Dimethyl 2,2′-[(4-oxo-2-phenyl-4H-chromene-5,7-di­yl)di­oxy]diacetate: a less densely packed polymorph

Nallasivam, A.; Nethaji, M.; Vembu, N.; Jaswant, B.; Sulochana, N.

doi:10.1107/S1600536809001019

Volume 65
Part 2
Pages o314-o315
February 2009

Received 6 November 2008
Accepted 8 January 2009
Online 14 January 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.055
wR = 0.140
Data-to-parameter ratio = 16.3
Details

Dimethyl 2,2'-[(4-oxo-2-phenyl-4H-chromene-5,7-diyl)dioxy]diacetate: a less densely packed polymorph

Angannan Nallasivam,^a Munirathinam Nethaji,^b Nagarajan Vembu,^c ^* Buckle Jaswant ^d and Nagarajan Sulochana ^a

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India,^bDepartment of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India,^cDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India, and ^dDepartment of Chemistry, Government Arts College, Karur 639 005, India
Correspondence e-mail: vembu57@yahoo.com

The title molecule, C₂₁H₁₈O₈, crystallizes in two crystal polymorphs, see also Nallasivam, Nethaji, Vembu & Jaswant [Acta Cryst. (2009), E65, o312-o313]. The main difference between the two polymorphs is in the conformation of the oxomethylacetate groups with regard to the almost planar [total puckering amplitude 0.047 (2) Å] chromene ring. In the title compound, the best planes of the oxomethylacetate groups through the non-H atoms are almost perpendicular to the chromene ring [making dihedral angles of 89.61 (6) and 80.59 (5)°], while in the second polymorph the molecules are close to planar. Both crystal structures are stabilized by C-HO.

Related literature

For the second polymorph, see: Nallasivam et al. (2009). For the biological and pharmacological properties of benzopyrans and their derivatives, see: Brooks (1998); Hatakeyama et al. (1988); Hyana & Saimoto (1987); Tang et al. (2007). For the importance of 4H-chromenes, see Liu et al. (2007); Wang, Fang et al. (2003); Wand, Zheng et al. (2003).For hydrogen-bond motifs, see: Bernstein et al. (1995); Desiraju & Steiner (1999); Etter (1990).

Experimental

Crystal data

C₂₁H₁₈O₈
M_r = 398.35
Triclinic, $[P \overline 1]$
a = 9.4024 (16) Å
b = 9.8506 (17) Å
c = 11.1570 (18) Å
= 67.817 (3)°
= 80.300 (3)°
= 89.683 (3)°
V = 941.3 (3) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 293 (2) K
0.42 × 0.35 × 0.29 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) T_min = 0.955, T_max = 0.969
8351 measured reflections
4316 independent reflections
2424 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.140
S = 0.98
4316 reflections
264 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C19-H19AO17ⁱ	0.97	2.54	3.214 (3)	127
C19-H19AO18ⁱ	0.97	2.58	3.366 (2)	138
Symmetry codes: (i) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2124 ).

Acknowledgements

AN thanks Dr Naresh Kumar and Dr G. Vengatachalam, School of Chemistry, Bharathidasan University, Tiruchirappalli, and Organica Aromatics Pvt Ltd Bangalore, India, for providing laboratory facilities.

References

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organic compounds