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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 4| April 2009| Pages o881-o882

(E)-1-(4-Decyl­oxyphen­yl)-3-(4-hy­droxy­phen­yl)prop-2-en-1-one

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and cDepartment of Molecular Biology, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia
*Correspondence e-mail: arazaki@usm.my

(Received 18 March 2009; accepted 23 March 2009; online 28 March 2009)

In the title compound, C25H32O3, the asymmetric unit contains two crystallographically independent mol­ecules: both enone groups adopt an s-cis configuration. In the crystal, O—H⋯O and C—H⋯O inter­molecular inter­actions form bifurcated hydrogen bonds, which generate R12(6) ring motifs. These inter­molecular inter­actions link the mol­ecules into one-dimensional chains along the [10[\overline{1}]] direction. The crystal structure is further stabilized by C—H⋯π inter­actions.

Related literature

For general background to the biological properties of chalcone derivatives, see: Bhat et al. (2005[Bhat, B. A., Dhar, K. L., Puri, S. C., Saxena, A. K., Shanmugavel, M. & Qazi, G. N. (2005). Bioorg. Med. Chem. Lett. 15, 3177-3180.]); Xue et al. (2004[Xue, C. X., Cui, S. Y., Liu, M. C., Hu, Z. D. & Fan, B. T. (2004). Eur. J. Med. Chem. 39, 745-753.]); Satyanarayana et al. (2004[Satyanarayana, M., Tiwari, P., Tripathi, B. K., Srivastava, A. K. & Pratap, R. (2004). Bioorg. Med. Chem. Lett. 12, 883-889.]); Zhao et al. (2005[Zhao, L. M., Jin, H. S., Sun, L. P., Piao, H. R. & Quan, Z. S. (2005). Chem. Lett. 15, 5027-5029.]); Yayli et al. (2006[Yayli, N., Ucuncu, O., Yasar, A., Kucuk, M., Yayli, N., Akyuz, E. & Alpay-Karaoglu, S. (2006). Turk. J. Chem. 30, 505-514.]). For related structures, see: Ng, Razak et al. (2006[Ng, S.-L., Razak, I. A., Fun, H.-K., Shettigar, V., Patil, P. S. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o2175-o2177.]); Ng, Patil et al. (2006[Ng, S.-L., Patil, P. S., Razak, I. A., Fun, H.-K. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o1228-o1230.]). For details of hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C25H32O3

  • Mr = 380.51

  • Monoclinic, P 21 /c

  • a = 12.4437 (2) Å

  • b = 35.5191 (6) Å

  • c = 9.8004 (2) Å

  • β = 99.284 (1)°

  • V = 4274.93 (13) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.52 × 0.44 × 0.35 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.962, Tmax = 0.974

  • 62626 measured reflections

  • 16928 independent reflections

  • 12634 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.153

  • S = 1.04

  • 16928 reflections

  • 515 parameters

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

  • Δρmax = 0.54 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1A—H1OA⋯O2Bi 0.91 (2) 1.80 (2) 2.711 (1) 179 (3)
O1B—H1OB⋯O2Aii 0.91 (2) 1.81 (2) 2.716 (1) 176 (2)
C4A—H4AA⋯O2Bi 0.93 2.50 3.185 (1) 131
C4B—H4BA⋯O2Aii 0.93 2.50 3.192 (1) 131
C14B—H14B⋯O3A 0.93 2.56 3.485 (1) 173
C18B—H18CCg1iii 0.97 2.85 3.696 (1) 146
C24B—H24DCg2iii 0.97 2.71 3.554 (1) 145
C22A—H22BCg3iv 0.97 2.95 3.743 (1) 140
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, -y, -z+2; (iv) [x, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]. Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C10B–C15B and C1B–C6B rings, respectively.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Chalcone derivatives are reported to possess biological properties such as anticancer (Bhat et al., 2005), antimalarial (Xue et al., 2004), antioxidant and antimicrobial activities (Yayli et al., 2006), antiplatelet activity (Zhao et al., 2005) as well as antihyperglycemic activity (Satyanarayana et al., 2004). Chalcone derivatives possessing alkyl chains have been synthesized in our lab and their antibacterial activities were tested against E. coli ATCC 8739. All the synthesized chalcone derivatives showed antimicrobial activity. The structure reported in this paper, (I), is one of the chalcone derivatives mentioned above.

There are two crystallographically independent molecules (A and B) in the asymmetric unit (Fig. 1). The bond lengths observed in (I) show normal values as reported by Allen et al., 1987. These two molecules (A and B) are interconnected by C14B—H14B···O3A intermolecular interactions (Table 1). In molecule A, the mean plane through the enone moiety (O2C7C8C9) and the two benzene rings make dihedral angles of 0.59 (7)° (C1—C6) and 4.49 (6)° (C10—C15) whereas in B, these angles are 4.21 (7)° (C1—C6) and 8.66 (7)° (C10—C15). The dihedral angles between the two benzene rings are 5.08 (5)° for molecule A and 9.23 (5)° for B. The alkoxyl tail in both molecules is coplanar with the attached ring with the torsion angle (C16—O3—C13—C12) in molecule B [5.06 (15)°] larger than in A [1.79 (15)°].

The enone moieties of both molecules adopt s-cis configuration with C7—C8—C9—O2 torsion angle being -1.2 (2)° for molecule A and -7.3 (2)° for B. The widening of C1A—C6A—C7A (123.94 (9)°) and C6A—C7A—C8A (128.28 (9)°) angles in molecule A is the result of the short H1AA···H8AA(2.32 Å) contact whereas short H8AA···H15A (2.17 Å) contact widened the C9A—C10A—C15A (124.53 (9)°). Similarly in molecule B, close interatomic contact between H1BA and H8BA (2.35 Å) results in the widening of C1B—C6B—C7B (124.33 (9)°) and C6B—C7B—C8B (129.01 (10)°) angles whereas the opening of C9B—C10B—C15B angle to 124.13 (9)° is the result of the close H8BA···H15B (2.18 Å) contact. Similar feature was also discussed in structures reported by Ng, Razak et al. (2006) and Ng, Patil et al. (2006).

In the crystal structure, O1A—H1OA···O2Bi and C4A—H4AA···O2Bi interactions in molecule A and O1B—H1OB···O2Aii and C4B—H4BA···O2Aii in B (Table 1) form bifurcated acceptor bonds which generate R12(6) ring motifs (Fig. 2). These intermolecular interactions translate the molecules into one-dimensional extended chains along the [1 0 -1] direction. The crystal structure is further stabilized by C—H···π interactions (Table 1).

Related literature top

For general background to the biological properties of chalcone derivatives, see: Bhat et al. (2005); Xue et al. (2004); Satyanarayana et al. (2004); Zhao et al. (2005); Yayli et al. (2006). For related structures, see: Ng, Razak et al. (2006); Ng, Patil et al. (2006). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). Cg1, Cg2 and Cg3 are the centroids of the C1A–C6A, C10B–C15B and C1B–C6B rings,

respectively.

Experimental top

A mixture of 4-hydroxybenzaldehyde (2.44 g, 20 mmol) and 4-decyloxyacethophenone (5.53 ml, 20 mmol) and KOH (4.04 g, 72 mmol) in 60 ml of methanol was heated at reflux for 24 h. The reaction was cooled to room temperature and was acidified with cold diluted HCl (2 N). The resulting precipitate was filtered, washed and dried. The precipitate was dissolved in hexane–ethanol (7:1) mixture. After a few days of slow evaporation, crystals suitable for X-ray analysis were collected.

Refinement top

All the carbon-bound H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å. The Uiso values were constrained to be Uiso(H) =1.5Uequ (methyl H atoms) and Uiso(H) =1.2Uequ (other H atoms). The rotating model group was considered for the methyl group. In the case of O1A and O1B, the hydrogen atoms were located from a difference Fourier map and refined isotropically.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
[Figure 2] Fig. 2. Part of the crystal packing of (I) showing R12(6) ring motifs generated by intermolecular interactions. The symmetry codes are given in Table 2.
(E)-1-(4-Decyloxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one top
Crystal data top
C25H32O3F(000) = 1648
Mr = 380.51Dx = 1.182 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9788 reflections
a = 12.4437 (2) Åθ = 2.4–33.6°
b = 35.5191 (6) ŵ = 0.08 mm1
c = 9.8004 (2) ÅT = 100 K
β = 99.284 (1)°Block, colourless
V = 4274.93 (13) Å30.52 × 0.44 × 0.35 mm
Z = 8
Data collection top
Bruker APEXII CCD area-detector
diffractometer
16928 independent reflections
Radiation source: sealed tube12634 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ϕ and ω scansθmax = 33.6°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1912
Tmin = 0.962, Tmax = 0.974k = 4755
62626 measured reflectionsl = 1515
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0694P)2 + 1.5875P]
where P = (Fo2 + 2Fc2)/3
16928 reflections(Δ/σ)max = 0.001
515 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C25H32O3V = 4274.93 (13) Å3
Mr = 380.51Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.4437 (2) ŵ = 0.08 mm1
b = 35.5191 (6) ÅT = 100 K
c = 9.8004 (2) Å0.52 × 0.44 × 0.35 mm
β = 99.284 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
16928 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
12634 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.974Rint = 0.027
62626 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.54 e Å3
16928 reflectionsΔρmin = 0.25 e Å3
515 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
O1A0.19648 (7)0.12225 (2)0.96568 (9)0.02036 (16)
O2A0.68305 (7)0.08504 (2)0.48100 (9)0.02114 (16)
O3A0.86470 (6)0.07913 (2)0.43003 (8)0.01776 (15)
C1A0.39100 (9)0.06947 (3)0.80269 (10)0.01565 (18)
H1AA0.41430.04470.79890.019*
C2A0.31110 (9)0.07833 (3)0.88043 (11)0.01666 (18)
H2AA0.28100.05950.92820.020*
C3A0.27532 (8)0.11552 (3)0.88759 (10)0.01508 (17)
C4A0.32006 (9)0.14375 (3)0.81526 (11)0.01803 (19)
H4AA0.29660.16850.81920.022*
C5A0.39998 (9)0.13443 (3)0.73730 (11)0.01765 (19)
H5AA0.42950.15330.68900.021*
C6A0.43747 (8)0.09747 (3)0.72928 (10)0.01372 (17)
C7A0.52133 (8)0.09029 (3)0.64537 (10)0.01487 (17)
H7AA0.54510.11110.60110.018*
C8A0.56916 (8)0.05727 (3)0.62344 (10)0.01469 (17)
H8AA0.54880.03530.66440.018*
C9A0.65358 (8)0.05601 (3)0.53460 (10)0.01421 (17)
C10A0.70600 (8)0.01986 (3)0.50805 (10)0.01370 (17)
C11A0.79143 (9)0.02091 (3)0.43098 (11)0.01715 (19)
H11A0.81160.04390.39770.021*
C12A0.84675 (9)0.01122 (3)0.40270 (11)0.01749 (19)
H12A0.90380.00970.35220.021*
C13A0.81582 (8)0.04600 (3)0.45113 (10)0.01456 (17)
C14A0.72985 (8)0.04794 (3)0.52714 (11)0.01556 (18)
H14A0.70890.07110.55880.019*
C15A0.67605 (8)0.01542 (3)0.55516 (10)0.01479 (17)
H15A0.61920.01690.60590.018*
C16A0.95178 (9)0.07828 (3)0.34939 (11)0.01798 (19)
H16A0.92540.06810.25830.022*
H16B1.01020.06230.39400.022*
C17A0.99332 (9)0.11775 (3)0.33678 (11)0.01747 (19)
H17A1.01900.12790.42810.021*
H17B0.93470.13370.29210.021*
C18A1.08613 (9)0.11765 (3)0.25216 (12)0.0205 (2)
H18A1.14560.10270.30040.025*
H18B1.06100.10560.16400.025*
C19A1.12904 (9)0.15667 (3)0.22545 (11)0.01802 (19)
H19A1.15300.16910.31320.022*
H19B1.07050.17150.17440.022*
C20A1.22377 (9)0.15512 (3)0.14381 (12)0.0193 (2)
H20A1.28360.14150.19750.023*
H20B1.20090.14120.05880.023*
C21A1.26404 (9)0.19380 (3)0.10818 (11)0.01678 (18)
H21A1.28870.20740.19320.020*
H21B1.20370.20770.05650.020*
C22A1.35682 (9)0.19220 (3)0.02342 (11)0.01782 (19)
H22A1.41770.17880.07590.021*
H22B1.33270.17810.06070.021*
C23A1.39557 (9)0.23103 (3)0.01474 (11)0.01709 (18)
H23A1.33470.24430.06800.021*
H23B1.41850.24520.06950.021*
C24A1.48909 (10)0.23004 (3)0.09762 (13)0.0224 (2)
H24A1.46640.21620.18270.027*
H24B1.55030.21680.04490.027*
C25A1.52534 (10)0.26954 (3)0.13242 (13)0.0231 (2)
H25A1.58450.26770.18400.035*
H25B1.54880.28320.04840.035*
H25C1.46550.28250.18670.035*
O1B1.31221 (7)0.33893 (2)0.04708 (9)0.02207 (17)
O2B0.84313 (8)0.30275 (2)0.55634 (10)0.0293 (2)
O3B0.68508 (7)0.13810 (2)0.65982 (8)0.01930 (16)
C1B1.12915 (9)0.28531 (3)0.22651 (12)0.0189 (2)
H1BA1.11380.26020.24170.023*
C2B1.20746 (10)0.29428 (3)0.14624 (12)0.0208 (2)
H2BA1.24360.27520.10710.025*
C3B1.23247 (9)0.33191 (3)0.12373 (11)0.01589 (18)
C4B1.17622 (9)0.36043 (3)0.17965 (11)0.01771 (19)
H4BA1.19140.38560.16400.021*
C5B1.09736 (9)0.35102 (3)0.25890 (11)0.01814 (19)
H5BA1.05980.37020.29560.022*
C6B1.07262 (8)0.31357 (3)0.28527 (11)0.01511 (18)
C7B0.99147 (9)0.30651 (3)0.37343 (11)0.01700 (19)
H7BA0.95660.32780.40050.020*
C8B0.95974 (9)0.27355 (3)0.42135 (11)0.01687 (18)
H8BA0.99040.25110.39710.020*
C9B0.87663 (9)0.27302 (3)0.51200 (11)0.01733 (19)
C10B0.83094 (8)0.23694 (3)0.55219 (11)0.01535 (18)
C11B0.75851 (9)0.23806 (3)0.64765 (11)0.01700 (19)
H11B0.74330.26110.68540.020*
C12B0.70886 (9)0.20588 (3)0.68738 (11)0.01700 (19)
H12B0.66100.20730.75090.020*
C13B0.73143 (8)0.17123 (3)0.63101 (10)0.01518 (17)
C14B0.80510 (9)0.16922 (3)0.53728 (12)0.0188 (2)
H14B0.82120.14610.50110.023*
C15B0.85396 (9)0.20172 (3)0.49851 (11)0.01832 (19)
H15B0.90270.20020.43610.022*
C16B0.60126 (9)0.13979 (3)0.74562 (11)0.01719 (19)
H16C0.54190.15560.70260.021*
H16D0.63050.15040.83510.021*
C17B0.56056 (9)0.10029 (3)0.76309 (11)0.01687 (18)
H17C0.62000.08480.80810.020*
H17D0.53420.08950.67300.020*
C18B0.46876 (9)0.10052 (3)0.84962 (11)0.01672 (18)
H18C0.49520.11200.93840.020*
H18D0.40940.11590.80330.020*
C19B0.42533 (9)0.06142 (3)0.87367 (11)0.01718 (19)
H19C0.48470.04590.91890.021*
H19D0.39770.05000.78500.021*
C20B0.33482 (9)0.06196 (3)0.96191 (11)0.01738 (19)
H20C0.36170.07421.04920.021*
H20D0.27450.07680.91510.021*
C21B0.29339 (9)0.02284 (3)0.99067 (11)0.01762 (19)
H21C0.35400.00801.03640.021*
H21D0.26600.01080.90320.021*
C22B0.20355 (8)0.02275 (3)1.08003 (11)0.01643 (18)
H22C0.23130.03421.16860.020*
H22D0.14340.03811.03560.020*
C23B0.16144 (8)0.01652 (3)1.10443 (11)0.01573 (18)
H23C0.22160.03171.14980.019*
H23D0.13490.02801.01560.019*
C24B0.07056 (9)0.01719 (3)1.19178 (11)0.01754 (19)
H24C0.01010.00201.14710.021*
H24D0.09690.00611.28140.021*
C25B0.03045 (10)0.05710 (3)1.21225 (13)0.0231 (2)
H25D0.02760.05621.26590.035*
H25E0.08930.07191.25990.035*
H25F0.00440.06821.12380.035*
H1OB1.3164 (14)0.3643 (6)0.0362 (19)0.044 (5)*
H1OA0.1825 (15)0.1475 (6)0.9592 (19)0.046 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0220 (4)0.0178 (4)0.0250 (4)0.0022 (3)0.0151 (3)0.0001 (3)
O2A0.0248 (4)0.0131 (3)0.0295 (4)0.0007 (3)0.0166 (3)0.0028 (3)
O3A0.0201 (4)0.0131 (3)0.0229 (4)0.0027 (3)0.0118 (3)0.0005 (3)
C1A0.0186 (5)0.0123 (4)0.0176 (4)0.0009 (3)0.0077 (3)0.0004 (3)
C2A0.0197 (5)0.0134 (4)0.0190 (4)0.0003 (3)0.0092 (4)0.0017 (3)
C3A0.0146 (4)0.0154 (4)0.0167 (4)0.0003 (3)0.0069 (3)0.0011 (3)
C4A0.0206 (5)0.0126 (4)0.0236 (5)0.0017 (4)0.0117 (4)0.0001 (3)
C5A0.0205 (5)0.0129 (4)0.0220 (5)0.0003 (3)0.0110 (4)0.0012 (3)
C6A0.0145 (4)0.0126 (4)0.0153 (4)0.0003 (3)0.0060 (3)0.0004 (3)
C7A0.0152 (4)0.0143 (4)0.0164 (4)0.0003 (3)0.0065 (3)0.0003 (3)
C8A0.0154 (4)0.0138 (4)0.0163 (4)0.0005 (3)0.0068 (3)0.0009 (3)
C9A0.0143 (4)0.0133 (4)0.0161 (4)0.0003 (3)0.0055 (3)0.0004 (3)
C10A0.0147 (4)0.0124 (4)0.0152 (4)0.0002 (3)0.0059 (3)0.0001 (3)
C11A0.0191 (5)0.0135 (4)0.0212 (5)0.0007 (3)0.0102 (4)0.0018 (3)
C12A0.0187 (5)0.0148 (4)0.0217 (5)0.0015 (4)0.0116 (4)0.0006 (3)
C13A0.0154 (4)0.0133 (4)0.0159 (4)0.0012 (3)0.0055 (3)0.0012 (3)
C14A0.0166 (5)0.0132 (4)0.0183 (4)0.0004 (3)0.0068 (3)0.0004 (3)
C15A0.0144 (4)0.0148 (4)0.0168 (4)0.0001 (3)0.0073 (3)0.0005 (3)
C16A0.0175 (5)0.0161 (5)0.0226 (5)0.0013 (4)0.0103 (4)0.0016 (4)
C17A0.0176 (5)0.0155 (4)0.0208 (5)0.0024 (3)0.0075 (4)0.0011 (3)
C18A0.0191 (5)0.0165 (5)0.0284 (5)0.0011 (4)0.0117 (4)0.0028 (4)
C19A0.0189 (5)0.0161 (5)0.0207 (5)0.0016 (4)0.0082 (4)0.0020 (3)
C20A0.0199 (5)0.0159 (5)0.0242 (5)0.0016 (4)0.0098 (4)0.0026 (4)
C21A0.0163 (5)0.0162 (4)0.0192 (4)0.0021 (3)0.0070 (4)0.0004 (3)
C22A0.0181 (5)0.0165 (5)0.0208 (5)0.0016 (4)0.0087 (4)0.0004 (3)
C23A0.0176 (5)0.0163 (4)0.0192 (4)0.0012 (3)0.0087 (4)0.0000 (3)
C24A0.0220 (5)0.0189 (5)0.0300 (6)0.0005 (4)0.0152 (4)0.0025 (4)
C25A0.0214 (5)0.0216 (5)0.0282 (5)0.0036 (4)0.0100 (4)0.0036 (4)
O1B0.0255 (4)0.0154 (4)0.0301 (4)0.0002 (3)0.0187 (3)0.0018 (3)
O2B0.0372 (5)0.0137 (4)0.0445 (5)0.0007 (3)0.0292 (4)0.0017 (3)
O3B0.0230 (4)0.0129 (3)0.0256 (4)0.0035 (3)0.0146 (3)0.0003 (3)
C1B0.0219 (5)0.0120 (4)0.0257 (5)0.0013 (4)0.0129 (4)0.0010 (4)
C2B0.0260 (6)0.0131 (4)0.0271 (5)0.0005 (4)0.0161 (4)0.0015 (4)
C3B0.0169 (5)0.0143 (4)0.0185 (4)0.0004 (3)0.0089 (3)0.0005 (3)
C4B0.0208 (5)0.0118 (4)0.0230 (5)0.0006 (3)0.0109 (4)0.0015 (3)
C5B0.0205 (5)0.0123 (4)0.0243 (5)0.0012 (3)0.0116 (4)0.0011 (3)
C6B0.0143 (4)0.0137 (4)0.0187 (4)0.0002 (3)0.0070 (3)0.0008 (3)
C7B0.0168 (5)0.0149 (4)0.0211 (5)0.0001 (3)0.0087 (4)0.0001 (3)
C8B0.0163 (5)0.0143 (4)0.0220 (5)0.0012 (3)0.0090 (4)0.0010 (3)
C9B0.0176 (5)0.0147 (4)0.0219 (5)0.0008 (3)0.0099 (4)0.0003 (3)
C10B0.0149 (4)0.0137 (4)0.0191 (4)0.0014 (3)0.0076 (3)0.0001 (3)
C11B0.0184 (5)0.0137 (4)0.0213 (5)0.0017 (3)0.0103 (4)0.0019 (3)
C12B0.0183 (5)0.0154 (4)0.0199 (4)0.0022 (3)0.0108 (4)0.0008 (3)
C13B0.0158 (4)0.0131 (4)0.0180 (4)0.0017 (3)0.0066 (3)0.0008 (3)
C14B0.0214 (5)0.0132 (4)0.0248 (5)0.0012 (4)0.0122 (4)0.0022 (4)
C15B0.0199 (5)0.0148 (4)0.0233 (5)0.0014 (4)0.0126 (4)0.0009 (4)
C16B0.0186 (5)0.0155 (4)0.0198 (4)0.0022 (4)0.0101 (4)0.0006 (3)
C17B0.0191 (5)0.0141 (4)0.0193 (4)0.0024 (3)0.0087 (4)0.0013 (3)
C18B0.0179 (5)0.0144 (4)0.0190 (4)0.0015 (3)0.0065 (4)0.0015 (3)
C19B0.0195 (5)0.0152 (4)0.0183 (4)0.0030 (4)0.0075 (4)0.0003 (3)
C20B0.0191 (5)0.0147 (4)0.0199 (4)0.0017 (4)0.0080 (4)0.0011 (3)
C21B0.0200 (5)0.0148 (4)0.0199 (4)0.0023 (4)0.0086 (4)0.0008 (3)
C22B0.0164 (5)0.0157 (4)0.0185 (4)0.0017 (3)0.0067 (3)0.0008 (3)
C23B0.0166 (4)0.0143 (4)0.0178 (4)0.0006 (3)0.0070 (3)0.0004 (3)
C24B0.0174 (5)0.0171 (5)0.0199 (5)0.0013 (4)0.0083 (4)0.0011 (3)
C25B0.0227 (5)0.0211 (5)0.0273 (5)0.0056 (4)0.0094 (4)0.0019 (4)
Geometric parameters (Å, º) top
O1A—C3A1.3592 (12)O1B—C3B1.3607 (12)
O1A—H1OA0.92 (2)O1B—H1OB0.91 (2)
O2A—C9A1.2396 (12)O2B—C9B1.2396 (13)
O3A—C13A1.3559 (12)O3B—C13B1.3600 (12)
O3A—C16A1.4407 (12)O3B—C16B1.4427 (12)
C1A—C2A1.3829 (14)C1B—C2B1.3848 (14)
C1A—C6A1.4054 (14)C1B—C6B1.4016 (14)
C1A—H1AA0.9300C1B—H1BA0.9300
C2A—C3A1.3995 (14)C2B—C3B1.3980 (14)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.3946 (14)C3B—C4B1.3928 (14)
C4A—C5A1.3884 (14)C4B—C5B1.3871 (14)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.3998 (14)C5B—C6B1.3989 (14)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.4516 (13)C6B—C7B1.4527 (14)
C7A—C8A1.3480 (14)C7B—C8B1.3445 (14)
C7A—H7AA0.9300C7B—H7BA0.9300
C8A—C9A1.4693 (13)C8B—C9B1.4681 (14)
C8A—H8AA0.9300C8B—H8BA0.9300
C9A—C10A1.4821 (14)C9B—C10B1.4810 (14)
C10A—C11A1.4004 (13)C10B—C11B1.4005 (14)
C10A—C15A1.4062 (14)C10B—C15B1.4044 (14)
C11A—C12A1.3837 (14)C11B—C12B1.3848 (14)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.3994 (14)C12B—C13B1.3958 (14)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.4005 (14)C13B—C14B1.4004 (14)
C14A—C15A1.3846 (14)C14B—C15B1.3860 (15)
C14A—H14A0.9300C14B—H14B0.9300
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.5060 (14)C16B—C17B1.5106 (14)
C16A—H16A0.9700C16B—H16C0.9700
C16A—H16B0.9700C16B—H16D0.9700
C17A—C18A1.5266 (15)C17B—C18B1.5286 (14)
C17A—H17A0.9700C17B—H17C0.9700
C17A—H17B0.9700C17B—H17D0.9700
C18A—C19A1.5231 (15)C18B—C19B1.5224 (14)
C18A—H18A0.9700C18B—H18C0.9700
C18A—H18B0.9700C18B—H18D0.9700
C19A—C20A1.5287 (15)C19B—C20B1.5267 (14)
C19A—H19A0.9700C19B—H19C0.9700
C19A—H19B0.9700C19B—H19D0.9700
C20A—C21A1.5223 (14)C20B—C21B1.5239 (14)
C20A—H20A0.9700C20B—H20C0.9700
C20A—H20B0.9700C20B—H20D0.9700
C21A—C22A1.5282 (14)C21B—C22B1.5272 (14)
C21A—H21A0.9700C21B—H21C0.9700
C21A—H21B0.9700C21B—H21D0.9700
C22A—C23A1.5272 (15)C22B—C23B1.5223 (14)
C22A—H22A0.9700C22B—H22C0.9700
C22A—H22B0.9700C22B—H22D0.9700
C23A—C24A1.5232 (14)C23B—C24B1.5247 (14)
C23A—H23A0.9700C23B—H23C0.9700
C23A—H23B0.9700C23B—H23D0.9700
C24A—C25A1.5291 (16)C24B—C25B1.5269 (15)
C24A—H24A0.9700C24B—H24C0.9700
C24A—H24B0.9700C24B—H24D0.9700
C25A—H25A0.9600C25B—H25D0.9600
C25A—H25B0.9600C25B—H25E0.9600
C25A—H25C0.9600C25B—H25F0.9600
C3A—O1A—H1OA106.3 (11)C3B—O1B—H1OB107.9 (11)
C13A—O3A—C16A117.46 (8)C13B—O3B—C16B117.12 (8)
C2A—C1A—C6A120.85 (9)C2B—C1B—C6B120.96 (10)
C2A—C1A—H1AA119.6C2B—C1B—H1BA119.5
C6A—C1A—H1AA119.6C6B—C1B—H1BA119.5
C1A—C2A—C3A120.35 (9)C1B—C2B—C3B120.31 (10)
C1A—C2A—H2AA119.8C1B—C2B—H2BA119.8
C3A—C2A—H2AA119.8C3B—C2B—H2BA119.8
O1A—C3A—C4A122.92 (9)O1B—C3B—C4B122.79 (9)
O1A—C3A—C2A117.29 (9)O1B—C3B—C2B117.58 (9)
C4A—C3A—C2A119.79 (9)C4B—C3B—C2B119.64 (9)
C5A—C4A—C3A119.24 (9)C5B—C4B—C3B119.39 (9)
C5A—C4A—H4AA120.4C5B—C4B—H4BA120.3
C3A—C4A—H4AA120.4C3B—C4B—H4BA120.3
C4A—C5A—C6A121.95 (9)C4B—C5B—C6B121.96 (9)
C4A—C5A—H5AA119.0C4B—C5B—H5BA119.0
C6A—C5A—H5AA119.0C6B—C5B—H5BA119.0
C5A—C6A—C1A117.82 (9)C5B—C6B—C1B117.72 (9)
C5A—C6A—C7A118.24 (9)C5B—C6B—C7B117.95 (9)
C1A—C6A—C7A123.94 (9)C1B—C6B—C7B124.33 (9)
C8A—C7A—C6A128.28 (9)C8B—C7B—C6B129.01 (10)
C8A—C7A—H7AA115.9C8B—C7B—H7BA115.5
C6A—C7A—H7AA115.9C6B—C7B—H7BA115.5
C7A—C8A—C9A119.82 (9)C7B—C8B—C9B119.85 (9)
C7A—C8A—H8AA120.1C7B—C8B—H8BA120.1
C9A—C8A—H8AA120.1C9B—C8B—H8BA120.1
O2A—C9A—C8A120.96 (9)O2B—C9B—C8B120.72 (9)
O2A—C9A—C10A118.54 (9)O2B—C9B—C10B118.61 (9)
C8A—C9A—C10A120.49 (8)C8B—C9B—C10B120.67 (9)
C11A—C10A—C15A117.73 (9)C11B—C10B—C15B117.89 (9)
C11A—C10A—C9A117.74 (9)C11B—C10B—C9B117.97 (9)
C15A—C10A—C9A124.53 (9)C15B—C10B—C9B124.13 (9)
C12A—C11A—C10A122.10 (9)C12B—C11B—C10B121.92 (9)
C12A—C11A—H11A118.9C12B—C11B—H11B119.0
C10A—C11A—H11A118.9C10B—C11B—H11B119.0
C11A—C12A—C13A119.16 (9)C11B—C12B—C13B119.28 (9)
C11A—C12A—H12A120.4C11B—C12B—H12B120.4
C13A—C12A—H12A120.4C13B—C12B—H12B120.4
O3A—C13A—C12A124.04 (9)O3B—C13B—C12B124.16 (9)
O3A—C13A—C14A116.00 (9)O3B—C13B—C14B115.87 (9)
C12A—C13A—C14A119.96 (9)C12B—C13B—C14B119.97 (9)
C15A—C14A—C13A119.97 (9)C15B—C14B—C13B119.99 (9)
C15A—C14A—H14A120.0C15B—C14B—H14B120.0
C13A—C14A—H14A120.0C13B—C14B—H14B120.0
C14A—C15A—C10A121.07 (9)C14B—C15B—C10B120.94 (9)
C14A—C15A—H15A119.5C14B—C15B—H15B119.5
C10A—C15A—H15A119.5C10B—C15B—H15B119.5
O3A—C16A—C17A108.91 (8)O3B—C16B—C17B108.34 (8)
O3A—C16A—H16A109.9O3B—C16B—H16C110.0
C17A—C16A—H16A109.9C17B—C16B—H16C110.0
O3A—C16A—H16B109.9O3B—C16B—H16D110.0
C17A—C16A—H16B109.9C17B—C16B—H16D110.0
H16A—C16A—H16B108.3H16C—C16B—H16D108.4
C16A—C17A—C18A110.01 (9)C16B—C17B—C18B110.62 (8)
C16A—C17A—H17A109.7C16B—C17B—H17C109.5
C18A—C17A—H17A109.7C18B—C17B—H17C109.5
C16A—C17A—H17B109.7C16B—C17B—H17D109.5
C18A—C17A—H17B109.7C18B—C17B—H17D109.5
H17A—C17A—H17B108.2H17C—C17B—H17D108.1
C19A—C18A—C17A114.09 (9)C19B—C18B—C17B113.38 (9)
C19A—C18A—H18A108.7C19B—C18B—H18C108.9
C17A—C18A—H18A108.7C17B—C18B—H18C108.9
C19A—C18A—H18B108.7C19B—C18B—H18D108.9
C17A—C18A—H18B108.7C17B—C18B—H18D108.9
H18A—C18A—H18B107.6H18C—C18B—H18D107.7
C18A—C19A—C20A112.24 (9)C18B—C19B—C20B112.89 (9)
C18A—C19A—H19A109.2C18B—C19B—H19C109.0
C20A—C19A—H19A109.2C20B—C19B—H19C109.0
C18A—C19A—H19B109.2C18B—C19B—H19D109.0
C20A—C19A—H19B109.2C20B—C19B—H19D109.0
H19A—C19A—H19B107.9H19C—C19B—H19D107.8
C21A—C20A—C19A113.43 (9)C21B—C20B—C19B113.32 (9)
C21A—C20A—H20A108.9C21B—C20B—H20C108.9
C19A—C20A—H20A108.9C19B—C20B—H20C108.9
C21A—C20A—H20B108.9C21B—C20B—H20D108.9
C19A—C20A—H20B108.9C19B—C20B—H20D108.9
H20A—C20A—H20B107.7H20C—C20B—H20D107.7
C20A—C21A—C22A113.37 (9)C20B—C21B—C22B114.14 (9)
C20A—C21A—H21A108.9C20B—C21B—H21C108.7
C22A—C21A—H21A108.9C22B—C21B—H21C108.7
C20A—C21A—H21B108.9C20B—C21B—H21D108.7
C22A—C21A—H21B108.9C22B—C21B—H21D108.7
H21A—C21A—H21B107.7H21C—C21B—H21D107.6
C23A—C22A—C21A113.31 (9)C23B—C22B—C21B113.23 (8)
C23A—C22A—H22A108.9C23B—C22B—H22C108.9
C21A—C22A—H22A108.9C21B—C22B—H22C108.9
C23A—C22A—H22B108.9C23B—C22B—H22D108.9
C21A—C22A—H22B108.9C21B—C22B—H22D108.9
H22A—C22A—H22B107.7H22C—C22B—H22D107.7
C24A—C23A—C22A114.10 (9)C22B—C23B—C24B114.07 (8)
C24A—C23A—H23A108.7C22B—C23B—H23C108.7
C22A—C23A—H23A108.7C24B—C23B—H23C108.7
C24A—C23A—H23B108.7C22B—C23B—H23D108.7
C22A—C23A—H23B108.7C24B—C23B—H23D108.7
H23A—C23A—H23B107.6H23C—C23B—H23D107.6
C23A—C24A—C25A112.09 (9)C23B—C24B—C25B112.09 (9)
C23A—C24A—H24A109.2C23B—C24B—H24C109.2
