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Acta Cryst. (2009). E65, o1210    [ doi:10.1107/S1600536809015621 ]

N-(2-Hydroxyethyl)-1,8-naphthalimide

J. Sun, A. Yuan, H.-B. Wang and J. Sun

Abstract top

In the molecule of the title compound, C14H11NO3, the naphthalimide ring system is nearly planar (r.m.s. deviation 0.0139 Å). In the crystal structure, intermolecular O-H...O hydrogen bonds link the molecules into centrosymmetric dimers forming R22(14) ring motifs. [pi]-[pi] contacts between the naphthalimide rings [centroid-centroid distances = 3.648 (3), 3.783 (3), 3.635 (3), 3.722 (3) and 3.755 (3) Å] may further stabilize the structure.

Comment top

As part of our ongoing studies on N-substituted 1,8-naphthalimides (Prezhdo et al., 2007), we report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (N/C3-C5/C10/C11), B (C5-C10) and C (C9-C14) are, of course, planar, and they are oriented at dihedral angles of A/B = 1.79 (3), A/C = 1.14 (3) and B/C = 1.00 (3) °. So, they are nearly coplanar. Intramolecular C-H···O interaction (Table 1) results in the formation of a five-membered ring D (O2/N/C2/C3/H2A), having envelope conformation, with atom H2A displaced by -0.302 (3) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular O-H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers forming R22(14) ring motifs (Fig. 2) (Bernstein et al., 1996), in which they may be effective in the stabilization of the structure. The π–π contacts between the naphthalimide rings, Cg1—Cg1i, Cg1—Cg2i, Cg1—Cg3ii, Cg2—Cg3ii and Cg3—Cg3ii [symmetry codes: (i) 1 - x, 1 - y, 1 - z, (ii) 2 - x, 1 - y, 1 - z, where Cg1, Cg2 and Cg3 are centroids of the rings A (N/C3-C5/C10/C11), B (C5-C10) and C (C9-C14), respectively] may further stabilize the structure, with centroid-centroid distances of 3.648 (3), 3.783 (3), 3.635 (3), 3.722 (3) and 3.755 (3) Å, respectively.

Related literature top

For a related structure, see: Prezhdo et al. (2007). For bond-length data, see: Allen et al. (1987). For ring-motifs, see: Bernstein et al. (1995).

Experimental top

For the preparation of the title compound, 1,8-naphthalic anhydride (1.98 g, 0.01 mol) and 2-aminoethanol (0.02 mol) were mixed with acetic acid (50 ml). The reaction mixture was refluxed for 8 h, and then poured into cold water. The resulting solids were filtered off. The solid products were boiled with an aqueous solution of sodium bicarbonate (10%, 50 ml) for 20 min, and the insoluble solid residues were dried in vacuo. Column chromatography on aluminium oxide with the C6H6 eluent gave light-brown solution. Crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone solution (yield; 96%, m.p. 413 K).

Refinement top

H atoms were positioned geometrically, with O-H = 0.82 Å (for OH) and C-H = 0.93 and 0.97 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.5 for OH H and x = 1.2 for all other H atoms.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bond is shown as dashed line.
[Figure 2] Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.
N-(2-Hydroxyethyl)naphthalene-1,8-dicarboximide top
Crystal data top
C14H11NO3Z = 2
Mr = 241.24F000 = 252
Triclinic, P1Dx = 1.461 Mg m−3
Hall symbol: -P 1Melting point: 413 K
a = 7.5480 (15) ÅMo Kα radiation
λ = 0.71073 Å
b = 8.8300 (18) ÅCell parameters from 25 reflections
c = 10.101 (2) Åθ = 10–13º
α = 96.760 (19)ºµ = 0.10 mm−1
β = 109.94 (3)ºT = 294 K
γ = 114.60 (3)ºBlock, green
V = 548.2 (3) Å30.30 × 0.20 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.023
Radiation source: fine-focus sealed tubeθmax = 25.3º
Monochromator: graphiteθmin = 2.3º
T = 294 Kh = 0→9
ω/2θ scansk = −10→9
Absorption correction: ψ scan
(North et al., 1968)		l = −12→11
Tmin = 0.970, Tmax = 0.9903 standard reflections
2159 measured reflections every 120 min
1995 independent reflections intensity decay: 1%
1330 reflections with I > 2σ(I)
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054  w = 1/[σ2(Fo2) + (0.1P)2 + 0.4P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.208(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.29 e Å−3
1995 reflectionsΔρmin = −0.31 e Å−3
164 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.035 (10)
Secondary atom site location: difference Fourier map
Crystal data top
C14H11NO3γ = 114.60 (3)º
Mr = 241.24V = 548.2 (3) Å3
Triclinic, P1Z = 2
a = 7.5480 (15) ÅMo Kα
b = 8.8300 (18) ŵ = 0.10 mm−1
c = 10.101 (2) ÅT = 294 K
α = 96.760 (19)º0.30 × 0.20 × 0.10 mm
β = 109.94 (3)º
Data collection top
Enraf–Nonius CAD-4
diffractometer		1330 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.023
Tmin = 0.970, Tmax = 0.9903 standard reflections
2159 measured reflections every 120 min
1995 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.054164 parameters
wR(F2) = 0.208H-atom parameters constrained
S = 1.00Δρmax = 0.29 e Å−3
1995 reflectionsΔρmin = −0.31 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4860 (4)0.2063 (3)−0.0242 (2)0.0624 (7)
H1A0.47630.2711−0.07490.094*
O20.6221 (4)0.5936 (3)0.1937 (3)0.0677 (8)
O30.2875 (4)0.1029 (3)0.3070 (3)0.0729 (8)
N0.4553 (4)0.3481 (3)0.2496 (3)0.0480 (7)
C10.3020 (6)0.1341 (5)0.0027 (4)0.0599 (9)
H1B0.30520.04550.05040.072*
H1C0.17460.0767−0.09130.072*
C20.2818 (5)0.2660 (5)0.0982 (4)0.0610 (10)
H2A0.28280.35660.05220.073*
H2B0.14390.20810.10260.073*
C30.6193 (5)0.5166 (4)0.2858 (3)0.0472 (8)
C40.4392 (5)0.2495 (4)0.3487 (4)0.0509 (8)
C50.6124 (5)0.3314 (4)0.5006 (3)0.0464 (8)
C60.6103 (6)0.2394 (5)0.6016 (4)0.0601 (10)
H6A0.49750.12630.57430.072*
C70.7759 (7)0.3145 (5)0.7442 (4)0.0677 (11)
H7A0.77260.25100.81140.081*
C80.9433 (6)0.4804 (5)0.7870 (4)0.0601 (9)
H8A1.05310.52860.88260.072*
C90.9504 (5)0.5784 (4)0.6872 (3)0.0450 (7)
C100.7830 (5)0.5027 (4)0.5413 (3)0.0407 (7)
C110.7899 (5)0.5973 (4)0.4390 (3)0.0423 (7)
C120.9566 (5)0.7653 (4)0.4817 (4)0.0494 (8)
H12A0.96110.82820.41420.059*
C131.1206 (5)0.8421 (4)0.6277 (4)0.0560 (9)
H13A1.23170.95620.65620.067*
C141.1181 (5)0.7516 (5)0.7266 (4)0.0536 (9)
H14A1.22830.80410.82220.064*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0681 (16)0.0792 (17)0.0581 (15)0.0486 (14)0.0293 (12)0.0251 (12)
O20.0783 (17)0.0742 (17)0.0564 (15)0.0431 (14)0.0243 (13)0.0308 (13)
O30.0595 (16)0.0526 (15)0.0854 (19)0.0114 (13)0.0330 (14)0.0078 (13)
