organic compounds
N-Methyl-1-oxoisoindoline-2-carboxamide monohydrate
aUniversity of the Punjab, Institute of Chemistry, Lahore-54590, Pakistan, bUniversity of Sargodha, Department of Chemistry, Sargodha, Pakistan, cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and dUniversity of the Punjab, Institute of Chemistry, Lahore 54590, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com
The title compound, C10H10N2O2·H2O, is dimerized by inversion-related intermolecular N—H⋯O hydrogen bonding. There is an intramolecular N—H⋯O bond, resulting in a six-membered ring. Each dimer interacts with other dimers through hydrogen bonding with water molecules. The water molecules 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 intermolecular C—H⋯O hydrogen bonding. There are π–π interactions between the aromatic and heterocyclic five-membered rings [centroid–centroid distance 3.8360 (12) Å]. C—H⋯π interactions also exist between CH2 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
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell 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.
Supporting information
10.1107/S1600536808008362/bq2071sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008362/bq2071Isup2.hkl
A mixture of o-phthaldehyde (0.67 g, 200 mmol) and N-methylurea (0.37 g, 200 mmol) in 100 ml of ethanol was refluxed for 10 h. The solvent was taken off and flask contents were left at room temperature. The crystals of (I) were isolated, washed with ethanol, ether and n-hexane, respectively and dried. Crystals suitable for X-ray diffraction were grown from a mixture of methanol-acetone (1:1) by slow evaporation at room temperature. It is soluble in DMSO, DMF, acetone, ethyl acetate, chloroform and carbon tetrachloride. M.P: 413 K; yield: 60 percent.
H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl C-atoms and constrained to ride on their parent atoms. The H-atoms attached to N2 and O3 atoms were located in fourier synthesis and their coordinates were refined. The thermal parameter of H-atoms of methyl group was taken 1.5 times of the parent C-atom, whereas for all other H-atoms it was taken 1.2 times of their parent atoms.
Data collection: APEX2 (Bruker, 2007); cell
APEX2 (Bruker, 2007); 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 (Spek, 2003).Fig. 1. The ORTEP diagram of the title compound (I) with displacement ellipsoids at 50% probability level; intramolecular interaction has been indicated by broken line. H-atoms are shown by small circles of arbitrary radii. | |
Fig. 2. The packing figure (PLATON: Spek, 2003) which shows the H-bonding and the overlapping of rings which generate π-π interaction. |
C10H10N2O2·H2O | F(000) = 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 = 1.4–28.5° |
b = 29.0200 (16) Å | µ = 0.10 mm−1 |
c = 4.8864 (2) Å | T = 296 K |
β = 108.266 (3)° | 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) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 7.40 pixels mm-1 | θmax = 28.5°, θmin = 1.4° |
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 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.045P)2 + 0.3992P] where P = (Fo2 + 2Fc2)/3 |
2518 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C10H10N2O2·H2O | V = 1000.02 (9) Å3 |
Mr = 208.22 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.4264 (4) Å | µ = 0.10 mm−1 |
b = 29.0200 (16) Å | T = 296 K |
c = 4.8864 (2) Å | 0.22 × 0.12 × 0.10 mm |
β = 108.266 (3)° |
Bruker Kappa APEXII CCD diffractometer | 2518 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1586 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.990 | Rint = 0.042 |
18083 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.130 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.23 e Å−3 |
2518 reflections | Δρmin = −0.20 e Å−3 |
145 parameters |
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 |
Symmetry codes: (i) −x, −y, −z; (ii) x+1, y, z; (iii) x, −y+1/2, z−1/2; (iv) x+1, y, z−1; (v) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H10N2O2·H2O |
Mr | 208.22 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 7.4264 (4), 29.0200 (16), 4.8864 (2) |
β (°) | 108.266 (3) |
V (Å3) | 1000.02 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.22 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.980, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18083, 2518, 1586 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.672 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.130, 1.05 |
No. of reflections | 2518 |
No. of parameters | 145 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.23, −0.20 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
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) −x, −y, −z; (ii) x+1, y, z; (iii) x, −y+1/2, z−1/2; (iv) x+1, y, z−1; (v) x, y, z+1. |
Acknowledgements
The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, for providing the Kappa APEXII CCD diffractometer.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Isoindole and their derivatives are known to be active-compounds pharmaceutically (Straub et al., 2007; Mancilla et al., 2007). They are important intermediates in the synthesis of novel multi-drugs resistance reversal agents (Berger et al., 1999). They show diuretic, anti-anginal, cardio-vascular and herbicidal activitities (Alberto et al., 1994; Cignarella et al., 1981; Toru et al., 1986).
The title compound (I) is in continuation to the synthesis of various isoindoles and the determination of their structures by X-ray crystallography (Maliha et al., 2007; 2008). It was isolated during the studies of the reaction of urea and its N-alkyl/aryl derivates with o-phthaldehyde.
The present structure shows that replacing the H-atom of 1-Oxoisoindoline-2- carboxamide (Maliha et al., 2008) with CH3 group, is possible in the presence of crystallization water only. The replacement of H-atom of 1-Oxoisoindoline-2-carboxamide with ethyl group (Wan et al., 2007) also shows the existence of crystallizing H2O. Although the bond distances and bond angles in the aromatic A(C2—C7) and five-membered ring B(C1/C2/C7/C8/N1) are comparable with the reported structures (Maliha et al., 2008; Wan et al., 2007), but the packing through H-bonding is entirely different. There is an intramolecular hydrogen bond of N2—H2···O1 resulting in a six-membered ring. The title compound is dimerized by inversion of N-methyl-1-oxo-1,3-dihydro-2H-isoindole-2-carboxamide through intermolecular H-bond viz N2—H2···O1i [symmetry code i = -x,-y,-z] and the central ring is of four members depending upon these H-bonds only. The role of H2O molecules is to stabilize the dimers through an interesting H-bonding. The H-bond O3—H1W···O2ii [symmetry code ii = x + 1, y, z] connects the dimers, while the O3—H2W···O3iii [symmetry code iii = x, -y + 1/2, z - 1/2] joints the water molecules in a stair like chain. In this way two-dimensional polymeric strip is realized. These polymeric strips are further connected by the involvement of aromatic ring A(C2—C7) through intermolecular H-bonds C4—H4···O2iv [symmetry code iv = x + 1, y, z - 1]. The detail of H-bonding is given in Table 1 and shown in Fig. 2. The π-π interaction exist between the CgA···CgBv [symmetry code v = x,y,z - 1] and CgB···CgAvi [symmetry code vi = x,y,z + 1] having same centroid-centroid distance of 3.8360 (12) Å. The C—H···π interaction exists between C8—H8A and CgAvi [symmetry code vi = x,y,z + 1] with H8A···π distance of 2.86 Å.