3,3-Dieth­oxy-5-fluoro-2,3-dihydro-1H-indol-2-one

Bari, A.; Al-Obaid, A.M.; Saeed, A.S.; Ng, S.W.

doi:10.1107/S1600536812001857

Volume 68
Part 2
Page o487
February 2012

Received 8 January 2012
Accepted 15 January 2012
Online 21 January 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.100
Data-to-parameter ratio = 14.8
Details

3,3-Diethoxy-5-fluoro-2,3-dihydro-1H-indol-2-one

Ahmed Bari,^a Abdulrahman M. Al-Obaid,^a Ali Syed Saeed ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia,^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: seikweng@um.edu.my

The title ketal, C₁₂H₁₄FNO₃, crystallized with two independent molecules in the asymmetric unit. In each molecule the fused ring system is essentially planar [maximum deviations of 0.0169 (11) and 0.0402 (13) Å]. The molecules are each hydrogen bonded across a center of inversion into a dimer; adjacent dimers are linked by another N-HO hydrogen bond, forming a chain running along [100].

Related literature

For 3,3-dimethoxyindolin-2-one, see: De & Kitagawa (1991).

Experimental

Crystal data

C₁₂H₁₄FNO₃
M_r = 239.24
Triclinic, $[P \overline 1]$
a = 9.3218 (6) Å
b = 9.4320 (5) Å
c = 14.1544 (8) Å
= 100.475 (5)°
= 104.453 (5)°
= 90.238 (5)°
V = 1183.43 (12) Å³
Z = 4
Cu K radiation
= 0.90 mm^-1
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T_min = 0.773, T_max = 0.915
8022 measured reflections
4661 independent reflections
4067 reflections with I > 2(I)
R_int = 0.018

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.100
S = 1.04
4661 reflections
315 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O4	0.85 (2)	2.30 (2)	3.010 (2)	142 (2)
N1-H1O1ⁱ	0.85 (2)	2.34 (2)	3.043 (1)	141 (2)
N2-H2O1ⁱⁱ	0.87 (2)	2.28 (2)	3.002 (2)	140 (2)
N2-H2O4ⁱⁱⁱ	0.87 (2)	2.33 (2)	3.057 (2)	142 (2)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5445 ).

Acknowledgements

We thank the Research Center of Pharmacy, King Saud University (project No. 080149) and the Ministry of Higher Education of Malaysia (grant No. UM·C/HIR/MOHE/SC/12) for supporting this study.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
De, A. & Kitagawa, Y. (1991). Acta Cryst. C47, 2384-2386.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds