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Volume 70 
Part 5 
Pages o579-o580  
May 2014  

Received 17 March 2014
Accepted 10 April 2014
Online 18 April 2014

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.038
wR = 0.105
Data-to-parameter ratio = 13.8
Details
Open access

4-(4-Bromo­phen­yl)-7,7-dimethyl-2-methyl­amino-3-nitro-7,8-di­hydro-4H-chromen-5(6H)-one including an unknown solvate

aSri Ram Engineering College, Chennai 602 024, India,bDepartment of Chemistry, Pondichery University, Pondichery 605 014, India, and cDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C18H19BrN2O4, the chromene unit is not quite planar (r.m.s. deviation = 0.199 Å), with the methyl C atoms lying 0.027 (4) and 1.929 (4) Å from the mean plane of the chromene unit. The six-membered carbocyclic ring of the chromene moiety adopts an envelope conformation, with the dimethyl-substituted C atom as the flap. The methyl­amine and nitro groups are slightly twisted from the chromene moiety, with C-N-C-O and O-N-C-C torsion angles of 2.7 (4) and -0.4 (4)°, respectively. The dihedral angle between the mean plane of the chromene unit and the benzene ring is 85.61 (13)°. An intra­molecular N-H...O hydrogen bond generates an S(6) ring motif, which stabilizes the mol­ecular conformation. In the crystal, mol­ecules are linked via N-H...O hydrogen bonds, forming hexa­gonal rings lying parallel to the ab plane. A region of disordered electron density, most probably disordered ethanol solvent mol­ecules, occupying voids of ca 432 Å3 for an electron count of 158, was treated using the SQUEEZE routine in PLATON [Spek (2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]). Acta Cryst. D65, 148-155]. Their formula mass and unit-cell characteristics were not taken into account during refinement.

Related literature

For the biological and pharmacological properties of chromene and chromene derivatives, see: Thomas & Zachariah (2013[Thomas, N. & Zachariah, S. M. (2013). Asian J. Pharm. Clin. Res. 6 (Suppl. 2), 11-15.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For a related structure, see: Narayanan et al. (2013[Narayanan, P., Kamalraja, J., Perumal, P. T. & Sethusankar, K. (2013). Acta Cryst. E69, o931-o932.]).

[Scheme 1]

Experimental

Crystal data
  • C18H19BrN2O4

  • Mr = 407.26

  • Trigonal, [R \overline 3]

  • a = 24.2105 (13) Å

  • c = 15.7745 (9) Å

  • V = 8007.4 (8) Å3

  • Z = 18

  • Mo K[alpha] radiation

  • [mu] = 2.34 mm-1

  • T = 293 K

  • 0.35 × 0.30 × 0.30 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.446, Tmax = 0.496

  • 25281 measured reflections

  • 3206 independent reflections

  • 2565 reflections with I > 2[sigma](I)

  • Rint = 0.035

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.105

  • S = 1.09

  • 3206 reflections

  • 233 parameters

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

  • [Delta][rho]max = 0.68 e Å-3

  • [Delta][rho]min = -0.61 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2N...O3 0.83 (3) 2.00 (3) 2.618 (3) 130 (3)
N2-H2N...O4i 0.83 (3) 2.38 (3) 2.969 (3) 129 (3)
Symmetry code: (i) [x-y+{\script{1\over 3}}, x-{\script{1\over 3}}, -z+{\script{2\over 3}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supporting information for this paper is available from the IUCr electronic archives (Reference: SU2714 ).


Acknowledgements

The authors gratefully acknowledge Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Narayanan, P., Kamalraja, J., Perumal, P. T. & Sethusankar, K. (2013). Acta Cryst. E69, o931-o932.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Thomas, N. & Zachariah, S. M. (2013). Asian J. Pharm. Clin. Res. 6 (Suppl. 2), 11-15.


Acta Cryst (2014). E70, o579-o580   [ doi:10.1107/S1600536814007983 ]

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