2-(4,5,6,7-Tetra­chloro-1,3-dioxoisoindolin-2-yl)benzoic acid N,N-dimethyl­formamide solvate

Li, J.

doi:10.1107/S1600536807030644

2-(4,5,6,7-Tetrachloro-1,3-dioxoisoindolin-2-yl)benzoic acid N,N-dimethylformamide solvate

J. Li

In the crystal structure of the title compound, C₁₅H₅Cl₄NO₄·C₃H₇NO, O—H

O hydrogen bonds help to establish the crystal packing. The dihedral angle between the tetrachlorophthalimide group and the benzene ring is 74.2 (2)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030644/hb2454sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030644/hb2454Isup2.hkl Contains datablock I

CCDC reference: 655051

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.054
wR factor = 0.121
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
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  Cl2    ..  O1      ..       3.17 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl3    ..  O3      ..       3.20 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

Comment top

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 2-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)benzoic acid 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). The tetrachlorophthalimide group is essentially planar, with a mean deviation of 0.424 (3) Å. The dihedral angle between the tetrachlorophthalimide group and the benzene C9—C14 ring is 74.2 (2) °. The DMF molecule is planar, within 0.009 (2) Å, for all non-H atoms. 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 top

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

Experimental top

A mixture of 4,5,6,7-tetrachloroisobenzofuran-1,3-dione (0.01 mol) and 2-aminobenzoic acid (0.01 mol) in acetic acid (10 ml) was refluxed for 1 h. After cooling, filtration and drying, 2-(4,5,6,7-tetrachloro-1,3-dioxoisoindolin-2-yl)benzoic acid was obtained. 10 mg of this compound was dissolved in DMF (7 ml), and the solution was kept at room temperature for 5 d. Natural evaporation gave colourless bars of (I).

Structure description top

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

Computing details top

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 top

	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 c axis. Hydrogen bonds are indicated by dashed lines.

2-(4,5,6,7-Tetrachloro-1,3-dioxoisoindolin-2-yl)benzoic acid N,N-dimethylformamide solvate top

Crystal data top

C₁₅H₅Cl₄NO₄·C₃H₇NO	F(000) = 968
M_r = 478.10	D_x = 1.588 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1625 reflections
a = 16.593 (4) Å	θ = 2.8–21.0°
b = 13.816 (3) Å	µ = 0.63 mm⁻¹
c = 8.815 (2) Å	T = 298 K
β = 98.224 (3)°	Bar, colourless
V = 2000.1 (8) Å³	0.44 × 0.10 × 0.05 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3528 independent reflections
Radiation source: fine-focus sealed tube	2587 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −19→19
T_min = 0.770, T_max = 0.969	k = −16→14
8292 measured reflections	l = −10→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0496P)²] where P = (F_o² + 2F_c²)/3
3528 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₅H₅Cl₄NO₄·C₃H₇NO	V = 2000.1 (8) Å³
M_r = 478.10	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.593 (4) Å	µ = 0.63 mm⁻¹
b = 13.816 (3) Å	T = 298 K
c = 8.815 (2) Å	0.44 × 0.10 × 0.05 mm
β = 98.224 (3)°

Data collection top

Bruker SMART CCD diffractometer	3528 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2587 reflections with I > 2σ(I)
T_min = 0.770, T_max = 0.969	R_int = 0.040
8292 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.09	Δρ_max = 0.24 e Å⁻³
3528 reflections	Δρ_min = −0.23 e Å⁻³
265 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.78652 (19)	0.8663 (2)	0.5252 (4)	0.0391 (8)
C2	0.87721 (18)	0.8736 (2)	0.5443 (4)	0.0361 (7)
C3	0.9324 (2)	0.8832 (2)	0.6743 (4)	0.0407 (8)
C4	1.0152 (2)	0.8842 (2)	0.6598 (4)	0.0420 (8)
C5	1.03952 (18)	0.8758 (2)	0.5153 (4)	0.0402 (8)
C6	0.98224 (18)	0.8674 (2)	0.3831 (4)	0.0362 (7)
C7	0.90112 (17)	0.8657 (2)	0.4001 (3)	0.0335 (7)
C8	0.82696 (18)	0.8506 (2)	0.2852 (4)	0.0353 (7)
C9	0.67996 (18)	0.8270 (2)	0.3073 (4)	0.0419 (8)
C10	0.6508 (2)	0.7372 (3)	0.3368 (4)	0.0573 (10)
H10	0.6842	0.6933	0.3960	0.069*
C11	0.5722 (2)	0.7120 (3)	0.2789 (5)	0.0661 (11)
H11	0.5524	0.6512	0.2996	0.079*
C12	0.5232 (2)	0.7764 (3)	0.1909 (5)	0.0658 (12)
H12	0.4704	0.7588	0.1500	0.079*
C13	0.5518 (2)	0.8662 (3)	0.1634 (4)	0.0585 (10)
H13	0.5179	0.9094	0.1038	0.070*
C14	0.63042 (19)	0.8948 (2)	0.2221 (4)	0.0452 (9)
C15	0.6573 (2)	0.9951 (3)	0.1991 (5)	0.0571 (10)
C16	0.7469 (4)	0.4024 (4)	0.3307 (6)	0.128 (2)
H16A	0.7796	0.3524	0.3842	0.192*
H16B	0.7180	0.4364	0.4012	0.192*
H16C	0.7814	0.4468	0.2862	0.192*
C17	0.6316 (3)	0.4208 (4)	0.1177 (8)	0.124 (2)
H17A	0.6535	0.4397	0.0272	0.186*
H17B	0.6212	0.4774	0.1751	0.186*
H17C	0.5816	0.3861	0.0891	0.186*
C18	0.6885 (3)	0.2661 (4)	0.1868 (6)	0.0765 (13)
H18	0.7250	0.2281	0.2512	0.092*
Cl1	1.01316 (5)	0.86077 (6)	0.20580 (10)	0.0486 (3)
Cl2	0.90173 (6)	0.88868 (7)	0.85233 (10)	0.0573 (3)
Cl3	1.14152 (5)	0.87399 (7)	0.50024 (12)	0.0597 (3)
Cl4	1.08683 (6)	0.89372 (8)	0.81974 (11)	0.0669 (3)
N1	0.76245 (14)	0.84798 (18)	0.3700 (3)	0.0387 (6)
N2	0.6890 (2)	0.3596 (3)	0.2105 (5)	0.0793 (11)
O1	0.82200 (13)	0.83982 (17)	0.1491 (3)	0.0497 (6)
O2	0.74198 (14)	0.87608 (17)	0.6190 (3)	0.0553 (7)
O3	0.71942 (17)	1.0292 (2)	0.2590 (4)	0.0976 (11)
O4	0.60601 (17)	1.0458 (2)	0.1063 (4)	0.1018 (11)
H4	0.6238	1.1008	0.0999	0.153*
O5	0.64297 (19)	0.2258 (2)	0.0852 (4)	0.0922 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0441 (19)	0.0397 (19)	0.033 (2)	0.0051 (15)	0.0016 (16)	0.0035 (15)
C2	0.0414 (18)	0.0324 (17)	0.0332 (19)	0.0051 (14)	0.0009 (15)	0.0028 (14)
C3	0.053 (2)	0.0376 (19)	0.0289 (19)	0.0027 (15)	−0.0018 (16)	0.0025 (14)
C4	0.050 (2)	0.0359 (19)	0.035 (2)	0.0018 (14)	−0.0121 (16)	0.0009 (15)
C5	0.0363 (18)	0.0358 (18)	0.045 (2)	0.0008 (14)	−0.0051 (16)	0.0015 (15)
C6	0.0375 (18)	0.0369 (18)	0.0328 (19)	0.0017 (14)	0.0000 (14)	−0.0002 (15)
C7	0.0344 (17)	0.0361 (17)	0.0279 (18)	0.0009 (13)	−0.0025 (13)	0.0015 (14)
C8	0.0353 (18)	0.0395 (19)	0.029 (2)	−0.0020 (14)	−0.0014 (14)	0.0026 (15)
C9	0.0340 (18)	0.057 (2)	0.034 (2)	−0.0011 (16)	0.0033 (15)	−0.0030 (17)
C10	0.051 (2)	0.064 (3)	0.057 (3)	−0.0038 (19)	0.008 (2)	0.008 (2)
C11	0.059 (3)	0.065 (3)	0.076 (3)	−0.017 (2)	0.016 (2)	0.002 (2)
C12	0.040 (2)	0.083 (3)	0.074 (3)	−0.018 (2)	0.008 (2)	−0.009 (2)
C13	0.037 (2)	0.080 (3)	0.056 (3)	−0.0026 (19)	−0.0020 (18)	0.002 (2)
C14	0.0341 (19)	0.058 (2)	0.042 (2)	−0.0014 (16)	0.0011 (16)	−0.0035 (18)
C15	0.037 (2)	0.067 (3)	0.063 (3)	0.0055 (19)	−0.0071 (19)	0.002 (2)
C16	0.173 (6)	0.126 (5)	0.086 (4)	−0.074 (4)	0.017 (4)	−0.020 (4)
C17	0.114 (5)	0.071 (4)	0.188 (7)	−0.007 (3)	0.022 (5)	0.025 (4)
C18	0.061 (3)	0.085 (4)	0.080 (4)	−0.012 (3)	0.001 (2)	0.008 (3)
Cl1	0.0435 (5)	0.0632 (6)	0.0394 (5)	−0.0020 (4)	0.0074 (4)	−0.0041 (4)
Cl2	0.0743 (7)	0.0680 (6)	0.0273 (5)	0.0027 (5)	−0.0004 (4)	−0.0017 (4)
Cl3	0.0336 (5)	0.0709 (6)	0.0704 (7)	0.0007 (4)	−0.0074 (4)	−0.0015 (5)
Cl4	0.0632 (6)	0.0823 (7)	0.0454 (6)	−0.0003 (5)	−0.0254 (5)	−0.0032 (5)
N1	0.0289 (14)	0.0557 (17)	0.0305 (16)	0.0001 (12)	0.0007 (12)	0.0019 (13)
N2	0.084 (3)	0.072 (3)	0.084 (3)	−0.023 (2)	0.020 (2)	0.002 (2)
O1	0.0419 (14)	0.0784 (17)	0.0278 (14)	−0.0075 (11)	0.0015 (10)	−0.0054 (12)
O2	0.0528 (15)	0.0754 (18)	0.0395 (15)	0.0042 (12)	0.0125 (12)	−0.0052 (13)
O3	0.066 (2)	0.072 (2)	0.136 (3)	−0.0150 (16)	−0.0480 (19)	0.0227 (19)
O4	0.070 (2)	0.074 (2)	0.141 (3)	−0.0064 (16)	−0.0514 (19)	0.035 (2)
O5	0.087 (2)	0.073 (2)	0.107 (3)	0.0002 (17)	−0.020 (2)	0.0049 (19)

Geometric parameters (Å, º) top

C1—O2	1.193 (3)	C11—C12	1.369 (5)
C1—N1	1.392 (4)	C11—H11	0.9300
C1—C2	1.494 (4)	C12—C13	1.363 (5)
C2—C3	1.367 (4)	C12—H12	0.9300
C2—C7	1.389 (4)	C13—C14	1.390 (5)
C3—C4	1.398 (4)	C13—H13	0.9300
C3—Cl2	1.719 (3)	C14—C15	1.478 (5)
C4—C5	1.395 (5)	C15—O3	1.187 (4)
C4—Cl4	1.714 (3)	C15—O4	1.298 (4)
C5—C6	1.399 (4)	C16—N2	1.451 (6)
C5—Cl3	1.717 (3)	C16—H16A	0.9600
C6—C7	1.376 (4)	C16—H16B	0.9600
C6—Cl1	1.716 (3)	C16—H16C	0.9600
C7—C8	1.493 (4)	C17—N2	1.439 (6)
C8—O1	1.200 (3)	C17—H17A	0.9600
C8—N1	1.391 (4)	C17—H17B	0.9600
C9—C10	1.370 (4)	C17—H17C	0.9600
C9—C14	1.393 (4)	C18—O5	1.220 (5)
C9—N1	1.431 (4)	C18—N2	1.308 (5)
C10—C11	1.376 (5)	C18—H18	0.9300
C10—H10	0.9300	O4—H4	0.8200

O2—C1—N1	125.6 (3)	C13—C12—H12	120.1
O2—C1—C2	128.9 (3)	C11—C12—H12	120.1
N1—C1—C2	105.4 (3)	C12—C13—C14	121.7 (4)
C3—C2—C7	122.0 (3)	C12—C13—H13	119.1
C3—C2—C1	130.2 (3)	C14—C13—H13	119.1
C7—C2—C1	107.8 (3)	C13—C14—C9	117.3 (3)
C2—C3—C4	118.3 (3)	C13—C14—C15	120.1 (3)
C2—C3—Cl2	121.2 (3)	C9—C14—C15	122.5 (3)
C4—C3—Cl2	120.4 (3)	O3—C15—O4	121.1 (4)
C5—C4—C3	119.9 (3)	O3—C15—C14	124.8 (4)
C5—C4—Cl4	120.0 (3)	O4—C15—C14	114.2 (3)
C3—C4—Cl4	120.0 (3)	N2—C16—H16A	109.5
C4—C5—C6	121.1 (3)	N2—C16—H16B	109.5
C4—C5—Cl3	119.3 (3)	H16A—C16—H16B	109.5
C6—C5—Cl3	119.6 (3)	N2—C16—H16C	109.5
C7—C6—C5	118.0 (3)	H16A—C16—H16C	109.5
C7—C6—Cl1	121.5 (2)	H16B—C16—H16C	109.5
C5—C6—Cl1	120.5 (2)	N2—C17—H17A	109.5
C6—C7—C2	120.7 (3)	N2—C17—H17B	109.5
C6—C7—C8	130.8 (3)	H17A—C17—H17B	109.5
C2—C7—C8	108.5 (3)	N2—C17—H17C	109.5
O1—C8—N1	125.9 (3)	H17A—C17—H17C	109.5
O1—C8—C7	128.9 (3)	H17B—C17—H17C	109.5
N1—C8—C7	105.2 (3)	O5—C18—N2	123.8 (5)
C10—C9—C14	120.9 (3)	O5—C18—H18	118.1
C10—C9—N1	117.0 (3)	N2—C18—H18	118.1
C14—C9—N1	122.0 (3)	C8—N1—C1	112.9 (3)
C9—C10—C11	120.1 (4)	C8—N1—C9	124.4 (3)
C9—C10—H10	120.0	C1—N1—C9	122.7 (3)
C11—C10—H10	120.0	C18—N2—C17	120.1 (4)
C12—C11—C10	120.0 (4)	C18—N2—C16	120.5 (5)
C12—C11—H11	120.0	C17—N2—C16	119.4 (5)
C10—C11—H11	120.0	C15—O4—H4	109.5
C13—C12—C11	119.9 (4)

O2—C1—C2—C3	7.5 (5)	C2—C7—C8—N1	−1.5 (3)
N1—C1—C2—C3	−174.2 (3)	C14—C9—C10—C11	1.6 (5)
O2—C1—C2—C7	−174.5 (3)	N1—C9—C10—C11	−179.5 (3)
N1—C1—C2—C7	3.8 (3)	C9—C10—C11—C12	0.4 (6)
C7—C2—C3—C4	−0.5 (4)	C10—C11—C12—C13	−1.3 (6)
C1—C2—C3—C4	177.2 (3)	C11—C12—C13—C14	0.2 (6)
C7—C2—C3—Cl2	−177.7 (2)	C12—C13—C14—C9	1.7 (5)
C1—C2—C3—Cl2	0.1 (5)	C12—C13—C14—C15	−175.6 (3)
C2—C3—C4—C5	0.2 (4)	C10—C9—C14—C13	−2.6 (5)
Cl2—C3—C4—C5	177.4 (2)	N1—C9—C14—C13	178.5 (3)
C2—C3—C4—Cl4	−178.7 (2)	C10—C9—C14—C15	174.6 (3)
Cl2—C3—C4—Cl4	−1.5 (4)	N1—C9—C14—C15	−4.3 (5)
C3—C4—C5—C6	0.7 (5)	C13—C14—C15—O3	171.1 (4)
Cl4—C4—C5—C6	179.6 (2)	C9—C14—C15—O3	−6.0 (6)
C3—C4—C5—Cl3	−178.3 (2)	C13—C14—C15—O4	−8.4 (5)
Cl4—C4—C5—Cl3	0.6 (4)	C9—C14—C15—O4	174.5 (4)
C4—C5—C6—C7	−1.3 (4)	O1—C8—N1—C1	−177.8 (3)
Cl3—C5—C6—C7	177.7 (2)	C7—C8—N1—C1	4.1 (3)
C4—C5—C6—Cl1	178.0 (2)	O1—C8—N1—C9	3.3 (5)
Cl3—C5—C6—Cl1	−3.0 (4)	C7—C8—N1—C9	−174.8 (3)
C5—C6—C7—C2	1.0 (4)	O2—C1—N1—C8	173.4 (3)
Cl1—C6—C7—C2	−178.3 (2)	C2—C1—N1—C8	−4.9 (3)
C5—C6—C7—C8	−175.1 (3)	O2—C1—N1—C9	−7.7 (5)
Cl1—C6—C7—C8	5.6 (5)	C2—C1—N1—C9	173.9 (3)
C3—C2—C7—C6	−0.1 (4)	C10—C9—N1—C8	104.9 (3)
C1—C2—C7—C6	−178.3 (3)	C14—C9—N1—C8	−76.2 (4)
C3—C2—C7—C8	176.8 (3)	C10—C9—N1—C1	−73.9 (4)
C1—C2—C7—C8	−1.4 (3)	C14—C9—N1—C1	105.0 (4)
C6—C7—C8—O1	−3.0 (5)	O5—C18—N2—C17	2.4 (7)
C2—C7—C8—O1	−179.5 (3)	O5—C18—N2—C16	−178.0 (4)
C6—C7—C8—N1	175.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5ⁱ	0.82	1.76	2.574 (4)	169

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₅Cl₄NO₄·C₃H₇NO
M_r	478.10
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	16.593 (4), 13.816 (3), 8.815 (2)
β (°)	98.224 (3)
V (Å³)	2000.1 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.63
Crystal size (mm)	0.44 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.770, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	8292, 3528, 2587
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.121, 1.09
No. of reflections	3528
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.