organic compounds
Acta Crystallographica Section E
b = 9.0878 (2) Å
c = 10.7832 (3) Å
= 79.545 (2)
= 71.5640 (10)
= 86.925 (2)
V = 772.85 (3) Å3
Structure Reports
Online
ISSN 1600-5368
8-Hydroxy-5,6,7-trimethoxy-2-phenyl4H-chromen-4-one
Jahyr E. Theodoro,a Djalma Santos,b Hiram Pérez,c*
Maria Fátima das Graças Fernandes da Silvab and
J. Ellenaa
a
Instituto de Fı́sica de São Carlos-USP, Cx Postal 369, 13560-970 São Carlos, SP,
Brazil, bDepartamento Quı́mica-UFSCar, Cx Postal 676, 13565-905 São Carlos, SP,
Brazil, and cDepartamento de Quı́mica Inorgánica, Facultad de Quı́mica,
Universidad de la Habana, Habana 10400, Cuba
Correspondence e-mail: hperez@fq.uh.cu
Z=2
Mo K radiation
= 0.11 mm1
T = 294 K
0.22 0.19 0.11 mm
Data collection
3153 independent reflections
2512 reflections with I > 2(I)
Rint = 0.049
Nonius Kappa CCD diffractometer
Absorption correction: none
20499 measured reflections
Refinement
R[F 2 > 2(F 2)] = 0.042
wR(F 2) = 0.123
S = 1.07
3153 reflections
218 parameters
H-atom parameters constrained
max = 0.25 e Å3
min = 0.24 e Å3
Table 1
Hydrogen-bond geometry (Å, ).
Received 28 March 2008; accepted 17 April 2008
D—H A
D—H
H A
D A
D—H A
Key indicators: single-crystal X-ray study; T = 294 K; mean (C–C) = 0.002 Å;
R factor = 0.043; wR factor = 0.124; data-to-parameter ratio = 14.5.
O6—H8 O5
O6—H8 O2i
0.82
0.82
2.35
1.94
2.770 (1)
2.727 (1)
113
160
Symmetry code: (i) x þ 1; y; z.
In the title compound, C18H16O6, the benzopyran group is
essentially planar, with the O atoms of the substituent groups
lying close to its mean plane. The molecular conformation is
governed by intramolecular interactions. The crystal packing
is mainly determined by one classical intermolecular 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).
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).
The authors are grateful to Conselho Nacional de Desenvolvimento Cientı́fico e Tecnológico (CNPq), Fundação de
Amparo à Pesquisa do Estado de São Paulo (FAPESP) and
Coordenação de Aperfeiçoamento de Pessoal de Ensino
Superior (CAPES) for financial support.
Supplementary data and figures for this paper are available from the
IUCr electronic archives (Reference: BG2176).
References
Chebib, M. & Johnston, G. A. R. (2000). J. Med. Chem. 43, 1427–1447.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
Medina, J. H., Viola, H., Wolfman, C., Marder, M., Wasowski, C., Calvo, D. &
Paladini, A. C. (1998). Phytomedicine, 5, 235–243.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter & R. M.
Sweet, pp. 307–326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Experimental
Crystal data
C18H16O6
Mr = 328.32
Acta Cryst. (2008). E64, o899
Triclinic, P1
a = 8.4536 (2) Å
doi:10.1107/S1600536808010696
Theodoro et al.
o899
supporting information
supporting information
Acta Cryst. (2008). E64, o899
[doi:10.1107/S1600536808010696]
8-Hydroxy-5,6,7-trimethoxy-2-phenyl-4H-chromen-4-one
Jahyr E. Theodoro, Djalma Santos, Hiram Pérez, Maria Fátima das Graças Fernandes da Silva
and J. Ellena
S1. Comment
A number of differents flavones are known to have interesting modulatory activities at Gamma-aminobutyric acid
receptors (GABA-A), an inhibitory neurotransmitter found in the nervous systems of widely divergent species. It is the
main inhibitory neurotransmitter in the central nervous system (Medina et al., 1998; Chebib & Johnston, 2000).
