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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 12| December 2014| Pages o1239-o1240

Crystal structure of hydro­cortisone 17-butyrate

aCollege of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001, People's Republic of China
*Correspondence e-mail: zhuyu@zzu.edu.cn

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 21 October 2014; accepted 30 October 2014; online 5 November 2014)

In the title compound, C25H36O6, the two central cyclo­hexane rings exhibit a chair conformation. The terminal cyclo­hexene and cyclo­pentane rings are in half-chair and envelope conformations (with the C atom bearing the methyl substit­uent as the flap), respectively. The methyl group of the butyrate chain is disordered over two orientations, with a refined occupancy ratio of 0.742 (6):0.258 (6). Intra­molecular O—H⋯O and C—H⋯O hydrogen bonds are observed. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds into chains running parallel to the a axis.

1. Related literature

For the pharmacological activities of the title compound, see: Haapasaari et al. (1995[Haapasaari, K. M., Risteli, J., Koivukangas, V. & Oikarinen, A. (1995). Acta Derm. Venereol. 75, 269-271.]); Lerche et al. (2010[Lerche, C. M., Philipsen, P. A., Poulsen, T. & Wulf, H. C. (2010). Exp. Dermatol. 19, 973-979.]); D'Erme & Gola (2012[D'Erme, A. M. & Gola, M. (2012). Dermatitis, 23, 95-96.]). For the synthesis of the title compound, see: Sun et al. (2009[Sun, L., Chen, S. & Zhao, L. (2009). China Patent CN 101812108A.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C25H36O6

  • Mr = 432.54

  • Orthorhombic, P 21 21 21

  • a = 9.05738 (8) Å

  • b = 11.87633 (9) Å

  • c = 21.13465 (15) Å

  • V = 2273.42 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.72 mm−1

  • T = 291 K

  • 0.22 × 0.2 × 0.2 mm

2.2. Data collection

  • Agilent Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]) Tmin = 0.952, Tmax = 1.000

  • 23353 measured reflections

  • 4496 independent reflections

  • 4389 reflections with I > 2σ(I)

  • Rint = 0.021

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.111

  • S = 1.06

  • 4496 reflections

  • 301 parameters

  • 4 restraints

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

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.28 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1932 Friedel pairs

  • Absolute structure parameter: 0.02 (18)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C19—H19C⋯O2 0.96 2.39 3.016 (2) 122
O4—H4⋯O3 0.83 (3) 2.06 (3) 2.629 (3) 126 (2)
O2—H2⋯O1i 0.82 2.11 2.9192 (18) 169
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.

Supporting information


Comment top

Hydrocortisone 17-butyrate is an important cortical hormone drug derived from the esterification reaction of hydrocortisone at the hydroxyl group of C-17. Due to the introduction of the alkyl chain, hydrocortisone 17-butyrate showed increased lipophicity and affinity for receptors, which lead to increased pharmacological activity (Haapasaari et al., 1995; Lerche et al., 2010; D'Erme & Gola, 2012). Compared with hydrocortisone, it showed increased anti-inflammatory activity, immunosuppressive properties, and low side effect. Due to the outstanding characteristics of hydrocortisone 17-butyrate, it has drawn great attention of the experts from the fields of chemistry, pharmacy and medicine. The synthesis and properties have been investigated quite extensively, while its molecular structure has not been reported. Here we present the single-crystal X-ray diffraction study of hydrocortisone 17-butyrate.

The molecular structure of the title compound is shown in Figure 1. As expected, the chiral carbon atoms C8, C9, C11, C13, and C14 exhibit S configuration, and atoms C10 and C17 exhibit R configuration. The Flack parameter is 0.02 (18). Both central six membered rings (C5, C6, C7, C8, C9, C10, and C8, C9, C11, C12, C13, C14) exhibit chair conformation, with atoms C5 and C8 displaced by 0.6024 (16) and 0.6378 (15) Å on opposite sides from the C6, C7, C9 and C10 plane, and atoms C9 and C13 by 0.6249 (14) and 0.7014 (15) Å from the C8, C11, C12 and C14 plane. The cyclohexene ring (C1, C2, C3, C4, C5, C10) assumes a half-chair conformation, atom C2 protruding by 0.534 (2) Å from the mean plane through the remaining five atoms. The cyclopentane ring is in an envelope conformation, with atom C13 displaced by 0.6761 (15) Å from the C14, C15, C16, C17 mean plane. Intramolecular O—H···O and C—H···O hydrogen bonds are observed (Table 1). In the crystal, molecules are connected by intermolecular O—H···O hydrogen bonds to form chains parallel to the a axis.

