Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The Diels-Alder reaction between 5-hydroxy-1,4-naphtho­quinone and 5,5-di­methyl-3-vinyl-1,2-cyclo­hexa­dienyl acetate by endo addition gives the title compound, C22H22O5, in 68% yield. This racemic diastereoisomer has the opposite regiochemistry to ochromycinone analogues produced previously and may allow access to a new type of anticancer-active saqua­yamycin analogue.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103013374/ta1412sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103013374/ta1412Isup2.hkl
Contains datablock I

CCDC reference: 219567

Comment top

The results of the low-temperature single-crystal X-ray study as presented in Figs. 1 and 2 and Tables 1 and 2 are consistent with the given formulation, stoichiometry and stereochemistry. Although non-centrosymmetric, the individual crystals are racemic; the asymmetric unit of the structure consists of two independent molecules of similar geometry and conformation, with an interesting pseudosymmetry evident in their packing (Figs. 1 and 2). The fused tetracyclic ring system (ring 'D') has been recorded previously with diverse combinations of hydroxy and keto moieties at the 7,12-sites, with phenol substituents at the 8- rather than the 11-position as in the title compound, and with a diversity of double-bond and/or epoxide functionalities variously associated with rings A and B. A brominated adduct (Rozek et al., 2001) corresponding to the present combination of substituents has also been reported (see Kim et al., 1992; Rozek, Janowski et al., 1998; Rozek, Tiekink et al., 1998; Sasaki et al., 1998.; Apponyi et al., 2002). The combination of ring fusions and functionalities results in a curved/'dished' molecule with dihedral angles between the planes of the double bonds about Cn1—Cn2 and Cn5—Cn6 of 29.7 (1) and 27.7 (2)° (n = 1 or 2), the angles to the aromatic ring being, respectively, 84.8 (2) and 85.8 (2), and 75.6 (1) and 76.6 (1)°; the pendant C2O2 acetate planes are twisted to lie at dihedral angles of 115.4 (2) and 115.3 (2)° to the Cn1—Cn2 environment planes. Hydrogen-bonding details are given in the Table 1. A pronounced asymmetry in the exocyclic angles at Cn11, suggestive of O···O repulsion, is more pronounced than at Cn12 (or Cn7).

Experimental top

A mixture of 5-hydroxy-1,4-naphthoquinone (317 mg) and 5,5-dimethyl- 3-vinyl-1,2-cyclohexadienyl acetate (350 mg) in anhydrous toluene (60 cm3) was heated under reflux for 60 h. The reaction mixture was allowed to cool to 293 K, the solvent was concentrated to 2 ml in vacuo, and the product was precipitated following dropwise addition of diethyl ether at 273 K. The product (550 mg) was purified by flash chromatography on silica eluting with hexane/diethyl ether (2:1) and was crystallized from dichloromethane/diethyl ether (1:1) to yield the title compound (yield 450 mg, 68%) as colourless crystals (m.p. 461–463 K).

Refinement top

H atoms were located from difference Fourier maps and refined without constraints.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: Xtal3.5 (Hall, King, and Stewart, 1995); program(s) used to solve structure: Xtal3.5; program(s) used to refine structure: CRYLSQ in Xtal3.5; molecular graphics: Xtal3.5; software used to prepare material for publication: BONDLA and CIFIO in Xtal3.5.

Figures top
[Figure 1] Fig. 1. The unit cell of (I), projected along b. Displacement ellipsoids for non-H atoms are shown at the 50% probability level.
[Figure 2] Fig. 2. Molecule 1 of (I) (molecule 2 is similar), showing the atomic numbering scheme (molecule numbers, n, have been omitted). H atoms are respresented by circles of arbitrary radii (0.1 Å)..
