2-(4-Chloro­benzo­yl)-1-(diamino­methyl­ene)hydrazinium chloride monohydrate

Chernyshev, V.M.; Chernysheva, A.V.; Tarasova, E.V.; Ivanov, V.V.; Starikova, Z.A.

doi:10.1107/S1600536810014108

Volume 66
Part 5
Pages o1152-o1153
May 2010

Received 8 April 2010
Accepted 16 April 2010
Online 24 April 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.006 Å
R = 0.063
wR = 0.142
Data-to-parameter ratio = 16.1
Details

2-(4-Chlorobenzoyl)-1-(diaminomethylene)hydrazinium chloride monohydrate

V. M. Chernyshev,^a ^* A. V. Chernysheva,^a E. V. Tarasova,^a V. V. Ivanov ^a and Z. A. Starikova ^b

^aSouth-Russia State Technical University, 346428 Novocherkassk, Russian Federation, and ^bA. N. Nesmeyanov Institute of Organoelement Compounds, 119991 Moscow, Russian Federation
Correspondence e-mail: chern13@yandex.ru

In the cation of the title compound, C₈H₁₀ClN₄O⁺·Cl^-·H₂O, the guanidinium group is planar (maximum deviation = 0.0001 Å) and nearly perpendicular to carboxamide group, making a dihedral angle of 87.0 (3)°. The N atoms of the guanidine fragment have a planar trigonal configuration and the N atom of the carboxamide group adopts a pyramidal configuration. In the crystal structure, intermolecular N-HO, N-HCl and O-HCl hydrogen bonds link the cations, anions and water molecules into layers parallel to the bc plane.

Related literature

For a related structure, see: Kolev & Petrova (2003). For aminoguanidine structures, see: Bharatam et al. (2004); Koskinen et al. (1997); Hammerl et al. (2005); Machácková et al. (2007); Murugavel et al. (2009a,b). For the preparation of guanyl hydrazides, see: Grinstein & Chipen (1961). For the application of guanyl hydrazides in the synthesis of 3-substituted 5-amino-1,2,4-triazoles, see: Dolzhenko et al. (2009).

Experimental

Crystal data

C₈H₁₀ClN₄O⁺·Cl^-·H₂O
M_r = 267.12
Monoclinic, P 2₁ /c
a = 19.349 (4) Å
b = 4.3563 (9) Å
c = 14.516 (3) Å
= 102.360 (3)°
V = 1195.2 (4) Å³
Z = 4
Mo K radiation
= 0.54 mm^-1
T = 100 K
0.40 × 0.30 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.814, T_max = 0.924
9756 measured reflections
2330 independent reflections
2099 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.063
wR(F²) = 0.142
S = 1.17
2330 reflections
145 parameters
H-atom parameters constrained
_max = 0.79 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1Cl2ⁱ	0.90	2.36	3.194 (4)	154
N2-H2O1W	0.90	2.24	3.031 (4)	146
N2-H2Cl2ⁱⁱ	0.90	2.71	3.260 (4)	121
N3-H3BO1ⁱⁱⁱ	0.90	1.96	2.848 (3)	167
N3-H3ACl2^iv	0.90	2.43	3.280 (4)	157
N4-H4BO1W	0.90	2.04	2.834 (4)	147
N4-H4ACl2^iv	0.90	2.44	3.286 (4)	156
O1W-H1WCl2^v	0.85	2.58	3.292 (4)	142
O1W-H2WCl2	0.85	2.30	3.134 (4)	164
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z; (iv) -x+1, -y+2, -z; (v) x, y-1, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2710 ).

Acknowledgements

The authors thank the Federal Agency for Education of Russia for financial support of this work through the Federal Target Program "Research and Educational Personnel of Innovative Russia at 2009-2013 Years", State contract P1472, project NK-186P/3.

References

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Dolzhenko, A. V., Pastorin, G., Dolzhenko, A. V. & Chui, W.-K. (2009). Tetrahedron Lett. 50, 2124-2128.
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Murugavel, S., Ganesh, G., Subbiah Pandi, A., Govindarajan, S. & Selvakumar, R. (2009a). Acta Cryst. E65, o548.
Murugavel, S., Kannan, P. S., Subbiah Pandi, A., Govindarajan, S. & Selvakumar, R. (2009b). Acta Cryst. E65, o454.
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Westrip, S. P. (2010). publCIF. In preparation.

organic compounds