Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053056/at2439sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053056/at2439Isup2.hkl |
CCDC reference: 667488
2,4-dihydroxyacetophenone 10 g (0.066 mol) and anhyd. K2CO3 13.6 g (0.099 mol) was dissolved into 200 ml acetone and stirred for 0.5 h under room temperature. Then 1-bromo-3-methyl-2-butene 11.7 g (0.078 mol) was dropwised into the mixture, then stirred for 9 h at room temperature. The acetone was evaporated under pressure, and the pale red oil product was collected. Then 30 ml petroleum ether was added to the oil. The mixture was standing under 277 K, then white crystals were generated slowly. The white crystals were washed with cold petroleum ether [yield 78.2%, m.p. 315 K].
All H atoms were positioned geometrically and refined using a riding on their parent atoms, with C—H = 0.93 - 0.97 Å and O—H = 0.82 Å, and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C,O).
Sofalcone is an antiulcer agent which is effective for the treatment of gastric ulcer (Kazuaki & Katsuo, 1979). A smiliar structure, ethyl 2- [2-acetyl-5-(3-methylbut-2-enyloxy)phenoxy]acetate (Zhang et al., 2007), has been reported. Now, we present the crystal structure of the title compound.
The asymmetric unit of the title compound, (I), contains two independent molecules. In the two molecules, all O atoms don't significantly deviate from the benzene ring planar with r.m.s. deviations of 0.0103 (2) and 0.0114 (2) Å, repectively. Due to the p-π conjugation, the Csp2—O bonds [O3—C6 = 1.357 (2) Å and O6—C19 = 1.355 (2) Å] are significantly shorter than the Csp3—O bonds [O3—C9 = 1.437 (2) Å and O6—C22 = 1.433 (2) Å]. Intermolecular O—H···O hydrogen bonds (Table 1) are formed between the carbonyl and hydroxyl groups, which stabilize the crystal struture.
For related literature, see: Kazuaki & Katsuo (1979); Zhang et al. (2007).
Data collection: SAINT (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level. |
C13H16O3 | Z = 4 |
Mr = 220.26 | F(000) = 472 |
Triclinic, P1 | Dx = 1.229 Mg m−3 |
Hall symbol: -P 1 | Melting point: 315 K |
a = 9.7647 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.347 (2) Å | Cell parameters from 1972 reflections |
c = 11.553 (2) Å | θ = 2.6–25.9° |
α = 87.357 (3)° | µ = 0.09 mm−1 |
β = 86.416 (3)° | T = 293 K |
γ = 68.734 (3)° | Plate, colourless |
V = 1190.2 (4) Å3 | 0.46 × 0.30 × 0.24 mm |
Bruker SMART CCD area-detector diffractometer | 4187 independent reflections |
Radiation source: fine-focus sealed tube | 2542 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→7 |
Tmin = 0.961, Tmax = 0.980 | k = −13→12 |
208 measured reflections | l = −13→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.071P)2 + 0.1147P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.002 |
4187 reflections | Δρmax = 0.15 e Å−3 |
298 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.029 (3) |
C13H16O3 | γ = 68.734 (3)° |
Mr = 220.26 | V = 1190.2 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.7647 (17) Å | Mo Kα radiation |
b = 11.347 (2) Å | µ = 0.09 mm−1 |
c = 11.553 (2) Å | T = 293 K |
α = 87.357 (3)° | 0.46 × 0.30 × 0.24 mm |
β = 86.416 (3)° |
Bruker SMART CCD area-detector diffractometer | 4187 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2542 reflections with I > 2σ(I) |
Tmin = 0.961, Tmax = 0.980 | Rint = 0.017 |
208 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.15 e Å−3 |
4187 reflections | Δρmin = −0.14 e Å−3 |
298 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 1.25506 (18) | 0.10599 (15) | −0.12691 (14) | 0.0839 (5) | |
O2 | 1.17852 (16) | −0.00557 (13) | 0.04770 (14) | 0.0714 (5) | |
H2 | 1.2296 | 0.0022 | −0.0091 | 0.107* | |
O3 | 0.75851 (15) | 0.23654 (13) | 0.27682 (12) | 0.0659 (4) | |
O4 | −0.01889 (19) | 0.72134 (16) | 0.50337 (15) | 0.0900 (6) | |
O5 | 0.04455 (16) | 0.82123 (14) | 0.31644 (15) | 0.0806 (5) | |
H5 | −0.0057 | 0.8143 | 0.3741 | 0.121* | |
O6 | 0.51181 (14) | 0.60928 (13) | 0.13071 (12) | 0.0654 (4) | |
C1 | 1.1437 (3) | 0.3223 (2) | −0.1747 (2) | 0.0770 (7) | |
H1A | 1.2193 | 0.3005 | −0.2357 | 0.115* | |
H1B | 1.1555 | 0.3849 | −0.1271 | 0.115* | |
H1C | 1.0490 | 0.3557 | −0.2078 | 0.115* | |
C2 | 1.1552 (2) | 0.2065 (2) | −0.10190 (18) | 0.0607 (6) | |
C3 | 1.0534 (2) | 0.21320 (18) | −0.00314 (17) | 0.0516 (5) | |
C4 | 0.9361 (2) | 0.32489 (19) | 0.02578 (18) | 0.0572 (6) | |
H4 | 0.9228 | 0.3976 | −0.0198 | 0.069* | |
C5 | 0.8411 (2) | 0.33011 (19) | 0.11839 (18) | 0.0588 (6) | |
H5A | 0.7641 | 0.4054 | 0.1355 | 0.071* | |
C6 | 0.8600 (2) | 0.22158 (18) | 0.18756 (17) | 0.0520 (5) | |
C7 | 0.9741 (2) | 0.11066 (18) | 0.16346 (17) | 0.0547 (5) | |
H7 | 0.9874 | 0.0391 | 0.2106 | 0.066* | |
C8 | 1.0694 (2) | 0.10604 (18) | 0.06845 (17) | 0.0527 (5) | |
C9 | 0.7625 (2) | 0.12683 (19) | 0.34593 (19) | 0.0645 (6) | |
H9A | 0.8504 | 0.0962 | 0.3902 | 0.077* | |
H9B | 0.7630 | 0.0597 | 0.2967 | 0.077* | |
C10 | 0.6288 (2) | 0.1659 (2) | 0.4252 (2) | 0.0645 (6) | |
H10 | 0.5470 | 0.2320 | 0.3993 | 0.077* | |
C11 | 0.6145 (2) | 0.1161 (2) | 0.52906 (19) | 0.0606 (6) | |
C12 | 0.7364 (3) | 0.0125 (3) | 0.5836 (2) | 0.0941 (9) | |
H12A | 0.7214 | −0.0660 | 0.5777 | 0.141* | |
H12B | 0.7383 | 0.0301 | 0.6639 | 0.141* | |
H12C | 0.8283 | 0.0065 | 0.5445 | 0.141* | |
C13 | 0.4715 (3) | 0.1616 (3) | 0.5984 (2) | 0.0856 (8) | |
H13A | 0.3992 | 0.2257 | 0.5546 | 0.128* | |
H13B | 0.4844 | 0.1963 | 0.6694 | 0.128* | |
H13C | 0.4391 | 0.0921 | 0.6158 | 0.128* | |
C14 | 0.1377 (3) | 0.5350 (2) | 0.5921 (2) | 0.0778 (7) | |
H14A | 0.0582 | 0.5553 | 0.6498 | 0.117* | |
