Allyl 2-(2,2-dimethyl-3a,6a-di­hydro­furo[3,2-d][1,3]dioxol-5-yl)-4-oxo-4H-chromene-3-carboxyl­ate

Fatima, Z.; Srinivasan, T.; Rao, J.N.S.; Raghunathan, R.; Velmurugan, D.

doi:10.1107/S1600536813018904

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Pages o1257-o1258

doi:10.1107/S1600536813018904

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Allyl 2-(2,2-dimethyl-3a,6a-dihydrofuro[3,2-d][1,3]dioxol-5-yl)-4-oxo-4H-chromene-3-carboxylate

Zeenat Fatima,^a Thothadri Srinivasan,^a Jonnalagadda Naga Siva Rao,^b Raghavachary Raghunathan ^b and Devadasan Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 3 July 2013; accepted 8 July 2013; online 13 July 2013)

In the title compound, C₂₀H₁₈O₇, the dioxolane ring adopts an envelope conformation with the dimethyl-substituted C atom as the flap, and its mean plane makes a dihedral angle of 73.25 (2)° with the pyran ring mean plane. The furan ring makes dihedral angles of 67.43 (12) and 6.20 (11)° with the mean plane of the dioxolane and pyran rings, respectively. The O atom attached to the pyran ring deviates by 0.0219 (2) Å from its mean plane. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming chains along [010] and enclosing R₂²(9) loops. They stack along the a axis with π–π interactions involving the 4H-chromene units [centroid–centroid distances of 3.6389 (13) and 3.6555 (13) Å]. The terminal CH₂=CH- atoms of the allyl acetate group are disordered over two sets of sites with a refined occupancy ratio of 0.717 (6):0.283 (6).

Related literature

For the biological importance of 4H-chromene derivatives, see: Cai (2007 , 2008 ); Cai et al. (2006 ); Caine (1993 ); Gabor (1988 ); Brooks (1998 ); Valenti et al. (1993 ); Hyana & Saimoto (1987 ); Tang et al. (2007 ).

Experimental

Crystal data

C₂₀H₁₈O₇
M_r = 370.34
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.9461 (6) Å
b = 15.5688 (11) Å
c = 16.5572 (11) Å
V = 1790.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.969, T_max = 0.979
17828 measured reflections
4459 independent reflections
2758 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.127
S = 1.01
4459 reflections
252 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O3ⁱ	0.93	2.47	3.190 (3)	134
C12—H12⋯O2ⁱ	0.98	2.54	3.477 (3)	160
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813018904/su2620sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018904/su2620Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813018904/su2620Isup3.cml

checkCIF report

Comment top

4H-Chromenes are biologically important compounds used as synthetic ligands in the design of drugs and discovery processes. They exhibit numerous biological and pharmacological properties, such as anti-viral, anti-fungal, anti-inflammatory, anti-diabetic, cardionthonic, anti-anaphylactic and anti-cancer activity (Cai, 2008, 2007; Cai et al., 2006; Caine, 1993; Gabor, 1988; Brooks, 1998; Valenti et al., 1993; Hyana & Saimoto, 1987; Tang et al., 2007). In view of the different applications of this class of compounds, we have undertaken the synthesis and crystal structure analysis of the title compound.

In the title molecule, Fig. 1, the dioxolane ring adopts an envelope conformation with atom C14 as the flap. The furan ring (O5/C10-C13) makes dihedral angles of 67.43 (12)° and 6.20 (11)° with the mean plane of the dioxolane ring (06/07/C12-C14) and the pyran ring (O1/C1/C6-C9), respectively. The dioxolane ring mean plane makes a dihedral angle of 73.25 (11) ° with the pyran ring. The oxygen atom O2 attached with the pyran ring deviates by -0.0219 (2)Å. The methyl carbon atoms C15 and C16 attached with the mean plane of the dioxolane ring deviate by -0.7157 (3)Å and 1.6682 (3)Å, respectively.

In the crystal, molecules are linked via C-H···O hydrogen bonds into chains along [010], containing R₂²(9) loops (Table 1 and Fig. 2). They stack along the a axis with π-π interactions involving the 4H-chromene units, with centroid-to-centroid distances of 3.6389 (13) Å for Cg1-Cg2ⁱ and 3.6555 (13) Å for Cg1···Cg2ⁱⁱ, where Cg1 and Cg2 are the centroids of rings O1/C1/C6-C9 and C1-C6, respectively; symmetry codes: (i) x+1/2, -y+1/2, -z+1; (ii) x-1/2, -y+1/2, -z+1.

Related literature top

For the biological importance of 4H-chromene derivatives, see: Cai (2007, 2008); Cai et al. (2006); Caine (1993); Gabor (1988); Brooks (1998); Valenti et al. (1993); Hyana & Saimoto (1987); Tang et al. (2007).

Experimental top

Triethylamine (1.10 mL, 4 equiv) was added to a stirred solution of 4-hydroxycoumarin (0.32 g, 2 mmol) and(E)-6-(benzyloxy)-2,2-dimethyl -5-(2-nitrovinyl)tetrahydrofuro[3,2-d][1,3]dioxole (0.65 g, 4 mmol) in ally alcohol (6 mL). The reaction mixture was heated at 343 - 353 K for 24h, and the progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was evaporated in vacuum. The resulting residue was further purified by flash column chromatography (ethyl acetate/hexane) on silica gel. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level. The position of the disordered terminal atoms (C19' & C20') of the allyl acetate group are shown with dashed bonds.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. The hydrogen bonds (see Table 1 for details) are shown as dashed lines. H-atoms not involved in hydrogen bonding have been omitted for clarity.

Allyl 2-(2,2-dimethyl-3a,6a-dihydrofuro[3,2-d][1,3]dioxol-5-yl)-4-oxo-4H-chromene-3-carboxylate top

Crystal data top

C₂₀H₁₈O₇	F(000) = 776
M_r = 370.34	D_x = 1.374 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4459 reflections
a = 6.9461 (6) Å	θ = 1.8–28.4°
b = 15.5688 (11) Å	µ = 0.11 mm⁻¹
c = 16.5572 (11) Å	T = 293 K
V = 1790.5 (2) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	4459 independent reflections
Radiation source: fine-focus sealed tube	2758 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ω and ϕ scans	θ_max = 28.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
T_min = 0.969, T_max = 0.979	k = −18→20
17828 measured reflections	l = −21→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0549P)² + 0.1102P] where P = (F_o² + 2F_c²)/3
4459 reflections	(Δ/σ)_max < 0.001
252 parameters	Δρ_max = 0.16 e Å⁻³
3 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₁₈O₇	V = 1790.5 (2) Å³
M_r = 370.34	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.9461 (6) Å	µ = 0.11 mm⁻¹
b = 15.5688 (11) Å	T = 293 K
c = 16.5572 (11) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	4459 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2758 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.979	R_int = 0.072
17828 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	3 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
4459 reflections	Δρ_min = −0.18 e Å⁻³
252 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.8806 (3)	0.19806 (13)	0.54128 (13)	0.0478 (5)
C2	0.8795 (3)	0.13352 (16)	0.48303 (14)	0.0610 (6)
H2	0.8815	0.0760	0.4981	0.073*
C3	0.8754 (4)	0.15601 (18)	0.40384 (16)	0.0680 (7)
H3	0.8729	0.1135	0.3644	0.082*
C4	0.8749 (4)	0.2410 (2)	0.38153 (14)	0.0708 (7)
H4	0.8736	0.2554	0.3270	0.085*
C5	0.8762 (3)	0.30481 (17)	0.43860 (14)	0.0601 (6)
H5	0.8751	0.3621	0.4226	0.072*
C6	0.8792 (3)	0.28392 (13)	0.52099 (12)	0.0483 (5)
C7	0.8791 (3)	0.34926 (13)	0.58404 (14)	0.0490 (5)
C8	0.8760 (3)	0.31570 (12)	0.66668 (12)	0.0450 (4)
C9	0.8759 (3)	0.23043 (12)	0.68069 (12)	0.0448 (4)
C10	0.8641 (3)	0.18772 (13)	0.75846 (12)	0.0474 (5)
C11	0.8519 (3)	0.10532 (14)	0.77512 (13)	0.0563 (6)
H11	0.8573	0.0611	0.7374	0.068*
C12	0.8280 (3)	0.09404 (15)	0.86374 (14)	0.0579 (6)
H12	0.9320	0.0591	0.8866	0.069*
C13	0.8357 (3)	0.18598 (15)	0.89523 (13)	0.0559 (5)
H13	0.9438	0.1934	0.9326	0.067*
C14	0.5271 (3)	0.13462 (15)	0.91078 (15)	0.0582 (6)
C15	0.4091 (4)	0.10992 (19)	0.98298 (17)	0.0770 (8)
H15A	0.3295	0.1575	0.9987	0.116*
H15B	0.4930	0.0948	1.0268	0.116*
H15C	0.3292	0.0616	0.9696	0.116*
C16	0.4054 (4)	0.1653 (2)	0.84136 (17)	0.0866 (9)
H16A	0.3285	0.2132	0.8585	0.130*
H16B	0.3228	0.1196	0.8237	0.130*
H16C	0.4873	0.1828	0.7976	0.130*
C17	0.8718 (3)	0.38088 (13)	0.73205 (13)	0.0521 (5)
C18	0.6630 (5)	0.4621 (2)	0.81426 (19)	0.0953 (10)
H18A	0.6832	0.5197	0.7938	0.114*	0.717 (6)
H18B	0.7520	0.4521	0.8584	0.114*	0.717 (6)
H18C	0.7873	0.4735	0.8388	0.114*	0.283 (6)
H18D	0.6207	0.5150	0.7891	0.114*	0.283 (6)
O1	0.8825 (2)	0.17128 (9)	0.62034 (8)	0.0526 (4)
O2	0.8790 (2)	0.42692 (10)	0.57063 (10)	0.0661 (4)
O3	1.0102 (3)	0.41371 (12)	0.76106 (12)	0.0808 (6)
O4	0.6918 (2)	0.39953 (12)	0.75106 (11)	0.0700 (5)
O5	0.8584 (2)	0.24039 (9)	0.82508 (9)	0.0600 (4)
O6	0.6630 (2)	0.19952 (9)	0.93415 (9)	0.0576 (4)
O7	0.6435 (2)	0.06344 (9)	0.88869 (10)	0.0658 (5)
C19	0.4667 (7)	0.4514 (4)	0.8412 (4)	0.113 (2)	0.717 (6)
H19	0.3771	0.4407	0.8007	0.135*	0.717 (6)
C20	0.4030 (9)	0.4545 (4)	0.9085 (4)	0.127 (2)	0.717 (6)
H20A	0.4847	0.4649	0.9519	0.152*	0.717 (6)
H20B	0.2720	0.4464	0.9172	0.152*	0.717 (6)
C19'	0.5331 (18)	0.4427 (12)	0.8768 (7)	0.113 (2)	0.283 (6)
H19'	0.5573	0.4675	0.9269	0.135*	0.283 (6)
C20'	0.395 (2)	0.3975 (11)	0.8720 (11)	0.127 (2)	0.283 (6)
H20C	0.3645	0.3711	0.8232	0.152*	0.283 (6)
H20D	0.3173	0.3886	0.9170	0.152*	0.283 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0385 (10)	0.0503 (12)	0.0547 (11)	−0.0032 (10)	0.0064 (10)	0.0001 (10)
C2	0.0558 (13)	0.0592 (14)	0.0681 (14)	−0.0029 (12)	0.0104 (12)	−0.0096 (11)
C3	0.0587 (14)	0.0806 (18)	0.0649 (15)	−0.0089 (14)	0.0150 (13)	−0.0147 (13)
C4	0.0567 (14)	0.101 (2)	0.0543 (13)	−0.0098 (16)	0.0078 (12)	0.0022 (14)
C5	0.0498 (12)	0.0694 (16)	0.0613 (14)	−0.0040 (12)	0.0034 (11)	0.0117 (12)
C6	0.0363 (10)	0.0534 (12)	0.0552 (12)	−0.0036 (9)	0.0037 (10)	0.0065 (9)
C7	0.0378 (10)	0.0440 (12)	0.0652 (13)	−0.0029 (9)	0.0030 (10)	0.0102 (10)
C8	0.0368 (10)	0.0390 (11)	0.0591 (11)	−0.0031 (9)	0.0010 (9)	0.0031 (9)
C9	0.0391 (10)	0.0402 (11)	0.0551 (11)	−0.0023 (9)	0.0046 (10)	0.0014 (9)
C10	0.0457 (11)	0.0405 (11)	0.0559 (11)	0.0014 (9)	0.0013 (10)	0.0009 (9)
C11	0.0634 (14)	0.0384 (11)	0.0670 (13)	0.0082 (11)	0.0120 (11)	0.0043 (10)
C12	0.0576 (13)	0.0470 (13)	0.0691 (14)	0.0098 (10)	0.0112 (11)	0.0136 (11)
C13	0.0568 (13)	0.0558 (13)	0.0552 (12)	−0.0033 (11)	−0.0054 (10)	0.0083 (11)
C14	0.0545 (12)	0.0504 (13)	0.0697 (14)	0.0003 (11)	0.0034 (12)	−0.0100 (11)
C15	0.0736 (16)	0.0735 (17)	0.0841 (17)	−0.0069 (14)	0.0211 (14)	−0.0063 (15)
C16	0.0611 (16)	0.113 (2)	0.0854 (19)	0.0091 (15)	−0.0148 (14)	−0.0031 (17)
C17	0.0566 (13)	0.0391 (11)	0.0607 (13)	−0.0057 (10)	0.0023 (11)	0.0062 (9)
C18	0.119 (3)	0.081 (2)	0.0861 (19)	0.0074 (19)	0.027 (2)	−0.0218 (17)
O1	0.0619 (9)	0.0387 (7)	0.0572 (8)	0.0002 (7)	0.0054 (7)	−0.0002 (7)
O2	0.0776 (10)	0.0426 (9)	0.0781 (10)	−0.0026 (8)	0.0005 (9)	0.0134 (7)
O3	0.0786 (12)	0.0649 (11)	0.0988 (14)	−0.0292 (10)	−0.0059 (10)	−0.0146 (10)
O4	0.0706 (11)	0.0701 (11)	0.0694 (10)	0.0107 (9)	0.0055 (9)	−0.0126 (9)
O5	0.0813 (10)	0.0417 (8)	0.0568 (8)	−0.0106 (8)	−0.0030 (9)	0.0032 (7)
O6	0.0622 (9)	0.0487 (9)	0.0618 (9)	−0.0015 (7)	0.0016 (8)	−0.0060 (7)
O7	0.0734 (11)	0.0411 (8)	0.0830 (11)	−0.0022 (8)	0.0250 (9)	0.0000 (8)
C19	0.085 (4)	0.147 (5)	0.106 (5)	0.043 (4)	−0.007 (3)	−0.051 (4)
C20	0.102 (3)	0.155 (6)	0.124 (4)	−0.006 (4)	0.028 (3)	−0.045 (4)
C19'	0.085 (4)	0.147 (5)	0.106 (5)	0.043 (4)	−0.007 (3)	−0.051 (4)
C20'	0.102 (3)	0.155 (6)	0.124 (4)	−0.006 (4)	0.028 (3)	−0.045 (4)

Geometric parameters (Å, º) top

C1—O1	1.374 (2)	C14—O7	1.420 (3)
C1—C6	1.378 (3)	C14—O6	1.436 (3)
C1—C2	1.393 (3)	C14—C15	1.500 (3)
C2—C3	1.357 (4)	C14—C16	1.505 (4)
C2—H2	0.9300	C15—H15A	0.9600
C3—C4	1.373 (4)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.371 (4)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C6	1.403 (3)	C16—H16C	0.9600
C5—H5	0.9300	C17—O3	1.190 (3)
C6—C7	1.458 (3)	C17—O4	1.322 (3)
C7—O2	1.229 (2)	C18—C19'	1.407 (10)
C7—C8	1.465 (3)	C18—O4	1.443 (3)
C8—C9	1.348 (3)	C18—C19	1.444 (6)
C8—C17	1.484 (3)	C18—H18A	0.9700
C9—O1	1.360 (2)	C18—H18B	0.9700
C9—C10	1.452 (3)	C18—H18C	0.9700
C10—C11	1.315 (3)	C18—H18D	0.9700
C10—O5	1.375 (2)	C19—C20	1.200 (7)
C11—C12	1.487 (3)	C19—H19	0.9300
C11—H11	0.9300	C20—H20A	0.9300
C12—O7	1.429 (3)	C20—H20B	0.9300
C12—C13	1.524 (3)	C19'—C20'	1.194 (10)
C12—H12	0.9800	C19'—H19'	0.9300
C13—O6	1.378 (3)	C20'—H20C	0.9300
C13—O5	1.446 (3)	C20'—H20D	0.9300
C13—H13	0.9800

O1—C1—C6	121.77 (19)	C14—C15—H15A	109.5
O1—C1—C2	116.2 (2)	C14—C15—H15B	109.5
C6—C1—C2	122.1 (2)	H15A—C15—H15B	109.5
C3—C2—C1	118.9 (2)	C14—C15—H15C	109.5
C3—C2—H2	120.6	H15A—C15—H15C	109.5
C1—C2—H2	120.6	H15B—C15—H15C	109.5
C2—C3—C4	120.5 (2)	C14—C16—H16A	109.5
C2—C3—H3	119.7	C14—C16—H16B	109.5
C4—C3—H3	119.7	H16A—C16—H16B	109.5
C5—C4—C3	120.8 (2)	C14—C16—H16C	109.5
C5—C4—H4	119.6	H16A—C16—H16C	109.5
C3—C4—H4	119.6	H16B—C16—H16C	109.5
C4—C5—C6	120.2 (2)	O3—C17—O4	125.0 (2)
C4—C5—H5	119.9	O3—C17—C8	124.9 (2)
C6—C5—H5	119.9	O4—C17—C8	110.01 (18)
C1—C6—C5	117.5 (2)	C19'—C18—O4	118.5 (8)
C1—C6—C7	120.15 (18)	O4—C18—C19	106.1 (3)
C5—C6—C7	122.3 (2)	C19'—C18—H18A	123.3
O2—C7—C6	123.8 (2)	O4—C18—H18A	110.5
O2—C7—C8	121.3 (2)	C19—C18—H18A	110.5
C6—C7—C8	114.84 (17)	C19'—C18—H18B	79.6
C9—C8—C7	120.80 (19)	O4—C18—H18B	110.5
C9—C8—C17	123.24 (18)	C19—C18—H18B	110.5
C7—C8—C17	115.96 (17)	H18A—C18—H18B	108.7
C8—C9—O1	122.74 (18)	C19'—C18—H18C	107.6
C8—C9—C10	127.15 (18)	O4—C18—H18C	107.7
O1—C9—C10	110.10 (16)	C19—C18—H18C	137.1
C11—C10—O5	114.30 (18)	H18A—C18—H18C	81.3
C11—C10—C9	129.54 (19)	C19'—C18—H18D	107.7
O5—C10—C9	116.12 (16)	O4—C18—H18D	107.7
C10—C11—C12	109.2 (2)	C19—C18—H18D	86.8
C10—C11—H11	125.4	H18B—C18—H18D	130.8
C12—C11—H11	125.4	H18C—C18—H18D	107.1
O7—C12—C11	115.1 (2)	C9—O1—C1	119.63 (16)
O7—C12—C13	104.20 (17)	C17—O4—C18	116.9 (2)
C11—C12—C13	102.87 (17)	C10—O5—C13	107.35 (15)
O7—C12—H12	111.4	C13—O6—C14	109.78 (16)
C11—C12—H12	111.4	C14—O7—C12	108.99 (16)
C13—C12—H12	111.4	C20—C19—C18	129.0 (6)
O6—C13—O5	112.41 (18)	C20—C19—H19	115.5
O6—C13—C12	105.87 (18)	C18—C19—H19	115.5
O5—C13—C12	106.21 (17)	C19—C20—H20A	120.0
O6—C13—H13	110.7	C19—C20—H20B	120.0
O5—C13—H13	110.7	H20A—C20—H20B	120.0
C12—C13—H13	110.7	C20'—C19'—C18	126.4 (14)
O7—C14—O6	104.14 (16)	C20'—C19'—H19'	116.8
O7—C14—C15	108.5 (2)	C18—C19'—H19'	116.8
O6—C14—C15	108.96 (19)	C19'—C20'—H20C	120.0
O7—C14—C16	111.8 (2)	C19'—C20'—H20D	120.0
O6—C14—C16	110.6 (2)	H20C—C20'—H20D	120.0
C15—C14—C16	112.5 (2)

O1—C1—C2—C3	179.2 (2)	O7—C12—C13—O5	−119.41 (19)
C6—C1—C2—C3	−0.5 (3)	C11—C12—C13—O5	1.1 (2)
C1—C2—C3—C4	0.8 (4)	C9—C8—C17—O3	93.4 (3)
C2—C3—C4—C5	−0.8 (4)	C7—C8—C17—O3	−87.0 (3)
C3—C4—C5—C6	0.3 (4)	C9—C8—C17—O4	−89.1 (2)
O1—C1—C6—C5	−179.62 (18)	C7—C8—C17—O4	90.6 (2)
C2—C1—C6—C5	0.1 (3)	C8—C9—O1—C1	−3.0 (3)
O1—C1—C6—C7	−0.2 (3)	C10—C9—O1—C1	175.57 (17)
C2—C1—C6—C7	179.58 (19)	C6—C1—O1—C9	2.4 (3)
C4—C5—C6—C1	0.0 (3)	C2—C1—O1—C9	−177.38 (16)
C4—C5—C6—C7	−179.5 (2)	O3—C17—O4—C18	−2.7 (3)
C1—C6—C7—O2	179.6 (2)	C8—C17—O4—C18	179.8 (2)
C5—C6—C7—O2	−1.0 (3)	C19'—C18—O4—C17	−131.5 (8)
C1—C6—C7—C8	−1.4 (3)	C19—C18—O4—C17	−162.3 (3)
C5—C6—C7—C8	178.04 (18)	C11—C10—O5—C13	−1.2 (3)
O2—C7—C8—C9	179.9 (2)	C9—C10—O5—C13	176.71 (18)
C6—C7—C8—C9	0.8 (3)	O6—C13—O5—C10	−115.4 (2)
O2—C7—C8—C17	0.3 (3)	C12—C13—O5—C10	0.0 (2)
C6—C7—C8—C17	−178.81 (17)	O5—C13—O6—C14	99.2 (2)
C7—C8—C9—O1	1.4 (3)	C12—C13—O6—C14	−16.4 (2)
C17—C8—C9—O1	−179.03 (18)	O7—C14—O6—C13	26.2 (2)
C7—C8—C9—C10	−176.96 (18)	C15—C14—O6—C13	141.8 (2)
C17—C8—C9—C10	2.7 (3)	C16—C14—O6—C13	−94.0 (2)
C8—C9—C10—C11	175.5 (2)	O6—C14—O7—C12	−25.7 (2)
O1—C9—C10—C11	−3.0 (3)	C15—C14—O7—C12	−141.66 (19)
C8—C9—C10—O5	−2.1 (3)	C16—C14—O7—C12	93.7 (2)
O1—C9—C10—O5	179.38 (16)	C11—C12—O7—C14	−95.8 (2)
O5—C10—C11—C12	2.0 (3)	C13—C12—O7—C14	16.0 (2)
C9—C10—C11—C12	−175.6 (2)	C19'—C18—C19—C20	21.5 (15)
C10—C11—C12—O7	110.8 (2)	O4—C18—C19—C20	140.6 (7)
C10—C11—C12—C13	−1.8 (3)	O4—C18—C19'—C20'	−29 (2)
O7—C12—C13—O6	0.3 (2)	C19—C18—C19'—C20'	44.0 (15)
C11—C12—C13—O6	120.75 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O3ⁱ	0.93	2.47	3.190 (3)	134
C12—H12···O2ⁱ	0.98	2.54	3.477 (3)	160

Symmetry code: (i) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈O₇
M_r	370.34
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.9461 (6), 15.5688 (11), 16.5572 (11)
V (Å³)	1790.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.969, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	17828, 4459, 2758
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.127, 1.01
No. of reflections	4459
No. of parameters	252
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O3ⁱ	0.93	2.47	3.190 (3)	134
C12—H12···O2ⁱ	0.98	2.54	3.477 (3)	160

Symmetry code: (i) −x+2, y−1/2, −z+3/2.

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. ZF, TS and DV acknowledge the UGC (SAP–CAS) for the departmental facilities. ZF also thanks the UGC for a meritorious fellowship and TS thanks the DST Inspire for a fellowship.

References

Brooks, G. T. (1998). Pestic. Sci. 22, 41–50. CrossRef Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79–101. Google Scholar
Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607. Web of Science PubMed Google Scholar
Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627–2644. Web of Science PubMed CAS Google Scholar
Caine, B. (1993). Science, 260, 1814–1816. CrossRef CAS PubMed Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91–126. Budapest: Akademiai Kiado. Google Scholar
Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437–o1438. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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Volume 69| Part 8| August 2013| Pages o1257-o1258

doi:10.1107/S1600536813018904

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Allyl 2-(2,2-di­methyl-3a,6a-di­hydro­furo[3,2-d][1,3]dioxol-5-yl)-4-oxo-4H-chromene-3-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Allyl 2-(2,2-dimethyl-3a,6a-dihydrofuro[3,2-d][1,3]dioxol-5-yl)-4-oxo-4H-chromene-3-carboxylate