2,2′-(1,3,5,7-Tetra­oxo-1,2,3,5,6,7-hexa­hydro­pyrrolo[3,4-f]isoindole-2,6-di­yl)diacetic acid N,N-dimethyl­formamide disolvate

Ge, C.; Li, X.; Zhang, X.; Zhao, Y.; Zhang, R.

doi:10.1107/S1600536809035107

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2400

doi:10.1107/S1600536809035107

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2,2′-(1,3,5,7-Tetraoxo-1,2,3,5,6,7-hexahydropyrrolo[3,4-f]isoindole-2,6-diyl)diacetic acid N,N-dimethylformamide disolvate

Chunhua Ge,^a ^* Xiangqian Li,^a Xiangdong Zhang,^a Yang Zhao ^a and Rui Zhang ^a

^aCollege of Chemistry, Liaoning University, Shenyang 110036, People's Republic of China
^*Correspondence e-mail: chhge@lnu.edu.cn

(Received 25 August 2009; accepted 1 September 2009; online 9 September 2009)

The asymmetric unit of the title compound, C₁₄H₈N₂O₈·2C₃H₇NO or L·2DMF (DMF = N,N-dimethylformamide), contains one half of the centrosymmetric molecule L and one solvent molecule, which is disordered between two orientations in a 0.555 (4):0.445 (4) ratio. Intermolecular O—H⋯O hydrogen bonds link one L and two DMF molecules into a centrosymmetric hydrogen-bonded cluster. The crystal packing is further stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For recent developments in the chemistry of naphthalene diimides, see Bhosale et al. (2008 ). For pyromellitic diimides, see: Gabriel & Iverson (2002 ); Ghosh & Ramakrishnan (2005 ); Kimizuka et al. (1995 ). For details of the synthesis, see Barooah et al. (2006 ).

Experimental

Crystal data

C₁₄H₈N₂O₈·2C₃H₇NO
M_r = 478.42
Monoclinic, P 2₁ /c
a = 7.7470 (15) Å
b = 9.3100 (19) Å
c = 16.334 (5) Å
β = 104.02 (3)°
V = 1143.0 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.958, T_max = 0.973
6227 measured reflections
2236 independent reflections
1910 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.111
S = 1.06
2236 reflections
166 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O5A	0.82	1.72	2.526 (2)	166
O4—H4B⋯O5B	0.82	1.70	2.496 (2)	162
C2—H2A⋯O3ⁱ	0.97	2.41	3.230 (2)	142
C6—H6⋯O1ⁱⁱ	0.93	2.50	3.414 (2)	166
C9—H9A⋯O2ⁱⁱⁱ	0.96	2.57	3.432 (3)	149
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x-1, y, z; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809035107/cv2607sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809035107/cv2607Isup2.hkl

checkCIF report

Comment top

Interest in the derivatives of diimide such as pyromellitic diimides, naphthalene diimides, and perylene diimides has arisen because of their potential applications for supramolecular and new functional materials (Bhosale et al., 2008). There have been a number of studies investigating the host–guest chemistry about pyromellitic diimide (Gabriel & Iverson, 2002; Ghosh & Ramakrishnan, 2005; Kimizuka et al., 1995). Supramolecular host of L and inclusion compounds with aromatic guests have been described (Barooah et al., 2006). In this paper, we report the crystal structure of the title compound, obtained by the recrystallization in DMF-MeOH.

In the molecule L (=2,2'-(1,3,5,7-tetraoxo-5,7-dihydropyrrolo[3,4- f]isoindole-2,6-diyl)diacetic acid), two acetic acid groups are placed on upper and lower sides of the rigid conjugate plane (Fig. 1). Intermolecular O—H···O hydrogen bonds (Table 1) link one L and two solvent molecules into centrosymmetric hydrogen-bonded cluster. The crystal packing is further stabilized by weak intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

For recent developments in the chemistry of naphthalene diimides, see Bhosale et al. (2008). For pyromellitic diimides, see: Gabriel & Iverson (2002); Ghosh & Ramakrishnan (2005); Kimizuka et al. (1995). For details of the synthesis, see Barooah et al. (2006).

Experimental top

2,2'-(1,3,5,7-Tetraoxo-5,7-dihydropyrrolo[3,4-f]isoindole-2,6-diyl)diacetic acid was synthesized according to the literature (Barooah et al., 2006). N,N'-dimethylformamide (DMF) 5 ml was added into a solution of compound mentioned above 0.1 mmol in 20 ml MeOH. The resultant colourless solution was filtered. Crystals suitable for X-ray analysis were formed after three days at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A portion of the crystal structure of the title compound showing the hydrogen-bonded (dashed lines) claster, atomic numbering and 30% probabilty displacement ellipsoids. Unlabelled atoms are related to the labelled ones by symmetry element (1 - x, 2 - y, 1 - z). For the disordered atoms, only major parts are drawn.

2,2'-(1,3,5,7-Tetraoxo-1,2,3,5,6,7-hexahydropyrrolo[3,4-f]isoindole- 2,6-diyl)diacetic acid N,N-dimethylformamide disolvate top

Crystal data top

C₁₄H₈N₂O₈·2C₃H₇NO	F(000) = 500
M_r = 478.42	D_x = 1.390 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 541 reflections
a = 7.7470 (15) Å	θ = 2.5–22.7°
b = 9.3100 (19) Å	µ = 0.11 mm⁻¹
c = 16.334 (5) Å	T = 293 K
β = 104.02 (3)°	Block, colourless
V = 1143.0 (5) Å³	0.30 × 0.25 × 0.25 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2236 independent reflections
Radiation source: fine-focus sealed tube	1910 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.958, T_max = 0.973	k = −11→10
6227 measured reflections	l = −20→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0528P)² + 0.2565P] where P = (F_o² + 2F_c²)/3
2236 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₄H₈N₂O₈·2C₃H₇NO	V = 1143.0 (5) Å³
M_r = 478.42	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7470 (15) Å	µ = 0.11 mm⁻¹
b = 9.3100 (19) Å	T = 293 K
c = 16.334 (5) Å	0.30 × 0.25 × 0.25 mm
β = 104.02 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2236 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1910 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.973	R_int = 0.030
6227 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.06	Δρ_max = 0.18 e Å⁻³
2236 reflections	Δρ_min = −0.15 e Å⁻³
166 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	Occ. (<1)
O3	0.46550 (18)	0.49571 (11)	0.66856 (7)	0.0615 (3)
H3A	0.4139	0.5238	0.6214	0.061*	0.555 (4)
O4	0.48981 (19)	0.29416 (13)	0.59801 (7)	0.0689 (4)
H4B	0.4357	0.3423	0.5579	0.069*	0.445 (4)
O1	0.86755 (14)	0.43154 (15)	0.88375 (8)	0.0638 (4)
O2	0.27767 (14)	0.31116 (13)	0.79491 (7)	0.0573 (3)
N1	0.58016 (15)	0.35733 (14)	0.82137 (7)	0.0451 (3)
C1	0.51315 (19)	0.36686 (16)	0.66427 (9)	0.0457 (3)
C2	0.6117 (2)	0.29280 (17)	0.74458 (10)	0.0504 (4)
H2A	0.5759	0.1928	0.7422	0.060*
H2B	0.7383	0.2956	0.7476	0.060*
C3	0.71166 (19)	0.42013 (16)	0.88520 (9)	0.0447 (3)
C4	0.41265 (18)	0.35918 (15)	0.84052 (9)	0.0429 (3)
C5	0.43776 (17)	0.43160 (14)	0.92473 (8)	0.0388 (3)
C6	0.31300 (17)	0.46298 (15)	0.97165 (9)	0.0410 (3)
H6	0.1933	0.4390	0.9531	0.049*
C7	0.61865 (17)	0.46738 (15)	0.95191 (8)	0.0390 (3)
N2	0.09136 (18)	0.56664 (15)	0.40440 (9)	0.0545 (4)
C10	0.2173 (2)	0.5240 (2)	0.46976 (11)	0.0592 (4)
H10A	0.2662	0.4330	0.4691	0.071*	0.555 (4)
H10B	0.2583	0.5849	0.5155	0.071*	0.445 (4)
C9	0.0213 (3)	0.4691 (2)	0.33408 (13)	0.0726 (5)
H9A	0.0839	0.3793	0.3439	0.109*
H9B	0.0370	0.5110	0.2827	0.109*
H9C	−0.1031	0.4529	0.3295	0.109*
C8	0.0168 (3)	0.7115 (2)	0.40126 (13)	0.0707 (5)
H8A	0.0662	0.7600	0.4536	0.106*
H8B	−0.1101	0.7056	0.3925	0.106*
H8C	0.0454	0.7640	0.3557	0.106*
O5A	0.2757 (3)	0.6081 (2)	0.53640 (13)	0.0644 (8)	0.555 (4)
O5B	0.2835 (4)	0.3945 (3)	0.46915 (17)	0.0705 (11)	0.445 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0914 (9)	0.0416 (6)	0.0451 (6)	0.0103 (6)	0.0044 (6)	−0.0013 (5)
O4	0.0965 (10)	0.0517 (7)	0.0497 (7)	0.0094 (6)	0.0004 (6)	−0.0124 (5)
O1	0.0363 (6)	0.0933 (9)	0.0612 (7)	−0.0030 (6)	0.0105 (5)	−0.0050 (6)
O2	0.0464 (6)	0.0670 (7)	0.0513 (6)	−0.0117 (5)	−0.0021 (5)	−0.0040 (5)
N1	0.0416 (6)	0.0520 (7)	0.0393 (6)	−0.0001 (5)	0.0049 (5)	0.0040 (5)
C1	0.0469 (8)	0.0430 (8)	0.0452 (8)	−0.0043 (6)	0.0074 (6)	0.0013 (6)
C2	0.0553 (9)	0.0465 (8)	0.0478 (8)	0.0061 (7)	0.0096 (7)	0.0031 (6)
C3	0.0373 (7)	0.0499 (8)	0.0432 (7)	0.0010 (6)	0.0025 (6)	0.0091 (6)
C4	0.0407 (7)	0.0417 (7)	0.0413 (7)	−0.0020 (6)	0.0006 (6)	0.0092 (6)
C5	0.0345 (7)	0.0380 (7)	0.0391 (7)	−0.0020 (5)	−0.0007 (5)	0.0102 (5)
C6	0.0291 (6)	0.0451 (7)	0.0439 (7)	−0.0036 (5)	−0.0010 (5)	0.0088 (6)
C7	0.0321 (7)	0.0408 (7)	0.0409 (7)	0.0004 (5)	0.0027 (5)	0.0108 (6)
N2	0.0486 (7)	0.0539 (8)	0.0562 (8)	0.0005 (6)	0.0033 (6)	0.0000 (6)
C10	0.0557 (10)	0.0610 (10)	0.0573 (10)	0.0013 (8)	0.0069 (8)	0.0063 (8)
C9	0.0696 (12)	0.0693 (12)	0.0691 (12)	0.0050 (10)	−0.0019 (9)	−0.0119 (9)
C8	0.0690 (12)	0.0566 (10)	0.0766 (12)	0.0060 (9)	−0.0016 (9)	−0.0009 (9)
O5A	0.0737 (15)	0.0581 (13)	0.0527 (13)	0.0055 (11)	−0.0016 (10)	0.0063 (10)
O5B	0.081 (2)	0.069 (2)	0.0497 (16)	0.0120 (15)	−0.0070 (13)	0.0009 (13)

Geometric parameters (Å, º) top

O3—C1	1.2621 (18)	C6—C7ⁱ	1.393 (2)
O3—H3A	0.8200	C6—H6	0.9300
O4—C1	1.2519 (18)	C7—C6ⁱ	1.393 (2)
O4—H4B	0.8200	N2—C10	1.321 (2)
O1—C3	1.2182 (18)	N2—C9	1.462 (2)
O2—C4	1.2128 (17)	N2—C8	1.463 (2)
N1—C3	1.3971 (19)	C10—O5B	1.311 (3)
N1—C4	1.4067 (19)	C10—O5A	1.328 (3)
N1—C2	1.464 (2)	C10—H10A	0.9300
C1—C2	1.515 (2)	C10—H10B	0.9300
C2—H2A	0.9700	C9—H9A	0.9600
C2—H2B	0.9700	C9—H9B	0.9600
C3—C7	1.510 (2)	C9—H9C	0.9600
C4—C5	1.502 (2)	C8—H8A	0.9600
C5—C6	1.402 (2)	C8—H8B	0.9600
C5—C7	1.4037 (19)	C8—H8C	0.9600

C1—O3—H3A	109.5	C6ⁱ—C7—C5	121.85 (13)
C1—O4—H4B	109.5	C6ⁱ—C7—C3	129.67 (12)
C3—N1—C4	111.97 (12)	C5—C7—C3	108.48 (12)
C3—N1—C2	124.62 (13)	C10—N2—C9	120.63 (15)
C4—N1—C2	123.38 (13)	C8—N2—C10	120.88 (15)
O4—C1—O3	125.38 (14)	C9—N2—C8	118.48 (14)
O4—C1—C2	116.07 (13)	O5B—C10—N2	118.93 (19)
O3—C1—C2	118.53 (13)	O5B—C10—O5A	119.5 (2)
N1—C2—C1	113.67 (12)	N2—C10—O5A	121.58 (18)
N1—C2—H2A	108.8	N2—C10—H10A	119.2
C1—C2—H2A	108.8	O5A—C10—H10A	119.2
N1—C2—H2B	108.8	O5B—C10—H10B	120.5
C1—C2—H2B	108.8	N2—C10—H10B	120.5
H2A—C2—H2B	107.7	H10A—C10—H10B	120.2
O1—C3—N1	124.69 (14)	N2—C9—H9A	109.5
O1—C3—C7	129.57 (14)	N2—C9—H9B	109.5
N1—C3—C7	105.74 (12)	H9A—C9—H9B	109.5
O2—C4—N1	124.30 (14)	N2—C9—H9C	109.5
O2—C4—C5	128.99 (14)	H9A—C9—H9C	109.5
N1—C4—C5	106.70 (11)	H9B—C9—H9C	109.5
C6—C5—C7	123.04 (13)	N2—C8—H8A	109.5
C6—C5—C4	129.85 (12)	N2—C8—H8B	109.5
C7—C5—C4	107.11 (13)	H8A—C8—H8B	109.5
C7ⁱ—C6—C5	115.11 (12)	N2—C8—H8C	109.5
C7ⁱ—C6—H6	122.4	H8A—C8—H8C	109.5
C5—C6—H6	122.4	H8B—C8—H8C	109.5

C3—N1—C2—C1	−117.78 (16)	N1—C4—C5—C7	−0.77 (14)
C4—N1—C2—C1	64.21 (19)	C7—C5—C6—C7ⁱ	−0.1 (2)
O4—C1—C2—N1	−158.82 (14)	C4—C5—C6—C7ⁱ	−179.65 (13)
O3—C1—C2—N1	22.9 (2)	C6—C5—C7—C6ⁱ	0.1 (2)
C4—N1—C3—O1	179.90 (15)	C4—C5—C7—C6ⁱ	179.75 (12)
C2—N1—C3—O1	1.7 (2)	C6—C5—C7—C3	−178.94 (12)
C4—N1—C3—C7	−0.18 (16)	C4—C5—C7—C3	0.67 (14)
C2—N1—C3—C7	−178.38 (12)	O1—C3—C7—C6ⁱ	0.6 (3)
C3—N1—C4—O2	179.89 (14)	N1—C3—C7—C6ⁱ	−179.32 (13)
C2—N1—C4—O2	−1.9 (2)	O1—C3—C7—C5	179.59 (15)
C3—N1—C4—C5	0.58 (15)	N1—C3—C7—C5	−0.33 (15)
C2—N1—C4—C5	178.81 (12)	C9—N2—C10—O5B	2.6 (3)
O2—C4—C5—C6	−0.5 (2)	C8—N2—C8—O5B	−178.4 (2)
N1—C4—C5—C6	178.80 (13)	C9—N2—C10—O5A	−176.1 (2)
O2—C4—C5—C7	179.96 (15)	C8—N2—C8—O5A	2.9 (3)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O5A	0.82	1.72	2.526 (2)	166
O4—H4B···O5B	0.82	1.70	2.496 (2)	162
C2—H2A···O3ⁱⁱ	0.97	2.41	3.230 (2)	142
C6—H6···O1ⁱⁱⁱ	0.93	2.50	3.414 (2)	166
C9—H9A···O2^iv	0.96	2.57	3.432 (3)	149

Symmetry codes: (ii) −x+1, y−1/2, −z+3/2; (iii) x−1, y, z; (iv) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₈N₂O₈·2C₃H₇NO
M_r	478.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.7470 (15), 9.3100 (19), 16.334 (5)
β (°)	104.02 (3)
V (Å³)	1143.0 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.958, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	6227, 2236, 1910
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.111, 1.06
No. of reflections	2236
No. of parameters	166
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.15

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O5A	0.82	1.72	2.526 (2)	166
O4—H4B···O5B	0.82	1.70	2.496 (2)	162
C2—H2A···O3ⁱ	0.97	2.41	3.230 (2)	142
C6—H6···O1ⁱⁱ	0.93	2.50	3.414 (2)	166
C9—H9A···O2ⁱⁱⁱ	0.96	2.57	3.432 (3)	149

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) x, −y+1/2, z−1/2.

Acknowledgements

This work was supported by the Project for Innovation Teams of Liaoning Province, China (No. 2007 T052), the Project for Provincial Key Laboratories of Liaoning Province, China (No. 2008S104) and the Doctoral Startup Project, Liaoning University.

References

Barooah, N., Sarma, R. J. & Baruah, J. B. (2006). CrystEngComm, 8, 608–615. Web of Science CSD CrossRef CAS Google Scholar
Bhosale, S. V., Jani, C. H. & Langford, S. J. (2008). Chem. Soc. Rev. 37, 331–342. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gabriel, G. J. & Iverson, B. L. (2002). J. Am. Chem. Soc. 124, 15174–15175. Web of Science CrossRef PubMed CAS Google Scholar
Ghosh, S. & Ramakrishnan, S. (2005). Angew. Chem. Int. Ed. 44, 5441–5447. Web of Science CrossRef CAS Google Scholar
Kimizuka, N., Kawasaki, T., Hirata, K. & Kunitake, T. (1995). J. Am. Chem. Soc. 117, 6360–6361. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 10| October 2009| Page o2400

doi:10.1107/S1600536809035107

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,2′-(1,3,5,7-Tetra­oxo-1,2,3,5,6,7-hexa­hydro­pyrrolo[3,4-f]iso­indole-2,6-di­yl)di­acetic acid N,N-di­methyl­formamide disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2′-(1,3,5,7-Tetraoxo-1,2,3,5,6,7-hexahydropyrrolo[3,4-f]isoindole-2,6-diyl)diacetic acid N,N-dimethylformamide disolvate