: Flack (1983), 1927 Friedel pairs
136 parameters	Absolute structure parameter: −0.2 (2)
0 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

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

	x	y	z	U_iso*/U_eq
H2N	0.766 (5)	0.410 (3)	0.6264 (14)	0.072 (7)*
H1N	0.587 (5)	0.324 (3)	0.5742 (14)	0.069 (7)*
C1	0.4600 (3)	1.02627 (16)	0.55047 (8)	0.0361 (4)
C2	0.6218 (3)	0.90706 (18)	0.54019 (9)	0.0404 (4)
H2	0.7494	0.9092	0.5047	0.049*
C3	0.5949 (3)	0.78677 (18)	0.58188 (8)	0.0402 (4)
H3	0.7026	0.7079	0.5747	0.048*
C4	0.4029 (3)	0.78533 (16)	0.63518 (7)	0.0334 (3)
C5	0.2448 (3)	0.90548 (17)	0.64295 (8)	0.0369 (4)
C6	0.2657 (3)	1.02782 (17)	0.60204 (9)	0.0398 (4)
H6	0.1562	1.1061	0.6088	0.048*
C7	0.1208 (4)	0.75102 (19)	0.72418 (8)	0.0452 (4)
H7	0.0293	0.7101	0.7619	0.054*
C8	0.3173 (3)	0.68572 (17)	0.68946 (8)	0.0370 (4)
C9	0.4300 (3)	0.54149 (18)	0.70437 (8)	0.0406 (4)
H9A	0.3482	0.5023	0.7468	0.049*
H9B	0.6166	0.5506	0.7136	0.049*
C10	0.3882 (3)	0.44027 (15)	0.64264 (8)	0.0331 (3)
N1	0.5982 (3)	0.38614 (19)	0.61193 (9)	0.0492 (4)
O1	0.1637 (2)	0.41077 (13)	0.62188 (6)	0.0433 (3)
O2	0.0692 (2)	0.88620 (13)	0.69762 (6)	0.0473 (3)
O3	0.4914 (2)	1.14862 (11)	0.51112 (6)	0.0454 (3)
HO3	0.5821	1.1314	0.4760	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0386 (8)	0.0371 (8)	0.0326 (7)	−0.0049 (6)	−0.0004 (6)	−0.0042 (6)
C2	0.0363 (9)	0.0486 (9)	0.0364 (7)	−0.0001 (7)	0.0078 (7)	−0.0003 (6)
C3	0.0371 (9)	0.0440 (8)	0.0396 (8)	0.0048 (7)	0.0066 (7)	−0.0023 (6)
C4	0.0306 (8)	0.0402 (8)	0.0294 (7)	−0.0038 (6)	0.0006 (6)	−0.0059 (6)
C5	0.0334 (8)	0.0444 (8)	0.0328 (7)	−0.0052 (7)	0.0050 (6)	−0.0093 (6)
C6	0.0381 (9)	0.0395 (8)	0.0417 (8)	0.0015 (7)	0.0042 (7)	−0.0081 (7)
C7	0.0499 (10)	0.0505 (9)	0.0353 (8)	−0.0090 (8)	0.0103 (7)	−0.0037 (7)
C8	0.0375 (9)	0.0449 (8)	0.0287 (7)	−0.0085 (7)	0.0000 (7)	−0.0056 (6)
C9	0.0411 (9)	0.0495 (9)	0.0312 (7)	−0.0058 (7)	−0.0054 (7)	0.0026 (6)
C10	0.0296 (8)	0.0377 (7)	0.0320 (7)	−0.0027 (6)	−0.0021 (6)	0.0070 (6)
N1	0.0320 (8)	0.0597 (9)	0.0559 (9)	−0.0004 (7)	0.0012 (7)	−0.0097 (8)
O1	0.0290 (6)	0.0567 (7)	0.0444 (6)	−0.0025 (5)	−0.0029 (5)	−0.0082 (5)
O2	0.0476 (7)	0.0508 (7)	0.0434 (6)	−0.0008 (6)	0.0187 (5)	−0.0079 (5)
O3	0.0537 (8)	0.0405 (6)	0.0419 (6)	−0.0003 (5)	0.0081 (5)	0.0008 (5)