H14B | 0.2264 | 0.5296 | 0.6273 | 0.117* | |
H14C | 0.1511 | 0.4553 | 0.5590 | 0.117* | |
C15 | 0.1030 (2) | 0.6355 (2) | 0.49938 (19) | 0.0606 (6) | |
C16 | 0.2095 (2) | 0.63136 (18) | 0.40422 (17) | 0.0505 (5) | |
C17 | 0.3488 (2) | 0.53508 (19) | 0.39605 (17) | 0.0560 (5) | |
H17 | 0.3753 | 0.4731 | 0.4546 | 0.067* | |
C18 | 0.4460 (2) | 0.52966 (19) | 0.30523 (18) | 0.0579 (5) | |
H18 | 0.5372 | 0.4642 | 0.3014 | 0.070* | |
C19 | 0.4078 (2) | 0.62322 (18) | 0.21770 (17) | 0.0525 (5) | |
C20 | 0.2732 (2) | 0.71977 (19) | 0.22245 (18) | 0.0577 (6) | |
H20 | 0.2482 | 0.7816 | 0.1637 | 0.069* | |
C21 | 0.1748 (2) | 0.72438 (18) | 0.31532 (18) | 0.0551 (5) | |
C22 | 0.4793 (2) | 0.6982 (2) | 0.03491 (19) | 0.0664 (6) | |
H22A | 0.4695 | 0.7813 | 0.0603 | 0.080* | |
H22B | 0.3876 | 0.7042 | 0.0026 | 0.080* | |
C23 | 0.6022 (2) | 0.6528 (2) | −0.05365 (18) | 0.0615 (6) | |
H23 | 0.6548 | 0.5661 | −0.0546 | 0.074* | |
C24 | 0.6439 (2) | 0.7235 (2) | −0.13107 (17) | 0.0544 (5) | |
C25 | 0.5709 (3) | 0.8638 (2) | −0.1387 (2) | 0.0821 (8) | |
H25A | 0.5021 | 0.8864 | −0.1991 | 0.123* | |
H25B | 0.6438 | 0.9013 | −0.1559 | 0.123* | |
H25C | 0.5198 | 0.8941 | −0.0661 | 0.123* | |
C26 | 0.7666 (2) | 0.6677 (2) | −0.2193 (2) | 0.0732 (7) | |
H26A | 0.8070 | 0.5775 | −0.2077 | 0.110* | |
H26B | 0.8420 | 0.7020 | −0.2112 | 0.110* | |
H26C | 0.7298 | 0.6876 | −0.2957 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0746 (11) | 0.0659 (10) | 0.0822 (11) | 0.0036 (9) | 0.0257 (8) | 0.0058 (8) |
O2 | 0.0646 (10) | 0.0475 (9) | 0.0814 (11) | 0.0004 (7) | 0.0168 (8) | 0.0050 (7) |
O3 | 0.0615 (9) | 0.0509 (9) | 0.0721 (10) | −0.0094 (7) | 0.0206 (8) | 0.0070 (7) |
O4 | 0.0756 (11) | 0.0713 (11) | 0.0987 (13) | −0.0046 (9) | 0.0356 (9) | 0.0059 (9) |
O5 | 0.0588 (10) | 0.0567 (10) | 0.1004 (13) | 0.0034 (8) | 0.0214 (8) | 0.0182 (8) |
O6 | 0.0519 (8) | 0.0619 (9) | 0.0695 (10) | −0.0094 (7) | 0.0118 (7) | 0.0138 (7) |
C1 | 0.0809 (16) | 0.0691 (16) | 0.0713 (15) | −0.0202 (13) | 0.0160 (12) | 0.0107 (12) |
C2 | 0.0568 (13) | 0.0573 (13) | 0.0577 (13) | −0.0102 (11) | 0.0054 (10) | 0.0039 (10) |
C3 | 0.0497 (12) | 0.0462 (12) | 0.0522 (12) | −0.0100 (9) | 0.0005 (9) | 0.0022 (9) |
C4 | 0.0573 (13) | 0.0445 (12) | 0.0597 (13) | −0.0084 (10) | 0.0029 (10) | 0.0088 (9) |
C5 | 0.0518 (12) | 0.0461 (12) | 0.0633 (13) | −0.0014 (10) | 0.0063 (10) | 0.0028 (10) |
C6 | 0.0481 (11) | 0.0480 (12) | 0.0541 (12) | −0.0118 (10) | 0.0036 (9) | 0.0031 (9) |
C7 | 0.0544 (12) | 0.0444 (12) | 0.0595 (13) | −0.0129 (10) | 0.0017 (10) | 0.0076 (9) |
C8 | 0.0460 (11) | 0.0430 (11) | 0.0601 (13) | −0.0057 (9) | 0.0001 (10) | 0.0002 (10) |
C9 | 0.0630 (14) | 0.0513 (13) | 0.0726 (15) | −0.0159 (11) | 0.0108 (11) | 0.0086 (11) |
C10 | 0.0568 (13) | 0.0524 (13) | 0.0785 (16) | −0.0151 (10) | 0.0098 (11) | 0.0010 (11) |
C11 | 0.0680 (14) | 0.0502 (12) | 0.0647 (14) | −0.0248 (11) | 0.0150 (11) | −0.0093 (10) |
C12 | 0.103 (2) | 0.0880 (19) | 0.0765 (17) | −0.0208 (16) | 0.0077 (15) | 0.0158 (15) |
C13 | 0.0884 (18) | 0.0832 (18) | 0.0893 (18) | −0.0396 (15) | 0.0300 (15) | −0.0158 (14) |
C14 | 0.0823 (17) | 0.0787 (16) | 0.0653 (15) | −0.0247 (13) | 0.0141 (12) | 0.0080 (13) |
C15 | 0.0632 (14) | 0.0516 (13) | 0.0637 (14) | −0.0184 (11) | 0.0113 (11) | −0.0078 (10) |
C16 | 0.0537 (12) | 0.0411 (11) | 0.0565 (12) | −0.0175 (9) | 0.0031 (9) | −0.0035 (9) |
C17 | 0.0567 (13) | 0.0490 (12) | 0.0571 (13) | −0.0137 (10) | −0.0015 (10) | 0.0053 (10) |
C18 | 0.0462 (12) | 0.0504 (12) | 0.0667 (14) | −0.0065 (10) | 0.0017 (10) | 0.0050 (10) |
C19 | 0.0463 (12) | 0.0494 (12) | 0.0591 (13) | −0.0156 (10) | 0.0059 (10) | 0.0010 (10) |
C20 | 0.0545 (13) | 0.0474 (12) | 0.0647 (13) | −0.0134 (10) | 0.0054 (10) | 0.0090 (10) |
C21 | 0.0493 (12) | 0.0409 (11) | 0.0681 (14) | −0.0097 (9) | 0.0069 (10) | 0.0013 (10) |
C22 | 0.0574 (13) | 0.0638 (14) | 0.0688 (14) | −0.0147 (11) | 0.0092 (11) | 0.0131 (11) |
C23 | 0.0564 (13) | 0.0536 (13) | 0.0652 (14) | −0.0107 (10) | 0.0079 (10) | 0.0005 (11) |
C24 | 0.0454 (11) | 0.0598 (13) | 0.0532 (12) | −0.0142 (10) | 0.0037 (9) | −0.0016 (10) |
C25 | 0.0835 (17) | 0.0684 (16) | 0.0835 (17) | −0.0186 (13) | 0.0140 (13) | 0.0111 (13) |
C26 | 0.0632 (14) | 0.0838 (17) | 0.0679 (15) | −0.0226 (12) | 0.0126 (11) | −0.0094 (12) |
O1—C2 | 1.234 (2) | C12—H12B | 0.9600 |
O2—C8 | 1.347 (2) | C12—H12C | 0.9600 |
O2—H2 | 0.8200 | C13—H13A | 0.9600 |
O3—C6 | 1.357 (2) | C13—H13B | 0.9600 |
O3—C9 | 1.437 (2) | C13—H13C | 0.9600 |
O4—C15 | 1.234 (2) | C14—C15 | 1.488 (3) |
O5—C21 | 1.346 (2) | C14—H14A | 0.9600 |
O5—H5 | 0.8200 | C14—H14B | 0.9600 |
O6—C19 | 1.355 (2) | C14—H14C | 0.9600 |
O6—C22 | 1.433 (2) | C15—C16 | 1.456 (3) |
C1—C2 | 1.500 (3) | C16—C17 | 1.402 (3) |
C1—H1A | 0.9600 | C16—C21 | 1.403 (3) |
C1—H1B | 0.9600 | C17—C18 | 1.358 (3) |
C1—H1C | 0.9600 | C17—H17 | 0.9300 |
C2—C3 | 1.451 (3) | C18—C19 | 1.396 (3) |
C3—C4 | 1.403 (3) | C18—H18 | 0.9300 |
C3—C8 | 1.404 (3) | C19—C20 | 1.373 (3) |
C4—C5 | 1.360 (3) | C20—C21 | 1.384 (3) |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—C6 | 1.397 (3) | C22—C23 | 1.483 (3) |
C5—H5A | 0.9300 | C22—H22A | 0.9700 |
C6—C7 | 1.371 (3) | C22—H22B | 0.9700 |
C7—C8 | 1.384 (3) | C23—C24 | 1.318 (3) |
C7—H7 | 0.9300 | C23—H23 | 0.9300 |
C9—C10 | 1.486 (3) | C24—C25 | 1.491 (3) |
C9—H9A | 0.9700 | C24—C26 | 1.494 (3) |
C9—H9B | 0.9700 | C25—H25A | 0.9600 |
C10—C11 | 1.324 (3) | C25—H25B | 0.9600 |
C10—H10 | 0.9300 | C25—H25C | 0.9600 |
C11—C12 | 1.485 (3) | C26—H26A | 0.9600 |
C11—C13 | 1.495 (3) | C26—H26B | 0.9600 |
C12—H12A | 0.9600 | C26—H26C | 0.9600 |
