2,2'-(1,3,5,7-Tetra-oxo-1,2,3,5,6,7-hexa-hydro-pyrrolo[3,4-f]isoindole-2,6-di-yl)diacetic acid N,N-dimethyl-formamide disolvate.

The asymmetric unit of the title compound, C(14)H(8)N(2)O(8)·2C(3)H(7)NO or L·2DMF (DMF = N,N-dimethyl-formamide), contains one half of the centrosymmetric mol-ecule L and one solvent mol-ecule, which is disordered between two orientations in a 0.555 (4):0.445 (4) ratio. Inter-molecular O-H⋯O hydrogen bonds link one L and two DMF mol-ecules into a centrosymmetric hydrogen-bonded cluster. The crystal packing is further stabilized by weak inter-molecular 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 = 478.42

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.06

2236 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H8N2O8·2C3H7NO	F(000) = 500
Mr = 478.42	Dx = 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

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

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(Fo2) + (0.0528P)2 + 0.2565P] where P = (Fo2 + 2Fc2)/3
2236 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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···O2iv	0.96	2.57	3.432 (3)	149

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) ; (ii) ; (iii) .