Ethyl 1-[3-(1H-imidazol-1-yl)prop­yl]-2-(4-chloro­phen­yl)-1H-benzo[d]imidazole-5-carboxyl­ate dihydrate

Yeong Keng Yoon; Mohamed Ashraf Ali; Ang Chee Wei; Ching Kheng Quah; Hoong-Kun Fun

doi:10.1107/S1600536811033654

. 2011 Aug 27;67(Pt 9):o2405. doi: 10.1107/S1600536811033654

Ethyl 1-[3-(1H-imidazol-1-yl)propyl]-2-(4-chlorophenyl)-1H-benzo[d]imidazole-5-carboxylate dihydrate

Yeong Keng Yoon ^a, Mohamed Ashraf Ali ^a, Ang Chee Wei ^a, Ching Kheng Quah ^b,^‡, Hoong-Kun Fun ^b,^*,^§

PMCID: PMC3200625 PMID: 22058996

Abstract

In the title compound, C₂₂H₂₁ClN₄O₂·2H₂O, the almost-planar benzimidazole ring system [maximum deviation 0.014 (1) Å] is inclined at angles of 36.32 (5) and 74.75 (7)° with respect to the phenyl and imidazole rings, respectively. In the crystal structure, the water molecules are linked to the organic molecules to form a three-dimensional network via O—H⋯N and O—H⋯O hydrogen bonds. The packing is further consolidated by a pair of bifurcated C—H⋯O bonds, generating R ¹ ₂(6) loops. C—H⋯π interactions are also observed.

Related literature

For related structures and background to benzimidazoles, see: Eltayeb et al. (2009 ▶, 2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₂H₂₁ClN₄O₂·2H₂O
M _r = 444.91
Monoclinic,
a = 9.0611 (1) Å
b = 13.8393 (2) Å
c = 18.0470 (3) Å
β = 92.386 (1)°
V = 2261.12 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.40 × 0.30 × 0.27 mm

Data collection

Bruker SMART APEX II CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.922, T _max = 0.947
31604 measured reflections
8235 independent reflections
6221 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.136
S = 1.05
8235 reflections
296 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.40 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/S1600536811033654/hb6369sup1.cif

e-67-o2405-sup1.cif^{(23.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033654/hb6369Isup2.hkl

e-67-o2405-Isup2.hkl^{(402.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033654/hb6369Isup3.cml

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

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

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯N1ⁱ	0.94 (3)	1.96 (3)	2.8802 (14)	164 (2)
O1W—H2W1⋯O2Wⁱⁱ	0.91 (2)	1.83 (2)	2.7284 (18)	169 (2)
O2W—H1W2⋯N4ⁱⁱⁱ	0.849 (19)	1.978 (19)	2.8147 (19)	169 (2)
O2W—H2W2⋯O2ⁱ	0.87 (2)	1.98 (2)	2.8460 (17)	172 (2)
C17—H17B⋯O1W^iv	0.99	2.49	3.3785 (16)	149
C19—H19B⋯O1W^iv	0.99	2.51	3.3799 (19)	147
C10—H10A⋯Cg1^v	0.95	2.86	3.4875 (14)	125

Open in a new tab

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

Acknowledgments

The authors thank Universiti Sains Malaysia (USM), Penang, Malaysia, for providing research facilities. HKF and CKQ also thank USM for a Research University Grant (No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

As part of our ongoing structural studies of benzimidazole derivatives (Eltayeb et al., 2011), we now report the structure of the title compound, (I), which crystallised as a dihydrate.

In the title molecule, Fig. 1, the benzimidazole ring system (N1/N2/C1–C7, maximum deviation of 0.014 (1) Å at atom C4) is inclined at angles of 36.32 (5) and 74.75 (7)° with respect to the phenyl (C8–C13) and imidazole (N3/N4/C20–C22 ) rings. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those in related structures (Eltayeb et al., 2009, 2011).

In the crystal, water molecules are linked to main molecules to form a three-dimensional network (Fig. 2) by O1W—H1W1···N1, O1W—H2W1···O2W, O2W—H1W2···N4 and O2W—H2W2···O2 hydrogen bonds (Table 1). The crystal packing is further consolidated by bifurcated C17—H17B···O1W and C19—H19B···O1W acceptor bonds, generating R¹₂(6) ring motifs (Bernstein et al., 1995). The crystal structure is also stabilized by C10—H10A···Cg1 (Table 1) interactions, where Cg1 is the centroid of the C1–C6 phenyl ring.

Experimental

Ethyl 4-(3-(1H-imidazol-1-yl)propylamino)-3-aminobenzoate (0.84 mmol) and sodium metabisulfite adduct of chlorobenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was refluxed at 403 K for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na₂SO₄ and then evaporated in vacuo to yield the product. The product was recrystallised from ethyl acetate to yield bronze blocks of (I).