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Volume 69 
Part 12 
Pages o1839-o1840  
December 2013  

Received 9 October 2013
Accepted 22 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.055
wR = 0.148
Data-to-parameter ratio = 11.9
Details
Open access

Ethyl 6-(4-chloro­phen­yl)-4-(4-fluoro­phen­yl)-2-oxo­cyclo­hex-3-ene-1-carboxyl­ate

aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India,bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: jjasinski@keene.edu

The asymmetric unit of the title compound, C21H18ClFO3, contains two independent mol­ecules. In one mol­ecule (A), the 4-chloro­phenyl, oxo­cyclo­hex-3-ene, carboxyl­ate, and ethyl groups were refined as disordered over two sets of sites with a 0.684 (5):0.316 (5) ratio. The cyclo­hexene ring in the disordered mol­ecule is in a slightly distorted envelope conformation for the major component (with the C atom bound to the carboxylate group being the flap atom) and in a screw-boat conformation for the minor component. In the ordered mol­ecule (B), the cyclo­hexene ring is in a half-chair conformation. The dihedral angles between the mean planes of the fluoro- and chloro-substituted benzene rings are 89.9 (7) (only the major component is considered for A) and 76.4 (7)° (B). In the crystal, inversion dimers are observed along with weak C-H...O hydrogen bonds, which form chains along [100].

Related literature

For the synthesis and applications of 4,6-diaryl-2-oxo-cyclo­hex-3-ene-1-carboxyl­ate derivatives, see: Ashalatha et al. (2009[Ashalatha, B. V., Narayana, B. & Vijaya Raj, K. K. (2009). Phosphorus Sulfur Silicon, 184, 1904-1919.]); Sreevidya et al. (2010[Sreevidya, T. V., Narayana, B. & Yathirajan, H. S. (2010). Cent. Eur. J. Chem. 8, 171-181.]); Padmavathi et al. (2000[Padmavathi, V., Reddy, B. J. M., Balaiah, A., Reddy, K. V. & Reddy, D. B. (2000). Molecules, 5, 1281-1286.]); Senguttuvan & Nagarajan (2010[Senguttuvan, S. & Nagarajan, S. (2010). Int. J. Chem. 2, 108-112.]); Butcher et al. (2011[Butcher, R. J., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1346-o1347.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For standard bond lengths, see Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For related structures, see: Dutkiewicz et al. (2011a[Dutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011a). Acta Cryst. E67, o334-o335.],b[Dutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011b). Acta Cryst. E67, o336.],c[Dutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011c). Acta Cryst. E67, o445-o446.]); Fun et al. (2010[Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o864-o865.]); Harrison et al. (2010[Harrison, W. T. A., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Sarojini, B. K. (2010). Acta Cryst. E66, o2478.]); Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o2917-o2918.]).

[Scheme 1]

Experimental

Crystal data
  • C21H18ClFO3

  • Mr = 372.80

  • Triclinic, [P \overline 1]

  • a = 11.6611 (5) Å

  • b = 13.1823 (5) Å

  • c = 13.2251 (5) Å

  • [alpha] = 77.250 (3)°

  • [beta] = 87.320 (3)°

  • [gamma] = 67.342 (4)°

  • V = 1828.15 (14) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 2.09 mm-1

  • T = 123 K

  • 0.35 × 0.23 × 0.18 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]) Tmin = 0.508, Tmax = 1.000

  • 13437 measured reflections

  • 7365 independent reflections

  • 6861 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.148

  • S = 1.09

  • 7365 reflections

  • 617 parameters

  • 177 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.68 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8A-H8A...O1B 0.95 2.55 3.478 (3) 167
C2A-H2AA...O1B 0.99 2.44 3.288 (6) 143
C2A-H2AB...O2Bi 0.99 2.56 3.432 (7) 147
C2C-H2CA...O1B 0.99 2.32 3.278 (18) 164
C2C-H2CB...O2Bi 0.99 2.42 3.40 (2) 170
C2B-H2BA...O1Aii 0.99 2.49 3.315 (8) 140
C2B-H2BA...O1Cii 0.99 2.56 3.380 (18) 140
C2B-H2BB...O2Ciii 0.99 2.58 3.436 (10) 145
C8B-H8B...O1Aii 0.95 2.50 3.379 (8) 154
C8B-H8B...O1Cii 0.95 2.54 3.417 (19) 154
C9B-H9B...O2Aii 0.95 2.54 3.274 (6) 134
C14B-H14B...O2Aiii 0.95 2.54 3.247 (5) 131
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y, z+1; (iii) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5662 ).


Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. MS thanks the DST for providing financial help for the research work through an INSPIRE Fellowship. RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, Oxfordshire, England.
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Ashalatha, B. V., Narayana, B. & Vijaya Raj, K. K. (2009). Phosphorus Sulfur Silicon, 184, 1904-1919.  [CrossRef] [ChemPort]
Butcher, R. J., Akkurt, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1346-o1347.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Dutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011a). Acta Cryst. E67, o334-o335.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Dutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011b). Acta Cryst. E67, o336.  [CSD] [CrossRef] [IUCr Journals]
Dutkiewicz, G., Narayana, B., Veena, K., Yathirajan, H. S. & Kubicki, M. (2011c). Acta Cryst. E67, o445-o446.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o864-o865.  [CrossRef] [ChemPort] [IUCr Journals]
Harrison, W. T. A., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Sarojini, B. K. (2010). Acta Cryst. E66, o2478.  [CSD] [CrossRef] [IUCr Journals]
Kant, R., Gupta, V. K., Kapoor, K., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o2917-o2918.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Padmavathi, V., Reddy, B. J. M., Balaiah, A., Reddy, K. V. & Reddy, D. B. (2000). Molecules, 5, 1281-1286.  [CrossRef] [ChemPort]
Senguttuvan, S. & Nagarajan, S. (2010). Int. J. Chem. 2, 108-112.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sreevidya, T. V., Narayana, B. & Yathirajan, H. S. (2010). Cent. Eur. J. Chem. 8, 171-181.  [CSD] [CrossRef]


Acta Cryst (2013). E69, o1839-o1840   [ doi:10.1107/S1600536813031851 ]

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