1-(5,7-Dihy-droxy-2,2-dimethylchroman-6-yl)ethanone.

In the title mol-ecule, C(13)H(16)O(4), the pyran ring is in a half-chair conformation. There is an intra-molecular hydrogen bond involving the ketone O atom and an H atom of a phenol group which forms an S(6) ring. The ketone O atom is also involved in an inter-molecular hydrogen bond with a different phenolic H atom of a symmetry-related mol-ecule, forming C(6) chains along the c-axis direction.

Related literature

For applications of the title compound, see: Kraus et al. (2011 ▶); Basabe et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a related structure, see: Chakkaravarthi et al. (2007 ▶).

Experimental

Crystal data

C13H16O4

M = 236.26

Tetragonal,

a = 10.5677 (2) Å

c = 21.4244 (5) Å

V = 2392.6 (1) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.6 × 0.4 × 0.4 mm

Data collection

Oxford Diffraction Xcalibur 2 CCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.955, T max = 0.962

26011 measured reflections

2366 independent reflections

2046 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.091

S = 1.08

2366 reflections

166 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.11 e Å−3

Absolute structure: Flack (1983 ▶), 931 Friedel pairs

Flack parameter: 0.7 (11)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: WinGX (Farrugia, 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536811047982/lh5372sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047982/lh5372Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047982/lh5372Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536811047982/lh5372Isup4.cml

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

C13H16O4	Dx = 1.312 Mg m−3
Mr = 236.26	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41212	Cell parameters from 2366 reflections
Hall symbol: P 4abw 2nw	θ = 2.9–26.0°
a = 10.5677 (2) Å	µ = 0.10 mm−1
c = 21.4244 (5) Å	T = 298 K
V = 2392.6 (1) Å3	Needle, colourless
Z = 8	0.6 × 0.4 × 0.4 mm
F(000) = 1008

Oxford Diffraction Xcalibur 2 CCD diffractometer	2366 independent reflections
Radiation source: fine-focus sealed tube	2046 reflections with I > 2σ(I)
graphite	Rint = 0.047
Detector resolution: 8.4190 pixels mm-1	θmax = 26.0°, θmin = 2.9°
ω scans at fixed θ angles	h = −13→13
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −13→13
Tmin = 0.955, Tmax = 0.962	l = −26→26
26011 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.0612P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.091	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.12 e Å−3
2366 reflections	Δρmin = −0.11 e Å−3
166 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0094 (18)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 931 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.7 (11)

Experimental. 1H NMR (400 MHz, CD3OD) 1.31 (2x 3H, s, C(CH3)2), 1.78 (2H, t, J = 6.7 Hz, CH2), 2.55 (2H, t, J = 6.7 Hz, CH2), 2.62 (3H, s, COCH3), 5.77 (1H, s, ArH); 13C NMR 15.6 (C(CH3)2), 25.6 (2 × CH2), 31.3 (C(CH3)2), 31.8 (COCH3), 75.3 (C(CH3)2, 94.5 (C-5), 99.9 (C-1), 104.2 (C-3), 160.0, 160.9, 163.3 (C-2,4,6), 203.4 (COCH3); ESITOFMS, m/z 259.0945 [M+Na]+ (calc. for C13H16NaO4 259.0946); IR (KBr) υ 2961 2918 2872 1654 1611 1433 1159 cm-1.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
H102	1.1657 (18)	0.6538 (18)	0.1786 (9)	0.064 (5)*
H103	0.794 (2)	0.877 (2)	0.3250 (10)	0.075 (7)*
O1	0.94129 (10)	0.98280 (11)	0.09038 (5)	0.0540 (3)
O2	1.11831 (12)	0.66838 (11)	0.21655 (5)	0.0563 (3)
C9	0.93675 (14)	0.92341 (14)	0.14598 (6)	0.0410 (3)
O3	0.77624 (12)	0.92148 (12)	0.29235 (6)	0.0619 (3)
C7	1.03346 (13)	0.76254 (13)	0.20884 (7)	0.0390 (3)
O4	0.87361 (12)	0.75511 (12)	0.36008 (5)	0.0611 (4)
C8	1.02635 (13)	0.82754 (14)	0.15389 (7)	0.0403 (3)
H8	1.0815	0.8079	0.1215	0.048*
C4	0.85141 (14)	0.95417 (14)	0.19248 (7)	0.0452 (3)
C6	0.95010 (13)	0.79073 (13)	0.25928 (6)	0.0397 (3)
C12	0.95429 (15)	0.72843 (14)	0.31906 (7)	0.0468 (4)
C5	0.86024 (13)	0.88832 (13)	0.24823 (7)	0.0427 (3)
C1	0.83994 (17)	1.07167 (15)	0.07346 (8)	0.0553 (4)
C2	0.79788 (18)	1.14369 (17)	0.12997 (8)	0.0657 (5)
H2A	0.7282	1.1988	0.1186	0.079*
H2B	0.8670	1.1966	0.1444	0.079*
C3	0.75608 (18)	1.05776 (18)	0.18283 (9)	0.0670 (5)
H3A	0.7474	1.1067	0.2209	0.080*
H3B	0.6743	1.0211	0.1730	0.080*
C13	1.0503 (2)	0.6319 (2)	0.33569 (9)	0.0717 (6)
H13A	1.0384	0.6062	0.3783	0.108*
H13B	1.1334	0.6671	0.3308	0.108*
H13C	1.0412	0.5598	0.3088	0.108*
C10	0.9031 (2)	1.15856 (19)	0.02626 (9)	0.0774 (6)
H10A	0.9746	1.1991	0.0453	0.116*
H10B	0.8437	1.2216	0.0127	0.116*
H10C	0.9307	1.1098	−0.0090	0.116*
C11	0.7364 (2)	0.9942 (2)	0.04359 (11)	0.0801 (6)
H11A	0.7687	0.9537	0.0068	0.120*
H11B	0.6672	1.0485	0.0325	0.120*
H11C	0.7076	0.9311	0.0725	0.120*

	U11	U22	U33	U12	U13	U23
O1	0.0605 (7)	0.0550 (7)	0.0466 (6)	0.0166 (5)	−0.0064 (5)	0.0060 (5)
O2	0.0642 (7)	0.0578 (7)	0.0469 (6)	0.0220 (6)	0.0037 (5)	0.0064 (5)
C9	0.0420 (8)	0.0391 (8)	0.0418 (7)	0.0004 (6)	−0.0102 (6)	−0.0035 (6)
O3	0.0626 (7)	0.0610 (8)	0.0621 (8)	0.0078 (6)	0.0188 (7)	−0.0060 (6)
C7	0.0381 (7)	0.0363 (7)	0.0427 (7)	0.0005 (6)	−0.0055 (6)	−0.0035 (6)
O4	0.0725 (8)	0.0614 (7)	0.0495 (6)	−0.0088 (6)	0.0142 (6)	0.0021 (5)
C8	0.0384 (7)	0.0433 (8)	0.0393 (7)	0.0037 (6)	−0.0016 (5)	−0.0030 (6)
C4	0.0408 (8)	0.0400 (8)	0.0548 (8)	0.0043 (6)	−0.0045 (7)	−0.0072 (6)
C6	0.0425 (8)	0.0359 (7)	0.0406 (7)	−0.0070 (6)	−0.0024 (6)	−0.0052 (6)
C12	0.0533 (9)	0.0437 (8)	0.0433 (8)	−0.0129 (7)	−0.0015 (7)	−0.0023 (7)
C5	0.0388 (8)	0.0403 (7)	0.0492 (8)	−0.0038 (6)	0.0028 (6)	−0.0100 (6)
C1	0.0624 (10)	0.0412 (8)	0.0622 (10)	0.0110 (7)	−0.0207 (8)	0.0042 (7)
C2	0.0660 (11)	0.0489 (9)	0.0822 (12)	0.0191 (9)	−0.0169 (10)	−0.0018 (9)
C3	0.0609 (11)	0.0643 (11)	0.0758 (12)	0.0237 (9)	−0.0025 (9)	−0.0044 (9)
C13	0.0795 (13)	0.0825 (14)	0.0532 (10)	0.0105 (10)	0.0037 (9)	0.0208 (9)
C10	0.0952 (15)	0.0560 (11)	0.0811 (13)	0.0109 (11)	−0.0145 (11)	0.0178 (10)
C11	0.0806 (14)	0.0621 (11)	0.0975 (15)	0.0070 (11)	−0.0408 (12)	−0.0017 (11)

O1—C9	1.3471 (18)	C1—C2	1.497 (2)
O1—C1	1.4699 (18)	C1—C11	1.509 (3)
O2—C7	1.3496 (17)	C1—C10	1.520 (3)
O2—H102	0.97 (2)	C2—C3	1.517 (3)
C9—C4	1.383 (2)	C2—H2A	0.9700
C9—C8	1.397 (2)	C2—H2B	0.9700
O3—C5	1.3432 (18)	C3—H3A	0.9700
O3—H103	0.86 (2)	C3—H3B	0.9700
C7—C8	1.365 (2)	C13—H13A	0.9600
C7—C6	1.426 (2)	C13—H13B	0.9600
O4—C12	1.2566 (19)	C13—H13C	0.9600
C8—H8	0.9300	C10—H10A	0.9600
C4—C5	1.386 (2)	C10—H10B	0.9600
C4—C3	1.502 (2)	C10—H10C	0.9600
C6—C5	1.422 (2)	C11—H11A	0.9600
C6—C12	1.441 (2)	C11—H11B	0.9600
C12—C13	1.482 (2)	C11—H11C	0.9600
C9—O1—C1	119.33 (12)	C1—C2—C3	112.68 (15)
C7—O2—H102	111.0 (11)	C1—C2—H2A	109.1
O1—C9—C4	123.42 (14)	C3—C2—H2A	109.1
O1—C9—C8	114.90 (12)	C1—C2—H2B	109.1
C4—C9—C8	121.68 (13)	C3—C2—H2B	109.1
C5—O3—H103	106.8 (14)	H2A—C2—H2B	107.8
O2—C7—C8	120.88 (13)	C4—C3—C2	110.10 (15)
O2—C7—C6	118.15 (13)	C4—C3—H3A	109.6
C8—C7—C6	120.97 (13)	C2—C3—H3A	109.6
C7—C8—C9	120.46 (13)	C4—C3—H3B	109.6
C7—C8—H8	119.8	C2—C3—H3B	109.6
C9—C8—H8	119.8	H3A—C3—H3B	108.2
C9—C4—C5	117.34 (13)	C12—C13—H13A	109.5
C9—C4—C3	120.64 (15)	C12—C13—H13B	109.5
C5—C4—C3	121.99 (14)	H13A—C13—H13B	109.5
C5—C6—C7	115.98 (13)	C12—C13—H13C	109.5
C5—C6—C12	120.00 (13)	H13A—C13—H13C	109.5
C7—C6—C12	124.01 (13)	H13B—C13—H13C	109.5
O4—C12—C6	119.89 (15)	C1—C10—H10A	109.5
O4—C12—C13	116.79 (14)	C1—C10—H10B	109.5
C6—C12—C13	123.32 (14)	H10A—C10—H10B	109.5
O3—C5—C4	115.54 (14)	C1—C10—H10C	109.5
O3—C5—C6	120.90 (14)	H10A—C10—H10C	109.5
C4—C5—C6	123.56 (13)	H10B—C10—H10C	109.5
O1—C1—C2	109.98 (12)	C1—C11—H11A	109.5
O1—C1—C11	106.62 (13)	C1—C11—H11B	109.5
C2—C1—C11	113.80 (18)	H11A—C11—H11B	109.5
O1—C1—C10	103.32 (15)	C1—C11—H11C	109.5
C2—C1—C10	111.17 (15)	H11A—C11—H11C	109.5
C11—C1—C10	111.33 (16)	H11B—C11—H11C	109.5
C1—O1—C9—C4	−9.6 (2)	C9—C4—C5—O3	179.59 (12)
C1—O1—C9—C8	170.94 (13)	C3—C4—C5—O3	1.4 (2)
O2—C7—C8—C9	178.90 (13)	C9—C4—C5—C6	−1.1 (2)
C6—C7—C8—C9	0.0 (2)	C3—C4—C5—C6	−179.29 (14)
O1—C9—C8—C7	178.31 (12)	C7—C6—C5—O3	179.24 (13)
C4—C9—C8—C7	−1.2 (2)	C12—C6—C5—O3	−1.8 (2)
O1—C9—C4—C5	−177.76 (13)	C7—C6—C5—C4	0.0 (2)
C8—C9—C4—C5	1.7 (2)	C12—C6—C5—C4	178.93 (13)
O1—C9—C4—C3	0.5 (2)	C9—O1—C1—C2	36.82 (19)
C8—C9—C4—C3	179.93 (15)	C9—O1—C1—C11	−87.00 (18)
O2—C7—C6—C5	−178.34 (12)	C9—O1—C1—C10	155.56 (14)
C8—C7—C6—C5	0.6 (2)	O1—C1—C2—C3	−55.9 (2)
O2—C7—C6—C12	2.7 (2)	C11—C1—C2—C3	63.6 (2)
C8—C7—C6—C12	−178.32 (13)	C10—C1—C2—C3	−169.70 (14)
C5—C6—C12—O4	4.3 (2)	C9—C4—C3—C2	−19.4 (2)
C7—C6—C12—O4	−176.84 (14)	C5—C4—C3—C2	158.76 (15)
C5—C6—C12—C13	−175.88 (16)	C1—C2—C3—C4	47.0 (2)
C7—C6—C12—C13	3.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H102···O4i	0.97 (2)	1.77 (2)	2.737 (2)	179 (1)
O3—H103···O4	0.86 (2)	1.71 (2)	2.501 (2)	151 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H102⋯O4i	0.97 (2)	1.77 (2)	2.737 (2)	179 (1)
O3—H103⋯O4	0.86 (2)	1.71 (2)	2.501 (2)	151 (2)

Symmetry code: (i) .