5-Hydr­oxy-7-meth­oxy-2-(4-methoxy­phen­yl)-4H-1-benzopyran-4-one

The title compound, C₁₇H₁₄O₅, a flavone, was isolated from the rhizomes of Kaempferia parviflora. The benzopyran-4-one ring system and the methoxy­phenyl substituent are approximately coplanar. The mol­ecules are linked via inter­molecular C—H...O hydrogen bonds to form chains.

Key indicators

• Single-crystal X-ray study
• T = 273 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.046
• wR factor = 0.128
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

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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-(4-methoxyphenyl)-4H-1-benzopyran-4-one

Crystal data

C17H14O5	F(000) = 624
Mr = 298.28	Dx = 1.449 Mg m^−3
Monoclinic, P21/c	Melting point = 447–448 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.9406 (4) Å	Cell parameters from 3581 reflections
b = 3.8619 (1) Å	θ = 2.0–28.0°
c = 21.7968 (4) Å	µ = 0.11 mm^−1
β = 106.52 (1)°	T = 273 K
V = 1367.15 (9) Å^3	Plate, colourless
Z = 4	0.54 × 0.15 × 0.08 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3283 independent reflections
Radiation source: fine-focus sealed tube	2207 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
Detector resolution: 8.33 pixels mm^-1	θmax = 28.0°, θmin = 2.0°
ω scans	h = −21→22
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→5
Tmin = 0.912, Tmax = 0.992	l = −28→28
17884 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0571P)^2 + 0.2601P] where P = (Fo^2 + 2Fc^2)/3
3283 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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	0.15499 (6)	0.9753 (3)	0.37516 (4)	0.0409 (3)
O2	0.25586 (7)	0.5256 (3)	0.54929 (5)	0.0541 (4)
O3	0.39800 (7)	0.5554 (4)	0.52901 (5)	0.0560 (4)
H3	0.3636	0.5130	0.5479	0.084*
O4	0.40678 (7)	1.0285 (3)	0.32828 (5)	0.0538 (4)
O5	−0.22834 (7)	1.0817 (4)	0.28553 (5)	0.0533 (4)
C1	0.23874 (9)	0.9148 (4)	0.39514 (7)	0.0362 (4)
C2	0.28282 (10)	1.0058 (4)	0.35373 (7)	0.0412 (4)
H2	0.2573	1.1094	0.3146	0.049*
C3	0.36683 (10)	0.9380 (5)	0.37218 (7)	0.0414 (4)
C4	0.40646 (10)	0.7874 (5)	0.43095 (7)	0.0440 (4)
H4	0.4628	0.7452	0.4424	0.053*
C5	0.36052 (10)	0.7022 (5)	0.47179 (7)	0.0412 (4)
C6	0.27504 (9)	0.7617 (4)	0.45482 (6)	0.0362 (4)
C7	0.22512 (10)	0.6656 (4)	0.49571 (7)	0.0397 (4)
C8	0.13922 (10)	0.7345 (5)	0.47088 (7)	0.0411 (4)
H8	0.1045	0.6780	0.4956	0.049*
C9	0.10645 (9)	0.8792 (4)	0.41260 (6)	0.0362 (4)
C10	0.01916 (10)	0.9446 (4)	0.38162 (6)	0.0355 (4)
C11	−0.04119 (10)	0.8394 (5)	0.40996 (7)	0.0424 (4)
H11	−0.0249	0.7380	0.4503	0.051*
C12	−0.12400 (10)	0.8807 (5)	0.38018 (7)	0.0424 (4)
H12	−0.1628	0.8085	0.4002	0.051*
C13	−0.14880 (10)	1.0311 (4)	0.31993 (7)	0.0399 (4)
C14	−0.08988 (10)	1.1419 (5)	0.29100 (7)	0.0444 (4)
H14	−0.1064	1.2448	0.2508	0.053*
C15	−0.00750 (10)	1.1007 (5)	0.32127 (7)	0.0411 (4)
H15	0.0311	1.1775	0.3014	0.049*
C16	0.49030 (11)	0.9268 (6)	0.33992 (9)	0.0601 (5)
H16A	0.5094	0.9900	0.3040	0.090*
H16B	0.4947	0.6806	0.3460	0.090*
H16C	0.5233	1.0410	0.3777	0.090*
C17	−0.29207 (11)	0.9581 (6)	0.31075 (9)	0.0553 (5)
H17A	−0.3447	1.0069	0.2810	0.083*
H17B	−0.2882	1.0716	0.3507	0.083*
H17C	−0.2862	0.7127	0.3175	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0397 (6)	0.0506 (7)	0.0330 (5)	0.0022 (5)	0.0113 (4)	0.0064 (5)
O2	0.0556 (7)	0.0711 (9)	0.0343 (5)	0.0069 (7)	0.0107 (5)	0.0164 (6)
O3	0.0481 (7)	0.0774 (10)	0.0384 (6)	0.0072 (7)	0.0054 (5)	0.0148 (6)
O4	0.0448 (7)	0.0732 (10)	0.0467 (6)	0.0002 (7)	0.0183 (5)	0.0100 (6)
O5	0.0428 (6)	0.0721 (9)	0.0436 (6)	0.0051 (7)	0.0102 (5)	0.0118 (6)
C1	0.0377 (8)	0.0370 (9)	0.0324 (7)	−0.0006 (7)	0.0075 (6)	−0.0016 (6)
C2	0.0455 (9)	0.0460 (11)	0.0310 (7)	−0.0009 (8)	0.0093 (6)	0.0042 (7)
C3	0.0440 (9)	0.0453 (11)	0.0363 (7)	−0.0039 (8)	0.0136 (6)	−0.0008 (7)
C4	0.0385 (8)	0.0506 (11)	0.0408 (8)	−0.0007 (8)	0.0079 (6)	−0.0003 (8)
C5	0.0453 (9)	0.0430 (10)	0.0323 (7)	0.0006 (8)	0.0060 (6)	0.0003 (7)
C6	0.0425 (8)	0.0351 (9)	0.0295 (6)	0.0002 (8)	0.0078 (6)	−0.0008 (6)
C7	0.0499 (9)	0.0383 (10)	0.0304 (7)	0.0008 (8)	0.0106 (6)	0.0004 (7)
C8	0.0458 (9)	0.0459 (10)	0.0337 (7)	0.0021 (8)	0.0150 (6)	0.0028 (7)
C9	0.0446 (9)	0.0345 (9)	0.0319 (7)	−0.0008 (8)	0.0149 (6)	−0.0026 (6)
C10	0.0432 (8)	0.0323 (9)	0.0320 (7)	0.0016 (7)	0.0125 (6)	−0.0007 (6)
C11	0.0475 (9)	0.0475 (11)	0.0328 (7)	0.0007 (9)	0.0125 (6)	0.0071 (7)
C12	0.0459 (9)	0.0463 (11)	0.0379 (7)	−0.0017 (8)	0.0165 (7)	0.0036 (7)
C13	0.0423 (9)	0.0410 (10)	0.0359 (7)	0.0044 (8)	0.0102 (6)	−0.0007 (7)
C14	0.0504 (10)	0.0499 (11)	0.0341 (7)	0.0062 (9)	0.0140 (7)	0.0075 (7)
C15	0.0473 (9)	0.0438 (10)	0.0361 (7)	0.0027 (8)	0.0183 (7)	0.0053 (7)
C16	0.0520 (11)	0.0720 (14)	0.0629 (11)	0.0021 (11)	0.0269 (9)	0.0062 (10)
C17	0.0429 (9)	0.0675 (14)	0.0551 (10)	−0.0014 (10)	0.0131 (8)	0.0029 (10)