Related literature top

For the pharmacological activities of the title compound, see: Haapasaari et al. (1995); Lerche et al. (2010); D'Erme & Gola (2012). For the synthesis of the title compound, see: Sun et al. (2009).

Experimental top

The title compound was obtained following a patent report (Sun et al., 2009). At 0-5°C, butyryl chloride (1.5 mmol, 0.16 mL) was added dropwise to a CH2Cl2 (10 mL) solution containing hydrocortisone 21-acetate (1 mmol, 0.4 g), Et3N (4 mL) and 4-dimethylaminopyridine (0.05 mmol, 6 mg). The mixture was then stirred at 0°C for 3 hours before being treated with HCl to reach a pH of 2. The mixture was then washed with H2O to reach neutrality, and extracted using CH2Cl2. The organic phase was combined, dried, and evaporated. Crystallization of the residue in MeOH produced hydrocortisone 17-butyrate 21-acetate. The CH2Cl2 solution of hydrocortisone 17-butyrate 21-acetate was added slowly to a MeOH (10 mL) solution of K2CO3 (0.1 g) at -10°C for selective hydrolysis. The mixture was then neutralized by CH3COOH, washed with H2O, and extracted with CH2Cl2. The organic phase was combined, dried and evaporated. Crystallization of the residue in MeOH at 0°C produced pure hydrocortisone 17-butyrate. Crystals suitable for X-ray analysis were obtained by slow evaporation of a MeOH (20 mL) solution of hydrocortisone 17-butyrate (5 mg) at room temperature.

Refinement top

The C25 methyl carbon atom is disordered over two orientations with refined occupancy ratio 0.742 (6):0.258 (6). The disordered atoms were refined by constraining the C24–C25 and C24–C25A bond lengths to be 1.52 (1) Å and by restraining the anisotropic displacement ellipsoids to be equal. The hydroxyl H atom bound to O4 was located in a difference Fourier map and refined freely. All other H atoms were placed in calculated positions and refined as riding, with C—H = 0.93–0.97 Å, O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl and hydroxyl H atoms. A rotating model was applied to the methyl and hydroxyl groups. One outlier (0 1 1) was omitted in the last cycles of refinement.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids. Only the major component of the disordered C25 methyl group is shown
(8S,9S,10R,11S,13S,14S,17R)-11-Hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl butanoate top
Crystal data top
C25H36O6Dx = 1.264 Mg m3
Mr = 432.54Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 14007 reflections
a = 9.05738 (8) Åθ = 4.2–72.4°
b = 11.87633 (9) ŵ = 0.72 mm1
c = 21.13465 (15) ÅT = 291 K
V = 2273.42 (3) Å3Block, colourless
Z = 40.22 × 0.2 × 0.2 mm
F(000) = 936
Data collection top
Agilent Xcalibur Eos Gemini
diffractometer
4496 independent reflections
Radiation source: Enhance (Cu) X-ray Source4389 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 16.2312 pixels mm-1θmax = 72.3°, θmin = 4.2°
ω scansh = 911
Absorption correction: multi-scan
(CrysAlis PRO (Agilent, 2011)
k = 1414
Tmin = 0.952, Tmax = 1.000l = 2626
23353 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0712P)2 + 0.3126P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4496 reflectionsΔρmax = 0.31 e Å3
301 parametersΔρmin = 0.28 e Å3
4 restraintsAbsolute structure: Flack (1983), 1932 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (18)
Crystal data top
C25H36O6V = 2273.42 (3) Å3
Mr = 432.54Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 9.05738 (8) ŵ = 0.72 mm1
b = 11.87633 (9) ÅT = 291 K
c = 21.13465 (15) Å0.22 × 0.2 × 0.2 mm
Data collection top
Agilent Xcalibur Eos Gemini
diffractometer
4496 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO (Agilent, 2011)
4389 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 1.000Rint = 0.021
23353 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111Δρmax = 0.31 e Å3
S = 1.06Δρmin = 0.28 e Å3
4496 reflectionsAbsolute structure: Flack (1983), 1932 Friedel pairs
301 parametersAbsolute structure parameter: 0.02 (18)
4 restraints
Special details top