Geometric parameters (Å, º) top

C1—O3	1.3717 (19)	C7—C8	1.341 (2)
C1—C6	1.383 (2)	C7—O2	1.385 (2)
C1—C2	1.401 (2)	C7—H7	0.9300
C2—C3	1.378 (2)	C8—C9	1.494 (2)
C2—H2	0.9300	C9—C10	1.511 (2)
C3—C4	1.398 (2)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.391 (2)	C10—O1	1.2390 (19)
C4—C8	1.447 (2)	C10—N1	1.317 (2)
C5—O2	1.372 (2)	N1—H2N	0.92 (3)
C5—C6	1.382 (2)	N1—H1N	0.92 (3)
C6—H6	0.9300	O3—HO3	0.8200

O3—C1—C6	116.76 (14)	C8—C7—H7	123.7
O3—C1—C2	121.52 (14)	O2—C7—H7	123.7
C6—C1—C2	121.69 (15)	C7—C8—C4	105.80 (15)
C3—C2—C1	120.98 (14)	C7—C8—C9	127.46 (16)
C3—C2—H2	119.5	C4—C8—C9	126.73 (15)
C1—C2—H2	119.5	C8—C9—C10	111.69 (12)
C2—C3—C4	118.87 (15)	C8—C9—H9A	109.3
C2—C3—H3	120.6	C10—C9—H9A	109.3
C4—C3—H3	120.6	C8—C9—H9B	109.3
C5—C4—C3	118.16 (14)	C10—C9—H9B	109.3
C5—C4—C8	105.84 (13)	H9A—C9—H9B	107.9
C3—C4—C8	136.00 (15)	O1—C10—N1	121.80 (15)
O2—C5—C6	124.99 (15)	O1—C10—C9	120.70 (14)
O2—C5—C4	110.44 (14)	N1—C10—C9	117.50 (15)
C6—C5—C4	124.56 (14)	C10—N1—H2N	121.9 (16)
C5—C6—C1	115.73 (15)	C10—N1—H1N	122.0 (17)
C5—C6—H6	122.1	H2N—N1—H1N	116 (2)
C1—C6—H6	122.1	C5—O2—C7	105.37 (13)
C8—C7—O2	112.56 (14)	C1—O3—HO3	109.5

O3—C1—C2—C3	177.50 (15)	O2—C7—C8—C4	−0.22 (19)
C6—C1—C2—C3	−0.7 (3)	O2—C7—C8—C9	178.51 (14)
C1—C2—C3—C4	−0.2 (2)	C5—C4—C8—C7	0.25 (17)
C2—C3—C4—C5	0.9 (2)	C3—C4—C8—C7	179.59 (18)
C2—C3—C4—C8	−178.39 (17)	C5—C4—C8—C9	−178.49 (14)
C3—C4—C5—O2	−179.68 (13)	C3—C4—C8—C9	0.8 (3)
C8—C4—C5—O2	−0.21 (17)	C7—C8—C9—C10	116.36 (19)
C3—C4—C5—C6	−0.8 (2)	C4—C8—C9—C10	−65.2 (2)
C8—C4—C5—C6	178.69 (15)	C8—C9—C10—O1	−59.9 (2)
O2—C5—C6—C1	178.69 (15)	C8—C9—C10—N1	119.67 (16)
C4—C5—C6—C1	−0.1 (2)	C6—C5—O2—C7	−178.81 (16)
O3—C1—C6—C5	−177.48 (14)	C4—C5—O2—C7	0.08 (17)
C2—C1—C6—C5	0.8 (2)	C8—C7—O2—C5	0.09 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—HO3···O1ⁱ	0.82	1.92	2.7006 (16)	158
N1—H1N···O3ⁱⁱ	0.92 (3)	2.08 (3)	2.969 (2)	162 (2)
N1—H2N···O1ⁱⁱⁱ	0.92 (3)	2.03 (3)	2.8958 (18)	156 (2)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x, y−1, z; (iii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—HO3···O1ⁱ	0.82	1.92	2.7006 (16)	158
N1—H1N···O3ⁱⁱ	0.92 (3)	2.08 (3)	2.969 (2)	162 (2)
N1—H2N···O1ⁱⁱⁱ	0.92 (3)	2.03 (3)	2.8958 (18)	156 (2)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) x, y−1, z; (iii) x+1, y, z.

Acknowledgements

The authors acknowledge the IOE X-ray diffractometer Facility, University of Mysore, Mysore, for the data collection.

References

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