4-Oxo-2-phenylchroman-6-yl propionate.

In the structure of the title compound, C(18)H(16)O(4), both the S and R enanti-omers appear to occupy in a random way four symmetry-equivalent sites of the unit cell in an approximately 4:1/1:4 ratio. The chiral C atom of the pyrone ring together with the phenyl ring bonded to this atom are disordered over two positions, the occupancy factor of the major component being 0.809 (5). Adjacent molecules are linked by weak C-H⋯O hydrogen bonds.

Related literature

For background to flavonoids and their properties, see: Harborne & Baxter (1999 ▶); Harborne & Williams (2000 ▶); Di Carlo et al.,(1999 ▶); Rice-Evans (2004 ▶); Wang (2000 ▶); Halliwell (1996 ▶); Rice-Evans et al. (1996 ▶); Kostrzewa-Susłow et al. (2008 ▶). For related structures, see: Shoja et al. (1998 ▶); Białońska et al. (2007 ▶).

Experimental

Crystal data

C18H16O4

M = 296.31

Monoclinic,

a = 7.863 (2) Å

b = 17.876 (4) Å

c = 10.731 (2) Å

β = 101.28 (3)°

V = 1479.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.32 × 0.15 × 0.09 mm

Data collection

Kuma KM4 CCD diffractometer

23501 measured reflections

5512 independent reflections

1906 reflections with I > 2σ(I)

R int = 0.126

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.140

S = 0.86

5512 reflections

263 parameters

186 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis CCD, (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012298/hg2666sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012298/hg2666Isup2.hkl

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

C18H16O4	F(000) = 624
Mr = 296.31	Dx = 1.331 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2758 reflections
a = 7.863 (2) Å	θ = 2.9–36.8°
b = 17.876 (4) Å	µ = 0.09 mm−1
c = 10.731 (2) Å	T = 100 K
β = 101.28 (3)°	Plate, colorless
V = 1479.2 (6) Å3	0.32 × 0.15 × 0.09 mm
Z = 4

Kuma KM4 CCD diffractometer	1906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.126
graphite	θmax = 33.0°, θmin = 2.9°
ω scan	h = −9→12
23501 measured reflections	k = −27→27
5512 independent reflections	l = −16→16

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 0.86	w = 1/[σ2(Fo2) + (0.0501P)2] where P = (Fo2 + 2Fc2)/3
5512 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.26 e Å−3
186 restraints	Δρmin = −0.20 e Å−3

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 > 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	0.08199 (17)	0.09868 (7)	0.26522 (11)	0.0360 (3)
C3	−0.2206 (2)	0.11679 (11)	0.28343 (16)	0.0333 (5)
H3C	−0.2405	0.1702	0.2607	0.040*	0.191 (5)
H3D	−0.3312	0.0899	0.2539	0.040*	0.191 (5)
H3A	−0.3199	0.1516	0.2612	0.040*	0.809 (5)
H3B	−0.2583	0.0672	0.2469	0.040*	0.809 (5)
C2	−0.0717 (3)	0.14510 (17)	0.2248 (2)	0.0291 (7)	0.809 (5)
H2	−0.0437	0.1975	0.2544	0.035*	0.809 (5)
C2A	−0.0799 (12)	0.0847 (7)	0.2107 (8)	0.029 (3)	0.191 (5)
H2A	−0.0935	0.0290	0.2091	0.034*	0.191 (5)
O4	−0.27867 (17)	0.11284 (9)	0.49357 (12)	0.0510 (4)
C4	−0.1720 (3)	0.11027 (12)	0.42566 (17)	0.0367 (5)
C5	0.0761 (3)	0.09439 (11)	0.60752 (17)	0.0354 (5)
H5	−0.0024	0.0986	0.6641	0.042*
C6	0.2489 (2)	0.08326 (10)	0.65442 (16)	0.0325 (5)
C7	0.3650 (3)	0.07588 (11)	0.57403 (18)	0.0378 (5)
H7	0.4845	0.0680	0.6080	0.045*
C8	0.3072 (2)	0.07993 (11)	0.44393 (17)	0.0375 (5)
H8	0.3865	0.0740	0.3883	0.045*
C9	0.1325 (2)	0.09266 (10)	0.39496 (16)	0.0300 (4)
C10	0.0149 (2)	0.09958 (10)	0.47656 (16)	0.0310 (4)
C11	−0.1170 (4)	0.1450 (3)	0.0831 (3)	0.0303 (7)	0.809 (5)
C12	−0.1411 (5)	0.0793 (2)	0.0138 (4)	0.0366 (9)	0.809 (5)
H12	−0.1219	0.0327	0.0570	0.044*	0.809 (5)
C13	−0.1934 (7)	0.0798 (3)	−0.1190 (4)	0.0397 (10)	0.809 (5)
H13	−0.2060	0.0342	−0.1652	0.048*	0.809 (5)
C14	−0.2265 (7)	0.1475 (3)	−0.1823 (5)	0.0382 (11)	0.809 (5)
H14	−0.2649	0.1483	−0.2719	0.046*	0.809 (5)
C15	−0.2034 (5)	0.2140 (2)	−0.1141 (3)	0.0417 (8)	0.809 (5)
H15	−0.2251	0.2605	−0.1572	0.050*	0.809 (5)
C16	−0.1478 (4)	0.2128 (2)	0.0186 (3)	0.0376 (7)	0.809 (5)
H16	−0.1311	0.2585	0.0646	0.045*	0.809 (5)
C11A	−0.119 (2)	0.1114 (11)	0.0698 (17)	0.034 (3)	0.191 (5)
C12A	−0.172 (2)	0.0636 (11)	−0.0273 (17)	0.037 (3)	0.191 (5)
H12A	−0.1752	0.0112	−0.0136	0.045*	0.191 (5)
C13A	−0.220 (3)	0.0935 (16)	−0.147 (2)	0.040 (3)	0.191 (5)
H13A	−0.2685	0.0616	−0.2153	0.048*	0.191 (5)
C14A	−0.201 (3)	0.1676 (14)	−0.170 (2)	0.035 (2)	0.191 (5)
H14A	−0.2292	0.1866	−0.2541	0.042*	0.191 (5)
C15A	−0.142 (2)	0.2133 (9)	−0.0714 (15)	0.038 (2)	0.191 (5)
H15A	−0.1262	0.2652	−0.0847	0.046*	0.191 (5)
C16A	−0.1042 (19)	0.1832 (10)	0.0494 (14)	0.033 (2)	0.191 (5)
H16A	−0.0662	0.2154	0.1197	0.040*	0.191 (5)
O17	0.30900 (16)	0.07682 (7)	0.78730 (11)	0.0366 (3)
O18	0.28558 (19)	0.20177 (8)	0.80597 (12)	0.0481 (4)
C18	0.3155 (2)	0.14193 (13)	0.85498 (18)	0.0368 (5)
C19	0.3615 (3)	0.12719 (12)	0.99504 (17)	0.0429 (5)
H19A	0.4743	0.1008	1.0143	0.051*
H19B	0.2729	0.0937	1.0192	0.051*
C20	0.3734 (3)	0.19745 (13)	1.07435 (19)	0.0525 (6)
H20A	0.4030	0.1842	1.1646	0.079*
H20B	0.2615	0.2234	1.0570	0.079*
H20C	0.4632	0.2303	1.0529	0.079*

	U11	U22	U33	U12	U13	U23
O1	0.0336 (8)	0.0530 (9)	0.0217 (7)	0.0076 (6)	0.0058 (6)	0.0035 (6)
C3	0.0309 (10)	0.0463 (12)	0.0221 (9)	−0.0009 (9)	0.0037 (8)	0.0026 (8)
C2	0.0281 (13)	0.0357 (18)	0.0218 (11)	0.0042 (12)	0.0009 (9)	0.0039 (11)
C2A	0.029 (6)	0.044 (8)	0.015 (4)	−0.001 (5)	0.009 (4)	0.006 (4)
O4	0.0312 (8)	0.0941 (12)	0.0288 (7)	−0.0055 (8)	0.0086 (6)	0.0014 (8)
C4	0.0309 (10)	0.0531 (13)	0.0255 (10)	−0.0048 (10)	0.0045 (9)	−0.0011 (9)
C5	0.0328 (11)	0.0499 (14)	0.0244 (10)	−0.0013 (9)	0.0081 (8)	0.0012 (9)
C6	0.0368 (11)	0.0385 (12)	0.0220 (9)	0.0016 (9)	0.0050 (8)	0.0033 (8)
C7	0.0312 (11)	0.0504 (13)	0.0309 (10)	0.0068 (10)	0.0037 (8)	0.0064 (9)
C8	0.0321 (11)	0.0543 (14)	0.0264 (10)	0.0089 (10)	0.0062 (8)	0.0044 (9)
C9	0.0351 (11)	0.0333 (11)	0.0207 (9)	0.0024 (9)	0.0030 (8)	0.0024 (8)
C10	0.0297 (10)	0.0398 (12)	0.0235 (10)	−0.0008 (8)	0.0051 (8)	0.0019 (8)
C11	0.0287 (13)	0.039 (2)	0.0252 (14)	0.0019 (18)	0.0085 (10)	−0.0011 (15)
C12	0.0418 (19)	0.041 (2)	0.0261 (19)	0.0011 (16)	0.0045 (16)	0.0034 (16)
C13	0.042 (2)	0.050 (2)	0.027 (2)	0.0019 (17)	0.0054 (16)	0.0004 (16)
C14	0.036 (2)	0.057 (3)	0.0211 (15)	0.0063 (19)	0.0045 (13)	−0.0009 (18)
C15	0.049 (2)	0.0538 (18)	0.0220 (16)	0.0168 (16)	0.0050 (13)	0.0067 (15)
C16	0.0494 (18)	0.0398 (18)	0.0238 (15)	0.0082 (14)	0.0077 (12)	0.0030 (13)
C11A	0.038 (4)	0.036 (5)	0.028 (4)	0.003 (4)	0.004 (4)	−0.004 (4)
C12A	0.040 (4)	0.045 (4)	0.026 (5)	0.003 (4)	0.004 (4)	−0.004 (4)
C13A	0.038 (4)	0.052 (5)	0.029 (5)	0.006 (4)	0.005 (4)	0.004 (4)
C14A	0.037 (4)	0.047 (4)	0.023 (4)	0.006 (4)	0.011 (4)	0.005 (4)
C15A	0.043 (4)	0.041 (4)	0.028 (4)	0.008 (4)	0.001 (4)	0.003 (4)
C16A	0.041 (4)	0.032 (5)	0.025 (4)	0.012 (4)	0.003 (4)	−0.001 (4)
O17	0.0386 (8)	0.0457 (9)	0.0231 (7)	0.0039 (7)	−0.0001 (6)	0.0015 (6)
O18	0.0642 (10)	0.0454 (9)	0.0318 (8)	−0.0007 (8)	0.0023 (7)	0.0045 (7)
C18	0.0311 (11)	0.0506 (14)	0.0284 (10)	0.0003 (10)	0.0047 (8)	0.0015 (10)
C19	0.0454 (12)	0.0564 (14)	0.0252 (10)	0.0072 (11)	0.0027 (9)	0.0026 (9)
C20	0.0544 (14)	0.0722 (17)	0.0289 (11)	0.0118 (12)	0.0032 (10)	−0.0057 (11)

O1—C2A	1.317 (10)	C12—C13	1.404 (5)
O1—C9	1.375 (2)	C12—H12	0.9500
O1—C2	1.460 (3)	C13—C14	1.386 (6)
C3—C4	1.504 (2)	C13—H13	0.9500
C3—C2	1.520 (3)	C14—C15	1.390 (6)
C3—C2A	1.581 (10)	C14—H14	0.9500
C3—H3C	0.9900	C15—C16	1.405 (4)
C3—H3D	0.9900	C15—H15	0.9500
C3—H3A	0.9899	C16—H16	0.9500
C3—H3B	0.9901	C11A—C16A	1.31 (2)
C2—C11	1.492 (4)	C11A—C12A	1.35 (2)
C2—H2	1.0000	C12A—C13A	1.37 (2)
C2A—C11A	1.558 (19)	C12A—H12A	0.9500
C2A—H3B	1.5579	C13A—C14A	1.36 (3)
C2A—H2A	1.0000	C13A—H13A	0.9500
O4—C4	1.215 (2)	C14A—C15A	1.35 (3)
C4—C10	1.476 (3)	C14A—H14A	0.9500
C5—C6	1.368 (3)	C15A—C16A	1.381 (19)
C5—C10	1.397 (2)	C15A—H15A	0.9500
C5—H5	0.9500	C16A—H16A	0.9500
C6—C7	1.379 (3)	O17—C18	1.367 (2)
C6—O17	1.416 (2)	O18—C18	1.195 (2)
C7—C8	1.383 (3)	C18—C19	1.499 (3)
C7—H7	0.9500	C19—C20	1.510 (3)
C8—C9	1.390 (3)	C19—H19A	0.9900
C8—H8	0.9500	C19—H19B	0.9900
C9—C10	1.398 (2)	C20—H20A	0.9800
C11—C12	1.383 (4)	C20—H20B	0.9800
C11—C16	1.394 (4)	C20—H20C	0.9800
C2A—O1—C9	119.8 (4)	C8—C9—C10	120.23 (16)
C2A—O1—C2	45.9 (5)	C5—C10—C9	118.98 (18)
C9—O1—C2	113.80 (15)	C5—C10—C4	120.20 (17)
C4—C3—C2	112.49 (16)	C9—C10—C4	120.80 (16)
C4—C3—C2A	114.1 (4)	C12—C11—C16	118.7 (3)
C2—C3—C2A	41.1 (4)	C12—C11—C2	122.0 (4)
C4—C3—H3C	108.7	C16—C11—C2	119.2 (3)
C2—C3—H3C	71.0	C11—C12—C13	121.4 (4)
C2A—C3—H3C	108.7	C11—C12—H12	119.3
C4—C3—H3D	108.7	C13—C12—H12	119.3
C2—C3—H3D	136.7	C14—C13—C12	119.6 (5)
C2A—C3—H3D	108.7	C14—C13—H13	120.2
H3C—C3—H3D	107.6	C12—C13—H13	120.2
C4—C3—H3A	109.0	C13—C14—C15	119.7 (5)
C2—C3—H3A	109.0	C13—C14—H14	120.1
C2A—C3—H3A	134.8	C15—C14—H14	120.1
H3C—C3—H3A	41.9	C14—C15—C16	120.2 (4)
H3D—C3—H3A	68.1	C14—C15—H15	119.9
C4—C3—H3B	109.3	C16—C15—H15	119.9
C2—C3—H3B	109.2	C11—C16—C15	120.4 (3)
C2A—C3—H3B	70.3	C11—C16—H16	119.8
H3C—C3—H3B	138.1	C15—C16—H16	119.8
H3D—C3—H3B	42.5	C16A—C11A—C12A	121.0 (17)
H3A—C3—H3B	107.8	C16A—C11A—C2A	117.1 (16)
O1—C2—C11	108.7 (2)	C12A—C11A—C2A	121.9 (17)
O1—C2—C3	110.33 (18)	C11A—C12A—C13A	118 (2)
C11—C2—C3	111.8 (2)	C11A—C12A—H12A	121.2
O1—C2—H2	108.6	C13A—C12A—H12A	121.2
C11—C2—H2	108.6	C14A—C13A—C12A	122 (2)
C3—C2—H2	108.6	C14A—C13A—H13A	119.0
O1—C2A—C11A	111.4 (9)	C12A—C13A—H13A	119.0
O1—C2A—C3	114.9 (7)	C15A—C14A—C13A	119 (2)
C11A—C2A—C3	109.9 (9)	C15A—C14A—H14A	120.6
O1—C2A—H3B	140.0	C13A—C14A—H14A	120.6
C11A—C2A—H3B	106.5	C14A—C15A—C16A	118.6 (16)
C3—C2A—H3B	36.8	C14A—C15A—H15A	120.7
O1—C2A—H2A	106.7	C16A—C15A—H15A	120.7
C11A—C2A—H2A	106.7	C11A—C16A—C15A	121.9 (14)
C3—C2A—H2A	106.7	C11A—C16A—H16A	119.0
H3B—C2A—H2A	73.0	C15A—C16A—H16A	119.0
O4—C4—C10	122.48 (16)	C18—O17—C6	115.85 (15)
O4—C4—C3	122.51 (18)	O18—C18—O17	122.98 (18)
C10—C4—C3	115.01 (16)	O18—C18—C19	125.9 (2)
C6—C5—C10	120.12 (18)	O17—C18—C19	111.08 (18)
C6—C5—H5	119.9	C18—C19—C20	113.28 (19)
C10—C5—H5	119.9	C18—C19—H19A	108.9
C5—C6—C7	120.98 (17)	C20—C19—H19A	108.9
C5—C6—O17	119.59 (17)	C18—C19—H19B	108.9
C7—C6—O17	119.39 (17)	C20—C19—H19B	108.9
C6—C7—C8	119.97 (19)	H19A—C19—H19B	107.7
C6—C7—H7	120.0	C19—C20—H20A	109.5
C8—C7—H7	120.0	C19—C20—H20B	109.5
C7—C8—C9	119.70 (18)	H20A—C20—H20B	109.5
C7—C8—H8	120.1	C19—C20—H20C	109.5
C9—C8—H8	120.1	H20A—C20—H20C	109.5
O1—C9—C8	117.62 (17)	H20B—C20—H20C	109.5
O1—C9—C10	122.15 (17)
C2A—O1—C2—C11	−68.7 (5)	C8—C9—C10—C4	−177.69 (18)
C9—O1—C2—C11	−177.9 (2)	O4—C4—C10—C5	−2.1 (3)
C2A—O1—C2—C3	54.2 (5)	C3—C4—C10—C5	178.64 (18)
C9—O1—C2—C3	−55.0 (2)	O4—C4—C10—C9	176.33 (19)
C4—C3—C2—O1	53.9 (3)	C3—C4—C10—C9	−2.9 (3)
C2A—C3—C2—O1	−47.5 (5)	O1—C2—C11—C12	53.9 (4)
C4—C3—C2—C11	175.0 (2)	C3—C2—C11—C12	−68.2 (4)
C2A—C3—C2—C11	73.6 (5)	O1—C2—C11—C16	−130.7 (3)
C9—O1—C2A—C11A	167.4 (8)	C3—C2—C11—C16	107.3 (3)
C2—O1—C2A—C11A	72.1 (9)	C16—C11—C12—C13	0.8 (5)
C9—O1—C2A—C3	41.6 (10)	C2—C11—C12—C13	176.3 (4)
C2—O1—C2A—C3	−53.7 (7)	C11—C12—C13—C14	−1.9 (7)
C4—C3—C2A—O1	−39.4 (10)	C12—C13—C14—C15	1.7 (8)
C2—C3—C2A—O1	57.7 (7)	C13—C14—C15—C16	−0.5 (7)
C4—C3—C2A—C11A	−165.9 (8)	C12—C11—C16—C15	0.4 (5)
C2—C3—C2A—C11A	−68.8 (9)	C2—C11—C16—C15	−175.2 (3)
C2—C3—C4—O4	155.4 (2)	C14—C15—C16—C11	−0.6 (5)
C2A—C3—C4—O4	−159.7 (5)	O1—C2A—C11A—C16A	−61.9 (18)
C2—C3—C4—C10	−25.4 (3)	C3—C2A—C11A—C16A	66.6 (17)
C2A—C3—C4—C10	19.6 (6)	O1—C2A—C11A—C12A	119.9 (17)
C10—C5—C6—C7	−1.0 (3)	C3—C2A—C11A—C12A	−111.6 (17)
C10—C5—C6—O17	−178.93 (17)	C16A—C11A—C12A—C13A	−5(3)
C5—C6—C7—C8	0.2 (3)	C2A—C11A—C12A—C13A	173.6 (17)
O17—C6—C7—C8	178.17 (18)	C11A—C12A—C13A—C14A	6(4)
C6—C7—C8—C9	1.0 (3)	C12A—C13A—C14A—C15A	−4(4)
C2A—O1—C9—C8	156.3 (7)	C13A—C14A—C15A—C16A	−1(3)
C2—O1—C9—C8	−152.26 (19)	C12A—C11A—C16A—C15A	0(3)
C2A—O1—C9—C10	−24.2 (7)	C2A—C11A—C16A—C15A	−177.7 (12)
C2—O1—C9—C10	27.2 (3)	C14A—C15A—C16A—C11A	2(3)
C7—C8—C9—O1	177.93 (18)	C5—C6—O17—C18	−74.2 (2)
C7—C8—C9—C10	−1.5 (3)	C7—C6—O17—C18	107.8 (2)
C6—C5—C10—C9	0.5 (3)	C6—O17—C18—O18	−5.5 (3)
C6—C5—C10—C4	178.93 (18)	C6—O17—C18—C19	173.63 (16)
O1—C9—C10—C5	−178.66 (17)	O18—C18—C19—C20	−1.8 (3)
C8—C9—C10—C5	0.8 (3)	O17—C18—C19—C20	179.05 (17)
O1—C9—C10—C4	2.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O18i	1.00	2.37	3.145 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O18i	1.00	2.37	3.145 (3)	133

Symmetry code: (i) .