(I) top
Crystal data top
C22H22O5F(000) = 1552
Mr = 366.41Dx = 1.298 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: c -2ycCell parameters from 6110 reflections
a = 13.774 (2) Åθ = 2.4–20.3°
b = 11.233 (2) ŵ = 0.09 mm1
c = 24.595 (4) ÅT = 153 K
β = 99.792 (2)°Fragment, colourless
V = 3750.0 (11) Å30.32 × 0.21 × 0.17 mm
Z = 8
Data collection top
Bruker SMART CCD
diffractometer
4771 independent reflections
Radiation source: sealed tube4288 reflections with F > 2σ(F)
Graphite monochromatorRint = 0.044
ω scansθmax = 29°, θmin = 2.4°
Absorption correction: multi-scan
SADABS; Sheldrick, 1996
h = 1818
Tmin = 0.87, Tmax = 0.96k = 1515
21857 measured reflectionsl = 3232
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.044All H-atom parameters refined
wR(F2) = 0.046 w = 1/(σ2(F)) + .0005F2)
S = 1.07(Δ/σ)max = 0.016
4288 reflectionsΔρmax = 0.34 e Å3
661 parametersΔρmin = 0.23 e Å3
Crystal data top
C22H22O5V = 3750.0 (11) Å3
Mr = 366.41Z = 8
Monoclinic, CcMo Kα radiation
a = 13.774 (2) ŵ = 0.09 mm1
b = 11.233 (2) ÅT = 153 K
c = 24.595 (4) Å0.32 × 0.21 × 0.17 mm
β = 99.792 (2)°
Data collection top
Bruker SMART CCD
diffractometer
4771 independent reflections
Absorption correction: multi-scan
SADABS; Sheldrick, 1996
4288 reflections with F > 2σ(F)
Tmin = 0.87, Tmax = 0.96Rint = 0.044
21857 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.046All H-atom parameters refined
S = 1.07Δρmax = 0.34 e Å3
4288 reflectionsΔρmin = 0.23 e Å3
661 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.5000 (2)0.5573 (3)0.5000 (2)0.0258 (13)
O110.4053 (2)0.57208 (18)0.51478 (14)0.0305 (10)
C1130.3281 (3)0.5156 (3)0.4840 (2)0.0360 (15)
O1130.3347 (3)0.4559 (2)0.44397 (17)0.0486 (13)
C1140.2349 (3)0.5388 (4)0.5055 (2)0.053 (2)
C120.5688 (3)0.5035 (3)0.53523 (17)0.0287 (14)
C130.6741 (3)0.4918 (3)0.52649 (17)0.0298 (13)
C1310.7357 (3)0.5866 (4)0.56077 (19)0.0399 (18)
C1320.7132 (3)0.3673 (4)0.5445 (2)0.0411 (18)
C140.6780 (3)0.5066 (3)0.46449 (17)0.0300 (14)
C14a0.6193 (3)0.6121 (3)0.43903 (16)0.0267 (13)
C150.6563 (3)0.6956 (3)0.41007 (17)0.0314 (14)
C160.5992 (3)0.7975 (3)0.38152 (17)0.0307 (14)
C16a0.4875 (3)0.7856 (3)0.38058 (16)0.0270 (13)
C170.4392 (3)0.9042 (3)0.36621 (17)0.0284 (13)
O170.4011 (3)0.9285 (2)0.31892 (15)0.0389 (11)
C17a0.4463 (3)0.9924 (3)0.41186 (17)0.0285 (14)
C180.4252 (3)1.1113 (3)0.39901 (18)0.0335 (15)
C190.4363 (3)1.1954 (3)0.44107 (19)0.0375 (16)
C1100.4691 (3)1.1634 (3)0.49534 (19)0.0349 (17)
