N-Hydr-oxy-N-o-tolyl-acetamide.

In the mol-ecule of the title compound, C(9)H(11)NO(2), the methyl C atom bonded to the ring and the N atom lie in the benzene ring plane. An intra-molecular O-H⋯O hydrogen bond results in the formation of a five-membered planar ring, which is oriented at a dihedral angle of 81.37 (3)° with respect to the benzene ring. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules stacked along the b axis. There are also π-π inter-actions between benzene rings with a face-to-face stacking distance of 3.434 Å.

Related literature

For related literature, see: Fu et al. (2000 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H11NO2

M = 165.19

Monoclinic,

a = 7.7890 (16) Å

b = 7.1570 (14) Å

c = 15.613 (3) Å

β = 96.86 (3)°

V = 864.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 294 (2) K

0.40 × 0.30 × 0.30 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.965, T max = 0.973

1821 measured reflections

1695 independent reflections

1187 reflections with I > 2σ(I)

R int = 0.054

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.182

S = 1.05

1695 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002468/hk2420sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002468/hk2420Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H11NO2	F000 = 352
Mr = 165.19	Dx = 1.270 Mg m−3
Monoclinic, P21/c	Melting point: 350 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 7.7890 (16) Å	Cell parameters from 25 reflections
b = 7.1570 (14) Å	θ = 10–13º
c = 15.613 (3) Å	µ = 0.09 mm−1
β = 96.86 (3)º	T = 294 (2) K
V = 864.1 (3) Å3	Block, colorless
Z = 4	0.40 × 0.30 × 0.30 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.054
Radiation source: fine-focus sealed tube	θmax = 26.0º
Monochromator: graphite	θmin = 2.6º
T = 294(2) K	h = −9→9
ω/2θ scans	k = 0→8
Absorption correction: ψ scan(North et al., 1968)	l = 0→19
Tmin = 0.965, Tmax = 0.973	3 standard reflections
1821 measured reflections	every 120 min
1695 independent reflections	intensity decay: none
1187 reflections with I > 2σ(I)

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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.182	w = 1/[σ2(Fo2) + (0.05P)2 + 1.5P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1695 reflections	Δρmax = 0.31 e Å−3
109 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

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 > σ(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
N	0.7518 (4)	0.1297 (4)	0.08788 (17)	0.0451 (7)
O1	0.8117 (3)	−0.0536 (3)	0.08895 (15)	0.0554 (7)
H1A	0.8888	−0.0624	0.0577	0.083*
O2	0.9365 (3)	0.2046 (3)	−0.00399 (16)	0.0573 (7)
C1	0.8476 (4)	0.1834 (6)	0.2703 (2)	0.0593 (10)
H1B	0.8527	0.2003	0.3316	0.089*
H1C	0.9065	0.2848	0.2461	0.089*
H1D	0.9022	0.0675	0.2585	0.089*
C2	0.6626 (4)	0.1799 (4)	0.23108 (19)	0.0406 (7)
C3	0.5278 (5)	0.2025 (5)	0.2806 (2)	0.0508 (9)
H3A	0.5533	0.2200	0.3398	0.061*
C4	0.3579 (5)	0.1999 (5)	0.2453 (2)	0.0536 (9)
H4A	0.2706	0.2150	0.2805	0.064*
C5	0.3164 (4)	0.1750 (5)	0.1577 (2)	0.0572 (9)
H5A	0.2013	0.1721	0.1337	0.069*
C6	0.4465 (4)	0.1545 (5)	0.1062 (2)	0.0454 (8)
H6A	0.4194	0.1392	0.0470	0.054*
C7	0.6189 (4)	0.1567 (4)	0.14250 (18)	0.0370 (7)
C8	0.8214 (4)	0.2543 (5)	0.03929 (18)	0.0411 (7)
C9	0.7578 (5)	0.4524 (5)	0.0400 (3)	0.0586 (10)
H9A	0.8186	0.5270	0.0023	0.088*
H9B	0.7779	0.5013	0.0975	0.088*
H9C	0.6362	0.4555	0.0205	0.088*

