N-(2-Hydroxy­ethyl)-1,8-naphthalimide

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

doi:10.1107/S1600536809015621

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1210

doi:10.1107/S1600536809015621

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

Jie Sun,^a ^* Ai-lin Yuan,^a Hai-Bo Wang ^a and Jie Sun ^a

^aCollege of Food Science and Light Industry, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: sunjie5516@126.com

(Received 22 April 2009; accepted 27 April 2009; online 7 May 2009)

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. π–π 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.

Related literature

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

Crystal data

C₁₄H₁₁NO₃
M_r = 241.24
Triclinic, $[P \overline 1]$
a = 7.5480 (15) Å
b = 8.8300 (18) Å
c = 10.101 (2) Å
α = 96.760 (19)°
β = 109.94 (3)°
γ = 114.60 (3)°
V = 548.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.970, T_max = 0.990
2159 measured reflections
1995 independent reflections
1330 reflections with I > 2σ(I)
R_int = 0.023
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.208
S = 1.00
1995 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2ⁱ	0.82	1.97	2.771 (4)	165
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; 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 and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015621/hk2674sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015621/hk2674Isup2.hkl

checkCIF report

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).

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

	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.
	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

C₁₄H₁₁NO₃	Z = 2
M_r = 241.24	F(000) = 252
Triclinic, P1	D_x = 1.461 Mg m⁻³
Hall symbol: -P 1	Melting point: 413 K
a = 7.5480 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8300 (18) Å	Cell parameters from 25 reflections
c = 10.101 (2) Å	θ = 10–13°
α = 96.760 (19)°	µ = 0.10 mm⁻¹
β = 109.94 (3)°	T = 294 K
γ = 114.60 (3)°	Block, green
V = 548.2 (3) Å³	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1330 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 25.3°, θ_min = 2.3°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −10→9
T_min = 0.970, T_max = 0.990	l = −12→11
2159 measured reflections	3 standard reflections every 120 min
1995 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.054	H-atom parameters constrained
wR(F²) = 0.208	w = 1/[σ²(F_o²) + (0.1P)² + 0.4P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
1995 reflections	Δρ_max = 0.29 e Å⁻³
164 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (10)

