3-Hy-droxy-2-meth-oxy-benzamide.

The crystal structure of the title compound, C8H9NO3, features centrosymmetric dimers with two amide groups inter-connected by a pair of almost linear N-H⋯O hydrogen bonds. Through inter-molecular O-H⋯O inter-actions between phenolic hy-droxy groups and carbonyl O atoms, these dimers are assembled into undulating hydrogen-bonded layers parallel to the [101] plane. Additionally, the anti-H(-N) atom of the primary amide group forms an intra-molecular hydrogen bond to the O atom of the meth-oxy group. The amide group froms a dihedral angle of 12.6 (1)° with the phenyl ring.

Related literature

Hydrogen-bonding packing patterns of primary amides are discussed by Eccles et al. (2011 ▶) and McMahon et al. (2005 ▶). A description of the Cambridge Crystallographic Database is given by Allen (2002 ▶). The question of the occurrence of very bent, intra­molecular C—H⋯O hydrogen bonds has been discussed by Desiraju (1996 ▶).

Experimental

Crystal data

C8H9NO3

M = 167.16

Monoclinic,

a = 5.6293 (2) Å

b = 10.1826 (4) Å

c = 13.2402 (5) Å

β = 92.750 (1)°

V = 758.07 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 110 K

0.49 × 0.18 × 0.14 mm

Data collection

Bruker APEXII KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2010 ▶) T min = 0.947, T max = 0.984

7200 measured reflections

1484 independent reflections

1325 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.06

1484 reflections

122 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812047769/ld2083sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047769/ld2083Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047769/ld2083Isup3.cml

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

C8H9NO3	F(000) = 352
Mr = 167.16	Dx = 1.465 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.6293 (2) Å	Cell parameters from 3853 reflections
b = 10.1826 (4) Å	θ = 2.5–32.5°
c = 13.2402 (5) Å	µ = 0.11 mm−1
β = 92.750 (1)°	T = 110 K
V = 758.07 (5) Å3	Prism, colourless
Z = 4	0.49 × 0.18 × 0.14 mm

Bruker APEXII KappaCCD diffractometer	1484 independent reflections
Radiation source: fine-focus sealed tube	1325 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
phi and ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −6→6
Tmin = 0.947, Tmax = 0.984	k = −12→12
7200 measured reflections	l = −15→16

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0421P)2 + 0.2806P] where P = (Fo2 + 2Fc2)/3
1484 reflections	(Δ/σ)max = 0.001
122 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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
O1	0.17410 (14)	0.98464 (8)	0.80141 (6)	0.0160 (2)
O2	−0.12850 (15)	0.83936 (9)	0.91393 (6)	0.0192 (2)
H2	−0.195 (3)	0.7717 (19)	0.9432 (13)	0.046 (5)*
O3	0.23900 (15)	0.88839 (8)	0.49736 (6)	0.0194 (2)
N1	0.35604 (19)	1.02761 (11)	0.62107 (8)	0.0207 (3)
H1A	0.474 (3)	1.0570 (15)	0.5835 (12)	0.031 (4)*
H1B	0.346 (3)	1.0515 (16)	0.6851 (13)	0.031 (4)*
C1	0.0386 (2)	0.87000 (11)	0.65116 (9)	0.0149 (3)
C2	0.03195 (19)	0.88969 (11)	0.75592 (8)	0.0137 (3)
C3	−0.1284 (2)	0.81706 (11)	0.81214 (9)	0.0156 (3)
C4	−0.2821 (2)	0.72817 (12)	0.76327 (9)	0.0182 (3)
H4	−0.3876	0.6775	0.8014	0.022*
C5	−0.2824 (2)	0.71313 (12)	0.65908 (9)	0.0203 (3)
H5	−0.3918	0.6546	0.6258	0.024*
C6	−0.1234 (2)	0.78327 (12)	0.60378 (9)	0.0185 (3)
H6	−0.1243	0.7723	0.5325	0.022*
C7	0.2192 (2)	0.93056 (11)	0.58521 (9)	0.0158 (3)
C8	0.3210 (2)	0.94758 (13)	0.88935 (9)	0.0213 (3)
H8A	0.2392	0.9700	0.9507	0.032*
H8B	0.4727	0.9948	0.8890	0.032*
H8C	0.3508	0.8528	0.8879	0.032*

	U11	U22	U33	U12	U13	U23
O1	0.0186 (4)	0.0168 (4)	0.0125 (4)	−0.0020 (3)	−0.0006 (3)	−0.0004 (3)
O2	0.0235 (5)	0.0217 (5)	0.0125 (4)	−0.0022 (4)	0.0045 (3)	0.0010 (3)
O3	0.0241 (5)	0.0209 (5)	0.0138 (4)	−0.0026 (3)	0.0063 (3)	−0.0024 (3)
N1	0.0247 (6)	0.0232 (6)	0.0150 (5)	−0.0082 (4)	0.0083 (4)	−0.0027 (4)
C1	0.0167 (6)	0.0138 (6)	0.0146 (6)	0.0017 (4)	0.0033 (4)	0.0007 (4)
C2	0.0137 (5)	0.0121 (5)	0.0152 (6)	0.0019 (4)	0.0002 (4)	−0.0008 (4)
C3	0.0183 (6)	0.0160 (6)	0.0126 (5)	0.0036 (5)	0.0026 (4)	0.0010 (4)
C4	0.0185 (6)	0.0172 (6)	0.0193 (6)	−0.0015 (5)	0.0053 (5)	0.0025 (5)
C5	0.0213 (6)	0.0185 (6)	0.0210 (6)	−0.0052 (5)	0.0012 (5)	−0.0022 (5)
C6	0.0231 (6)	0.0196 (6)	0.0128 (6)	−0.0014 (5)	0.0021 (5)	−0.0018 (5)
C7	0.0180 (6)	0.0156 (6)	0.0138 (6)	0.0018 (4)	0.0024 (4)	0.0010 (5)
C8	0.0192 (6)	0.0277 (7)	0.0165 (6)	−0.0008 (5)	−0.0035 (5)	0.0012 (5)

O1—C2	1.3753 (14)	C2—C3	1.4074 (16)
O1—C8	1.4456 (14)	C3—C4	1.3903 (17)
O2—C3	1.3668 (14)	C4—C5	1.3879 (17)
O2—H2	0.88 (2)	C4—H4	0.9500
O3—C7	1.2499 (14)	C5—C6	1.3822 (17)
N1—C7	1.3267 (16)	C5—H5	0.9500
N1—H1A	0.901 (17)	C6—H6	0.9500
N1—H1B	0.887 (17)	C8—H8A	0.9800
C1—C6	1.3963 (17)	C8—H8B	0.9800
C1—C2	1.4038 (16)	C8—H8C	0.9800
C1—C7	1.5041 (16)
C2—O1—C8	117.88 (9)	C3—C4—H4	119.8
C3—O2—H2	108.9 (12)	C6—C5—C4	119.98 (11)
C7—N1—H1A	118.7 (10)	C6—C5—H5	120.0
C7—N1—H1B	118.8 (10)	C4—C5—H5	120.0
H1A—N1—H1B	121.5 (14)	C5—C6—C1	120.95 (11)
C6—C1—C2	119.12 (10)	C5—C6—H6	119.5
C6—C1—C7	116.33 (10)	C1—C6—H6	119.5
C2—C1—C7	124.46 (11)	O3—C7—N1	120.85 (11)
O1—C2—C1	119.38 (10)	O3—C7—C1	119.49 (10)
O1—C2—C3	120.82 (10)	N1—C7—C1	119.65 (10)
C1—C2—C3	119.71 (11)	O1—C8—H8A	109.5
O2—C3—C4	122.52 (11)	O1—C8—H8B	109.5
O2—C3—C2	117.69 (10)	H8A—C8—H8B	109.5
C4—C3—C2	119.78 (11)	O1—C8—H8C	109.5
C5—C4—C3	120.36 (11)	H8A—C8—H8C	109.5
C5—C4—H4	119.8	H8B—C8—H8C	109.5
C8—O1—C2—C1	−129.31 (11)	O2—C3—C4—C5	177.18 (11)
C8—O1—C2—C3	54.02 (14)	C2—C3—C4—C5	−1.63 (18)
C6—C1—C2—O1	−173.41 (10)	C3—C4—C5—C6	2.32 (19)
C7—C1—C2—O1	10.24 (17)	C4—C5—C6—C1	−0.16 (19)
C6—C1—C2—C3	3.30 (17)	C2—C1—C6—C5	−2.65 (18)
C7—C1—C2—C3	−173.05 (10)	C7—C1—C6—C5	173.99 (11)
O1—C2—C3—O2	−3.41 (16)	C6—C1—C7—O3	−9.95 (17)
C1—C2—C3—O2	179.93 (10)	C2—C1—C7—O3	166.50 (11)
O1—C2—C3—C4	175.47 (10)	C6—C1—C7—N1	170.31 (11)
C1—C2—C3—C4	−1.20 (17)	C2—C1—C7—N1	−13.25 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3i	0.901 (17)	2.056 (17)	2.9547 (13)	175.3 (14)
N1—H1B···O1	0.887 (17)	1.977 (17)	2.6789 (13)	135.0 (14)
O2—H2···O3ii	0.88 (2)	1.83 (2)	2.6895 (12)	165.5 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.901 (17)	2.056 (17)	2.9547 (13)	175.3 (14)
N1—H1B⋯O1	0.887 (17)	1.977 (17)	2.6789 (13)	135.0 (14)
O2—H2⋯O3ii	0.88 (2)	1.83 (2)	2.6895 (12)	165.5 (17)

Symmetry codes: (i) ; (ii) .