Methyl 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/S1600536813019648

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1310

doi:10.1107/S1600536813019648

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Methyl 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 11 July 2013; accepted 16 July 2013; online 24 July 2013)

In the title molecule, C₁₈H₁₆O₇, the dioxolane ring adopts an envelope conformation with the dimethyl-substituted C atom as the flap. The furan ring is almost coplanar with the pyran ring, with a dihedral angle of 1.04 (10)° between the planes, and it makes a dihedral angle of 67.97 (11)° with the mean plane of the dioxolane ring. The latter makes a dihedral angle of 67.15 (10)° with the pyran ring. The O atom attached to the pyran ring deviates by −0.009 (1) Å. The crystal packing features C—H⋯O hydrogen bonds, forming a three-dimensional structure. The methoxycarbonyl atoms are disordered over two positions, with a refined occupancy ratio of 0.508 (18):0.492 (18).

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 ). For conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₁₆O₇
M_r = 344.31
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.8875 (3) Å
b = 15.4958 (6) Å
c = 15.9035 (6) Å
V = 1697.34 (12) 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
9565 measured reflections
4131 independent reflections
2983 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.108
S = 1.03
4131 reflections
267 parameters
99 restraints
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O7ⁱ	0.93	2.59	3.296 (2)	133
C13—H13⋯O3ⁱⁱ	0.93	2.59	3.230 (10)	127
C14—H14⋯O1ⁱⁱ	0.98	2.50	3.429 (2)	159
C18—H18C⋯O1ⁱⁱⁱ	0.96	2.55	3.460 (3)	159
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 (Sheldrick, 2008) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813019648/su2622sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019648/su2622Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019648/su2622Isup3.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, antiinflammatory, anti-diabetic, cardionthonic, anti-anaphylactic and anti-cancer activity (Cai, 2008, 2007; Cai et al., 2006; 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 the crystal structure analysis of the title compound.

In the title molecule, Fig. 1, the dioxolane ring adopts an envelope conformation with atom C16 as the flap. The furan ring (O5/C12—C15) is almost coplanar with the pyran ring (O2/C1/C2/C7—C9), with a dihedral angle of 1.04 (10) ° and makes a dihedral angle of 67.97 (11) ° with the mean plane of the dioxolane ring (06/07/C14—C16). The mean plane of the dioxolane ring makes a dihedral angle of 67.15 (10) ° with the pyran ring. The oxygen atom O1 attached with the pyran ring deviates by -0.009 (1) Å. The methyl carbon atoms C17 and C18 attached with the dioxolane ring deviate by -1.666 (3) Å and 0.736 (3) Å, respectively from the mean plane.

The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds, forming a three-dimensional structure (Table 1 and Fig. 2).

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). For conformational analysis, see: Cremer & Pople (1975).

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 methanol (6 ml). The reaction mixture was heated at 343 - 353 K for 24 h, 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 purifed 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 the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. C-H···O hydrogen bonds are shown as dashed lines (see Table 1 for details).

Methyl 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

C₁₈H₁₆O₇	F(000) = 720
M_r = 344.31	D_x = 1.347 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4131 reflections
a = 6.8875 (3) Å	θ = 1.8–28.3°
b = 15.4958 (6) Å	µ = 0.11 mm⁻¹
c = 15.9035 (6) Å	T = 293 K
V = 1697.34 (12) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	4131 independent reflections
Radiation source: fine-focus sealed tube	2983 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω and ϕ scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
T_min = 0.969, T_max = 0.979	k = −20→14
9565 measured reflections	l = −14→21

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0575P)² + 0.0367P] where P = (F_o² + 2F_c²)/3
4131 reflections	(Δ/σ)_max < 0.001
267 parameters	Δρ_max = 0.18 e Å⁻³
99 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₁₆O₇	V = 1697.34 (12) Å³
M_r = 344.31	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.8875 (3) Å	µ = 0.11 mm⁻¹
b = 15.4958 (6) Å	T = 293 K
c = 15.9035 (6) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker SMART APEXII area-detector diffractometer	4131 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2983 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.979	R_int = 0.021
9565 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	99 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
4131 reflections	Δρ_min = −0.19 e Å⁻³
267 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.6753 (3)	0.14269 (11)	0.41547 (11)	0.0497 (4)
C2	0.6727 (3)	0.20723 (11)	0.48234 (11)	0.0476 (4)
C3	0.6773 (3)	0.18438 (14)	0.56749 (12)	0.0627 (5)
H3	0.6789	0.1265	0.5829	0.075*
C4	0.6797 (3)	0.24736 (17)	0.62848 (13)	0.0720 (6)
H4	0.6828	0.2316	0.6849	0.086*
C5	0.6775 (3)	0.33337 (15)	0.60685 (13)	0.0666 (5)
H5	0.6799	0.3754	0.6486	0.080*
C6	0.6719 (3)	0.35725 (13)	0.52421 (12)	0.0595 (5)
H6	0.6703	0.4153	0.5095	0.071*
C7	0.6686 (3)	0.29417 (11)	0.46269 (10)	0.0456 (4)
C8	0.6653 (2)	0.26426 (9)	0.31685 (10)	0.0425 (4)
C9	0.6757 (3)	0.17837 (10)	0.32992 (11)	0.0449 (4)
C12	0.6554 (3)	0.30873 (10)	0.23675 (10)	0.0449 (4)
C13	0.6472 (3)	0.39241 (11)	0.22124 (11)	0.0520 (4)
H13	0.6440	0.4357	0.2617	0.062*
C14	0.6441 (3)	0.40610 (11)	0.12871 (12)	0.0563 (5)
H14	0.5286	0.4381	0.1108	0.068*
C15	0.6451 (3)	0.31385 (11)	0.09405 (11)	0.0545 (4)
H15	0.5272	0.3025	0.0614	0.065*
C16	0.9405 (3)	0.37635 (12)	0.06399 (13)	0.0614 (5)
C17	1.0874 (4)	0.34751 (18)	0.12818 (18)	0.0877 (8)
H17A	1.1695	0.3952	0.1430	0.132*
H17B	1.1650	0.3018	0.1051	0.132*
H17C	1.0214	0.3271	0.1775	0.132*
C18	1.0317 (5)	0.40685 (17)	−0.01674 (15)	0.0937 (9)
H18A	0.9318	0.4186	−0.0573	0.141*
H18B	1.1166	0.3629	−0.0381	0.141*
H18C	1.1048	0.4585	−0.0063	0.141*
O1	0.6772 (2)	0.06461 (8)	0.42838 (9)	0.0699 (4)
O2	0.66072 (19)	0.32230 (7)	0.38098 (7)	0.0491 (3)
O5	0.6553 (2)	0.25723 (7)	0.16682 (7)	0.0544 (3)
O6	0.8081 (2)	0.30677 (8)	0.04404 (8)	0.0618 (4)
O7	0.8187 (2)	0.44315 (7)	0.09562 (8)	0.0653 (4)
O3	0.5952 (18)	0.0645 (6)	0.2327 (6)	0.081 (2)	0.508 (18)
O4	0.8963 (12)	0.1191 (6)	0.2314 (5)	0.0710 (16)	0.508 (18)
C10	0.7106 (15)	0.1130 (7)	0.2611 (7)	0.0565 (18)	0.508 (18)
C11	0.9518 (18)	0.0578 (9)	0.1669 (7)	0.108 (3)	0.508 (18)
H11A	0.9967	0.0056	0.1929	0.163*	0.508 (18)
H11B	1.0539	0.0820	0.1332	0.163*	0.508 (18)
H11C	0.8417	0.0453	0.1320	0.163*	0.508 (18)
O3'	0.5216 (14)	0.0826 (5)	0.2331 (6)	0.0666 (17)	0.492 (18)
O4'	0.8513 (16)	0.0905 (6)	0.2447 (5)	0.0742 (17)	0.492 (18)
C10'	0.6656 (16)	0.1144 (8)	0.2596 (7)	0.061 (2)	0.492 (18)
C11'	0.867 (2)	0.0196 (8)	0.1862 (6)	0.105 (4)	0.492 (18)
H11D	0.8325	−0.0332	0.2140	0.158*	0.492 (18)
H11E	0.9983	0.0157	0.1661	0.158*	0.492 (18)
H11F	0.7812	0.0291	0.1396	0.158*	0.492 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0482 (9)	0.0419 (9)	0.0589 (10)	−0.0049 (8)	−0.0052 (9)	0.0058 (8)
C2	0.0378 (8)	0.0541 (10)	0.0508 (9)	−0.0047 (8)	0.0026 (8)	0.0037 (8)
C3	0.0542 (11)	0.0733 (13)	0.0606 (12)	−0.0067 (11)	−0.0008 (10)	0.0108 (10)
C4	0.0567 (12)	0.1145 (19)	0.0448 (10)	−0.0050 (14)	0.0063 (10)	0.0005 (11)
C5	0.0576 (11)	0.0838 (15)	0.0584 (11)	−0.0008 (11)	0.0093 (11)	−0.0180 (10)
C6	0.0542 (10)	0.0625 (11)	0.0618 (11)	0.0016 (10)	0.0070 (10)	−0.0129 (9)
C7	0.0377 (8)	0.0492 (9)	0.0500 (9)	−0.0010 (8)	0.0055 (8)	−0.0024 (7)
C8	0.0407 (8)	0.0360 (8)	0.0507 (9)	−0.0020 (7)	0.0028 (8)	−0.0020 (7)
C9	0.0480 (8)	0.0358 (8)	0.0508 (9)	−0.0021 (8)	−0.0031 (9)	−0.0011 (7)
C12	0.0442 (9)	0.0389 (8)	0.0515 (9)	−0.0010 (7)	0.0049 (8)	−0.0015 (7)
C13	0.0616 (11)	0.0377 (8)	0.0568 (10)	0.0088 (8)	0.0132 (9)	0.0027 (7)
C14	0.0591 (11)	0.0453 (9)	0.0643 (11)	0.0097 (9)	0.0072 (9)	0.0115 (8)
C15	0.0566 (11)	0.0554 (10)	0.0515 (10)	−0.0042 (9)	−0.0036 (9)	0.0078 (8)
C16	0.0721 (13)	0.0455 (10)	0.0665 (12)	−0.0116 (9)	0.0215 (11)	−0.0097 (9)
C17	0.0602 (13)	0.0983 (18)	0.1045 (19)	−0.0049 (13)	0.0050 (14)	−0.0084 (16)
C18	0.130 (2)	0.0729 (14)	0.0783 (16)	−0.0319 (15)	0.0492 (15)	−0.0167 (13)
O1	0.0924 (10)	0.0408 (7)	0.0765 (9)	−0.0053 (7)	−0.0154 (9)	0.0126 (6)
O2	0.0601 (7)	0.0378 (5)	0.0495 (6)	0.0006 (6)	0.0059 (6)	−0.0029 (5)
O5	0.0746 (9)	0.0394 (6)	0.0491 (7)	−0.0077 (6)	−0.0002 (6)	0.0004 (5)
O6	0.0768 (9)	0.0494 (7)	0.0592 (7)	−0.0103 (7)	0.0143 (7)	−0.0078 (6)
O7	0.0865 (10)	0.0385 (6)	0.0709 (8)	−0.0073 (7)	0.0242 (8)	−0.0005 (6)
O3	0.110 (5)	0.047 (3)	0.087 (3)	−0.023 (3)	−0.030 (4)	−0.002 (2)
O4	0.081 (3)	0.064 (3)	0.068 (3)	0.025 (3)	−0.010 (2)	−0.017 (3)
C10	0.081 (4)	0.031 (3)	0.057 (3)	0.002 (3)	−0.029 (3)	−0.002 (3)
C11	0.126 (7)	0.109 (7)	0.090 (5)	0.048 (5)	−0.009 (4)	−0.041 (5)
O3'	0.087 (4)	0.047 (3)	0.066 (2)	−0.015 (3)	−0.022 (3)	−0.003 (2)
O4'	0.097 (4)	0.056 (3)	0.069 (3)	0.031 (3)	−0.013 (3)	−0.020 (2)
C10'	0.087 (4)	0.037 (3)	0.058 (3)	0.008 (3)	−0.013 (3)	0.005 (3)
C11'	0.151 (9)	0.094 (6)	0.072 (4)	0.060 (5)	−0.021 (5)	−0.039 (4)

Geometric parameters (Å, º) top

C1—O1	1.227 (2)	C15—O6	1.381 (2)
C1—C2	1.460 (2)	C15—O5	1.454 (2)
C1—C9	1.469 (2)	C15—H15	0.9800
C2—C7	1.383 (2)	C16—O7	1.424 (2)
C2—C3	1.400 (3)	C16—O6	1.447 (2)
C3—C4	1.376 (3)	C16—C17	1.505 (3)
C3—H3	0.9300	C16—C18	1.505 (3)
C4—C5	1.377 (3)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.366 (3)	C17—H17C	0.9600
C5—H5	0.9300	C18—H18A	0.9600
C6—C7	1.383 (2)	C18—H18B	0.9600
C6—H6	0.9300	C18—H18C	0.9600
C7—O2	1.372 (2)	O3—C10	1.183 (7)
C8—C9	1.349 (2)	O4—C10	1.366 (7)
C8—O2	1.3602 (19)	O4—C11	1.449 (7)
C8—C12	1.450 (2)	C11—H11A	0.9600
C9—C10'	1.496 (6)	C11—H11B	0.9600
C9—C10	1.511 (5)	C11—H11C	0.9600
C12—C13	1.321 (2)	O3'—C10'	1.185 (7)
C12—O5	1.3689 (19)	O4'—C10'	1.353 (7)
C13—C14	1.487 (3)	O4'—C11'	1.444 (7)
C13—H13	0.9300	C11'—H11D	0.9600
C14—O7	1.433 (2)	C11'—H11E	0.9600
C14—C15	1.532 (3)	C11'—H11F	0.9600
C14—H14	0.9800

O1—C1—C2	123.62 (16)	O6—C15—O5	111.78 (15)
O1—C1—C9	121.75 (16)	O6—C15—C14	106.56 (14)
C2—C1—C9	114.64 (14)	O5—C15—C14	106.08 (14)
C7—C2—C3	117.73 (17)	O6—C15—H15	110.8
C7—C2—C1	120.20 (16)	O5—C15—H15	110.8
C3—C2—C1	122.07 (17)	C14—C15—H15	110.8
C4—C3—C2	120.18 (19)	O7—C16—O6	104.35 (16)
C4—C3—H3	119.9	O7—C16—C17	111.85 (17)
C2—C3—H3	119.9	O6—C16—C17	110.54 (17)
C3—C4—C5	120.69 (19)	O7—C16—C18	108.59 (18)
C3—C4—H4	119.7	O6—C16—C18	108.04 (17)
C5—C4—H4	119.7	C17—C16—C18	113.0 (2)
C6—C5—C4	120.20 (19)	C16—C17—H17A	109.5
C6—C5—H5	119.9	C16—C17—H17B	109.5
C4—C5—H5	119.9	H17A—C17—H17B	109.5
C5—C6—C7	119.3 (2)	C16—C17—H17C	109.5
C5—C6—H6	120.3	H17A—C17—H17C	109.5
C7—C6—H6	120.3	H17B—C17—H17C	109.5
O2—C7—C6	116.50 (16)	C16—C18—H18A	109.5
O2—C7—C2	121.61 (15)	C16—C18—H18B	109.5
C6—C7—C2	121.88 (17)	H18A—C18—H18B	109.5
C9—C8—O2	122.55 (15)	C16—C18—H18C	109.5
C9—C8—C12	127.36 (14)	H18A—C18—H18C	109.5
O2—C8—C12	110.09 (12)	H18B—C18—H18C	109.5
C8—C9—C1	120.94 (15)	C8—O2—C7	119.96 (12)
C8—C9—C10'	122.4 (6)	C12—O5—C15	107.15 (12)
C1—C9—C10'	116.3 (6)	C15—O6—C16	109.09 (13)
C8—C9—C10	123.9 (6)	C16—O7—C14	109.45 (12)
C1—C9—C10	114.8 (6)	C10—O4—C11	116.5 (6)
C10'—C9—C10	11.9 (6)	O3—C10—O4	122.8 (7)
C13—C12—O5	114.86 (15)	O3—C10—C9	126.5 (8)
C13—C12—C8	129.24 (15)	O4—C10—C9	110.6 (6)
O5—C12—C8	115.90 (12)	C10'—O4'—C11'	113.1 (7)
C12—C13—C14	108.99 (15)	O3'—C10'—O4'	128.0 (7)
C12—C13—H13	125.5	O3'—C10'—C9	125.5 (8)
C14—C13—H13	125.5	O4'—C10'—C9	105.6 (6)
O7—C14—C13	114.10 (17)	O4'—C11'—H11D	109.5
O7—C14—C15	103.77 (14)	O4'—C11'—H11E	109.5
C13—C14—C15	102.88 (14)	H11D—C11'—H11E	109.5
O7—C14—H14	111.8	O4'—C11'—H11F	109.5
C13—C14—H14	111.8	H11D—C11'—H11F	109.5
C15—C14—H14	111.8	H11E—C11'—H11F	109.5

O1—C1—C2—C7	−179.32 (18)	O7—C14—C15—O5	117.25 (16)
C9—C1—C2—C7	0.8 (2)	C13—C14—C15—O5	−1.91 (19)
O1—C1—C2—C3	1.7 (3)	C9—C8—O2—C7	0.6 (2)
C9—C1—C2—C3	−178.20 (17)	C12—C8—O2—C7	−179.96 (14)
C7—C2—C3—C4	−0.6 (3)	C6—C7—O2—C8	177.25 (15)
C1—C2—C3—C4	178.34 (17)	C2—C7—O2—C8	−2.9 (2)
C2—C3—C4—C5	0.0 (3)	C13—C12—O5—C15	−0.2 (2)
C3—C4—C5—C6	0.4 (4)	C8—C12—O5—C15	−179.94 (15)
C4—C5—C6—C7	−0.1 (3)	O6—C15—O5—C12	117.13 (16)
C5—C6—C7—O2	179.26 (18)	C14—C15—O5—C12	1.38 (19)
C5—C6—C7—C2	−0.6 (3)	O5—C15—O6—C16	−98.06 (17)
C3—C2—C7—O2	−178.92 (16)	C14—C15—O6—C16	17.39 (19)
C1—C2—C7—O2	2.1 (3)	O7—C16—O6—C15	−26.20 (19)
C3—C2—C7—C6	1.0 (3)	C17—C16—O6—C15	94.21 (18)
C1—C2—C7—C6	−178.04 (17)	C18—C16—O6—C15	−141.63 (19)
O2—C8—C9—C1	2.4 (3)	O6—C16—O7—C14	24.8 (2)
C12—C8—C9—C1	−176.98 (17)	C17—C16—O7—C14	−94.74 (19)
O2—C8—C9—C10'	175.3 (5)	C18—C16—O7—C14	139.83 (19)
C12—C8—C9—C10'	−4.1 (6)	C13—C14—O7—C16	96.76 (18)
O2—C8—C9—C10	−170.6 (5)	C15—C14—O7—C16	−14.40 (19)
C12—C8—C9—C10	10.0 (5)	C11—O4—C10—O3	−4.9 (16)
O1—C1—C9—C8	177.14 (18)	C11—O4—C10—C9	177.9 (8)
C2—C1—C9—C8	−2.9 (3)	C8—C9—C10—O3	−107.4 (13)
O1—C1—C9—C10'	3.8 (5)	C1—C9—C10—O3	79.2 (13)
C2—C1—C9—C10'	−176.3 (5)	C10'—C9—C10—O3	−21 (4)
O1—C1—C9—C10	−9.3 (5)	C8—C9—C10—O4	69.7 (11)
C2—C1—C9—C10	170.7 (4)	C1—C9—C10—O4	−103.7 (10)
C9—C8—C12—C13	−179.15 (19)	C10'—C9—C10—O4	156 (6)
O2—C8—C12—C13	1.4 (3)	C11'—O4'—C10'—O3'	2.9 (18)
C9—C8—C12—O5	0.5 (3)	C11'—O4'—C10'—C9	171.8 (8)
O2—C8—C12—O5	−178.90 (14)	C8—C9—C10'—O3'	−90.0 (14)
O5—C12—C13—C14	−1.1 (2)	C1—C9—C10'—O3'	83.2 (14)
C8—C12—C13—C14	178.57 (17)	C10—C9—C10'—O3'	169 (7)
C12—C13—C14—O7	−109.86 (17)	C8—C9—C10'—O4'	100.7 (10)
C12—C13—C14—C15	1.8 (2)	C1—C9—C10'—O4'	−86.1 (10)
O7—C14—C15—O6	−1.99 (18)	C10—C9—C10'—O4'	−1 (5)
C13—C14—C15—O6	−121.15 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O7ⁱ	0.93	2.59	3.296 (2)	133
C13—H13···O3ⁱⁱ	0.93	2.59	3.230 (10)	127
C14—H14···O1ⁱⁱ	0.98	2.50	3.429 (2)	159
C18—H18C···O1ⁱⁱⁱ	0.96	2.55	3.460 (3)	159

Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O7ⁱ	0.93	2.59	3.296 (2)	133
C13—H13···O3ⁱⁱ	0.93	2.59	3.230 (10)	127
C14—H14···O1ⁱⁱ	0.98	2.50	3.429 (2)	159
C18—H18C···O1ⁱⁱⁱ	0.96	2.55	3.460 (3)	159

Symmetry codes: (i) −x+3/2, −y+1, z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+2, y+1/2, −z+1/2.

Acknowledgements

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

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

Methyl 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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organic compounds

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