C8—O2—H2 | 109.5 | H13A—C13—H13C | 109.5 |
C6—O3—C9 | 118.25 (15) | H13B—C13—H13C | 109.5 |
C21—O5—H5 | 109.5 | C15—C14—H14A | 109.5 |
C19—O6—C22 | 118.66 (15) | C15—C14—H14B | 109.5 |
C2—C1—H1A | 109.5 | H14A—C14—H14B | 109.5 |
C2—C1—H1B | 109.5 | C15—C14—H14C | 109.5 |
H1A—C1—H1B | 109.5 | H14A—C14—H14C | 109.5 |
C2—C1—H1C | 109.5 | H14B—C14—H14C | 109.5 |
H1A—C1—H1C | 109.5 | O4—C15—C16 | 120.5 (2) |
H1B—C1—H1C | 109.5 | O4—C15—C14 | 118.85 (19) |
O1—C2—C3 | 120.95 (19) | C16—C15—C14 | 120.68 (19) |
O1—C2—C1 | 118.25 (19) | C17—C16—C21 | 117.23 (18) |
C3—C2—C1 | 120.79 (18) | C17—C16—C15 | 122.26 (19) |
C4—C3—C8 | 116.95 (18) | C21—C16—C15 | 120.50 (18) |
C4—C3—C2 | 122.47 (19) | C18—C17—C16 | 121.97 (19) |
C8—C3—C2 | 120.59 (18) | C18—C17—H17 | 119.0 |
C5—C4—C3 | 122.01 (19) | C16—C17—H17 | 119.0 |
C5—C4—H4 | 119.0 | C17—C18—C19 | 119.44 (18) |
C3—C4—H4 | 119.0 | C17—C18—H18 | 120.3 |
C4—C5—C6 | 119.53 (18) | C19—C18—H18 | 120.3 |
C4—C5—H5A | 120.2 | O6—C19—C20 | 124.36 (18) |
C6—C5—H5A | 120.2 | O6—C19—C18 | 115.01 (17) |
O3—C6—C7 | 124.63 (18) | C20—C19—C18 | 120.62 (18) |
O3—C6—C5 | 114.84 (17) | C19—C20—C21 | 119.49 (19) |
C7—C6—C5 | 120.53 (18) | C19—C20—H20 | 120.3 |
C6—C7—C8 | 119.50 (19) | C21—C20—H20 | 120.3 |
C6—C7—H7 | 120.3 | O5—C21—C20 | 117.30 (18) |
C8—C7—H7 | 120.3 | O5—C21—C16 | 121.47 (18) |
O2—C8—C7 | 117.16 (18) | C20—C21—C16 | 121.23 (18) |
O2—C8—C3 | 121.35 (17) | O6—C22—C23 | 107.71 (17) |
C7—C8—C3 | 121.49 (18) | O6—C22—H22A | 110.2 |
O3—C9—C10 | 106.99 (17) | C23—C22—H22A | 110.2 |
O3—C9—H9A | 110.3 | O6—C22—H22B | 110.2 |
C10—C9—H9A | 110.3 | C23—C22—H22B | 110.2 |
O3—C9—H9B | 110.3 | H22A—C22—H22B | 108.5 |
C10—C9—H9B | 110.3 | C24—C23—C22 | 126.2 (2) |
H9A—C9—H9B | 108.6 | C24—C23—H23 | 116.9 |
C11—C10—C9 | 126.5 (2) | C22—C23—H23 | 116.9 |
C11—C10—H10 | 116.7 | C23—C24—C25 | 122.78 (19) |
C9—C10—H10 | 116.7 | C23—C24—C26 | 121.9 (2) |
C10—C11—C12 | 123.0 (2) | C25—C24—C26 | 115.28 (19) |
C10—C11—C13 | 121.1 (2) | C24—C25—H25A | 109.5 |
C12—C11—C13 | 115.9 (2) | C24—C25—H25B | 109.5 |
C11—C12—H12A | 109.5 | H25A—C25—H25B | 109.5 |
C11—C12—H12B | 109.5 | C24—C25—H25C | 109.5 |
H12A—C12—H12B | 109.5 | H25A—C25—H25C | 109.5 |
C11—C12—H12C | 109.5 | H25B—C25—H25C | 109.5 |
H12A—C12—H12C | 109.5 | C24—C26—H26A | 109.5 |
H12B—C12—H12C | 109.5 | C24—C26—H26B | 109.5 |
C11—C13—H13A | 109.5 | H26A—C26—H26B | 109.5 |
C11—C13—H13B | 109.5 | C24—C26—H26C | 109.5 |
H13A—C13—H13B | 109.5 | H26A—C26—H26C | 109.5 |
C11—C13—H13C | 109.5 | H26B—C26—H26C | 109.5 |
O1—C2—C3—C4 | −178.1 (2) | O4—C15—C16—C17 | −179.6 (2) |
C1—C2—C3—C4 | 3.3 (3) | C14—C15—C16—C17 | −0.9 (3) |
O1—C2—C3—C8 | 2.1 (3) | O4—C15—C16—C21 | −0.5 (3) |
C1—C2—C3—C8 | −176.5 (2) | C14—C15—C16—C21 | 178.3 (2) |
C8—C3—C4—C5 | −0.3 (3) | C21—C16—C17—C18 | −1.2 (3) |