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*/UeqOcc. (<1)
O10.36156 (14)0.73133 (12)0.93301 (6)0.0499 (3)
O20.38389 (14)0.61706 (12)0.87774 (6)0.0468 (3)
H20.45120.65720.89060.070*
O30.70484 (17)0.51666 (13)0.64786 (8)0.0624 (4)
O40.8532 (2)0.7026 (2)0.67034 (11)0.0791 (5)
H40.866 (3)0.638 (2)0.6577 (13)0.059 (7)*
O50.39480 (15)0.69247 (10)0.63513 (5)0.0448 (3)
O60.5163 (2)0.66663 (14)0.54407 (7)0.0670 (4)
C10.02943 (18)0.72375 (15)0.90894 (8)0.0409 (3)
H1A0.11770.74720.93140.049*
H1B0.01420.77590.87430.049*
C20.1022 (2)0.73130 (18)0.95395 (9)0.0483 (4)
H2A0.08310.68600.99120.058*
H2B0.11540.80870.96740.058*
C30.24009 (18)0.69069 (14)0.92219 (7)0.0391 (3)
C40.22232 (18)0.59526 (15)0.87958 (8)0.0408 (3)
H4A0.30710.56210.86320.049*
C50.09161 (18)0.55240 (13)0.86262 (7)0.0373 (3)
C60.0827 (2)0.44526 (14)0.82502 (9)0.0453 (4)
H6A0.18140.42250.81260.054*
H6B0.04150.38620.85130.054*
C70.0122 (2)0.45906 (15)0.76617 (9)0.0440 (4)
H7A0.03780.50870.73670.053*
H7B0.02370.38640.74580.053*
C80.16479 (17)0.50722 (13)0.78101 (7)0.0336 (3)
H80.22170.45160.80510.040*
C90.15146 (16)0.61680 (12)0.82020 (7)0.0311 (3)
H90.09570.66840.79300.037*
C100.05504 (16)0.60493 (14)0.88151 (7)0.0339 (3)
C110.30159 (18)0.67602 (13)0.83072 (7)0.0355 (3)
H110.28130.75170.84710.043*
C120.39077 (18)0.68924 (12)0.76887 (7)0.0352 (3)
H12A0.34400.74610.74270.042*
H12B0.48930.71560.77910.042*
C130.40305 (17)0.57970 (12)0.73084 (7)0.0336 (3)
C140.24614 (18)0.53463 (12)0.71963 (7)0.0340 (3)
H140.19060.59510.69890.041*
C150.2669 (2)0.44163 (14)0.67029 (8)0.0438 (4)
H15A0.17730.43070.64590.053*
H15B0.29340.37100.69030.053*
C160.3930 (2)0.48456 (16)0.62797 (8)0.0483 (4)
H16A0.35560.50390.58640.058*
H16B0.46790.42680.62320.058*
C170.4592 (2)0.58969 (13)0.66039 (7)0.0388 (3)
C180.1214 (2)0.52665 (18)0.93282 (8)0.0505 (4)
H18A0.04630.50730.96300.076*
H18B0.20070.56480.95400.076*
H18C0.15830.45930.91330.076*
C190.5017 (2)0.49307 (15)0.76391 (8)0.0423 (4)
H19A0.59890.52390.76930.063*
H19B0.50730.42610.73860.063*
H19C0.46070.47500.80450.063*
C200.6275 (2)0.59745 (15)0.65638 (8)0.0460 (4)
C210.7000 (3)0.7106 (2)0.66925 (12)0.0609 (5)
H21A0.672 (3)0.740 (3)0.7116 (14)0.076 (8)*
H21B0.656 (4)0.773 (3)0.6395 (17)0.100 (11)*
C220.4291 (3)0.71949 (17)0.57472 (9)0.0525 (5)
C230.3459 (4)0.8215 (2)0.55363 (12)0.0835 (8)
H23A0.24140.80360.55350.100*
H23B0.36120.88070.58460.100*
C240.3861 (5)0.8661 (3)0.49010 (13)0.0950 (10)
H24A0.39020.80410.46020.114*0.742 (6)
H24B0.30980.91760.47600.114*0.742 (6)
H24C0.47560.82700.47760.114*0.258 (6)
H24D0.30930.84100.46140.114*0.258 (6)
C250.5263 (6)0.9239 (4)0.4900 (2)0.1017 (15)0.742 (6)
H25A0.51900.99100.51510.153*0.742 (6)
H25B0.55220.94360.44740.153*0.742 (6)
H25C0.60080.87550.50740.153*0.742 (6)
C25A0.4109 (19)0.9858 (11)0.4760 (7)0.1017 (15)0.258 (6)
H25D0.32631.01590.45450.153*0.258 (6)
H25E0.49650.99350.44960.153*0.258 (6)
H25F0.42621.02630.51480.153*0.258 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0363 (6)0.0593 (7)0.0543 (7)0.0030 (5)0.0045 (5)0.0085 (6)
O20.0376 (6)0.0639 (8)0.0387 (6)0.0106 (6)0.0084 (5)0.0032 (5)
O30.0531 (8)0.0558 (8)0.0784 (10)0.0067 (6)0.0191 (7)0.0034 (7)
O40.0565 (9)0.0848 (13)0.0961 (14)0.0210 (9)0.0018 (9)0.0035 (11)
O50.0565 (7)0.0433 (6)0.0346 (5)0.0032 (5)0.0059 (5)0.0017 (5)
O60.0899 (12)0.0657 (9)0.0454 (7)0.0036 (8)0.0209 (8)0.0014 (7)
C10.0325 (7)0.0491 (9)0.0411 (8)0.0043 (6)0.0009 (6)0.0120 (7)
C20.0396 (9)0.0630 (11)0.0424 (8)0.0048 (8)0.0017 (7)0.0162 (8)
C30.0339 (8)0.0467 (9)0.0367 (7)0.0017 (6)0.0030 (6)0.0003 (6)
C40.0315 (7)0.0467 (8)0.0443 (8)0.0054 (7)0.0030 (6)0.0040 (7)
C50.0348 (8)0.0376 (7)0.0395 (7)0.0034 (6)0.0011 (6)0.0012 (6)
C60.0357 (8)0.0385 (8)0.0618 (10)0.0092 (7)0.0071 (7)0.0071 (8)
C70.0400 (9)0.0414 (8)0.0505 (9)0.0077 (7)0.0009 (7)0.0115 (7)
C80.0341 (7)0.0305 (6)0.0363 (7)0.0022 (6)0.0002 (6)0.0014 (6)
C90.0317 (7)0.0300 (6)0.0317 (6)0.0007 (5)0.0030 (5)0.0010 (5)
C100.0288 (7)0.0407 (8)0.0324 (7)0.0001 (6)0.0025 (5)0.0013 (6)
C110.0371 (8)0.0354 (7)0.0340 (7)0.0057 (6)0.0000 (6)0.0054 (6)
C120.0389 (8)0.0298 (7)0.0369 (7)0.0061 (6)0.0028 (6)0.0044 (6)
C130.0364 (7)0.0309 (7)0.0336 (7)0.0027 (6)0.0019 (6)0.0031 (6)
C140.0386 (8)0.0302 (7)0.0332 (7)0.0023 (6)0.0029 (6)0.0021 (5)
C150.0508 (9)0.0395 (8)0.0410 (8)0.0078 (7)0.0012 (7)0.0106 (7)
C160.0569 (10)0.0461 (9)0.0418 (8)0.0085 (8)0.0066 (8)0.0141 (7)
C170.0472 (9)0.0338 (7)0.0353 (7)0.0016 (7)0.0050 (6)0.0047 (6)
C180.0401 (9)0.0691 (12)0.0422 (8)0.0010 (8)0.0015 (7)0.0187 (8)
C190.0439 (9)0.0392 (8)0.0438 (8)0.0031 (7)0.0041 (7)0.0021 (7)
C200.0509 (10)0.0455 (9)0.0417 (8)0.0044 (8)0.0107 (7)0.0035 (7)
C210.0530 (11)0.0623 (12)0.0675 (13)0.0153 (10)0.0141 (10)0.0139 (10)
C220.0687 (12)0.0512 (10)0.0375 (8)0.0054 (9)0.0054 (8)0.0015 (7)
C230.123 (2)0.0740 (15)0.0538 (12)0.0197 (16)0.0049 (14)0.0188 (11)
C240.146 (3)0.0853 (19)0.0542 (13)0.007 (2)0.0056 (17)0.0197 (12)
C250.112 (4)0.098 (3)0.096 (3)0.031 (3)0.003 (3)0.017 (2)
