organic compounds
7-Hydroxy-4-methyl-8-(3-methylbenzoyl)-2H-chromen-2-one ethanol monosolvate
aCollege of Chemical Engineering, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China, and bCollege of Mathematics and Science, Huaihai Institute of Technology, Lianyungang 222005, People's Republic of China
*Correspondence e-mail: spyang69320@yahoo.cn
In the title compound, C18H14O4·C2H6O, the coumarin ring system is approximately planar with a maximum deviation of 0.037 (3) Å and is nearly perpendicular to the benzene ring, making a dihedral angle of 86.55 (9)°. In the crystal, molecules are linked by classical O—H⋯O hydrogen bonds and weak C—H⋯O interactions.
Related literature
For the biological activity of et al. (2005); Xiao et al. (2010); Iqbal et al. (2009); Siddiqui et al. (2009); Rollinger et al. (2004); Brühlmann et al. (2001). For a related structure, see: Yang et al. (2010).
see: SharmaExperimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536811046630/xu5373sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046630/xu5373Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811046630/xu5373Isup3.cml
The mixture containing 1.47 g (5 mmol) of dry powdered 7-(3-methylbenzoxy)-4-methylcoumarin and 2.0 g (15 mmol) of anhydrous aluminium chloride was heated for about 2 h at 463 K in an oil bath, then 30 ml of dilute (1:7) hydrochloric acid is added and the mixture is heated on a steam bath for 60 min, the crude products were filtered off, washed with water. Single crystals of (I) suitable for X-ray structure analysis were obtained by recrystallizing the crude product from a 95% ethanol solution, m.p. 503–504 K.
H atoms were placed in calculated positions with O—H = 0.82 Å (hydroxyl), C—H = 0.93 (aromatic), 0.96 (methyl) and 0.97 Å (methylene), and refined in riding mode with Uiso(H) = 1.2Ueq(C) (aromatic and methylene) and Uiso(H) = 1.5Ueq(C,O) (methyl and hydroxyl).
Coumarins are very well known for their biological activity, such as antioxidants (Sharma et al., 2005), anticancer activity (Xiao et al., 2010), antiamoebic (Iqbal et al., 2009), anticonvulsant activity (Siddiqui et al., 2009) and inhibitions of acetylcholinesterase and monoamine oxidase (Rollinger et al., 2004; Brühlmann et al., 2001). Previous we have decribed the
of 8-benzoyl-7-hydroxy-4-methyl coumarin (Yang et al., 2010). As part of our study of the crystal structures of coumarin derivatives with 7-hydroxy, we report here the of 8-(3-methylbenzoyl)-7-hydroxy-4-methyl-2H-1-benzopyran-2-one, (I).In the molecule (I), the
contains one coumarin molecule and one ethanol molecule, and which are linked together by one O—H···O hydrogen bond (Table 1 and Fig. 1). The coumarin moiety (r.m.s deviations 0.0214 Å) and phenyl ring are perpendicular to each other with a dihedral angle of 86.55 (9)° between the plane of the atoms O1—O3/C1—C9 and the plane of C12—C17.In π–π interaction, the ring centroid Cg1[O1/C1—C4/C9] in the molecule at (x, y, z) connects Cg1 in the molecule at (1 - x, 1 - y, 1 - z) [centroid–centroid distance = 3.57278 (17) Å], so forming a doubled chain of R44(22) ring parallel to the [010] direction (Fig. 2). Neighboring doubled chains are linked into three-dimensional by weak C—H···O hydrogen bonds (Table.1).
