N-Methyl-1-oxoisoindoline-2-carboxamide monohydrate.

The title compound, C(10)H(10)N(2)O(2)·H(2)O, is dimerized by inversion-related inter-molecular N-H⋯O hydrogen bonding. There is an intra-molecular N-H⋯O bond, resulting in a six-membered ring. Each dimer inter-acts with other dimers through hydrogen bonding with water mol-ecules. The water mol-ecules are linked to each other in a stair-like chain, thus generating two-dimensional polymeric strips. The dimers are also linked to each other through inter-molecular C-H⋯O hydrogen bonding. There are π-π inter-actions between the aromatic and heterocyclic five-membered rings [centroid-centroid distance 3.8360 (12) Å]. C-H⋯π inter-actions also exist between CH(2) groups and aromatic rings.

Related literature

For related literature, see: Alberto et al. (1994 ▶); Berger et al. (1999 ▶); Cignarella et al. (1981 ▶); Maliha et al. (2008 ▶); Mancilla et al. (2007 ▶); Toru et al. (1986 ▶); Wan et al. (2007 ▶); Straub et al. (2007 ▶); Maliha et al. (2007 ▶).

Experimental

Crystal data

C10H10N2O2·H2O

M = 208.22

Monoclinic,

a = 7.4264 (4) Å

b = 29.0200 (16) Å

c = 4.8864 (2) Å

β = 108.266 (3)°

V = 1000.02 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 (2) K

0.22 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.980, T max = 0.990

18083 measured reflections

2518 independent reflections

1586 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.130

S = 1.05

2518 reflections

145 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.20 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/S1600536808008362/bq2071sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008362/bq2071Isup2.hkl

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

C10H10N2O2·H2O	F000 = 440
Mr = 208.22	Dx = 1.383 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1295 reflections
a = 7.4264 (4) Å	θ = 1.4–28.5º
b = 29.0200 (16) Å	µ = 0.10 mm−1
c = 4.8864 (2) Å	T = 296 (2) K
β = 108.266 (3)º	Needle, colourless
V = 1000.02 (9) Å3	0.22 × 0.12 × 0.10 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2518 independent reflections
Radiation source: fine-focus sealed tube	1586 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.042
Detector resolution: 7.40 pixels mm-1	θmax = 28.5º
T = 296(2) K	θmin = 1.4º
ω scans	h = −9→9
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −38→38
Tmin = 0.980, Tmax = 0.990	l = −6→6
18083 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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.045P)2 + 0.3992P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2518 reflections	Δρmax = 0.23 e Å−3
145 parameters	Δρmin = −0.20 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	0.1330 (2)	0.04176 (5)	−0.0048 (4)	0.0582 (4)
O2	−0.17938 (19)	0.12874 (4)	0.3549 (3)	0.0452 (4)
O3	0.8077 (3)	0.22691 (6)	0.4262 (4)	0.0721 (6)
H1W	0.815 (4)	0.1993 (11)	0.404 (6)	0.086*
H2W	0.812 (4)	0.2398 (10)	0.266 (6)	0.086*
N1	0.0204 (2)	0.11191 (5)	0.0993 (3)	0.0357 (4)
N2	−0.1470 (3)	0.05442 (6)	0.2455 (4)	0.0477 (5)
H2	−0.088 (3)	0.0368 (8)	0.170 (5)	0.057*
C1	0.1337 (3)	0.08376 (6)	−0.0065 (4)	0.0377 (4)
C2	0.2523 (3)	0.11487 (6)	−0.1134 (4)	0.0364 (4)
C3	0.3901 (3)	0.10422 (7)	−0.2420 (4)	0.0456 (5)
H3	0.4175	0.0738	−0.2733	0.055*
C4	0.4848 (3)	0.14010 (8)	−0.3213 (5)	0.0498 (5)
H4	0.5771	0.1339	−0.4083	0.060*
C5	0.4434 (3)	0.18515 (8)	−0.2725 (5)	0.0519 (6)
H5	0.5099	0.2089	−0.3248	0.062*
C6	0.3054 (3)	0.19572 (7)	−0.1477 (5)	0.0487 (5)
H6	0.2776	0.2262	−0.1178	0.058*
C7	0.2099 (3)	0.15985 (6)	−0.0683 (4)	0.0366 (4)
C8	0.0559 (3)	0.16101 (6)	0.0683 (4)	0.0388 (4)
H8A	0.0976	0.1763	0.2541	0.047*
H8B	−0.0564	0.1764	−0.0545	0.047*
C9	−0.1088 (3)	0.09905 (6)	0.2436 (4)	0.0353 (4)
C10	−0.2783 (3)	0.03691 (7)	0.3864 (5)	0.0572 (6)
H10A	−0.2584	0.0044	0.4196	0.086*
H10B	−0.4061	0.0423	0.2656	0.086*
H10C	−0.2574	0.0524	0.5671	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0756 (11)	0.0306 (8)	0.0904 (12)	0.0029 (7)	0.0575 (9)	−0.0003 (7)
O2	0.0536 (8)	0.0382 (8)	0.0563 (9)	0.0004 (6)	0.0352 (7)	−0.0060 (6)
O3	0.1328 (17)	0.0403 (9)	0.0591 (10)	0.0134 (10)	0.0530 (11)	−0.0006 (8)
N1	0.0431 (9)	0.0303 (8)	0.0412 (9)	0.0006 (7)	0.0242 (7)	0.0002 (6)
N2	0.0618 (12)	0.0345 (10)	0.0632 (12)	0.0022 (8)	0.0432 (10)	0.0014 (8)
C1	0.0434 (11)	0.0340 (11)	0.0425 (10)	0.0024 (8)	0.0231 (8)	−0.0003 (8)
C2	0.0382 (10)	0.0383 (10)	0.0363 (10)	−0.0004 (8)	0.0170 (8)	0.0001 (7)
C3	0.0469 (12)	0.0447 (12)	0.0534 (12)	0.0026 (9)	0.0275 (10)	−0.0007 (9)
C4	0.0414 (12)	0.0589 (14)	0.0581 (13)	−0.0022 (10)	0.0283 (10)	0.0023 (10)
C5	0.0484 (13)	0.0526 (14)	0.0610 (14)	−0.0120 (10)	0.0260 (11)	0.0046 (10)
C6	0.0586 (14)	0.0367 (11)	0.0572 (13)	−0.0086 (10)	0.0274 (11)	−0.0032 (9)
C7	0.0404 (11)	0.0378 (10)	0.0344 (10)	−0.0026 (8)	0.0157 (8)	−0.0028 (7)
C8	0.0480 (12)	0.0307 (10)	0.0445 (11)	−0.0010 (8)	0.0245 (9)	−0.0019 (8)
C9	0.0399 (10)	0.0359 (10)	0.0347 (10)	0.0011 (8)	0.0185 (8)	0.0011 (7)
C10	0.0680 (15)	0.0460 (13)	0.0749 (16)	−0.0033 (11)	0.0475 (13)	0.0046 (11)

O1—C1	1.219 (2)	C3—H3	0.9300
O2—C9	1.221 (2)	C4—C5	1.381 (3)
O3—H1W	0.81 (3)	C4—H4	0.9300
O3—H2W	0.88 (3)	C5—C6	1.381 (3)
N1—C1	1.384 (2)	C5—H5	0.9300
N1—C9	1.408 (2)	C6—C7	1.382 (3)
N1—C8	1.466 (2)	C6—H6	0.9300
N2—C9	1.326 (2)	C7—C8	1.495 (2)
N2—C10	1.451 (2)	C8—H8A	0.9700
N2—H2	0.83 (2)	C8—H8B	0.9700
C1—C2	1.467 (2)	C10—H10A	0.9600
C2—C7	1.377 (3)	C10—H10B	0.9600
C2—C3	1.393 (2)	C10—H10C	0.9600
C3—C4	1.378 (3)
H1W—O3—H2W	106 (3)	C5—C6—C7	118.27 (19)
C1—N1—C9	128.36 (15)	C5—C6—H6	120.9
C1—N1—C8	112.66 (14)	C7—C6—H6	120.9
C9—N1—C8	118.83 (14)	C2—C7—C6	120.43 (17)
C9—N2—C10	121.47 (17)	C2—C7—C8	109.75 (15)
C9—N2—H2	117.0 (16)	C6—C7—C8	129.82 (17)
C10—N2—H2	121.4 (16)	N1—C8—C7	102.22 (14)
O1—C1—N1	125.66 (16)	N1—C8—H8A	111.3
O1—C1—C2	128.49 (16)	C7—C8—H8A	111.3
N1—C1—C2	105.84 (15)	N1—C8—H8B	111.3
C7—C2—C3	121.29 (17)	C7—C8—H8B	111.3
C7—C2—C1	109.52 (15)	H8A—C8—H8B	109.2
C3—C2—C1	129.19 (17)	O2—C9—N2	124.32 (16)
C4—C3—C2	118.08 (19)	O2—C9—N1	119.40 (16)
C4—C3—H3	121.0	N2—C9—N1	116.28 (15)
C2—C3—H3	121.0	N2—C10—H10A	109.5
C3—C4—C5	120.40 (18)	N2—C10—H10B	109.5
C3—C4—H4	119.8	H10A—C10—H10B	109.5
C5—C4—H4	119.8	N2—C10—H10C	109.5
C4—C5—C6	121.52 (19)	H10A—C10—H10C	109.5
C4—C5—H5	119.2	H10B—C10—H10C	109.5
C6—C5—H5	119.2
C9—N1—C1—O1	4.1 (3)	C3—C2—C7—C8	179.20 (18)
C8—N1—C1—O1	179.5 (2)	C1—C2—C7—C8	−1.0 (2)
C9—N1—C1—C2	−175.17 (17)	C5—C6—C7—C2	0.0 (3)
C8—N1—C1—C2	0.2 (2)	C5—C6—C7—C8	−179.8 (2)
O1—C1—C2—C7	−178.7 (2)	C1—N1—C8—C7	−0.8 (2)
N1—C1—C2—C7	0.5 (2)	C9—N1—C8—C7	175.07 (15)
O1—C1—C2—C3	1.0 (4)	C2—C7—C8—N1	1.1 (2)
N1—C1—C2—C3	−179.76 (19)	C6—C7—C8—N1	−179.0 (2)
C7—C2—C3—C4	0.5 (3)	C10—N2—C9—O2	−0.6 (3)
C1—C2—C3—C4	−179.19 (19)	C10—N2—C9—N1	−179.81 (19)
C2—C3—C4—C5	0.3 (3)	C1—N1—C9—O2	170.66 (18)
C3—C4—C5—C6	−0.9 (3)	C8—N1—C9—O2	−4.5 (3)
C4—C5—C6—C7	0.8 (3)	C1—N1—C9—N2	−10.0 (3)
C3—C2—C7—C6	−0.7 (3)	C8—N1—C9—N2	174.80 (17)
C1—C2—C7—C6	179.08 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.83 (3)	2.08 (2)	2.748 (3)	137 (2)
N2—H2···O1i	0.83 (2)	2.41 (2)	3.043 (2)	134 (2)
O3—H1W···O2ii	0.81 (3)	2.06 (3)	2.875 (2)	177 (3)
O3—H2W···O3iii	0.88 (3)	1.91 (3)	2.787 (3)	174 (3)
C4—H4···O2iv	0.93	2.44	3.362 (3)	172
C8—H8A···Cg1v	0.97	2.86	3.590 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.83 (3)	2.08 (2)	2.748 (3)	137 (2)
N2—H2⋯O1i	0.83 (2)	2.41 (2)	3.043 (2)	134 (2)
O3—H1W⋯O2ii	0.81 (3)	2.06 (3)	2.875 (2)	177 (3)
O3—H2W⋯O3iii	0.88 (3)	1.91 (3)	2.787 (3)	174 (3)
C4—H4⋯O2iv	0.93	2.44	3.362 (3)	172
C8—H8A⋯Cg1v	0.97	2.86	3.590 (2)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 is the centroid of atoms C2–C7.