1-(2-Furo­yl)-3-(2-meth­oxy-4-nitro­phen­yl)thio­urea

Pratap, S.; Singh, D.P.; Gupta, S.K.; Yildirim, S. Ö.; Butcher, R.J.

doi:10.1107/S1600536813002894

Volume 69
Part 3
Pages o330-o331
March 2013

Received 5 December 2012
Accepted 28 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.003 Å
R = 0.046
wR = 0.134
Data-to-parameter ratio = 13.5
Details

1-(2-Furoyl)-3-(2-methoxy-4-nitrophenyl)thiourea

Seema Pratap,^a Durga P. Singh,^a Sushil K. Gupta,^b Sema Öztürk Yildirim ^c and Ray J. Butcher ^d ^*

^aDepartment of Chemistry, M. M. V., Banaras Hindu University, Varanasi 221 005, India,^bSchool of Studies in Chemistry, Jiwaji University, Gwalior 474 011, India,^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
Correspondence e-mail: rbutcher99@yahoo.com

The asymmetric unit of the title compound, C₁₃H₁₁N₃O₅S, contains two independent molecules, which are linked by a pair of intermolecular N-HS hydrogen bonds, forming an R₂²(8) ring motif. The central thiourea core forms dihedral angles of 3.02 (12) and 14.00 (10)° with the essentially planar furoyl groups [maximum deviations = 0.030 (2) and 0.057 (2) Å] in the two molecules and dihedral angles of 2.43 (13) and 8.03 (12)° with the benzene rings. The dihedral angles between the furoyl and benzene rings in the two molecules are 3.97 (10) and 5.98 (9)°. The trans-cis geometry of the thiourea group is stabilized by three intramolecular N-HO hydrogen bonds involving carbonyl and methoxy O atoms with the H atom of the cis-thioamide group and between furan O atom and the other thioamide H atom. There is also a weak intramolecular C-HS interaction in each molecule.

Related literature

For background to anion receptors, see: Doyle & Jacobsen (2007); Gale et al. (2008); Svetlana (2007). For aroyl thioureas as ionophores, see: Wilson et al. (2010); Pérez et al. (2008) and as catalysts, see: Yang et al. (2004); Dai et al. (2004). For related structures, see: Koch (2001); Pérez et al. (2008); Singh et al. (2012a,b,c). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₃H₁₁N₃O₅S
M_r = 321.31
Triclinic, $[P \overline 1]$
a = 7.9474 (6) Å
b = 13.0122 (10) Å
c = 13.4215 (11) Å
= 87.734 (6)°
= 77.014 (7)°
= 86.945 (7)°
V = 1350.00 (18) Å³
Z = 4
Cu K radiation
= 2.43 mm^-1
T = 123 K
0.69 × 0.21 × 0.04 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), based on expressions derived by Clark & Reid (1995)] T_min = 0.441, T_max = 0.909
9239 measured reflections
5400 independent reflections
4064 reflections with I > 2(I)
R_int = 0.042

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.134
S = 1.03
5400 reflections
399 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1A-H1AAO1A	0.88	2.24	2.684 (2)	111
N2A-H2AAO2A	0.88	1.91	2.654 (2)	142
N2A-H2AAO3A	0.88	2.09	2.552 (2)	112
N1B-H1BAO1B	0.88	2.25	2.683 (2)	111
N2B-H2BAO2B	0.88	1.92	2.653 (2)	140
N2B-H2BAO3B	0.88	2.11	2.554 (2)	111
C8A-H8AAS1A	0.95	2.52	3.198 (2)	129
C8B-H8BAS1B	0.95	2.52	3.189 (2)	128

Data collection: CrysAlis PRO (Agilent, 2012); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5568 ).

Acknowledgements

SP and DPS are grateful to Banaras Hindu University, Varanasi, for financial support. RJB acknowledges the NSF-MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer. SKG wishes to acknowledge the USIEF for the award of a Fulbright-Nehru Senior Research Fellowship.

References

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organic compounds