1-(2-Hy­droxy­eth­yl)-3-[(2-hy­droxy­eth­yl)amino]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Xie, Z.-X.; Zhao, S.-Y.

doi:10.1107/S1600536811007677

Volume 67
Part 4
Page o854
April 2011

Received 25 February 2011
Accepted 1 March 2011
Online 12 March 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.047
wR = 0.098
Data-to-parameter ratio = 13.7
Details

1-(2-Hydroxyethyl)-3-[(2-hydroxyethyl)amino]-4-(1H-indol-3-yl)-1H-pyrrole-2,5-dione

Zhi-Xiong Xie ^a and Sheng-Yin Zhao ^a ^*

^aCollege of Chemisty, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, People's Republic of China
Correspondence e-mail: syzhao8@dhu.edu.cn

There are four molecules in the asymmetric unit of the title compound, C₁₆H₁₇N₃O₄, in which the dihedral angles between the indole ring system and maleimide ring are 4.5 (3), 8.3 (3), 8.4 (2) and 10.4 (2)°. In the crystal, molecules are linked by numerous N-HO and O-HO hydrogen bonds, generating a three-dimensional network.

Related literature

For general background to indolylmaleimides and their biological properties, see: Vegesna et al. (1998); Hu (1996); Zhao et al. (2008). For the preparation, see: Zhao et al. (2010).

Experimental

Crystal data

C₁₆H₁₇N₃O₄
M_r = 315.33
Triclinic, $[P \overline 1]$
a = 13.0276 (10) Å
b = 14.8150 (11) Å
c = 17.8893 (14) Å
= 90.012 (1)°
= 110.295 (2)°
= 102.187 (2)°
V = 3155.2 (4) Å³
Z = 8
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.43 × 0.33 × 0.27 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003) T_min = 0.594, T_max = 1.000
17464 measured reflections
12193 independent reflections
6708 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.098
S = 0.89
12193 reflections
893 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O12ⁱ	0.86 (3)	2.09 (3)	2.950 (3)	177 (3)
O3-H3O8ⁱⁱ	0.84 (3)	1.93 (3)	2.762 (3)	172 (3)
O4-H4O14ⁱⁱⁱ	0.82 (2)	1.97 (2)	2.770 (2)	163 (3)
N5-H5O16^iv	0.83 (2)	2.22 (2)	3.027 (3)	164 (2)
O7-H7O4^v	0.86 (2)	1.89 (2)	2.755 (3)	175 (3)
O15-H15O1^vi	0.84 (2)	2.22 (2)	2.893 (2)	137 (3)
O15-H15O12^vii	0.84 (2)	2.42 (2)	3.097 (3)	139 (3)
O16-H16O11ⁱ	0.83 (2)	1.96 (2)	2.780 (3)	170 (3)
N3-H3AO6ⁱⁱⁱ	0.87 (2)	2.06 (2)	2.840 (2)	149 (2)
N6-H6AO14	0.84 (2)	2.22 (2)	3.042 (3)	168 (2)
O8-H8AO10^viii	0.85 (2)	1.90 (2)	2.746 (3)	173 (3)
N9-H9AO2^viii	0.89 (2)	1.95 (2)	2.760 (2)	152 (2)
O11-H11AO5ⁱⁱ	0.87 (2)	2.13 (2)	2.935 (2)	154 (3)
O11-H11AO16	0.87 (2)	2.51 (3)	3.033 (3)	120 (3)
O12-H12AO15^ix	0.84 (2)	1.92 (2)	2.739 (2)	168 (3)
N8-H8BO7^x	0.89 (2)	2.09 (2)	2.867 (3)	146 (2)
N11-H11BO3	0.88 (2)	2.17 (2)	2.945 (3)	147 (2)
N12-H12BO10^viii	0.85 (2)	2.10 (2)	2.925 (2)	164 (2)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x-1, y, z; (iii) x, y, z+1; (iv) x+1, y, z; (v) x+1, y, z-1; (vi) -x, -y+2, -z+1; (vii) x, y+1, z; (viii) -x+1, -y+1, -z+1; (ix) -x, -y+1, -z; (x) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5807 ).

Acknowledgements

We thank the Scientific Research Foundation for Returned Overseas Chinese Scholars, State Education Ministry of China (No. [2008]890) for financial support.

References

Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hu, H. (1996). Drug Discov. Today, 1, 438-447.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vegesna, R. V., Wu, H. L., Mong, S. & Crooke, S. T. (1998). Mol. Pharmacol. 33, 537-542.
Zhao, S. Y., Jiang, D. F., Yang, Y. W. & Shao, Z. Y. (2010). Lett. Org. Chem. 7, 144-148.
Zhao, S. Y., Shao, Z. Y., Qin, W. M. & Zhang, D. Q. (2008). Chin. J. Org. Chem. 28, 1128-1137.

organic compounds