Tetra­chloro­isoindoline-1,3-dione N,N-dimethyl­formamide solvate

The crystal structure of the title compound, C₈HCl₄NO₂·C₃H₇NO, comprises tetra­chloro­isoindoline-1,3-dione and N,N-dimethyl­formamide (DMF) solvent mol­ecules, which are held together by N—H...O, C—H...O and C—H...Cl hydrogen bonds. The tetra­chloro­isoindoline-1,3-dione mol­ecule is essentially planar.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.046
• wR factor = 0.132
• Data-to-parameter ratio = 13.5

checkCIF/PLATON results

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Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.33
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N2
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O1      ..       3.12 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl4    ..  O2      ..       3.24 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   3 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
   1 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. Phthalimides have also served as starting materials and intermediates for the syntheses of alkaloids. In this paper, the structure of the title compound, (I), is reported.

The asymmetric unit of (I) (Fig. 1) consists one tetrachloroisoindoline-1,3-dione molecule and one DMF solvent molecule. The tetrachloroisoindoline-1,3-dione molecule is essentially planar, with an r.m.s.

deviation of 0.022 (2) Å from the mean plane for the non-H atoms. The DMF molecule is also planar, with an r.m.s. deviation of 0.007 (3) Å for the non-H

atoms (Fig. 2). The dihedral angle between the two molecules is 113.8 (2)°. The

geometric parameters of tetrachloroisoindoline-1,3-dione are similar to those in the compound N-methylphthalimide (Liang & Li, 2006).

The crystal structure of (I) is stabilized by N—H···O, C—H···O and C—H···Cl hydrogen bonds (Fig.2 and Table 1).

Related literature

For the structure of the related N-methylphthalimide, see Liang & Li (2006).

S2. Experimental

A mixture of tetrachloroisobenzofuran-1,3-dione (0.01 mol) and urea (0.01 mol) in acetic acid (10 ml) was refluxed for 5 h. After cooling, filtration and drying, the compound tetrachloroisoindoline-1,3-dione was obtained. This compound (10 mg) was dissolved in DMF (5 ml) and the solution was allowed to evaporate at room temperature. Colourless single crystals of (I) were formed after 20 d.

S3. Refinement

The H atoms were positioned geometrically, with C—H = 0.93–0.96 Å and N—H = 0.86 Å, and refined as riding, with U_iso(H) = 1.2U_eq(C,N) or 1.5U_eq(methyl 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; 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. Hydrogen bonds are indicated by dashed lines.

Tetrachloroisoindoline-1,3-dione N,N-dimethylformamide solvate

Crystal data

C8HCl4NO2·C3H7NO	Z = 2
Mr = 357.99	F(000) = 360
Triclinic, P1	Dx = 1.675 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6583 (16) Å	Cell parameters from 1410 reflections
b = 11.268 (3) Å	θ = 3.6–24.8°
c = 11.817 (3) Å	µ = 0.84 mm^−1
α = 73.244 (4)°	T = 294 K
β = 82.518 (5)°	Block, colourless
γ = 80.991 (5)°	0.26 × 0.20 × 0.12 mm
V = 709.6 (3) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2488 independent reflections
Radiation source: fine-focus sealed tube	1776 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −5→6
Tmin = 0.811, Tmax = 0.906	k = −9→13
3691 measured reflections	l = −14→13

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)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.062P)^2 + 0.5593P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2488 reflections	Δρmax = 0.98 e Å^−3
184 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (4)

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	1.31478 (18)	0.50354 (9)	0.38085 (9)	0.0521 (3)
Cl2	1.0432 (2)	0.53339 (11)	0.15763 (10)	0.0718 (4)
Cl3	0.6824 (2)	0.35207 (11)	0.16242 (9)	0.0616 (4)
Cl4	0.59312 (17)	0.13136 (9)	0.38830 (9)	0.0509 (3)
O1	1.3399 (6)	0.3021 (3)	0.6299 (3)	0.0657 (8)
O2	0.8175 (5)	0.0305 (3)	0.6327 (2)	0.0588 (8)
N1	1.0840 (6)	0.1529 (3)	0.6599 (3)	0.0494 (8)
H1	1.1143	0.1118	0.7310	0.059*
C1	1.1895 (7)	0.2577 (4)	0.5967 (3)	0.0458 (9)
C2	1.0819 (6)	0.3003 (3)	0.4800 (3)	0.0364 (8)
C3	1.1208 (6)	0.4000 (3)	0.3818 (3)	0.0402 (8)
C4	0.9965 (7)	0.4132 (3)	0.2833 (3)	0.0431 (9)
C5	0.8359 (6)	0.3311 (3)	0.2847 (3)	0.0411 (8)
C6	0.7955 (6)	0.2318 (3)	0.3850 (3)	0.0377 (8)
C7	0.9221 (6)	0.2174 (3)	0.4818 (3)	0.0352 (8)
C8	0.9253 (7)	0.1202 (3)	0.5982 (3)	0.0442 (9)
O3	0.2152 (6)	1.0015 (3)	0.8760 (3)	0.0703 (9)
N2	0.5006 (6)	0.8550 (3)	0.9699 (3)	0.0575 (9)
C9	0.4085 (11)	0.9480 (5)	0.8766 (5)	0.0736 (14)
H9	0.5104	0.9702	0.8076	0.088*
C10	0.3708 (13)	0.8099 (6)	1.0762 (5)	0.113 (2)
H10A	0.2469	0.8740	1.0905	0.170*
H10B	0.4755	0.7853	1.1390	0.170*
H10C	0.2993	0.7390	1.0736	0.170*
C11	0.7448 (11)	0.8044 (6)	0.9431 (7)	0.114 (2)
H11A	0.7946	0.8409	0.8611	0.171*
H11B	0.7545	0.7155	0.9579	0.171*
H11C	0.8480	0.8231	0.9923	0.171*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0567 (6)	0.0435 (6)	0.0610 (6)	−0.0187 (5)	−0.0079 (5)	−0.0144 (5)
Cl2	0.0916 (9)	0.0616 (7)	0.0538 (6)	−0.0304 (6)	−0.0212 (6)	0.0149 (5)
Cl3	0.0682 (7)	0.0733 (8)	0.0461 (6)	−0.0149 (6)	−0.0246 (5)	−0.0093 (5)
Cl4	0.0471 (6)	0.0533 (6)	0.0588 (6)	−0.0178 (4)	−0.0076 (4)	−0.0180 (5)
O1	0.076 (2)	0.070 (2)	0.0603 (18)	−0.0251 (16)	−0.0292 (15)	−0.0129 (15)
O2	0.0666 (19)	0.0518 (17)	0.0534 (17)	−0.0236 (15)	−0.0044 (14)	0.0008 (13)
N1	0.061 (2)	0.0493 (19)	0.0348 (16)	−0.0105 (16)	−0.0143 (15)	−0.0010 (14)
C1	0.050 (2)	0.044 (2)	0.045 (2)	−0.0022 (18)	−0.0114 (17)	−0.0134 (18)
C2	0.0383 (19)	0.0362 (19)	0.0366 (18)	−0.0049 (15)	−0.0053 (14)	−0.0119 (15)
C3	0.0393 (19)	0.0371 (19)	0.046 (2)	−0.0078 (15)	−0.0055 (16)	−0.0126 (16)
C4	0.049 (2)	0.038 (2)	0.0397 (19)	−0.0062 (17)	−0.0082 (16)	−0.0039 (16)
C5	0.043 (2)	0.044 (2)	0.0376 (19)	−0.0048 (16)	−0.0119 (16)	−0.0098 (16)
C6	0.0347 (18)	0.0374 (19)	0.0434 (19)	−0.0056 (15)	−0.0043 (15)	−0.0139 (16)
C7	0.0366 (19)	0.0325 (18)	0.0356 (18)	−0.0022 (15)	−0.0041 (14)	−0.0088 (14)
C8	0.048 (2)	0.039 (2)	0.043 (2)	−0.0036 (18)	−0.0070 (17)	−0.0070 (17)
O3	0.070 (2)	0.076 (2)	0.0573 (19)	0.0034 (18)	−0.0231 (16)	−0.0056 (16)
N2	0.058 (2)	0.052 (2)	0.067 (2)	−0.0059 (17)	−0.0295 (18)	−0.0125 (18)
C9	0.085 (4)	0.080 (4)	0.068 (3)	−0.028 (3)	−0.012 (3)	−0.029 (3)
C10	0.147 (6)	0.119 (5)	0.082 (4)	−0.084 (5)	−0.019 (4)	−0.001 (4)
C11	0.081 (4)	0.102 (5)	0.175 (7)	0.001 (4)	−0.023 (4)	−0.067 (5)

Geometric parameters (Å, º)

Cl1—C3	1.719 (4)	C5—C6	1.398 (5)
Cl2—C4	1.720 (4)	C6—C7	1.385 (5)
Cl3—C5	1.722 (3)	C7—C8	1.491 (5)
Cl4—C6	1.721 (4)	O3—C9	1.163 (6)
O1—C1	1.208 (5)	N2—C10	1.373 (7)
O2—C8	1.205 (5)	N2—C9	1.378 (6)
N1—C8	1.379 (5)	N2—C11	1.441 (6)
N1—C1	1.380 (5)	C9—H9	0.9300
N1—H1	0.8600	C10—H10A	0.9600
C1—C2	1.500 (5)	C10—H10B	0.9600
C2—C3	1.385 (5)	C10—H10C	0.9600
C2—C7	1.392 (5)	C11—H11A	0.9600
C3—C4	1.397 (5)	C11—H11B	0.9600
C4—C5	1.390 (5)	C11—H11C	0.9600
C8—N1—C1	113.8 (3)	C2—C7—C8	108.2 (3)
C8—N1—H1	123.1	O2—C8—N1	126.2 (3)
C1—N1—H1	123.1	O2—C8—C7	128.6 (3)
O1—C1—N1	126.2 (3)	N1—C8—C7	105.2 (3)
O1—C1—C2	128.6 (4)	C10—N2—C9	123.8 (5)
N1—C1—C2	105.2 (3)	C10—N2—C11	122.8 (5)
C3—C2—C7	121.5 (3)	C9—N2—C11	113.3 (5)
C3—C2—C1	130.9 (3)	O3—C9—N2	126.1 (5)
C7—C2—C1	107.5 (3)	O3—C9—H9	116.9
C2—C3—C4	117.4 (3)	N2—C9—H9	116.9
C2—C3—Cl1	121.3 (3)	N2—C10—H10A	109.5
C4—C3—Cl1	121.2 (3)	N2—C10—H10B	109.5
C5—C4—C3	121.3 (3)	H10A—C10—H10B	109.5
C5—C4—Cl2	119.3 (3)	N2—C10—H10C	109.5
C3—C4—Cl2	119.4 (3)	H10A—C10—H10C	109.5
C4—C5—C6	120.7 (3)	H10B—C10—H10C	109.5
C4—C5—Cl3	119.9 (3)	N2—C11—H11A	109.5
C6—C5—Cl3	119.3 (3)	N2—C11—H11B	109.5
C7—C6—C5	117.9 (3)	H11A—C11—H11B	109.5
C7—C6—Cl4	121.2 (3)	N2—C11—H11C	109.5
C5—C6—Cl4	121.0 (3)	H11A—C11—H11C	109.5
C6—C7—C2	121.1 (3)	H11B—C11—H11C	109.5
C6—C7—C8	130.7 (3)
C8—N1—C1—O1	−177.3 (4)	Cl3—C5—C6—C7	179.9 (3)
C8—N1—C1—C2	1.4 (4)	C4—C5—C6—Cl4	178.9 (3)
O1—C1—C2—C3	−1.1 (7)	Cl3—C5—C6—Cl4	−0.6 (4)
N1—C1—C2—C3	−179.7 (3)	C5—C6—C7—C2	0.9 (5)
O1—C1—C2—C7	178.2 (4)	Cl4—C6—C7—C2	−178.6 (3)
N1—C1—C2—C7	−0.5 (4)	C5—C6—C7—C8	−177.7 (3)
C7—C2—C3—C4	−1.1 (5)	Cl4—C6—C7—C8	2.8 (5)
C1—C2—C3—C4	178.0 (4)	C3—C2—C7—C6	0.0 (5)
C7—C2—C3—Cl1	179.0 (3)	C1—C2—C7—C6	−179.3 (3)
C1—C2—C3—Cl1	−1.9 (5)	C3—C2—C7—C8	178.9 (3)
C2—C3—C4—C5	1.4 (5)	C1—C2—C7—C8	−0.5 (4)
Cl1—C3—C4—C5	−178.7 (3)	C1—N1—C8—O2	177.4 (4)
C2—C3—C4—Cl2	−178.5 (3)	C1—N1—C8—C7	−1.6 (4)
Cl1—C3—C4—Cl2	1.4 (4)	C6—C7—C8—O2	1.0 (7)
C3—C4—C5—C6	−0.5 (6)	C2—C7—C8—O2	−177.7 (4)
Cl2—C4—C5—C6	179.4 (3)	C6—C7—C8—N1	180.0 (3)
C3—C4—C5—Cl3	178.9 (3)	C2—C7—C8—N1	1.2 (4)
Cl2—C4—C5—Cl3	−1.2 (5)	C10—N2—C9—O3	1.7 (7)
C4—C5—C6—C7	−0.6 (5)	C11—N2—C9—O3	178.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3^i	0.86	1.90	2.752 (4)	170
C9—H9···O2^ii	0.93	2.53	3.452 (6)	175

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