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The host xanthenol compound forms a 1:1 clathrate with dioxane, namely 9-(1-naphthyl)-9H-xanthen-9-ol-1,4-dioxane, C23H16O2·C4H8O2. The structure of this clathrate is reported, along with a study of the kinetics of desolvation and the determination of an activation energy. The guest mol­ecules are stabilized by Ohost-H...Oguest hydrogen bonds [O-H = 0.968 (2) Å, O...O = 2.7532 (13) Å and O-H...O = 151.9 (4)°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104017792/ta1455sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270104017792/ta1455Isup2.hkl
Contains datablock I

CCDC reference: 251325

Comment top

The conformation of the two components of 9-(1-naphthyl)-9H-xanthen-9-ol–dioxane, (I), are shown in Fig. 1. A search of the Cambridge Structural Database (CSD, Version 5.25; Allen, 2002) revealed that no structures of this host molecule have been published to date. We present here the crystal structure of the title clathrate. \sch

Bond lengths and angles for the host and guest in (I) generally fall in the expected ranges. The xanthene ring of the host is slightly non-planar, with the dihedral angle between the least-squares planes of the two phenyl rings being 5.17 (4)°. The host naphthalene moiety and the xanthene ring are nearly orthogonal, the dihedral angle between their least-squares planes being 88.21 (2)°. This is comparable with the conformation found in similar structures, such as bis(9-phenyl-9-hydroxy)xanthene tris(dioxane) clathrate (Csöregh et al., 1993). In other structures, such as 9-(cyclohepta-2,4,6-trien-1-yl)xanthen-9-ol (Badejo et al., 1991), the dihedral angle is substantially different, at 21.9 (2)°. The 1,4-dioxane guest molecule is in the expected chair conformation (Fig. 1).

Dioxane is an interesting guest molecule, since it has two O atoms which are capable of being hydrogen-bond acceptors. A series of similar hosts have been observed to include dioxane, with host:guest stoichiometries varying from 2:1 to 2:3 (Csöregh et al., 1993), with the guests situated in channels or cages. In this study, each host molecule is hydrogen-bonded via its hydroxyl moiety to one dioxane molecule. This is consistent with Csöregh's study, which suggested that the more bulky the substituent attached to the xanthene ring, the greater the tendency for a single host–guest interaction.

In the crystal of (I), the host molecules pack in zigzag layers parallel to [100] and the dioxane guests lie in cages created by the host framework (Fig. 2). The hydrogen-bonded host–guest units form spirals which extend along [010]. The spiral shape is largely due to the torsion angle between the xanthenol and naphthalene moieties of the host [C8—C7—C14—C15 61.56 (14)°]. We used the program SECTION (Barbour, 1999a) to map the cavities and found that the approximate size of these cages is 7.6 × 6.5 × 7.4 Å. This compares favourably with other structures, such as 9-[4-(tert-butyl)phenyl]fluoren-9-ol-dioxane clathrate (Csöregh et al., 1993), where the cages have approximate dimensions 5.7 × 7.1 × 9.7 Å.

Thermogravimetric analysis (TGA) of (I) shows a single mass-loss step (calculated mass loss 21.4%, observed mass loss 21.3%), which is consistent with the host-to-guest ratio of 1:1. Two endotherms were observed in the differential scanning calorimetry (DSC). The first of these (Ton 380.4 K) corresponds to the loss of guest and the second (Ton 468.0 K) represents the host melt. Both TGA and DSC curves are shown in Fig. 3.

The kinetics of desolvation for (I) were determined by performing a series of isothermal TG experiments between 328 and 348 K. The resultant mass-time curves were sigmoidal and fitted the Avrami-Erofeev rate law (A4), [-ln(1-α)]1/4 = kt, where α is the extent of the reaction and k is the rate constant (Brown, 1988). The corresponding Arrhenius plot is shown in Fig. 4. An activation energy of 111 (2) kJ mol−1 was obtained.

Experimental top

The host compound was synthesized using the method of Dilthey et al. (1939). IR spectra of the host alone showed νmax values (CHCl3) of 3584.1 (s, free OH) and 3370.1 (Br, bonded OH) cm−1. IR spectra were recorded on a Perkin-Elmer 1600 Series Fourier-Transform spectrometer. Suitable crystals of (I) were obtained by slow evaporation of dilute solutions of the host in liquid dioxane at room temperature. The crystals were crushed for thermal analysis. TGA was performed on a Mettler Toledo Stare system and DSC was carried out on a Perkin-Elmer PC7 Series system.

Refinement top

The aromatic H atoms of the host and the CH2 H atoms of the dioxane guest were located in difference electron-density maps, but they were geometrically constrained with C—H distances fixed at 0.95 and 0.99 Å, respectively. The hydroxyl H atom was located in a difference electron-density map, and was initially refined isotropically. Thereafter, it was placed in a geometrically calculated position based on the relationship between O—H and O···O distances (Olovsson & Jönsson, 1975), and its position was refined under distance restraints, starting with O2—H1 0.919 (15) and H1···O2G 1.837 (1) Å. Friedel pairs were merged for the final refinement.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 1999b); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the two components of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The structure of (I), viewed down [100]. The hydrogen bond is shown as a dashed line.
[Figure 3] Fig. 3. T GA and DSC curves for (I).
[Figure 4] Fig. 4. Arrhenius plot for the desolvation of (I).
9-(1-naphthyl)-9H-xanthen-9-ol–dioxane (1/1) clathrate top
Crystal data top
C23H16O2·C4H8O2F(000) = 872
Mr = 412.46Dx = 1.314 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 14703 reflections
a = 13.597 (3) Åθ = 4.5–26.6°
b = 10.404 (2) ŵ = 0.09 mm1
c = 14.735 (3) ÅT = 173 K
V = 2084.5 (7) Å3Rectangular, colourless
Z = 40.36 × 0.30 × 0.27 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
2095 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 26.6°, θmin = 4.5°
ϕ scans and ωh = 1516
14703 measured reflectionsk = 1313
2202 independent reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0476P)2 + 0.3201P]
where P = (Fo2 + 2Fc2)/3
2202 reflections(Δ/σ)max = 0.004
284 parametersΔρmax = 0.27 e Å3
3 restraintsΔρmin = 0.27 e Å3
Crystal data top
C23H16O2·C4H8O2V = 2084.5 (7) Å3
Mr = 412.46Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 13.597 (3) ŵ = 0.09 mm1
b = 10.404 (2) ÅT = 173 K
c = 14.735 (3) Å0.36 × 0.30 × 0.27 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
2095 reflections with I > 2σ(I)
14703 measured reflectionsRint = 0.027
2202 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0303 restraints
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.27 e Å3
2202 reflectionsΔρmin = 0.27 e Å3
284 parameters
Special details top

Experimental. none

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) top
xyzUiso*/Ueq
O10.02781 (6)0.68206 (9)0.27386 (7)0.0305 (2)
C10.11736 (8)0.70706 (11)0.23368 (8)0.0215 (3)
O20.26982 (6)0.63727 (7)0.41612 (6)0.02205 (19)
H10.2405 (2)0.7115 (2)0.4450 (3)0.090 (8)*
C20.11322 (10)0.78547 (11)0.15707 (9)0.0264 (3)
H20.05190.81710.13580.032*
C30.19892 (11)0.81647 (12)0.11258 (9)0.0284 (3)
H30.19670.86890.05990.034*
C40.28883 (10)0.77145 (12)0.14437 (9)0.0292 (3)
H40.34820.79490.11460.035*
C50.29105 (9)0.69211 (11)0.21985 (9)0.0232 (3)
H50.35250.66090.24110.028*
C60.20530 (8)0.65708 (10)0.26525 (8)0.0183 (2)
C70.21127 (8)0.57235 (10)0.34919 (7)0.0182 (2)
C80.10915 (8)0.55120 (11)0.38811 (8)0.0200 (2)
C90.09734 (10)0.47796 (12)0.46646 (9)0.0272 (3)
H90.15290.43640.49220.033*
C100.00648 (10)0.46432 (13)0.50766 (11)0.0341 (3)
H100.00000.41340.56090.041*
C110.07502 (10)0.52528 (13)0.47095 (10)0.0317 (3)
H110.13740.51680.49930.038*
C120.06567 (9)0.59796 (12)0.39350 (10)0.0287 (3)
H120.12140.63960.36810.034*
C130.02614 (9)0.60994 (11)0.35261 (8)0.0222 (3)
C140.26469 (8)0.44521 (11)0.32872 (8)0.0189 (2)
C150.22642 (9)0.35502 (10)0.26434 (8)0.0202 (3)
C160.13696 (9)0.37126 (11)0.21612 (9)0.0244 (3)
H160.09860.44610.22670.029*
C170.10441 (11)0.28195 (12)0.15480 (9)0.0314 (3)
H170.04380.29530.12420.038*
C180.15978 (12)0.17061 (13)0.13657 (10)0.0347 (3)
H180.13750.11010.09290.042*
C190.24560 (11)0.15053 (12)0.18213 (10)0.0329 (3)
H190.28260.07490.17020.039*
C200.28095 (9)0.23979 (12)0.24690 (9)0.0256 (3)
C210.36926 (10)0.21657 (13)0.29498 (11)0.0336 (3)
H210.40540.14000.28380.040*
C220.40275 (10)0.30239 (13)0.35677 (10)0.0336 (3)
H220.46140.28480.38950.040*
C230.35095 (9)0.41808 (12)0.37298 (9)0.0250 (3)
H230.37650.47820.41540.030*
O1G0.57502 (7)0.41838 (9)0.51459 (7)0.0337 (2)
C1G0.64612 (10)0.40696 (13)0.44347 (11)0.0349 (3)
H1GA0.63000.33180.40500.042*
H1GB0.71210.39290.47010.042*
O2G0.66853 (7)0.63639 (8)0.44131 (7)0.0342 (2)
C2G0.64738 (11)0.52669 (13)0.38611 (10)0.0350 (3)
H2GA0.69800.51830.33810.042*
H2GB0.58270.53790.35640.042*
C3G0.59767 (11)0.64770 (13)0.51281 (10)0.0334 (3)
H3GA0.53140.66150.48660.040*
H3GB0.61390.72270.55140.040*
C4G0.59772 (11)0.52758 (13)0.56930 (10)0.0337 (3)
H4GA0.66320.51600.59750.040*
H4GB0.54850.53570.61850.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0198 (4)0.0359 (5)0.0360 (5)0.0032 (3)0.0017 (4)0.0123 (4)
C10.0219 (5)0.0192 (5)0.0236 (6)0.0003 (4)0.0012 (4)0.0008 (5)
O20.0224 (4)0.0231 (4)0.0207 (4)0.0009 (3)0.0039 (3)0.0038 (3)
C20.0320 (6)0.0205 (5)0.0267 (6)0.0040 (5)0.0079 (5)0.0022 (5)
C30.0428 (7)0.0201 (5)0.0223 (6)0.0016 (5)0.0018 (5)0.0036 (5)
C40.0348 (6)0.0253 (6)0.0276 (6)0.0010 (5)0.0081 (5)0.0057 (5)
C50.0238 (5)0.0204 (5)0.0254 (6)0.0018 (4)0.0013 (5)0.0009 (5)
C60.0225 (5)0.0143 (4)0.0181 (5)0.0006 (4)0.0003 (4)0.0017 (4)
C70.0189 (5)0.0179 (5)0.0176 (5)0.0004 (4)0.0027 (4)0.0006 (4)
C80.0206 (5)0.0175 (5)0.0219 (5)0.0002 (4)0.0013 (4)0.0026 (4)
C90.0252 (6)0.0296 (6)0.0266 (6)0.0025 (5)0.0028 (5)0.0062 (5)
C100.0342 (7)0.0359 (7)0.0321 (6)0.0043 (6)0.0091 (6)0.0066 (6)
C110.0243 (6)0.0337 (7)0.0370 (7)0.0056 (5)0.0093 (5)0.0053 (6)
C120.0182 (5)0.0284 (6)0.0394 (7)0.0005 (5)0.0001 (5)0.0032 (5)
C130.0213 (5)0.0200 (5)0.0252 (6)0.0008 (4)0.0004 (5)0.0007 (5)
C140.0197 (5)0.0176 (5)0.0192 (5)0.0004 (4)0.0019 (4)0.0040 (4)
C150.0245 (5)0.0177 (5)0.0183 (5)0.0010 (4)0.0036 (4)0.0027 (4)
C160.0288 (6)0.0194 (5)0.0249 (6)0.0002 (4)0.0022 (5)0.0012 (5)
C170.0387 (7)0.0265 (6)0.0290 (6)0.0042 (5)0.0047 (6)0.0029 (6)
C180.0478 (8)0.0253 (6)0.0311 (7)0.0050 (6)0.0019 (6)0.0076 (5)
C190.0421 (7)0.0200 (5)0.0366 (7)0.0003 (5)0.0111 (6)0.0063 (5)
C200.0293 (6)0.0196 (5)0.0278 (6)0.0019 (4)0.0075 (5)0.0028 (5)
C210.0312 (6)0.0230 (6)0.0467 (8)0.0100 (5)0.0062 (6)0.0025 (6)
C220.0233 (6)0.0312 (6)0.0463 (8)0.0081 (5)0.0043 (6)0.0049 (6)
C230.0227 (5)0.0247 (6)0.0276 (6)0.0008 (4)0.0012 (5)0.0027 (5)
O1G0.0285 (4)0.0268 (4)0.0459 (5)0.0065 (4)0.0034 (4)0.0041 (4)
C1G0.0291 (6)0.0249 (6)0.0508 (8)0.0023 (5)0.0052 (7)0.0029 (6)
O2G0.0425 (5)0.0234 (4)0.0366 (5)0.0061 (4)0.0142 (5)0.0003 (4)
C2G0.0400 (7)0.0289 (6)0.0361 (7)0.0017 (5)0.0078 (6)0.0044 (6)
C3G0.0415 (7)0.0258 (6)0.0330 (7)0.0002 (6)0.0119 (6)0.0017 (6)
C4G0.0363 (7)0.0302 (7)0.0347 (7)0.0036 (5)0.0028 (6)0.0053 (6)
Geometric parameters (Å, º) top
O1—C11.3787 (15)C15—C201.4329 (16)
O1—C131.3822 (16)C16—C171.3696 (18)
C1—C61.3843 (16)C16—H160.9500
C1—C21.3939 (17)C17—C181.407 (2)
O2—C71.4363 (13)C17—H170.9500
O2—H10.9683 (18)C18—C191.362 (2)
C2—C31.3753 (19)C18—H180.9500
C2—H20.9500C19—C201.4159 (19)
C3—C41.390 (2)C19—H190.9500
C3—H30.9500C20—C211.4148 (19)
C4—C51.3855 (18)C21—C221.354 (2)
C4—H40.9500C21—H210.9500
C5—C61.3927 (16)C22—C231.4150 (18)
C5—H50.9500C22—H220.9500
C6—C71.5210 (15)C23—H230.9500
C7—C81.5182 (16)O1G—C4G1.4268 (17)
C7—C141.5389 (16)O1G—C1G1.4308 (18)
C8—C131.3860 (16)C1G—C2G1.505 (2)
C8—C91.3926 (17)C1G—H1GA0.9900
C9—C101.3839 (19)C1G—H1GB0.9900
C9—H90.9500O2G—C2G1.4308 (16)
C10—C111.387 (2)O2G—C3G1.4326 (17)
C10—H100.9500C2G—H2GA0.9900
C11—C121.375 (2)C2G—H2GB0.9900
C11—H110.9500C3G—C4G1.5017 (19)
C12—C131.3917 (17)C3G—H3GA0.9900
C12—H120.9500C3G—H3GB0.9900
C14—C231.3714 (17)C4G—H4GA0.9900
C14—C151.4321 (16)C4G—H4GB0.9900
C15—C161.4188 (17)
C1—O1—C13118.52 (9)C16—C15—C20116.96 (11)
C1—C2—H2120.4C16—C17—C18120.77 (13)
C1—C6—C5117.60 (10)C16—C17—H17119.6
C1—C6—C7122.48 (10)C17—C16—C15121.78 (11)
O1—C1—C6123.20 (10)C17—C16—H16119.1
O1—C1—C2114.99 (10)C17—C18—H18120.3
O1—C13—C8122.88 (10)C18—C17—H17119.6
O1—C13—C12115.27 (10)C18—C19—C20121.49 (12)
C2—C3—C4120.35 (12)C18—C19—H19119.3
C2—C3—H3119.8C19—C18—C17119.36 (13)
O2—C7—C8108.40 (9)C19—C18—H18120.3
O2—C7—C6108.39 (9)C19—C20—C15119.61 (12)
O2—C7—C14106.10 (9)C20—C19—H19119.3
C3—C2—C1119.28 (12)C20—C21—H21119.7
C3—C2—H2120.4C21—C20—C19120.90 (12)
C3—C4—H4120.3C21—C20—C15119.49 (11)
C4—C5—C6121.55 (11)C21—C22—C23120.47 (12)
C4—C5—H5119.2C21—C22—H22119.8
C4—C3—H3119.8C22—C21—C20120.62 (12)
C5—C4—C3119.37 (12)C22—C21—H21119.7
C5—C4—H4120.3C22—C23—H23119.3
C5—C6—C7119.84 (10)C23—C22—H22119.8
C6—C1—C2121.80 (11)C23—C14—C15119.40 (11)
C6—C5—H5119.2C23—C14—C7119.17 (10)
C6—C7—C14111.34 (9)C1G—C2G—H2GA109.6
C7—O2—H1116.7 (2)C1G—C2G—H2GB109.6
C8—C7—C6110.02 (9)O1G—C1G—C2G110.50 (11)
C8—C7—C14112.40 (9)O1G—C1G—H1GA109.5
C8—C9—H9119.2O1G—C1G—H1GB109.5
C8—C13—C12121.84 (12)O1G—C4G—C3G110.45 (12)
C9—C8—C7119.86 (10)O1G—C4G—H4GA109.6
C9—C10—C11119.69 (13)O1G—C4G—H4GB109.6
C9—C10—H10120.2H1GA—C1G—H1GB108.1
C10—C9—C8121.52 (12)C2G—C1G—H1GB109.5
C10—C9—H9119.2C2G—O2G—C3G110.39 (10)
C10—C11—H11120.0C2G—C1G—H1GA109.5
C11—C10—H10120.2O2G—C2G—C1G110.07 (12)
C11—C12—C13119.44 (12)O2G—C2G—H2GA109.6
C11—C12—H12120.3O2G—C2G—H2GB109.6
C12—C11—C10120.10 (13)O2G—C3G—C4G109.82 (11)
C12—C11—H11120.0O2G—C3G—H3GA109.7
C13—C12—H12120.3O2G—C3G—H3GB109.7
C13—C8—C9117.40 (11)H2GA—C2G—H2GB108.2
C13—C8—C7122.57 (10)C3G—C4G—H4GA109.6
C14—C23—C22121.37 (12)C3G—C4G—H4GB109.6
C14—C23—H23119.3H3GA—C3G—H3GB108.2
C14—C15—C20118.62 (11)C4G—C3G—H3GA109.7
C15—C14—C7121.44 (10)C4G—C3G—H3GB109.7
C15—C16—H16119.1C4G—O1G—C1G109.50 (10)
C16—C15—C14124.41 (10)H4GA—C4G—H4GB108.1
C1—C2—C3—C40.83 (19)C9—C10—C11—C120.6 (2)
C1—C6—C7—O2117.00 (11)C9—C8—C13—O1178.16 (11)
C1—C6—C7—C81.36 (14)C9—C8—C13—C120.60 (18)
C1—C6—C7—C14126.67 (11)C10—C11—C12—C130.2 (2)
C1—O1—C13—C86.46 (17)C11—C12—C13—O1178.40 (11)
C1—O1—C13—C12174.70 (11)C11—C12—C13—C80.45 (19)
O1—C1—C2—C3179.61 (11)C13—O1—C1—C63.99 (17)
O1—C1—C6—C71.66 (17)C13—O1—C1—C2177.05 (10)
O1—C1—C6—C5178.52 (11)C13—C8—C9—C100.16 (18)
C2—C1—C6—C7179.44 (11)C14—C7—C8—C13128.42 (12)
C2—C3—C4—C51.77 (19)C14—C7—C8—C956.44 (14)
C2—C1—C6—C52.59 (17)C14—C15—C16—C17179.53 (12)
O2—C7—C8—C13114.64 (12)C14—C15—C20—C211.57 (17)
O2—C7—C8—C960.50 (13)C14—C15—C20—C19178.67 (11)
O2—C7—C14—C230.33 (14)C15—C14—C23—C220.37 (18)
O2—C7—C14—C15179.87 (10)C15—C20—C21—C220.3 (2)
C3—C4—C5—C60.53 (19)C15—C16—C17—C180.8 (2)
C4—C5—C6—C11.61 (17)C16—C15—C20—C21178.14 (12)
C4—C5—C6—C7178.55 (11)C16—C15—C20—C191.61 (17)
C5—C6—C7—C8178.15 (10)C16—C17—C18—C191.5 (2)
C5—C6—C7—O259.78 (13)C17—C18—C19—C200.6 (2)
C5—C6—C7—C1456.55 (13)C18—C19—C20—C21178.80 (13)
C6—C1—C2—C31.41 (18)C18—C19—C20—C151.0 (2)
C6—C7—C8—C133.73 (15)C19—C20—C21—C22179.92 (13)
C6—C7—C8—C9178.86 (10)C20—C21—C22—C231.3 (2)
C6—C7—C14—C23117.40 (12)C20—C15—C16—C170.78 (18)
C6—C7—C14—C1562.41 (13)C21—C22—C23—C141.7 (2)
C7—C8—C9—C10175.22 (12)C23—C14—C15—C201.21 (17)
C7—C8—C13—O16.60 (18)C23—C14—C15—C16178.48 (11)
C7—C8—C13—C12174.64 (11)O1G—C1G—C2G—O2G57.94 (15)
C7—C14—C15—C161.72 (17)C1G—O1G—C4G—C3G59.12 (14)
C7—C14—C15—C20178.59 (10)C2G—O2G—C3G—C4G58.03 (15)
C7—C14—C23—C22179.83 (11)O2G—C3G—C4G—O1G59.00 (15)
C8—C9—C10—C110.4 (2)C3G—O2G—C2G—C1G57.57 (14)
C8—C7—C14—C23118.64 (12)C4G—O1G—C1G—C2G58.53 (14)
C8—C7—C14—C1561.56 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O2Gi0.97 (1)1.86 (1)2.753 (1)152 (1)
Symmetry code: (i) x1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formulaC23H16O2·C4H8O2
Mr412.46
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)173
a, b, c (Å)13.597 (3), 10.404 (2), 14.735 (3)
V3)2084.5 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.36 × 0.30 × 0.27
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
14703, 2202, 2095
Rint0.027
(sin θ/λ)max1)0.629
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.076, 1.07
No. of reflections2202
No. of parameters284
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.27

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 1999b), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O2Gi0.968 (3)1.861 (2)2.753 (1)152 (1)
Symmetry code: (i) x1/2, y+3/2, z.
 

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