4,5,6,7-Tetra­chloro-2-hydroxy­iso­indoline-1,3-dione N,N-dimethyl­formamide solvate

In the title compound, C₈HCl₄NO₃·C₃H₇NO, the crystal packing is consolidated by O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.035
• wR factor = 0.095
• Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N2
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C11
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  O2      ..       3.08 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  O1      ..       3.09 Ang.

   0 ALERT level A = In general: serious problem
   0 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
   2 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
   2 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. The asymmetric unit of (I) contains one 4,5,6,7-Tetrachloro-2-hydroxylisoindoline-1,3-dione molecule and one DMF molecule (Fig. 1). The bond lengths and angles agree with those in those similar compounds 4-phthalimidobenzoic acid N,N-dimethylformamide solvate (Liang et al., 2006) and 4-(5-bromo-1,3-dioxoisoindolin-2-yl)benzoic acid N,N-dimethylformamide solvate (Liang et al., 2007). 4,5,6,7-tetrachloro-2-hydroxylisoindoline-1,3-dione molecule and DMF molecule are planar, within 0.024 (2) Å and 0.019 (2) Å for all non-H atoms, respectively. The dihedral angle between them is 70.6 (2) °. The crystal structure is stabilized by an O—H···O hydrogen bond which connects the benzoic acid and DMF molecules (Fig. 2 and Table 1).

Related literature

For related structures, see: Liang et al. (2006, 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 hydroxyamine hydrochloride (0.01 mol) in acetic acid (10 ml) was refluxed for 1 h. After cooling, filtration and drying, 4,5,6,7-tetrachloro-2-hydroxylisoindoline-1,3-dione was obtained. 10 mg of this compound were dissolved in DMF (5 ml), and the solution was kept at room temperature for 10 d. Natural evaporation gave colourless slabls of (I).

S3. Refinement

The H atoms were initially located from difference maps, then relocated in idealized locations (C—H = 0.93–0.96 Å, O—H = 0.82 Å) and refined as riding with U_iso(H) = 1.2U_eq(carrier) or 1.5U_eq(O, 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 (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. Hydrogen bonds are indicated by dashed lines.

4,5,6,7-Tetrachloro-2-hydroxyisoindoline-1,3-dione N,N-dimethylformamide solvate

Crystal data

C8HCl4NO3·C3H7NO	F(000) = 1504
Mr = 373.99	Dx = 1.721 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4163 reflections
a = 16.885 (2) Å	θ = 2.4–27.1°
b = 7.7823 (11) Å	µ = 0.84 mm^−1
c = 21.974 (3) Å	T = 298 K
V = 2887.5 (7) Å^3	Slab, colourless
Z = 8	0.45 × 0.38 × 0.14 mm

Data collection

Bruker SMART CCD diffractometer	2550 independent reflections
Radiation source: fine-focus sealed tube	2127 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −20→15
Tmin = 0.705, Tmax = 0.892	k = −9→8
11352 measured reflections	l = −19→26

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0519P)^2 + 0.936P] where P = (Fo^2 + 2Fc^2)/3
2550 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.17 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	0.20622 (14)	0.3474 (3)	0.45063 (10)	0.0411 (5)
C2	0.17868 (11)	0.2593 (3)	0.50706 (9)	0.0347 (5)
C3	0.22109 (12)	0.1868 (2)	0.55376 (9)	0.0350 (5)
C4	0.17926 (12)	0.1107 (3)	0.60146 (9)	0.0348 (5)
C5	0.09689 (12)	0.1052 (3)	0.60049 (9)	0.0361 (5)
C6	0.05419 (12)	0.1804 (3)	0.55290 (9)	0.0366 (5)
C7	0.09632 (11)	0.2569 (3)	0.50683 (9)	0.0360 (5)
C8	0.06792 (14)	0.3430 (3)	0.45026 (10)	0.0431 (5)
C9	0.42878 (16)	0.0147 (4)	0.70928 (12)	0.0624 (7)
H9A	0.4798	0.0639	0.7176	0.094*
H9B	0.4053	0.0722	0.6751	0.094*
H9C	0.4347	−0.1052	0.7002	0.094*
C10	0.35766 (14)	−0.0968 (3)	0.79531 (12)	0.0533 (6)
H10	0.3267	−0.0758	0.8295	0.064*
C11	0.35773 (17)	0.2081 (4)	0.78049 (15)	0.0706 (8)
H11A	0.3245	0.2040	0.8159	0.106*
H11B	0.3300	0.2644	0.7480	0.106*
H11C	0.4052	0.2708	0.7897	0.106*
N1	0.13743 (11)	0.3839 (3)	0.41940 (9)	0.0481 (5)
N2	0.37816 (11)	0.0348 (3)	0.76212 (9)	0.0452 (5)
O1	0.27226 (10)	0.3821 (2)	0.43417 (8)	0.0577 (5)
O2	0.00221 (10)	0.3717 (2)	0.43250 (8)	0.0612 (5)
O3	0.13795 (11)	0.4787 (2)	0.36673 (8)	0.0597 (5)
H3	0.1379	0.4138	0.3373	0.090*
O4	0.37631 (13)	−0.2469 (3)	0.78468 (9)	0.0749 (6)
Cl1	0.32275 (3)	0.18521 (7)	0.55363 (3)	0.04350 (18)
Cl2	−0.04705 (3)	0.17228 (8)	0.55248 (3)	0.05155 (19)
Cl3	0.22967 (3)	0.02190 (8)	0.66120 (3)	0.04968 (19)
Cl4	0.04709 (4)	0.00212 (8)	0.65760 (3)	0.0554 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0459 (14)	0.0381 (12)	0.0393 (12)	−0.0018 (10)	0.0023 (10)	−0.0028 (9)
C2	0.0319 (11)	0.0330 (10)	0.0391 (12)	−0.0011 (9)	0.0023 (9)	−0.0040 (9)
C3	0.0298 (11)	0.0361 (11)	0.0390 (11)	−0.0012 (8)	0.0002 (9)	−0.0076 (9)
C4	0.0335 (11)	0.0358 (11)	0.0351 (11)	0.0005 (9)	−0.0016 (9)	−0.0030 (9)
C5	0.0333 (11)	0.0383 (11)	0.0367 (11)	−0.0031 (9)	0.0045 (9)	−0.0037 (9)
C6	0.0281 (11)	0.0392 (12)	0.0424 (12)	−0.0004 (8)	−0.0002 (9)	−0.0069 (9)
C7	0.0327 (11)	0.0349 (11)	0.0404 (12)	0.0000 (9)	−0.0035 (9)	−0.0061 (9)
C8	0.0454 (13)	0.0417 (12)	0.0422 (13)	0.0006 (10)	−0.0081 (10)	−0.0021 (10)
C9	0.0547 (16)	0.0831 (19)	0.0494 (15)	0.0002 (13)	0.0027 (12)	0.0048 (14)
C10	0.0554 (16)	0.0638 (17)	0.0408 (14)	−0.0016 (13)	−0.0023 (11)	−0.0020 (13)
C11	0.088 (2)	0.0539 (16)	0.0695 (19)	0.0068 (14)	−0.0037 (16)	−0.0019 (15)
N1	0.0547 (13)	0.0513 (12)	0.0381 (11)	−0.0014 (9)	−0.0047 (9)	0.0080 (9)
N2	0.0448 (11)	0.0507 (11)	0.0402 (11)	0.0010 (9)	−0.0034 (8)	0.0011 (9)
O1	0.0479 (10)	0.0712 (11)	0.0539 (10)	−0.0073 (9)	0.0119 (8)	0.0101 (9)
O2	0.0481 (10)	0.0721 (12)	0.0634 (11)	0.0025 (9)	−0.0182 (8)	0.0087 (9)
O3	0.0874 (15)	0.0487 (10)	0.0429 (10)	−0.0019 (9)	−0.0054 (9)	0.0113 (8)
O4	0.1157 (17)	0.0529 (11)	0.0562 (12)	0.0021 (11)	0.0095 (11)	0.0013 (10)
Cl1	0.0267 (3)	0.0512 (3)	0.0525 (4)	−0.0005 (2)	0.0024 (2)	−0.0021 (2)
Cl2	0.0267 (3)	0.0645 (4)	0.0635 (4)	−0.0001 (2)	−0.0016 (2)	−0.0001 (3)
Cl3	0.0416 (3)	0.0637 (4)	0.0437 (3)	−0.0001 (3)	−0.0072 (2)	0.0096 (3)
Cl4	0.0419 (3)	0.0724 (4)	0.0517 (4)	−0.0062 (3)	0.0107 (3)	0.0128 (3)

Geometric parameters (Å, º)

C1—O1	1.203 (3)	C8—N1	1.392 (3)
C1—N1	1.379 (3)	C9—N2	1.450 (3)
C1—C2	1.491 (3)	C9—H9A	0.9600
C2—C3	1.372 (3)	C9—H9B	0.9600
C2—C7	1.391 (3)	C9—H9C	0.9600
C3—C4	1.396 (3)	C10—O4	1.232 (3)
C3—Cl1	1.717 (2)	C10—N2	1.304 (3)
C4—C5	1.392 (3)	C10—H10	0.9300
C4—Cl3	1.710 (2)	C11—N2	1.450 (3)
C5—C6	1.398 (3)	C11—H11A	0.9600
C5—Cl4	1.710 (2)	C11—H11B	0.9600
C6—C7	1.373 (3)	C11—H11C	0.9600
C6—Cl2	1.711 (2)	N1—O3	1.372 (3)
C7—C8	1.492 (3)	O3—H3	0.8200
C8—O2	1.197 (3)
O1—C1—N1	125.8 (2)	N1—C8—C7	103.75 (18)
O1—C1—C2	130.0 (2)	N2—C9—H9A	109.5
N1—C1—C2	104.23 (19)	N2—C9—H9B	109.5
C3—C2—C7	121.26 (19)	H9A—C9—H9B	109.5
C3—C2—C1	130.38 (19)	N2—C9—H9C	109.5
C7—C2—C1	108.36 (18)	H9A—C9—H9C	109.5
C2—C3—C4	118.15 (19)	H9B—C9—H9C	109.5
C2—C3—Cl1	121.57 (16)	O4—C10—N2	124.8 (2)
C4—C3—Cl1	120.27 (16)	O4—C10—H10	117.6
C5—C4—C3	120.49 (18)	N2—C10—H10	117.6
C5—C4—Cl3	119.77 (15)	N2—C11—H11A	109.5
C3—C4—Cl3	119.74 (15)	N2—C11—H11B	109.5
C4—C5—C6	120.92 (18)	H11A—C11—H11B	109.5
C4—C5—Cl4	119.65 (16)	N2—C11—H11C	109.5
C6—C5—Cl4	119.43 (16)	H11A—C11—H11C	109.5
C7—C6—C5	117.75 (18)	H11B—C11—H11C	109.5
C7—C6—Cl2	121.98 (16)	O3—N1—C1	121.67 (19)
C5—C6—Cl2	120.26 (16)	O3—N1—C8	122.61 (18)
C6—C7—C2	121.41 (19)	C1—N1—C8	114.88 (19)
C6—C7—C8	130.01 (19)	C10—N2—C11	120.8 (2)
C2—C7—C8	108.57 (19)	C10—N2—C9	121.3 (2)
O2—C8—N1	125.4 (2)	C11—N2—C9	117.6 (2)
O2—C8—C7	130.8 (2)	N1—O3—H3	109.5
O1—C1—C2—C3	−3.6 (4)	Cl2—C6—C7—C2	−178.59 (15)
N1—C1—C2—C3	176.6 (2)	C5—C6—C7—C8	178.6 (2)
O1—C1—C2—C7	177.0 (2)	Cl2—C6—C7—C8	−0.3 (3)
N1—C1—C2—C7	−2.8 (2)	C3—C2—C7—C6	−0.7 (3)
C7—C2—C3—C4	−0.3 (3)	C1—C2—C7—C6	178.70 (19)
C1—C2—C3—C4	−179.5 (2)	C3—C2—C7—C8	−179.34 (19)
C7—C2—C3—Cl1	178.59 (15)	C1—C2—C7—C8	0.1 (2)
C1—C2—C3—Cl1	−0.7 (3)	C6—C7—C8—O2	3.1 (4)
C2—C3—C4—C5	1.6 (3)	C2—C7—C8—O2	−178.4 (2)
Cl1—C3—C4—C5	−177.22 (15)	C6—C7—C8—N1	−175.9 (2)
C2—C3—C4—Cl3	−178.96 (15)	C2—C7—C8—N1	2.6 (2)
Cl1—C3—C4—Cl3	2.2 (2)	O1—C1—N1—O3	−5.3 (4)
C3—C4—C5—C6	−2.1 (3)	C2—C1—N1—O3	174.53 (19)
Cl3—C4—C5—C6	178.50 (16)	O1—C1—N1—C8	−175.0 (2)
C3—C4—C5—Cl4	176.83 (16)	C2—C1—N1—C8	4.8 (3)
Cl3—C4—C5—Cl4	−2.6 (2)	O2—C8—N1—O3	6.6 (4)
C4—C5—C6—C7	1.1 (3)	C7—C8—N1—O3	−174.36 (19)
Cl4—C5—C6—C7	−177.83 (16)	O2—C8—N1—C1	176.3 (2)
C4—C5—C6—Cl2	180.00 (15)	C7—C8—N1—C1	−4.7 (3)
Cl4—C5—C6—Cl2	1.1 (2)	O4—C10—N2—C11	−175.9 (3)
C5—C6—C7—C2	0.3 (3)	O4—C10—N2—C9	−2.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4^i	0.82	1.76	2.562 (3)	167

Symmetry code: (i) −x+1/2, −y, z−1/2.