(N′,N′′Z,N′,N′′E)-N′,N′′-[1-(4-Chloro­phen­yl)ethane-1,2-diyl­idene]bis­(3-methyl-1-benzofuran-2-carbohydrazide)

Hoong-Kun Fun; Tze Shyang Chia; Ahmed M Alafeefy; Hatem A Abdel-Aziz

doi:10.1107/S1600536812030504

. 2012 Jul 10;68(Pt 8):o2405–o2406. doi: 10.1107/S1600536812030504

(N′,N′′Z,N′,N′′E)-N′,N′′-[1-(4-Chlorophenyl)ethane-1,2-diylidene]bis(3-methyl-1-benzofuran-2-carbohydrazide)

Hoong-Kun Fun ^a,^*,^‡, Tze Shyang Chia ^a, Ahmed M Alafeefy ^b, Hatem A Abdel-Aziz ^c

PMCID: PMC3414328 PMID: 22904861

Abstract

In the title compound, C₂₈H₂₁ClN₄O₄, the benzofuran ring systems make dihedral angles of 7.43 (8) and 30.92 (9)° with the chloro-substituted benzene ring. The dihedral angle between the two benzofuran ring systems is 27.41 (7)°. The two benzofuran rings are connected to the chloro-substituted benzene ring through C—N—N=C and C—N—N=C—C bridges which are nearly planar [maximum deviations = 0.003 (1) and 0.037 (1) Å]. An intramolecular N—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by N—H⋯(O,N) and C—H⋯O hydrogen bonds into a tape along the c axis and these tapes are further connected by another weak C—H⋯O hydrogen bond into a sheet parallel to the bc plane. π–π interactions [centroid-to-centroid distances = 3.4845 (12)–3.6250 (13) Å] are also observed.

Related literature

For the biological activity of benzofurans, see: Abdel-Aziz et al. (2009 ▶); Abdel-Aziz & Mekawey (2009 ▶); Abdel-Wahab et al. (2009 ▶); Bhovi et al. (2010 ▶). For the synthesis, see: Abdel-Aziz et al. (2009 ▶). 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

C₂₈H₂₁ClN₄O₄
M _r = 512.94
Monoclinic,
a = 7.5539 (9) Å
b = 23.332 (3) Å
c = 13.6027 (16) Å
β = 94.275 (2)°
V = 2390.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.30 × 0.11 × 0.09 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.942, T _max = 0.983
19379 measured reflections
6850 independent reflections
4662 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.144
S = 1.03
6850 reflections
344 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.49 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/S1600536812030504/is5163sup1.cif

e-68-o2405-sup1.cif^{(33KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030504/is5163Isup2.hkl

e-68-o2405-Isup2.hkl^{(335.2KB, 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—H1N1⋯N3	0.89 (2)	1.96 (2)	2.644 (2)	132.3 (18)
N4—H1N4⋯O2ⁱ	0.95 (3)	2.31 (3)	3.187 (2)	154 (2)
N4—H1N4⋯N2ⁱ	0.95 (3)	2.48 (3)	3.205 (2)	134 (2)
C17—H17A⋯O2ⁱ	0.93	2.32	3.165 (2)	150
C28—H28C⋯O4ⁱⁱ	0.96	2.53	3.464 (2)	164

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

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). TSC thanks the Malaysian government and USM for the award of a Research Fellowship. The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University, for funding and facilities.

supplementary crystallographic information

Comment

Benzofurans are found to be useful as anticonvulsant, anti-inflammatory, antitumor, antifungal, anthelmintic and antihyperglycemic agents (Abdel-Aziz et al., 2009; Abdel-Aziz & Mekawey, 2009; Abdel-Wahab et al., 2009; Bhovi et al., 2010). In view of the biological activities and in continuation to our interest with benzofurans, we report herein the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The O1/C1–C8 and O3/C19–C26 benzofuran ring systems (r.m.s. deviations = 0.0096 and 0.0052 Å, respectively) make dihedral angles of 7.43 (8) and 30.92 (9)°, respectively with the chloro-substituted C11–C16 benzene ring. The dihedral angle between the two benzofuran ring systems is 27.41 (7)°. The two benzofuran rings are connected to the chloro-substituted benzene ring through C9—N1—N2—C10 and C18—N4—N3—C17—C10 bridges which are nearly planar [maximum deviations = 0.003 (1) Å at atom N2 and 0.037 (1) Å at atom C17] and the ketone O2 and O4 atoms are almost coplanar with their attached bridges [N2—N1—C9—O2 = 0.1 (3)° and N3—N4—C18—O4 = 11.4 (3)°]. An intramolecular N1—H1N1···N3 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995) in the molecule.

In the crystal (Fig. 2), the molecules are linked by N4—H1N4···(O2,N2) and C17—H17A···O2 hydrogen bonds (Table 1) into a tape along the c axis and the tapes are further connected by weak C28—H28C···O4 hydrogen bonds into a sheet parallel to the bc plane. π–π interactions are also observed with Cg1···Cg3 = 3.4845 (12) Å [-x, 2 - y, 1 - z], Cg2···Cg4 = 3.6250 (13) Å [-1 + x, 3/2 - y, -1/2 + z] and Cg3···Cg3 = 3.6124 (13) Å [-1 - x, 2 - y, 1 - z], where Cg1, Cg2, Cg3 and Cg4 are the centroids of O1/C1/C6–C8, O3/C19–C21/C26, C1–C6 and C11–C16 rings, respectively.

Experimental

The title compound was prepared by the reaction of 3-methylbenzofuran-2-carbohydrazide with 2-chloro-1-(4-chlorophenyl)ethanone in absolute ethanol according to the reported method (Abdel-Aziz et al., 2009). Colourless blocks suitable for an X-ray structural analysis were obtained by slow evaporation from EtOH/DMF.