Crystal data top

C₁₄H₁₁NO₃	γ = 114.60 (3)°
M_r = 241.24	V = 548.2 (3) Å³
Triclinic, P1	Z = 2
a = 7.5480 (15) Å	Mo Kα radiation
b = 8.8300 (18) Å	µ = 0.10 mm⁻¹
c = 10.101 (2) Å	T = 294 K
α = 96.760 (19)°	0.30 × 0.20 × 0.10 mm
β = 109.94 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1330 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.023
T_min = 0.970, T_max = 0.990	3 standard reflections every 120 min
2159 measured reflections	intensity decay: 1%
1995 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.208	H-atom parameters constrained
S = 1.00	Δρ_max = 0.29 e Å⁻³
1995 reflections	Δρ_min = −0.31 e Å⁻³
164 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.4860 (4)	0.2063 (3)	−0.0242 (2)	0.0624 (7)
H1A	0.4763	0.2711	−0.0749	0.094*
O2	0.6221 (4)	0.5936 (3)	0.1937 (3)	0.0677 (8)
O3	0.2875 (4)	0.1029 (3)	0.3070 (3)	0.0729 (8)
N	0.4553 (4)	0.3481 (3)	0.2496 (3)	0.0480 (7)
C1	0.3020 (6)	0.1341 (5)	0.0027 (4)	0.0599 (9)
H1B	0.3052	0.0455	0.0504	0.072*
H1C	0.1746	0.0767	−0.0913	0.072*
C2	0.2818 (5)	0.2660 (5)	0.0982 (4)	0.0610 (10)
H2A	0.2828	0.3566	0.0522	0.073*
H2B	0.1439	0.2081	0.1026	0.073*
C3	0.6193 (5)	0.5166 (4)	0.2858 (3)	0.0472 (8)
C4	0.4392 (5)	0.2495 (4)	0.3487 (4)	0.0509 (8)
C5	0.6124 (5)	0.3314 (4)	0.5006 (3)	0.0464 (8)
C6	0.6103 (6)	0.2394 (5)	0.6016 (4)	0.0601 (10)
H6A	0.4975	0.1263	0.5743	0.072*
C7	0.7759 (7)	0.3145 (5)	0.7442 (4)	0.0677 (11)
H7A	0.7726	0.2510	0.8114	0.081*
C8	0.9433 (6)	0.4804 (5)	0.7870 (4)	0.0601 (9)
H8A	1.0531	0.5286	0.8826	0.072*
C9	0.9504 (5)	0.5784 (4)	0.6872 (3)	0.0450 (7)
C10	0.7830 (5)	0.5027 (4)	0.5413 (3)	0.0407 (7)
C11	0.7899 (5)	0.5973 (4)	0.4390 (3)	0.0423 (7)
C12	0.9566 (5)	0.7653 (4)	0.4817 (4)	0.0494 (8)
H12A	0.9611	0.8282	0.4142	0.059*
C13	1.1206 (5)	0.8421 (4)	0.6277 (4)	0.0560 (9)
H13A	1.2317	0.9562	0.6562	0.067*
C14	1.1181 (5)	0.7516 (5)	0.7266 (4)	0.0536 (9)
H14A	1.2283	0.8041	0.8222	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0681 (16)	0.0792 (17)	0.0581 (15)	0.0486 (14)	0.0293 (12)	0.0251 (12)
O2	0.0783 (17)	0.0742 (17)	0.0564 (15)	0.0431 (14)	0.0243 (13)	0.0308 (13)
O3	0.0595 (16)	0.0526 (15)	0.0854 (19)	0.0114 (13)	0.0330 (14)	0.0078 (13)
N	0.0442 (15)	0.0521 (15)	0.0468 (15)	0.0266 (13)	0.0177 (12)	0.0061 (12)
C1	0.057 (2)	0.059 (2)	0.053 (2)	0.0252 (17)	0.0200 (16)	0.0039 (16)
C2	0.0468 (19)	0.068 (2)	0.055 (2)	0.0298 (17)	0.0112 (16)	0.0000 (17)
C3	0.0512 (19)	0.0525 (18)	0.0517 (19)	0.0341 (16)	0.0260 (15)	0.0161 (15)
C4	0.0480 (19)	0.0451 (18)	0.063 (2)	0.0226 (16)	0.0310 (16)	0.0069 (15)
C5	0.0514 (18)	0.0469 (17)	0.0566 (19)	0.0302 (15)	0.0327 (16)	0.0148 (15)
C6	0.078 (2)	0.056 (2)	0.075 (3)	0.0383 (19)	0.054 (2)	0.0285 (18)
C7	0.095 (3)	0.081 (3)	0.063 (2)	0.057 (2)	0.049 (2)	0.039 (2)
C8	0.073 (2)	0.081 (3)	0.051 (2)	0.052 (2)	0.0338 (18)	0.0238 (18)
C9	0.0469 (17)	0.0588 (19)	0.0434 (17)	0.0359 (16)	0.0232 (14)	0.0123 (14)
C10	0.0421 (16)	0.0460 (16)	0.0483 (17)	0.0291 (14)	0.0260 (14)	0.0120 (13)
C11	0.0455 (17)	0.0447 (16)	0.0463 (17)	0.0296 (14)	0.0214 (14)	0.0119 (13)
C12	0.0551 (19)	0.0443 (17)	0.062 (2)	0.0293 (15)	0.0328 (16)	0.0171 (15)
C13	0.0434 (18)	0.0478 (18)	0.068 (2)	0.0186 (15)	0.0238 (17)	0.0021 (17)
C14	0.0481 (18)	0.065 (2)	0.0490 (19)	0.0339 (17)	0.0190 (15)	0.0025 (16)

Geometric parameters (Å, º) top

O1—C1	1.403 (4)	C6—C7	1.391 (5)
O1—H1A	0.8200	C6—H6A	0.9300
O2—C3	1.216 (4)	C7—C8	1.366 (5)
O3—C4	1.214 (4)	C7—H7A	0.9300
N—C2	1.470 (4)	C8—C9	1.404 (5)
N—C3	1.383 (4)	C8—H8A	0.9300
N—C4	1.404 (4)	C9—C10	1.418 (4)
C1—C2	1.515 (5)	C9—C14	1.414 (5)
C1—H1B	0.9700	C10—C11	1.405 (4)
C1—H1C	0.9700	C11—C12	1.376 (4)
C2—H2A	0.9700	C12—C13	1.410 (5)
C2—H2B	0.9700	C12—H12A	0.9300
C3—C11	1.476 (4)	C13—C14	1.351 (5)
C4—C5	1.474 (5)	C13—H13A	0.9300
C5—C6	1.378 (5)	C14—H14A	0.9300
C5—C10	1.409 (4)

C1—O1—H1A	109.5	C5—C6—H6A	119.8
C3—N—C4	124.6 (3)	C7—C6—H6A	119.8
C3—N—C2	118.3 (3)	C8—C7—C6	120.9 (3)
C4—N—C2	117.1 (3)	C8—C7—H7A	119.6
O1—C1—C2	114.2 (3)	C6—C7—H7A	119.6
O1—C1—H1B	108.7	C7—C8—C9	120.4 (3)
C2—C1—H1B	108.7	C7—C8—H8A	119.8
O1—C1—H1C	108.7	C9—C8—H8A	119.8
C2—C1—H1C	108.7	C8—C9—C14	122.6 (3)
H1B—C1—H1C	107.6	C8—C9—C10	119.2 (3)
N—C2—C1	113.5 (3)	C14—C9—C10	118.2 (3)
N—C2—H2A	108.9	C11—C10—C5	120.9 (3)
C1—C2—H2A	108.9	C11—C10—C9	120.0 (3)
N—C2—H2B	108.9	C5—C10—C9	119.1 (3)
C1—C2—H2B	108.9	C12—C11—C10	119.9 (3)
H2A—C2—H2B	107.7	C12—C11—C3	120.0 (3)
O2—C3—N	120.7 (3)	C10—C11—C3	120.1 (3)
O2—C3—C11	121.9 (3)	C11—C12—C13	120.1 (3)
N—C3—C11	117.4 (3)	C11—C12—H12A	119.9
O3—C4—N	119.8 (3)	C13—C12—H12A	119.9
O3—C4—C5	123.0 (3)	C14—C13—C12	120.7 (3)
N—C4—C5	117.2 (3)	C14—C13—H13A	119.7
C6—C5—C10	120.1 (3)	C12—C13—H13A	119.7
C6—C5—C4	120.1 (3)	C13—C14—C9	121.1 (3)
C10—C5—C4	119.8 (3)	C13—C14—H14A	119.4
C5—C6—C7	120.4 (3)	C9—C14—H14A	119.4

C3—N—C2—C1	103.2 (4)	C4—C5—C10—C11	0.4 (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—O2	180.0 (3)	C8—C9—C10—C11	−178.6 (3)
C2—N—C3—O2	−1.4 (4)	C14—C9—C10—C11	1.9 (4)
C4—N—C3—C11	0.5 (4)	C8—C9—C10—C5	0.7 (4)
C2—N—C3—C11	179.1 (2)	C14—C9—C10—C5	−178.9 (2)
C3—N—C4—O3	179.1 (3)	C5—C10—C11—C12	179.1 (2)
C2—N—C4—O3	0.5 (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—C3	178.1 (2)
O3—C4—C5—C6	2.0 (5)	O2—C3—C11—C12	1.0 (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—C10	0.8 (4)	N—C3—C11—C10	0.7 (4)
C10—C5—C6—C7	0.1 (5)	C10—C11—C12—C13	0.2 (4)
C4—C5—C6—C7	178.5 (3)	C3—C11—C12—C13	−179.5 (3)
C5—C6—C7—C8	0.0 (5)	C11—C12—C13—C14	0.9 (4)
C6—C7—C8—C9	0.2 (5)	C12—C13—C14—C9	−0.6 (5)
C7—C8—C9—C14	178.9 (3)	C8—C9—C14—C13	179.7 (3)
C7—C8—C9—C10	−0.6 (5)	C10—C9—C14—C13	−0.8 (4)
C6—C5—C10—C11	178.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.82	1.97	2.771 (4)	165
C2—H2A···O2	0.97	2.31	2.714 (5)	104

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁NO₃
M_r	241.24
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.5480 (15), 8.8300 (18), 10.101 (2)
α, β, γ (°)	96.760 (19), 109.94 (3), 114.60 (3)
V (Å³)	548.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.970, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	2159, 1995, 1330
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.208, 1.00
No. of reflections	1995
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.31

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.82	1.97	2.771 (4)	165
C2—H2A···O2	0.97	2.31	2.714 (5)	104

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
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