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

Saeed, S.; Rashid, N.; Butcher, R.J.; Öztürk Yildirim, S.; Hussain, R.

doi:10.1107/S1600536812041864

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 (C-C) = 0.002 Å
R = 0.041
wR = 0.113
Data-to-parameter ratio = 13.4
Details

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

Sohail Saeed,^a ^* Naghmana Rashid,^a Ray J. Butcher,^b Sema Öztürk Yildirim ^c and Rizwan Hussain ^d

^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-HO hydrogen bond. Weak C-HO link the molecules into a sheet parallel to the bc plane. C-HS interactions also occur.

Related literature

For related structures, see: Saeed et al. (2010a,b, 2011, 2012).

Experimental

Crystal data

C₁₀H₁₀N₄O₅S·C₉H₉N₃O₅
M_r = 537.47
Triclinic, $[P \overline 1]$
a = 9.8457 (5) Å
b = 10.0057 (5) Å
c = 12.5185 (6) Å
= 72.413 (5)°
= 78.428 (4)°
= 89.129 (4)°
V = 1150.35 (10) Å³
Z = 2
Cu K radiation
= 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) T_min = 0.488, T_max = 0.628
7591 measured reflections
4597 independent reflections
4099 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(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
_max = 0.44 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3A-H1NAO5B	0.84 (2)	2.07 (2)	2.888 (2)	163 (2)
C2B-H2BAO1Aⁱ	0.95	2.51	3.390 (2)	155
C4B-H4BAO3Aⁱⁱ	0.95	2.35	3.163 (2)	143
C6B-H6BAS1A	0.95	2.76	3.6856 (16)	166
C9A-H9ABO5Bⁱⁱⁱ	0.98	2.48	3.368 (2)	150
C9B-H9BBO4B^iv	0.98	2.46	3.439 (2)	175
C10A-H10BO2A^v	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2011); 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: 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.
Saeed, S., Rashid, N., Hussain, R., Jones, P. G. & Bhatti, M. H. (2010a). Cent. Eur. J. Chem. 8, 550-558.
Saeed, S., Rashid, N., Jones, P. G., Ali, M. & Hussain, R. (2010b). Eur. J. Med. Chem. 45, 1323-1331.
Saeed, S., Rashid, N., Jones, P. G. & Tahir, A. (2011). J. Heterocycl. Chem. 48, 74-84.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds