Crystal structure of 2-oxo-N′-phenyl-2H-chromene-3-carbohydrazide

Joel T Mague; Shaaban K Mohamed; Mehmet Akkurt; Sabry H H Younes; Mustafa R Albayati

doi:10.1107/S2056989015022495

. 2015 Nov 28;71(Pt 12):o1005–o1006. doi: 10.1107/S2056989015022495

Crystal structure of 2-oxo-N′-phenyl-2H-chromene-3-carbohydrazide

Joel T Mague ^a, Shaaban K Mohamed ^b,^c, Mehmet Akkurt ^d, Sabry H H Younes ^e, Mustafa R Albayati ^f,^*

PMCID: PMC4719947 PMID: 26870466

Abstract

In the title compound, C₁₆H₁₂N₂O₃, the 2H-chromene moiety is essentially planar, with an r.m.s. deviation of the nine constituent atoms from the mean plane of 0.0093 Å, and makes a dihedral angle of 76.84 (3)° with the pendant phenyl ring. An intramolecular N—H⋯O hydrogen bond helps to determine the conformation of the side chain. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds link the molecules, forming [100] chains.

Keywords: crystal structure, coumarins, bio-activity, coumarin scaffold compounds

Related literature

For synthesis and bio-activity of coumarin scaffold compounds, see: Shivashankar et al. (2008a ▸,b ▸, 2009 ▸); Bansal et al. (2013 ▸); Jacquot et al. (2007 ▸); Bhavsar et al. (2011 ▸).

Experimental

Crystal data

C₁₆H₁₂N₂O₃
M _r = 280.28
Triclinic,
a = 6.6508 (2) Å
b = 8.3906 (3) Å
c = 11.6388 (4) Å
α = 96.504 (2)°
β = 95.614 (2)°
γ = 94.757 (2)°
V = 639.31 (4) Å³
Z = 2
Cu Kα radiation
μ = 0.85 mm⁻¹
T = 150 K
0.19 × 0.13 × 0.05 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2015 ▸) T _min = 0.88, T _max = 0.96
4865 measured reflections
2371 independent reflections
2121 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.107
S = 1.06
2371 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2015 ▸); cell refinement: SAINT (Bruker, 2015 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015022495/ff2144sup1.cif

e-71-o1005-sup1.cif^{(160.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022495/ff2144Isup2.hkl

e-71-o1005-Isup2.hkl^{(189.9KB, hkl)}

Click here for additional data file.^{(5.3KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015022495/ff2144Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015022495/ff2144fig1.tif

The title molecule with labeling scheme and 50% probability ellipsoids. The intramolecular N—H⋯O hydrogen bond is shown by a dotted line.

Click here for additional data file.^{(1.2MB, tif)}

. DOI: 10.1107/S2056989015022495/ff2144fig2.tif

Packing viewed towards (110) with intermolecular N—H⋯O and N—H⋯N hydrogen bonds shown, respectively, as blue and purple dotted lines.

CCDC reference: 1438684

Additional supporting information: 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—H1N⋯N2ⁱ	0.896 (18)	2.327 (18)	3.0498 (14)	137.7 (15)
N1—H1N⋯O2	0.896 (18)	2.112 (18)	2.7544 (13)	127.8 (15)
N2—H2N⋯O2ⁱⁱ	0.911 (17)	2.243 (17)	3.1358 (14)	166.3 (14)

Open in a new tab

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

Acknowledgments

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

supplementary crystallographic information

S1. Comment

Coumarins are known to be biologically versatile compounds possessing several biological properties. Numerous research reports have indicated the coumarin nucleus as a potential candidate for development of anti-inflammatory (Shivashankar et al., 2008a,b; Bansal et al., 2013), antibacterial (Shivashankar et al., 2008b), antifungal (Shivashankar et al., 2009), anti-cancer (Jacquot et al., 2007) and anti-HIV (Bhavsar et al., 2011) agents. In light of such facts, we report in this study the synthesis and crystal structure of the title compound.

The 2H-chromene moiety is essentially planar with an r.m.s. deviation of the nine constituent atoms from the mean plane of 0.0093 Å. The dihedral angle between this plane and that of the pendant phenyl ring is 76.84 (3)°. The conformation of the hydrazide side-chain is partially determined by an intramolecular N1—H1N···O2 hydrogen bond (Fig. 1 and Table 1). The packing is assisted by intermolecular N2—H2N···O2ⁱ (i: x − 1, y, z) and N1—H1N···N2ⁱⁱ (ii: −x + 1, −y + 1, −z) hydrogen bonds (Fig. 2 and Table 1).

S2. Experimental

The title compound was obtained as an unexpected product from the reaction of 1-phenylpyrazolidine-3,5-dione (176 mg, 1 mmol), 2-hydroxybenzaldehyde (122 mg, 1 mmol) and o-toluidine (107 mg, 1 mmol). The reaction mixture was refluxed in 20 ml e thanol and monitored by TLC till completion. On cooling, the solid product was deposited, filtered off under vacuum and recrystallized from ethanol to afford colourless crystals in a sufficient quality for X-ray diffraction. Mp 471–473 K.