4,5,6,7-Tetra­chloro-2-phenyl­isoindoline-1,3-dione

In the title compound, C₁₄H₅Cl₄NO₂, the tetra­chloro­phthalimide group is planar to within 0.037 (3) Å and forms a dihedral angle of 61.6 (2)° with the phenyl substituent.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.117
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl2    ..  O2      ..       2.93 Ang.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C11
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C9     -C14           1.37 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O1      ..       3.14 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Phthalimides and N-substituted phthalimides are an important class of compounds because of their interesting biological activities (Lima et al., 2002). The molecular structure of the title compound (Figure 1) is similar to the related compounds 2-(2-hydroxyphenyl)isoindoline-1,3-dione (Li et al., 2007) and 2-(4-hydroxyphenyl)isoindoline-1,3-dione (Liang & Li, 2006). The tetrachlorophthalimide moiety system is planar to within 0.037 (3) Å. The dihedral angle between the phenyl ring and the tetrachlorophthalimide moiety is 61.6 (2) °.

Related literature

For related literature, see: Liang & Li (2006); Li et al. (2007); Lima et al. (2002).

S2. Experimental

A mixture of 4,5,6,7-tetrachloroisobenzofuran-1,3-dione (0.01 mol) and aniline (0.01 mol) in acetic acid (10 ml) was refluxed for 1 h. After cooling, filtration and drying, the title compound was obtained. Single crystals suitable for X-ray analysis were obtained by slow evaporation from a solution of 10 mg in 15 ml acetone.

S3. Refinement

H atoms were visible in difference Fourier maps but were placed geometrically and refined using a riding model with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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 molecular structure of the title compound with displacement ellipsoids drawn at 30% probability for non-H atoms.
	Fig. 2. Packing of the title compound viewed along the b axis.

4,5,6,7-Tetrachloro-2-phenylisoindoline-1,3-dione

Crystal data

C14H5Cl4NO2	F(000) = 1440
Mr = 360.99	Dx = 1.696 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4222 reflections
a = 16.854 (5) Å	θ = 2.4–27.3°
b = 6.780 (2) Å	µ = 0.84 mm^−1
c = 24.749 (8) Å	T = 298 K
V = 2828.0 (15) Å^3	Plate, colourless
Z = 8	0.49 × 0.42 × 0.01 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2484 independent reflections
Radiation source: fine-focus sealed tube	2131 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −19→20
Tmin = 0.684, Tmax = 0.992	k = −7→8
11041 measured reflections	l = −17→29

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.07P)^2 + 0.5952P] where P = (Fo^2 + 2Fc^2)/3
2484 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.38 e Å^−3

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
C1	0.70198 (16)	−0.0160 (3)	0.79596 (10)	0.0354 (6)
C2	0.67110 (14)	0.0075 (3)	0.73988 (10)	0.0316 (5)
C3	0.71096 (15)	0.0256 (3)	0.69145 (10)	0.0328 (6)
C4	0.66528 (16)	0.0442 (3)	0.64456 (10)	0.0344 (6)
C5	0.58288 (16)	0.0397 (3)	0.64655 (10)	0.0366 (6)
C6	0.54312 (15)	0.0189 (3)	0.69589 (10)	0.0336 (6)
C7	0.58916 (15)	0.0068 (3)	0.74209 (10)	0.0316 (5)
C8	0.56418 (16)	−0.0068 (3)	0.79972 (10)	0.0356 (6)
C9	0.63664 (15)	−0.0407 (4)	0.88692 (10)	0.0405 (6)
C10	0.6026 (2)	0.1018 (6)	0.91814 (13)	0.0715 (10)
H10	0.5814	0.2148	0.9025	0.086*
C11	0.6002 (3)	0.0752 (7)	0.97342 (15)	0.0969 (15)
H11	0.5767	0.1708	0.9951	0.116*
C12	0.6312 (2)	−0.0859 (8)	0.99626 (14)	0.0886 (15)
H12	0.6286	−0.1027	1.0335	0.106*
C13	0.6665 (2)	−0.2253 (7)	0.96492 (13)	0.0807 (11)
H13	0.6891	−0.3358	0.9810	0.097*
C14	0.66904 (18)	−0.2043 (5)	0.90959 (11)	0.0576 (8)
H14	0.6925	−0.3005	0.8881	0.069*
Cl1	0.81288 (4)	0.02580 (9)	0.68847 (3)	0.0411 (2)
Cl2	0.44169 (4)	0.00610 (9)	0.69857 (3)	0.0426 (2)
Cl3	0.71186 (5)	0.07602 (11)	0.58370 (3)	0.0524 (2)
Cl4	0.52839 (5)	0.06222 (12)	0.58853 (3)	0.0583 (3)
N1	0.63480 (12)	−0.0189 (3)	0.82904 (8)	0.0355 (5)
O1	0.49834 (11)	−0.0061 (3)	0.81870 (8)	0.0469 (5)
O2	0.76928 (11)	−0.0317 (3)	0.81109 (8)	0.0506 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0304 (14)	0.0362 (13)	0.0395 (14)	−0.0002 (10)	0.0002 (10)	−0.0060 (10)
C2	0.0314 (13)	0.0274 (11)	0.0360 (13)	0.0001 (9)	0.0016 (10)	−0.0046 (9)
C3	0.0324 (14)	0.0257 (11)	0.0402 (13)	−0.0033 (9)	0.0063 (10)	−0.0039 (9)
C4	0.0430 (15)	0.0268 (11)	0.0334 (13)	−0.0027 (10)	0.0068 (10)	−0.0013 (9)
C5	0.0436 (15)	0.0328 (12)	0.0333 (13)	−0.0025 (10)	−0.0010 (11)	0.0017 (10)
C6	0.0306 (13)	0.0349 (12)	0.0352 (13)	−0.0003 (10)	−0.0012 (10)	0.0016 (10)
C7	0.0323 (13)	0.0288 (11)	0.0337 (13)	0.0002 (10)	0.0022 (10)	−0.0016 (9)
C8	0.0328 (14)	0.0376 (14)	0.0365 (14)	0.0017 (10)	0.0006 (10)	−0.0011 (10)
C9	0.0327 (14)	0.0577 (16)	0.0311 (14)	0.0015 (11)	−0.0026 (10)	−0.0010 (12)
C10	0.080 (2)	0.087 (3)	0.0481 (19)	0.030 (2)	−0.0025 (16)	−0.0151 (17)
C11	0.089 (3)	0.153 (4)	0.049 (2)	0.035 (3)	0.0008 (19)	−0.036 (2)
C12	0.056 (2)	0.178 (5)	0.0313 (17)	−0.003 (2)	−0.0056 (15)	0.001 (2)
C13	0.074 (2)	0.118 (3)	0.050 (2)	0.007 (2)	−0.0165 (18)	0.023 (2)
C14	0.0558 (19)	0.073 (2)	0.0437 (16)	0.0088 (16)	−0.0079 (13)	0.0015 (15)
Cl1	0.0323 (4)	0.0385 (4)	0.0525 (4)	−0.0027 (2)	0.0088 (3)	−0.0040 (3)
Cl2	0.0297 (4)	0.0531 (4)	0.0449 (4)	−0.0008 (3)	−0.0031 (3)	0.0048 (3)
Cl3	0.0569 (5)	0.0617 (5)	0.0385 (4)	−0.0062 (3)	0.0141 (3)	0.0020 (3)
Cl4	0.0550 (5)	0.0834 (6)	0.0366 (4)	−0.0083 (4)	−0.0076 (3)	0.0101 (3)
N1	0.0315 (12)	0.0448 (12)	0.0303 (11)	0.0007 (8)	0.0001 (8)	−0.0016 (9)
O1	0.0303 (11)	0.0689 (12)	0.0416 (10)	0.0014 (8)	0.0054 (8)	0.0026 (9)
O2	0.0302 (11)	0.0744 (13)	0.0472 (11)	0.0012 (9)	−0.0033 (8)	−0.0032 (9)

Geometric parameters (Å, º)

C1—O2	1.199 (3)	C8—O1	1.205 (3)
C1—N1	1.398 (3)	C8—N1	1.396 (3)
C1—C2	1.491 (4)	C9—C14	1.358 (4)
C2—C3	1.379 (3)	C9—C10	1.364 (4)
C2—C7	1.382 (4)	C9—N1	1.440 (3)
C3—C4	1.398 (4)	C10—C11	1.381 (5)
C3—Cl1	1.719 (3)	C10—H10	0.930
C4—C5	1.390 (4)	C11—C12	1.336 (6)
C4—Cl3	1.712 (2)	C11—H11	0.930
C5—C6	1.400 (4)	C12—C13	1.360 (5)
C5—Cl4	1.711 (3)	C12—H12	0.930
C6—C7	1.384 (4)	C13—C14	1.377 (4)
C6—Cl2	1.713 (3)	C13—H13	0.930
C7—C8	1.490 (3)	C14—H14	0.930
O2—C1—N1	125.6 (2)	N1—C8—C7	105.1 (2)
O2—C1—C2	129.1 (2)	C14—C9—C10	120.9 (3)
N1—C1—C2	105.3 (2)	C14—C9—N1	120.2 (2)
C3—C2—C7	121.4 (2)	C10—C9—N1	118.8 (3)
C3—C2—C1	130.4 (2)	C9—C10—C11	118.8 (3)
C7—C2—C1	108.2 (2)	C9—C10—H10	120.6
C2—C3—C4	117.5 (2)	C11—C10—H10	120.6
C2—C3—Cl1	121.6 (2)	C12—C11—C10	121.0 (4)
C4—C3—Cl1	120.96 (19)	C12—C11—H11	119.5
C5—C4—C3	121.2 (2)	C10—C11—H11	119.5
C5—C4—Cl3	119.49 (18)	C11—C12—C13	119.9 (3)
C3—C4—Cl3	119.3 (2)	C11—C12—H12	120.1
C4—C5—C6	120.8 (2)	C13—C12—H12	120.1
C4—C5—Cl4	120.29 (18)	C12—C13—C14	120.6 (4)
C6—C5—Cl4	118.9 (2)	C12—C13—H13	119.7
C7—C6—C5	117.3 (2)	C14—C13—H13	119.7
C7—C6—Cl2	121.64 (19)	C9—C14—C13	118.9 (3)
C5—C6—Cl2	121.1 (2)	C9—C14—H14	120.6
C2—C7—C6	121.8 (2)	C13—C14—H14	120.6
C2—C7—C8	108.7 (2)	C8—N1—C1	112.7 (2)
C6—C7—C8	129.5 (2)	C8—N1—C9	122.8 (2)
O1—C8—N1	125.6 (2)	C1—N1—C9	124.5 (2)
O1—C8—C7	129.3 (2)
O2—C1—C2—C3	−3.1 (4)	C5—C6—C7—C8	177.0 (2)
N1—C1—C2—C3	177.6 (2)	Cl2—C6—C7—C8	−3.7 (3)
O2—C1—C2—C7	176.2 (2)	C2—C7—C8—O1	177.8 (2)
N1—C1—C2—C7	−3.1 (2)	C6—C7—C8—O1	−1.7 (4)
C7—C2—C3—C4	0.3 (3)	C2—C7—C8—N1	−1.5 (2)
C1—C2—C3—C4	179.5 (2)	C6—C7—C8—N1	178.9 (2)
C7—C2—C3—Cl1	−179.80 (16)	C14—C9—C10—C11	−1.2 (5)
C1—C2—C3—Cl1	−0.6 (3)	N1—C9—C10—C11	176.2 (3)
C2—C3—C4—C5	−1.5 (3)	C9—C10—C11—C12	0.6 (7)
Cl1—C3—C4—C5	178.53 (17)	C10—C11—C12—C13	0.8 (7)
C2—C3—C4—Cl3	177.68 (17)	C11—C12—C13—C14	−1.5 (6)
Cl1—C3—C4—Cl3	−2.3 (3)	C10—C9—C14—C13	0.5 (5)
C3—C4—C5—C6	0.8 (3)	N1—C9—C14—C13	−176.9 (3)
Cl3—C4—C5—C6	−178.38 (18)	C12—C13—C14—C9	0.9 (5)
C3—C4—C5—Cl4	−179.87 (18)	O1—C8—N1—C1	−179.9 (2)
Cl3—C4—C5—Cl4	0.9 (3)	C7—C8—N1—C1	−0.5 (3)
C4—C5—C6—C7	1.1 (3)	O1—C8—N1—C9	2.7 (4)
Cl4—C5—C6—C7	−178.17 (17)	C7—C8—N1—C9	−178.0 (2)
C4—C5—C6—Cl2	−178.12 (16)	O2—C1—N1—C8	−177.1 (2)
Cl4—C5—C6—Cl2	2.6 (3)	C2—C1—N1—C8	2.2 (3)
C3—C2—C7—C6	1.8 (3)	O2—C1—N1—C9	0.3 (4)
C1—C2—C7—C6	−177.6 (2)	C2—C1—N1—C9	179.6 (2)
C3—C2—C7—C8	−177.8 (2)	C14—C9—N1—C8	117.3 (3)
C1—C2—C7—C8	2.8 (2)	C10—C9—N1—C8	−60.2 (4)
C5—C6—C7—C2	−2.4 (3)	C14—C9—N1—C1	−59.9 (4)
Cl2—C6—C7—C2	176.82 (16)	C10—C9—N1—C1	122.7 (3)