of (I), atom O3 in the molecule at (x, y, z) acts as hydrogen bond donor to atom O5 in the molecule at (x, y - 1, z), forming a C(10) chain running parallel to the [010] direction and generated by translation. Inversionally related molecular chains are linked together by a weakFor the biological activity of
see: Sharma et al. (2005); Xiao et al. (2010); Iqbal et al. (2009); Siddiqui et al. (2009); Rollinger et al. (2004); Brühlmann et al. (2001). For a related structure, see: Yang et al. (2010).Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C18H14O4·C2H6O | F(000) = 720 |
Mr = 340.36 | Dx = 1.309 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1087 reflections |
a = 12.4562 (6) Å | θ = 2.5–27.8° |
b = 10.0341 (5) Å | µ = 0.09 mm−1 |
c = 14.8999 (7) Å | T = 298 K |
β = 111.980 (3)° | Prism, colourless |
V = 1726.93 (14) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 3021 independent reflections |
Radiation source: fine-focus sealed tube | 1762 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.119 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −14→8 |
Tmin = 0.972, Tmax = 0.982 | k = −11→8 |
12216 measured reflections | l = −15→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0767P)2 + 0.8164P] where P = (Fo2 + 2Fc2)/3 |
3021 reflections | (Δ/σ)max < 0.001 |
229 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C18H14O4·C2H6O | V = 1726.93 (14) Å3 |
Mr = 340.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.4562 (6) Å | µ = 0.09 mm−1 |
b = 10.0341 (5) Å | T = 298 K |
c = 14.8999 (7) Å | 0.30 × 0.25 × 0.20 mm |
β = 111.980 (3)° |
Bruker APEXII CCD area-detector diffractometer | 3021 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1762 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.982 | Rint = 0.119 |
12216 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.188 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.19 e Å−3 |
3021 reflections | Δρmin = −0.25 e Å−3 |
229 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 | ||
C1 | 0.5042 (3) | 0.6046 (3) | 0.3838 (2) | 0.0487 (8) | |
C2 | 0.3975 (3) | 0.5458 (3) | 0.3794 (2) | 0.0547 (9) | |
H2 | 0.3386 | 0.6016 | 0.3809 | 0.066* | |
C3 | 0.3789 (3) | 0.4140 (3) | 0.3734 (2) | 0.0498 (8) | |
C4 | 0.4702 (2) | 0.3271 (3) | 0.3715 (2) | 0.0439 (7) | |
C5 | 0.4632 (3) | 0.1883 (3) | 0.3652 (2) | 0.0538 (8) | |
H5 | 0.3943 | 0.1467 | 0.3595 | 0.065* | |
C6 | 0.5548 (3) | 0.1119 (3) | 0.3673 (2) | 0.0523 (8) | |
H6 | 0.5474 | 0.0197 | 0.3626 | 0.063* | |
C7 | 0.6596 (3) | 0.1722 (3) | 0.3765 (2) | 0.0460 (8) | |
C8 | 0.6708 (2) | 0.3099 (3) | 0.38248 (19) | 0.0395 (7) | |
C9 | 0.5751 (2) | 0.3841 (3) | 0.37894 (18) | 0.0400 (7) | |
C10 | 0.2669 (3) | 0.3553 (4) | 0.3712 (3) | 0.0717 (11) | |
H10A | 0.2202 | 0.4242 | 0.3828 | 0.108* | |
H10B | 0.2828 | 0.2882 | 0.4205 | 0.108* | |
H10C | 0.2261 | 0.3159 | 0.3090 | 0.108* | |
C11 | 0.7839 (2) | 0.3780 (3) | 0.3970 (2) | 0.0409 (7) | |
C12 | 0.8089 (2) | 0.4124 (3) | 0.31036 (19) | 0.0389 (7) | |
C13 | 0.9089 (2) | 0.4854 (3) | 0.3207 (2) | 0.0445 (7) | |
H13 | 0.9614 | 0.5062 | 0.3823 | 0.053* | |
C14 | 0.9305 (3) | 0.5269 (3) | 0.2408 (2) | 0.0524 (8) | |
C15 | 0.8528 (3) | 0.4895 (4) | 0.1505 (3) | 0.0639 (10) | |
H15 | 0.8668 | 0.5149 | 0.0959 | 0.077* | |
C16 | 0.7554 (3) | 0.4160 (4) | 0.1391 (2) | 0.0637 (10) | |
H16 | 0.7050 | 0.3917 | 0.0775 | 0.076* | |
C17 | 0.7327 (3) | 0.3784 (3) | 0.2191 (2) | 0.0489 (8) | |
H17 | 0.6661 | 0.3301 | 0.2115 | 0.059* | |
C18 | 1.0332 (3) | 0.6147 (4) | 0.2514 (3) | 0.0744 (11) | |
H18A | 1.0066 | 0.7024 | 0.2278 | 0.112* | |
H18B | 1.0751 | 0.5776 | 0.2147 | 0.112* | |
H18C | 1.0833 | 0.6197 | 0.3184 | 0.112* | |
O1 | 0.59052 (16) | 0.51973 (19) | 0.38378 (14) | 0.0455 (5) | |
O2 | 0.52656 (19) | 0.7229 (2) | 0.38776 (17) | 0.0622 (7) | |
O3 | 0.75312 (19) | 0.1018 (2) | 0.37973 (17) | 0.0611 (6) | |
H3 | 0.7378 | 0.0220 | 0.3759 | 0.092* | |
O4 | 0.84811 (18) | 0.4066 (2) | 0.47834 (15) | 0.0611 (7) | |
C19 | 0.8207 (4) | 0.7597 (4) | 0.4184 (4) | 0.0976 (15) | |
H19A | 0.8036 | 0.6926 | 0.3680 | 0.117* | |
H19B | 0.8307 | 0.7144 | 0.4785 | 0.117* | |
C20 | 0.9288 (4) | 0.8253 (4) | 0.4285 (4) | 0.0938 (14) | |
H20A | 0.9239 | 0.8584 | 0.3667 | 0.141* | |
H20B | 0.9914 | 0.7626 | 0.4523 | 0.141* | |
H20C | 0.9425 | 0.8981 | 0.4732 | 0.141* | |
O5 | 0.7296 (2) | 0.8436 (2) | 0.3963 (3) | 0.1013 (11) | |
H5A | 0.6743 | 0.8040 | 0.4008 | 0.152* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0388 (18) | 0.049 (2) | 0.0555 (19) | 0.0084 (15) | 0.0140 (14) | 0.0061 (15) |
C2 | 0.0376 (18) | 0.060 (2) | 0.065 (2) | 0.0087 (16) | 0.0180 (15) | 0.0060 (17) |
C3 | 0.0358 (17) | 0.062 (2) | 0.0499 (18) | −0.0011 (16) | 0.0140 (13) | 0.0072 (15) |
C4 | 0.0359 (16) | 0.049 (2) | 0.0452 (17) | −0.0037 (14) | 0.0129 (13) | 0.0039 (14) |
C5 | 0.0417 (18) | 0.058 (2) | 0.061 (2) | −0.0136 (16) | 0.0182 (15) | 0.0034 (16) |
C6 | 0.052 (2) | 0.0435 (19) | 0.062 (2) | −0.0063 (16) | 0.0216 (16) | 0.0020 (15) |
C7 | 0.0421 (18) | 0.0450 (19) | 0.0511 (18) | 0.0015 (15) | 0.0177 (14) | 0.0041 (14) |
C8 | 0.0384 (16) | 0.0392 (17) | 0.0408 (16) | −0.0007 (13) | 0.0148 (12) | 0.0016 (13) |
C9 | 0.0401 (17) | 0.0388 (17) | 0.0398 (15) | −0.0019 (14) | 0.0135 (13) | 0.0038 (13) |
C10 | 0.041 (2) | 0.085 (3) | 0.092 (3) | −0.0007 (19) | 0.0287 (18) | 0.011 (2) |
C11 | 0.0358 (16) | 0.0378 (17) | 0.0459 (17) | 0.0044 (13) | 0.0117 (14) | 0.0010 (13) |
C12 | 0.0319 (15) | 0.0361 (16) | 0.0486 (16) | 0.0030 (13) | 0.0149 (13) | −0.0006 (13) |
C13 | 0.0358 (16) | 0.0409 (18) | 0.0566 (18) | 0.0009 (13) | 0.0170 (14) | −0.0052 (14) |
C14 | 0.050 (2) | 0.0468 (19) | 0.069 (2) | 0.0021 (15) | 0.0332 (17) | 0.0032 (16) |
C15 | 0.067 (2) | 0.075 (3) | 0.060 (2) | 0.004 (2) | 0.0343 (19) | 0.0069 (18) |
C16 | 0.058 (2) | 0.083 (3) | 0.0475 (19) | −0.005 (2) | 0.0169 (16) | −0.0057 (17) |
C17 | 0.0451 (18) | 0.0514 (19) | 0.0493 (18) | −0.0030 (15) | 0.0167 (14) | −0.0027 (14) |
C18 | 0.063 (2) | 0.071 (3) | 0.103 (3) | −0.010 (2) | 0.048 (2) | 0.005 (2) |
O1 | 0.0357 (11) | 0.0407 (12) | 0.0602 (13) | 0.0028 (9) | 0.0179 (10) | 0.0051 (9) |
O2 | 0.0485 (14) | 0.0451 (14) | 0.0929 (18) | 0.0074 (11) | 0.0262 (12) | 0.0043 (12) |
O3 | 0.0509 (14) | 0.0423 (13) | 0.0938 (17) | 0.0020 (11) | 0.0314 (12) | −0.0004 (12) |
O4 | 0.0472 (14) | 0.0809 (17) | 0.0482 (13) | −0.0111 (12) | 0.0098 (11) | −0.0003 (11) |
C19 | 0.097 (3) | 0.059 (3) | 0.171 (5) | 0.012 (3) | 0.088 (3) | 0.017 (3) |
C20 | 0.071 (3) | 0.081 (3) | 0.131 (4) | 0.006 (2) | 0.040 (3) | −0.009 (3) |
O5 | 0.0615 (17) | 0.0419 (15) | 0.203 (3) | 0.0025 (13) | 0.052 (2) | 0.0129 (17) |
C1—O2 | 1.216 (4) | C12—C17 | 1.379 (4) |
C1—O1 | 1.372 (4) | C12—C13 | 1.403 (4) |
C1—C2 | 1.433 (4) | C13—C14 | 1.379 (4) |
C2—C3 | 1.340 (4) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C15 | 1.384 (5) |
C3—C4 | 1.441 (4) | C14—C18 | 1.512 (4) |
C3—C10 | 1.503 (4) | C15—C16 | 1.375 (5) |
C4—C9 | 1.393 (4) | C15—H15 | 0.9300 |
C4—C5 | 1.397 (4) | C16—C17 | 1.376 (4) |
C5—C6 | 1.364 (4) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | C17—H17 | 0.9300 |
C6—C7 | 1.399 (4) | C18—H18A | 0.9600 |
C6—H6 | 0.9300 | C18—H18B | 0.9600 |
C7—O3 | 1.348 (3) | C18—H18C | 0.9600 |
C7—C8 | 1.387 (4) | O3—H3 | 0.8200 |
C8—C9 | 1.390 (4) | C19—O5 | 1.352 (5) |
C8—C11 | 1.507 (4) | C19—C20 | 1.454 (6) |
C9—O1 | 1.372 (3) | C19—H19A | 0.9700 |
C10—H10A | 0.9600 | C19—H19B | 0.9700 |
C10—H10B | 0.9600 | C20—H20A | 0.9600 |
C10—H10C | 0.9600 | C20—H20B | 0.9600 |
C11—O4 | 1.211 (3) | C20—H20C | 0.9600 |
C11—C12 | 1.478 (4) | O5—H5A | 0.8200 |
O2—C1—O1 | 116.1 (3) | C13—C12—C11 | 119.7 (2) |
O2—C1—C2 | 126.6 (3) | C14—C13—C12 | 121.0 (3) |
O1—C1—C2 | 117.3 (3) | C14—C13—H13 | 119.5 |
C3—C2—C1 | 122.9 (3) | C12—C13—H13 | 119.5 |
C3—C2—H2 | 118.5 | C13—C14—C15 | 117.8 (3) |
C1—C2—H2 | 118.5 | C13—C14—C18 | 121.1 (3) |
C2—C3—C4 | 118.7 (3) | C15—C14—C18 | 121.1 (3) |
C2—C3—C10 | 121.6 (3) | C16—C15—C14 | 122.0 (3) |
C4—C3—C10 | 119.7 (3) | C16—C15—H15 | 119.0 |
C9—C4—C5 | 116.6 (3) | C14—C15—H15 | 119.0 |
C9—C4—C3 | 118.3 (3) | C15—C16—C17 | 119.8 (3) |
C5—C4—C3 | 125.1 (3) | C15—C16—H16 | 120.1 |
C6—C5—C4 | 121.9 (3) | C17—C16—H16 | 120.1 |
C6—C5—H5 | 119.0 | C16—C17—C12 | 119.8 (3) |
C4—C5—H5 | 119.0 | C16—C17—H17 | 120.1 |
C5—C6—C7 | 120.1 (3) | C12—C17—H17 | 120.1 |
C5—C6—H6 | 120.0 | C14—C18—H18A | 109.5 |
C7—C6—H6 | 120.0 | C14—C18—H18B | 109.5 |
O3—C7—C8 | 117.1 (3) | H18A—C18—H18B | 109.5 |
O3—C7—C6 | 122.6 (3) | C14—C18—H18C | 109.5 |
C8—C7—C6 | 120.3 (3) | H18A—C18—H18C | 109.5 |
C7—C8—C9 | 117.9 (3) | H18B—C18—H18C | 109.5 |
C7—C8—C11 | 121.8 (3) | C1—O1—C9 | 121.4 (2) |
C9—C8—C11 | 120.3 (2) | C7—O3—H3 | 109.5 |
O1—C9—C8 | 115.4 (2) | O5—C19—C20 | 113.8 (3) |
O1—C9—C4 | 121.3 (3) | O5—C19—H19A | 108.8 |
C8—C9—C4 | 123.3 (3) | C20—C19—H19A | 108.8 |
C3—C10—H10A | 109.5 | O5—C19—H19B | 108.8 |
C3—C10—H10B | 109.5 | C20—C19—H19B | 108.8 |
H10A—C10—H10B | 109.5 | H19A—C19—H19B | 107.7 |
C3—C10—H10C | 109.5 | C19—C20—H20A | 109.5 |
H10A—C10—H10C | 109.5 | C19—C20—H20B | 109.5 |
H10B—C10—H10C | 109.5 | H20A—C20—H20B | 109.5 |
O4—C11—C12 | 122.8 (3) | C19—C20—H20C | 109.5 |
O4—C11—C8 | 118.9 (2) | H20A—C20—H20C | 109.5 |
C12—C11—C8 | 118.2 (2) | H20B—C20—H20C | 109.5 |
C17—C12—C13 | 119.5 (3) | C19—O5—H5A | 109.5 |
C17—C12—C11 | 120.7 (3) | ||
O2—C1—C2—C3 | 178.8 (3) | C3—C4—C9—C8 | 176.9 (3) |
O1—C1—C2—C3 | −1.5 (4) | C7—C8—C11—O4 | −94.5 (3) |
C1—C2—C3—C4 | 0.2 (5) | C9—C8—C11—O4 | 82.6 (3) |
C1—C2—C3—C10 | 178.6 (3) | C7—C8—C11—C12 | 88.2 (3) |
C2—C3—C4—C9 | 1.9 (4) | C9—C8—C11—C12 | −94.7 (3) |
C10—C3—C4—C9 | −176.5 (3) | O4—C11—C12—C17 | −179.6 (3) |
C2—C3—C4—C5 | −179.9 (3) | C8—C11—C12—C17 | −2.4 (4) |
C10—C3—C4—C5 | 1.7 (4) | O4—C11—C12—C13 | −2.3 (4) |
C9—C4—C5—C6 | 0.7 (4) | C8—C11—C12—C13 | 174.8 (2) |
C3—C4—C5—C6 | −177.6 (3) | C17—C12—C13—C14 | 1.8 (4) |
C4—C5—C6—C7 | 0.4 (5) | C11—C12—C13—C14 | −175.5 (3) |
C5—C6—C7—O3 | 179.5 (3) | C12—C13—C14—C15 | −2.6 (4) |
C5—C6—C7—C8 | −0.8 (4) | C12—C13—C14—C18 | 175.2 (3) |
O3—C7—C8—C9 | 179.8 (2) | C13—C14—C15—C16 | 1.4 (5) |
C6—C7—C8—C9 | 0.0 (4) | C18—C14—C15—C16 | −176.3 (3) |
O3—C7—C8—C11 | −3.1 (4) | C14—C15—C16—C17 | 0.5 (6) |
C6—C7—C8—C11 | 177.2 (3) | C15—C16—C17—C12 | −1.3 (5) |
C7—C8—C9—O1 | −179.1 (2) | C13—C12—C17—C16 | 0.1 (5) |
C11—C8—C9—O1 | 3.6 (3) | C11—C12—C17—C16 | 177.4 (3) |
C7—C8—C9—C4 | 1.2 (4) | O2—C1—O1—C9 | −179.6 (2) |
C11—C8—C9—C4 | −176.1 (2) | C2—C1—O1—C9 | 0.6 (4) |
C5—C4—C9—O1 | 178.8 (2) | C8—C9—O1—C1 | −178.2 (2) |
C3—C4—C9—O1 | −2.8 (4) | C4—C9—O1—C1 | 1.5 (4) |
C5—C4—C9—C8 | −1.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O5i | 0.82 | 1.82 | 2.629 (3) | 166 |
O5—H5A···O2 | 0.82 | 1.95 | 2.764 (3) | 169 |
C17—H17···O2ii | 0.93 | 2.54 | 3.398 (4) | 154 |
C20—H20B···O4iii | 0.96 | 2.53 | 3.489 (5) | 177 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C18H14O4·C2H6O |
Mr | 340.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 12.4562 (6), 10.0341 (5), 14.8999 (7) |
β (°) | 111.980 (3) |
V (Å3) | 1726.93 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.972, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12216, 3021, 1762 |
Rint | 0.119 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.188, 1.05 |
No. of reflections | 3021 |
No. of parameters | 229 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.25 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Berndt, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O5i | 0.82 | 1.82 | 2.629 (3) | 166.4 |
O5—H5A···O2 | 0.82 | 1.95 | 2.764 (3) | 169.4 |
C17—H17···O2ii | 0.93 | 2.54 | 3.398 (4) | 153.7 |
C20—H20B···O4iii | 0.96 | 2.53 | 3.489 (5) | 177.0 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, −y+1, −z+1. |
Acknowledgements
The project was supported by the Natural Science Foundation of Huaihai Institute of Technology, China (No. Z2009019).
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Coumarins are very well known for their biological activity, such as antioxidants (Sharma et al., 2005), anticancer activity (Xiao et al., 2010), antiamoebic (Iqbal et al., 2009), anticonvulsant activity (Siddiqui et al., 2009) and inhibitions of acetylcholinesterase and monoamine oxidase (Rollinger et al., 2004; Brühlmann et al., 2001). Previous we have decribed the crystal structure of 8-benzoyl-7-hydroxy-4-methyl coumarin (Yang et al., 2010). As part of our study of the crystal structures of coumarin derivatives with 7-hydroxy, we report here the crystal structure of 8-(3-methylbenzoyl)-7-hydroxy-4-methyl-2H-1-benzopyran-2-one, (I).
In the molecule (I), the asymmetric unit contains one coumarin molecule and one ethanol molecule, and which are linked together by one O—H···O hydrogen bond (Table 1 and Fig. 1). The coumarin moiety (r.m.s deviations 0.0214 Å) and phenyl ring are perpendicular to each other with a dihedral angle of 86.55 (9)° between the plane of the atoms O1—O3/C1—C9 and the plane of C12—C17.
In crystal structure of (I), atom O3 in the molecule at (x, y, z) acts as hydrogen bond donor to atom O5 in the molecule at (x, y - 1, z), forming a C(10) chain running parallel to the [010] direction and generated by translation. Inversionally related molecular chains are linked together by a weak π–π interaction, the ring centroid Cg1[O1/C1—C4/C9] in the molecule at (x, y, z) connects Cg1 in the molecule at (1 - x, 1 - y, 1 - z) [centroid–centroid distance = 3.57278 (17) Å], so forming a doubled chain of R44(22) ring parallel to the [010] direction (Fig. 2). Neighboring doubled chains are linked into three-dimensional crystal structure by weak C—H···O hydrogen bonds (Table.1).