8-Hydr-oxy-5,6,7-trimeth-oxy-2-phenyl-4H-chromen-4-one.

In the title compound, C(18)H(16)O(6), the benzopyran group is essentially planar, with the O atoms of the substituent groups lying close to its mean plane. The mol-ecular conformation is governed by intra-molecular inter-actions. The crystal packing is mainly determined by one classical inter-molecular hydrogen bond which gives rise to the formation of an infinite chain along the a axis.

Related literature

For related literature, see: Chebib & Johnston (2000 ▶); Medina et al. (1998 ▶).

Experimental

Crystal data

C18H16O6

M = 328.32

Triclinic,

a = 8.4536 (2) Å

b = 9.0878 (2) Å

c = 10.7832 (3) Å

α = 79.545 (2)°

β = 71.5640 (10)°

γ = 86.925 (2)°

V = 772.85 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 294 K

0.22 × 0.19 × 0.11 mm

Data collection

Nonius Kappa CCD diffractometer

Absorption correction: none

20499 measured reflections

3153 independent reflections

2512 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.123

S = 1.07

3153 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: COLLECT; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010696/bg2176sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010696/bg2176Isup2.hkl

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

C18H16O6	Z = 2
Mr = 328.32	F000 = 344
Triclinic, P1	Dx = 1.411 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.4536 (2) Å	Cell parameters from 20513 reflections
b = 9.0878 (2) Å	θ = 2.9–26.4º
c = 10.7832 (3) Å	µ = 0.11 mm−1
α = 79.545 (2)º	T = 294 K
β = 71.5640 (10)º	Prism, yellow
γ = 86.925 (2)º	0.22 × 0.19 × 0.11 mm
V = 772.85 (3) Å3

KappaCCD diffractometer	Rint = 0.049
φ scans and ω scans winth κ offsets	θmax = 26.4º
Absorption correction: none	θmin = 3.3º
20499 measured reflections	h = −10→10
3153 independent reflections	k = −11→11
2512 reflections with I > 2σ(I)	l = −13→13

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1467P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.042	(Δ/σ)max < 0.001
wR(F2) = 0.124	Δρmax = 0.25 e Å−3
S = 1.07	Δρmin = −0.24 e Å−3
3153 reflections	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
218 parameters	Extinction coefficient: 0.043 (11)

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.

	x	y	z	Uiso*/Ueq
O1	0.40508 (11)	0.55938 (11)	0.19334 (9)	0.0343 (3)
O2	0.05483 (13)	0.68927 (14)	0.00920 (12)	0.0550 (3)
O3	0.29650 (12)	0.85689 (12)	−0.19401 (10)	0.0428 (3)
O4	0.63074 (13)	0.94104 (12)	−0.28518 (10)	0.0441 (3)
O5	0.83892 (11)	0.83118 (11)	−0.14212 (9)	0.0362 (3)
O6	0.71943 (11)	0.63816 (12)	0.09768 (9)	0.0395 (3)
C1	0.16504 (16)	0.64776 (16)	0.06016 (15)	0.0350 (3)
C2	0.13054 (16)	0.54641 (16)	0.18467 (14)	0.0368 (3)
C3	0.24520 (16)	0.50867 (15)	0.24709 (13)	0.0330 (3)
C4	0.45089 (16)	0.65179 (15)	0.07187 (13)	0.0 (3)
C5	0.33896 (15)	0.70155 (15)	0.00135 (13)	0.0301 (3)
C6	0.39952 (16)	0.80083 (15)	−0.12037 (13)	0.0320 (3)
C7	0.56421 (16)	0.84828 (15)	−0.16628 (13)	0.0313 (3)
C8	0.67300 (15)	0.79300 (15)	−0.09404 (13)	0.0296 (3)
C9	0.61900 (15)	0.69429 (15)	0.02441 (13)	0.0295 (3)
C10	0.21737 (17)	0.41557 (16)	0.37915 (13)	0.0353 (3)
C11	0.30333 (19)	0.44556 (19)	0.46281 (16)	0.0459 (4)
C12	0.2755 (2)	0.3598 (2)	0.58706 (16)	0.0547 (5)
C13	0.1650 (2)	0.2423 (2)	0.62864 (17)	0.0552 (5)
C14	0.0795 (2)	0.2109 (2)	0.54662 (17)	0.0573 (5)
C15	0.1043 (2)	0.29793 (19)	0.42257 (16)	0.0469 (4)
C16	0.2848 (3)	0.7646 (3)	−0.2840 (2)	0.0738 (6)
C17	0.5601 (3)	1.0840 (2)	−0.3033 (2)	0.0708 (6)
C18	0.8774 (2)	0.96476 (19)	−0.10671 (19)	0.0514 (4)
H8	0.8139	0.672	0.0606	0.059*
H8A	0.0242	0.5052	0.2237	0.044*
H17	0.3799	0.5239	0.4346	0.055*
H18	0.3319	0.3816	0.6429	0.066*
H19	0.1477	0.1839	0.7121	0.066*
H20	0.0049	0.131	0.5748	0.069*
H21	0.045	0.2774	0.3682	0.056*
H22A	0.9951	0.9838	−0.1435	0.077*
H22B	0.8451	0.9539	−0.0118	0.077*
H22C	0.818	1.0469	−0.1409	0.077*
H27A	0.2116	0.8102	−0.3321	0.111*
H27B	0.2415	0.6682	−0.2355	0.111*
H27C	0.3934	0.753	−0.3452	0.111*
H30A	0.6176	1.1374	−0.3902	0.106*
H30B	0.5701	1.1381	−0.2375	0.106*
H30C	0.4444	1.074	−0.2946	0.106*

