3-Methyl-1-benzofuran-2-carbohydrazide

Hatem A Abdel-Aziz; Hazem A Ghabbour; Suchada Chantrapromma; Hoong-Kun Fun

doi:10.1107/S1600536812013190

. 2012 Mar 31;68(Pt 4):o1255–o1256. doi: 10.1107/S1600536812013190

3-Methyl-1-benzofuran-2-carbohydrazide

Hatem A Abdel-Aziz ^a, Hazem A Ghabbour ^a, Suchada Chantrapromma ^b,^‡, Hoong-Kun Fun ^c,^*,^§

PMCID: PMC3344183 PMID: 22606186

Abstract

In the asymmetric unit of the title benzofuran derivative, C₁₀H₁₀N₂O₂, there are three crystallograpically independent molecules, which are slightly twisted; the dihedral angle between the benzofuran ring system and the plane of the carbohydrazide unit is 8.64 (11)° in one molecule, whereas the dihedral angles are 9.58 (11) and 6.89 (10)° in the other two molecules. In the crystal, the three independent molecules are linked to each other through N—H⋯N hydrogen bonds, forming a trimer. The trimers are further linked by weak N—H⋯O and C—H⋯O hydrogen bonds into a three-dimensional network. π–π interactions with centroid–centroid distances in the range 3.4928 (11)–3.8561 (10) Å are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to and the bioactivity of benzofuran derivatives, see: Abdel-Aziz & Mekawey (2009 ▶); Abdel-Aziz, Mekawey & Dawood (2009 ▶); Abdel-Wahab et al. (2009 ▶); Dawood et al. (2005 ▶); Hu et al. (2011 ▶); Ryu et al. (2010 ▶); Ungwitayatorn et al. (2001 ▶). For related structures, see: Ma et al. (2010 ▶); Wang et al. (2011 ▶).

Experimental

Crystal data

C₁₀H₁₀N₂O₂
M _r = 190.20
Monoclinic,
a = 10.9391 (4) Å
b = 18.1257 (6) Å
c = 14.1818 (5) Å
β = 94.157 (2)°
V = 2804.55 (17) Å³
Z = 12
Cu Kα radiation
μ = 0.80 mm⁻¹
T = 296 K
0.59 × 0.58 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.651, T _max = 0.946
19906 measured reflections
5271 independent reflections
3618 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.133
S = 1.00
5271 reflections
419 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 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/S1600536812013190/is5101sup1.cif

e-68-o1255-sup1.cif^{(37.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013190/is5101Isup2.hkl

e-68-o1255-Isup2.hkl^{(258.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812013190/is5101Isup3.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
N1A—H1N1⋯N2C	0.91 (2)	2.13 (2)	3.034 (2)	171.4 (17)
N1B—H2N1⋯N2A	0.93 (2)	2.15 (2)	3.081 (2)	173.1 (17)
N1C—H3N1⋯N2B	0.89 (2)	2.12 (2)	3.016 (2)	179 (3)
N2A—H2N2⋯O1Bⁱ	0.86 (2)	2.58 (2)	3.275 (2)	140 (2)
N2B—H4N2⋯O1Aⁱⁱ	0.93 (2)	2.33 (2)	3.176 (2)	150.4 (18)
N2C—H6N2⋯O1Cⁱⁱⁱ	0.92 (2)	2.22 (2)	3.137 (2)	175.5 (17)
C6A—H6AA⋯O1A^iv	0.93	2.55	3.444 (3)	162
C5C—H5CA⋯O1B^v	0.93	2.59	3.333 (3)	137

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

Acknowledgments

The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University. HKF and SC thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. HKF also thanks King Saud University, Riyadh, Saudi Arabia, for the award of a visiting Professorship (December 23rd 2011 to January 14th 2012).

supplementary crystallographic information

Comment

Benzofuran derivatives have been reported to possess various biological activities such as antimicrobial (Abdel-Aziz & Mekawey, 2009; Abdel-Aziz, Mekawey & Dawood, 2009; Abdel-Wahab et al., 2009), antifungal (Ryu et al., 2010) and anti-inflammatory (Hu et al., 2011) properties as well as being a non-nucleoside HIV-1 reverse transcriptase inhibitor (Ungwitayatorn et al., 2001). We have during the course of our medicinal chemistry research reported the synthesis and bioactivity of benzofuran derivatives (Abdel-Aziz & Mekawey, 2009; Abdel-Aziz, Mekawey & Dawood, 2009; Abdel-Wahab et al., 2009; ). The title compound (I) was synthesized and its crystal structure was reported.

There are three crystallographic independent molecules A, B and C in the asymmetric unit of (I) with differences in bond angles (Fig. 1). The molecule of the title benzofuran derivative, C₁₀H₁₀N₂O₂, is slightly twisted. The carbohydrazide fragment in molecules A and B are slightly twisted whereas it is planar in molecule C as indicated by the torsion angles of N2–N1–C9–O1 being -173.31 (17), -6.8 (3) and -179.64 (17)°, in molecules A, B and C, respectively. The dihedral angle between the mean plane through carbohydrazide fragment and the benzofuran ring is 8.64 (11)° in molecule A whereas they are 9.58 (11)) and 6.89 (10)° in molecules B and C, respectively. The bond distances agree with the literature values (Allen et al., 1987) and are comparable with the related structures (Ma et al., 2010; Wang et al., 2011).

In the crystal packing (Fig. 2), the molecules are linked by N—H···N and N—H···O hydrogen bonds together with weak C—H···O interactions (Table 1). π–π interactions with the distances of Cg1···Cg4ⁱ = 3.8561 (10) Å, Cg2···Cg7ⁱⁱⁱ = 3.4928 (11) Å, Cg₂···Cg8ⁱⁱⁱ = 3.8179 (11) Å, Cg4···Cg7^vi = 3.7318 (10) Å and Cg4···Cg8^vi = 3.5891 (11) Å [symmetry code (vi) = 2-x, -1/2+y, 3/2-z] are also observed; Cg1, Cg2, Cg4, Cg7 and Cg8 are the centroids of C1A–C3A/C8A/O2A, C3A–C8A, C1B–C3B/C8B/O2B, C1C–C3C/C8C/O2C and C3C–C8C rings, respectively.

Experimental

The title compound was prepared from the reaction of ethyl 3-methyl-2-benzofurancarboxylate with hydrazine according to the reported method (Dawood et al., 2005). Single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by the slow evaporation of the solvent at room temperature after several days.