C1110.4911 (3)1.0443 (3)0.50882 (17)0.0307 (14)
O1110.5240 (3)1.0194 (2)0.56257 (15)0.0361 (11)
C111a0.4785 (3)0.9566 (3)0.46717 (17)0.0253 (13)
C1120.5004 (3)0.8302 (3)0.48126 (17)0.0256 (13)
O1120.5396 (3)0.8009 (2)0.52802 (15)0.0358 (11)
C112a0.4675 (3)0.7392 (3)0.43656 (16)0.0251 (13)
C112b0.5122 (3)0.6140 (2)0.44591 (16)0.0251 (13)
C210.6348 (2)0.3800 (3)0.70856 (13)0.0244 (13)
O210.7300 (2)0.39235 (18)0.69395 (14)0.0282 (10)
C2130.8075 (3)0.3397 (3)0.72689 (17)0.0299 (14)
O2130.8001 (2)0.2835 (2)0.76751 (15)0.0375 (11)
C2140.9006 (3)0.3603 (4)0.7048 (2)0.045 (2)
C220.5671 (3)0.3209 (3)0.67421 (17)0.0269 (13)
C230.4607 (3)0.3111 (3)0.68128 (17)0.0300 (14)
C2310.3988 (3)0.4000 (4)0.6425 (2)0.0426 (18)
C2320.4244 (4)0.1838 (4)0.6682 (2)0.046 (2)
C240.4529 (3)0.3380 (3)0.74182 (17)0.0294 (14)
C24a0.5123 (3)0.4429 (3)0.76629 (16)0.0256 (13)
C250.4757 (3)0.5276 (3)0.79443 (17)0.0290 (14)
C260.5339 (3)0.6291 (3)0.82363 (17)0.0285 (14)
C26a0.6460 (3)0.6145 (3)0.82491 (16)0.0258 (13)
C270.6947 (3)0.7335 (3)0.83866 (17)0.0273 (13)
O270.7332 (3)0.7598 (2)0.88535 (15)0.0369 (11)
C27a0.6875 (3)0.8205 (3)0.79193 (17)0.0260 (13)
C280.7061 (3)0.9399 (3)0.80378 (18)0.0316 (15)
C290.6941 (3)1.0224 (3)0.76085 (19)0.0354 (16)
C2100.6643 (3)0.9872 (3)0.70720 (19)0.0337 (16)
C2110.6452 (3)0.8671 (3)0.69455 (17)0.0281 (13)
O2110.6156 (3)0.8380 (2)0.64116 (14)0.0359 (11)
C211a0.6565 (3)0.7816 (3)0.73703 (17)0.0246 (12)
C2120.6366 (3)0.6542 (3)0.72375 (16)0.0241 (12)
O2120.6004 (3)0.6234 (2)0.67673 (14)0.0325 (11)
C212a0.6668 (3)0.5656 (2)0.76968 (16)0.0226 (12)
C212b0.6205 (3)0.4410 (2)0.76084 (16)0.0241 (13)
H120.555 (2)0.475 (3)0.5691 (15)0.037 (9)*
H131A0.805 (3)0.580 (3)0.5575 (15)0.049 (10)*
H131B0.728 (3)0.574 (3)0.6021 (16)0.049 (11)*
H131C0.720 (3)0.666 (4)0.5476 (17)0.056 (12)*
H132A0.780 (3)0.363 (3)0.5369 (14)0.040 (9)*
H132B0.669 (3)0.301 (4)0.520 (2)0.072 (14)*
H132C0.717 (3)0.357 (4)0.5881 (18)0.059 (12)*
H14A0.643 (3)0.432 (4)0.4466 (17)0.051 (10)*
H14B0.750 (3)0.520 (3)0.4590 (13)0.031 (8)*
H150.726 (3)0.694 (3)0.4062 (14)0.041 (9)*
H16aA0.612 (2)0.805 (3)0.3414 (14)0.033 (9)*
H16B0.625 (3)0.875 (3)0.3996 (15)0.041 (10)*
H16aA0.460 (2)0.730 (3)0.3534 (13)0.022 (7)*
H180.401 (2)1.138 (3)0.3584 (13)0.025 (8)*
H190.418 (3)1.282 (3)0.4304 (15)0.042 (9)*
H1100.474 (3)1.217 (4)0.5235 (17)0.055 (12)*
H1110.540 (4)0.943 (5)0.564 (2)0.086 (17)*
H112A0.401 (2)0.738 (3)0.4378 (12)0.020 (7)*
H112B0.477 (2)0.563 (3)0.4158 (13)0.024 (8)*
H114A0.246 (3)0.576 (4)0.5436 (19)0.057 (12)*
H114B0.203 (4)0.470 (5)0.510 (2)0.079 (16)*
H114C0.190 (5)0.596 (6)0.480 (3)0.15 (3)*
H220.588 (2)0.290 (3)0.6416 (12)0.017 (7)*
H231A0.332 (3)0.387 (4)0.6473 (18)0.067 (13)*
H231B0.403 (3)0.387 (4)0.6013 (18)0.053 (11)*
H231C0.421 (3)0.491 (4)0.6515 (16)0.042 (10)*
H232A0.354 (3)0.172 (3)0.6767 (16)0.058 (12)*
H232B0.466 (4)0.125 (5)0.694 (2)0.096 (19)*
H232C0.427 (3)0.163 (3)0.6301 (18)0.056 (11)*
H24A0.475 (3)0.262 (3)0.7641 (16)0.047 (10)*
H24B0.386 (3)0.344 (3)0.7475 (13)0.031 (8)*
H250.410 (2)0.526 (3)0.7962 (12)0.024 (7)*
H26aA0.525 (3)0.636 (3)0.8622 (15)0.035 (9)*
H26B0.512 (2)0.706 (3)0.8060 (13)0.030 (8)*
H26aA0.671 (2)0.555 (3)0.8541 (14)0.028 (8)*
H280.731 (2)0.970 (3)0.8403 (13)0.023 (7)*
H290.708 (3)1.101 (3)0.7677 (14)0.034 (9)*
H2100.653 (2)1.042 (3)0.6772 (14)0.032 (9)*
H2110.602 (3)0.758 (4)0.6397 (14)0.041 (10)*
H212A0.740 (2)0.556 (3)0.7730 (13)0.030 (8)*
H212B0.653 (2)0.392 (3)0.7933 (13)0.026 (8)*
H214A0.951 (3)0.398 (4)0.7363 (18)0.061 (12)*
H214B0.892 (3)0.397 (4)0.672 (2)0.068 (15)*
H214C0.923 (4)0.283 (6)0.697 (2)0.11 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0214 (13)0.0299 (15)0.0269 (15)0.0011 (11)0.0065 (11)0.0005 (12)
O110.0243 (9)0.0349 (11)0.0335 (11)0.0019 (8)0.0079 (8)0.0023 (9)
C1130.0255 (14)0.0257 (15)0.057 (2)0.0003 (12)0.0075 (14)0.0033 (14)
O1130.0338 (12)0.0396 (13)0.0713 (18)0.0028 (10)0.0056 (11)0.0172 (13)
C1140.0258 (17)0.049 (2)0.085 (3)0.0029 (16)0.0183 (19)0.002 (2)
C120.0312 (15)0.0339 (16)0.0216 (14)0.0014 (12)0.0061 (11)0.0011 (12)
C130.0275 (13)0.0401 (16)0.0216 (13)0.0050 (13)0.0038 (10)0.0022 (12)
C1310.0258 (15)0.065 (2)0.0284 (17)0.0019 (15)0.0025 (12)0.0074 (16)
C1320.0381 (18)0.052 (2)0.0345 (18)0.0145 (16)0.0099 (14)0.0116 (16)
C140.0286 (14)0.0396 (18)0.0219 (14)0.0072 (13)0.0047 (11)0.0004 (12)
C14a0.0275 (13)0.0355 (15)0.0169 (13)0.0044 (12)0.0033 (10)0.0033 (11)
C150.0259 (14)0.0444 (18)0.0247 (14)0.0054 (13)0.0061 (11)0.0006 (13)
C160.0312 (14)0.0367 (17)0.0265 (15)0.0015 (13)0.0113 (12)0.0035 (13)
C16a0.0293 (14)0.0338 (15)0.0168 (13)0.0001 (12)0.0007 (11)0.0010 (12)
C170.0219 (13)0.0376 (16)0.0255 (14)0.0009 (12)0.0033 (11)0.0053 (12)
O170.0377 (12)0.0489 (14)0.0265 (11)0.0056 (10)0.0047 (9)0.0074 (10)
C17a0.0218 (13)0.0360 (16)0.0280 (15)0.0028 (11)0.0049 (11)0.0034 (13)
C180.0295 (15)0.0373 (17)0.0353 (18)0.0041 (13)0.0099 (13)0.0069 (14)
C190.0339 (16)0.0347 (17)0.047 (2)0.0072 (13)0.0152 (14)0.0080 (15)
