4,5,6,7-Tetra­chloro-2-(1-naphthyl)­iso­indole-1,3-dione acetone solvate

The phthal­imide and naphthalene moieties of the title compound, C₁₈H₇Cl₄NO₂·C₃H₆O, are oriented almost perpendicular to each other. The crystal structure is stabilized by weak π–π, C—H...π and van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.105
• Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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S1. Comment

N-Phthaloyl derivatization is one of the most frequently used methods of protection in synthesis involving compounds with primary amino group (Falck et al., 1995). Phthalimides have also served as starting materials and intermediates for the syntheses of alkaloids (Couture et al., 1998) and pharmacophores (Couture et al., 1997). They have cytotoxicity (Hall et al., 1995) and anti-HIV activity (van Derpoorten et al., 1997). In this paper, we report the structure of the title compound, (I).

The molecular structure of (I) is illustrated in Fig. 1. The isoindole moiety is planar with N1 deviating a maximum of 0.038 (2) Å and the naphthalene ring system is planar within ±0.012 (3) Å. The dihedral angle between these two planes [84.2 (1)°] shows that they are orthogonal. The bond lengths and angles in the phthalimide moiety are comparable to those reported for phthalimide (Ng, 1992). The C—Cl bond lengths are in the range 1.713 (2)–1.716 (2) Å, which are in agreement with the values reported in the literature (Busetti et al., 1980). In the solid state, the naphthalene ring system of the inversion-related (x, 1 − y, −z) molecules are stacked with partial overlap, such that the centroids of the benzene ring (C9–C13/C18) and its inversion equivalent are separated by 3.693 (2) Å. The crystal structure is further stabilized by weak C—H···π interactions (Table 2) ivolving the solvent molecule, Cl···O [Cl2···O3 = 3.152 (4) Å and Cl4···O1(x − 1, y − 1, z) = 3.250 (2) Å] short contacts and van der Waals forces (Fig. 2). In Table 2, Cg1, Cg2 and Cg3 denote the centroids of the benzene rings A (C2–C7), B (C9–C13/C18) and C (C13–C18), respectively.

S2. Experimental

A mixture of tetrachloraphthalic anhydride (10 mmol) and 1-naphthylamine (10 mmol) were refluxed in acetic acid (40 ml) until the disappearance of the starting materials as evidenced by thin-layer chromatography. After the reaction was complete, the yellow precipitate was filtered off and washed with a minimum amount of water to give the title compound (I). M.p. 551–552 K; IR (KBr): 1719.3 cm⁻¹ (C═O); ¹H NMR (CDCl₃, p.p.m.): 6.55–7.66 (m, 7 H); 20 mg of (I) was dissolved in 15 ml acetone and ether mixed solvent and the solution was kept at room temperature for 10 d to give colorless single crystals of (I) by slow evaporation.

S3. Refinement

H atoms were fixed geometrically and were treated as riding atoms on the parent C atoms with aromatic C—H = 0.93 Å and methyl C—H = 0.96 Å. The U_iso(H) values were set equal to 1.2U_eq of the carrier atom for the aromatic H atoms and at 1.5U_eq for the methyl H atoms.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids.
	Fig. 2. The molecular packing of (I), viewed down the a axis.

4,5,6,7-Tetrachloro-2-(naphthalen-1-yl)isoindole-1,3-dione acetone solvate

Crystal data

C18H7Cl4NO2·C3H6O	Z = 2
Mr = 469.12	F(000) = 476
Triclinic, P1	Dx = 1.535 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.706 (3) Å	Cell parameters from 899 reflections
b = 9.007 (3) Å	θ = 2.5–26.2°
c = 16.213 (6) Å	µ = 0.61 mm^−1
α = 94.985 (6)°	T = 293 K
β = 91.165 (6)°	Plate, colorless
γ = 114.879 (5)°	0.40 × 0.35 × 0.10 mm
V = 1015.0 (6) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3567 independent reflections
Radiation source: fine-focus sealed tube	2748 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ϕ and ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.784, Tmax = 0.941	k = −10→10
4239 measured reflections	l = −19→10

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.084P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.105	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.24 e Å^−3
3567 reflections	Δρmin = −0.33 e Å^−3
264 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.49679 (10)	0.76588 (8)	0.48951 (4)	0.0536 (2)
Cl2	0.31412 (11)	0.50661 (9)	0.61486 (4)	0.0544 (2)
Cl3	−0.03320 (11)	0.17536 (9)	0.55758 (4)	0.0573 (2)
Cl4	−0.19612 (10)	0.09529 (8)	0.37237 (4)	0.0558 (2)
O1	0.4191 (3)	0.7739 (2)	0.30108 (11)	0.0549 (5)
O2	−0.0896 (3)	0.2890 (3)	0.21518 (12)	0.0712 (6)
N1	0.1592 (3)	0.5473 (2)	0.23976 (12)	0.0462 (5)
C1	0.2910 (4)	0.6421 (3)	0.30486 (14)	0.0409 (6)
C2	0.2325 (3)	0.5428 (3)	0.37693 (14)	0.0372 (5)
C3	0.3078 (3)	0.5805 (3)	0.45807 (14)	0.0385 (6)
C4	0.2238 (4)	0.4645 (3)	0.51372 (14)	0.0398 (6)
C5	0.0683 (4)	0.3147 (3)	0.48757 (14)	0.0402 (6)
C6	−0.0059 (4)	0.2789 (3)	0.40504 (15)	0.0403 (6)
C7	0.0789 (3)	0.3952 (3)	0.35112 (14)	0.0384 (6)
C8	0.0309 (4)	0.3942 (3)	0.26106 (16)	0.0467 (6)
C9	0.1645 (4)	0.6001 (3)	0.15810 (15)	0.0466 (7)
C10	0.2875 (4)	0.5795 (4)	0.10489 (17)	0.0568 (7)
H10	0.3666	0.5311	0.1208	0.068*
C11	0.2946 (5)	0.6322 (4)	0.02529 (18)	0.0657 (9)
H11	0.3786	0.6183	−0.0117	0.079*
C12	0.1798 (5)	0.7029 (4)	0.00234 (18)	0.0641 (9)
H12	0.1863	0.7371	−0.0505	0.077*
C13	0.0511 (4)	0.7259 (3)	0.05631 (17)	0.0544 (7)
C14	−0.0696 (5)	0.8000 (4)	0.0337 (2)	0.0744 (10)
H14	−0.0657	0.8338	−0.0190	0.089*
C15	−0.1906 (6)	0.8227 (5)	0.0873 (3)	0.0851 (11)
H15	−0.2673	0.8733	0.0713	0.102*
C16	−0.2012 (5)	0.7703 (5)	0.1665 (2)	0.0798 (10)
H16	−0.2851	0.7858	0.2029	0.096*
C17	−0.0882 (4)	0.6962 (4)	0.19053 (19)	0.0626 (8)
H17	−0.0970	0.6613	0.2432	0.075*
C18	0.0402 (4)	0.6720 (3)	0.13719 (16)	0.0474 (7)
O3	0.5994 (5)	0.6625 (4)	0.7731 (2)	0.1259 (12)
C19	0.7113 (6)	0.9027 (4)	0.7079 (2)	0.0831 (11)
H19A	0.7192	0.8318	0.6618	0.125*
H19B	0.8375	0.9845	0.7258	0.125*
H19C	0.6331	0.9557	0.6913	0.125*
C20	0.6253 (5)	0.8046 (4)	0.7767 (2)	0.0684 (9)
C21	0.5669 (7)	0.8878 (6)	0.8460 (3)	0.1204 (18)
H21A	0.4947	0.9419	0.8243	0.181*
H21B	0.6789	0.9676	0.8777	0.181*
H21C	0.4892	0.8078	0.8810	0.181*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0539 (4)	0.0534 (4)	0.0449 (4)	0.0154 (3)	−0.0059 (3)	0.0018 (3)
Cl2	0.0648 (5)	0.0729 (5)	0.0335 (4)	0.0364 (4)	−0.0010 (3)	0.0104 (3)
Cl3	0.0759 (5)	0.0582 (4)	0.0467 (4)	0.0326 (4)	0.0164 (3)	0.0267 (3)
Cl4	0.0561 (4)	0.0444 (4)	0.0555 (4)	0.0084 (3)	0.0040 (3)	0.0152 (3)
O1	0.0572 (12)	0.0448 (11)	0.0464 (11)	0.0047 (10)	0.0012 (9)	0.0118 (8)
O2	0.0739 (15)	0.0580 (12)	0.0472 (12)	−0.0058 (11)	−0.0144 (10)	0.0117 (9)
N1	0.0529 (13)	0.0443 (12)	0.0331 (11)	0.0107 (10)	−0.0004 (9)	0.0144 (9)
C1	0.0434 (15)	0.0431 (14)	0.0355 (14)	0.0166 (12)	0.0025 (10)	0.0095 (10)
C2	0.0391 (14)	0.0404 (13)	0.0352 (13)	0.0189 (11)	0.0037 (10)	0.0083 (10)
C3	0.0387 (14)	0.0459 (14)	0.0354 (13)	0.0221 (12)	0.0023 (10)	0.0056 (10)
C4	0.0462 (15)	0.0522 (15)	0.0319 (13)	0.0305 (13)	0.0032 (10)	0.0094 (11)
C5	0.0480 (15)	0.0474 (14)	0.0374 (14)	0.0293 (13)	0.0101 (11)	0.0170 (11)
C6	0.0413 (14)	0.0404 (13)	0.0435 (15)	0.0202 (12)	0.0049 (11)	0.0099 (11)
C7	0.0397 (14)	0.0418 (14)	0.0368 (13)	0.0187 (12)	0.0040 (10)	0.0120 (10)
C8	0.0499 (16)	0.0441 (15)	0.0412 (15)	0.0137 (13)	0.0006 (12)	0.0126 (12)
C9	0.0527 (16)	0.0422 (14)	0.0324 (14)	0.0066 (13)	−0.0029 (11)	0.0119 (10)
C10	0.0613 (19)	0.0579 (17)	0.0459 (17)	0.0184 (15)	0.0046 (14)	0.0146 (13)
C11	0.073 (2)	0.068 (2)	0.0423 (17)	0.0146 (17)	0.0138 (15)	0.0124 (14)
C12	0.074 (2)	0.0605 (18)	0.0366 (16)	0.0059 (16)	−0.0028 (14)	0.0185 (13)
C13	0.0586 (18)	0.0445 (15)	0.0438 (16)	0.0044 (13)	−0.0084 (13)	0.0157 (12)
C14	0.080 (2)	0.064 (2)	0.069 (2)	0.0171 (18)	−0.0193 (18)	0.0287 (17)
C15	0.074 (3)	0.080 (2)	0.104 (3)	0.032 (2)	−0.013 (2)	0.030 (2)
C16	0.066 (2)	0.083 (2)	0.093 (3)	0.033 (2)	0.0063 (19)	0.017 (2)
C17	0.060 (2)	0.0660 (19)	0.0534 (18)	0.0169 (16)	−0.0002 (14)	0.0155 (14)
C18	0.0479 (16)	0.0405 (14)	0.0390 (14)	0.0034 (12)	−0.0041 (12)	0.0105 (11)
O3	0.171 (3)	0.092 (2)	0.128 (3)	0.064 (2)	−0.003 (2)	0.0416 (18)
C19	0.099 (3)	0.074 (2)	0.077 (2)	0.036 (2)	0.012 (2)	0.0149 (18)
C20	0.067 (2)	0.065 (2)	0.065 (2)	0.0207 (17)	−0.0143 (16)	0.0112 (16)
C21	0.109 (4)	0.122 (4)	0.079 (3)	0.000 (3)	0.024 (2)	0.005 (3)

Geometric parameters (Å, º)

Cl1—C3	1.716 (3)	C11—H11	0.93
Cl2—C4	1.715 (2)	C12—C13	1.403 (4)
Cl3—C5	1.713 (2)	C12—H12	0.93
Cl4—C6	1.715 (3)	C13—C14	1.412 (5)
O1—C1	1.190 (3)	C13—C18	1.429 (4)
O2—C8	1.192 (3)	C14—C15	1.352 (5)
N1—C1	1.394 (3)	C14—H14	0.93
N1—C8	1.396 (3)	C15—C16	1.399 (5)
N1—C9	1.441 (3)	C15—H15	0.93
C1—C2	1.494 (3)	C16—C17	1.369 (4)
C2—C7	1.379 (3)	C16—H16	0.93
C2—C3	1.381 (3)	C17—C18	1.399 (4)
C3—C4	1.394 (3)	C17—H17	0.93
C4—C5	1.398 (4)	O3—C20	1.206 (4)
C5—C6	1.400 (3)	C19—C20	1.474 (5)
C6—C7	1.376 (3)	C19—H19A	0.96
C7—C8	1.497 (3)	C19—H19B	0.96
C9—C10	1.353 (4)	C19—H19C	0.96
C9—C18	1.414 (4)	C20—C21	1.478 (5)
C10—C11	1.407 (4)	C21—H21A	0.96
C10—H10	0.93	C21—H21B	0.96
C11—C12	1.352 (5)	C21—H21C	0.96
C1—N1—C8	112.9 (2)	C11—C12—C13	121.6 (3)
C1—N1—C9	122.8 (2)	C11—C12—H12	119.2
C8—N1—C9	124.2 (2)	C13—C12—H12	119.2
O1—C1—N1	125.6 (2)	C12—C13—C14	122.5 (3)
O1—C1—C2	129.5 (2)	C12—C13—C18	119.1 (3)
N1—C1—C2	104.9 (2)	C14—C13—C18	118.4 (3)
C7—C2—C3	121.4 (2)	C15—C14—C13	121.4 (3)
C7—C2—C1	108.8 (2)	C15—C14—H14	119.3
C3—C2—C1	129.8 (2)	C13—C14—H14	119.3
C2—C3—C4	118.0 (2)	C14—C15—C16	120.3 (4)
C2—C3—Cl1	120.86 (19)	C14—C15—H15	119.8
C4—C3—Cl1	121.14 (19)	C16—C15—H15	119.8
C3—C4—C5	120.6 (2)	C17—C16—C15	120.2 (4)
C3—C4—Cl2	119.3 (2)	C17—C16—H16	119.9
C5—C4—Cl2	120.11 (18)	C15—C16—H16	119.9
C4—C5—C6	120.5 (2)	C16—C17—C18	121.2 (3)
C4—C5—Cl3	119.53 (18)	C16—C17—H17	119.4
C6—C5—Cl3	119.9 (2)	C18—C17—H17	119.4
C7—C6—C5	118.0 (2)	C17—C18—C9	124.5 (2)
C7—C6—Cl4	121.2 (2)	C17—C18—C13	118.6 (3)
C5—C6—Cl4	120.83 (18)	C9—C18—C13	116.9 (3)
C6—C7—C2	121.5 (2)	C20—C19—H19A	109.5
C6—C7—C8	130.4 (2)	C20—C19—H19B	109.5
C2—C7—C8	108.1 (2)	H19A—C19—H19B	109.5
O2—C8—N1	125.5 (2)	C20—C19—H19C	109.5
O2—C8—C7	129.4 (2)	H19A—C19—H19C	109.5
N1—C8—C7	105.1 (2)	H19B—C19—H19C	109.5
C10—C9—C18	122.8 (2)	O3—C20—C19	120.0 (4)
C10—C9—N1	119.1 (3)	O3—C20—C21	123.5 (4)
C18—C9—N1	118.2 (2)	C19—C20—C21	116.5 (3)
C9—C10—C11	119.4 (3)	C20—C21—H21A	109.5
C9—C10—H10	120.3	C20—C21—H21B	109.5
C11—C10—H10	120.3	H21A—C21—H21B	109.5
C12—C11—C10	120.3 (3)	C20—C21—H21C	109.5
C12—C11—H11	119.9	H21A—C21—H21C	109.5
C10—C11—H11	119.9	H21B—C21—H21C	109.5
C8—N1—C1—O1	176.8 (3)	C9—N1—C8—O2	−0.2 (5)
C9—N1—C1—O1	0.3 (4)	C1—N1—C8—C7	3.5 (3)
C8—N1—C1—C2	−3.8 (3)	C9—N1—C8—C7	−179.9 (2)
C9—N1—C1—C2	179.6 (2)	C6—C7—C8—O2	−2.4 (5)
O1—C1—C2—C7	−178.1 (3)	C2—C7—C8—O2	178.6 (3)
N1—C1—C2—C7	2.6 (3)	C6—C7—C8—N1	177.3 (3)
O1—C1—C2—C3	2.3 (5)	C2—C7—C8—N1	−1.7 (3)
N1—C1—C2—C3	−177.0 (2)	C1—N1—C9—C10	81.4 (3)
C7—C2—C3—C4	0.0 (3)	C8—N1—C9—C10	−94.8 (3)
C1—C2—C3—C4	179.5 (2)	C1—N1—C9—C18	−98.4 (3)
C7—C2—C3—Cl1	−179.10 (19)	C8—N1—C9—C18	85.5 (3)
C1—C2—C3—Cl1	0.4 (4)	C18—C9—C10—C11	0.4 (4)
C2—C3—C4—C5	0.2 (3)	N1—C9—C10—C11	−179.4 (2)
Cl1—C3—C4—C5	179.21 (18)	C9—C10—C11—C12	0.1 (4)
C2—C3—C4—Cl2	179.71 (18)	C10—C11—C12—C13	−0.1 (5)
Cl1—C3—C4—Cl2	−1.2 (3)	C11—C12—C13—C14	179.8 (3)
C3—C4—C5—C6	−0.2 (4)	C11—C12—C13—C18	−0.5 (4)
Cl2—C4—C5—C6	−179.71 (19)	C12—C13—C14—C15	−179.1 (3)
C3—C4—C5—Cl3	−179.45 (18)	C18—C13—C14—C15	1.1 (5)
Cl2—C4—C5—Cl3	1.0 (3)	C13—C14—C15—C16	−1.0 (6)
C4—C5—C6—C7	0.0 (4)	C14—C15—C16—C17	0.3 (6)
Cl3—C5—C6—C7	179.33 (19)	C15—C16—C17—C18	0.4 (5)
C4—C5—C6—Cl4	179.82 (19)	C16—C17—C18—C9	178.5 (3)
Cl3—C5—C6—Cl4	−0.9 (3)	C16—C17—C18—C13	−0.2 (4)
C5—C6—C7—C2	0.1 (4)	C10—C9—C18—C17	−179.6 (3)
Cl4—C6—C7—C2	−179.70 (19)	N1—C9—C18—C17	0.1 (4)
C5—C6—C7—C8	−178.9 (2)	C10—C9—C18—C13	−0.9 (4)
Cl4—C6—C7—C8	1.4 (4)	N1—C9—C18—C13	178.9 (2)
C3—C2—C7—C6	−0.1 (4)	C12—C13—C18—C17	179.8 (3)
C1—C2—C7—C6	−179.7 (2)	C14—C13—C18—C17	−0.5 (4)
C3—C2—C7—C8	179.1 (2)	C12—C13—C18—C9	0.9 (4)
C1—C2—C7—C8	−0.5 (3)	C14—C13—C18—C9	−179.3 (2)
C1—N1—C8—O2	−176.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···Cg1^i	0.96	3.21	4.101 (4)	156
C21—H21B···Cg2^ii	0.96	3.12	3.831 (5)	132
C21—H21B···Cg3^ii	0.96	3.05	3.913 (6)	151

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.