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Acta Cryst. (2009). E65, o2975    [ doi:10.1107/S1600536809045437 ]

3,3'-(1,3,5,7-Tetraoxo-2,3,6,7-tetrahydro-1H,5H-pyrrolo[3,4-f]isoindole-2,6-diyl)dipropanoic acid N,N-dimethylformamide disolvate

C.-S. Ling, X. Wang, Y. Liu and Q. Wu

Abstract top

In the title compound, C16H12N2O8·2C3H7NO, the complete tricyclic compound is generated by a crystallographic centre of symmetry. In the crystal, the tricycle is linked to two adjacent N,N-dimethylformamide solvent molecules by O-H...O hydrogen bonds.

Related literature top

For a related structure and background, see: Wang & Wei (2005).

Experimental top

3-Bromopropanoic acid (2 mmol, 0.306 g) and pyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone (1 mmol, 0.360 g) were dissolved in 20 ml of the mixed solvent of N,N-dimethylformamide and water in a ratio of 1:2 (v/v). The mixture was heated in a Teflon-lined steel autoclave inside a programmable electric furnace at 353 K for three days. After cooling the autoclave to room temperature, colourless slabs of (I) were obtained.

Refinement top

H9A aom was located by Fourier map, other H atoms were geometrically placed with C—H = 0.93–0.97 Å and O—H = 0.82 Å, and were refined as riding with Uiso(H)=1.2Ueq(Cmethylene and C in phenyl ring) and Uiso(H)=1.5Ueq(O and Cmethyl).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level.
3,3'-(1,3,5,7-Tetraoxo-2,3,6,7-tetrahydro-1H,5H- pyrrolo[3,4-f]isoindole-2,6-diyl)dipropanoic acid N,N-dimethylformamide solvate top
Crystal data top
C16H12N2O8·2C3H7NOF(000) = 532
Mr = 506.47Dx = 1.377 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2660 reflections
a = 12.542 (8) Åθ = 3.0–23.7°
b = 8.611 (6) ŵ = 0.11 mm−1
c = 12.902 (9) ÅT = 296 K
β = 118.774 (8)°Slab, colourless
V = 1221.3 (14) Å30.33 × 0.31 × 0.10 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer		1745 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
graphiteθmax = 26.0°, θmin = 1.9°
ω scansh = −15→15
12363 measured reflectionsk = −10→10
2386 independent reflectionsl = −15→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0551P)2 + 0.5597P]
where P = (Fo2 + 2Fc2)/3
2386 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 0.44 e Å−3
15 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C16H12N2O8·2C3H7NOV = 1221.3 (14) Å3
Mr = 506.47Z = 2
Monoclinic, P21/cMo Kα radiation
a = 12.542 (8) ŵ = 0.11 mm−1
b = 8.611 (6) ÅT = 296 K
c = 12.902 (9) Å0.33 × 0.31 × 0.10 mm
β = 118.774 (8)°
Data collection top
Bruker SMART CCD
diffractometer		1745 reflections with I > 2σ(I)
12363 measured reflectionsRint = 0.037
2386 independent reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133Δρmax = 0.44 e Å−3
S = 1.06Δρmin = −0.29 e Å−3
2386 reflectionsAbsolute structure: ?
167 parametersFlack parameter: ?
15 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
O10.2286 (2)0.3041 (3)−0.14930 (17)0.0847 (7)
O20.3228 (2)0.5093 (3)−0.16182 (17)0.0896 (8)
H20.28610.4876−0.23240.134*
O30.22033 (16)0.5402 (2)0.20189 (14)0.0502 (5)
O40.55406 (18)0.2430 (2)0.29251 (15)0.0579 (5)
O50.2066 (2)1.0088 (2)1.11020 (15)0.0651 (6)
C10.2949 (2)0.4100 (3)−0.1032 (2)0.0487 (6)
C20.3578 (3)0.4407 (4)0.0263 (2)0.0575 (7)
H2B0.34070.54650.03950.069*
H2C0.44490.43210.05640.069*
C30.3212 (3)0.3327 (3)0.09466 (19)0.0479 (6)
H3A0.23320.33200.05970.057*
H3B0.34750.22810.09030.057*
C40.3193 (2)0.4830 (3)0.26018 (19)0.0388 (5)
C50.4876 (2)0.3319 (3)0.30588 (19)0.0403 (5)
C60.5071 (2)0.4122 (3)0.41634 (19)0.0366 (5)
C70.6041 (2)0.4039 (3)0.5291 (2)0.0396 (5)
H7A0.67140.34120.54820.048*
C80.5939 (2)0.4955 (3)0.61186 (18)0.0368 (5)
C90.1607 (3)0.8835 (4)1.0674 (2)0.0522 (7)
H9A0.170 (3)0.794 (4)1.119 (3)0.066 (8)*
C100.0679 (3)0.9775 (4)0.8676 (3)0.0717 (9)
H10A0.10901.07100.90710.108*
H10B−0.01820.99580.82540.108*
H10C0.09550.94620.81310.108*
C110.0398 (4)0.7052 (5)0.9101 (4)0.1117 (16)
H11A0.06430.63470.97530.168*
H11B0.06630.66620.85660.168*
H11C−0.04720.71480.86950.168*
N10.37472 (18)0.3802 (2)0.21817 (16)0.0416 (5)
N20.0942 (2)0.8560 (3)0.95392 (19)0.0558 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1149 (18)0.0799 (15)0.0394 (10)−0.0332 (14)0.0212 (11)−0.0087 (10)
O20.1066 (17)0.1158 (18)0.0353 (10)−0.0460 (15)0.0254 (11)0.0011 (11)
O30.0456 (10)0.0599 (11)0.0371 (9)0.0041 (9)0.0135 (8)0.0081 (8)
O40.0728 (13)0.0580 (11)0.0467 (10)0.0166 (10)0.0319 (10)−0.0008 (8)
O50.0889 (15)0.0617 (12)0.0383 (10)−0.0119 (11)0.0253 (10)−0.0033 (9)
C10.0564 (14)0.0563 (14)0.0308 (11)−0.0061 (12)0.0190 (11)−0.0015 (10)
C20.0695 (18)0.0686 (18)0.0319 (13)−0.0228 (15)0.0224 (13)−0.0066 (12)
C30.0612 (16)0.0484 (14)0.0290 (12)−0.0080 (12)0.0178 (11)−0.0050 (10)
C40.0435 (14)0.0410 (13)0.0314 (11)−0.0031 (11)0.0176 (11)0.0046 (10)
C50.0514 (14)0.0383 (12)0.0341 (12)0.0009 (11)0.0228 (11)0.0013 (9)
C60.0452 (13)0.0361 (12)0.0317 (11)0.0017 (10)0.0211 (10)0.0030 (9)
C70.0409 (13)0.0434 (13)0.0352 (12)0.0071 (10)0.0188 (10)0.0046 (10)
C80.0417 (13)0.0408 (12)0.0287 (11)0.0005 (10)0.0176 (10)0.0044 (9)
C90.0573 (17)0.0564 (17)0.0404 (14)0.0010 (13)0.0215 (13)0.0058 (13)
C100.0654 (19)0.104 (3)0.0398 (15)0.0021 (18)0.0207 (14)0.0130 (15)
C110.110 (3)0.078 (3)0.088 (3)−0.016 (2)0.001 (2)−0.017 (2)
N10.0513 (12)0.0442 (11)0.0278 (9)−0.0014 (9)0.0180 (9)−0.0002 (8)
N20.0534 (13)0.0621 (14)0.0408 (12)−0.0010 (11)0.0139 (10)−0.0024 (10)
Geometric parameters (Å, °) top
O1—C11.184 (3)C6—C71.378 (3)
O2—C11.296 (3)C6—C8i1.387 (3)
O2—H20.8200C7—C81.382 (3)
O3—C41.204 (3)C7—H7A0.9300
O4—C51.203 (3)C8—C6i1.387 (3)
O5—C91.222 (3)C8—C4i1.488 (3)
C1—C21.488 (3)C9—N21.311 (3)
C2—C31.498 (4)C9—H9A0.99 (3)
C2—H2B0.9700C10—N21.445 (4)
C2—H2C0.9700C10—H10A0.9600
C3—N11.458 (3)C10—H10B0.9600
C3—H3A0.9700C10—H10C0.9600
C3—H3B0.9700C11—N21.449 (4)
C4—N11.387 (3)C11—H11A0.9600
C4—C8i1.488 (3)C11—H11B0.9600
C5—N11.384 (3)C11—H11C0.9600
C5—C61.495 (3)
C1—O2—H2109.5C6—C7—H7A122.5
O1—C1—O2122.5 (2)C8—C7—H7A122.5
O1—C1—C2124.4 (2)C7—C8—C6i122.4 (2)
O2—C1—C2113.1 (2)C7—C8—C4i129.6 (2)
C1—C2—C3113.8 (2)C6i—C8—C4i107.94 (19)
C1—C2—H2B108.8O5—C9—N2124.9 (3)
C3—C2—H2B108.8O5—C9—H9A120.7 (17)
C1—C2—H2C108.8N2—C9—H9A114.4 (18)
C3—C2—H2C108.8N2—C10—H10A109.5
H2B—C2—H2C107.7N2—C10—H10B109.5
N1—C3—C2111.0 (2)H10A—C10—H10B109.5
N1—C3—H3A109.4N2—C10—H10C109.5
C2—C3—H3A109.4H10A—C10—H10C109.5
N1—C3—H3B109.4H10B—C10—H10C109.5
C2—C3—H3B109.4N2—C11—H11A109.5
H3A—C3—H3B108.0N2—C11—H11B109.5
O3—C4—N1125.2 (2)H11A—C11—H11B109.5
O3—C4—C8i128.8 (2)N2—C11—H11C109.5
N1—C4—C8i106.0 (2)H11A—C11—H11C109.5
O4—C5—N1125.5 (2)H11B—C11—H11C109.5
O4—C5—C6128.6 (2)C5—N1—C4112.35 (19)
N1—C5—C6105.9 (2)C5—N1—C3124.1 (2)
C7—C6—C8i122.5 (2)C4—N1—C3123.5 (2)
C7—C6—C5129.7 (2)C9—N2—C10121.1 (3)
C8i—C6—C5107.8 (2)C9—N2—C11121.6 (3)
C6—C7—C8115.0 (2)C10—N2—C11117.3 (3)
O1—C1—C2—C3−5.3 (4)C6—C5—N1—C40.0 (3)
O2—C1—C2—C3176.6 (3)O4—C5—N1—C3−1.9 (4)
C1—C2—C3—N1−173.2 (2)C6—C5—N1—C3178.2 (2)
O4—C5—C6—C7−0.5 (4)O3—C4—N1—C5−179.1 (2)
N1—C5—C6—C7179.4 (2)C8i—C4—N1—C50.6 (2)
O4—C5—C6—C8i179.4 (2)O3—C4—N1—C32.7 (4)
N1—C5—C6—C8i−0.7 (2)C8i—C4—N1—C3−177.6 (2)
C8i—C6—C7—C8−0.7 (4)C2—C3—N1—C5−88.7 (3)
C5—C6—C7—C8179.2 (2)C2—C3—N1—C489.2 (3)
C6—C7—C8—C6i0.7 (4)O5—C9—N2—C10−0.8 (5)
C6—C7—C8—C4i−179.0 (2)O5—C9—N2—C11−178.1 (4)
O4—C5—N1—C4180.0 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O5ii0.821.782.583 (3)166
Symmetry codes: (ii) x, −y+3/2, z−3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O5i0.821.782.583 (3)166
Symmetry codes: (i) x, −y+3/2, z−3/2.
Acknowledgements top

This work was supported by the Basic Research Foundation for Natural Science of Henan University.

references
References top

Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Wang, Z.-L. & Wei, L.-H. (2005). Acta Cryst. E61, o3129–o3130.