2-Cyclo­pentyl­idenehydrazine­carboxamide

Hoong-Kun Fun; Wan-Sin Loh; Mahesh Padaki; Arun M Isloor; Nishitha A Isloor

doi:10.1107/S1600536812034599

. 2012 Aug 11;68(Pt 9):o2675–o2676. doi: 10.1107/S1600536812034599

2-Cyclopentylidenehydrazinecarboxamide

Hoong-Kun Fun ^a,^*,^‡, Wan-Sin Loh ^a,^§, Mahesh Padaki ^b, Arun M Isloor ^b, Nishitha A Isloor ^c

PMCID: PMC3435698 PMID: 22969569

Abstract

The asymmetric unit of the title compound, C₆H₁₁N₃O, consists of two independent molecules in which the cyclopentane rings adopt envelope conformations with CH₂ grouping as the flap and the semicarbazone groups are essentially planar, with maximums deviation of 0.0311 (12) and 0.0285 (12) Å. In the crystal, N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds link the molecules to form sheets lying parallel to the ab plane.

Related literature

For background to the biological activity of semicarbazones, see: Dogan et al. (1999 ▶); Pandeya & Dimmock (1993 ▶); Pandeya et al. (1998 ▶); Yogeeswari et al. (2004 ▶); Sriram et al. (2004 ▶); Fun et al. (2011 ▶). For related structures, see: Fun et al. (2009a ▶,b ▶). For further synthetic details, see: Furniss et al. (1978 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₆H₁₁N₃O
M _r = 141.18
Monoclinic,
a = 8.9507 (1) Å
b = 10.7929 (2) Å
c = 15.0204 (2) Å
β = 95.126 (1)°
V = 1445.23 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.964, T _max = 0.995
14322 measured reflections
4231 independent reflections
3120 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.114
S = 1.00
4231 reflections
205 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034599/hb6915sup1.cif

e-68-o2675-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034599/hb6915Isup2.hkl

e-68-o2675-Isup2.hkl^{(207.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812034599/hb6915Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H1N2⋯O1B	0.875 (17)	2.048 (17)	2.9088 (14)	167.7 (17)
N3A—H1N3⋯N1B ⁱ	0.858 (18)	2.614 (18)	3.3214 (16)	140.5 (16)
N3A—H2N3⋯O1A ⁱⁱ	0.926 (19)	1.949 (19)	2.8749 (16)	178.7 (15)
N2B—H2N2⋯O1A	0.919 (17)	2.065 (17)	2.9663 (14)	166.6 (16)
N3B—H3N3⋯O1B ⁱⁱⁱ	0.889 (19)	1.980 (19)	2.8682 (16)	175.9 (18)
N3B—H4N3⋯N1A ^iv	0.858 (17)	2.515 (17)	3.1771 (16)	134.7 (15)
C1A—H1AB⋯O1B ^v	0.99	2.52	3.3923 (18)	146

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). AMI is thankful to the Board of Research in Nuclear Sciences, Government of India for the Young Scientist award. AMI also thanks the Vision Group on Science & Technology, Government of Karnataka, India for the Best Research Paper award.

supplementary crystallographic information

Comment

Various semicarbazones, have been known to possess biological activities against many of the most common species of bacteria (Dogan et al., 1999). Semicarbazones are of much interest due to their wide spectrum of antibacterial activities (Pandeya & Dimmock, 1993). Recently some workers reviewed the bioactivity of semicarbazones and they have exhibited anticonvulsant (Pandeya et al., 1998; Yogeeswari et al., 2004) and antitubercular (Sriram et al., 2004) properties. Our previous report highlights the synthesis and crystal structures of the semicarbozones (Fun et al., 2011). In continuation of our studies in this area, we now report the synthesis and structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, consists of two crystallographically independent molecules. The cyclopentane (C1–C5) rings adopt an envelope conformation. The semicarbazone groups (O1/N1–N3/C6) are essentially planar with maximum deviation of 0.0311 (12) Å at atom N2A and 0.0285 (12) Å at atom N2B. Bond lengths and angles are comparable with the related structures (Fun et al. 2009a,b).

In the crystal, Fig. 2, N2A—H1N2···O1B, N3A—H1N3···N1B, N3A—H2N3···O1A, N2B—H2N2···O1A, N3B—H3N3···O1B, N3B—H4N3···N1A and C1A—H1AB···O1B hydrogen bonds (Table 1), link the molecules to form planes parallel to the ab plane.

Experimental

Semicarbazide hydrochloride (0.66 g, 0.0059 mol) and freshly recrystallized sodium acetate (0.58 g, 0.007 mol) were dissolved in water (10 ml) following a literature procedure (Furniss et al., 1978). The reaction mixture was stirred at room temperature for 10 minutes. To this, cyclopentanone (0.5 g, 0.0059 mol) was added and shaken well. A little alcohol was added to dissolve the turbidity. It was shaken for 10 more minutes and allowed to stand. The semicarbazone crystallized on standing for 6 h. The separated crystals were filtered, washed with cold water and recrystallized from ethanol as colourless plates. M.p. 495–498 K.