organic papers
Acta Cryst.(2006). E62, o2385–o2386 doi:10.1107/S160053680601734X Liet al. C
18H16O5
o2385
Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
1-[2-(4-Hydroxyphenyl)-4,6-dimethoxy-1-benzo-furan-3-yl]ethanone
Xiao-Xiao Li, Yu-Ping Wei, Ye-Fei Nan, Chang-Hua Hua and Liang-Dong Sun*
Department of Chemistry, College of Sciences, Tianjin University, Tianjin 300072, People’s Republic of China
Correspondence e-mail: doristju@gmail.com
Key indicators
Single-crystal X-ray study
T= 294 K
Mean(C–C) = 0.002 A˚
Rfactor = 0.048
wRfactor = 0.147
Data-to-parameter ratio = 15.9
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 29 April 2006 Accepted 10 May 2006
#2006 International Union of Crystallography
All rights reserved
In the crystal structure of the title compound, C18H16O5, O—
H O hydrogen bonds connect the molecules into centro-symmetric dimers that form stacks down theaaxis.
Comment
The structure of the title compound, (I), a 2-phenylbenzofuran derivative prepared by oxidation of the corresponding substituted flavylium salt (Jurd, 1964) is presented here (Fig. 1 and Table 1).
The atoms of the benzofuran ring system are almost coplanar, the mean deviation from the C1–C8/O1 mean plane being 0.0102 (2) A˚ . The benzofuran system and its hydroxy-phenyl substituent are inclined at a dihedral angle of 33.5 (1),
with a C4—O1—C1—C9 torsion angle of 179.78 (12). The
angles about C1 are significantly distorted from trigonal geometry (Table 1). In particular, the widening of the C2— C1—C9 angle [136.80 (16)] may reflect steric interaction
beween the hydroxyphenyl and ethanone substituents. In the crystal structure, O—H O hydrogen bonds link adjacent molecules into centrosymmetric dimers (Table 2). An intermolecular -stacking interaction, with a centroid– centroid distance of 3.566 (2) A˚ , between the furan ring and the fused benzene ring of an adjacent molecule, forms stacks along theaaxis (Fig. 2).
Experimental
The title compound was prepared according to the procedure of Jurd (1964). Suitable crystals were obtained by evaporation of an ethyl acetate/hexane (1:1v/v) solution (m.p. 446 K).
Crystal data
C18H16O5
Mr= 312.32
Monoclinic,P21=a
a= 7.8442 (12) A˚
b= 18.365 (3) A˚
c= 10.7516 (18) A˚
= 105.781 (7)
V= 1490.5 (4) A˚3
Z= 4
Dx= 1.392 Mg m 3
MoKradiation
= 0.10 mm1
Data collection
Rigaku Saturn diffractometer
!scans
Absorption correction: multi-scan (REQAB; Jacobson, 1998)
Tmin= 0.974,Tmax= 0.980
9260 measured reflections 3401 independent reflections 2251 reflections withI> 2(I)
Rint= 0.061
max= 27.5
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.048
wR(F2) = 0.147
S= 1.04 3401 reflections 214 parameters
H-atom parameters constrained
w= 1/[2
(Fo2) + (0.0789P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.35 e A˚
3
min=0.30 e A˚
3
Table 1
Selected bond and torsion angles ().
O1—C1—C2 110.54 (14) O1—C1—C9 112.66 (14)
C2—C1—C9 136.80 (16)
[image:2.610.314.562.71.258.2]C4—O1—C1—C9 179.78 (12)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O2—H2 O3i 0.94 (3) 1.85 (3) 2.781 (2) 170 (3)
Symmetry code: (i)xþ1;yþ1;zþ1.
All H atoms were positioned geometrically and refined as riding (C—H = 0.93–0.96 A˚ ); for the CH and CH2groups, Uiso(H) values
were set equal to 1.2Ueq(C) [1.5Ueq(C) for the methyl groups].
Data collection:CrystalClear(Molecular Structure Corporation & Rigaku, 1999); cell refinement: CrystalClear; data reduction: Crys-talStructure(Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97(Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: CrystalStructure.
References
Bruker (1997). SHELXTL. Version 5.10. Bruker AXS Inc., Madison, Wisconsin, USA.
Jacobson, R. (1998).REQAB. Private communication to Rigaku Corporation, Tokyo, Japan.
Jurd, L. (1964).J. Org. Chem.29, 2602–2605.
Molecular Structure Corporation & Rigaku (1999). CrystalClear. Version 1.3.6. MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA, and Rigaku, 3-9-12 Akishima, Tokyo, Japan.
Rigaku/MSC (2005).CrystalStructure. Version 3.7.0. MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA .
Sheldrick, G. M. (1990).Acta Cryst.A46, 467–473.
Sheldrick, G. M. (1997).SHELXL97. University of Go¨ttingen, Germany. Figure 2
The crystal packing of (I), viewed approximately down the a axis. Hydrogen bonds are shown as dashed lines.
Figure 1
[image:2.610.316.564.299.505.2]supporting information
sup-1 Acta Cryst. (2006). E62, o2385–o2386
supporting information
Acta Cryst. (2006). E62, o2385–o2386 [https://doi.org/10.1107/S160053680601734X]
1-[2-(4-Hydroxyphenyl)-4,6-dimethoxy-1-benzofuran-3-yl]ethanone
Xiao-Xiao Li, Yu-Ping Wei, Ye-Fei Nan, Chang-Hua Hua and Liang-Dong Sun
1-[4,6-Dimethoxy-2-(4-hydroxyphenyl)-1-benzofuran-3-yl]ethanone
Crystal data
C18H16O5
Mr = 312.32 Monoclinic, P21/a
Hall symbol: -P 2yab a = 7.8442 (12) Å b = 18.365 (3) Å c = 10.7516 (18) Å β = 105.781 (7)° V = 1490.5 (4) Å3
Z = 4
F(000) = 656.00 Dx = 1.392 Mg m−3
Melting point: 446 K
Mo Kα radiation, λ = 0.71070 Å Cell parameters from 2508 reflections θ = 3.1–27.5°
µ = 0.10 mm−1
T = 294 K Block, colorless 0.26 × 0.24 × 0.20 mm
Data collection
Rigaku Saturn diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
Detector resolution: 7.31 pixels mm-1
ω scans
Absorption correction: multi-scan (REQAB; Jacobson, 1998) Tmin = 0.974, Tmax = 0.980
9260 measured reflections 3401 independent reflections 2251 reflections with I > 2σ(I) Rint = 0.061
θmax = 27.5°, θmin = 3.1°
h = −10→10 k = −16→23 l = −12→13
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.048
wR(F2) = 0.147
S = 1.04 3401 reflections 214 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0789P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.35 e Å−3
Special details
Experimental. IR (KBr, cm-1): 3208, 2916, 1631, 1586; 1H NMR (CD
3COCD3): δ 7.673–7.655 (m, 2 H), 6.948–6.930 (m,
2H), 6.792–6.788 (d, 1H), 6.484–6.480 (d, 1H), 3.944 (s, 3H), 3.878 (s, 3H), 3.454 (s, 1H), 2.556–2.554 (d, 3 H). 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 (Å2)
x y z Uiso*/Ueq
O1 0.06237 (15) 0.34041 (6) 0.09951 (10) 0.0394 (3)
O2 0.3160 (2) 0.65123 (7) 0.30923 (16) 0.0601 (4)
H2 0.378 (4) 0.6507 (15) 0.398 (3) 0.112 (11)*
O3 0.49617 (18) 0.33356 (8) 0.43245 (13) 0.0602 (4)
O4 −0.17940 (19) 0.11923 (7) −0.12270 (13) 0.0592 (4)
O5 0.27885 (16) 0.11544 (7) 0.26779 (12) 0.0483 (4)
C1 0.1902 (2) 0.35238 (9) 0.21353 (16) 0.0365 (4)
C2 0.2566 (2) 0.28712 (9) 0.27017 (15) 0.0351 (4)
C3 0.1613 (2) 0.23011 (9) 0.18406 (15) 0.0344 (4)
C4 0.0457 (2) 0.26642 (9) 0.08197 (15) 0.0356 (4)
C5 −0.0721 (2) 0.23581 (10) −0.02554 (15) 0.0410 (4)
H5 −0.1458 0.2637 −0.0905 0.049*
C6 −0.0712 (2) 0.16098 (10) −0.02834 (16) 0.0415 (4)
C7 0.0446 (2) 0.12027 (10) 0.06927 (16) 0.0412 (4)
H7 0.0428 0.0697 0.0634 0.049*
C8 0.1616 (2) 0.15328 (9) 0.17406 (15) 0.0372 (4)
C9 0.2198 (2) 0.42969 (9) 0.24337 (15) 0.0366 (4)
C10 0.2648 (2) 0.45773 (10) 0.36872 (16) 0.0442 (4)
H10 0.2742 0.4263 0.4380 0.053*
C11 0.2953 (2) 0.53074 (10) 0.39200 (16) 0.0454 (5)
H11 0.3250 0.5481 0.4764 0.054*
C12 0.2820 (2) 0.57862 (10) 0.29026 (17) 0.0422 (4)
C13 0.2297 (2) 0.55274 (10) 0.16481 (17) 0.0473 (5)
H13 0.2146 0.5849 0.0958 0.057*
C14 0.2000 (2) 0.47933 (10) 0.14195 (16) 0.0424 (4)
H14 0.1660 0.4625 0.0572 0.051*
C15 0.3968 (2) 0.28167 (10) 0.39254 (16) 0.0397 (4)
C16 0.4238 (3) 0.21487 (12) 0.4729 (2) 0.0642 (6)
H16A 0.5219 0.2219 0.5479 0.077*
H16B 0.4483 0.1746 0.4235 0.077*
H16C 0.3187 0.2048 0.4993 0.077*
C17 −0.2939 (3) 0.15712 (12) −0.2296 (2) 0.0719 (7)
supporting information
sup-3 Acta Cryst. (2006). E62, o2385–o2386
H17B −0.2239 0.1853 −0.2727 0.086*
H17C −0.3707 0.1889 −0.1988 0.086*
C18 0.2729 (3) 0.03830 (11) 0.26189 (19) 0.0598 (6)
H18A 0.3621 0.0186 0.3335 0.072*
H18B 0.2942 0.0223 0.1824 0.072*
H18C 0.1583 0.0218 0.2657 0.072*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O1 0.0430 (6) 0.0320 (7) 0.0361 (7) −0.0027 (5) −0.0010 (5) −0.0024 (5)
O2 0.0837 (10) 0.0306 (7) 0.0554 (9) −0.0051 (7) 0.0009 (8) −0.0048 (6)
O3 0.0586 (8) 0.0463 (9) 0.0592 (9) −0.0065 (7) −0.0122 (7) −0.0075 (6)
O4 0.0719 (9) 0.0381 (8) 0.0496 (8) −0.0084 (7) −0.0138 (7) −0.0059 (6)
O5 0.0532 (7) 0.0344 (7) 0.0479 (8) 0.0051 (6) −0.0021 (6) 0.0016 (5)
C1 0.0376 (8) 0.0362 (10) 0.0322 (9) −0.0031 (7) 0.0034 (7) −0.0030 (7)
C2 0.0363 (8) 0.0328 (9) 0.0345 (9) −0.0032 (7) 0.0067 (7) −0.0024 (6)
C3 0.0327 (8) 0.0336 (9) 0.0358 (9) −0.0041 (7) 0.0073 (7) −0.0023 (7)
C4 0.0365 (8) 0.0323 (9) 0.0364 (9) −0.0041 (7) 0.0068 (7) −0.0025 (7)
C5 0.0436 (9) 0.0378 (10) 0.0352 (9) −0.0026 (7) 0.0000 (7) −0.0020 (7)
C6 0.0444 (9) 0.0379 (10) 0.0371 (10) −0.0078 (8) 0.0028 (7) −0.0066 (7)
C7 0.0470 (9) 0.0296 (9) 0.0439 (10) −0.0030 (7) 0.0070 (8) −0.0028 (7)
C8 0.0369 (8) 0.0348 (9) 0.0385 (10) 0.0011 (7) 0.0080 (7) 0.0007 (7)
C9 0.0366 (8) 0.0336 (9) 0.0362 (9) −0.0011 (7) 0.0043 (7) −0.0033 (7)
C10 0.0563 (11) 0.0368 (9) 0.0351 (10) 0.0013 (8) 0.0049 (8) 0.0003 (7)
C11 0.0550 (10) 0.0401 (10) 0.0346 (9) 0.0010 (8) 0.0013 (8) −0.0079 (8)
C12 0.0459 (9) 0.0303 (9) 0.0452 (10) −0.0014 (7) 0.0037 (8) −0.0052 (7)
C13 0.0615 (11) 0.0375 (10) 0.0395 (10) 0.0011 (9) 0.0081 (8) 0.0037 (8)
C14 0.0506 (10) 0.0398 (10) 0.0321 (9) −0.0008 (8) 0.0032 (8) −0.0043 (7)
C15 0.0366 (8) 0.0391 (10) 0.0398 (10) −0.0004 (7) 0.0043 (7) −0.0071 (7)
C16 0.0713 (14) 0.0532 (13) 0.0510 (12) −0.0120 (11) −0.0124 (10) 0.0078 (9) C17 0.0864 (16) 0.0539 (14) 0.0505 (13) −0.0052 (12) −0.0238 (11) −0.0052 (10) C18 0.0692 (13) 0.0333 (11) 0.0682 (14) 0.0064 (10) 0.0037 (11) 0.0066 (9)
Geometric parameters (Å, º)
O1—C4 1.3732 (19) C9—C10 1.396 (2)
O1—C1 1.3742 (19) C9—C14 1.397 (2)
O2—C12 1.364 (2) C10—C11 1.373 (2)
O2—H2 0.94 (3) C10—H10 0.9300
O3—C15 1.232 (2) C11—C12 1.385 (3)
O4—C6 1.367 (2) C11—H11 0.9300
O4—C17 1.432 (2) C12—C13 1.383 (2)
O5—C8 1.357 (2) C13—C14 1.379 (2)
O5—C18 1.418 (2) C13—H13 0.9300
C1—C2 1.380 (2) C14—H14 0.9300
C1—C9 1.460 (2) C15—C16 1.482 (3)
C2—C15 1.471 (2) C16—H16B 0.9600
C3—C4 1.389 (2) C16—H16C 0.9600
C3—C8 1.415 (2) C17—H17A 0.9600
C4—C5 1.388 (2) C17—H17B 0.9600
C5—C6 1.375 (2) C17—H17C 0.9600
C5—H5 0.9300 C18—H18A 0.9600
C6—C7 1.403 (2) C18—H18B 0.9600
C7—C8 1.384 (2) C18—H18C 0.9600
C7—H7 0.9300
C4—O1—C1 107.45 (12) C10—C11—C12 120.27 (16)
C12—O2—H2 99.6 (17) C10—C11—H11 119.9
C6—O4—C17 116.78 (16) C12—C11—H11 119.9
C8—O5—C18 118.10 (14) O2—C12—C13 118.41 (17)
O1—C1—C2 110.54 (14) O2—C12—C11 122.19 (16)
O1—C1—C9 112.66 (14) C13—C12—C11 119.39 (17)
C2—C1—C9 136.80 (16) C14—C13—C12 120.05 (17)
C1—C2—C3 106.02 (14) C14—C13—H13 120.0
C1—C2—C15 123.65 (15) C12—C13—H13 120.0
C3—C2—C15 130.33 (15) C13—C14—C9 121.42 (16)
C4—C3—C8 115.64 (14) C13—C14—H14 119.3
C4—C3—C2 105.55 (15) C9—C14—H14 119.3
C8—C3—C2 138.70 (15) O3—C15—C2 120.49 (17)
O1—C4—C5 122.15 (15) O3—C15—C16 117.42 (17)
O1—C4—C3 110.44 (13) C2—C15—C16 122.10 (15)
C5—C4—C3 127.41 (17) C15—C16—H16A 109.5
C6—C5—C4 114.65 (15) C15—C16—H16B 109.5
C6—C5—H5 122.7 H16A—C16—H16B 109.5
C4—C5—H5 122.7 C15—C16—H16C 109.5
O4—C6—C5 124.83 (16) H16A—C16—H16C 109.5
O4—C6—C7 113.67 (17) H16B—C16—H16C 109.5
C5—C6—C7 121.50 (15) O4—C17—H17A 109.5
C8—C7—C6 121.79 (17) O4—C17—H17B 109.5
C8—C7—H7 119.1 H17A—C17—H17B 109.5
C6—C7—H7 119.1 O4—C17—H17C 109.5
O5—C8—C7 123.06 (16) H17A—C17—H17C 109.5
O5—C8—C3 117.99 (14) H17B—C17—H17C 109.5
C7—C8—C3 118.94 (15) O5—C18—H18A 109.5
C10—C9—C14 117.27 (16) O5—C18—H18B 109.5
C10—C9—C1 123.66 (15) H18A—C18—H18B 109.5
C14—C9—C1 119.06 (14) O5—C18—H18C 109.5
C11—C10—C9 121.48 (16) H18A—C18—H18C 109.5
C11—C10—H10 119.3 H18B—C18—H18C 109.5
C9—C10—H10 119.3
C4—O1—C1—C2 −0.05 (17) C18—O5—C8—C3 176.57 (14)
C4—O1—C1—C9 −179.78 (12) C6—C7—C8—O5 −177.92 (15)
supporting information
sup-5 Acta Cryst. (2006). E62, o2385–o2386
C9—C1—C2—C3 179.46 (17) C4—C3—C8—O5 176.54 (14)
O1—C1—C2—C15 179.30 (14) C2—C3—C8—O5 0.9 (3)
C9—C1—C2—C15 −1.1 (3) C4—C3—C8—C7 −2.8 (2)
C1—C2—C3—C4 0.33 (17) C2—C3—C8—C7 −178.48 (17)
C15—C2—C3—C4 −179.09 (15) O1—C1—C9—C10 146.22 (16)
C1—C2—C3—C8 176.29 (18) C2—C1—C9—C10 −33.4 (3)
C15—C2—C3—C8 −3.1 (3) O1—C1—C9—C14 −32.8 (2)
C1—O1—C4—C5 −179.37 (15) C2—C1—C9—C14 147.61 (19)
C1—O1—C4—C3 0.27 (16) C14—C9—C10—C11 −2.5 (3)
C8—C3—C4—O1 −177.42 (12) C1—C9—C10—C11 178.45 (16)
C2—C3—C4—O1 −0.37 (17) C9—C10—C11—C12 −0.1 (3)
C8—C3—C4—C5 2.2 (2) C10—C11—C12—O2 −178.15 (17)
C2—C3—C4—C5 179.25 (15) C10—C11—C12—C13 3.0 (3)
O1—C4—C5—C6 179.63 (14) O2—C12—C13—C14 177.82 (16)
C3—C4—C5—C6 0.1 (2) C11—C12—C13—C14 −3.3 (3)
C17—O4—C6—C5 3.9 (3) C12—C13—C14—C9 0.7 (3)
C17—O4—C6—C7 −176.34 (18) C10—C9—C14—C13 2.2 (3)
C4—C5—C6—O4 178.07 (16) C1—C9—C14—C13 −178.71 (15)
C4—C5—C6—C7 −1.7 (2) C1—C2—C15—O3 −20.5 (3)
O4—C6—C7—C8 −178.77 (15) C3—C2—C15—O3 158.83 (17)
C5—C6—C7—C8 1.0 (3) C1—C2—C15—C16 159.00 (18)
C18—O5—C8—C7 −4.1 (2) C3—C2—C15—C16 −21.7 (3)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O2—H2···O3i 0.94 (3) 1.85 (3) 2.781 (2) 170 (3)