N-(4-Chloro-phenyl)-1,8-naphthalimide.

In the title compound, C(18)H(10)ClNO(2), 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-chloro-phenyl substituent is inclined to the mean plane of the naphthalimide ring system by 75.77 (11)°. In the crystal structure, symmetry-related mol-ecules are linked by C-H⋯O inter-actions. 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 = 307.72

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.157

S = 1.00

2549 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

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.

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

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

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

C18H10ClNO2	F(000) = 632
Mr = 307.72	Dx = 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

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

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(Fo2) + (0.07P)2 + 1.5P] where P = (Fo2 + 2Fc2)/3
2549 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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
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*

	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)

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)

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

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) .