N0.0442 (15)0.0521 (15)0.0468 (15)0.0266 (13)0.0177 (12)0.0061 (12)
C10.057 (2)0.059 (2)0.053 (2)0.0252 (17)0.0200 (16)0.0039 (16)
C20.0468 (19)0.068 (2)0.055 (2)0.0298 (17)0.0112 (16)0.0000 (17)
C30.0512 (19)0.0525 (18)0.0517 (19)0.0341 (16)0.0260 (15)0.0161 (15)
C40.0480 (19)0.0451 (18)0.063 (2)0.0226 (16)0.0310 (16)0.0069 (15)
C50.0514 (18)0.0469 (17)0.0566 (19)0.0302 (15)0.0327 (16)0.0148 (15)
C60.078 (2)0.056 (2)0.075 (3)0.0383 (19)0.054 (2)0.0285 (18)
C70.095 (3)0.081 (3)0.063 (2)0.057 (2)0.049 (2)0.039 (2)
C80.073 (2)0.081 (3)0.051 (2)0.052 (2)0.0338 (18)0.0238 (18)
C90.0469 (17)0.0588 (19)0.0434 (17)0.0359 (16)0.0232 (14)0.0123 (14)
C100.0421 (16)0.0460 (16)0.0483 (17)0.0291 (14)0.0260 (14)0.0120 (13)
C110.0455 (17)0.0447 (16)0.0463 (17)0.0296 (14)0.0214 (14)0.0119 (13)
C120.0551 (19)0.0443 (17)0.062 (2)0.0293 (15)0.0328 (16)0.0171 (15)
C130.0434 (18)0.0478 (18)0.068 (2)0.0186 (15)0.0238 (17)0.0021 (17)
C140.0481 (18)0.065 (2)0.0490 (19)0.0339 (17)0.0190 (15)0.0025 (16)
Geometric parameters (Å, °) top
O1—C11.403 (4)C6—C71.391 (5)
O1—H1A0.8200C6—H6A0.9300
O2—C31.216 (4)C7—C81.366 (5)
O3—C41.214 (4)C7—H7A0.9300
N—C21.470 (4)C8—C91.404 (5)
N—C31.383 (4)C8—H8A0.9300
N—C41.404 (4)C9—C101.418 (4)
C1—C21.515 (5)C9—C141.414 (5)
C1—H1B0.9700C10—C111.405 (4)
C1—H1C0.9700C11—C121.376 (4)
C2—H2A0.9700C12—C131.410 (5)
C2—H2B0.9700C12—H12A0.9300
C3—C111.476 (4)C13—C141.351 (5)
C4—C51.474 (5)C13—H13A0.9300
C5—C61.378 (5)C14—H14A0.9300
C5—C101.409 (4)
C1—O1—H1A109.5C5—C6—H6A119.8
C3—N—C4124.6 (3)C7—C6—H6A119.8
C3—N—C2118.3 (3)C8—C7—C6120.9 (3)
C4—N—C2117.1 (3)C8—C7—H7A119.6
O1—C1—C2114.2 (3)C6—C7—H7A119.6
O1—C1—H1B108.7C7—C8—C9120.4 (3)
C2—C1—H1B108.7C7—C8—H8A119.8
O1—C1—H1C108.7C9—C8—H8A119.8
C2—C1—H1C108.7C8—C9—C14122.6 (3)
H1B—C1—H1C107.6C8—C9—C10119.2 (3)
N—C2—C1113.5 (3)C14—C9—C10118.2 (3)
N—C2—H2A108.9C11—C10—C5120.9 (3)
C1—C2—H2A108.9C11—C10—C9120.0 (3)
N—C2—H2B108.9C5—C10—C9119.1 (3)
C1—C2—H2B108.9C12—C11—C10119.9 (3)
H2A—C2—H2B107.7C12—C11—C3120.0 (3)
O2—C3—N120.7 (3)C10—C11—C3120.1 (3)
O2—C3—C11121.9 (3)C11—C12—C13120.1 (3)
N—C3—C11117.4 (3)C11—C12—H12A119.9
O3—C4—N119.8 (3)C13—C12—H12A119.9
O3—C4—C5123.0 (3)C14—C13—C12120.7 (3)
N—C4—C5117.2 (3)C14—C13—H13A119.7
C6—C5—C10120.1 (3)C12—C13—H13A119.7
C6—C5—C4120.1 (3)C13—C14—C9121.1 (3)
C10—C5—C4119.8 (3)C13—C14—H14A119.4
C5—C6—C7120.4 (3)C9—C14—H14A119.4
C3—N—C2—C1103.2 (4)C4—C5—C10—C110.4 (4)
C4—N—C2—C1−78.1 (4)C6—C5—C10—C9−0.4 (4)
O1—C1—C2—N−64.6 (4)C4—C5—C10—C9−178.9 (2)
C4—N—C3—O2180.0 (3)C8—C9—C10—C11−178.6 (3)
C2—N—C3—O2−1.4 (4)C14—C9—C10—C111.9 (4)
C4—N—C3—C110.5 (4)C8—C9—C10—C50.7 (4)
C2—N—C3—C11179.1 (2)C14—C9—C10—C5−178.9 (2)
C3—N—C4—O3179.1 (3)C5—C10—C11—C12179.1 (2)
C2—N—C4—O30.5 (4)C9—C10—C11—C12−1.6 (4)
C3—N—C4—C5−1.2 (4)C5—C10—C11—C3−1.1 (4)
C2—N—C4—C5−179.9 (2)C9—C10—C11—C3178.1 (2)
O3—C4—C5—C62.0 (5)O2—C3—C11—C121.0 (4)
N—C4—C5—C6−177.7 (3)N—C3—C11—C12−179.6 (3)
O3—C4—C5—C10−179.6 (3)O2—C3—C11—C10−178.8 (3)
N—C4—C5—C100.8 (4)N—C3—C11—C100.7 (4)
C10—C5—C6—C70.1 (5)C10—C11—C12—C130.2 (4)
C4—C5—C6—C7178.5 (3)C3—C11—C12—C13−179.5 (3)
C5—C6—C7—C80.0 (5)C11—C12—C13—C140.9 (4)
C6—C7—C8—C90.2 (5)C12—C13—C14—C9−0.6 (5)
C7—C8—C9—C14178.9 (3)C8—C9—C14—C13179.7 (3)
C7—C8—C9—C10−0.6 (5)C10—C9—C14—C13−0.8 (4)
C6—C5—C10—C11178.8 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.821.972.771 (4)165
C2—H2A···O20.972.312.714 (5)104
Symmetry codes: (i) −x+1, −y+1, −z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.821.972.771 (4)165
C2—H2A···O20.972.312.714 (5)104
Symmetry codes: (i) −x+1, −y+1, −z.
references
References top

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