N-(4-Chloro­phenyl)-1,8-naphthalimide

Jie, S.; Shao, S.

doi:10.1107/S1600536809020777

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1552

doi:10.1107/S1600536809020777

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N-(4-Chlorophenyl)-1,8-naphthalimide

Sun Jie ^a ^* and Shuai Shao ^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 18 May 2009; accepted 1 June 2009; online 13 June 2009)

In the title compound, C₁₈H₁₀ClNO₂, the naphthalimide ring system is almost planar, the rings forming dihedral angles of 2.05 (3), 2.26 (3) and 0.80 (3)°. The attached benzene ring of the 4-chlorophenyl substituent is inclined to the mean plane of the naphthalimide ring system by 75.77 (11)°. In the crystal structure, symmetry-related molecules are linked by C—H⋯O interactions. There are also weak π–π contacts between the naphthalimide rings [centroid–centroid distance = 3.732 (3) Å].

Related literature

For related literature on N-substituted 1,8-naphthalimides, see: De Souza et al. (2002 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₁₀ClNO₂
M_r = 307.72
Monoclinic, P 2₁ /n
a = 8.6800 (17) Å
b = 17.553 (4) Å
c = 9.4600 (19) Å
β = 103.53 (3)°
V = 1401.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.921, T_max = 0.946
2719 measured reflections
2549 independent reflections
1843 reflections with I > 2σ(I)
R_int = 0.048
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.157
S = 1.00
2549 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2ⁱ	0.93	2.45	3.138 (4)	131
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ); cell refinement: CAD-4 EXPRESS; 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: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020777/su2116sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020777/su2116Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies on N-substituted 1,8-naphthalimides (De Souza et al., 2002), we report herein on the crystal structure of the title compound.

In the title compound, illustrated in Fig. 1, the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (N/C4/C5/C7/C11/C13), B (C1—C6) and C (C5—C11) are oriented with respect to one another by dihedral angles of A/B = 2.05 (3), A/C = 2.26 (3) and B/C = 0.80 (3) °, hence almost coplanar. Rings A, B (C5—C10), C (C9—C14) and D (C12/C14—C18) are oriented at dihedral angles of A/D = 76.89 (3), B/D = 75.93 (3) and C/D = 75.19 (3) °.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into multimers (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 [symmetry codes: (i) –X,-Y,-Z, where Cg1 is centroid of ring C] with centroid-centroid distances of 3.732 (3) Å, may further stabilize the structure.

Related literature top

For related literature on N-substituted 1,8-naphthalimides, see: De Souza et al. (2002). For a description of the Cambridge Structural Database, see: Allen (2002). For hydrogen bonding, see: Bernstein et al. (1996).

Experimental top

For the preparation of the title compound: 1,8-naphthalic anhydride (1.98 g, 0.01 mol) and 2-aminoethanol (1.275 g,0.01 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 and 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 benzene as eluent gave a light-brown solution. Crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone solution (yield 94%; m.p. 489 K).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the C-H···O hydrogen bonded (dashed lines) molecules in the title compound.

