3′-Hy­droxy­methyl-1′-methyl-3′-nitro-4′-(o-tol­yl)spiro­[indoline-3,2′-pyrrolidin]-2-one

Gangadharan, R.; SethuSankar, K.; Bakthadoss, M.; Sivakumar, N.; Velmurugan, D.

doi:10.1107/S1600536810041917

Volume 66
Part 11
Page o2935
November 2010

Received 5 October 2010
Accepted 16 October 2010
Online 23 October 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.131
Data-to-parameter ratio = 18.7
Details

3'-Hydroxymethyl-1'-methyl-3'-nitro-4'-(o-tolyl)spiro[indoline-3,2'-pyrrolidin]-2-one

Rajeswari Gangadharan,^a K. SethuSankar,^b ^* Manickam Bakthadoss,^c Nagappan Sivakumar ^c and D. Velmurugan ^d

^aDepartment of Physics, Ethiraj College for Women (Autonomous), Chennai 600 008, India,^bDepartment of Physics, R.K.M. Vivekananda College (Autonomous), Chennai 600 004, India,^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^dCentre for Advanced Studies in Crystallography, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: ksethusankar@yahoo.co.in

The title compound, C₂₀H₂₁N₃O₄, crystallizes with two molecules in the asymmetric unit. In both molecules, the pyrrolidine ring adopts an envelope conformation. The crystal structure is stabilized by intermolecular C-HO, N-HO and O-HO hydrogen bonds.

Related literature

For ring puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₂₀H₂₁N₃O₄
M_r = 367.40
Triclinic, $[P \overline 1]$
a = 10.8757 (18) Å
b = 13.625 (2) Å
c = 13.656 (2) Å
= 66.116 (8)°
= 83.715 (8)°
= 78.991 (9)°
V = 1814.9 (5) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.30 × 0.26 × 0.20 mm

Data collection

Bruker APEXII CCD area detector diffractometer
32702 measured reflections
9209 independent reflections
5980 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.131
S = 1.03
9209 reflections
493 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO3ⁱ	0.86	2.00	2.782 (2)	151
O3-H3BO7ⁱⁱ	0.82	2.11	2.7769 (17)	139
N5-H5O8ⁱⁱⁱ	0.86	2.39	3.0064 (19)	129
O7-H7O4^iv	0.82	2.24	2.9356 (19)	142
C8-H8O1^v	0.98	2.40	3.164 (2)	135
C33-H33AO2ⁱⁱ	0.97	2.59	3.209 (2)	122
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) x-1, y-1, z; (v) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5370 ).

Acknowledgements

RG and KS thank the Technology Business Incubator (TBI), CAS in Crystallography and Biophysics, University of Madras, Chennai, and the Department of Science and Technology (DST) for the data collection.

References

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds