2-(6-Hy-droxy-1-benzo-furan-3-yl)acetamide.

In the title compound, C10H9NO3, the dihedral angle between the benzo-furan 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, mol-ecules 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 ▶).

Experimental

Crystal data

C10H9NO3

M = 191.18

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 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 ▶), 1927 Friedel pairs

Absolute structure parameter: −0.2 (2)

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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813033436/hb7172sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033436/hb7172Isup2.hkl

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H9NO3	Prism
Mr = 191.18	Dx = 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

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

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(Fo2) + (0.0488P)2 + 0.1043P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
1459 reflections	Δρmax = 0.15 e Å−3
136 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) ; (iii) .