N-(4-Chlorophenyl)-1,8-naphthalimide top

Crystal data top

C₁₈H₁₀ClNO₂	F(000) = 632
M_r = 307.72	D_x = 1.459 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 505 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.6800 (17) Å	Cell parameters from 25 reflections
b = 17.553 (4) Å	θ = 9–13°
c = 9.4600 (19) Å	µ = 0.28 mm⁻¹
β = 103.53 (3)°	T = 293 K
V = 1401.3 (5) Å³	Block, green
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1843 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 25.3°, θ_min = 2.3°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→21
T_min = 0.921, T_max = 0.946	l = −11→11
2719 measured reflections	3 standard reflections every 200 reflections
2549 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.07P)² + 1.5P] where P = (F_o² + 2F_c²)/3
2549 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₁₀ClNO₂	V = 1401.3 (5) Å³
M_r = 307.72	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.6800 (17) Å	µ = 0.28 mm⁻¹
b = 17.553 (4) Å	T = 293 K
c = 9.4600 (19) Å	0.30 × 0.20 × 0.20 mm
β = 103.53 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1843 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.048
T_min = 0.921, T_max = 0.946	3 standard reflections every 200 reflections
2719 measured reflections	intensity decay: 1%
2549 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.00	Δρ_max = 0.30 e Å⁻³
2549 reflections	Δρ_min = −0.23 e Å⁻³
199 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl	0.48706 (11)	0.18516 (6)	0.29044 (9)	0.0612 (3)
N	0.6288 (3)	0.39484 (14)	−0.1550 (2)	0.0381 (6)
O1	0.7353 (3)	0.48058 (14)	0.0210 (2)	0.0637 (7)
C1	0.8795 (5)	0.5908 (2)	−0.4218 (4)	0.0606 (10)
H1A	0.9182	0.6195	−0.4886	0.073*
O2	0.5248 (3)	0.30743 (13)	−0.3284 (2)	0.0555 (6)
C2	0.9122 (5)	0.6132 (2)	−0.2792 (4)	0.0705 (11)
H2A	0.9710	0.6572	−0.2507	0.085*
C3	0.8580 (4)	0.57040 (19)	−0.1762 (4)	0.0570 (9)
H3A	0.8824	0.5856	−0.0794	0.068*
C4	0.7693 (4)	0.50637 (17)	−0.2166 (3)	0.0413 (7)
C5	0.7317 (4)	0.48249 (17)	−0.3649 (3)	0.0385 (7)
C6	0.7888 (4)	0.52546 (18)	−0.4695 (3)	0.0459 (8)
C7	0.6412 (3)	0.41605 (17)	−0.4090 (3)	0.0373 (7)
C8	0.6044 (4)	0.3947 (2)	−0.5531 (3)	0.0498 (8)
H8A	0.5435	0.3514	−0.5818	0.060*
C9	0.6577 (4)	0.4375 (2)	−0.6567 (3)	0.0585 (10)
H9A	0.6311	0.4227	−0.7538	0.070*
C10	0.7487 (4)	0.5009 (2)	−0.6164 (4)	0.0541 (9)
H10A	0.7849	0.5284	−0.6863	0.065*
C11	0.7125 (4)	0.46182 (17)	−0.1071 (3)	0.0421 (7)
C12	0.5915 (4)	0.34481 (17)	−0.0448 (3)	0.0376 (7)
C13	0.5918 (4)	0.36798 (18)	−0.2992 (3)	0.0393 (7)
C14	0.7103 (4)	0.30126 (18)	0.0375 (3)	0.0442 (8)
H14A	0.8121	0.3040	0.0222	0.053*
C15	0.6788 (4)	0.25313 (19)	0.1435 (3)	0.0464 (8)
H15A	0.7592	0.2243	0.2014	0.056*
C16	0.5257 (4)	0.24902 (17)	0.1611 (3)	0.0406 (7)
C17	0.4056 (4)	0.29174 (19)	0.0787 (3)	0.0477 (8)
H17A	0.3029	0.2875	0.0915	0.057*
C18	0.4389 (4)	0.34117 (19)	−0.0239 (3)	0.0445 (7)
H18A	0.3595	0.3718	−0.0785	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0701 (6)	0.0711 (6)	0.0452 (5)	−0.0106 (5)	0.0189 (4)	0.0156 (4)
N	0.0516 (15)	0.0418 (14)	0.0203 (11)	−0.0043 (12)	0.0073 (10)	0.0008 (10)
O1	0.103 (2)	0.0626 (16)	0.0255 (11)	−0.0126 (14)	0.0140 (12)	−0.0104 (11)
C1	0.074 (2)	0.057 (2)	0.055 (2)	−0.0123 (19)	0.0224 (19)	0.0097 (17)
O2	0.0732 (16)	0.0572 (15)	0.0352 (12)	−0.0234 (13)	0.0107 (11)	−0.0085 (11)
C2	0.089 (3)	0.055 (2)	0.067 (3)	−0.022 (2)	0.017 (2)	−0.001 (2)
C3	0.075 (2)	0.047 (2)	0.0460 (19)	−0.0097 (18)	0.0081 (17)	−0.0038 (16)
C4	0.0537 (19)	0.0380 (17)	0.0310 (15)	−0.0019 (14)	0.0074 (13)	0.0002 (12)
C5	0.0443 (16)	0.0425 (17)	0.0282 (14)	0.0057 (13)	0.0073 (12)	0.0060 (12)
C6	0.0541 (19)	0.0453 (18)	0.0392 (17)	0.0081 (15)	0.0128 (14)	0.0128 (14)
C7	0.0448 (16)	0.0425 (17)	0.0244 (14)	0.0038 (13)	0.0079 (12)	0.0004 (12)
C8	0.066 (2)	0.057 (2)	0.0255 (15)	−0.0026 (17)	0.0088 (14)	−0.0026 (14)
C9	0.077 (3)	0.078 (3)	0.0226 (15)	0.002 (2)	0.0153 (15)	−0.0007 (16)
C10	0.066 (2)	0.061 (2)	0.0386 (17)	0.0044 (18)	0.0202 (16)	0.0125 (16)
C11	0.0581 (19)	0.0406 (17)	0.0260 (14)	−0.0014 (14)	0.0065 (13)	−0.0029 (12)
C12	0.0516 (18)	0.0420 (16)	0.0199 (13)	−0.0037 (14)	0.0099 (12)	−0.0026 (11)
C13	0.0484 (17)	0.0465 (18)	0.0219 (13)	−0.0011 (15)	0.0057 (12)	−0.0026 (12)
C14	0.0404 (16)	0.059 (2)	0.0346 (16)	0.0050 (15)	0.0117 (13)	0.0071 (14)
C15	0.0506 (19)	0.056 (2)	0.0323 (15)	0.0046 (15)	0.0080 (14)	0.0054 (14)
C16	0.0516 (18)	0.0461 (17)	0.0243 (14)	−0.0066 (14)	0.0094 (13)	−0.0001 (12)
C17	0.0428 (17)	0.064 (2)	0.0399 (17)	−0.0018 (16)	0.0164 (14)	−0.0010 (15)
C18	0.0435 (17)	0.0544 (19)	0.0346 (16)	0.0051 (14)	0.0070 (13)	0.0025 (14)

Geometric parameters (Å, º) top

Cl—C16	1.749 (3)	C7—C8	1.377 (4)
N—C11	1.401 (4)	C7—C13	1.477 (4)
N—C13	1.408 (3)	C8—C9	1.396 (5)
N—C12	1.457 (3)	C8—H8A	0.9300
O1—C11	1.226 (3)	C9—C10	1.367 (5)
C1—C2	1.370 (5)	C9—H9A	0.9300
C1—C6	1.404 (5)	C10—H10A	0.9300
C1—H1A	0.9300	C12—C14	1.370 (4)
O2—C13	1.212 (3)	C12—C18	1.386 (4)
C2—C3	1.396 (5)	C14—C15	1.386 (4)
C2—H2A	0.9300	C14—H14A	0.9300
C3—C4	1.365 (4)	C15—C16	1.379 (4)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.427 (4)	C16—C17	1.370 (4)
C4—C11	1.472 (4)	C17—C18	1.382 (4)
C5—C7	1.414 (4)	C17—H17A	0.9300
C5—C6	1.423 (4)	C18—H18A	0.9300
C6—C10	1.418 (5)

C11—N—C13	125.3 (2)	C8—C9—H9A	119.8
C11—N—C12	117.4 (2)	C9—C10—C6	120.9 (3)
C13—N—C12	117.0 (2)	C9—C10—H10A	119.5
C2—C1—C6	121.5 (3)	C6—C10—H10A	119.5
C2—C1—H1A	119.2	O1—C11—N	119.8 (3)
C6—C1—H1A	119.2	O1—C11—C4	123.3 (3)
C1—C2—C3	120.4 (4)	N—C11—C4	116.9 (2)
C1—C2—H2A	119.8	C14—C12—C18	120.7 (3)
C3—C2—H2A	119.8	C14—C12—N	118.6 (3)
C4—C3—C2	120.5 (3)	C18—C12—N	120.7 (3)
C4—C3—H3A	119.7	O2—C13—N	120.2 (3)
C2—C3—H3A	119.7	O2—C13—C7	122.9 (3)
C3—C4—C5	120.1 (3)	N—C13—C7	116.9 (3)
C3—C4—C11	120.0 (3)	C12—C14—C15	120.1 (3)
C5—C4—C11	119.9 (3)	C12—C14—H14A	120.0
C7—C5—C6	119.5 (3)	C15—C14—H14A	120.0
C7—C5—C4	121.1 (3)	C16—C15—C14	118.5 (3)
C6—C5—C4	119.4 (3)	C16—C15—H15A	120.7
C1—C6—C10	123.6 (3)	C14—C15—H15A	120.7
C1—C6—C5	118.0 (3)	C17—C16—C15	121.9 (3)
C10—C6—C5	118.4 (3)	C17—C16—Cl	120.3 (2)
C8—C7—C5	120.0 (3)	C15—C16—Cl	117.8 (2)
C8—C7—C13	120.2 (3)	C16—C17—C18	119.1 (3)
C5—C7—C13	119.8 (2)	C16—C17—H17A	120.4
C7—C8—C9	120.7 (3)	C18—C17—H17A	120.4
C7—C8—H8A	119.7	C17—C18—C12	119.6 (3)
C9—C8—H8A	119.7	C17—C18—H18A	120.2
C10—C9—C8	120.5 (3)	C12—C18—H18A	120.2
C10—C9—H9A	119.8

C6—C1—C2—C3	1.1 (6)	C12—N—C11—C4	171.5 (3)
C1—C2—C3—C4	−1.1 (6)	C3—C4—C11—O1	2.9 (5)
C2—C3—C4—C5	0.2 (5)	C5—C4—C11—O1	−177.2 (3)
C2—C3—C4—C11	−179.9 (4)	C3—C4—C11—N	−177.0 (3)
C3—C4—C5—C7	179.5 (3)	C5—C4—C11—N	2.9 (4)
C11—C4—C5—C7	−0.4 (4)	C11—N—C12—C14	−75.1 (4)
C3—C4—C5—C6	0.7 (5)	C13—N—C12—C14	98.6 (3)
C11—C4—C5—C6	−179.3 (3)	C11—N—C12—C18	105.1 (3)
C2—C1—C6—C10	178.5 (4)	C13—N—C12—C18	−81.2 (4)
C2—C1—C6—C5	−0.3 (5)	C11—N—C13—O2	176.7 (3)
C7—C5—C6—C1	−179.5 (3)	C12—N—C13—O2	3.6 (4)
C4—C5—C6—C1	−0.6 (5)	C11—N—C13—C7	−2.1 (4)
C7—C5—C6—C10	1.7 (4)	C12—N—C13—C7	−175.3 (3)
C4—C5—C6—C10	−179.5 (3)	C8—C7—C13—O2	3.4 (5)
C6—C5—C7—C8	−2.1 (4)	C5—C7—C13—O2	−174.2 (3)
C4—C5—C7—C8	179.1 (3)	C8—C7—C13—N	−177.8 (3)
C6—C5—C7—C13	175.4 (3)	C5—C7—C13—N	4.6 (4)
C4—C5—C7—C13	−3.4 (4)	C18—C12—C14—C15	−0.3 (5)
C5—C7—C8—C9	1.0 (5)	N—C12—C14—C15	179.9 (3)
C13—C7—C8—C9	−176.5 (3)	C12—C14—C15—C16	1.5 (5)
C7—C8—C9—C10	0.6 (5)	C14—C15—C16—C17	−0.9 (5)
C8—C9—C10—C6	−1.1 (5)	C14—C15—C16—Cl	177.5 (2)
C1—C6—C10—C9	−178.9 (3)	C15—C16—C17—C18	−0.9 (5)
C5—C6—C10—C9	−0.1 (5)	Cl—C16—C17—C18	−179.3 (2)
C13—N—C11—O1	178.5 (3)	C16—C17—C18—C12	2.1 (5)
C12—N—C11—O1	−8.4 (4)	C14—C12—C18—C17	−1.5 (5)
C13—N—C11—C4	−1.6 (4)	N—C12—C18—C17	178.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.93	2.45	3.138 (4)	131

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₀ClNO₂
M_r	307.72
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.6800 (17), 17.553 (4), 9.4600 (19)
β (°)	103.53 (3)
V (Å³)	1401.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.921, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	2719, 2549, 1843
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.157, 1.00
No. of reflections	2549
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.23

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.9300	2.4500	3.138 (4)	131.00

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

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

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