4,5,6,7-Tetra­chloro-2-(2-nitro­phen­yl)­isoindoline-1,3-dione

In the title compound, C₁₄H₄Cl₄N₂O₄, the tetra­chloro­phthalimide unit and the nitro­phenyl system are each essentially planar. The dihedral angle between the two planar systems is 74.6 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.031
• wR factor = 0.081
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Cl4    ..  O2      ..       2.96 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   N2      ..       5.33 su
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  O4      ..       3.13 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  O3      ..       3.13 Ang.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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). In this paper, the structure of the title compound, (I), is reported (Fig. 1). The geometry of molecule is close 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 essentially planar to within 0.019 (3) Å. The nitrophenyl system is planar to within 0.130 (2) Å. The dihedral angle between the nitrophenyl system and the tetrachlorophthalimide moiety is 74.6 (2) °. The crystal packing is shown in Fig. 2.

Related literature

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

S2. Experimental

A mixture of 4,5,6,7-tetrachloroisobenzofuran-1,3-dione (0.01 mol) and 2-nitrobenzenamine (0.01 mol) in acetic acid (10 ml) was refluxed for 1 h. After cooling, filtration and drying, the title compound was obtained: 10 mg was dissolved in 15 ml acetone, and the solution was kept at room temperature for 5 d. Natural evaporation gave colourless blocks of (I).

S3. Refinement

The H atoms were initially located from difference maps, relocated in idealized locations (C—H = 0.93 Å) and refined as riding with 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 (I), drawn with 30% probability ellipsoids (arbitrary spheres for the H atoms).
	Fig. 2. The crystal packing of (I), viewed along the a axis.

4,5,6,7-Tetrachloro-2-(2-nitrophenyl)isoindoline-1,3-dione

Crystal data

C14H4Cl4N2O4	Z = 2
Mr = 405.99	F(000) = 404
Triclinic, P1	Dx = 1.766 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4616 (13) Å	Cell parameters from 3012 reflections
b = 8.8220 (16) Å	θ = 2.6–28.1°
c = 13.137 (2) Å	µ = 0.80 mm^−1
α = 96.634 (2)°	T = 298 K
β = 100.513 (2)°	Block, colourless
γ = 113.368 (2)°	0.47 × 0.39 × 0.23 mm
V = 763.4 (2) Å^3

Data collection

Bruker SMART CCD diffractometer	2696 independent reflections
Radiation source: fine-focus sealed tube	2449 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
ω scans	θmax = 25.2°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→8
Tmin = 0.706, Tmax = 0.838	k = −4→10
3929 measured reflections	l = −15→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.2698P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2696 reflections	Δρmax = 0.22 e Å^−3
218 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.040 (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	0.9838 (3)	0.6036 (2)	0.22533 (15)	0.0360 (4)
C2	1.0988 (3)	0.6611 (2)	0.33922 (14)	0.0316 (4)
C3	1.1670 (3)	0.5754 (2)	0.40646 (14)	0.0316 (4)
C4	1.2641 (3)	0.6587 (2)	0.51150 (14)	0.0339 (4)
C5	1.2918 (3)	0.8239 (2)	0.54681 (14)	0.0341 (4)
C6	1.2243 (3)	0.9100 (2)	0.47778 (14)	0.0327 (4)
C7	1.1267 (3)	0.8255 (2)	0.37398 (14)	0.0318 (4)
C8	1.0350 (3)	0.8813 (2)	0.28396 (15)	0.0364 (4)
C9	0.8483 (3)	0.7423 (3)	0.09699 (15)	0.0427 (5)
C10	0.6529 (3)	0.7315 (3)	0.07728 (16)	0.0478 (5)
C11	0.5585 (4)	0.7370 (3)	−0.02208 (19)	0.0660 (7)
H11	0.4290	0.7314	−0.0350	0.079*
C12	0.6573 (5)	0.7509 (4)	−0.1017 (2)	0.0785 (9)
H12	0.5939	0.7545	−0.1687	0.094*
C13	0.8482 (5)	0.7596 (4)	−0.0834 (2)	0.0763 (8)
H13	0.9130	0.7677	−0.1380	0.092*
C14	0.9444 (4)	0.7563 (4)	0.01582 (18)	0.0631 (7)
H14	1.0746	0.7636	0.0282	0.076*
N1	0.9562 (3)	0.7438 (2)	0.19898 (12)	0.0402 (4)
N2	0.5378 (3)	0.7075 (3)	0.15888 (16)	0.0602 (5)
Cl4	1.12983 (7)	0.37220 (6)	0.36281 (4)	0.04150 (15)
Cl1	1.26252 (7)	1.11402 (6)	0.52014 (4)	0.04185 (15)
Cl3	1.35075 (7)	0.55691 (7)	0.59779 (4)	0.04516 (16)
Cl2	1.41129 (8)	0.92336 (7)	0.67612 (4)	0.04823 (16)
O1	0.9219 (2)	0.47001 (18)	0.16717 (11)	0.0514 (4)
O2	1.0246 (2)	1.01248 (18)	0.28003 (11)	0.0512 (4)
O3	0.5849 (3)	0.6509 (3)	0.23320 (15)	0.0761 (5)
O4	0.3974 (3)	0.7486 (3)	0.14666 (18)	0.0993 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0380 (10)	0.0380 (10)	0.0333 (9)	0.0207 (8)	0.0035 (8)	0.0049 (8)
C2	0.0306 (9)	0.0327 (9)	0.0318 (9)	0.0147 (7)	0.0059 (7)	0.0069 (7)
C3	0.0275 (8)	0.0313 (9)	0.0376 (9)	0.0138 (7)	0.0076 (7)	0.0094 (7)
C4	0.0291 (9)	0.0408 (10)	0.0350 (9)	0.0164 (8)	0.0079 (7)	0.0151 (8)
C5	0.0286 (9)	0.0405 (10)	0.0296 (9)	0.0126 (8)	0.0046 (7)	0.0061 (8)
C6	0.0305 (9)	0.0317 (9)	0.0349 (9)	0.0123 (7)	0.0084 (7)	0.0061 (7)
C7	0.0315 (9)	0.0312 (9)	0.0340 (9)	0.0144 (7)	0.0082 (7)	0.0081 (7)
C8	0.0394 (10)	0.0378 (10)	0.0344 (9)	0.0195 (8)	0.0077 (8)	0.0079 (8)
C9	0.0595 (12)	0.0428 (11)	0.0299 (9)	0.0313 (10)	0.0005 (8)	0.0052 (8)
C10	0.0558 (13)	0.0462 (12)	0.0381 (11)	0.0281 (10)	−0.0037 (9)	−0.0026 (9)
C11	0.0772 (17)	0.0692 (16)	0.0478 (14)	0.0455 (14)	−0.0167 (12)	−0.0032 (12)
C12	0.127 (3)	0.0765 (18)	0.0360 (13)	0.0619 (18)	−0.0110 (14)	0.0062 (12)
C13	0.121 (3)	0.093 (2)	0.0369 (12)	0.0662 (19)	0.0196 (14)	0.0191 (13)
C14	0.0818 (17)	0.0836 (18)	0.0425 (12)	0.0530 (15)	0.0159 (12)	0.0165 (12)
N1	0.0508 (10)	0.0407 (9)	0.0307 (8)	0.0266 (8)	−0.0006 (7)	0.0046 (7)
N2	0.0490 (11)	0.0656 (13)	0.0533 (12)	0.0240 (10)	−0.0020 (9)	−0.0097 (10)
Cl4	0.0489 (3)	0.0346 (3)	0.0455 (3)	0.0235 (2)	0.0085 (2)	0.0093 (2)
Cl1	0.0447 (3)	0.0329 (3)	0.0438 (3)	0.0157 (2)	0.0078 (2)	0.0011 (2)
Cl3	0.0470 (3)	0.0535 (3)	0.0412 (3)	0.0275 (2)	0.0053 (2)	0.0195 (2)
Cl2	0.0503 (3)	0.0544 (3)	0.0314 (3)	0.0204 (2)	−0.0014 (2)	0.0024 (2)
O1	0.0643 (9)	0.0439 (8)	0.0411 (8)	0.0296 (7)	−0.0053 (7)	−0.0036 (7)
O2	0.0761 (10)	0.0418 (8)	0.0413 (8)	0.0347 (8)	0.0055 (7)	0.0099 (6)
O3	0.0786 (13)	0.0913 (14)	0.0582 (11)	0.0339 (11)	0.0187 (9)	0.0210 (10)
O4	0.0677 (13)	0.147 (2)	0.0871 (15)	0.0661 (15)	0.0022 (11)	−0.0070 (15)

Geometric parameters (Å, º)

C1—O1	1.191 (2)	C8—N1	1.395 (2)
C1—N1	1.402 (2)	C9—C14	1.380 (3)
C1—C2	1.498 (2)	C9—C10	1.396 (3)
C2—C3	1.381 (2)	C9—N1	1.427 (2)
C2—C7	1.388 (3)	C10—C11	1.382 (3)
C3—C4	1.395 (3)	C10—N2	1.475 (3)
C3—Cl4	1.7115 (18)	C11—C12	1.376 (4)
C4—C5	1.397 (3)	C11—H11	0.9300
C4—Cl3	1.7136 (18)	C12—C13	1.370 (4)
C5—C6	1.396 (3)	C12—H12	0.9300
C5—Cl2	1.7124 (18)	C13—C14	1.378 (3)
C6—C7	1.385 (3)	C13—H13	0.9300
C6—Cl1	1.7130 (19)	C14—H14	0.9300
C7—C8	1.489 (3)	N2—O3	1.205 (3)
C8—O2	1.196 (2)	N2—O4	1.228 (3)
O1—C1—N1	125.26 (17)	C14—C9—C10	119.2 (2)
O1—C1—C2	130.10 (17)	C14—C9—N1	118.1 (2)
N1—C1—C2	104.62 (15)	C10—C9—N1	122.63 (19)
C3—C2—C7	121.50 (17)	C11—C10—C9	120.2 (2)
C3—C2—C1	130.08 (16)	C11—C10—N2	117.8 (2)
C7—C2—C1	108.39 (15)	C9—C10—N2	121.96 (18)
C2—C3—C4	117.91 (16)	C12—C11—C10	119.6 (3)
C2—C3—Cl4	121.00 (14)	C12—C11—H11	120.2
C4—C3—Cl4	121.08 (14)	C10—C11—H11	120.2
C3—C4—C5	120.73 (16)	C13—C12—C11	120.6 (2)
C3—C4—Cl3	119.49 (14)	C13—C12—H12	119.7
C5—C4—Cl3	119.78 (14)	C11—C12—H12	119.7
C6—C5—C4	120.85 (16)	C12—C13—C14	120.2 (3)
C6—C5—Cl2	119.28 (15)	C12—C13—H13	119.9
C4—C5—Cl2	119.88 (14)	C14—C13—H13	119.9
C7—C6—C5	117.85 (17)	C13—C14—C9	120.3 (3)
C7—C6—Cl1	121.17 (14)	C13—C14—H14	119.9
C5—C6—Cl1	120.98 (14)	C9—C14—H14	119.9
C6—C7—C2	121.16 (17)	C8—N1—C1	113.24 (15)
C6—C7—C8	130.23 (17)	C8—N1—C9	123.44 (16)
C2—C7—C8	108.60 (16)	C1—N1—C9	123.24 (16)
O2—C8—N1	124.59 (18)	O3—N2—O4	123.5 (3)
O2—C8—C7	130.28 (18)	O3—N2—C10	119.7 (2)
N1—C8—C7	105.12 (15)	O4—N2—C10	116.8 (2)
O1—C1—C2—C3	1.4 (4)	C6—C7—C8—N1	−179.26 (19)
N1—C1—C2—C3	179.82 (18)	C2—C7—C8—N1	0.0 (2)
O1—C1—C2—C7	−176.7 (2)	C14—C9—C10—C11	−0.8 (3)
N1—C1—C2—C7	1.8 (2)	N1—C9—C10—C11	177.6 (2)
C7—C2—C3—C4	0.5 (3)	C14—C9—C10—N2	176.8 (2)
C1—C2—C3—C4	−177.26 (18)	N1—C9—C10—N2	−4.8 (3)
C7—C2—C3—Cl4	179.48 (14)	C9—C10—C11—C12	0.9 (4)
C1—C2—C3—Cl4	1.7 (3)	N2—C10—C11—C12	−176.8 (2)
C2—C3—C4—C5	−0.3 (3)	C10—C11—C12—C13	−0.1 (4)
Cl4—C3—C4—C5	−179.26 (14)	C11—C12—C13—C14	−0.7 (4)
C2—C3—C4—Cl3	179.87 (13)	C12—C13—C14—C9	0.8 (4)
Cl4—C3—C4—Cl3	0.9 (2)	C10—C9—C14—C13	0.0 (4)
C3—C4—C5—C6	−0.4 (3)	N1—C9—C14—C13	−178.4 (2)
Cl3—C4—C5—C6	179.38 (14)	O2—C8—N1—C1	−178.3 (2)
C3—C4—C5—Cl2	179.95 (13)	C7—C8—N1—C1	1.3 (2)
Cl3—C4—C5—Cl2	−0.2 (2)	O2—C8—N1—C9	−1.6 (3)
C4—C5—C6—C7	0.9 (3)	C7—C8—N1—C9	177.93 (18)
Cl2—C5—C6—C7	−179.43 (13)	O1—C1—N1—C8	176.7 (2)
C4—C5—C6—Cl1	−178.69 (14)	C2—C1—N1—C8	−1.9 (2)
Cl2—C5—C6—Cl1	0.9 (2)	O1—C1—N1—C9	0.0 (3)
C5—C6—C7—C2	−0.7 (3)	C2—C1—N1—C9	−178.58 (18)
Cl1—C6—C7—C2	178.90 (14)	C14—C9—N1—C8	106.0 (2)
C5—C6—C7—C8	178.42 (18)	C10—C9—N1—C8	−72.4 (3)
Cl1—C6—C7—C8	−1.9 (3)	C14—C9—N1—C1	−77.6 (3)
C3—C2—C7—C6	0.0 (3)	C10—C9—N1—C1	103.9 (2)
C1—C2—C7—C6	178.22 (16)	C11—C10—N2—O3	157.2 (2)
C3—C2—C7—C8	−179.33 (16)	C9—C10—N2—O3	−20.5 (3)
C1—C2—C7—C8	−1.1 (2)	C11—C10—N2—O4	−23.3 (3)
C6—C7—C8—O2	0.3 (4)	C9—C10—N2—O4	159.0 (2)
C2—C7—C8—O2	179.5 (2)