C1100.0390 (18)0.0304 (17)0.0384 (19)0.0024 (14)0.0154 (14)0.0035 (14)
C1110.0290 (14)0.0385 (16)0.0262 (15)0.0020 (12)0.0090 (12)0.0003 (13)
O1110.0466 (13)0.0356 (13)0.0256 (11)0.0037 (10)0.0046 (9)0.0053 (9)
C111a0.0216 (12)0.0277 (14)0.0274 (14)0.0026 (11)0.0065 (11)0.0012 (11)
C1120.0223 (13)0.0315 (15)0.0239 (14)0.0027 (11)0.0070 (11)0.0004 (12)
O1120.0469 (13)0.0349 (12)0.0229 (10)0.0030 (10)0.0020 (9)0.0001 (9)
C112a0.0222 (12)0.0320 (15)0.0205 (13)0.0011 (11)0.0024 (10)0.0000 (11)
C112b0.0271 (14)0.0294 (15)0.0181 (14)0.0005 (11)0.0021 (11)0.0020 (11)
C210.0233 (14)0.0264 (15)0.0234 (14)0.0013 (11)0.0044 (11)0.0019 (11)
O210.0239 (9)0.0342 (11)0.0269 (10)0.0006 (8)0.0055 (8)0.0003 (8)
C2130.0276 (14)0.0251 (14)0.0354 (16)0.0018 (11)0.0007 (12)0.0057 (12)
O2130.0346 (11)0.0341 (11)0.0414 (13)0.0016 (9)0.0006 (9)0.0075 (10)
C2140.0296 (17)0.049 (2)0.058 (2)0.0037 (16)0.0089 (17)0.007 (2)
C220.0274 (13)0.0317 (15)0.0221 (14)0.0004 (12)0.0061 (11)0.0000 (11)
C230.0264 (13)0.0422 (17)0.0214 (13)0.0074 (13)0.0036 (11)0.0054 (12)
C2310.0278 (16)0.068 (3)0.0312 (18)0.0021 (16)0.0030 (13)0.0070 (17)
C2320.044 (2)0.059 (2)0.037 (2)0.0233 (18)0.0110 (16)0.0179 (18)
C240.0298 (15)0.0377 (17)0.0217 (14)0.0104 (13)0.0072 (11)0.0044 (12)
C24a0.0249 (13)0.0339 (15)0.0185 (13)0.0042 (11)0.0048 (10)0.0019 (11)
C250.0255 (14)0.0386 (16)0.0238 (14)0.0038 (12)0.0067 (11)0.0022 (12)
C260.0279 (14)0.0346 (16)0.0246 (14)0.0018 (12)0.0090 (12)0.0060 (12)
C26a0.0286 (13)0.0290 (14)0.0196 (13)0.0020 (11)0.0038 (11)0.0011 (11)
C270.0215 (12)0.0336 (15)0.0265 (14)0.0013 (11)0.0033 (11)0.0042 (12)
O270.0392 (12)0.0429 (13)0.0259 (11)0.0037 (10)0.0026 (9)0.0085 (9)
C27a0.0217 (13)0.0285 (14)0.0282 (15)0.0030 (11)0.0056 (11)0.0042 (12)
C280.0304 (15)0.0353 (17)0.0301 (17)0.0053 (13)0.0080 (12)0.0082 (13)
C290.0389 (17)0.0254 (15)0.045 (2)0.0076 (13)0.0150 (14)0.0053 (13)
C2100.0336 (16)0.0308 (16)0.0387 (18)0.0007 (13)0.0122 (14)0.0054 (14)
C2110.0262 (13)0.0302 (15)0.0290 (15)0.0003 (11)0.0078 (12)0.0010 (12)
O2110.0477 (13)0.0326 (12)0.0266 (12)0.0018 (10)0.0042 (10)0.0021 (9)
C211a0.0217 (12)0.0301 (14)0.0219 (14)0.0012 (11)0.0036 (10)0.0005 (11)
C2120.0205 (12)0.0306 (15)0.0217 (13)0.0001 (11)0.0048 (10)0.0003 (11)
O2120.0419 (12)0.0324 (12)0.0213 (10)0.0042 (9)0.0001 (9)0.0002 (8)
C212a0.0212 (12)0.0273 (14)0.0191 (13)0.0009 (10)0.0026 (10)0.0018 (11)
C212b0.0249 (13)0.0262 (14)0.0207 (14)0.0010 (11)0.0020 (11)0.0007 (11)
Geometric parameters (Å, º) top
C11—O111.422 (3)C21—O211.424 (5)
C11—C121.317 (4)C21—C221.325 (4)
C11—C112b1.510 (4)C21—C212b1.499 (5)
O11—C1131.354 (5)O21—C2131.361 (5)
C113—O1131.207 (6)C213—O2131.200 (5)
C113—C1141.494 (7)C213—C2141.493 (6)
C114—H114A1.01 (5)C214—H214A1.04 (4)
C114—H114B0.91 (6)C214—H214B0.90 (5)
C114—H114C1.02 (7)C214—H214C0.95 (7)
C12—C131.508 (6)C22—C231.509 (6)
C12—H120.94 (4)C22—H220.96 (3)
C13—C1311.525 (5)C23—C2311.535 (5)
C13—C1321.536 (5)C23—C2321.531 (5)
C13—C141.544 (6)C23—C241.541 (6)
C131—H131A0.97 (4)C231—H231A0.96 (5)
C131—H131B1.05 (4)C231—H231B1.03 (4)
C131—H131C0.97 (4)C231—H231C1.08 (4)
C132—H132A0.97 (4)C232—H232A1.04 (5)
C132—H132B1.08 (5)C232—H232B1.03 (5)
C132—H132C1.07 (4)C232—H232C0.97 (4)
C14—C14a1.509 (5)C24—C24a1.501 (5)
C14—H14A1.02 (4)C24—H24A1.04 (4)
C14—H14B1.03 (4)C24—H24B0.95 (4)
C14a—C151.330 (5)C24a—C251.325 (5)
C14a—C112b1.515 (6)C24a—C212b1.519 (6)
C15—C161.496 (5)C25—C261.505 (5)
C15—H150.98 (4)C25—H250.92 (3)
C16—C16a1.541 (6)C26—C26a1.549 (6)
C16—H16aA1.03 (4)C26—H26aA0.98 (4)
C16—H16B1.02 (4)C26—H26B0.99 (3)
C16a—C171.504 (5)C26a—C271.508 (4)
C16a—C112a1.540 (6)C26a—C212a1.536 (6)
C16a—H16aA0.95 (3)C26a—H26aA1.00 (3)
C17—O171.223 (5)C27—O271.217 (5)
C17—C17a1.488 (5)C27—C27a1.499 (5)
C17a—C181.392 (5)C27a—C281.387 (4)
C17a—C111a1.415 (6)C27a—C211a1.415 (5)
C18—C191.390 (6)C28—C291.393 (6)
C18—H181.04 (3)C28—H280.97 (3)
C19—C1101.382 (6)C29—C2101.372 (6)
C19—H191.02 (4)C29—H290.92 (4)
C110—C1111.399 (5)C210—C2111.399 (4)
C110—H1100.91 (4)C210—H2100.95 (3)
C111—O1111.352 (5)C211—O2111.347 (5)
C111—C111a1.410 (5)C211—C211a1.409 (5)
O111—H1110.88 (6)O211—H2110.92 (4)
C111a—C1121.480 (4)C211a—C2121.482 (4)
C112—O1121.229 (5)C212—O2121.229 (5)
C112—C112a1.513 (5)C212—C212a1.510 (5)
C112a—C112b1.537 (4)C212a—C212b1.538 (4)
C112a—H112A0.93 (3)C212a—H212A1.00 (3)
C112b—H112B1.00 (3)C212b—H212B1.01 (3)
O11—C11—C12118.3 (2)O21—C21—C22117.8 (3)
O11—C11—C112b114.8 (2)O21—C21—C212b115.7 (3)
C12—C11—C112b126.7 (2)C22—C21—C212b126.5 (3)
C11—O11—C113118.0 (3)C21—O21—C213118.1 (3)
O11—C113—O113123.8 (4)O21—C213—O213123.7 (4)
O11—C113—C114111.1 (4)O21—C213—C214110.6 (4)
O113—C113—C114125.1 (4)O213—C213—C214125.7 (4)
C113—C114—H114A113 (2)C213—C214—H214A107 (3)
C113—C114—H114B112 (3)C213—C214—H214B114 (3)
C113—C114—H114C111 (4)C213—C214—H214C105 (4)
H114A—C114—H114B103 (4)H214A—C214—H214B117 (4)
H114A—C114—H114C106 (5)H214A—C214—H214C109 (4)
H114B—C114—H114C111 (5)H214B—C214—H214C103 (5)
C11—C12—C13123.2 (3)C21—C22—C23123.7 (4)
C11—C12—H12121 (2)C21—C22—H22115.6 (16)
C13—C12—H12116 (2)C23—C22—H22120.4 (16)
C12—C13—C131108.6 (3)C22—C23—C231109.2 (3)
C12—C13—C132109.7 (3)C22—C23—C232109.4 (3)
C12—C13—C14109.1 (3)C22—C23—C24109.0 (3)
C131—C13—C132110.0 (3)C231—C23—C232110.5 (3)
C131—C13—C14111.2 (3)C231—C23—C24110.5 (3)
C132—C13—C14108.3 (3)C232—C23—C24108.2 (3)
C13—C131—H131A111 (2)C23—C231—H231A105 (3)
C13—C131—H131B108 (2)C23—C231—H231B114 (2)
C13—C131—H131C113 (2)C23—C231—H231C112.5 (19)
H131A—C131—H131B109 (3)H231A—C231—H231B108 (3)
H131A—C131—H131C102 (3)H231A—C231—H231C111 (3)
H131B—C131—H131C113 (3)H231B—C231—H231C106 (3)
C13—C132—H132A106 (2)C23—C232—H232A111 (2)
C13—C132—H132B109 (2)C23—C232—H232B110 (3)
C13—C132—H132C110 (2)C23—C232—H232C111 (2)
H132A—C132—H132B109 (3)H232A—C232—H232B104 (4)
H132A—C132—H132C108 (3)H232A—C232—H232C111 (3)
H132B—C132—H132C114 (3)H232B—C232—H232C110 (4)
C13—C14—C14a112.9 (3)C23—C24—C24a114.8 (3)
C13—C14—H14A104 (2)C23—C24—H24A107 (2)
C13—C14—H14B109.9 (18)C23—C24—H24B113 (2)
C14a—C14—H14A107 (2)C24a—C24—H24A110 (2)
C14a—C14—H14B106.9 (18)C24a—C24—H24B111 (2)
H14A—C14—H14B117 (3)H24A—C24—H24B101 (3)
C14—C14a—C15123.3 (4)C24—C24a—C25122.9 (4)
C14—C14a—C112b115.4 (3)C24—C24a—C212b115.4 (3)
C15—C14a—C112b121.3 (3)C25—C24a—C212b121.5 (3)
C14a—C15—C16124.9 (4)C24a—C25—C26125.0 (4)
C14a—C15—H15121 (2)C24a—C25—H25118.5 (19)
C16—C15—H15114 (2)C26—C25—H25116.5 (19)
C15—C16—C16a112.6 (3)C25—C26—C26a112.2 (3)
C15—C16—H16aA110.6 (18)C25—C26—H26aA112 (2)
C15—C16—H16B109 (2)C25—C26—H26B110.8 (18)
C16a—C16—H16aA108.8 (18)C26a—C26—H26aA106 (2)
C16a—C16—H16B111 (2)C26a—C26—H26B109 (2)
H16aA—C16—H16B104 (3)H26aA—C26—H26B106 (3)
C16—C16a—C17109.1 (3)C26—C26a—C27108.3 (3)
C16—C16a—C112a110.2 (3)C26—C26a—C212a110.8 (3)
C16—C16a—H16aA111 (2)C26—C26a—H26aA108 (2)
C17—C16a—C112a111.7 (3)C27—C26a—C212a111.9 (3)
C17—C16a—H16aA107.9 (18)C27—C26a—H26aA110.1 (18)
C112a—C16a—H16aA107 (2)C212a—C26a—H26aA108 (2)
C16a—C17—O17121.5 (3)C26a—C27—O27122.2 (3)
C16a—C17—C17a116.3 (3)C26a—C27—C27a115.9 (3)
O17—C17—C17a122.1 (3)O27—C27—C27a121.8 (3)
C17—C17a—C18118.9 (4)C27—C27a—C28118.9 (3)
C17—C17a—C111a120.4 (3)C27—C27a—C211a120.0 (3)
C18—C17a—C111a120.7 (3)C28—C27a—C211a121.0 (3)
C17a—C18—C19119.4 (4)C27a—C28—C29119.3 (4)
C17a—C18—H18120.9 (17)C27a—C28—H28123.8 (18)
C19—C18—H18119.7 (17)C29—C28—H28116.8 (18)
C18—C19—C110121.2 (3)C28—C29—C210121.0 (3)
