organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(2E,4E,6E)-3-Methyl-7-(pyren-1-yl)octa-2,4,6-trienoic acid

aDepartment of Chemistry, University of Patras, 265 04 Patras, Greece, and bDepartment of Chemistry, University of Cyprus, 1678 Nicosia, Cyprus
*Correspondence e-mail: nastopoulos@chemistry.upatras.gr

(Received 27 July 2009; accepted 22 September 2009; online 30 September 2009)

The title compound, C25H20O2, was synthesized by a Wittig reaction between triphen­yl[1-(pyren-1-yl)eth­yl]phospho­nium bromide and ethyl (2E,4E)-3-methyl-6-oxohexa-2,4-dienoate, in the presence of n-butyl lithium, followed by saponification. It was obtained pure in the all-trans configuration following crystallization from ethyl acetate. The asymmetric unit contains two independent mol­ecules (A and B), which are arranged almost parallel to each other within the crystal structure. The triene chain is not coplanar with the pyrene ring system, forming dihedral angles of 52.8 (1) and 42.2 (1)° for mol­ecules A and B, respectively. Inter­molecular hydrogen bonds between the carboxyl groups of the mol­ecules link them into centrosymmetric pairs, AA and BB, each with the R22(8) graph-set motif.

Related literature

For general background on retinoids, see: Meyer et al. (1978[Meyer, H., Bollag, W., Hänni, R. & Rüegg, R. (1978). Experientia (Generalia), 34, 1105-1246.]); Sporn et al. (1994[Sporn, M. B., Roberts, A. B. & Goodman, D. S. (1994). Editors. The Retinoids - Biology, Chemistry and Medicine, 2nd ed. New York: Raven Press.]); Tian et al. (1997[Tian, K., Norris, A. W., Lin, C.-L. S. & Li, E. (1997). Biochemistry, 36, 5669-5676.]); Chaudhuri et al. (1999[Chaudhuri, B. N., Kleywegt, G. J., Broutin-L'Hermite, I., Bergfors, T., Senn, H., Le Motte, P., Partouche, O. & Jones, T. A. (1999). Acta Cryst. D55, 1850-1857.]); Malpezzi et al. (2005[Malpezzi, L., Magnone, G. A., Masciocchi, N. & Sironi, A. (2005). J. Pharm. Sci. 94, 1067-1078.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C25H20O2

  • Mr = 352.41

  • Triclinic, [P \overline 1]

  • a = 7.5751 (7) Å

  • b = 8.5466 (7) Å

  • c = 28.458 (3) Å

  • α = 97.086 (7)°

  • β = 93.003 (8)°

  • γ = 97.574 (7)°

  • V = 1808.0 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.21 × 0.17 × 0.14 mm

Data collection
  • Oxford Diffraction Xcalibur-3 with Sapphire CCD diffractometer

  • Absorption correction: none

  • 22799 measured reflections

  • 6284 independent reflections

  • 3448 reflections with I > 2σ(I)

  • Rint = 0.109

Refinement
  • R[F2 > 2σ(F2)] = 0.066

  • wR(F2) = 0.160

  • S = 1.00

  • 6284 reflections

  • 497 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2A—H2A1⋯O1Ai 0.876 (18) 1.756 (19) 2.629 (3) 174 (4)
O2B—H2B1⋯O1Bii 0.858 (18) 1.79 (2) 2.624 (3) 162 (4)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+3, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Comment top

Retinoids are compounds structurally related to vitamin A which play an important role in a variety of biological functions including vision, development, reproduction and cell differentiation and have been applied successfully to the management of severe skin disorders (Sporn et al., 1994; Meyer et al., 1978, and references therein). They exert their effects by binding to the nuclear receptors RAR and RXR, for which all-trans retinoic acid (ATRA, 1) (Fig. 1) and its 9-cis isomer have been identified as the principal natural ligands. A huge array of analogs of ATRA have been synthesized in order to improve the therapeutic efficacy to toxicity index and to provide better selectivities for various therapeutic applications. These analogs usually involve changes in the lipophilic part of the molecules and/or the tetraene chain. A well known such example is acitretin (2) which is currently the drug of choice for treating psoriasis and has been shown to exert its effect indirectly, that is not by binding to the retinoid receptors but by displacing ATRA from its cellular binding proteins (CRABPs) (Tian et al., 1997). Recently, the crystal structures of three polymorphic forms (I, II and III) of acitretin have been determined (Malpezzi et al., 2005) as well the crystal structures of the acitretin analog 3 (O-demethylated acitretin) and ATRA analog 4, in which the double bond adjacent to the ring is restricted within an aromatic ring, in complex with CRABP II (Chaudhuri et al., 1999). Both in the crystal structures of acitretin and its analog 3 the aromatic ring and the polyene chain are not coplanar but form dihedral angles of maximum 38.4° (forms I and II) and 60.8° (form III) and 56°, respectively, whereas in the crystal structure of ATRA analog 4, a charge/π-cloud interaction between the aromatic ring and Arg59 residue is identified (Chaudhuri et al., 1999) which might account for the somewhat stronger binding of 4 to CRABP II binding domain. We therefore considered of interest to combine structural features from the lipophilic parts of acitretin and ATRA analog 4. Accordingly, we synthesized acitretin analog 5 bearing a pyrene ring-system in the lipophilic part of the molecule by using as key-step the Wittig reaction of triphenyl[1-(pyren-1-yl)ethyl]phosphonium bromide, readily obtained from the commercially available 1-acetylpyrene, and ethyl (2E,4E)-3-methyl-6-oxohexa-2,4-dienoate whose synthesis has been described in the literature (Meyer et al., 1978).

Indeed, reduction of the commercially available 1-acetylpyrene (6) with NaBH4, followed by treatment of the thus obtained alcohol with Ph3P.HBr, provided the phosphonium salt (7) (Fig. 2). This salt was subjected to a Wittig reaction with the unsaturated aldehyde 8 (Meyer et al., 1978) using n-BuLi as the base to obtain ester 9 as a mixture of geometric isomers. Finally, saponification and recrystallization of the thus obtained acid from ethyl acetate provided the title compound (5). Only the all-E isomers of compounds 8 and 9 are drawn in Figure 2.

We now wish to report the results of the X-ray crystallographic analysis of acitretin analog 5. Its asymmetric unit contains two symmetry-independent molecules (labelled A and B) which are arranged almost parallel to each other within the crystal structure and have their carboxylic ends pointing in the same direction (Fig. 3). Molecules A and B have an enantiomeric-type relationship and a least-squares fit of A (blue) and B (red) within the asymmetric unit is presented in Fig. 4. The pyrene ring system of the two independent molecules shows a planar arrangement; the r.m.s. deviation of the sixteen atoms consisting this system is 0.042 Å and 0.019 Å for A and B, respectively. The triene chain of each molecule A and B forms with the corresponding pyrene system a dihedral angle of 52.8 (1)° and 42.2 (1)°, respectively.

The carboxylic moiety of each molecule forms strong intermolecular hydrogen bonds with a neighbouring centrosymmetric molecule (Table 1), thereby linking them into elongated AA and BB dimers located on crystallographic inversion centres; those interactions can be described by the classic graph-set motif of R22(8) (Bernstein et al., 1995). Similar centrosymmetric hydrogen-bonded dimers have also been observed in form II of acitretin (Malpezzi et al., 2005). The formation of such dimers excludes the possibility of the presence of specific supramolecular arrangements such as chains or layers. The packing of the dimers within the crystal structure is accomplished through normal van der Waals contacts.

Related literature top

For general background on retinoids, see: Meyer et al. (1978); Sporn et al. (1994); Tian et al. (1997); Chaudhuri et al. (1999); Malpezzi et al. (2005). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To an ice-cold solution of 1-acetylpyrene (0.73 g, 3 mmol) in MeOH/diglyme (3:7, 6 ml), NaBH4 (0.29 g, 7.6 mmol) was added portionwise in 15 min. The resulting reaction mixture was stirred at this temperature for 45 min. Excess NaBH4 was destroyed by adding icechips. The product was extracted with EtOAc, the organic layer was washed twice with H2O, dried over Na2SO4 and evaporated to dryness to leave the corresponding alcohol (0.71 g, 96% yield) as a pale yellow solid and had Rf (PhMe) 0.11. This alcohol was treated with Ph3P.HBr (2.0 g, 5.76 mmol) in MeCN/THF (7:3, 6 ml) at 80 oC for 12 h. After evaporation of the solvents, trituration with Et2O and overnight refrigeration, the corresponding phosphonium salt 7 was obtained as pale yellow solid (1.35 g, 82%) and used as such without further purification into the following experiment. A solution of phosphonium salt 7 (1.03 g, 1.8 mmol) in THF (1.5 ml) and DMPU (0.5 ml) was cooled at -10 oC and a 1.6 M solution of n-BuLi in hexanes (1.35 ml) was added dropwise. The resulting dark red solution was left to vigorously stirring over 30 min at this temperature. Then, temperature was set at -78 oC and aldehyde 8 (0.15 g, 0.9 mmol) was added. The resulting reaction mixture was left to stir at -78 oC over 30 min and then to attain room temperature for 12 h. Excess n-BuLi was destroyed by careful addition of a 5% aqueous solution of NH4Cl to pH 7–8. The mixture was extracted with EtOAc, washed twice with H2O, dried over Na2SO4 and evaporated to dryness. The corresponding unsaturated ester 9 (0.09 g, 25%) was obtained in oily form after f.c.c. purification using PhMe:Hex 7:3 as the eluent (Rf 0.28) as an inseparable mixture of geometric isomers (all-E-9 ca 75% of the mixture). The thus obtained ester 9 (0.09 g, 0.22 mmol) was suspended in MeOH/DMSO (6:1, 0.7 ml) and saponified with an 8 N aqueous solution of NaOH (0.11 ml) at 70 oC for 3 h. After evaporation of MeOH, the oily residue was diluted with H2O and acidified with glacial acetic acid to pH 5. The product was extracted with EtOAc. The organic layers were combined and washed once with a saturated aqueous solution of NaCl and twice with H2O, dried over Na2SO4 and evaporated to dryness to obtain the corresponding acid 5 (0.04 g, 85%) from which all-E-5 was obtained in 40% yield following crystallization from EtOAc. Recrystallization from EtOAc gave finally yellow crystals of all-trans-5 suitable for X-ray analysis; m.p. 517–518 K.

