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Volume 69 
Part 8 
Page o1317  
August 2013  

Received 10 July 2013
Accepted 18 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.065
Data-to-parameter ratio = 15.6
Details
Open access

2-Chloro-3-[(2-oxo-2H-chromen-6-yl)amino]naphthalene-1,4-dione

aDepartamento de Química Inorgânica, Universidade Federal Fluminense, Niterói, CEP 24-020-140, Rio de Janeiro, Brazil
Correspondence e-mail: jagomez@vm.uff.br

In the title compound, C19H10ClNO4, the dihedral angle between the naphthoquinone and coumarin rings is 48.99 (6)°. In the crystal, molecules are linked by strong N-H...O hydrogen bonds into chains with graph-set motif C(6) along [101]. The packing also features [pi]-[pi] stacking interactions between naphthoquinone and coumarin rings [centroid-to-centroid distances = 3.7679 (12) and 3.6180 (13) Å].

Related literature

For related compounds see: Rózsa et al. (1989[Rózsa, Z., Mester, I., Reisch, R. & Szendrei, K. (1989). Planta Med. 55, 68-69.]); Ito et al. (1993[Ito, C., Ono, T., Tanaka, E., Takemura, Y., Nakata, T., Uchida, H., Ju-ichi, M., Omura, M. & Furukawa, H. (1993). Chem. Pharm. Bull. 41, 205-207.]); Ishikawa et al. (1995[Ishikawa, T., Kotake, K. & Ishii, H. (1995). Chem. Pharm. Bull. 43, 1039-1041.]); Padwal et al. (2011[Padwal, J., Lewis, W. & Moody, C. J. (2011). Org. Biomol. Chem. 9, 3484-3493.]). For reference structural data, see: Ibis & Deniz (2012[Ibis, C. & Deniz, N. G. (2012). J. Chem. Sci. 124, 657-667.]); Resende & Gomez (2012[Resende, J. A. L. C. & Gomez, J. A. (2012). Acta Cryst. E68, o2361.]). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C19H10ClNO4

  • Mr = 351.73

  • Monoclinic, C c

  • a = 10.9371 (5) Å

  • b = 10.4462 (5) Å

  • c = 13.5104 (7) Å

  • [beta] = 108.533 (5)°

  • V = 1463.53 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 150 K

  • 0.23 × 0.13 × 0.07 mm

Data collection
  • Oxford Xcalibur Gemini Ultra diffractometer with Atlas detector

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO, Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.947, Tmax = 1

  • 15281 measured reflections

  • 3527 independent reflections

  • 2714 reflections with I > 2[sigma](I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.065

  • S = 0.91

  • 3527 reflections

  • 226 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1217 Friedel pairs

  • Absolute structure parameter: -0.07 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2i 0.86 2.21 3.015 (2) 157
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO, Agilent Technologies Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2446 ).


Acknowledgements

This work was supported by the Brazilian agencies Proppi-UFF, FAPERJ, Scholarship Postgraduate Students Agreement Program - PEC-PG, CAPES/CNPq - Brazil and CAPES. The authors thank the X-ray diffraction laboratory LabCri-UFMG for the data collection, Professor Jackson A. L. C. Resende (IQ-UFF), and Professor M. D. Vargas (IQ-UFF) for her help and encouragement.

References

Agilent (2011). CrysAlis PRO, Agilent Technologies Ltd, Yarnton, Oxfordshire, England.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Ibis, C. & Deniz, N. G. (2012). J. Chem. Sci. 124, 657-667.  [CrossRef] [ChemPort]
Ishikawa, T., Kotake, K. & Ishii, H. (1995). Chem. Pharm. Bull. 43, 1039-1041.  [CrossRef] [ChemPort] [PubMed]
Ito, C., Ono, T., Tanaka, E., Takemura, Y., Nakata, T., Uchida, H., Ju-ichi, M., Omura, M. & Furukawa, H. (1993). Chem. Pharm. Bull. 41, 205-207.  [CrossRef] [ChemPort]
Padwal, J., Lewis, W. & Moody, C. J. (2011). Org. Biomol. Chem. 9, 3484-3493.  [CrossRef] [ChemPort] [PubMed]
Resende, J. A. L. C. & Gomez, J. A. (2012). Acta Cryst. E68, o2361.  [CrossRef] [IUCr Journals]
Rózsa, Z., Mester, I., Reisch, R. & Szendrei, K. (1989). Planta Med. 55, 68-69.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1317  [ doi:10.1107/S1600536813019922 ]

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