3-Methyl­benzo[1,2-c:5,4-c′]dichromen-6(8H)-one

M Kayalvizhi; G Vasuki; Adil I Khatri; Shriniwas D Samant

doi:10.1107/S1600536814015001

. 2014 Jul 2;70(Pt 8):o838. doi: 10.1107/S1600536814015001

3-Methylbenzo[1,2-c:5,4-c′]dichromen-6(8H)-one

M Kayalvizhi ^a, G Vasuki ^a,^*, Adil I Khatri ^b, Shriniwas D Samant ^b

PMCID: PMC4158523 PMID: 25249891

Abstract

The title compound, C₂₁H₁₄O₃, crystallizes with eight independent molecules (A–H) in the asymmetric unit which are arranged in four groups of two molecules each (AB, CD, EF and GH). In each molecule, the pyran-2-one ring is planar (r.m.s. deviations vary from 0.001 to 0.017 Å), while the pyran ring has a screw-boat conformation. In the crystal, molecules stack in two columns, along the [10-1] direction, composed of molecules C, B, E and G, and D, A, F and H. Molecules A and F are linked via C—H⋯O hydrogen bonds. In addition, there are a number of C—H⋯π contacts present involving all of the molecules. These interactions result in the formation of a three-dimensional network.

Keywords: crystal structure

Related literature

For the photosensitizing properties of coumarins, see: Kaidbey & Kligman (1981 ▶). For their medicinal applications, see: Kayalvizhi et al. (2013 ▶). For the synthesis of the title compound, see: Khatri & Samant (2014 ▶).

Experimental

Crystal data

C₂₁H₁₄O₃
M _r = 314.32
Monoclinic,
a = 20.7595 (16) Å
b = 20.7800 (16) Å
c = 28.427 (2) Å
β = 100.489 (2)°
V = 12058.1 (16) Å³
Z = 32
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.40 × 0.35 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.972, T _max = 1.000
55067 measured reflections
22280 independent reflections
11040 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.083
wR(F ²) = 0.289
S = 1.07
22280 reflections
1737 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814015001/su2746sup1.cif

e-70-0o838-sup1.cif^{(2MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015001/su2746Isup2.hkl

e-70-0o838-Isup2.hkl^{(1.2MB, hkl)}

Click here for additional data file.^{(6.1KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814015001/su2746Isup3.cml

CCDC reference: 1010326

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg24, Cg9, Cg39, Cg34, Cg4 and Cg14 are the centroids of rings C6E–C11E, C6B–C11B, C6H–C11H, C6G–C11G, C6A–C11A and C6C–C11C, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7A—H7A⋯O3F ⁱ	0.93	2.64	3.520 (13)	157
C7F—H7F⋯O3A ⁱⁱ	0.93	2.64	3.526 (12)	159
C21B—H21E⋯Cg24	0.96	2.68	3.575 (13)	155
C21C—H21H⋯Cg9ⁱⁱ	0.96	2.80	3.554 (12)	136
C21D—H21K⋯Cg39ⁱⁱⁱ	0.96	2.66	3.553 (12)	154
C21E—H21M⋯Cg34	0.96	2.92	3.622 (13)	131
C21F—H21Q⋯Cg4ⁱ	0.96	2.68	3.575 (13)	156
C21G—H21S⋯Cg14ⁱⁱⁱ	0.96	2.66	3.556 (12)	155

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

Acknowledgments

The authors thank the Sophisticated Analytical Instrument Facility, IIT-Madras, Chennai, for the data collection.

supplementary crystallographic information

S1. Comment

Coumarin is the simplest member of the group of oxygen heterocyclic compounds called benzo-2-pyrones. Coumarins are an important class of compound due to their presence in natural products as well as their medicinal applications, e.g. as anti-inflammatory, anti-viral, antioxidant, antibacterial, antifungal, anti-HIV and as anti-carcinogenic agents. Coumarin and its derivatives also have applications as fluorescent dyes for synthetic fibres and daylight fluorescent pigments (Kayalvizhi et al.., 2013). Coumarin and several of its derivatives were investigated for their photosensitizing properties. With a few exceptions, the coumarins are potentially strong photocontact sensitizers but do not evoke phototoxic reactions (Kaidbey & Kligman, 1981).

The title compound, crystallizes with eight independent molecules in the asymmetric unit, which have been labelled in an identical manner (Fig. 1, 2, 3 and 4) and are distinguished by suffixes A, B, C, D, E, F, G and H, respectively. The asymmetric unit is composed of four groups of two molecules each (AB, CD, EF & GH). In each groups the molecules differ in their orientation. In each molecule, the pyran-2-one ring is planar, while the pyran ring has a screw-boat conformation.

In the crystal, molecules A and F are linked via C—H···O hydrogen bonds; between atoms C7A and O3Fⁱ and C7F and O3Aⁱⁱ (Table 1 and Fig. 5). In addition, a number of C—H···π interactions are observed (Table 1 and Fig. 6).

S2. Experimental

The compound was synthesized according to the published procedure (Khatri & Samant, 2014).