C25A0.112 (4)0.098 (3)0.096 (3)0.031 (3)0.003 (3)0.017 (2)
Geometric parameters (Å, º) top
O1—C31.223 (2)C12—C131.5332 (19)
O2—H20.8200C13—C141.537 (2)
O2—C111.426 (2)C13—C171.578 (2)
O3—C201.202 (2)C13—C191.531 (2)
O4—H40.83 (3)C14—H140.9800
O4—C211.391 (3)C14—C151.531 (2)
O5—C171.454 (2)C15—H15A0.9700
O5—C221.353 (2)C15—H15B0.9700
O6—C221.199 (3)C15—C161.538 (3)
C1—H1A0.9700C16—H16A0.9700
C1—H1B0.9700C16—H16B0.9700
C1—C21.528 (2)C16—C171.545 (2)
C1—C101.543 (2)C17—C201.530 (3)
C2—H2A0.9700C18—H18A0.9600
C2—H2B0.9700C18—H18B0.9600
C2—C31.497 (2)C18—H18C0.9600
C3—C41.457 (2)C19—H19A0.9600
C4—H4A0.9300C19—H19B0.9600
C4—C51.338 (2)C19—H19C0.9600
C5—C61.502 (2)C20—C211.520 (3)
C5—C101.521 (2)C21—H21A1.00 (3)
C6—H6A0.9700C21—H21B1.05 (4)
C6—H6B0.9700C22—C231.495 (3)
C6—C71.521 (3)C23—H23A0.9700
C7—H7A0.9700C23—H23B0.9700
C7—H7B0.9700C23—C241.488 (4)
C7—C81.528 (2)C24—H24A0.9700
C8—H80.9800C24—H24B0.9700
C8—C91.5473 (19)C24—H24C0.9700
C8—C141.527 (2)C24—H24D0.9700
C9—H90.9800C24—C251.443 (6)
C9—C101.569 (2)C24—C25A1.470 (12)
C9—C111.547 (2)C25—H25A0.9600
C10—C181.550 (2)C25—H25B0.9600
C11—H110.9800C25—H25C0.9600
C11—C121.545 (2)C25A—H25D0.9600
C12—H12A0.9700C25A—H25E0.9600
C12—H12B0.9700C25A—H25F0.9600
C11—O2—H2109.5C14—C15—H15A110.9
C21—O4—H4101 (2)C14—C15—H15B110.9
C22—O5—C17116.96 (14)C14—C15—C16104.36 (13)
H1A—C1—H1B107.7H15A—C15—H15B108.9
C2—C1—H1A108.8C16—C15—H15A110.9
C2—C1—H1B108.8C16—C15—H15B110.9
C2—C1—C10113.88 (15)C15—C16—H16A110.2
C10—C1—H1A108.8C15—C16—H16B110.2
C10—C1—H1B108.8C15—C16—C17107.35 (13)
C1—C2—H2A109.5H16A—C16—H16B108.5
C1—C2—H2B109.5C17—C16—H16A110.2
H2A—C2—H2B108.1C17—C16—H16B110.2
C3—C2—C1110.66 (13)O5—C17—C13106.28 (12)
C3—C2—H2A109.5O5—C17—C16111.11 (14)
C3—C2—H2B109.5O5—C17—C20109.19 (14)
O1—C3—C2122.63 (15)C16—C17—C13103.46 (13)
O1—C3—C4121.47 (15)C20—C17—C13112.19 (14)
C4—C3—C2115.82 (15)C20—C17—C16114.24 (14)
C3—C4—H4A118.0C10—C18—H18A109.5
C5—C4—C3124.03 (15)C10—C18—H18B109.5
C5—C4—H4A118.0C10—C18—H18C109.5
C4—C5—C6120.77 (15)H18A—C18—H18B109.5
C4—C5—C10123.13 (14)H18A—C18—H18C109.5
C6—C5—C10116.07 (14)H18B—C18—H18C109.5
C5—C6—H6A109.3C13—C19—H19A109.5
C5—C6—H6B109.3C13—C19—H19B109.5
C5—C6—C7111.82 (14)C13—C19—H19C109.5
H6A—C6—H6B107.9H19A—C19—H19B109.5
C7—C6—H6A109.3H19A—C19—H19C109.5
C7—C6—H6B109.3H19B—C19—H19C109.5
C6—C7—H7A109.1O3—C20—C17122.78 (17)
C6—C7—H7B109.1O3—C20—C21118.72 (18)
C6—C7—C8112.56 (14)C21—C20—C17118.30 (16)
H7A—C7—H7B107.8O4—C21—C20112.0 (2)
C8—C7—H7A109.1O4—C21—H21A105.3 (18)
C8—C7—H7B109.1O4—C21—H21B115.8 (19)
C7—C8—H8109.3C20—C21—H21A111.5 (17)
C7—C8—C9110.74 (13)C20—C21—H21B111 (2)
C9—C8—H8109.3H21A—C21—H21B101 (3)
C14—C8—C7109.98 (13)O5—C22—C23110.96 (18)
C14—C8—H8109.3O6—C22—O5122.50 (19)
C14—C8—C9108.24 (11)O6—C22—C23126.5 (2)
C8—C9—H9104.7C22—C23—H23A108.4
C8—C9—C10114.20 (12)C22—C23—H23B108.4
C10—C9—H9104.7H23A—C23—H23B107.4
C11—C9—C8113.00 (12)C24—C23—C22115.7 (3)
C11—C9—H9104.7C24—C23—H23A108.4
C11—C9—C10114.29 (12)C24—C23—H23B108.4
C1—C10—C9108.16 (12)C23—C24—H24A109.0
C1—C10—C18110.12 (14)C23—C24—H24B109.0
C5—C10—C1110.03 (13)C23—C24—H24C106.2
C5—C10—C9107.82 (12)C23—C24—H24D106.2
C5—C10—C18106.05 (13)H24A—C24—H24B107.8
C18—C10—C9114.58 (13)H24A—C24—H24C55.2
O2—C11—C9109.66 (12)H24A—C24—H24D52.2
O2—C11—H11107.6H24B—C24—H24C144.4
O2—C11—C12111.49 (13)H24B—C24—H24D59.4
C9—C11—H11107.6H24C—C24—H24D106.4
C12—C11—C9112.59 (12)C25—C24—C23112.7 (3)
C12—C11—H11107.6C25—C24—H24A109.0
C11—C12—H12A108.9C25—C24—H24B109.0
C11—C12—H12B108.9C25—C24—H24C59.5
H12A—C12—H12B107.7C25—C24—H24D140.9
C13—C12—C11113.29 (12)C25—C24—C25A53.5 (7)
C13—C12—H12A108.9C25A—C24—C23124.3 (7)
C13—C12—H12B108.9C25A—C24—H24A126.6
C12—C13—C14108.01 (12)C25A—C24—H24B55.7
C12—C13—C17117.02 (12)C25A—C24—H24C106.2
C14—C13—C17100.28 (12)C25A—C24—H24D106.2
C19—C13—C12111.91 (13)C24—C25—H25A109.5
C19—C13—C14112.07 (12)C24—C25—H25B109.5
C19—C13—C17107.06 (13)C24—C25—H25C109.5
C8—C14—C13112.92 (12)C24—C25A—H25D109.5
C8—C14—H14106.7C24—C25A—H25E109.5
C8—C14—C15118.96 (13)C24—C25A—H25F109.5
C13—C14—H14106.7H25D—C25A—H25E109.5
C15—C14—C13104.06 (13)H25D—C25A—H25F109.5
C15—C14—H14106.7H25E—C25A—H25F109.5
O1—C3—C4—C5175.19 (17)C10—C9—C11—C12178.22 (13)
O2—C11—C12—C1374.10 (17)C11—C9—C10—C157.46 (16)
O3—C20—C21—O41.1 (3)C11—C9—C10—C5176.41 (12)
O5—C17—C20—O3147.68 (18)C11—C9—C10—C1865.79 (18)
O5—C17—C20—C2137.6 (2)C11—C12—C13—C1454.22 (17)
O5—C22—C23—C24174.0 (3)C11—C12—C13—C17166.34 (14)
O6—C22—C23—C245.4 (5)C11—C12—C13—C1969.61 (18)
C1—C2—C3—O1145.75 (18)C12—C13—C14—C861.36 (15)
C1—C2—C3—C437.2 (2)C12—C13—C14—C15168.27 (12)
C2—C1—C10—C542.57 (18)C12—C13—C17—O537.73 (19)
C2—C1—C10—C9160.11 (14)C12—C13—C17—C16154.84 (15)
C2—C1—C10—C1873.98 (18)C12—C13—C17—C2081.54 (18)
C2—C3—C4—C57.8 (3)C13—C14—C15—C1634.65 (17)
C3—C4—C5—C6172.34 (16)C13—C17—C20—O394.8 (2)
C3—C4—C5—C105.4 (3)C13—C17—C20—C2180.0 (2)
C4—C5—C6—C7127.75 (18)C14—C8—C9—C10173.70 (12)
C4—C5—C10—C112.2 (2)C14—C8—C9—C1153.41 (16)
C4—C5—C10—C9130.00 (16)C14—C13—C17—O578.71 (13)
C4—C5—C10—C18106.83 (19)C14—C13—C17—C1638.40 (15)
C5—C6—C7—C852.7 (2)C14—C13—C17—C20162.02 (13)
C6—C5—C10—C1169.87 (14)C14—C15—C16—C179.6 (2)
C6—C5—C10—C952.12 (18)C15—C16—C17—O595.58 (17)
C6—C5—C10—C1871.05 (18)C15—C16—C17—C1318.09 (19)
C6—C7—C8—C952.40 (19)C15—C16—C17—C20140.35 (17)
C6—C7—C8—C14171.99 (14)C16—C17—C20—O322.6 (3)
C7—C8—C9—C1053.07 (17)C16—C17—C20—C21162.70 (18)
C7—C8—C9—C11174.04 (13)C17—O5—C22—O65.1 (3)
C7—C8—C14—C13177.98 (13)C17—O5—C22—C23175.4 (2)
C7—C8—C14—C1555.61 (19)C17—C13—C14—C8175.66 (12)
C8—C9—C10—C1170.26 (12)C17—C13—C14—C1545.28 (14)
C8—C9—C10—C551.30 (16)C17—C20—C21—O4173.85 (19)
C8—C9—C10—C1866.49 (17)C19—C13—C14—C862.37 (16)
C8—C9—C11—O275.82 (15)C19—C13—C14—C1568.01 (16)
C8—C9—C11—C1248.93 (17)C19—C13—C17—O5164.22 (13)
C8—C14—C15—C16161.34 (15)C19—C13—C17—C1678.68 (16)
C9—C8—C14—C1360.92 (15)C19—C13—C17—C2044.94 (17)
C9—C8—C14—C15176.71 (14)C22—O5—C17—C13179.33 (15)
C9—C11—C12—C1349.64 (18)C22—O5—C17—C1668.78 (19)
C10—C1—C2—C355.8 (2)C22—O5—C17—C2058.11 (19)
C10—C5—C6—C754.3 (2)C22—C23—C24—C2574.3 (4)
C10—C9—C11—O257.03 (16)C22—C23—C24—C25A134.6 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19C···O20.962.393.016 (2)122
O4—H4···O30.83 (3)2.06 (3)2.629 (3)126 (2)
O2—H2···O1i0.822.112.9192 (18)169
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19C···O20.962.393.016 (2)122.2
O4—H4···O30.83 (3)2.06 (3)2.629 (3)126 (2)
O2—H2···O1i0.822.112.9192 (18)168.6
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

The authors thank Ms L. R. Yang for technical assistance. This research was supported by the National Natural Science Foundation of China (No. JI210060).

References

First citationAgilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.  Google Scholar
First citationD'Erme, A. M. & Gola, M. (2012). Dermatitis, 23, 95–96.  PubMed Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHaapasaari, K. M., Risteli, J., Koivukangas, V. & Oikarinen, A. (1995). Acta Derm. Venereol. 75, 269–271.  CAS PubMed Google Scholar
First citationLerche, C. M., Philipsen, P. A., Poulsen, T. & Wulf, H. C. (2010). Exp. Dermatol. 19, 973–979.  Web of Science CrossRef CAS PubMed Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSun, L., Chen, S. & Zhao, L. (2009). China Patent CN 101812108A.  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
Volume 70| Part 12| December 2014| Pages o1239-o1240
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds