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

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

doi:10.1107/S1600536809045437

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o2975

doi:10.1107/S1600536809045437

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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

Chun-Sheng Ling,^a Xu Wang,^a Yun Liu ^a and Qiang Wu ^a ^*

^aInstitute of Pharmacy, Henan University, Kaifeng 475004, People's Republic of China
^*Correspondence e-mail: ysywu@126.com

(Received 24 October 2009; accepted 29 October 2009; online 4 November 2009)

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

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

Experimental

Crystal data

C₁₆H₁₂N₂O₈·2C₃H₇NO
M_r = 506.47
Monoclinic, P 2₁ /c
a = 12.542 (8) Å
b = 8.611 (6) Å
c = 12.902 (9) Å
β = 118.774 (8)°
V = 1221.3 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.33 × 0.31 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: none
12363 measured reflections
2386 independent reflections
1745 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.133
S = 1.06
2386 reflections
167 parameters
15 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O5ⁱ	0.82	1.78	2.583 (3)	166
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045437/hb5179sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045437/hb5179Isup2.hkl

checkCIF report

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.

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

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

C₁₆H₁₂N₂O₈·2C₃H₇NO	F(000) = 532
M_r = 506.47	D_x = 1.377 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2660 reflections
a = 12.542 (8) Å	θ = 3.0–23.7°
b = 8.611 (6) Å	µ = 0.11 mm⁻¹
c = 12.902 (9) Å	T = 296 K
β = 118.774 (8)°	Slab, colourless
V = 1221.3 (14) Å³	0.33 × 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 tube	R_int = 0.037
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
ω scans	h = −15→15
12363 measured reflections	k = −10→10
2386 independent reflections	l = −15→15

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0551P)² + 0.5597P] where P = (F_o² + 2F_c²)/3
2386 reflections	(Δ/σ)_max < 0.001
167 parameters	Δρ_max = 0.44 e Å⁻³
15 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₆H₁₂N₂O₈·2C₃H₇NO	V = 1221.3 (14) Å³
M_r = 506.47	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.542 (8) Å	µ = 0.11 mm⁻¹
b = 8.611 (6) Å	T = 296 K
c = 12.902 (9) Å	0.33 × 0.31 × 0.10 mm
β = 118.774 (8)°

Data collection top

Bruker SMART CCD diffractometer	1745 reflections with I > 2σ(I)
12363 measured reflections	R_int = 0.037
2386 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	15 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.44 e Å⁻³
2386 reflections	Δρ_min = −0.30 e Å⁻³
167 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	0.2286 (2)	0.3041 (3)	−0.14930 (17)	0.0847 (7)
O2	0.3228 (2)	0.5093 (3)	−0.16182 (17)	0.0896 (8)
H2	0.2861	0.4876	−0.2324	0.134*
O3	0.22033 (16)	0.5402 (2)	0.20189 (14)	0.0502 (5)
O4	0.55406 (18)	0.2430 (2)	0.29251 (15)	0.0579 (5)
O5	0.2066 (2)	1.0088 (2)	1.11020 (15)	0.0651 (6)
C1	0.2949 (2)	0.4100 (3)	−0.1032 (2)	0.0487 (6)
C2	0.3578 (3)	0.4407 (4)	0.0263 (2)	0.0575 (7)
H2B	0.3407	0.5465	0.0395	0.069*
H2C	0.4449	0.4321	0.0564	0.069*
C3	0.3212 (3)	0.3327 (3)	0.09466 (19)	0.0479 (6)
H3A	0.2332	0.3320	0.0597	0.057*
H3B	0.3475	0.2281	0.0903	0.057*
C4	0.3193 (2)	0.4830 (3)	0.26018 (19)	0.0388 (5)
C5	0.4876 (2)	0.3319 (3)	0.30588 (19)	0.0403 (5)
C6	0.5071 (2)	0.4122 (3)	0.41634 (19)	0.0366 (5)
C7	0.6041 (2)	0.4039 (3)	0.5291 (2)	0.0396 (5)
H7A	0.6714	0.3412	0.5482	0.048*
C8	0.5939 (2)	0.4955 (3)	0.61186 (18)	0.0368 (5)
C9	0.1607 (3)	0.8835 (4)	1.0674 (2)	0.0522 (7)
H9A	0.170 (3)	0.794 (4)	1.119 (3)	0.066 (8)*
C10	0.0679 (3)	0.9775 (4)	0.8676 (3)	0.0717 (9)
H10A	0.1090	1.0710	0.9071	0.108*
H10B	−0.0182	0.9958	0.8254	0.108*
H10C	0.0955	0.9462	0.8131	0.108*
C11	0.0398 (4)	0.7052 (5)	0.9101 (4)	0.1117 (16)
H11A	0.0643	0.6347	0.9753	0.168*
H11B	0.0663	0.6662	0.8566	0.168*
H11C	−0.0472	0.7148	0.8695	0.168*
N1	0.37472 (18)	0.3802 (2)	0.21817 (16)	0.0416 (5)
N2	0.0942 (2)	0.8560 (3)	0.95392 (19)	0.0558 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1149 (18)	0.0799 (15)	0.0394 (10)	−0.0332 (14)	0.0212 (11)	−0.0087 (10)
O2	0.1066 (17)	0.1158 (18)	0.0353 (10)	−0.0460 (15)	0.0254 (11)	0.0011 (11)
O3	0.0456 (10)	0.0599 (11)	0.0371 (9)	0.0041 (9)	0.0135 (8)	0.0081 (8)
O4	0.0728 (13)	0.0580 (11)	0.0467 (10)	0.0166 (10)	0.0319 (10)	−0.0008 (8)
O5	0.0889 (15)	0.0617 (12)	0.0383 (10)	−0.0119 (11)	0.0253 (10)	−0.0033 (9)
C1	0.0564 (14)	0.0563 (14)	0.0308 (11)	−0.0061 (12)	0.0190 (11)	−0.0015 (10)
C2	0.0695 (18)	0.0686 (18)	0.0319 (13)	−0.0228 (15)	0.0224 (13)	−0.0066 (12)
C3	0.0612 (16)	0.0484 (14)	0.0290 (12)	−0.0080 (12)	0.0178 (11)	−0.0050 (10)
C4	0.0435 (14)	0.0410 (13)	0.0314 (11)	−0.0031 (11)	0.0176 (11)	0.0046 (10)
C5	0.0514 (14)	0.0383 (12)	0.0341 (12)	0.0009 (11)	0.0228 (11)	0.0013 (9)
C6	0.0452 (13)	0.0361 (12)	0.0317 (11)	0.0017 (10)	0.0211 (10)	0.0030 (9)
C7	0.0409 (13)	0.0434 (13)	0.0352 (12)	0.0071 (10)	0.0188 (10)	0.0046 (10)
C8	0.0417 (13)	0.0408 (12)	0.0287 (11)	0.0005 (10)	0.0176 (10)	0.0044 (9)
C9	0.0573 (17)	0.0564 (17)	0.0404 (14)	0.0010 (13)	0.0215 (13)	0.0058 (13)
C10	0.0654 (19)	0.104 (3)	0.0398 (15)	0.0021 (18)	0.0207 (14)	0.0130 (15)
C11	0.110 (3)	0.078 (3)	0.088 (3)	−0.016 (2)	0.001 (2)	−0.017 (2)
N1	0.0513 (12)	0.0442 (11)	0.0278 (9)	−0.0014 (9)	0.0180 (9)	−0.0002 (8)
N2	0.0534 (13)	0.0621 (14)	0.0408 (12)	−0.0010 (11)	0.0139 (10)	−0.0024 (10)

Geometric parameters (Å, º) top

O1—C1	1.184 (3)	C6—C7	1.378 (3)
O2—C1	1.296 (3)	C6—C8ⁱ	1.387 (3)
O2—H2	0.8200	C7—C8	1.382 (3)
O3—C4	1.204 (3)	C7—H7A	0.9300
O4—C5	1.203 (3)	C8—C6ⁱ	1.387 (3)
O5—C9	1.222 (3)	C8—C4ⁱ	1.488 (3)
C1—C2	1.488 (3)	C9—N2	1.311 (3)
C2—C3	1.498 (4)	C9—H9A	0.99 (3)
C2—H2B	0.9700	C10—N2	1.445 (4)
C2—H2C	0.9700	C10—H10A	0.9600
C3—N1	1.458 (3)	C10—H10B	0.9600
C3—H3A	0.9700	C10—H10C	0.9600
C3—H3B	0.9700	C11—N2	1.449 (4)
C4—N1	1.387 (3)	C11—H11A	0.9600
C4—C8ⁱ	1.488 (3)	C11—H11B	0.9600
C5—N1	1.384 (3)	C11—H11C	0.9600
C5—C6	1.495 (3)

C1—O2—H2	109.5	C6—C7—H7A	122.5
O1—C1—O2	122.5 (2)	C8—C7—H7A	122.5
O1—C1—C2	124.4 (2)	C7—C8—C6ⁱ	122.4 (2)
O2—C1—C2	113.1 (2)	C7—C8—C4ⁱ	129.6 (2)
C1—C2—C3	113.8 (2)	C6ⁱ—C8—C4ⁱ	107.94 (19)
C1—C2—H2B	108.8	O5—C9—N2	124.9 (3)
C3—C2—H2B	108.8	O5—C9—H9A	120.7 (17)
C1—C2—H2C	108.8	N2—C9—H9A	114.4 (18)
C3—C2—H2C	108.8	N2—C10—H10A	109.5
H2B—C2—H2C	107.7	N2—C10—H10B	109.5
N1—C3—C2	111.0 (2)	H10A—C10—H10B	109.5
N1—C3—H3A	109.4	N2—C10—H10C	109.5
C2—C3—H3A	109.4	H10A—C10—H10C	109.5
N1—C3—H3B	109.4	H10B—C10—H10C	109.5
C2—C3—H3B	109.4	N2—C11—H11A	109.5
H3A—C3—H3B	108.0	N2—C11—H11B	109.5
O3—C4—N1	125.2 (2)	H11A—C11—H11B	109.5
O3—C4—C8ⁱ	128.8 (2)	N2—C11—H11C	109.5
N1—C4—C8ⁱ	106.0 (2)	H11A—C11—H11C	109.5
O4—C5—N1	125.5 (2)	H11B—C11—H11C	109.5
O4—C5—C6	128.6 (2)	C5—N1—C4	112.35 (19)
N1—C5—C6	105.9 (2)	C5—N1—C3	124.1 (2)
C7—C6—C8ⁱ	122.5 (2)	C4—N1—C3	123.5 (2)
C7—C6—C5	129.7 (2)	C9—N2—C10	121.1 (3)
C8ⁱ—C6—C5	107.8 (2)	C9—N2—C11	121.6 (3)
C6—C7—C8	115.0 (2)	C10—N2—C11	117.3 (3)

O1—C1—C2—C3	−5.3 (4)	C6—C5—N1—C4	0.0 (3)
O2—C1—C2—C3	176.6 (3)	O4—C5—N1—C3	−1.9 (4)
C1—C2—C3—N1	−173.2 (2)	C6—C5—N1—C3	178.2 (2)
O4—C5—C6—C7	−0.5 (4)	O3—C4—N1—C5	−179.1 (2)
N1—C5—C6—C7	179.4 (2)	C8ⁱ—C4—N1—C5	0.6 (2)
O4—C5—C6—C8ⁱ	179.4 (2)	O3—C4—N1—C3	2.7 (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—C8	179.2 (2)	C2—C3—N1—C4	89.2 (3)
C6—C7—C8—C6ⁱ	0.7 (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—C4	180.0 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱⁱ	0.82	1.78	2.583 (3)	166

Symmetry code: (ii) x, −y+3/2, z−3/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O₈·2C₃H₇NO
M_r	506.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.542 (8), 8.611 (6), 12.902 (9)
β (°)	118.774 (8)
V (Å³)	1221.3 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.33 × 0.31 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12363, 2386, 1745
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.133, 1.06
No. of reflections	2386
No. of parameters	167
No. of restraints	15
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.30

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱ	0.82	1.78	2.583 (3)	166

Symmetry code: (i) x, −y+3/2, z−3/2.

Acknowledgements

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

References

Bruker (2001). SAINT-Plus and SMART. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Z.-L. & Wei, L.-H. (2005). Acta Cryst. E61, o3129–o3130. Web of Science CSD CrossRef IUCr Journals Google Scholar

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