N′-[(2-n-Butyl-4-chloro-1H-imidazol-5-yl)­methyl­idene]adamantane-1-carbo­hydrazide sesquihydrate ethanol hemi­solvate

Abdul-Malek S Al-Tamimi; Ahmed Bari; Mohamed A Al-Omar; Ali A El-Emam; Seik Weng Ng

doi:10.1107/S1600536810029260

. 2010 Jul 31;66(Pt 8):o2131. doi: 10.1107/S1600536810029260

N′-[(2-n-Butyl-4-chloro-1H-imidazol-5-yl)methylidene]adamantane-1-carbohydrazide sesquihydrate ethanol hemisolvate

Abdul-Malek S Al-Tamimi ^a, Ahmed Bari ^a, Mohamed A Al-Omar ^a, Ali A El-Emam ^a, Seik Weng Ng ^b,^*

PMCID: PMC3007568 PMID: 21588420

Abstract

In the asymmetric unit of the title compound, C₁₉H₂₇ClN₄O·0.5C₂H₆O·1.5H₂O, there are two molecules of the Schiff base, which has a rigid adamantyl cage at one end of the C(= O)NH–N=CH– chain and an almost planar [torsion angles = 1.3 (1) and 7.9 (2)° imidazolyl ring at the other end, three molecules of water and one molecule of ethanol. In both independent molecules of the Schiff base, this chain displays an extended zigzag configuration. All their amino groups function as hydrogen-bond donors to water molecules; these are linked to other acceptor atoms, generating a layer structure. O—H⋯O and O—H⋯N interactions involving the water molecules also occur.

Related literature

For the cyclization of this class of Schiff bases to pharmaceutically useful chemicals, see: Kadi et al. (2007 ▶).

Experimental

Crystal data

C₁₉H₂₇ClN₄O·0.5C₂H₆O·1.5H₂O
M _r = 412.95
Triclinic,
a = 7.9867 (6) Å
b = 16.8478 (13) Å
c = 16.9656 (13) Å
α = 97.341 (1)°
β = 100.376 (1)°
γ = 97.505 (1)°
V = 2199.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.40 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.924, T _max = 0.980
21291 measured reflections
10050 independent reflections
7547 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.113
S = 1.02
10050 reflections
552 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029260/bt5304sup1.cif

e-66-o2131-sup1.cif^{(36.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029260/bt5304Isup2.hkl

e-66-o2131-Isup2.hkl^{(491.4KB, hkl)}

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
N1—H1⋯O3ⁱ	0.86 (1)	2.00 (1)	2.841 (2)	166 (2)
N3—H3⋯O1wⁱⁱ	0.86 (1)	1.95 (1)	2.806 (2)	170 (2)
N6—H6⋯O2w	0.88 (1)	1.95 (1)	2.829 (2)	174 (2)
N8—H8⋯O3wⁱⁱⁱ	0.86 (1)	1.94 (1)	2.778 (2)	164 (2)
O3—H3o⋯O1w	0.84 (1)	1.84 (1)	2.673 (2)	177 (2)
O1w—H11⋯O1ⁱⁱ	0.84 (1)	2.00 (1)	2.821 (2)	166 (2)
O1w—H12⋯N5	0.84 (1)	1.91 (1)	2.751 (2)	175 (3)
O2w—H21⋯O2	0.85 (1)	2.07 (1)	2.905 (2)	172 (2)
O2w—H22⋯O2^iv	0.84 (1)	1.93 (1)	2.764 (2)	176 (2)
O3w—H31⋯N4	0.84 (1)	1.94 (1)	2.773 (2)	169 (2)
O3w—H32⋯O2w	0.85 (1)	1.92 (1)	2.766 (2)	174 (2)

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

Acknowledgments

We thank King Saud University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Adamantane-1-carbohydrazide is a commercially available compound that condenses with primary amines to form Schiff bases; some of these Schiff bases can be cyclized to yield pharmaceutically useful compounds (Kadi et al., 2007). However, unlike other aryolhydrazides, there have been no reports of the crystal structures of these Schiff bases. The condensation product with 2-n-butyl-5-chloro-1H-imidazole-4-carboxaldehyde crystallizes from aqueous ethanol as a sesquihydrate hemiethanol solvate (Scheme 1). There are two independent Schiff base molecules in the asymmetric unit (Fig. 1). The molecule of C₂₀H₂₇ClN₄O has a rigid adamantyl cage at one end of the C(═ O)NH–N═CH– chain and a planar imidazolyl ring at the other end; the chain displays an extended zigzag configuration.

The amino groups all function as hydrogen-bond donors to water molecules; these are linked to other acceptor atoms to generate a layer structure (Fig. 2).

Experimental

Adamantane-1-carbohydrazide (1.94 g, 1 mmol) and 2-n-butyl-5-chloro-1H-imidazole-4-carboxaldehyde (1.87 g, 1 mmol) were heated in ethanol (50 ml) for 1 h. The solvent was removed and the product recrystallized from aqueous ethanol to afford colorless primatic crystals in 90% yield.