2-[2-(1,3-Dioxoisoindolin-2-yl)phenyl]­isoindoline-1,3-dione

Wu, X.-Y.; Zhu, D.-S.; Wang, Y.-H.; Zhu, C.-G.

doi:10.1107/S1600536807037038

2-[2-(1,3-Dioxoisoindolin-2-yl)phenyl]isoindoline-1,3-dione

X.-Y. Wu, D.-S. Zhu, Y.-H. Wang and C.-G. Zhu

In the title compound, C₂₂H₁₂N₂O₄, the two isoindolinyl groups are twisted with respect to the benzene ring, with dihedral angles of 58.15 (7) and 61.32 (7)°; the dihedral angle between the two isoindolinyl groups is 39.45 (6)°. The molecules are linked together by weak C—H

O hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037038/xu2298sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037038/xu2298Isup2.hkl Contains datablock I

CCDC reference: 651058

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.041
wR factor = 0.094
Data-to-parameter ratio = 13.7

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Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

Comment top

Isoindolinones and their derivatives have been investigated widely due to their profound physiological and chemotherapeutic properties. Many compounds containing the isoindolinone skeleton have shown antiviral, antileukemic, antiinflammatory, antipsychotic and antiulcer properties (Pendrak et al., 1994; De Clerck, 1995). Isoindolinones are useful for the synthesis of various drugs and naturally occurring compounds (Stowers, 1996; Heaney & Shuhaibar, 1995). In this paper, we report the crystal structure of the title compound.

As shown in Fig. 1, the structure determination indicates that the molecule is non-centrosymmetric. Due to steric encumbering, two isoindolinyl moieties are twisted to the benzene ring with dihedral angles of 58.15 (7) and 61.32 (7)°, respectively, similar to 62.31 (6)° found in 2-(2-pyridyl)isoindoline-1,3-dione (Liang & Li, 2007). The dihedral angle between the two isoindolinyl moieties is 39.45 (6)°. The molecules are linked together by weak C—H···O hydrogen bonding (Table 1).

Related literature top

For general background, see: Pendrak et al. (1994); De Clerck (1995); Stowers (1996); Heaney & Shuhaibar (1995). For a related structure, see: Liang & Li (2007).

Experimental top

O-Phenylenediamine (0.11 g, 1 mmol) was dissolved in 5 ml glacial acetic acid, and a solution of phthalic anhydride (0.148 g, 1 mmol) in 10 ml of glacial acetic acid was added. After 30 min, the mixture was diluted with cool water, and then the grey precipitate was separated and then refluxed in dry benzene (20 ml) for 4 h using Dean and Stark apparatus. After solvent was removed under reduced pressure the solid product was obtained. The colorless single crystals of the title compound were obtained by recrystallization from an ethanol solution at room temperature after 2 d.

Structure description top

For general background, see: Pendrak et al. (1994); De Clerck (1995); Stowers (1996); Heaney & Shuhaibar (1995). For a related structure, see: Liang & Li (2007).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXTL-Plus.

Figures top

Fig. 1. A view of the molecule of (I). Displacement ellipsoids are drawn at the 50% probability level.

2-[2-(1,3-Dioxoisoindolin-2-yl)phenyl]isoindoline-1,3-dione top

Crystal data top

C₂₂H₁₂N₂O₄	F(000) = 760
M_r = 368.34	D_x = 1.385 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9771 reflections
a = 10.7765 (10) Å	θ = 2.2–26.0°
b = 16.9259 (17) Å	µ = 0.10 mm⁻¹
c = 10.8518 (10) Å	T = 293 K
β = 116.780 (1)°	Block, colourless
V = 1767.1 (3) Å³	0.35 × 0.33 × 0.28 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2553 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 26.0°, θ_min = 2.2°
φ and ω scans	h = −9→13
9771 measured reflections	k = −16→20
3476 independent reflections	l = −13→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0421P)²] where P = (F_o² + 2F_c²)/3
3476 reflections	(Δ/σ)_max = 0.001
253 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₂H₁₂N₂O₄	V = 1767.1 (3) Å³
M_r = 368.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7765 (10) Å	µ = 0.10 mm⁻¹
b = 16.9259 (17) Å	T = 293 K
c = 10.8518 (10) Å	0.35 × 0.33 × 0.28 mm
β = 116.780 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2553 reflections with I > 2σ(I)
9771 measured reflections	R_int = 0.050
3476 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 0.95	Δρ_max = 0.20 e Å⁻³
3476 reflections	Δρ_min = −0.19 e Å⁻³
253 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
O1	0.45581 (11)	0.01749 (7)	0.14315 (11)	0.0365 (3)
O2	0.07744 (11)	0.13152 (8)	0.15937 (12)	0.0437 (4)
O3	0.74820 (11)	0.10013 (7)	0.38688 (11)	0.0322 (3)
O4	0.34849 (12)	0.24241 (7)	0.14859 (13)	0.0411 (3)
N1	0.28632 (13)	0.07596 (8)	0.18964 (12)	0.0264 (3)
N2	0.53713 (12)	0.16715 (8)	0.29363 (13)	0.0257 (3)
C1	0.34000 (17)	0.04363 (10)	0.10366 (16)	0.0277 (4)
C2	0.14769 (16)	0.10141 (10)	0.11178 (16)	0.0296 (4)
C3	0.66539 (16)	0.14316 (10)	0.29978 (16)	0.0252 (4)
C4	0.46318 (17)	0.21605 (10)	0.17971 (16)	0.0296 (4)
C11	0.36534 (16)	0.09109 (10)	0.33430 (15)	0.0250 (4)
C12	0.48509 (16)	0.13677 (10)	0.38461 (16)	0.0251 (4)
C13	0.55851 (17)	0.15123 (10)	0.52504 (16)	0.0312 (4)
H13A	0.6389	0.1817	0.5587	0.037*
C14	0.51259 (18)	0.12054 (11)	0.61507 (17)	0.0339 (4)
H14A	0.5619	0.1304	0.7092	0.041*
C15	0.39354 (18)	0.07529 (11)	0.56535 (16)	0.0336 (4)
H15A	0.3629	0.0544	0.6261	0.040*
C16	0.31966 (17)	0.06088 (10)	0.42531 (16)	0.0301 (4)
H16A	0.2389	0.0307	0.3921	0.036*
C21	0.22647 (16)	0.05014 (10)	−0.03928 (15)	0.0268 (4)
C22	0.11188 (16)	0.08397 (10)	−0.03443 (16)	0.0283 (4)
C23	−0.00825 (18)	0.09885 (11)	−0.15363 (17)	0.0352 (4)
H23A	−0.0856	0.1211	−0.1505	0.042*
C24	−0.00952 (18)	0.07944 (11)	−0.27824 (17)	0.0374 (4)
H24A	−0.0890	0.0892	−0.3602	0.045*
C25	0.10523 (18)	0.04581 (11)	−0.28296 (17)	0.0388 (5)
H25A	0.1015	0.0332	−0.3680	0.047*
C26	0.22624 (18)	0.03050 (11)	−0.16251 (16)	0.0347 (4)
H26A	0.3037	0.0079	−0.1652	0.042*
C31	0.67265 (16)	0.18160 (10)	0.18068 (15)	0.0270 (4)
C32	0.55298 (16)	0.22536 (10)	0.10967 (16)	0.0295 (4)
C33	0.53101 (18)	0.26772 (11)	−0.00715 (18)	0.0392 (5)
H33A	0.4505	0.2973	−0.0546	0.047*
C34	0.63355 (19)	0.26451 (12)	−0.05105 (18)	0.0429 (5)
H34A	0.6214	0.2921	−0.1298	0.051*
C35	0.75357 (19)	0.22099 (11)	0.02044 (18)	0.0388 (5)
H35A	0.8211	0.2203	−0.0107	0.047*
C36	0.77526 (17)	0.17830 (11)	0.13755 (17)	0.0327 (4)
H36A	0.8556	0.1487	0.1851	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0277 (7)	0.0500 (8)	0.0315 (6)	0.0109 (6)	0.0132 (5)	−0.0002 (6)
O2	0.0273 (7)	0.0680 (10)	0.0370 (7)	0.0069 (6)	0.0156 (6)	−0.0122 (6)
O3	0.0240 (6)	0.0402 (8)	0.0282 (6)	0.0050 (6)	0.0082 (5)	0.0051 (5)
O4	0.0267 (7)	0.0422 (8)	0.0558 (8)	0.0104 (6)	0.0199 (6)	0.0156 (6)
N1	0.0210 (7)	0.0358 (8)	0.0233 (7)	0.0002 (6)	0.0107 (6)	−0.0034 (6)
N2	0.0197 (7)	0.0312 (8)	0.0268 (7)	0.0019 (6)	0.0112 (6)	0.0054 (6)
C1	0.0277 (9)	0.0297 (10)	0.0280 (9)	0.0000 (8)	0.0145 (8)	−0.0010 (7)
C2	0.0228 (9)	0.0361 (11)	0.0305 (9)	−0.0017 (8)	0.0124 (8)	−0.0034 (8)
C3	0.0198 (8)	0.0288 (10)	0.0254 (8)	−0.0027 (7)	0.0087 (7)	−0.0018 (7)
C4	0.0247 (9)	0.0293 (10)	0.0339 (9)	0.0008 (8)	0.0123 (8)	0.0039 (8)
C11	0.0224 (9)	0.0304 (10)	0.0223 (8)	0.0031 (7)	0.0101 (7)	−0.0011 (7)
C12	0.0225 (8)	0.0281 (9)	0.0260 (8)	0.0024 (7)	0.0122 (7)	0.0019 (7)
C13	0.0247 (9)	0.0353 (11)	0.0299 (9)	−0.0026 (8)	0.0090 (8)	−0.0035 (8)
C14	0.0342 (10)	0.0432 (12)	0.0220 (8)	0.0019 (9)	0.0107 (8)	−0.0014 (8)
C15	0.0367 (10)	0.0413 (11)	0.0286 (9)	0.0010 (9)	0.0197 (8)	0.0039 (8)
C16	0.0267 (9)	0.0343 (11)	0.0331 (9)	−0.0029 (8)	0.0168 (8)	−0.0006 (8)
C21	0.0251 (9)	0.0294 (10)	0.0252 (8)	0.0009 (7)	0.0108 (7)	−0.0002 (7)
C22	0.0244 (9)	0.0328 (10)	0.0273 (9)	−0.0019 (8)	0.0113 (7)	−0.0035 (7)
C23	0.0247 (9)	0.0423 (12)	0.0329 (9)	0.0027 (8)	0.0080 (8)	−0.0035 (8)
C24	0.0338 (10)	0.0401 (11)	0.0276 (9)	0.0002 (9)	0.0043 (8)	0.0007 (8)
C25	0.0441 (11)	0.0454 (12)	0.0243 (9)	0.0004 (9)	0.0131 (9)	−0.0043 (8)
C26	0.0366 (10)	0.0402 (11)	0.0294 (9)	0.0046 (9)	0.0167 (8)	−0.0024 (8)
C31	0.0240 (9)	0.0300 (10)	0.0271 (8)	−0.0024 (7)	0.0117 (7)	−0.0002 (7)
C32	0.0245 (9)	0.0335 (10)	0.0309 (9)	−0.0004 (8)	0.0127 (8)	0.0041 (8)
C33	0.0325 (10)	0.0434 (12)	0.0395 (10)	0.0044 (9)	0.0143 (9)	0.0137 (9)
C34	0.0461 (12)	0.0509 (13)	0.0350 (10)	−0.0047 (10)	0.0214 (9)	0.0104 (9)
C35	0.0397 (11)	0.0485 (13)	0.0373 (10)	−0.0071 (9)	0.0253 (9)	−0.0013 (9)
C36	0.0278 (9)	0.0378 (11)	0.0340 (9)	−0.0005 (8)	0.0152 (8)	−0.0010 (8)

Geometric parameters (Å, º) top

O1—C1	1.2063 (18)	C15—H15A	0.9300
O2—C2	1.2050 (18)	C16—H16A	0.9300
O3—C3	1.2083 (18)	C21—C26	1.377 (2)
O4—C4	1.2101 (18)	C21—C22	1.384 (2)
N1—C1	1.4110 (19)	C22—C23	1.380 (2)
N1—C2	1.412 (2)	C23—C24	1.386 (2)
N1—C11	1.4320 (18)	C23—H23A	0.9300
N2—C4	1.400 (2)	C24—C25	1.383 (2)
N2—C3	1.4131 (19)	C24—H24A	0.9300
N2—C12	1.4328 (19)	C25—C26	1.393 (2)
C1—C21	1.485 (2)	C25—H25A	0.9300
C2—C22	1.484 (2)	C26—H26A	0.9300
C3—C31	1.480 (2)	C31—C32	1.382 (2)
C4—C32	1.484 (2)	C31—C36	1.383 (2)
C11—C16	1.385 (2)	C32—C33	1.381 (2)
C11—C12	1.388 (2)	C33—C34	1.388 (2)
C12—C13	1.386 (2)	C33—H33A	0.9300
C13—C14	1.380 (2)	C34—C35	1.383 (2)
C13—H13A	0.9300	C34—H34A	0.9300
C14—C15	1.378 (2)	C35—C36	1.387 (2)
C14—H14A	0.9300	C35—H35A	0.9300
C15—C16	1.383 (2)	C36—H36A	0.9300

C1—N1—C2	111.16 (13)	C26—C21—C22	121.72 (15)
C1—N1—C11	125.16 (13)	C26—C21—C1	129.55 (15)
C2—N1—C11	123.21 (12)	C22—C21—C1	108.68 (13)
C4—N2—C3	111.54 (12)	C23—C22—C21	121.09 (15)
C4—N2—C12	125.22 (12)	C23—C22—C2	130.42 (15)
C3—N2—C12	122.86 (13)	C21—C22—C2	108.45 (14)
O1—C1—N1	125.04 (14)	C22—C23—C24	117.67 (16)
O1—C1—C21	129.19 (15)	C22—C23—H23A	121.2
N1—C1—C21	105.77 (13)	C24—C23—H23A	121.2
O2—C2—N1	124.91 (15)	C25—C24—C23	121.19 (16)
O2—C2—C22	129.15 (15)	C25—C24—H24A	119.4
N1—C2—C22	105.93 (13)	C23—C24—H24A	119.4
O3—C3—N2	124.90 (14)	C24—C25—C26	121.09 (16)
O3—C3—C31	129.57 (14)	C24—C25—H25A	119.5
N2—C3—C31	105.53 (13)	C26—C25—H25A	119.5
O4—C4—N2	124.59 (15)	C21—C26—C25	117.24 (16)
O4—C4—C32	129.63 (15)	C21—C26—H26A	121.4
N2—C4—C32	105.77 (13)	C25—C26—H26A	121.4
C16—C11—C12	119.44 (14)	C32—C31—C36	121.38 (15)
C16—C11—N1	119.27 (14)	C32—C31—C3	108.62 (13)
C12—C11—N1	121.28 (13)	C36—C31—C3	130.00 (15)
C13—C12—C11	119.99 (14)	C33—C32—C31	121.41 (15)
C13—C12—N2	119.17 (14)	C33—C32—C4	130.07 (15)
C11—C12—N2	120.81 (13)	C31—C32—C4	108.52 (14)
C14—C13—C12	120.17 (15)	C32—C33—C34	117.47 (16)
C14—C13—H13A	119.9	C32—C33—H33A	121.3
C12—C13—H13A	119.9	C34—C33—H33A	121.3
C15—C14—C13	119.96 (15)	C35—C34—C33	121.09 (16)
C15—C14—H14A	120.0	C35—C34—H34A	119.5
C13—C14—H14A	120.0	C33—C34—H34A	119.5
C14—C15—C16	120.11 (15)	C34—C35—C36	121.35 (16)
C14—C15—H15A	119.9	C34—C35—H35A	119.3
C16—C15—H15A	119.9	C36—C35—H35A	119.3
C15—C16—C11	120.33 (15)	C31—C36—C35	117.31 (16)
C15—C16—H16A	119.8	C31—C36—H36A	121.3
C11—C16—H16A	119.8	C35—C36—H36A	121.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O4ⁱ	0.93	2.39	3.321 (2)	179
C24—H24A···O3ⁱⁱ	0.93	2.51	3.405 (2)	161
C26—H26A···O1ⁱⁱⁱ	0.93	2.53	3.434 (2)	164
C34—H34A···O2^iv	0.93	2.48	3.410 (2)	177
C36—H36A···O2^v	0.93	2.55	3.255 (2)	133

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1, y, z−1; (iii) −x+1, −y, −z; (iv) x+1/2, −y+1/2, z−1/2; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₂N₂O₄
M_r	368.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.7765 (10), 16.9259 (17), 10.8518 (10)
β (°)	116.780 (1)
V (Å³)	1767.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.35 × 0.33 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9771, 3476, 2553
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.094, 0.95
No. of reflections	3476
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.19

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXTL-Plus.