(1R,3R,4R,6S)-4-(7-Meth­oxy-2-oxo-2H-chromen-6-yl)-1-methyl-3,6-dioxa­bicyclo­[3.1.0]hexan-2-yl acetate

Phakhodee, W.; Laphookhieo, S.; Prior, T.J.; Rujiwatra, A.

doi:10.1107/S1600536812047617

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3421-o3422

doi:10.1107/S1600536812047617

Open

access

(1R,3R,4R,6S)-4-(7-Methoxy-2-oxo-2H-chromen-6-yl)-1-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl acetate

Wong Phakhodee,^a Surat Laphookhieo,^a Timothy John Prior ^b and Apinpus Rujiwatra ^c ^*

^aNatural Products Research Laboratory, School of Science, Mae Fah Luang, University, Tasud, Muang, Chiang Rai 57100, Thailand, ^bDepartment of Chemistry, University of Hull, Cottingham Road, Hull HU6 7RX, England, and ^cDepartment of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai 50200, Thailand
^*Correspondence e-mail: apinpus@gmail.com

(Received 26 October 2012; accepted 20 November 2012; online 24 November 2012)

In the title compound, C₁₇H₁₆O₇, which was isolated from the leaves of Micromelum integerrimum, the furan ring adopts an envelope conformation with the O atom as the flap. An intramolecular C—H⋯O hydrogen bond occurs. The carbonyl O atom is disordered in a 0.57 (8):0.43 (8) ratio. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds into a C(10) chain along [010].

Related literature

Micromelum integerrimum is a shrub in the Rutacae family containing the coumarin molecule, micromelin, as the major chemical constituent (Cassady et al., 1979 ). Many coumarins including micromelin have been extracted from Rutacae plants, and for some their cytotoxicity has been investigated (Sripisut et al., 2012 ; He et al., 2001 ). For previous reports on the isolation of micromelin (micromelumin) from a Northern Queensland collection, an Assamese collection, and a Northeast Thailand collection, see: Lamberton et al. (1967 ); Das et al. (1984 ); Siridechakorn et al. (2012 ). For detailed H¹ NMR spectroscopic data, see: Das et al. (1984); Siridechakorn et al. (2012). For a phytochemical investigation, see: Siridechakorn et al. (2012). For a closely related micromelin structure, C₁₅H₁₂O₆, see: Fun et al. (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₇H₁₆O₇
M_r = 332.31
Monoclinic, P 2₁
a = 10.4825 (16) Å
b = 6.9213 (9) Å
c = 11.0212 (18) Å
β = 95.970 (7)°
V = 795.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.64 × 0.32 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.653, T_max = 0.746
4381 measured reflections
2123 independent reflections
1692 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.136
S = 1.06
2123 reflections
223 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O19Aⁱ	1.07 (3)	2.46 (2)	3.064 (8)	114 (1)
C5—H5⋯O13	1.01 (3)	2.58 (3)	3.403 (3)	139 (1)
C12—H12⋯O2ⁱⁱ	0.98	2.35	3.282 (5)	158
C16—H16B⋯O2ⁱⁱⁱ	0.96	2.54	3.419 (4)	153
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007 ); software used to prepare material for publication: publCIF (Westrip, 2010 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812047617/bx2427sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047617/bx2427Isup2.hkl

checkCIF report

Comment top

Micromelum integerrimum is a shrub in the Rutacae family containing the coumarin molecule, micromilin, as the major chemical constituent (Cassady et al., 1979). Many coumarins including micromilin have been extracted from Rutacae plants, and for some their cytotoxicity has been investigated (Sripisut et al., 2012; He et al., 2001). In the attempt to investigate the chemical constitutents of the extract of Micromelum integerrimum leaves collected from Chiang Rai province in the Northern part of Thailand (March 2012), the colourless crystals of the title compound have been isolated and examined.

The absolute configurations of the four chiral centres in the molecule, (I) (C11, C12, C13, and C14) were assigned from a previous report (Das et al., 1984) as R, R, R and S, respectively. The benzene and dihydropyran ring system (C2–C10/O1) and also the carboxyl O2 and the methoxy O3 atoms are co-planar with the r.m.s. 0.004 (3) Å (Spek, 2009). A deviation of atoms O2 and O3 from the benzene and dihydropyran ring system are 0.028 (2) Å and 0.040 (2) Å, respectively. The five-membered furan ring (C11–C14/O11) shows envelope conformation with the puckering atom O11 of 0.075 (2) Å, and forms an angle of 66.11 (9)° to the twelve-membered benzene–dihydropyran due to free rotation about the C6—C11 bond. The puckering parameters Q and ϕ of the furan ring are 0.116 (2) Å and 176.4 (12)°, respectively (Cremer & Pople, 1975). The orientation of the oxiran ring (C12–C13/O12) attached to the furan can be defined by the dihedral angle being 79.5 (2)° with atom O12 of the oxirane ring located 1.250 (2) Å away from the furan plane. Regarding the acetate group, atom O19 shows minor positional disorder over two sites. The acetate O13 is arranged at 64.19 (15)° in reference to the furan plane, and the torsion angle measured on C14–O13–C17–C18 is 171.6 (2)°.In the crystal of (I), the molecules are linked by weak C—H···O hydrogen-bonding interactions into a chain along [010] with set-graph notation C(10), (Bernstein, et al., 1995)

Related literature top

Micromelum integerrimum is a shrub in the Rutacae family containing the coumarin molecule, micromelin, as the major chemical constituent (Cassady et al., 1979). Many coumarins including micromelin have been extracted from Rutacae plants, and for some their cytotoxicity has been investigated (Sripisut et al., 2012; He et al., 2001). For previous reports on the isolation of micromelin (micromelumin) from a Northern Queensland collection, an Assamese collection, and a Northeast Thailand collection, see: Lamberton et al. (1967); Das et al. (1984); Siridechakorn et al. (2012). For detailed H¹ NMR spectroscopic data, see: Das et al. (1984); Siridechakorn et al. (2012). For a phytochemical investigation, see: Siridechakorn et al. (2012). For a closely related micromelin structure, C₁₅H₁₂O₆, see: Fun et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was obtained from an acetone extract of Micromelum integerrimum leaves (0.55 kg), which are collected from Chiang Rai Province, Thailand. From seven fractions (A—G) yielded by column chromatography using hexanes-acetone, the title compound (295.9 mg) was isolated from fraction D by also column chromatography using 2% acetone-CH₂Cl₂. The crystals were then crystallized by slowly evaporation of the solvent.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at 50% probability level.
	Fig. 2. A view of (I), showing the C(10) chains along [010] constructed via C—H···O hydrogen bonds. Hydrogen bonds are depicted as dashed lines [symmetry-code:(i) -x,1/2+y, 1-z]

(1R,3R,4R,6S)-4-(7-Methoxy-2-oxo-2H- chromen-6-yl)-1-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl acetate top

Crystal data top

C₁₇H₁₆O₇	F(000) = 348
M_r = 332.31	D_x = 1.388 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3003 reflections
a = 10.4825 (16) Å	θ = 1.9–28.3°
b = 6.9213 (9) Å	µ = 0.11 mm⁻¹
c = 11.0212 (18) Å	T = 298 K
β = 95.970 (7)°	Block, colourless
V = 795.3 (2) Å³	0.64 × 0.32 × 0.24 mm
Z = 2

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2123 independent reflections
Radiation source: fine-focus sealed tube	1692 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 28.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→8
T_min = 0.653, T_max = 0.746	k = −7→9
4381 measured reflections	l = −14→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0701P)² + 0.1456P] where P = (F_o² + 2F_c²)/3
2123 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.47 e Å⁻³
2 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₁₆O₇	V = 795.3 (2) Å³
M_r = 332.31	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.4825 (16) Å	µ = 0.11 mm⁻¹
b = 6.9213 (9) Å	T = 298 K
c = 11.0212 (18) Å	0.64 × 0.32 × 0.24 mm
β = 95.970 (7)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2123 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	1692 reflections with I > 2σ(I)
T_min = 0.653, T_max = 0.746	R_int = 0.021
4381 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	2 restraints
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.47 e Å⁻³
2123 reflections	Δρ_min = −0.24 e Å⁻³
223 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)
O1	−0.09274 (16)	0.0334 (4)	0.56547 (17)	0.0485 (5)
C2	−0.2211 (2)	0.0363 (5)	0.5224 (3)	0.0509 (6)
O2	−0.2958 (2)	0.0392 (4)	0.5982 (2)	0.0701 (7)
C3	−0.2509 (2)	0.0355 (5)	0.3921 (3)	0.0542 (7)
H3	−0.335 (3)	0.0402 (6)	0.3602 (13)	0.065*
C4	−0.1595 (2)	0.0280 (5)	0.3155 (3)	0.0490 (6)
H4	−0.1858 (8)	0.0256 (5)	0.219 (3)	0.059*
C5	0.0765 (2)	0.0093 (4)	0.2907 (2)	0.0434 (6)
H5	0.0579 (6)	0.0024 (5)	0.199 (3)	0.052*
C6	0.2015 (2)	0.0050 (4)	0.3416 (2)	0.0438 (6)
C7	0.2260 (2)	0.0189 (4)	0.4699 (2)	0.0425 (5)
O3	0.35235 (16)	0.0218 (4)	0.51324 (18)	0.0587 (6)
C16	0.3858 (3)	0.0418 (6)	0.6410 (3)	0.0572 (7)
H16A	0.3431	0.1526	0.6702	0.086*
H16B	0.4769	0.0582	0.6572	0.086*
H16C	0.3600	−0.0719	0.6820	0.086*
C8	0.1272 (2)	0.0280 (5)	0.5436 (2)	0.0423 (5)
H8	0.1452 (6)	0.0344 (5)	0.633 (3)	0.051*
C9	0.0026 (2)	0.0280 (4)	0.4886 (2)	0.0389 (5)
C10	−0.0266 (2)	0.0232 (4)	0.3624 (2)	0.0408 (5)
C11	0.3156 (3)	−0.0214 (5)	0.2692 (3)	0.0502 (7)
H11	0.3788	−0.1042	0.3159	0.060*
O11	0.2824 (2)	−0.1069 (4)	0.1510 (2)	0.0606 (6)
C12	0.3783 (3)	0.1663 (6)	0.2434 (3)	0.0563 (8)
H12	0.3774	0.2751	0.3003	0.068*
O12	0.48617 (19)	0.1365 (5)	0.1725 (2)	0.0697 (7)
C13	0.3647 (3)	0.1984 (6)	0.1116 (3)	0.0621 (8)
C14	0.2937 (3)	0.0253 (6)	0.0571 (3)	0.0599 (8)
H14	0.3396	−0.0323	−0.0070	0.072*
O13	0.1675 (2)	0.0904 (4)	0.00763 (19)	0.0656 (7)
C15	0.3633 (4)	0.3895 (9)	0.0470 (4)	0.0931 (14)
H15A	0.2762	0.4289	0.0248	0.140*
H15B	0.4066	0.3773	−0.0252	0.140*
H15C	0.4062	0.4845	0.1000	0.140*
C17	0.1085 (3)	−0.0092 (6)	−0.0852 (3)	0.0652 (9)
C18	−0.0245 (4)	0.0466 (8)	−0.1189 (4)	0.0793 (11)
H18A	−0.0547	−0.0112	−0.1957	0.119*
H18B	−0.0301	0.1847	−0.1258	0.119*
H18C	−0.0762	0.0031	−0.0573	0.119*
O19A	0.1483 (6)	−0.1679 (10)	−0.1149 (6)	0.0843 (12)*	0.567 (8)
O19B	0.1763 (7)	−0.0896 (14)	−0.1535 (7)	0.0843 (12)*	0.433 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0370 (8)	0.0543 (11)	0.0556 (10)	0.0019 (10)	0.0112 (7)	0.0022 (11)
C2	0.0374 (12)	0.0414 (14)	0.0750 (18)	0.0000 (13)	0.0113 (12)	0.0053 (16)
O2	0.0463 (10)	0.0742 (16)	0.0943 (16)	−0.0031 (13)	0.0283 (10)	0.0057 (15)
C3	0.0318 (11)	0.0494 (15)	0.0794 (19)	−0.0042 (14)	−0.0037 (11)	0.0071 (17)
C4	0.0404 (12)	0.0459 (14)	0.0585 (15)	−0.0051 (14)	−0.0054 (11)	0.0033 (15)
C5	0.0440 (12)	0.0436 (14)	0.0424 (12)	−0.0009 (12)	0.0030 (10)	0.0011 (12)
C6	0.0382 (11)	0.0446 (15)	0.0489 (13)	0.0013 (12)	0.0067 (10)	−0.0025 (13)
C7	0.0328 (10)	0.0427 (13)	0.0513 (13)	0.0040 (12)	0.0007 (9)	0.0008 (13)
O3	0.0323 (8)	0.0833 (16)	0.0599 (11)	0.0021 (12)	0.0015 (7)	−0.0034 (13)
C16	0.0388 (12)	0.0655 (19)	0.0640 (16)	0.0071 (15)	−0.0103 (11)	−0.0031 (17)
C8	0.0380 (11)	0.0451 (13)	0.0433 (12)	0.0010 (13)	0.0016 (9)	−0.0007 (13)
C9	0.0344 (10)	0.0341 (11)	0.0486 (12)	0.0009 (12)	0.0059 (9)	0.0029 (12)
C10	0.0354 (10)	0.0373 (12)	0.0491 (12)	−0.0022 (12)	0.0006 (9)	0.0003 (12)
C11	0.0416 (13)	0.0589 (18)	0.0509 (14)	0.0051 (13)	0.0080 (11)	−0.0103 (13)
O11	0.0620 (13)	0.0600 (12)	0.0615 (13)	0.0007 (11)	0.0147 (10)	−0.0160 (11)
C12	0.0384 (13)	0.075 (2)	0.0578 (16)	−0.0085 (15)	0.0171 (12)	−0.0156 (16)
O12	0.0379 (10)	0.110 (2)	0.0636 (13)	−0.0054 (12)	0.0170 (9)	−0.0161 (14)
C13	0.0450 (15)	0.082 (2)	0.0624 (18)	−0.0085 (17)	0.0210 (13)	−0.0089 (18)
C14	0.0442 (13)	0.083 (2)	0.0541 (15)	0.0060 (18)	0.0143 (11)	−0.0172 (18)
O13	0.0501 (11)	0.0877 (18)	0.0588 (12)	0.0055 (11)	0.0046 (9)	−0.0196 (12)
C15	0.081 (3)	0.104 (3)	0.099 (3)	−0.023 (3)	0.030 (2)	0.021 (3)
C17	0.0663 (18)	0.083 (3)	0.0468 (14)	0.0084 (18)	0.0062 (13)	−0.0103 (16)
C18	0.071 (2)	0.092 (3)	0.072 (2)	−0.001 (2)	−0.0103 (17)	0.006 (2)

Geometric parameters (Å, º) top

O1—C9	1.377 (3)	C11—O11	1.441 (3)
O1—C2	1.380 (3)	C11—C12	1.496 (5)
C2—O2	1.203 (3)	C11—H11	0.9800
C2—C3	1.438 (4)	O11—C14	1.396 (5)
C3—C4	1.343 (4)	C12—O12	1.455 (3)
C3—H3	0.9168	C12—C13	1.463 (4)
C4—C10	1.435 (3)	C12—H12	0.9800
C4—H4	1.0676	O12—C13	1.441 (4)
C5—C6	1.371 (3)	C13—C15	1.501 (7)
C5—C10	1.406 (3)	C13—C14	1.502 (5)
C5—H5	1.0053	C14—O13	1.450 (4)
C6—C7	1.413 (4)	C14—H14	0.9800
C6—C11	1.517 (3)	O13—C17	1.332 (4)
C7—O3	1.361 (3)	C15—H15A	0.9600
C7—C8	1.383 (3)	C15—H15B	0.9600
O3—C16	1.422 (3)	C15—H15C	0.9600
C16—H16A	0.9600	C17—O19B	1.222 (7)
C16—H16B	0.9600	C17—O19A	1.231 (7)
C16—H16C	0.9600	C17—C18	1.456 (5)
C8—C9	1.382 (3)	C18—H18A	0.9600
C8—H8	0.9857	C18—H18B	0.9600
C9—C10	1.393 (4)	C18—H18C	0.9600

C9—O1—C2	122.2 (2)	C6—C11—H11	108.7
O2—C2—O1	116.3 (3)	C14—O11—C11	111.7 (3)
O2—C2—C3	127.2 (3)	O12—C12—C13	59.20 (19)
O1—C2—C3	116.5 (2)	O12—C12—C11	111.1 (3)
C4—C3—C2	122.2 (2)	C13—C12—C11	108.8 (3)
C4—C3—H3	118.9	O12—C12—H12	120.8
C2—C3—H3	118.9	C13—C12—H12	120.8
C3—C4—C10	120.3 (2)	C11—C12—H12	120.8
C3—C4—H4	119.9	C13—O12—C12	60.65 (19)
C10—C4—H4	119.9	O12—C13—C12	60.14 (19)
C6—C5—C10	121.9 (2)	O12—C13—C15	116.6 (3)
C6—C5—H5	119.0	C12—C13—C15	126.9 (4)
C10—C5—H5	119.0	O12—C13—C14	109.0 (3)
C5—C6—C7	118.4 (2)	C12—C13—C14	105.6 (3)
C5—C6—C11	124.1 (2)	C15—C13—C14	122.2 (3)
C7—C6—C11	117.6 (2)	O11—C14—O13	109.8 (2)
O3—C7—C8	123.6 (2)	O11—C14—C13	107.6 (3)
O3—C7—C6	115.0 (2)	O13—C14—C13	107.3 (3)
C8—C7—C6	121.4 (2)	O11—C14—H14	110.7
C7—O3—C16	118.7 (2)	O13—C14—H14	110.7
O3—C16—H16A	109.5	C13—C14—H14	110.7
O3—C16—H16B	109.5	C17—O13—C14	117.4 (3)
H16A—C16—H16B	109.5	C13—C15—H15A	109.5
O3—C16—H16C	109.5	C13—C15—H15B	109.5
H16A—C16—H16C	109.5	H15A—C15—H15B	109.5
H16B—C16—H16C	109.5	C13—C15—H15C	109.5
C9—C8—C7	118.3 (2)	H15A—C15—H15C	109.5
C9—C8—H8	120.9	H15B—C15—H15C	109.5
C7—C8—H8	120.9	O19B—C17—O13	117.1 (4)
O1—C9—C8	116.3 (2)	O19A—C17—O13	121.5 (4)
O1—C9—C10	121.2 (2)	O19B—C17—C18	124.5 (4)
C8—C9—C10	122.5 (2)	O19A—C17—C18	120.7 (4)
C9—C10—C5	117.4 (2)	O13—C17—C18	114.4 (3)
C9—C10—C4	117.6 (2)	C17—C18—H18A	109.5
C5—C10—C4	125.0 (2)	C17—C18—H18B	109.5
O11—C11—C12	104.7 (2)	H18A—C18—H18B	109.5
O11—C11—C6	113.3 (2)	C17—C18—H18C	109.5
C12—C11—C6	112.4 (2)	H18A—C18—H18C	109.5
O11—C11—H11	108.7	H18B—C18—H18C	109.5
C12—C11—H11	108.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O19Aⁱ	1.07 (3)	2.46 (2)	3.064 (8)	114 (1)
C5—H5···O13	1.01 (3)	2.58 (3)	3.403 (3)	139 (1)
C12—H12···O2ⁱⁱ	0.98	2.35	3.282 (5)	158
C16—H16B···O2ⁱⁱⁱ	0.96	2.54	3.419 (4)	153

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₇
M_r	332.31
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	10.4825 (16), 6.9213 (9), 11.0212 (18)
β (°)	95.970 (7)
V (Å³)	795.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.64 × 0.32 × 0.24

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.653, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	4381, 2123, 1692
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.136, 1.06
No. of reflections	2123
No. of parameters	223
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.24

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2007), publCIF (Westrip, 2010) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O19Aⁱ	1.07 (3)	2.463 (17)	3.064 (8)	114.4 (7)
C5—H5···O13	1.01 (3)	2.58 (3)	3.403 (3)	138.7 (6)
C12—H12···O2ⁱⁱ	0.98	2.35	3.282 (5)	158
C16—H16B···O2ⁱⁱⁱ	0.96	2.54	3.419 (4)	153

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

Acknowledgements

The Thailand Research Fund is acknowledged for a research grant.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. (2007). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (1997). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2008). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cassady, J. M., Ojima, N., Chang, C. J. & McLaughlin, J. L. (1979). J. Nat. Prod. 42, 274–278. CrossRef CAS PubMed Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Das, S., Baruah, R. H., Sharma, R. P., Barua, J. N., Kulanthaivel, P. & Herz, W. (1984). Phytochemistry, 23, 2317–2321. CrossRef CAS Web of Science Google Scholar
Fun, H.-K., Siridechakorn, I., Laphookhieo, S. & Chantrapromma, S. (2011). Acta Cryst. E67, o1706–o1707. Web of Science CSD CrossRef IUCr Journals Google Scholar
He, H. P., Zou, Y., Shen, Y. M., Hao, X. Y., Zuo, G. Y. & Hao, X. J. (2001). Chin. Chem. Lett. 12, 603–606. CAS Google Scholar
Lamberton, J. A., Price, J. R. & Redcliffe, A. H. (1967). Aust. J. Chem. 20, 973–979. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siridechakorn, I., Ritthiwigrom, T. & Laphookhieo, S. (2012). Biochem. Syst. Ecol. 40, 69–70. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sripisut, T., Cheenpracha, S., Ritthiwigrom, T., Prawat, U. & Laphookhieo, S. (2012). Rec. Nat. Prod. 6, 386–389. CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3421-o3422

doi:10.1107/S1600536812047617

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

(1R,3R,4R,6S)-4-(7-Meth­­oxy-2-oxo-2H-chromen-6-yl)-1-methyl-3,6-dioxa­bi­cyclo­[3.1.0]hexan-2-yl acetate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(1R,3R,4R,6S)-4-(7-Methoxy-2-oxo-2H-chromen-6-yl)-1-methyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl acetate