(1R,3R,4R,6S)-4-(7-Meth-oxy-2-oxo-2H-chromen-6-yl)-1-methyl-3,6-dioxa-bicyclo-[3.1.0]hexan-2-yl acetate.

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 intra-molecular C-H⋯O hydrogen bond occurs. The carbonyl O atom is disordered in a 0.57 (8):0.43 (8) ratio. In the crystal, mol-ecules 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 = 332.31

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.136

S = 1.06

2123 reflections

223 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.24 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047617/bx2427sup1.cif

Click here for additional data file.

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H16O7	F(000) = 348
Mr = 332.31	Dx = 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

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

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(Fo2) + (0.0701P)2 + 0.1456P] where P = (Fo2 + 2Fc2)/3
2123 reflections	(Δ/σ)max < 0.001
223 parameters	Δρmax = 0.47 e Å−3
2 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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

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

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O19A i	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) ; (ii) ; (iii) .