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Volume 69 
Part 9 
Page o1473  
September 2013  

Received 14 August 2013
Accepted 19 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.005 Å
R = 0.051
wR = 0.148
Data-to-parameter ratio = 15.3
Details
Open access

Ethyl 2-amino-6-(4-bromophenyl)-4-(4-fluorophenyl)cyclohexa-1,3-diene-1-carboxylate

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

In the title compound, C21H19BrFNO2, two independent molecules crystallize in the asymmetric unit. The cyclohexa-1,3-diene ring is in a slightly distorted screw-boat conformation. The dihedral angles between the mean planes of the 4-bromophenyl and 4-fluorophenyl rings are 81.0 (3) and 76.4 (2)° in the two independent molecules. In the crystal, N-H...O hydrogen bonds link the molecules into [100] chains.

Related literature

For cyclohexenones as precursors for functionalized derivatives, see: Samshuddin et al. (2013[Samshuddin, S., Narayana, B., Sarojini, B. K. & Madhu, L. N. (2013). Med. Chem. Res. 22, 3002-3011.]); For 4-bromo-4'-fluorochalcone derivatives, see: Fun et al. (2012a[Fun, H.-K., Chia, T. S., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2680.],b[Fun, H.-K., Loh, W.-S., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o2655-o2656.],c[Fun, H.-K., Loh, W.-S., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012c). Acta Cryst. E68, o2586.]). For related structures, see: Jasinski et al. (2012[Jasinski, J. P., Golen, J. A., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2012). Acta Cryst. E68, o585.]); Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o2917-o2918.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C21H19BrFNO2

  • Mr = 416.28

  • Monoclinic, P 21 /n

  • a = 9.4599 (2) Å

  • b = 23.3634 (5) Å

  • c = 17.2312 (4) Å

  • [beta] = 96.001 (2)°

  • V = 3787.51 (15) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 3.16 mm-1

  • T = 173 K

  • 0.32 × 0.28 × 0.22 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.587, Tmax = 1.000

  • 25170 measured reflections

  • 7427 independent reflections

  • 5973 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.148

  • S = 1.03

  • 7427 reflections

  • 487 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 1.13 e Å-3

  • [Delta][rho]min = -0.53 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1A-H1AA...O2A 0.77 (3) 2.09 (3) 2.698 (4) 136 (3)
N1A-H1AB...O2Bi 0.77 (4) 2.17 (4) 2.915 (4) 162 (4)
N1B-H1BA...O2Aii 0.87 (3) 2.20 (4) 3.044 (3) 163 (3)
N1B-H1BB...O2B 0.85 (4) 2.07 (4) 2.714 (3) 132 (3)
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5341 ).


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. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, 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.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Fun, H.-K., Chia, T. S., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012a). Acta Cryst. E68, o2680.  [CSD] [CrossRef] [details]
Fun, H.-K., Loh, W.-S., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012b). Acta Cryst. E68, o2655-o2656.  [CrossRef] [ChemPort] [details]
Fun, H.-K., Loh, W.-S., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012c). Acta Cryst. E68, o2586.  [CSD] [CrossRef] [details]
Jasinski, J. P., Golen, J. A., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2012). Acta Cryst. E68, o585.  [CSD] [CrossRef] [details]
Kant, R., Gupta, V. K., Kapoor, K., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o2917-o2918.  [CSD] [CrossRef] [ChemPort] [details]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [ISI] [CrossRef] [ChemPort] [details]
Samshuddin, S., Narayana, B., Sarojini, B. K. & Madhu, L. N. (2013). Med. Chem. Res. 22, 3002-3011.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1473  [ doi:10.1107/S1600536813023325 ]

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