C18—C19—H19117 (2)C28—C29—H29121 (2)
C110—C19—H19121 (2)C210—C29—H29118 (2)
C19—C110—C111120.0 (4)C29—C210—C211120.4 (4)
C19—C110—H110122 (3)C29—C210—H210123 (2)
C111—C110—H110118 (3)C211—C210—H210117 (2)
C110—C111—O111116.9 (3)C210—C211—O211117.7 (3)
C110—C111—C111a120.0 (4)C210—C211—C211a120.0 (4)
O111—C111—C111a123.1 (3)O211—C211—C211a122.3 (3)
C111—O111—H111107 (3)C211—O211—H211108 (2)
C17a—C111a—C111118.7 (3)C27a—C211a—C211118.3 (3)
C17a—C111a—C112121.0 (3)C27a—C211a—C212121.6 (3)
C111—C111a—C112120.3 (3)C211—C211a—C212120.1 (3)
C111a—C112—O112121.0 (3)C211a—C212—O212120.6 (3)
C111a—C112—C112a117.0 (3)C211a—C212—C212a117.0 (3)
O112—C112—C112a121.9 (3)O212—C212—C212a122.3 (3)
C16a—C112a—C112110.1 (3)C26a—C212a—C212110.9 (3)
C16a—C112a—C112b108.4 (3)C26a—C212a—C212b108.4 (3)
C16a—C112a—H112A111.3 (18)C26a—C212a—H212A107.7 (18)
C112—C112a—C112b116.5 (3)C212—C212a—C212b116.0 (3)
C112—C112a—H112A99.1 (18)C212—C212a—H212A106.3 (19)
C112b—C112a—H112A111.2 (18)C212b—C212a—H212A107.2 (19)
C11—C112b—C14a110.4 (3)C21—C212b—C24a110.9 (3)
C11—C112b—C112a114.6 (3)C21—C212b—C212a115.1 (3)
C11—C112b—H112B107.4 (19)C21—C212b—H212B109 (2)
C14a—C112b—C112a111.7 (3)C24a—C212b—C212a111.4 (3)
C14a—C112b—H112B106 (2)C24a—C212b—H212B105 (2)
C112a—C112b—H112B106.2 (17)C212a—C212b—H212B105.2 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O111—H111···O1120.88 (6)1.83 (5)2.618 (4)148 (4)
O211—H211···O2120.92 (4)1.77 (4)2.586 (4)147 (3)

Experimental details

Crystal data
Chemical formulaC22H22O5
Mr366.41
Crystal system, space groupMonoclinic, Cc
Temperature (K)153
a, b, c (Å)13.774 (2), 11.233 (2), 24.595 (4)
β (°) 99.792 (2)
V3)3750.0 (11)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.32 × 0.21 × 0.17
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
SADABS; Sheldrick, 1996
Tmin, Tmax0.87, 0.96
No. of measured, independent and
observed [F > 2σ(F)] reflections
21857, 4771, 4288
Rint0.044
(sin θ/λ)max1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.046, 1.07
No. of reflections4288
No. of parameters661
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.34, 0.23

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), Xtal3.5 (Hall, King, and Stewart, 1995), CRYLSQ in Xtal3.5, BONDLA and CIFIO in Xtal3.5.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O111—H111···O1120.88 (6)1.83 (5)2.618 (4)148 (4)
O211—H211···O2120.92 (4)1.77 (4)2.586 (4)147 (3)
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds