1-Oxoisoindoline-2-carboxamide.

The title mol-ecule, C(9)H(8)N(2)O(2), is essentially planar. The crystal structure is stabilized by hydrogen bonding. An intra-molecular N-H⋯O hydrogen bond results in a six-membered ring. Each mol-ecule inter-acts with two others through N-H⋯O and C-H⋯O hydrogen bonding, resulting in the formation of nine-membered rings. These hydrogen bonds generate a two-dimensional polymeric network. There are also π-π inter-actions between the aromatic and heterocyclic rings [centroid-centroid distance 3.638 (2) Å].

Related literature

For related literature, see: Berger et al. (1999 ▶); Cignarella et al. (1981 ▶); Goddard (1977 ▶); Goddard & Levitt (1979 ▶); Maliha et al. (2007 ▶); Mancilla et al. (2007 ▶); Momose (1980 ▶); Zuman (2004 ▶).

Experimental

Crystal data

C9H8N2O2

M = 176.17

Orthorhombic,

a = 3.9839 (3) Å

b = 7.8732 (8) Å

c = 25.651 (2) Å

V = 804.58 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 (2) K

0.25 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.990

5461 measured reflections

1254 independent reflections

860 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.138

S = 1.07

1254 reflections

124 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808004923/at2545sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004923/at2545Isup2.hkl

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

C9H8N2O2	F000 = 368
Mr = 176.17	Dx = 1.454 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1295 reflections
a = 3.9839 (3) Å	θ = 1.6–28.6º
b = 7.8732 (8) Å	µ = 0.11 mm−1
c = 25.651 (2) Å	T = 296 (2) K
V = 804.58 (13) Å3	Needle, colourless
Z = 4	0.25 × 0.12 × 0.10 mm

Bruker KappaAPEXII CCD diffractometer	1254 independent reflections
Radiation source: fine-focus sealed tube	860 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
Detector resolution: 7.40 pixels mm-1	θmax = 28.6º
T = 296(2) K	θmin = 1.6º
ω scans	h = −3→5
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −9→10
Tmin = 0.975, Tmax = 0.990	l = −34→22
5461 measured reflections

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.0804P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1254 reflections	Δρmax = 0.23 e Å−3
124 parameters	Δρmin = −0.22 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
O1	0.1443 (8)	0.5881 (3)	0.09333 (8)	0.0599 (8)
O2	0.3962 (6)	0.7070 (2)	0.24721 (7)	0.0479 (7)
N1	0.1909 (7)	0.7618 (2)	0.16626 (8)	0.0335 (6)
N2	0.3940 (9)	0.4951 (3)	0.18736 (10)	0.0512 (8)
H2A	0.346 (10)	0.476 (4)	0.1514 (13)	0.061*
H2B	0.478 (10)	0.421 (4)	0.2092 (14)	0.061*
C1	0.1002 (9)	0.7240 (3)	0.11498 (10)	0.0380 (7)
C2	−0.0491 (8)	0.8806 (3)	0.09388 (10)	0.0351 (7)
C3	−0.1770 (10)	0.9115 (4)	0.04430 (11)	0.0450 (8)
H3	−0.1780	0.8269	0.0190	0.054*
C4	−0.3025 (9)	1.0715 (4)	0.03378 (12)	0.0491 (8)
H4	−0.3903	1.0952	0.0010	0.059*
C5	−0.2985 (9)	1.1968 (4)	0.07165 (12)	0.0489 (9)
H5	−0.3837	1.3038	0.0639	0.059*
C6	−0.1693 (9)	1.1655 (4)	0.12114 (11)	0.0427 (7)
H6	−0.1652	1.2504	0.1463	0.051*
C7	−0.0474 (8)	1.0053 (3)	0.13185 (10)	0.0343 (7)
C8	0.1037 (9)	0.9367 (3)	0.18109 (9)	0.0335 (7)
H8A	0.3014	1.0006	0.1912	0.040*
H8B	−0.0569	0.9384	0.2095	0.040*
C9	0.3350 (8)	0.6532 (3)	0.20346 (10)	0.0350 (7)

	U11	U22	U33	U12	U13	U23
O1	0.102 (2)	0.0398 (11)	0.0383 (10)	0.0154 (14)	−0.0116 (14)	−0.0118 (9)
O2	0.0734 (18)	0.0362 (11)	0.0340 (10)	0.0018 (12)	−0.0113 (11)	0.0002 (8)
N1	0.0453 (16)	0.0263 (10)	0.0289 (10)	0.0045 (11)	−0.0024 (10)	−0.0006 (8)
N2	0.081 (2)	0.0327 (13)	0.0404 (13)	0.0173 (15)	−0.0087 (15)	0.0015 (10)
C1	0.050 (2)	0.0358 (14)	0.0286 (12)	−0.0004 (15)	−0.0013 (13)	−0.0047 (11)
C2	0.0382 (18)	0.0348 (14)	0.0323 (12)	0.0001 (13)	0.0018 (13)	0.0021 (11)
C3	0.050 (2)	0.0502 (17)	0.0345 (13)	0.0036 (18)	−0.0019 (14)	0.0011 (13)
C4	0.047 (2)	0.064 (2)	0.0366 (13)	0.0042 (19)	−0.0034 (14)	0.0140 (14)
C5	0.047 (2)	0.0477 (18)	0.0518 (17)	0.0100 (17)	0.0017 (16)	0.0159 (15)
C6	0.0473 (19)	0.0352 (14)	0.0455 (15)	0.0051 (16)	0.0040 (15)	0.0022 (12)
C7	0.0365 (18)	0.0344 (14)	0.0321 (12)	0.0019 (13)	0.0018 (12)	0.0016 (11)
C8	0.0437 (19)	0.0274 (12)	0.0293 (11)	0.0002 (14)	0.0001 (12)	−0.0027 (10)
C9	0.0408 (18)	0.0314 (13)	0.0326 (12)	−0.0014 (15)	0.0028 (13)	0.0020 (11)

O1—C1	1.218 (3)	C3—C4	1.382 (4)
O2—C9	1.224 (3)	C3—H3	0.9300
N1—C1	1.396 (3)	C4—C5	1.385 (5)
N1—C9	1.404 (3)	C4—H4	0.9300
N1—C8	1.470 (3)	C5—C6	1.392 (4)
N2—C9	1.332 (3)	C5—H5	0.9300
N2—H2A	0.95 (3)	C6—C7	1.379 (4)
N2—H2B	0.87 (3)	C6—H6	0.9300
C1—C2	1.472 (4)	C7—C8	1.500 (4)
C2—C7	1.383 (4)	C8—H8A	0.9700
C2—C3	1.392 (4)	C8—H8B	0.9700
C1—N1—C9	128.0 (2)	C4—C5—C6	121.2 (3)
C1—N1—C8	112.5 (2)	C4—C5—H5	119.4
C9—N1—C8	119.4 (2)	C6—C5—H5	119.4
C9—N2—H2A	114 (2)	C7—C6—C5	118.3 (3)
C9—N2—H2B	120 (2)	C7—C6—H6	120.8
H2A—N2—H2B	126 (3)	C5—C6—H6	120.8
O1—C1—N1	125.4 (3)	C6—C7—C2	120.5 (2)
O1—C1—C2	128.8 (2)	C6—C7—C8	129.7 (2)
N1—C1—C2	105.8 (2)	C2—C7—C8	109.8 (2)
C7—C2—C3	121.4 (3)	N1—C8—C7	102.36 (19)
C7—C2—C1	109.5 (2)	N1—C8—H8A	111.3
C3—C2—C1	129.1 (2)	C7—C8—H8A	111.3
C4—C3—C2	118.1 (3)	N1—C8—H8B	111.3
C4—C3—H3	121.0	C7—C8—H8B	111.3
C2—C3—H3	121.0	H8A—C8—H8B	109.2
C3—C4—C5	120.6 (3)	O2—C9—N2	124.9 (3)
C3—C4—H4	119.7	O2—C9—N1	119.6 (2)
C5—C4—H4	119.7	N2—C9—N1	115.5 (2)
C9—N1—C1—O1	−2.8 (5)	C5—C6—C7—C8	−179.9 (3)
C8—N1—C1—O1	−179.9 (3)	C3—C2—C7—C6	−0.9 (5)
C9—N1—C1—C2	178.1 (3)	C1—C2—C7—C6	178.8 (3)
C8—N1—C1—C2	1.0 (3)	C3—C2—C7—C8	179.9 (3)
O1—C1—C2—C7	−179.5 (3)	C1—C2—C7—C8	−0.4 (4)
N1—C1—C2—C7	−0.4 (4)	C1—N1—C8—C7	−1.2 (3)
O1—C1—C2—C3	0.2 (6)	C9—N1—C8—C7	−178.5 (2)
N1—C1—C2—C3	179.3 (3)	C6—C7—C8—N1	−178.1 (3)
C7—C2—C3—C4	0.2 (5)	C2—C7—C8—N1	0.9 (3)
C1—C2—C3—C4	−179.5 (3)	C1—N1—C9—O2	−179.3 (3)
C2—C3—C4—C5	0.3 (5)	C8—N1—C9—O2	−2.4 (4)
C3—C4—C5—C6	−0.1 (5)	C1—N1—C9—N2	0.6 (5)
C4—C5—C6—C7	−0.6 (5)	C8—N1—C9—N2	177.5 (3)
C5—C6—C7—C2	1.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.95 (3)	1.91 (3)	2.710 (3)	140 (2)
N2—H2B···O2i	0.88 (3)	2.08 (3)	2.943 (3)	167 (3)
C8—H8A···O2ii	0.97	2.57	3.447 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.95 (3)	1.91 (3)	2.710 (3)	140 (2)
N2—H2B⋯O2i	0.88 (3)	2.08 (3)	2.943 (3)	167 (3)
C8—H8A⋯O2ii	0.97	2.57	3.447 (4)	151

Symmetry codes: (i) ; (ii) .