	U11	U22	U33	U12	U13	U23
O1	0.0240 (5)	0.0430 (6)	0.0331 (5)	−0.0036 (4)	−0.0093 (4)	0.0024 (4)
O2	0.0248 (5)	0.0739 (8)	0.0630 (7)	−0.0045 (5)	−0.0224 (5)	0.0132 (6)
O3	0.0334 (5)	0.0540 (6)	0.0446 (6)	0.0043 (5)	−0.0228 (5)	0.0007 (5)
O4	0.0364 (6)	0.0472 (6)	0.0381 (6)	0.0029 (4)	−0.0061 (4)	0.0083 (5)
O5	0.0218 (5)	0.0456 (6)	0.0403 (5)	−0.0040 (4)	−0.0082 (4)	−0.0067 (4)
O6	0.0240 (5)	0.0570 (6)	0.0364 (5)	−0.0039 (4)	−0.0151 (4)	0.0057 (4)
C5	0.0227 (6)	0.0339 (7)	0.0350 (7)	0.0019 (5)	−0.0114 (5)	−0.0058 (6)
C9	0.0233 (6)	0.0362 (7)	0.0309 (7)	0.0014 (5)	−0.0117 (5)	−0.0051 (5)
C4	0.0239 (6)	0.0336 (7)	0.0302 (7)	0.0006 (5)	−0.0097 (5)	−0.0036 (5)
C8	0.0216 (6)	0.0345 (7)	0.0328 (7)	−0.0001 (5)	−0.0081 (5)	−0.0071 (5)
C1	0.0239 (6)	0.0391 (7)	0.0434 (8)	0.0009 (5)	−0.0134 (6)	−0.0057 (6)
C6	0.0264 (6)	0.0369 (7)	0.0354 (7)	0.0051 (5)	−0.0153 (6)	−0.0044 (6)
C2	0.0218 (6)	0.0427 (8)	0.0430 (8)	−0.0027 (5)	−0.0077 (6)	−0.0039 (6)
C7	0.0281 (7)	0.0336 (7)	0.0307 (7)	0.0020 (5)	−0.0093 (5)	−0.0024 (5)
C3	0.0247 (6)	0.0361 (7)	0.0355 (7)	−0.0012 (5)	−0.0057 (5)	−0.0057 (6)
C10	0.0278 (7)	0.0403 (8)	0.0332 (7)	0.0019 (6)	−0.0047 (5)	−0.0041 (6)
C11	0.0360 (8)	0.0560 (10)	0.0431 (8)	−0.0103 (7)	−0.0132 (7)	0.0023 (7)
C12	0.0441 (9)	0.0773 (12)	0.0404 (9)	−0.0070 (8)	−0.0160 (7)	0.0031 (8)
C13	0.0510 (10)	0.0644 (11)	0.0386 (9)	−0.0040 (8)	−0.0068 (7)	0.0091 (8)
C14	0.0588 (11)	0.0530 (10)	0.0482 (10)	−0.0184 (8)	−0.0038 (8)	0.0031 (8)
C15	0.0462 (9)	0.0517 (9)	0.0393 (8)	−0.0123 (7)	−0.0082 (7)	−0.0052 (7)
C16	0.0701 (13)	0.1072 (17)	0.0656 (12)	0.0106 (12)	−0.0457 (11)	−0.0277 (12)
C17	0.0703 (13)	0.0491 (10)	0.0732 (13)	0.0092 (9)	−0.0106 (10)	0.0160 (9)
C18	0.0378 (8)	0.0454 (9)	0.0718 (11)	−0.0098 (7)	−0.0173 (8)	−0.0089 (8)

O3—C6	1.3753 (15)	C5—C6	1.4120 (19)
O3—C16	1.422 (2)	C5—C1	1.4757 (18)
O2—C1	1.2341 (16)	C9—C8	1.3798 (18)
O5—C8	1.3724 (15)	C9—C4	1.3992 (18)
O5—C18	1.4193 (19)	C8—C7	1.4024 (18)
C18—H22A	0.9600	C1—C2	1.438 (2)
C18—H22B	0.9600	C6—C7	1.3857 (19)
C18—H22C	0.9600	C2—C3	1.3430 (19)
C16—H27A	0.9600	C2—H8A	0.9300
C16—H27B	0.9600	C3—C10	1.4735 (19)
C16—H27C	0.9600	C10—C15	1.386 (2)
O6—C9	1.3552 (15)	C10—C11	1.393 (2)
O6—H8	0.8200	C15—C14	1.384 (2)
O4—C7	1.3687 (16)	C15—H21	0.9300
O4—C17	1.408 (2)	C12—C13	1.372 (3)
C17—H30A	0.9600	C12—C11	1.378 (2)
C17—H30B	0.9600	C12—H18	0.9300
C17—H30C	0.9600	C11—H17	0.9300
O1—C3	1.3599 (16)	C13—C14	1.380 (3)
O1—C4	1.3733 (16)	C13—H19	0.9300
C5—C4	1.4009 (17)	C14—H20	0.9300
C6—O3—C16	113.82 (13)	C9—C8—C7	121.45 (12)
C8—O5—C18	114.34 (11)	O2—C1—C2	121.77 (13)
O5—C18—H22A	109.5	O2—C1—C5	123.02 (13)
O5—C18—H22B	109.5	C2—C1—C5	115.18 (11)
H22A—C18—H22B	109.5	O3—C6—C7	118.28 (12)
O5—C18—H22C	109.5	O3—C6—C5	121.32 (12)
H22A—C18—H22C	109.5	C7—C6—C5	120.36 (12)
H22B—C18—H22C	109.5	C3—C2—C1	122.86 (12)
O3—C16—H27A	109.5	C3—C2—H8A	118.6
O3—C16—H27B	109.5	C1—C2—H8A	118.6
H27A—C16—H27B	109.5	O4—C7—C6	122.84 (12)
O3—C16—H27C	109.5	O4—C7—C8	117.18 (12)
H27A—C16—H27C	109.5	C6—C7—C8	119.84 (12)
H27B—C16—H27C	109.5	C2—C3—O1	121.83 (12)
C9—O6—H8	109.5	C2—C3—C10	126.44 (12)
C7—O4—C17	117.76 (13)	O1—C3—C10	111.69 (11)
O4—C17—H30A	109.5	C15—C10—C11	119.00 (14)
O4—C17—H30B	109.5	C15—C10—C3	120.60 (13)
H30A—C17—H30B	109.5	C11—C10—C3	120.40 (13)
O4—C17—H30C	109.5	C14—C15—C10	120.13 (15)
H30A—C17—H30C	109.5	C14—C15—H21	119.9
H30B—C17—H30C	109.5	C10—C15—H21	119.9
C3—O1—C4	119.21 (10)	C13—C12—C11	120.27 (16)
C4—C5—C6	117.91 (12)	C13—C12—H18	119.9
C4—C5—C1	117.68 (12)	C11—C12—H18	119.9
C6—C5—C1	124.41 (12)	C12—C11—C10	120.38 (15)
O6—C9—C8	123.53 (11)	C12—C11—H17	119.8
O6—C9—C4	118.48 (11)	C10—C11—H17	119.8
C8—C9—C4	117.98 (11)	C12—C13—C14	119.99 (15)
O1—C4—C9	114.47 (11)	C12—C13—H19	120.0
O1—C4—C5	123.14 (11)	C14—C13—H19	120.0
C9—C4—C5	122.39 (12)	C13—C14—C15	120.22 (16)
O5—C8—C9	117.81 (11)	C13—C14—H20	119.9
O5—C8—C7	120.68 (12)	C15—C14—H20	119.9
C3—O1—C4—C9	−178.49 (11)	C5—C1—C2—C3	3.3 (2)
C3—O1—C4—C5	2.30 (19)	C17—O4—C7—C6	60.8 (2)
O6—C9—C4—O1	2.27 (18)	C17—O4—C7—C8	−123.44 (17)
C8—C9—C4—O1	−176.89 (11)	O3—C6—C7—O4	−4.1 (2)
O6—C9—C4—C5	−178.52 (12)	C5—C6—C7—O4	178.13 (12)
C8—C9—C4—C5	2.3 (2)	O3—C6—C7—C8	−179.74 (12)
C6—C5—C4—O1	177.67 (12)	C5—C6—C7—C8	2.4 (2)
C1—C5—C4—O1	−1.7 (2)	O5—C8—C7—O4	−0.13 (19)
C6—C5—C4—C9	−1.5 (2)	C9—C8—C7—O4	−177.50 (12)
C1—C5—C4—C9	179.16 (12)	O5—C8—C7—C6	175.80 (12)
C18—O5—C8—C9	−94.47 (15)	C9—C8—C7—C6	−1.6 (2)
C18—O5—C8—C7	88.06 (16)	C1—C2—C3—O1	−2.9 (2)
O6—C9—C8—O5	2.7 (2)	C1—C2—C3—C10	174.87 (13)
C4—C9—C8—O5	−178.22 (11)	C4—O1—C3—C2	0.0 (2)
O6—C9—C8—C7	−179.89 (12)	C4—O1—C3—C10	−178.04 (11)
C4—C9—C8—C7	−0.8 (2)	C2—C3—C10—C15	34.3 (2)
C4—C5—C1—O2	176.96 (14)	O1—C3—C10—C15	−147.80 (14)
C6—C5—C1—O2	−2.4 (2)	C2—C3—C10—C11	−145.11 (16)
C4—C5—C1—C2	−0.99 (19)	O1—C3—C10—C11	32.83 (18)
C6—C5—C1—C2	179.69 (13)	C11—C10—C15—C14	−0.8 (2)
C16—O3—C6—C7	94.31 (17)	C3—C10—C15—C14	179.80 (15)
C16—O3—C6—C5	−87.89 (18)	C13—C12—C11—C10	1.2 (3)
C4—C5—C6—O3	−178.70 (12)	C15—C10—C11—C12	−0.3 (2)
C1—C5—C6—O3	0.6 (2)	C3—C10—C11—C12	179.07 (15)
C4—C5—C6—C7	−1.0 (2)	C11—C12—C13—C14	−0.9 (3)
C1—C5—C6—C7	178.37 (13)	C12—C13—C14—C15	−0.2 (3)
O2—C1—C2—C3	−174.72 (15)	C10—C15—C14—C13	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H8···O5	0.82	2.35	2.770 (1)	113
O6—H8···O2i	0.82	1.94	2.727 (1)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H8⋯O5	0.82	2.35	2.770 (1)	113
O6—H8⋯O2i	0.82	1.94	2.727 (1)	160

Symmetry code: (i) .