2-Isonicotinoyl-N-phenyl­hydrazine­carbothio­amide dimethyl­formamide hemisolvate

Zhao, P.-H.; Jiang, S.-L.

doi:10.1107/S1600536811011950

Volume 67
Part 5
Page o1081
May 2011

Received 19 March 2011
Accepted 31 March 2011
Online 13 April 2011

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.005 Å
R = 0.069
wR = 0.143
Data-to-parameter ratio = 12.7
Details

2-Isonicotinoyl-N-phenylhydrazinecarbothioamide dimethylformamide hemisolvate

Pei-Hua Zhao ^a and Shao-Liang Jiang ^b ^*

^aSchool of Materials Science and Engineering, North University of China, Taiyuan 030051, People's Republic of China, and ^bCollege of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: shljiang@zjut.edu.cn

The title compound, C₁₃H₁₂N₄OS·0.5C₃H₇NO, contains four hydrazine molecules and two solvent molecules in the asymmetric unit. The dihedral angles between the pyridine and phenyl rings in the hydrazine molecules are 67.51 (16), 68.28 (16), 81.36 (15) and 83.32 (15)°. In the crystal, the molecules are linked by N-HN, N-HO and N-HS hydrogen bonds.

Related literature

For the biological activity of related compounds and further references, see: Liu et al. (2011).

Experimental

Crystal data

2C₁₃H₁₂N₄OS·C₃H₇NO
M_r = 617.74
Triclinic, $[P \overline 1]$
a = 9.901 (3) Å
b = 16.583 (5) Å
c = 18.610 (5) Å
= 99.350 (6)°
= 91.831 (6)°
= 96.454 (4)°
V = 2991.8 (15) Å³
Z = 4
Mo K radiation
= 0.23 mm^-1
T = 113 K
0.22 × 0.20 × 0.10 mm

Data collection

Rigaku Saturn CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) T_min = 0.952, T_max = 0.978
28071 measured reflections
10511 independent reflections
8262 reflections with I > 2(I)
R_int = 0.053

Refinement

R[F² > 2(F²)] = 0.069
wR(F²) = 0.143
S = 1.13
10511 reflections
827 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.80 e Å^-3
_min = -0.62 e Å^-3

Table 1
Selected geometric parameters (Å, °)

S1-C7	1.699 (3)
N1-C7	1.325 (4)
N1-C6	1.437 (4)
N2-C7	1.349 (4)
N2-N3	1.391 (4)

C7-N1-C6	122.5 (3)
C7-N2-N3	120.9 (3)
C12-N4-C11	116.4 (3)
N1-C7-N2	117.8 (3)
N1-C7-S1	123.4 (2)
N2-C7-S1	118.7 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AO6ⁱ	0.90 (1)	2.63 (3)	3.325 (5)	135 (3)
N2-H2AS1ⁱ	0.90 (1)	2.34 (1)	3.229 (3)	171 (3)
N3-H3AO2ⁱⁱ	0.90 (1)	2.08 (3)	2.812 (4)	138 (3)
N14-H14AS2ⁱⁱ	0.90 (1)	2.46 (1)	3.341 (3)	166 (3)
N5-H5AN8ⁱⁱⁱ	0.90 (1)	2.21 (1)	3.087 (4)	165 (3)
N6-H6AS4^iv	0.90 (1)	2.46 (1)	3.341 (3)	167 (3)
N11-H11AO4^iv	0.90 (1)	2.01 (2)	2.818 (3)	149 (3)
N10-H10AS3^v	0.90 (1)	2.32 (1)	3.211 (3)	170 (3)
N13-H13AN16^vi	0.90 (1)	2.17 (1)	3.041 (4)	163 (3)
N1-H1AN12	0.90 (1)	2.04 (1)	2.909 (4)	164 (3)
N7-H7AO1	0.90 (1)	1.95 (2)	2.784 (4)	155 (3)
N9-H9AN4	0.90 (1)	2.04 (1)	2.914 (4)	163 (3)
N15-H15AO3	0.90 (1)	2.00 (2)	2.813 (4)	150 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+2, -y+1, -z+1; (iv) x+1, y, z; (v) -x+1, -y+2, -z; (vi) -x, -y+2, -z.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5821 ).

References

Liu, X. H., Tan, C. X. & Weng, J. Q. (2011). Phosphorus Sulfur Silicon Relat. Elem. 186, 558-564.
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc. The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds