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Volume 68 
Part 11 
Page o3108  
November 2012  

Received 2 October 2012
Accepted 6 October 2012
Online 13 October 2012

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.113
Data-to-parameter ratio = 13.4
Details
Open access

A co-crystal of 3-(3,5-dinitrobenzoyl)-1,1-dimethylthiourea and N,N-dimethyl-3,5-dinitrobenzamide

aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan,bChemistry Department, Howard University, Washington, DC 20059, USA,cChemistry Department, Howard University, Washington, DC 20059, USA, and, Department of Physics, Faculty of Sciences, Erciyes University, 38039, Kayseri, Turkey, and dNational Engineering & Scientific Commission, PO Box 2801, Islamabad, Pakistan
Correspondence e-mail: sohail262001@yahoo.com

In the title compound, C10H10N4O5S·C9H9N3O5, the amide groups of 3-(3,5-dinitro-benzoyl)-1,1-dimethyl-thiourea and N,N-dimethyl-3,5-dinitro-benzamide molecules are oriented at dihedral angles of 39.13 (8) and 55.97 (11)°, respectively, to the attached benzene rings. In the crystal, the two molecules are linked by an N-H...O hydrogen bond. Weak C-H...O link the molecules into a sheet parallel to the bc plane. C-H...S interactions also occur.

Related literature

For related structures, see: Saeed et al. (2010a[Saeed, S., Rashid, N., Hussain, R., Jones, P. G. & Bhatti, M. H. (2010a). Cent. Eur. J. Chem. 8, 550-558.],b[Saeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010b). Eur. J. Med. Chem. 45, 1323-1331.], 2011[Saeed, S., Rashid, N., Jones, P. G. & Tahir, A. (2011). J. Heterocycl. Chem. 48, 74-84.], 2012[Saeed, S., Rashid, N., Butcher, R. J., Öztürk Yildirim, S. & Hussain, R. (2012). Acta Cryst. E68, o2762.]).

[Scheme 1]

Experimental

Crystal data
  • C10H10N4O5S·C9H9N3O5

  • Mr = 537.47

  • Triclinic, [P \overline 1]

  • a = 9.8457 (5) Å

  • b = 10.0057 (5) Å

  • c = 12.5185 (6) Å

  • [alpha] = 72.413 (5)°

  • [beta] = 78.428 (4)°

  • [gamma] = 89.129 (4)°

  • V = 1150.35 (10) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 1.90 mm-1

  • T = 123 K

  • 0.44 × 0.38 × 0.27 mm

Data collection
  • Agilent Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.488, Tmax = 0.628

  • 7591 measured reflections

  • 4597 independent reflections

  • 4099 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.113

  • S = 1.07

  • 4597 reflections

  • 342 parameters

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

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3A-H1NA...O5B 0.84 (2) 2.07 (2) 2.888 (2) 163 (2)
C2B-H2BA...O1Ai 0.95 2.51 3.390 (2) 155
C4B-H4BA...O3Aii 0.95 2.35 3.163 (2) 143
C6B-H6BA...S1A 0.95 2.76 3.6856 (16) 166
C9A-H9AB...O5Biii 0.98 2.48 3.368 (2) 150
C9B-H9BB...O4Biv 0.98 2.46 3.439 (2) 175
C10A-H10B...O2Av 0.98 2.51 3.334 (2) 142
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+2, -z; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+2, -z; (v) -x+2, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2011[Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, 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: XU5627 ).


Acknowledgements

RJB acknowledges the NSF-MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.

References

Agilent (2011). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Saeed, S., Rashid, N., Butcher, R. J., Öztürk Yildirim, S. & Hussain, R. (2012). Acta Cryst. E68, o2762.  [CSD] [CrossRef] [details]
Saeed, S., Rashid, N., Hussain, R., Jones, P. G. & Bhatti, M. H. (2010a). Cent. Eur. J. Chem. 8, 550-558.  [CSD] [CrossRef] [ChemPort]
Saeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010b). Eur. J. Med. Chem. 45, 1323-1331.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Saeed, S., Rashid, N., Jones, P. G. & Tahir, A. (2011). J. Heterocycl. Chem. 48, 74-84.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3108  [ doi:10.1107/S1600536812041864 ]

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