Figure 1 shows an ORTEP view of thr title compound, 8-hydroxy-5,6,7-trymethoxy-2-phenylchromen-4-one (I) with
atom labeling and 50% probability displacement ellipsoids. The benzopyran group in (I) is essentially planar, with the
oxygen atoms of the substituent groups lying close to its mean plane. The ring forms angles of 113.8 (4)°, 117.8 (3)° and
114.4 (2)° with the O3—C16, O4—C17 and O5—C18 methoxy groups, respectively, and 34.61 (4)° with the phenyl ring.
The molecular conformation is fixed by intramolecular interactions (Table 1 and Figure 1). The crystal packing is
mainly determined by one classical intermolecular H bond which gives rise to the formation of an infinite chain along the
a axis (Table 1 and Figure 2).
S2. Experimental
Selected parts of the Z. montana plant (Branches and leaves) were dried carefully by forced air at 40 °C and reduced to
powder. The resulting material was macerated three times with hexane, followed with methanol at room temperature for
72 h each. After the evaporation of the solvent under reduced pressure, crude extracts were obtained. A well shaped
single-crystal of the title compound was selected for the XRD experiments.
S3. Refinement
All the hydrogen atoms were stereochemically positioned and refined with a riding model. Hydrogen atoms of the CH
and CH2 groups were set isotropic with a thermal parameter 20% greater than the equivalent isotropic displacement
parameter of the atom to which each one was bonded. This percentage was set to 50% for the hydrogen atoms of the CH3
and OH groups.
Acta Cryst. (2008). E64, o899
sup-1
supporting information
Figure 1
View of (I) (50% probability displacement ellipsoids)
Figure 2
View of the intermolecular interaction that gives rise to the formation of a chain along the a axis.
8-Hydroxy-5,6,7-trimethoxy-2-phenyl-4H-chromen-4-one
Crystal data
C18H16O6
Mr = 328.32
Triclinic, P1
Hall symbol: -P 1
a = 8.4536 (2) Å
b = 9.0878 (2) Å
c = 10.7832 (3) Å
α = 79.545 (2)°
β = 71.564 (1)°
γ = 86.925 (2)°
V = 772.85 (3) Å3
Acta Cryst. (2008). E64, o899
Z=2
F(000) = 344
Dx = 1.411 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 20513 reflections
θ = 2.9–26.4°
µ = 0.11 mm−1
T = 294 K
Prism, yellow
0.22 × 0.19 × 0.11 mm
sup-2
supporting information
Data collection
Rint = 0.049
θmax = 26.4°, θmin = 3.3°
h = −10→10
k = −11→11
l = −13→13
KappaCCD
diffractometer
φ scans and ω scans winth κ offsets
20499 measured reflections
3153 independent reflections
2512 reflections with I > 2σ(I)
Refinement
w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1467P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.25 e Å−3
Δρmin = −0.24 e Å−3
Extinction correction: SHELXL97 (Sheldrick,
2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Extinction coefficient: 0.043 (11)
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.042
wR(F2) = 0.124
S = 1.07
3153 reflections
218 parameters
0 restraints
H-atom parameters constrained
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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
O1
O2
O3
O4
O5
O6
C1
C2
C3
C4
C5
C6
C7
C8
C9
C10
C11
C12
C13
C14
C15
C16
C17
x
y
z
Uiso*/Ueq
0.40508 (11)
0.05483 (13)
0.29650 (12)
0.63074 (13)
0.83892 (11)
0.71943 (11)
0.16504 (16)
0.13054 (16)
0.24520 (16)
0.45089 (16)
0.33896 (15)
0.39952 (16)
0.56421 (16)
0.67300 (15)
0.61900 (15)
0.21737 (17)
0.30333 (19)
0.2755 (2)
0.1650 (2)
0.0795 (2)
0.1043 (2)
0.2848 (3)
0.5601 (3)
0.55938 (11)
0.68927 (14)
0.85689 (12)
0.94104 (12)
0.83118 (11)
0.63816 (12)
0.64776 (16)
0.54641 (16)
0.50867 (15)
0.65179 (15)
0.70155 (15)
0.80083 (15)
0.84828 (15)
0.79300 (15)
0.69429 (15)
0.41557 (16)
0.44556 (19)
0.3598 (2)
0.2423 (2)
0.2109 (2)
0.29793 (19)
0.7646 (3)
1.0840 (2)
0.19334 (9)
0.00920 (12)
−0.19401 (10)
−0.28518 (10)
−0.14212 (9)
0.09768 (9)
0.06016 (15)
0.18467 (14)
0.24709 (13)
0.07187 (13)
0.00135 (13)
−0.12037 (13)
−0.16628 (13)
−0.09404 (13)
0.02441 (13)
0.37915 (13)
0.46281 (16)
0.58706 (16)
0.62864 (17)
0.54662 (17)
0.42257 (16)
−0.2840 (2)
−0.3033 (2)
0.0343 (3)
0.0550 (3)
0.0428 (3)
0.0441 (3)
0.0362 (3)
0.0395 (3)
0.0350 (3)
0.0368 (3)
0.0330 (3)
0.0 (3)
0.0301 (3)
0.0320 (3)
0.0313 (3)
0.0296 (3)
0.0295 (3)
0.0353 (3)
0.0459 (4)
0.0547 (5)
0.0552 (5)
0.0573 (5)
0.0469 (4)
0.0738 (6)
0.0708 (6)
Acta Cryst. (2008). E64, o899
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supporting information
C18
H8
H8A
H17
H18
H19
H20
H21
H22A
H22B
H22C
H27A
H27B
H27C
H30A
H30B
H30C
0.8774 (2)
0.8139
0.0242
0.3799
0.3319
0.1477
0.0049
0.045
0.9951
0.8451
0.818
0.2116
0.2415
0.3934
0.6176
0.5701
0.4444
0.96476 (19)
0.672
0.5052
0.5239
0.3816
0.1839
0.131
0.2774
0.9838
0.9539
1.0469
0.8102
0.6682
0.753
1.1374
1.1381
1.074
−0.10671 (19)
0.0606
0.2237
0.4346
0.6429
0.7121
0.5748
0.3682
−0.1435
−0.0118
−0.1409
−0.3321
−0.2355
−0.3452
−0.3902
−0.2375
−0.2946
0.0514 (4)
0.059*
0.044*
0.055*
0.066*
0.066*
0.069*
0.056*
0.077*
0.077*
0.077*
0.111*
0.111*
0.111*
0.106*
0.106*
0.106*
Atomic displacement parameters (Å2)
O1
O2
O3
O4
O5
O6
C5
C9
C4
C8
C1
C6
C2
C7
C3
C10
C11
C12
C13
C14
C15
C16
C17
C18
U11
U22
U33
U12
U13
U23
0.0240 (5)
0.0248 (5)
0.0334 (5)
0.0364 (6)
0.0218 (5)
0.0240 (5)
0.0227 (6)
0.0233 (6)
0.0239 (6)
0.0216 (6)
0.0239 (6)
0.0264 (6)
0.0218 (6)
0.0281 (7)
0.0247 (6)
0.0278 (7)
0.0360 (8)
0.0441 (9)
0.0510 (10)
0.0588 (11)
0.0462 (9)
0.0701 (13)
0.0703 (13)
0.0378 (8)
0.0430 (6)
0.0739 (8)
0.0540 (6)
0.0472 (6)
0.0456 (6)
0.0570 (6)
0.0339 (7)
0.0362 (7)
0.0336 (7)
0.0345 (7)
0.0391 (7)
0.0369 (7)
0.0427 (8)
0.0336 (7)
0.0361 (7)
0.0403 (8)
0.0560 (10)
0.0773 (12)
0.0644 (11)
0.0530 (10)
0.0517 (9)
0.1072 (17)
0.0491 (10)
0.0454 (9)
0.0331 (5)
0.0630 (7)
0.0446 (6)
0.0381 (6)
0.0403 (5)
0.0364 (5)
0.0350 (7)
0.0309 (7)
0.0302 (7)
0.0328 (7)
0.0434 (8)
0.0354 (7)
0.0430 (8)
0.0307 (7)
0.0355 (7)
0.0332 (7)
0.0431 (8)
0.0404 (9)
0.0386 (9)
0.0482 (10)
0.0393 (8)
0.0656 (12)
0.0732 (13)
0.0718 (11)
−0.0036 (4)
−0.0045 (5)
0.0043 (5)
0.0029 (4)
−0.0040 (4)
−0.0039 (4)
0.0019 (5)
0.0014 (5)
0.0006 (5)
−0.0001 (5)
0.0009 (5)
0.0051 (5)
−0.0027 (5)
0.0020 (5)
−0.0012 (5)
0.0019 (6)
−0.0103 (7)
−0.0070 (8)
−0.0040 (8)
−0.0184 (8)
−0.0123 (7)
0.0106 (12)
0.0092 (9)
−0.0098 (7)
−0.0093 (4)
−0.0224 (5)
−0.0228 (5)
−0.0061 (4)
−0.0082 (4)
−0.0151 (4)
−0.0114 (5)
−0.0117 (5)
−0.0097 (5)
−0.0081 (5)
−0.0134 (6)
−0.0153 (6)
−0.0077 (6)
−0.0093 (5)
−0.0057 (5)
−0.0047 (5)
−0.0132 (7)
−0.0160 (7)
−0.0068 (7)
−0.0038 (8)
−0.0082 (7)
−0.0457 (11)
−0.0106 (10)
−0.0173 (8)
0.0024 (4)
0.0132 (6)
0.0007 (5)
0.0083 (5)
−0.0067 (4)
0.0057 (4)
−0.0058 (6)
−0.0051 (5)
−0.0036 (5)
−0.0071 (5)
−0.0057 (6)
−0.0044 (6)
−0.0039 (6)
−0.0024 (5)
−0.0057 (6)
−0.0041 (6)
0.0023 (7)
0.0031 (8)
0.0091 (8)
0.0031 (8)
−0.0052 (7)
−0.0277 (12)
0.0160 (9)
−0.0089 (8)
Acta Cryst. (2008). E64, o899
sup-4
supporting information
Geometric parameters (Å, º)
O3—C6
O3—C16
O2—C1
O5—C8
O5—C18
C18—H22A
C18—H22B
C18—H22C
C16—H27A
C16—H27B
C16—H27C
O6—C9
O6—H8
O4—C7
O4—C17
C17—H30A
C17—H30B
C17—H30C
O1—C3
O1—C4
C5—C4
1.3753 (15)
1.422 (2)
1.2341 (16)
1.3724 (15)
1.4193 (19)
0.9600
0.9600
0.9600
0.9600
0.9600
0.9600
1.3552 (15)
0.8200
1.3687 (16)
1.408 (2)
0.9600
0.9600
0.9600
1.3599 (16)
1.3733 (16)
1.4009 (17)
C5—C6
C5—C1
C9—C8
C9—C4
C8—C7
C1—C2
C6—C7
C2—C3
C2—H8A
C3—C10
C10—C15
C10—C11
C15—C14
C15—H21
C12—C13
C12—C11
C12—H18
C11—H17
C13—C14
C13—H19
C14—H20
1.4120 (19)
1.4757 (18)
1.3798 (18)
1.3992 (18)
1.4024 (18)
1.438 (2)
1.3857 (19)
1.3430 (19)
0.9300
1.4735 (19)
1.386 (2)
1.393 (2)
1.384 (2)
0.9300
1.372 (3)
1.378 (2)
0.9300
0.9300
1.380 (3)
0.9300
0.9300
C6—O3—C16
C8—O5—C18
O5—C18—H22A
O5—C18—H22B
H22A—C18—H22B
O5—C18—H22C
H22A—C18—H22C
H22B—C18—H22C
O3—C16—H27A
O3—C16—H27B
H27A—C16—H27B
O3—C16—H27C
H27A—C16—H27C
H27B—C16—H27C
C9—O6—H8
C7—O4—C17
O4—C17—H30A
O4—C17—H30B
H30A—C17—H30B
O4—C17—H30C
H30A—C17—H30C
H30B—C17—H30C
C3—O1—C4
C4—C5—C6
113.82 (13)
114.34 (11)
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
109.5
117.76 (13)
109.5
109.5
109.5
109.5
109.5
109.5
119.21 (10)
117.91 (12)
C9—C8—C7
O2—C1—C2
O2—C1—C5
C2—C1—C5
O3—C6—C7
O3—C6—C5
C7—C6—C5
C3—C2—C1
C3—C2—H8A
C1—C2—H8A
O4—C7—C6
O4—C7—C8
C6—C7—C8
C2—C3—O1
C2—C3—C10
O1—C3—C10
C15—C10—C11
C15—C10—C3
C11—C10—C3
C14—C15—C10
C14—C15—H21
C10—C15—H21
C13—C12—C11
C13—C12—H18
121.45 (12)
121.77 (13)
123.02 (13)
115.18 (11)
118.28 (12)
121.32 (12)
120.36 (12)
122.86 (12)
118.6
118.6
122.84 (12)
117.18 (12)
119.84 (12)
121.83 (12)
126.44 (12)
111.69 (11)
119.00 (14)
120.60 (13)
120.40 (13)
120.13 (15)
119.9
119.9
120.27 (16)
119.9
Acta Cryst. (2008). E64, o899
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supporting information
C4—C5—C1
C6—C5—C1
O6—C9—C8
O6—C9—C4
C8—C9—C4
O1—C4—C9
O1—C4—C5
C9—C4—C5
O5—C8—C9
O5—C8—C7
117.68 (12)
124.41 (12)
123.53 (11)
118.48 (11)
117.98 (11)
114.47 (11)
123.14 (11)
122.39 (12)
117.81 (11)
120.68 (12)
C11—C12—H18
C12—C11—C10
C12—C11—H17
C10—C11—H17
C12—C13—C14
C12—C13—H19
C14—C13—H19
C13—C14—C15
C13—C14—H20
C15—C14—H20
119.9
120.38 (15)
119.8
119.8
119.99 (15)
120.0
120.0
120.22 (16)
119.9
119.9
C3—O1—C4—C9
C3—O1—C4—C5
O6—C9—C4—O1
C8—C9—C4—O1
O6—C9—C4—C5
C8—C9—C4—C5
C6—C5—C4—O1
C1—C5—C4—O1
C6—C5—C4—C9
C1—C5—C4—C9
C18—O5—C8—C9
C18—O5—C8—C7
O6—C9—C8—O5
C4—C9—C8—O5
O6—C9—C8—C7
C4—C9—C8—C7
C4—C5—C1—O2
C6—C5—C1—O2
C4—C5—C1—C2
C6—C5—C1—C2
C16—O3—C6—C7
C16—O3—C6—C5
C4—C5—C6—O3
C1—C5—C6—O3
C4—C5—C6—C7
C1—C5—C6—C7
O2—C1—C2—C3
−178.49 (11)
2.30 (19)
2.27 (18)
−176.89 (11)
−178.52 (12)
2.3 (2)
177.67 (12)
−1.7 (2)
−1.5 (2)
179.16 (12)
−94.47 (15)
88.06 (16)
2.7 (2)
−178.22 (11)
−179.89 (12)
−0.8 (2)
176.96 (14)
−2.4 (2)
−0.99 (19)
179.69 (13)
94.31 (17)
−87.89 (18)
−178.70 (12)
0.6 (2)
−1.0 (2)
178.37 (13)
−174.72 (15)
C5—C1—C2—C3
C17—O4—C7—C6
C17—O4—C7—C8
O3—C6—C7—O4
C5—C6—C7—O4
O3—C6—C7—C8
C5—C6—C7—C8
O5—C8—C7—O4
C9—C8—C7—O4
O5—C8—C7—C6
C9—C8—C7—C6
C1—C2—C3—O1
C1—C2—C3—C10
C4—O1—C3—C2
C4—O1—C3—C10
C2—C3—C10—C15
O1—C3—C10—C15
C2—C3—C10—C11
O1—C3—C10—C11
C11—C10—C15—C14
C3—C10—C15—C14
C13—C12—C11—C10
C15—C10—C11—C12
C3—C10—C11—C12
C11—C12—C13—C14
C12—C13—C14—C15
C10—C15—C14—C13
3.3 (2)
60.8 (2)
−123.44 (17)
−4.1 (2)
178.13 (12)
−179.74 (12)
2.4 (2)
−0.13 (19)
−177.50 (12)
175.80 (12)
−1.6 (2)
−2.9 (2)
174.87 (13)
0.0 (2)
−178.04 (11)
34.3 (2)
−147.80 (14)
−145.11 (16)
32.83 (18)
−0.8 (2)
179.80 (15)
1.2 (3)
−0.3 (2)
179.07 (15)
−0.9 (3)
−0.2 (3)
1.1 (3)
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
O6—H8···O5
O6—H8···O2i
0.82
0.82
2.35
1.94
2.770 (1)
2.727 (1)
113
160
Symmetry code: (i) x+1, y, z.
Acta Cryst. (2008). E64, o899
sup-6
Hiram Rutes Perez