Geometric parameters (Å, º)

O1—C9	1.3645 (17)	C8—C9	1.354 (2)
O1—C1	1.3804 (18)	C8—H8	0.93
O2—C7	1.2578 (17)	C9—C10	1.462 (2)
O3—C5	1.3526 (18)	C10—C11	1.397 (2)
O3—H3	0.82	C10—C15	1.400 (2)
O4—C3	1.3652 (19)	C11—C12	1.377 (2)
O4—C16	1.420 (2)	C11—H11	0.93
O5—C13	1.3570 (18)	C12—C13	1.387 (2)
O5—C17	1.426 (2)	C12—H12	0.93
C1—C2	1.371 (2)	C13—C14	1.391 (2)
C1—C6	1.402 (2)	C14—C15	1.373 (2)
C2—C3	1.389 (2)	C14—H14	0.93
C2—H2	0.93	C15—H15	0.93
C3—C4	1.393 (2)	C16—H16A	0.96
C4—C5	1.379 (2)	C16—H16B	0.96
C4—H4	0.93	C16—H16C	0.96
C5—C6	1.408 (2)	C17—H17A	0.96
C6—C7	1.441 (2)	C17—H17B	0.96
C7—C8	1.426 (2)	C17—H17C	0.96
C9—O1—C1	120.35 (11)	C11—C10—C15	117.37 (15)
C5—O3—H3	109.5	C11—C10—C9	121.11 (13)
C3—O4—C16	118.12 (14)	C15—C10—C9	121.46 (14)
C13—O5—C17	118.72 (13)	C12—C11—C10	122.24 (14)
C2—C1—O1	116.89 (13)	C12—C11—H11	118.9
C2—C1—C6	122.80 (14)	C10—C11—H11	118.9
O1—C1—C6	120.31 (13)	C11—C12—C13	119.23 (14)
C1—C2—C3	117.78 (14)	C11—C12—H12	120.4
C1—C2—H2	121.1	C13—C12—H12	120.4
C3—C2—H2	121.1	O5—C13—C12	124.69 (14)
O4—C3—C2	114.83 (14)	O5—C13—C14	115.66 (13)
O4—C3—C4	123.09 (15)	C12—C13—C14	119.65 (15)
C2—C3—C4	122.08 (14)	C15—C14—C13	120.59 (14)
C5—C4—C3	118.71 (15)	C15—C14—H14	119.7
C5—C4—H4	120.6	C13—C14—H14	119.7
C3—C4—H4	120.6	C14—C15—C10	120.92 (14)
O3—C5—C4	119.48 (14)	C14—C15—H15	119.5
O3—C5—C6	119.26 (14)	C10—C15—H15	119.5
C4—C5—C6	121.25 (14)	O4—C16—H16A	109.5
C1—C6—C5	117.37 (14)	O4—C16—H16B	109.5
C1—C6—C7	120.18 (14)	H16A—C16—H16B	109.5
C5—C6—C7	122.44 (13)	O4—C16—H16C	109.5
O2—C7—C8	122.75 (14)	H16A—C16—H16C	109.5
O2—C7—C6	121.62 (15)	H16B—C16—H16C	109.5
C8—C7—C6	115.63 (13)	O5—C17—H17A	109.5
C9—C8—C7	122.34 (14)	O5—C17—H17B	109.5
C9—C8—H8	118.8	H17A—C17—H17B	109.5
C7—C8—H8	118.8	O5—C17—H17C	109.5
C8—C9—O1	121.16 (14)	H17A—C17—H17C	109.5
C8—C9—C10	126.55 (14)	H17B—C17—H17C	109.5
O1—C9—C10	112.28 (12)
C9—O1—C1—C2	177.38 (14)	C5—C6—C7—C8	−178.31 (15)
C9—O1—C1—C6	−1.6 (2)	O2—C7—C8—C9	−178.69 (16)
O1—C1—C2—C3	−178.23 (14)	C6—C7—C8—C9	0.3 (2)
C6—C1—C2—C3	0.7 (3)	C7—C8—C9—O1	−1.7 (3)
C16—O4—C3—C2	−171.93 (16)	C7—C8—C9—C10	176.83 (16)
C16—O4—C3—C4	7.7 (3)	C1—O1—C9—C8	2.4 (2)
C1—C2—C3—O4	178.75 (15)	C1—O1—C9—C10	−176.37 (13)
C1—C2—C3—C4	−0.9 (3)	C8—C9—C10—C11	−3.7 (3)
O4—C3—C4—C5	−179.36 (16)	O1—C9—C10—C11	174.93 (14)
C2—C3—C4—C5	0.3 (3)	C8—C9—C10—C15	179.17 (16)
C3—C4—C5—O3	179.93 (16)	O1—C9—C10—C15	−2.2 (2)
C3—C4—C5—C6	0.6 (3)	C15—C10—C11—C12	0.9 (3)
C2—C1—C6—C5	0.1 (2)	C9—C10—C11—C12	−176.32 (15)
O1—C1—C6—C5	179.00 (14)	C10—C11—C12—C13	0.1 (3)
C2—C1—C6—C7	−178.76 (16)	C17—O5—C13—C12	−3.3 (3)
O1—C1—C6—C7	0.1 (2)	C17—O5—C13—C14	176.77 (16)
O3—C5—C6—C1	179.90 (15)	C11—C12—C13—O5	179.16 (16)
C4—C5—C6—C1	−0.8 (3)	C11—C12—C13—C14	−0.9 (3)
O3—C5—C6—C7	−1.3 (3)	O5—C13—C14—C15	−179.42 (15)
C4—C5—C6—C7	178.07 (15)	C12—C13—C14—C15	0.6 (3)
C1—C6—C7—O2	179.49 (15)	C13—C14—C15—C10	0.4 (3)
C5—C6—C7—O2	0.7 (3)	C11—C10—C15—C14	−1.1 (2)
C1—C6—C7—C8	0.5 (2)	C9—C10—C15—C14	176.05 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.83	2.571 (2)	149
C4—H4···O3^i	0.93	2.54	3.441 (2)	163
C12—H12···O2^ii	0.93	2.52	3.430 (2)	167

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