Refinement top

The H atoms of the carboxylic acid groups were located in difference Fourier maps and their positions were refined with soft distance restraints along with Uiso(H) equal to 1.5Ueq of their parent atoms. The methine and aromatic H atoms were placed in geometrically idealized positions [C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C)]; the remaining methyl H atoms were constrained to an ideal geometry [C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C)], but were allowed to rotate freely about the C—C bonds. Two low-angle reflections were omitted from the final cycles of refinement because their observed intensities were significantly lower than the calculated values, being apparently obscured by the beam stop.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Synthetic scheme, part 1.
[Figure 2] Fig. 2. Synthetic scheme, part 2.
[Figure 3] Fig. 3. Structure of molecules A and B present in the title compound (5) with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 4] Fig. 4. A least-squares fit of molecules A (blue) and B (red) within the asymmetric unit. The fitting fragment (the pyrene ring system) of the two molecules has an r.m.s. deviation of 0.035. Hydrogen atoms have been omitted for clarity.
(2E,4E,6E)-3-Methyl-7-(pyren-1-yl)octa-2,4,6-trienoic acid top
Crystal data top
C25H20O2Z = 4
Mr = 352.41F(000) = 744
Triclinic, P1Dx = 1.295 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5751 (7) ÅCell parameters from 4369 reflections
b = 8.5466 (7) Åθ = 3.0–30.3°
c = 28.458 (3) ŵ = 0.08 mm1
α = 97.086 (7)°T = 100 K
β = 93.003 (8)°Prism, colourless
γ = 97.574 (7)°0.21 × 0.17 × 0.14 mm
V = 1808.0 (3) Å3
Data collection top
Oxford Diffraction Xcalibur-3 with Sapphire CCD
diffractometer
3448 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray sourceRint = 0.109
Graphite monochromatorθmax = 25.0°, θmin = 3.0°
Detector resolution: 16.0288 pixels mm-1h = 99
ω and ϕ scansk = 910
22799 measured reflectionsl = 3333
6284 independent reflections
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0717P)2]
where P = (Fo2 + 2Fc2)/3
6284 reflections(Δ/σ)max < 0.001
497 parametersΔρmax = 0.33 e Å3
2 restraintsΔρmin = 0.35 e Å3
Crystal data top
C25H20O2γ = 97.574 (7)°
Mr = 352.41V = 1808.0 (3) Å3
Triclinic, P1Z = 4
a = 7.5751 (7) ÅMo Kα radiation
b = 8.5466 (7) ŵ = 0.08 mm1
c = 28.458 (3) ÅT = 100 K
α = 97.086 (7)°0.21 × 0.17 × 0.14 mm
β = 93.003 (8)°
Data collection top
Oxford Diffraction Xcalibur-3 with Sapphire CCD
diffractometer
3448 reflections with I > 2σ(I)
22799 measured reflectionsRint = 0.109
6284 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0662 restraints
wR(F2) = 0.160H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.33 e Å3
6284 reflectionsΔρmin = 0.35 e Å3
497 parameters
Special details top

Experimental. IR (KBr, cm-1): 3200–2610, 2937, 2849, 1674; HPLC (40% MeCN/H2O to 100% MeCN, C18, 3.5 µm, 150x4.6 mm): tR = 21.073 min; 1H–NMR (400 MHz, d6-DMSO): δ 12.12 (br. s, 1H), 8.30 (d, J = 7.2 Hz, 1H), 8.28 (d, J = 7.2 Hz, 2H), 8.18 (m, 4H) , 8.08 (t, J = 7.2 Hz, 1H), 7.95 (d, J = 8 Hz, 1H), 7.23 (dd, J = 11.2 and 15.2 Hz, 1H), 6.53 (d, J = 15.2 Hz, 1H), 6.39 (d, J = 11.2 Hz, 1H), 5.83 (s, 1H), 2.47 (s, 3H), 2.39 (s, 3H) p.p.m.; ESI-MS (30 eV): m/z 704.21 (2M), 353.37 (MH), 335.36 (MH—H2O).

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
C1A0.0508 (4)0.8362 (4)0.45141 (12)0.0247 (8)
C1B0.4808 (4)1.3280 (4)0.44843 (11)0.0243 (8)
C2A0.0917 (4)0.7231 (4)0.41240 (11)0.0247 (8)
H2A0.16730.76490.39090.030*
C2B0.4635 (4)1.2089 (4)0.40651 (11)0.0259 (8)
H2B0.40671.23540.37940.031*
C3A0.0344 (4)0.5659 (4)0.40331 (11)0.0225 (8)
C3B0.5198 (4)1.0650 (4)0.40221 (11)0.0241 (8)
C4A0.0898 (4)0.4799 (4)0.36041 (11)0.0233 (8)
H4A0.15640.54000.34070.028*
C4B0.4895 (4)0.9708 (4)0.35600 (11)0.0249 (8)
H4B0.43851.01790.33190.030*
C5A0.0542 (4)0.3227 (4)0.34658 (11)0.0225 (8)
H5A0.01070.26000.36600.027*
C5B0.5275 (4)0.8214 (4)0.34422 (11)0.0239 (8)
H5B0.57660.77010.36770.029*
C6A0.1115 (4)0.2460 (4)0.30317 (11)0.0243 (8)
H6A0.17180.31130.28360.029*
C6B0.4949 (4)0.7392 (4)0.29682 (11)0.0254 (8)
H6B0.45030.79520.27390.030*
C7A0.0858 (4)0.0887 (4)0.28832 (11)0.0210 (7)
C7B0.5226 (4)0.5888 (4)0.28218 (11)0.0231 (8)
C8A0.0034 (5)0.0307 (4)0.31727 (11)0.0316 (9)
H8A10.05300.01330.34880.047*
H8A20.00710.13630.30280.047*
H8A30.12740.01860.31860.047*
C8B0.5888 (4)0.4862 (4)0.31719 (11)0.0275 (8)
H8B10.71140.52460.32730.041*
H8B20.57880.37810.30230.041*
H8B30.51800.49090.34420.041*
C9A0.0803 (5)0.4746 (4)0.43400 (12)0.0331 (9)
H9A10.01100.40820.45000.050*
H9A20.17710.40920.41490.050*
H9A30.12720.54710.45700.050*
C9B0.6137 (5)0.9991 (4)0.44129 (12)0.0375 (10)
H9B10.63801.07900.46850.056*
H9B20.72400.96800.43090.056*
H9B30.53940.90810.44960.056*
C10A0.1586 (4)0.0308 (4)0.24283 (10)0.0202 (7)
C10B0.4752 (4)0.5222 (4)0.23171 (11)0.0209 (7)
C11A0.0509 (4)0.0710 (4)0.20581 (11)0.0195 (7)
C11B0.5854 (4)0.4329 (4)0.20344 (11)0.0190 (7)
C12A0.1353 (4)0.1213 (4)0.20822 (11)0.0216 (8)
H12A0.18950.09070.23580.026*
C12B0.7587 (4)0.4024 (4)0.22032 (11)0.0230 (8)
H12B0.80210.44400.25110.028*
C13A0.2351 (4)0.2122 (4)0.17156 (11)0.0230 (8)
H13A0.35520.24480.17500.028*
C13B0.8592 (4)0.3159 (4)0.19311 (11)0.0243 (8)
H13B0.96770.29510.20610.029*
C14A0.1619 (4)0.2593 (4)0.12809 (11)0.0214 (8)
C14B0.8048 (4)0.2547 (4)0.14485 (11)0.0228 (8)
C15A0.2625 (4)0.3479 (4)0.08916 (11)0.0235 (8)
H15A0.38260.38300.09180.028*
C15B0.9078 (4)0.1650 (4)0.11602 (11)0.0258 (8)
H15B1.01700.14340.12820.031*
C16A0.1880 (4)0.3848 (4)0.04670 (11)0.0276 (8)
H16A0.25860.44220.02090.033*
C16B0.8500 (4)0.1080 (4)0.06972 (12)0.0300 (9)
H16B0.92020.04800.05100.036*
C17A0.0082 (4)0.3366 (4)0.04229 (11)0.0268 (8)
H17A0.04080.36180.01350.032*
C17B0.6881 (5)0.1392 (4)0.05074 (12)0.0293 (8)
H17B0.65030.09890.01950.035*
C18A0.0999 (4)0.2508 (4)0.08053 (11)0.0220 (8)
C18B0.5813 (4)0.2301 (4)0.07801 (11)0.0232 (8)
C19A0.2858 (4)0.2031 (4)0.07779 (11)0.0255 (8)
H19A0.33870.23410.05000.031*
C19B0.4127 (4)0.2657 (4)0.05942 (12)0.0270 (8)
H19B0.37380.22830.02800.032*
C20A0.3873 (4)0.1144 (4)0.11424 (11)0.0254 (8)
H20A0.50810.08400.11100.030*
C20B0.3109 (4)0.3511 (4)0.08627 (11)0.0246 (8)
H20B0.20380.37350.07300.030*
C21A0.3126 (4)0.0664 (4)0.15760 (11)0.0209 (7)
C21B0.3634 (4)0.4090 (4)0.13516 (11)0.0218 (8)
C22A0.4134 (4)0.0312 (4)0.19507 (11)0.0222 (7)
H22A0.53410.06380.19240.027*
C22B0.2594 (4)0.4966 (4)0.16391 (11)0.0238 (8)
H22B0.15130.51940.15130.029*
C23A0.3358 (4)0.0796 (4)0.23598 (11)0.0214 (8)
H23A0.40520.14770.26000.026*
C23B0.3125 (4)0.5504 (4)0.21052 (11)0.0230 (8)
H23B0.23840.60750.22880.028*
C24A0.1296 (4)0.1163 (4)0.16294 (11)0.0194 (7)
C24B0.5297 (4)0.3771 (4)0.15525 (11)0.0189 (7)
C25A0.0224 (4)0.2094 (4)0.12396 (11)0.0195 (7)
C25B0.6370 (4)0.2868 (4)0.12604 (11)0.0210 (7)
O1A0.0314 (3)0.8043 (3)0.48587 (8)0.0293 (6)
O1B0.5355 (3)1.3133 (3)0.48846 (8)0.0316 (6)
O2A0.1129 (3)0.9852 (3)0.44623 (8)0.0320 (6)
H2A10.092 (5)1.054 (4)0.4701 (10)0.048*
O2B0.4270 (3)1.4636 (3)0.43819 (8)0.0342 (6)
H2B10.443 (5)1.520 (4)0.4655 (8)0.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.032 (2)0.019 (2)0.0256 (19)0.0097 (16)0.0007 (15)0.0053 (16)
C1B0.0243 (18)0.026 (2)0.0222 (19)0.0010 (16)0.0056 (14)0.0036 (16)
C2A0.0261 (18)0.024 (2)0.0265 (19)0.0080 (16)0.0072 (14)0.0059 (16)
C2B0.0264 (19)0.028 (2)0.0233 (18)0.0018 (16)0.0009 (14)0.0070 (16)
C3A0.0234 (18)0.019 (2)0.0263 (19)0.0057 (15)0.0008 (14)0.0034 (16)
C3B0.0202 (18)0.028 (2)0.0245 (18)0.0003 (15)0.0030 (14)0.0066 (16)
C4A0.0213 (18)0.026 (2)0.0245 (18)0.0070 (15)0.0061 (13)0.0064 (16)
C4B0.0233 (18)0.028 (2)0.0246 (18)0.0052 (16)0.0005 (14)0.0068 (16)
C5A0.0236 (18)0.020 (2)0.0232 (18)0.0024 (15)0.0013 (13)0.0013 (15)
C5B0.0217 (18)0.028 (2)0.0235 (18)0.0035 (16)0.0037 (13)0.0086 (16)
C6A0.0230 (18)0.029 (2)0.0230 (18)0.0053 (16)0.0030 (14)0.0065 (16)
C6B0.0232 (18)0.027 (2)0.0270 (19)0.0063 (16)0.0012 (14)0.0061 (16)
C7A0.0216 (18)0.020 (2)0.0232 (18)0.0058 (15)0.0032 (13)0.0058 (15)
C7B0.0204 (18)0.022 (2)0.0284 (19)0.0025 (15)0.0036 (14)0.0071 (16)
C8A0.039 (2)0.031 (2)0.0238 (19)0.0009 (18)0.0032 (15)0.0039 (17)
C8B0.034 (2)0.022 (2)0.0266 (19)0.0045 (16)0.0013 (15)0.0047 (16)
C9A0.038 (2)0.034 (2)0.0271 (19)0.0027 (18)0.0068 (16)0.0025 (17)
C9B0.047 (2)0.035 (2)0.031 (2)0.0151 (19)0.0033 (17)0.0005 (18)
C10A0.0211 (18)0.0209 (19)0.0197 (17)0.0050 (15)0.0022 (13)0.0047 (15)
C10B0.0226 (18)0.0126 (18)0.0274 (19)0.0003 (14)0.0008 (14)0.0054 (15)
C11A0.0235 (18)0.0146 (18)0.0222 (18)0.0061 (15)0.0023 (13)0.0054 (14)
C11B0.0196 (17)0.0115 (18)0.0261 (18)0.0002 (14)0.0041 (13)0.0054 (14)
C12A0.0225 (18)0.023 (2)0.0219 (18)0.0086 (15)0.0061 (14)0.0055 (15)
C12B0.0250 (18)0.020 (2)0.0225 (18)0.0004 (15)0.0018 (14)0.0031 (15)
C13A0.0198 (17)0.024 (2)0.0272 (19)0.0036 (15)0.0039 (14)0.0082 (16)
C13B0.0185 (18)0.024 (2)0.033 (2)0.0057 (15)0.0005 (14)0.0095 (16)
C14A0.0252 (19)0.0176 (19)0.0230 (18)0.0067 (15)0.0013 (14)0.0051 (15)
C14B0.0243 (18)0.0164 (19)0.0290 (19)0.0022 (15)0.0042 (14)0.0078 (15)
C15A0.0220 (18)0.0181 (19)0.0304 (19)0.0004 (15)0.0012 (14)0.0065 (15)
C15B0.0265 (19)0.022 (2)0.031 (2)0.0061 (16)0.0046 (15)0.0095 (16)
C16A0.031 (2)0.023 (2)0.027 (2)0.0039 (16)0.0041 (15)0.0002 (16)
C16B0.036 (2)0.023 (2)0.034 (2)0.0096 (17)0.0126 (16)0.0063 (17)
C17A0.035 (2)0.024 (2)0.0223 (19)0.0089 (17)0.0054 (15)0.0011 (15)
C17B0.041 (2)0.020 (2)0.0261 (19)0.0025 (17)0.0035 (16)0.0016 (16)
C18A0.0287 (19)0.0161 (19)0.0232 (18)0.0075 (15)0.0033 (14)0.0055 (15)
C18B0.0280 (19)0.0159 (19)0.0265 (19)0.0014 (15)0.0048 (14)0.0094 (15)
C19A0.0272 (19)0.027 (2)0.0260 (19)0.0119 (16)0.0093 (14)0.0081 (16)
C19B0.030 (2)0.023 (2)0.0264 (19)0.0019 (16)0.0045 (15)0.0058 (16)
C20A0.0243 (18)0.024 (2)0.031 (2)0.0096 (16)0.0095 (15)0.0082 (16)
C20B0.0233 (18)0.024 (2)0.0276 (19)0.0026 (16)0.0025 (14)0.0098 (16)
C21A0.0213 (18)0.0156 (18)0.0270 (18)0.0066 (15)0.0024 (14)0.0039 (15)
C21B0.0199 (18)0.0172 (19)0.0290 (19)0.0014 (15)0.0028 (14)0.0069 (15)
C22A0.0210 (17)0.0177 (19)0.0288 (19)0.0021 (15)0.0042 (14)0.0065 (15)
C22B0.0197 (18)0.020 (2)0.033 (2)0.0044 (15)0.0021 (14)0.0090 (16)
C23A0.0244 (19)0.0125 (18)0.0265 (18)0.0000 (15)0.0014 (14)0.0033 (15)
C23B0.0218 (18)0.0185 (19)0.0298 (19)0.0048 (15)0.0058 (14)0.0043 (15)
C24A0.0214 (18)0.0129 (18)0.0252 (18)0.0048 (14)0.0019 (14)0.0054 (14)
C24B0.0193 (17)0.0132 (18)0.0234 (18)0.0029 (14)0.0020 (13)0.0053 (14)
C25A0.0191 (17)0.0175 (19)0.0237 (18)0.0078 (14)0.0022 (13)0.0039 (14)
C25B0.0228 (18)0.0172 (19)0.0241 (18)0.0020 (15)0.0034 (14)0.0069 (15)
O1A0.0414 (15)0.0224 (14)0.0251 (13)0.0043 (11)0.0091 (11)0.0046 (11)
O1B0.0459 (15)0.0258 (15)0.0243 (13)0.0077 (12)0.0023 (11)0.0046 (11)
O2A0.0435 (15)0.0201 (15)0.0322 (15)0.0027 (12)0.0114 (11)0.0006 (11)
O2B0.0466 (15)0.0243 (15)0.0321 (14)0.0122 (12)0.0023 (12)0.0007 (11)
Geometric parameters (Å, º) top
C1A—O1A1.228 (4)C12A—C13A1.351 (4)
C1A—O2A1.327 (4)C12A—H12A0.9300
C1A—C2A1.454 (4)C12B—C13B1.340 (4)
C1B—O1B1.218 (4)C12B—H12B0.9300
C1B—O2B1.338 (4)C13A—C14A1.417 (4)
C1B—C2B1.458 (4)C13A—H13A0.9300
C2A—C3A1.345 (4)C13B—C14B1.427 (4)
C2A—H2A0.9300C13B—H13B0.9300
C2B—C3B1.347 (4)C14A—C15A1.390 (4)
C2B—H2B0.9300C14A—C25A1.421 (4)
C3A—C4A1.456 (4)C14B—C15B1.392 (4)
C3A—C9A1.482 (5)C14B—C25B1.426 (4)
C3B—C4B1.445 (4)C15A—C16A1.379 (4)
C3B—C9B1.496 (4)C15A—H15A0.9300
C4A—C5A1.340 (4)C15B—C16B1.375 (4)
C4A—H4A0.9300C15B—H15B0.9300
C4B—C5B1.352 (4)C16A—C17A1.387 (4)
C4B—H4B0.9300C16A—H16A0.9300
C5A—C6A1.441 (4)C16B—C17B1.385 (4)
C5A—H5A0.9300C16B—H16B0.9300
C5B—C6B1.435 (4)C17A—C18A1.395 (4)
C5B—H5B0.9300C17A—H17A0.9300
C6A—C7A1.344 (4)C17B—C18B1.395 (4)
C6A—H6A0.9300C17B—H17B0.9300
C6B—C7B1.348 (4)C18A—C25A1.421 (4)
C6B—H6B0.9300C18A—C19A1.423 (4)
C7A—C10A1.488 (4)C18B—C25B1.415 (4)
C7A—C8A1.504 (4)C18B—C19B1.441 (4)
C7B—C10B1.485 (4)C19A—C20A1.346 (4)
C7B—C8B1.514 (4)C19A—H19A0.9300
C8A—H8A10.9600C19B—C20B1.335 (4)
C8A—H8A20.9600C19B—H19B0.9300
C8A—H8A30.9600C20A—C21A1.422 (4)
C8B—H8B10.9600C20A—H20A0.9300
C8B—H8B20.9600C20B—C21B1.435 (4)
C8B—H8B30.9600C20B—H20B0.9300
C9A—H9A10.9600C21A—C22A1.394 (4)
C9A—H9A20.9600C21A—C24A1.418 (4)
C9A—H9A30.9600C21B—C22B1.387 (4)
C9B—H9B10.9600C21B—C24B1.429 (4)
C9B—H9B20.9600C22A—C23A1.374 (4)
C9B—H9B30.9600C22A—H22A0.9300
C10A—C23A1.384 (4)C22B—C23B1.370 (4)
C10A—C11A1.424 (4)C22B—H22B0.9300
C10B—C23B1.406 (4)C23A—H23A0.9300
C10B—C11B1.419 (4)C23B—H23B0.9300
C11A—C24A1.419 (4)C24A—C25A1.429 (4)
C11A—C12A1.427 (4)C24B—C25B1.423 (4)
C11B—C24B1.418 (4)O2A—H2A10.876 (18)
C11B—C12B1.442 (4)O2B—H2B10.858 (18)
O1A—C1A—O2A121.5 (3)C13B—C12B—H12B118.9
O1A—C1A—C2A126.4 (3)C11B—C12B—H12B118.9
O2A—C1A—C2A112.1 (3)C12A—C13A—C14A121.9 (3)
O1B—C1B—O2B121.5 (3)C12A—C13A—H13A119.0
O1B—C1B—C2B127.2 (3)C14A—C13A—H13A119.0
O2B—C1B—C2B111.2 (3)C12B—C13B—C14B121.9 (3)
C3A—C2A—C1A128.4 (3)C12B—C13B—H13B119.0
C3A—C2A—H2A115.8C14B—C13B—H13B119.0
C1A—C2A—H2A115.8C15A—C14A—C13A123.3 (3)
C3B—C2B—C1B127.9 (3)C15A—C14A—C25A118.8 (3)
C3B—C2B—H2B116.0C13A—C14A—C25A118.0 (3)
C1B—C2B—H2B116.0C15B—C14B—C25B119.4 (3)
C2A—C3A—C4A117.5 (3)C15B—C14B—C13B122.7 (3)
C2A—C3A—C9A124.5 (3)C25B—C14B—C13B117.9 (3)
C4A—C3A—C9A118.0 (3)C16A—C15A—C14A121.5 (3)
C2B—C3B—C4B116.8 (3)C16A—C15A—H15A119.3
C2B—C3B—C9B124.7 (3)C14A—C15A—H15A119.3
C4B—C3B—C9B118.5 (3)C16B—C15B—C14B120.8 (3)
C5A—C4A—C3A126.3 (3)C16B—C15B—H15B119.6
C5A—C4A—H4A116.8C14B—C15B—H15B119.6
C3A—C4A—H4A116.8C15A—C16A—C17A120.2 (3)
C5B—C4B—C3B126.8 (3)C15A—C16A—H16A119.9
C5B—C4B—H4B116.6C17A—C16A—H16A119.9
C3B—C4B—H4B116.6C15B—C16B—C17B120.6 (3)
C4A—C5A—C6A123.2 (3)C15B—C16B—H16B119.7
C4A—C5A—H5A118.4C17B—C16B—H16B119.7
C6A—C5A—H5A118.4C16A—C17A—C18A120.8 (3)
C4B—C5B—C6B122.3 (3)C16A—C17A—H17A119.6
C4B—C5B—H5B118.8C18A—C17A—H17A119.6
C6B—C5B—H5B118.8C16B—C17B—C18B120.8 (3)
C7A—C6A—C5A126.0 (3)C16B—C17B—H17B119.6
C7A—C6A—H6A117.0C18B—C17B—H17B119.6
C5A—C6A—H6A117.0C17A—C18A—C25A119.1 (3)
C7B—C6B—C5B126.5 (3)C17A—C18A—C19A122.4 (3)
C7B—C6B—H6B116.8C25A—C18A—C19A118.5 (3)
C5B—C6B—H6B116.8C17B—C18B—C25B119.3 (3)
C6A—C7A—C10A118.3 (3)C17B—C18B—C19B122.3 (3)
C6A—C7A—C8A122.5 (3)C25B—C18B—C19B118.3 (3)
C10A—C7A—C8A119.1 (3)C20A—C19A—C18A121.9 (3)
C6B—C7B—C10B118.7 (3)C20A—C19A—H19A119.1
C6B—C7B—C8B120.6 (3)C18A—C19A—H19A119.1
C10B—C7B—C8B120.6 (3)C20B—C19B—C18B121.5 (3)
C7A—C8A—H8A1109.5C20B—C19B—H19B119.3
C7A—C8A—H8A2109.5C18B—C19B—H19B119.3
H8A1—C8A—H8A2109.5C19A—C20A—C21A121.0 (3)
C7A—C8A—H8A3109.5C19A—C20A—H20A119.5
H8A1—C8A—H8A3109.5C21A—C20A—H20A119.5
H8A2—C8A—H8A3109.5C19B—C20B—C21B121.4 (3)
C7B—C8B—H8B1109.5C19B—C20B—H20B119.3
C7B—C8B—H8B2109.5C21B—C20B—H20B119.3
H8B1—C8B—H8B2109.5C22A—C21A—C24A118.6 (3)
C7B—C8B—H8B3109.5C22A—C21A—C20A121.9 (3)
H8B1—C8B—H8B3109.5C24A—C21A—C20A119.5 (3)
H8B2—C8B—H8B3109.5C22B—C21B—C24B118.2 (3)
C3A—C9A—H9A1109.5C22B—C21B—C20B122.5 (3)
C3A—C9A—H9A2109.5C24B—C21B—C20B119.2 (3)
H9A1—C9A—H9A2109.5C23A—C22A—C21A120.5 (3)
C3A—C9A—H9A3109.5C23A—C22A—H22A119.7
H9A1—C9A—H9A3109.5C21A—C22A—H22A119.7
H9A2—C9A—H9A3109.5C23B—C22B—C21B121.3 (3)
C3B—C9B—H9B1109.5C23B—C22B—H22B119.3
C3B—C9B—H9B2109.5C21B—C22B—H22B119.3
H9B1—C9B—H9B2109.5C22A—C23A—C10A122.5 (3)
C3B—C9B—H9B3109.5C22A—C23A—H23A118.7
H9B1—C9B—H9B3109.5C10A—C23A—H23A118.7
H9B2—C9B—H9B3109.5C22B—C23B—C10B122.3 (3)
C23A—C10A—C11A119.0 (3)C22B—C23B—H23B118.8
C23A—C10A—C7A118.9 (3)C10B—C23B—H23B118.8