C2—C3—C4—C5 | 179.8 (2) | C15—C16—C17—C18 | 178.0 (2) |
C3—C4—C5—C6 | 0.1 (3) | C16—C17—C18—C19 | 0.8 (3) |
C9—O3—C6—C7 | −5.3 (3) | C22—O6—C19—C20 | −2.0 (3) |
C9—O3—C6—C5 | 174.66 (19) | C22—O6—C19—C18 | 177.42 (19) |
C4—C5—C6—O3 | −179.31 (18) | C17—C18—C19—O6 | −179.76 (19) |
C4—C5—C6—C7 | 0.7 (3) | C17—C18—C19—C20 | −0.4 (3) |
O3—C6—C7—C8 | 178.76 (18) | O6—C19—C20—C21 | 179.64 (19) |
C5—C6—C7—C8 | −1.2 (3) | C18—C19—C20—C21 | 0.3 (3) |
C6—C7—C8—O2 | −179.17 (19) | C19—C20—C21—O5 | 179.63 (19) |
C6—C7—C8—C3 | 1.0 (3) | C19—C20—C21—C16 | −0.7 (3) |
C4—C3—C8—O2 | 179.93 (19) | C17—C16—C21—O5 | −179.22 (19) |
C2—C3—C8—O2 | −0.2 (3) | C15—C16—C21—O5 | 1.6 (3) |
C4—C3—C8—C7 | −0.3 (3) | C17—C16—C21—C20 | 1.1 (3) |
C2—C3—C8—C7 | 179.59 (19) | C15—C16—C21—C20 | −178.05 (19) |
C6—O3—C9—C10 | −172.10 (18) | C19—O6—C22—C23 | −173.05 (18) |
O3—C9—C10—C11 | −151.6 (2) | O6—C22—C23—C24 | −153.2 (2) |
C9—C10—C11—C12 | 1.7 (4) | C22—C23—C24—C25 | 0.7 (4) |
C9—C10—C11—C13 | −177.8 (2) | C22—C23—C24—C26 | −178.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.82 | 1.82 | 2.548 (2) | 147 |
O5—H5···O4 | 0.82 | 1.81 | 2.539 (2) | 147 |
Experimental details
Crystal data | |
Chemical formula | C13H16O3 |
Mr | 220.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.7647 (17), 11.347 (2), 11.553 (2) |
α, β, γ (°) | 87.357 (3), 86.416 (3), 68.734 (3) |
V (Å3) | 1190.2 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.46 × 0.30 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.961, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 208, 4187, 2542 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.142, 1.01 |
No. of reflections | 4187 |
No. of parameters | 298 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.14 |
Computer programs: SAINT (Bruker, 1997), SMART (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.82 | 1.82 | 2.548 (2) | 146.6 |
O5—H5···O4 | 0.82 | 1.81 | 2.539 (2) | 146.7 |
Sofalcone is an antiulcer agent which is effective for the treatment of gastric ulcer (Kazuaki & Katsuo, 1979). A smiliar structure, ethyl 2- [2-acetyl-5-(3-methylbut-2-enyloxy)phenoxy]acetate (Zhang et al., 2007), has been reported. Now, we present the crystal structure of the title compound.
The asymmetric unit of the title compound, (I), contains two independent molecules. In the two molecules, all O atoms don't significantly deviate from the benzene ring planar with r.m.s. deviations of 0.0103 (2) and 0.0114 (2) Å, repectively. Due to the p-π conjugation, the Csp2—O bonds [O3—C6 = 1.357 (2) Å and O6—C19 = 1.355 (2) Å] are significantly shorter than the Csp3—O bonds [O3—C9 = 1.437 (2) Å and O6—C22 = 1.433 (2) Å]. Intermolecular O—H···O hydrogen bonds (Table 1) are formed between the carbonyl and hydroxyl groups, which stabilize the crystal struture.