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

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ISSN: 2056-9890

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

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.

Related literature

For a related structure and background to benzo­furans, see: Arunakumar et al. (2014[Arunakumar, D. B., Nivedita, R. D., Sreenivasa, S., Madan Kumar, S., Lokanath, N. K. & Suchetan, P. A. (2014). Acta Cryst. E70, o40.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9NO3

  • Mr = 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[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.770, Tmax = 0.808

  • 8714 measured reflections

  • 1459 independent reflections

  • 1446 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.28 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1927 Friedel pairs

  • Absolute structure parameter: −0.2 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: 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.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

The H atoms were positioned with idealized geometry using a riding model with C—H = 0.93–0.97 Å and O—H = 0.82 Å. The H atoms of the NH2 group were located in a difference map and later refined freely. The isotropic displacement parameters for all H atoms were set to 1.2 times Ueq (Carbon) and 1.5 times Ueq (Oxygen)..

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
[Figure 1] Fig. 1. Molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
[Figure 2] 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.
[Figure 3] Fig. 3. Formation of helical structure through O—H···O hydrogen bonds.
[Figure 4] Fig. 4. Zig-zag pattern observed in the crystal structure.
2-(6-Hydroxy-1-benzofuran-3-yl)acetamide top
Crystal data top
C10H9NO3Prism
Mr = 191.18Dx = 1.421 Mg m3
Orthorhombic, P212121Melting point: 533 K
Hall symbol: P 2ac 2abCu Kα radiation, λ = 1.54178 Å
a = 5.0939 (3) ÅCell parameters from 1234 reflections
b = 9.3629 (5) Åθ = 4.7–64.3°
c = 18.7422 (10) ŵ = 0.89 mm1
V = 893.88 (9) Å3T = 293 K
Z = 4Prism, colourless
F(000) = 4000.36 × 0.29 × 0.24 mm
Data collection top
Bruker APEXII CCD
diffractometer
1459 independent reflections
Radiation source: fine-focus sealed tube1446 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ϕ and ω scansθmax = 64.3°, θmin = 4.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 55
Tmin = 0.770, Tmax = 0.808k = 1010
8714 measured reflectionsl = 2121
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0488P)2 + 0.1043P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max < 0.001
1459 reflectionsΔρmax = 0.15 e Å3
136 parametersΔρmin = 0.28 e Å3
0 restraintsAbsolute structure: Flack (1983), 1927 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.2 (2)
Crystal data top
C10H9NO3V = 893.88 (9) Å3
Mr = 191.18Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 5.0939 (3) ŵ = 0.89 mm1
b = 9.3629 (5) ÅT = 293 K
c = 18.7422 (10) Å0.36 × 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)
Tmin = 0.770, Tmax = 0.808Rint = 0.036
8714 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081Δρmax = 0.15 e Å3
S = 1.14Δρmin = 0.28 e Å3
1459 reflectionsAbsolute structure: Flack (1983), 1927 Friedel pairs
136 parametersAbsolute 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
xyzUiso*/Ueq
H2N0.766 (5)0.410 (3)0.6264 (14)0.072 (7)*
H1N0.587 (5)0.324 (3)0.5742 (14)0.069 (7)*
C10.4600 (3)1.02627 (16)0.55047 (8)0.0361 (4)
C20.6218 (3)0.90706 (18)0.54019 (9)0.0404 (4)
H20.74940.90920.50470.049*
C30.5949 (3)0.78677 (18)0.58188 (8)0.0402 (4)
H30.70260.70790.57470.048*
C40.4029 (3)0.78533 (16)0.63518 (7)0.0334 (3)
C50.2448 (3)0.90548 (17)0.64295 (8)0.0369 (4)
C60.2657 (3)1.02782 (17)0.60204 (9)0.0398 (4)
H60.15621.10610.60880.048*
C70.1208 (4)0.75102 (19)0.72418 (8)0.0452 (4)
H70.02930.71010.76190.054*