C11A—C10A—C7A122.1 (3)C21A—C24A—C11A120.9 (3)
C23B—C10B—C11B118.0 (3)C21A—C24A—C25A119.2 (3)
C23B—C10B—C7B118.2 (3)C11A—C24A—C25A119.9 (3)
C11B—C10B—C7B123.8 (3)C11B—C24B—C25B120.8 (3)
C24A—C11A—C10A118.4 (3)C11B—C24B—C21B120.6 (3)
C24A—C11A—C12A118.0 (3)C25B—C24B—C21B118.6 (3)
C10A—C11A—C12A123.5 (3)C14A—C25A—C18A119.7 (3)
C24B—C11B—C10B119.5 (3)C14A—C25A—C24A120.4 (3)
C24B—C11B—C12B117.1 (3)C18A—C25A—C24A119.9 (3)
C10B—C11B—C12B123.3 (3)C18B—C25B—C24B121.0 (3)
C13A—C12A—C11A121.9 (3)C18B—C25B—C14B119.1 (3)
C13A—C12A—H12A119.1C24B—C25B—C14B120.0 (3)
C11A—C12A—H12A119.1C1A—O2A—H2A1113 (2)
C13B—C12B—C11B122.2 (3)C1B—O2B—H2B1101 (3)
O1A—C1A—C2A—C3A7.5 (5)C25A—C18A—C19A—C20A3.1 (5)
O2A—C1A—C2A—C3A172.4 (3)C17B—C18B—C19B—C20B179.0 (3)
O1B—C1B—C2B—C3B7.0 (6)C25B—C18B—C19B—C20B0.7 (5)
O2B—C1B—C2B—C3B173.2 (3)C18A—C19A—C20A—C21A1.0 (5)
C1A—C2A—C3A—C4A177.5 (3)C18B—C19B—C20B—C21B1.2 (5)
C1A—C2A—C3A—C9A2.7 (5)C19A—C20A—C21A—C22A177.2 (3)
C1B—C2B—C3B—C4B178.5 (3)C19A—C20A—C21A—C24A1.7 (5)
C1B—C2B—C3B—C9B0.1 (6)C19B—C20B—C21B—C22B179.4 (3)
C2A—C3A—C4A—C5A176.4 (3)C19B—C20B—C21B—C24B1.2 (5)
C9A—C3A—C4A—C5A3.4 (5)C24A—C21A—C22A—C23A0.9 (4)
C2B—C3B—C4B—C5B176.9 (3)C20A—C21A—C22A—C23A178.0 (3)
C9B—C3B—C4B—C5B4.4 (5)C24B—C21B—C22B—C23B0.7 (5)
C3A—C4A—C5A—C6A179.1 (3)C20B—C21B—C22B—C23B179.9 (3)
C3B—C4B—C5B—C6B178.8 (3)C21A—C22A—C23A—C10A2.2 (5)
C4A—C5A—C6A—C7A177.3 (3)C11A—C10A—C23A—C22A1.2 (5)
C4B—C5B—C6B—C7B177.5 (3)C7A—C10A—C23A—C22A179.8 (3)
C5A—C6A—C7A—C10A178.6 (3)C21B—C22B—C23B—C10B0.9 (5)
C5A—C6A—C7A—C8A2.3 (5)C11B—C10B—C23B—C22B0.9 (5)
C5B—C6B—C7B—C10B178.1 (3)C7B—C10B—C23B—C22B178.6 (3)
C5B—C6B—C7B—C8B2.2 (5)C22A—C21A—C24A—C11A1.3 (4)
C6A—C7A—C10A—C23A51.1 (4)C20A—C21A—C24A—C11A179.8 (3)
C8A—C7A—C10A—C23A125.3 (3)C22A—C21A—C24A—C25A176.8 (3)
C6A—C7A—C10A—C11A127.8 (3)C20A—C21A—C24A—C25A2.1 (4)
C8A—C7A—C10A—C11A55.8 (4)C10A—C11A—C24A—C21A2.3 (4)
C6B—C7B—C10B—C23B43.4 (4)C12A—C11A—C24A—C21A178.1 (3)
C8B—C7B—C10B—C23B132.5 (3)C10A—C11A—C24A—C25A175.8 (3)
C6B—C7B—C10B—C11B136.0 (3)C12A—C11A—C24A—C25A0.0 (4)
C8B—C7B—C10B—C11B48.1 (4)C10B—C11B—C24B—C25B179.8 (3)
C23A—C10A—C11A—C24A1.0 (4)C12B—C11B—C24B—C25B3.6 (4)
C7A—C10A—C11A—C24A177.9 (3)C10B—C11B—C24B—C21B0.5 (5)
C23A—C10A—C11A—C12A176.6 (3)C12B—C11B—C24B—C21B177.1 (3)
C7A—C10A—C11A—C12A2.3 (5)C22B—C21B—C24B—C11B0.5 (5)
C23B—C10B—C11B—C24B0.7 (5)C20B—C21B—C24B—C11B179.9 (3)
C7B—C10B—C11B—C24B178.8 (3)C22B—C21B—C24B—C25B179.8 (3)
C23B—C10B—C11B—C12B177.0 (3)C20B—C21B—C24B—C25B0.8 (5)
C7B—C10B—C11B—C12B2.4 (5)C15A—C14A—C25A—C18A0.1 (4)
C24A—C11A—C12A—C13A1.4 (4)C13A—C14A—C25A—C18A178.4 (3)
C10A—C11A—C12A—C13A177.0 (3)C15A—C14A—C25A—C24A179.1 (3)
C24B—C11B—C12B—C13B4.5 (5)C13A—C14A—C25A—C24A0.8 (4)
C10B—C11B—C12B—C13B179.1 (3)C17A—C18A—C25A—C14A1.6 (4)
C11A—C12A—C13A—C14A1.8 (5)C19A—C18A—C25A—C14A178.3 (3)
C11B—C12B—C13B—C14B3.0 (5)C17A—C18A—C25A—C24A177.6 (3)
C12A—C13A—C14A—C15A177.6 (3)C19A—C18A—C25A—C24A2.5 (4)
C12A—C13A—C14A—C25A0.7 (4)C21A—C24A—C25A—C14A179.2 (3)
C12B—C13B—C14B—C15B179.8 (3)C11A—C24A—C25A—C14A1.1 (4)
C12B—C13B—C14B—C25B0.7 (5)C21A—C24A—C25A—C18A0.0 (4)
C13A—C14A—C15A—C16A176.8 (3)C11A—C24A—C25A—C18A178.1 (3)
C25A—C14A—C15A—C16A1.4 (5)C17B—C18B—C25B—C24B178.7 (3)
C25B—C14B—C15B—C16B0.3 (5)C19B—C18B—C25B—C24B0.2 (5)
C13B—C14B—C15B—C16B179.8 (3)C17B—C18B—C25B—C14B2.5 (5)
C14A—C15A—C16A—C17A1.4 (5)C19B—C18B—C25B—C14B179.1 (3)
C14B—C15B—C16B—C17B0.2 (5)C11B—C24B—C25B—C18B179.6 (3)
C15A—C16A—C17A—C18A0.2 (5)C21B—C24B—C25B—C18B0.3 (5)
C15B—C16B—C17B—C18B0.6 (5)C11B—C24B—C25B—C14B1.5 (5)
C16A—C17A—C18A—C25A1.7 (5)C21B—C24B—C25B—C14B179.2 (3)
C16A—C17A—C18A—C19A178.2 (3)C15B—C14B—C25B—C18B1.7 (5)
C16B—C17B—C18B—C25B2.0 (5)C13B—C14B—C25B—C18B178.8 (3)
C16B—C17B—C18B—C19B179.7 (3)C15B—C14B—C25B—C24B179.5 (3)
C17A—C18A—C19A—C20A177.0 (3)C13B—C14B—C25B—C24B0.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2A1···O1Ai0.88 (2)1.76 (2)2.629 (3)174 (4)
O2B—H2B1···O1Bii0.86 (2)1.79 (2)2.624 (3)162 (4)
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+3, z+1.

Experimental details

Crystal data
Chemical formulaC25H20O2
Mr352.41
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.5751 (7), 8.5466 (7), 28.458 (3)
α, β, γ (°)97.086 (7), 93.003 (8), 97.574 (7)
V3)1808.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.21 × 0.17 × 0.14
Data collection
DiffractometerOxford Diffraction Xcalibur-3 with Sapphire CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
22799, 6284, 3448
Rint0.109
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.160, 1.00
No. of reflections6284
No. of parameters497
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.35

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2A—H2A1···O1Ai0.876 (18)1.756 (19)2.629 (3)174 (4)
O2B—H2B1···O1Bii0.858 (18)1.79 (2)2.624 (3)162 (4)
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+3, z+1.
 

References

First citationAltomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  CrossRef Web of Science IUCr Journals Google Scholar
First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationChaudhuri, B. N., Kleywegt, G. J., Broutin-L'Hermite, I., Bergfors, T., Senn, H., Le Motte, P., Partouche, O. & Jones, T. A. (1999). Acta Cryst. D55, 1850–1857.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationMalpezzi, L., Magnone, G. A., Masciocchi, N. & Sironi, A. (2005). J. Pharm. Sci. 94, 1067–1078.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationMeyer, H., Bollag, W., Hänni, R. & Rüegg, R. (1978). Experientia (Generalia), 34, 1105–1246.  Google Scholar
First citationOxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSporn, M. B., Roberts, A. B. & Goodman, D. S. (1994). Editors. The Retinoids – Biology, Chemistry and Medicine, 2nd ed. New York: Raven Press.  Google Scholar
First citationTian, K., Norris, A. W., Lin, C.-L. S. & Li, E. (1997). Biochemistry, 36, 5669–5676.  CrossRef CAS PubMed Web of Science Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds