5-Hydr­oxy-7-meth­oxy-2,6,8-trimethyl-4H-chromen-4-one

The title compound, C₁₃H₁₄O₄, known as 8-methyl­eugenitin, is a chromone isolated from the leaves of Mellaleuca cajuputi Powell. The chromone unit is essentially planar. The methyl and hydroxyl groups lie in the plane of the benzene ring while the meth­oxy substituent is perpendicular to it. An intra­molecular O—H...O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by intra­molecular O—H...O and weak C—H...O hydrogen bonds, together with C—H...π and π–π inter­actions. Mol­ecules are arranged in an anti­parallel fashion into columns along the [100] direction.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.038
• wR factor = 0.111
• Data-to-parameter ratio = 20.4

checkCIF/PLATON results

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   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

5-Hydroxy-7-methoxy-2,6,8-trimethyl-4H-chromen-4-one

Crystal data

C13H14O4	F(000) = 496
Mr = 234.24	Dx = 1.404 Mg m^−3
Monoclinic, P21/c	Melting point = 387–388 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.0816 (2) Å	Cell parameters from 3216 reflections
b = 8.6719 (2) Å	θ = 2.5–30.0°
c = 15.8187 (4) Å	µ = 0.10 mm^−1
β = 91.301 (1)°	T = 100 K
V = 1108.33 (5) Å^3	Block, yellow
Z = 4	0.58 × 0.45 × 0.36 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3216 independent reflections
Radiation source: fine-focus sealed tube	2884 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 2.5°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
Tmin = 0.942, Tmax = 0.964	l = −22→22
11518 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0625P)^2 + 0.3003P] where P = (Fo^2 + 2Fc^2)/3
3216 reflections	(Δ/σ)max = 0.001
158 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.45444 (8)	0.98891 (8)	−0.18460 (4)	0.01713 (15)
O2	0.12897 (8)	1.24365 (7)	0.01685 (4)	0.01417 (14)
O3	0.12841 (9)	0.86712 (8)	0.17293 (4)	0.02054 (16)
O4	0.29691 (9)	0.71736 (8)	0.06228 (4)	0.01978 (16)
H4A	0.2470	0.7328	0.1060	0.030*
C1	0.05830 (11)	1.24958 (10)	0.09393 (5)	0.01449 (17)
C2	0.05932 (11)	1.12901 (10)	0.14796 (5)	0.01617 (17)
H2A	0.0121	1.1402	0.2007	0.019*
C3	0.13212 (11)	0.98330 (10)	0.12561 (5)	0.01518 (17)
C4	0.21122 (10)	0.97993 (10)	0.04387 (5)	0.01320 (16)
C5	0.29497 (11)	0.84741 (10)	0.01466 (5)	0.01445 (17)
C6	0.37587 (10)	0.84872 (10)	−0.06211 (5)	0.01468 (17)
C7	0.36988 (10)	0.98535 (10)	−0.10962 (5)	0.01350 (17)
C8	0.28655 (10)	1.11859 (9)	−0.08511 (5)	0.01328 (16)
C9	0.20920 (10)	1.11126 (9)	−0.00746 (5)	0.01253 (16)
C10	−0.01879 (12)	1.40291 (10)	0.10875 (6)	0.01838 (18)
H10A	−0.0603	1.4068	0.1651	0.028*
H10B	−0.1083	1.4184	0.0687	0.028*
H10C	0.0625	1.4824	0.1020	0.028*
C11	0.28008 (12)	1.26296 (10)	−0.13767 (6)	0.01793 (18)
H11A	0.3197	1.3485	−0.1044	0.027*
H11C	0.1680	1.2821	−0.1561	0.027*
H11D	0.3484	1.2505	−0.1860	0.027*
C12	0.35243 (13)	0.94221 (12)	−0.25522 (6)	0.0231 (2)
H12A	0.4152	0.9474	−0.3060	0.035*
H12D	0.2585	1.0096	−0.2603	0.035*
H12B	0.3153	0.8383	−0.2468	0.035*
C13	0.46790 (12)	0.70899 (11)	−0.09241 (6)	0.01997 (19)
H13A	0.5043	0.6486	−0.0447	0.030*
H13B	0.5621	0.7413	−0.1238	0.030*
H13C	0.3959	0.6480	−0.1281	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0155 (3)	0.0208 (3)	0.0153 (3)	−0.0022 (2)	0.0038 (2)	−0.0039 (2)
O2	0.0158 (3)	0.0137 (3)	0.0132 (3)	0.0020 (2)	0.0022 (2)	−0.0009 (2)
O3	0.0229 (3)	0.0213 (3)	0.0175 (3)	0.0005 (3)	0.0017 (2)	0.0070 (2)
O4	0.0249 (3)	0.0150 (3)	0.0194 (3)	0.0023 (2)	0.0001 (2)	0.0044 (2)
C1	0.0126 (4)	0.0176 (4)	0.0133 (4)	−0.0007 (3)	0.0006 (3)	−0.0030 (3)
C2	0.0150 (4)	0.0205 (4)	0.0130 (4)	−0.0004 (3)	0.0013 (3)	−0.0005 (3)
C3	0.0134 (4)	0.0183 (4)	0.0137 (4)	−0.0013 (3)	−0.0014 (3)	0.0017 (3)
C4	0.0129 (4)	0.0142 (4)	0.0125 (3)	−0.0003 (3)	−0.0010 (3)	0.0004 (3)
C5	0.0144 (4)	0.0127 (3)	0.0161 (4)	−0.0003 (3)	−0.0031 (3)	0.0009 (3)
C6	0.0133 (4)	0.0138 (4)	0.0169 (4)	0.0006 (3)	−0.0013 (3)	−0.0023 (3)
C7	0.0116 (4)	0.0155 (4)	0.0133 (4)	−0.0014 (3)	0.0001 (3)	−0.0023 (3)
C8	0.0130 (4)	0.0138 (4)	0.0131 (3)	−0.0007 (3)	0.0001 (3)	−0.0002 (3)
C9	0.0117 (3)	0.0124 (3)	0.0135 (4)	0.0006 (3)	−0.0008 (3)	−0.0010 (3)
C10	0.0200 (4)	0.0171 (4)	0.0182 (4)	0.0026 (3)	0.0026 (3)	−0.0031 (3)
C11	0.0220 (4)	0.0155 (4)	0.0164 (4)	0.0001 (3)	0.0036 (3)	0.0024 (3)
C12	0.0252 (5)	0.0299 (5)	0.0145 (4)	−0.0069 (4)	0.0027 (3)	−0.0051 (3)
C13	0.0189 (4)	0.0157 (4)	0.0253 (4)	0.0027 (3)	0.0005 (3)	−0.0038 (3)

Geometric parameters (Å, º)

O1—C7	1.3824 (10)	C6—C13	1.5058 (12)
O1—C12	1.4318 (11)	C7—C8	1.3967 (11)
O2—C1	1.3591 (10)	C8—C9	1.3923 (11)
O2—C9	1.3775 (10)	C8—C11	1.5031 (12)
O3—C3	1.2558 (10)	C10—H10A	0.9600
O4—C5	1.3562 (10)	C10—H10B	0.9600
O4—H4A	0.8200	C10—H10C	0.9600
C1—C2	1.3504 (12)	C11—H11A	0.9600
C1—C10	1.4892 (12)	C11—H11C	0.9600
C2—C3	1.4412 (12)	C11—H11D	0.9600
C2—H2A	0.9300	C12—H12A	0.9600
C3—C4	1.4557 (11)	C12—H12D	0.9600
C4—C9	1.3986 (11)	C12—H12B	0.9600
C4—C5	1.4165 (11)	C13—H13A	0.9600
C5—C6	1.3922 (12)	C13—H13B	0.9600
C6—C7	1.4035 (12)	C13—H13C	0.9600
C7—O1—C12	112.09 (7)	O2—C9—C8	115.59 (7)
C1—O2—C9	119.48 (7)	O2—C9—C4	121.06 (7)
C5—O4—H4A	109.5	C8—C9—C4	123.35 (7)
C2—C1—O2	122.81 (8)	C1—C10—H10A	109.5
C2—C1—C10	126.03 (8)	C1—C10—H10B	109.5
O2—C1—C10	111.15 (7)	H10A—C10—H10B	109.5
C1—C2—C3	121.35 (8)	C1—C10—H10C	109.5
C1—C2—H2A	119.3	H10A—C10—H10C	109.5
C3—C2—H2A	119.3	H10B—C10—H10C	109.5
O3—C3—C2	122.81 (8)	C8—C11—H11A	109.5
O3—C3—C4	122.02 (8)	C8—C11—H11C	109.5
C2—C3—C4	115.18 (7)	H11A—C11—H11C	109.5
C9—C4—C5	118.07 (8)	C8—C11—H11D	109.5
C9—C4—C3	119.99 (7)	H11A—C11—H11D	109.5
C5—C4—C3	121.92 (7)	H11C—C11—H11D	109.5
O4—C5—C6	119.44 (8)	O1—C12—H12A	109.5
O4—C5—C4	119.54 (8)	O1—C12—H12D	109.5
C6—C5—C4	121.02 (8)	H12A—C12—H12D	109.5
C5—C6—C7	117.57 (7)	O1—C12—H12B	109.5
C5—C6—C13	121.08 (8)	H12A—C12—H12B	109.5
C7—C6—C13	121.34 (8)	H12D—C12—H12B	109.5
O1—C7—C8	118.07 (7)	C6—C13—H13A	109.5
O1—C7—C6	117.81 (7)	C6—C13—H13B	109.5
C8—C7—C6	124.11 (8)	H13A—C13—H13B	109.5
C9—C8—C7	115.86 (7)	C6—C13—H13C	109.5
C9—C8—C11	121.02 (7)	H13A—C13—H13C	109.5
C7—C8—C11	123.12 (7)	H13B—C13—H13C	109.5
C9—O2—C1—C2	−1.67 (12)	C12—O1—C7—C6	91.12 (9)
C9—O2—C1—C10	178.85 (7)	C5—C6—C7—O1	177.97 (7)
O2—C1—C2—C3	−1.94 (14)	C13—C6—C7—O1	−1.37 (12)
C10—C1—C2—C3	177.46 (8)	C5—C6—C7—C8	−0.77 (13)
C1—C2—C3—O3	−176.72 (8)	C13—C6—C7—C8	179.88 (8)
C1—C2—C3—C4	3.40 (12)	O1—C7—C8—C9	−177.38 (7)
O3—C3—C4—C9	178.64 (8)	C6—C7—C8—C9	1.36 (13)
C2—C3—C4—C9	−1.48 (12)	O1—C7—C8—C11	2.08 (12)
O3—C3—C4—C5	−2.87 (13)	C6—C7—C8—C11	−179.19 (8)
C2—C3—C4—C5	177.01 (8)	C1—O2—C9—C8	−176.23 (7)
C9—C4—C5—O4	−178.92 (7)	C1—O2—C9—C4	3.60 (12)
C3—C4—C5—O4	2.57 (13)	C7—C8—C9—O2	179.22 (7)
C9—C4—C5—C6	1.29 (13)	C11—C8—C9—O2	−0.25 (12)
C3—C4—C5—C6	−177.22 (8)	C7—C8—C9—C4	−0.60 (12)
O4—C5—C6—C7	179.60 (8)	C11—C8—C9—C4	179.93 (8)
C4—C5—C6—C7	−0.61 (12)	C5—C4—C9—O2	179.52 (7)
O4—C5—C6—C13	−1.05 (12)	C3—C4—C9—O2	−1.94 (12)
C4—C5—C6—C13	178.74 (8)	C5—C4—C9—C8	−0.67 (13)
C12—O1—C7—C8	−90.07 (9)	C3—C4—C9—C8	177.88 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3	0.82	1.86	2.5909 (10)	149
C13—H13B···Cg1^i	0.96	2.87	3.5729 (10)	131

Symmetry code: (i) −x+1, −y+2, −z.