	U11	U22	U33	U12	U13	U23
N	0.0584 (17)	0.0377 (14)	0.0420 (14)	0.0072 (12)	0.0179 (12)	0.0028 (12)
O1	0.0735 (16)	0.0420 (13)	0.0570 (15)	0.0174 (11)	0.0338 (12)	0.0085 (11)
O2	0.0654 (15)	0.0530 (15)	0.0599 (15)	0.0118 (12)	0.0343 (13)	0.0102 (12)
C1	0.054 (2)	0.066 (2)	0.057 (2)	−0.0089 (18)	0.0002 (16)	−0.0039 (18)
C2	0.0504 (18)	0.0360 (16)	0.0352 (16)	0.0026 (14)	0.0045 (13)	−0.0034 (12)
C3	0.073 (2)	0.0481 (19)	0.0339 (16)	0.0030 (17)	0.0155 (15)	−0.0029 (14)
C4	0.057 (2)	0.050 (2)	0.059 (2)	0.0045 (16)	0.0285 (17)	0.0015 (17)
C5	0.0411 (18)	0.064 (2)	0.066 (2)	0.0057 (17)	0.0044 (16)	−0.0010 (19)
C6	0.0486 (18)	0.0471 (19)	0.0401 (17)	0.0052 (15)	0.0043 (14)	0.0001 (14)
C7	0.0423 (16)	0.0363 (16)	0.0349 (15)	0.0036 (13)	0.0150 (12)	0.0012 (12)
C8	0.0440 (16)	0.0482 (18)	0.0318 (15)	0.0009 (14)	0.0076 (12)	0.0017 (13)
C9	0.069 (2)	0.044 (2)	0.066 (2)	0.0046 (17)	0.0243 (19)	0.0052 (17)

N—C8	1.328 (4)	C3—H3A	0.9300
N—O1	1.392 (3)	C4—C5	1.378 (5)
N—C7	1.431 (4)	C4—H4A	0.9300
O1—H1A	0.8200	C5—C6	1.375 (5)
C1—C2	1.497 (5)	C5—H5A	0.9300
C1—H1B	0.9600	C6—C7	1.394 (4)
C1—H1C	0.9600	C6—H6A	0.9300
C1—H1D	0.9600	C8—C9	1.502 (5)
O2—C8	1.238 (3)	C9—H9A	0.9600
C2—C3	1.386 (4)	C9—H9B	0.9600
C2—C7	1.394 (4)	C9—H9C	0.9600
C3—C4	1.371 (5)
C8—N—O1	118.8 (2)	C6—C5—C4	119.5 (3)
C8—N—C7	128.6 (3)	C6—C5—H5A	120.3
O1—N—C7	112.7 (2)	C4—C5—H5A	120.3
N—O1—H1A	109.5	C5—C6—C7	120.2 (3)
C2—C1—H1B	109.5	C5—C6—H6A	119.9
C2—C1—H1C	109.5	C7—C6—H6A	119.9
H1B—C1—H1C	109.5	C6—C7—C2	120.9 (3)
C2—C1—H1D	109.5	C6—C7—N	119.1 (3)
H1B—C1—H1D	109.5	C2—C7—N	119.9 (3)
H1C—C1—H1D	109.5	O2—C8—N	119.4 (3)
C3—C2—C7	117.1 (3)	O2—C8—C9	122.4 (3)
C3—C2—C1	121.7 (3)	N—C8—C9	118.2 (3)
C7—C2—C1	121.1 (3)	C8—C9—H9A	109.5
C4—C3—C2	122.2 (3)	C8—C9—H9B	109.5
C4—C3—H3A	118.9	H9A—C9—H9B	109.5
C2—C3—H3A	118.9	C8—C9—H9C	109.5
C3—C4—C5	120.1 (3)	H9A—C9—H9C	109.5
C3—C4—H4A	119.9	H9B—C9—H9C	109.5
C5—C4—H4A	119.9
C7—C2—C3—C4	0.9 (5)	C1—C2—C7—N	2.0 (4)
C1—C2—C3—C4	179.9 (3)	C8—N—C7—C6	82.5 (4)
C2—C3—C4—C5	−0.3 (5)	O1—N—C7—C6	−98.0 (3)
C3—C4—C5—C6	−0.6 (6)	C8—N—C7—C2	−99.2 (4)
C4—C5—C6—C7	0.8 (5)	O1—N—C7—C2	80.4 (3)
C5—C6—C7—C2	−0.1 (5)	O1—N—C8—O2	0.4 (5)
C5—C6—C7—N	178.2 (3)	C7—N—C8—O2	179.9 (3)
C3—C2—C7—C6	−0.7 (4)	O1—N—C8—C9	−178.9 (3)
C1—C2—C7—C6	−179.7 (3)	C7—N—C8—C9	0.6 (5)
C3—C2—C7—N	−179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	2.19	2.608 (3)	112
O1—H1A···O2i	0.82	1.97	2.719 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.82	2.19	2.608 (3)	112
O1—H1A⋯O2i	0.82	1.97	2.719 (3)	152

Symmetry code: (i) .