C80.3173 (3)0.68572 (17)0.68946 (8)0.0370 (4)
C90.4300 (3)0.54149 (18)0.70437 (8)0.0406 (4)
H9A0.34820.50230.74680.049*
H9B0.61660.55060.71360.049*
C100.3882 (3)0.44027 (15)0.64264 (8)0.0331 (3)
N10.5982 (3)0.38614 (19)0.61193 (9)0.0492 (4)
O10.1637 (2)0.41077 (13)0.62188 (6)0.0433 (3)
O20.0692 (2)0.88620 (13)0.69762 (6)0.0473 (3)
O30.4914 (2)1.14862 (11)0.51112 (6)0.0454 (3)
HO30.58211.13140.47600.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0386 (8)0.0371 (8)0.0326 (7)0.0049 (6)0.0004 (6)0.0042 (6)
C20.0363 (9)0.0486 (9)0.0364 (7)0.0001 (7)0.0078 (7)0.0003 (6)
C30.0371 (9)0.0440 (8)0.0396 (8)0.0048 (7)0.0066 (7)0.0023 (6)
C40.0306 (8)0.0402 (8)0.0294 (7)0.0038 (6)0.0006 (6)0.0059 (6)
C50.0334 (8)0.0444 (8)0.0328 (7)0.0052 (7)0.0050 (6)0.0093 (6)
C60.0381 (9)0.0395 (8)0.0417 (8)0.0015 (7)0.0042 (7)0.0081 (7)
C70.0499 (10)0.0505 (9)0.0353 (8)0.0090 (8)0.0103 (7)0.0037 (7)
C80.0375 (9)0.0449 (8)0.0287 (7)0.0085 (7)0.0000 (7)0.0056 (6)
C90.0411 (9)0.0495 (9)0.0312 (7)0.0058 (7)0.0054 (7)0.0026 (6)
C100.0296 (8)0.0377 (7)0.0320 (7)0.0027 (6)0.0021 (6)0.0070 (6)
N10.0320 (8)0.0597 (9)0.0559 (9)0.0004 (7)0.0012 (7)0.0097 (8)
O10.0290 (6)0.0567 (7)0.0444 (6)0.0025 (5)0.0029 (5)0.0082 (5)
O20.0476 (7)0.0508 (7)0.0434 (6)0.0008 (6)0.0187 (5)0.0079 (5)
O30.0537 (8)0.0405 (6)0.0419 (6)0.0003 (5)0.0081 (5)0.0008 (5)
Geometric parameters (Å, º) top
C1—O31.3717 (19)C7—C81.341 (2)
C1—C61.383 (2)C7—O21.385 (2)
C1—C21.401 (2)C7—H70.9300
C2—C31.378 (2)C8—C91.494 (2)
C2—H20.9300C9—C101.511 (2)
C3—C41.398 (2)C9—H9A0.9700
C3—H30.9300C9—H9B0.9700
C4—C51.391 (2)C10—O11.2390 (19)
C4—C81.447 (2)C10—N11.317 (2)
C5—O21.372 (2)N1—H2N0.92 (3)
C5—C61.382 (2)N1—H1N0.92 (3)
C6—H60.9300O3—HO30.8200
O3—C1—C6116.76 (14)C8—C7—H7123.7
O3—C1—C2121.52 (14)O2—C7—H7123.7
C6—C1—C2121.69 (15)C7—C8—C4105.80 (15)
C3—C2—C1120.98 (14)C7—C8—C9127.46 (16)
C3—C2—H2119.5C4—C8—C9126.73 (15)
C1—C2—H2119.5C8—C9—C10111.69 (12)
C2—C3—C4118.87 (15)C8—C9—H9A109.3
C2—C3—H3120.6C10—C9—H9A109.3
C4—C3—H3120.6C8—C9—H9B109.3
C5—C4—C3118.16 (14)C10—C9—H9B109.3
C5—C4—C8105.84 (13)H9A—C9—H9B107.9
C3—C4—C8136.00 (15)O1—C10—N1121.80 (15)
O2—C5—C6124.99 (15)O1—C10—C9120.70 (14)
O2—C5—C4110.44 (14)N1—C10—C9117.50 (15)
C6—C5—C4124.56 (14)C10—N1—H2N121.9 (16)
C5—C6—C1115.73 (15)C10—N1—H1N122.0 (17)
C5—C6—H6122.1H2N—N1—H1N116 (2)
C1—C6—H6122.1C5—O2—C7105.37 (13)
C8—C7—O2112.56 (14)C1—O3—HO3109.5
O3—C1—C2—C3177.50 (15)O2—C7—C8—C40.22 (19)
C6—C1—C2—C30.7 (3)O2—C7—C8—C9178.51 (14)
C1—C2—C3—C40.2 (2)C5—C4—C8—C70.25 (17)
C2—C3—C4—C50.9 (2)C3—C4—C8—C7179.59 (18)
C2—C3—C4—C8178.39 (17)C5—C4—C8—C9178.49 (14)
C3—C4—C5—O2179.68 (13)C3—C4—C8—C90.8 (3)
C8—C4—C5—O20.21 (17)C7—C8—C9—C10116.36 (19)
C3—C4—C5—C60.8 (2)C4—C8—C9—C1065.2 (2)
C8—C4—C5—C6178.69 (15)C8—C9—C10—O159.9 (2)
O2—C5—C6—C1178.69 (15)C8—C9—C10—N1119.67 (16)
C4—C5—C6—C10.1 (2)C6—C5—O2—C7178.81 (16)
O3—C1—C6—C5177.48 (14)C4—C5—O2—C70.08 (17)
C2—C1—C6—C50.8 (2)C8—C7—O2—C50.09 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—HO3···O1i0.821.922.7006 (16)158
N1—H1N···O3ii0.92 (3)2.08 (3)2.969 (2)162 (2)
N1—H2N···O1iii0.92 (3)2.03 (3)2.8958 (18)156 (2)
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x, y1, z; (iii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—HO3···O1i0.821.922.7006 (16)158
N1—H1N···O3ii0.92 (3)2.08 (3)2.969 (2)162 (2)
N1—H2N···O1iii0.92 (3)2.03 (3)2.8958 (18)156 (2)
Symmetry codes: (i) x+1/2, y+3/2, z+1; (ii) x, y1, 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

First citationArunakumar, D. B., Nivedita, R. D., Sreenivasa, S., Madan Kumar, S., Lokanath, N. K. & Suchetan, P. A. (2014). Acta Cryst. E70, o40.  CSD CrossRef IUCr Journals
First citationBruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationMacrae, 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.  Web of Science CrossRef CAS IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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