C25A—C24A—H24A109.2C25B—C24B—H24C109.2
C23A—C24A—H24B109.2C23B—C24B—H24D109.2
C25A—C24A—H24B109.2C25B—C24B—H24D109.2
H24A—C24A—H24B107.9H24C—C24B—H24D107.9
C24A—C25A—H25A109.5C24B—C25B—H25D109.5
C24A—C25A—H25B109.5C24B—C25B—H25E109.5
H25A—C25A—H25B109.5H25D—C25B—H25E109.5
C24A—C25A—H25C109.5C24B—C25B—H25F109.5
H25A—C25A—H25C109.5H25D—C25B—H25F109.5
H25B—C25A—H25C109.5H25E—C25B—H25F109.5
C6A—C1A—C2A—C3A0.19 (16)C6B—C1B—C2B—C3B0.77 (18)
C1A—C2A—C3A—O1A179.91 (10)C1B—C2B—C3B—O1B178.25 (11)
C1A—C2A—C3A—C4A0.38 (16)C1B—C2B—C3B—C4B1.61 (17)
O1A—C3A—C4A—C5A179.69 (10)O1B—C3B—C4B—C5B178.78 (10)
C2A—C3A—C4A—C5A0.18 (16)C2B—C3B—C4B—C5B1.07 (17)
C3A—C4A—C5A—C6A0.20 (17)C3B—C4B—C5B—C6B0.31 (17)
C4A—C5A—C6A—C1A0.38 (16)C4B—C5B—C6B—C1B1.13 (17)
C4A—C5A—C6A—C7A179.95 (10)C4B—C5B—C6B—C7B177.88 (10)
C2A—C1A—C6A—C5A0.18 (15)C2B—C1B—C6B—C5B0.58 (17)
C2A—C1A—C6A—C7A179.83 (10)C2B—C1B—C6B—C7B178.35 (11)
C5A—C6A—C7A—C8A179.76 (11)C5B—C6B—C7B—C8B174.80 (11)
C1A—C6A—C7A—C8A0.58 (17)C1B—C6B—C7B—C8B4.13 (19)
C6A—C7A—C8A—C9A179.70 (10)C6B—C7B—C8B—C9B178.96 (10)
C7A—C8A—C9A—O2A1.22 (16)C7B—C8B—C9B—O2B7.31 (17)
C7A—C8A—C9A—C10A179.25 (9)C7B—C8B—C9B—C10B172.58 (10)
O2A—C9A—C10A—C11A4.18 (15)O2B—C9B—C10B—C11B5.15 (16)
C8A—C9A—C10A—C11A175.37 (9)C8B—C9B—C10B—C11B174.95 (10)
O2A—C9A—C10A—C15A175.97 (10)O2B—C9B—C10B—C15B173.51 (11)
C8A—C9A—C10A—C15A4.49 (15)C8B—C9B—C10B—C15B6.39 (17)
C15A—C10A—C11A—C12A0.99 (16)C15B—C10B—C11B—C12B1.09 (16)
C9A—C10A—C11A—C12A178.88 (10)C9B—C10B—C11B—C12B177.65 (10)
C10A—C11A—C12A—C13A0.74 (17)C10B—C11B—C12B—C13B0.02 (17)
C16A—O3A—C13A—C12A1.79 (15)C16B—O3B—C13B—C12B5.06 (15)
C16A—O3A—C13A—C14A178.55 (9)C16B—O3B—C13B—C14B174.26 (9)
C11A—C12A—C13A—O3A179.64 (10)C11B—C12B—C13B—O3B178.14 (10)
C11A—C12A—C13A—C14A0.00 (16)C11B—C12B—C13B—C14B1.16 (16)
O3A—C13A—C14A—C15A179.21 (9)O3B—C13B—C14B—C15B178.11 (10)
C12A—C13A—C14A—C15A0.47 (16)C12B—C13B—C14B—C15B1.24 (17)
C13A—C14A—C15A—C10A0.21 (16)C13B—C14B—C15B—C10B0.14 (17)
C11A—C10A—C15A—C14A0.50 (15)C11B—C10B—C15B—C14B1.00 (16)
C9A—C10A—C15A—C14A179.35 (10)C9B—C10B—C15B—C14B177.66 (11)
C13A—O3A—C16A—C17A179.19 (9)C13B—O3B—C16B—C17B179.40 (9)
O3A—C16A—C17A—C18A179.77 (9)O3B—C16B—C17B—C18B178.19 (8)
C16A—C17A—C18A—C19A176.24 (10)C16B—C17B—C18B—C19B178.88 (9)
C17A—C18A—C19A—C20A178.47 (9)C17B—C18B—C19B—C20B179.18 (9)
C18A—C19A—C20A—C21A176.60 (9)C18B—C19B—C20B—C21B178.06 (9)
C19A—C20A—C21A—C22A178.54 (9)C19B—C20B—C21B—C22B179.42 (9)
C20A—C21A—C22A—C23A178.83 (9)C20B—C21B—C22B—C23B178.56 (9)
C21A—C22A—C23A—C24A179.22 (9)C21B—C22B—C23B—C24B179.19 (9)
C22A—C23A—C24A—C25A179.64 (10)C22B—C23B—C24B—C25B179.50 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···O2Bi0.91 (2)1.80 (2)2.711 (1)179 (3)
O1B—H1OB···O2Aii0.91 (2)1.81 (2)2.716 (1)176 (2)
C4A—H4AA···O2Bi0.932.503.185 (1)131
C4B—H4BA···O2Aii0.932.503.192 (1)131
C14B—H14B···O3A0.932.563.485 (1)173
C18B—H18C···Cg1iii0.972.853.696 (1)146
C24B—H24D···Cg2iii0.972.713.554 (1)145
C22A—H22B···Cg3iv0.972.953.743 (1)140
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+2, y+1/2, z+1/2; (iii) x+1, y, z+2; (iv) x, y1/2, z3/2.

Experimental details

Crystal data
Chemical formulaC25H32O3
Mr380.51
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)12.4437 (2), 35.5191 (6), 9.8004 (2)
β (°) 99.284 (1)
V3)4274.93 (13)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.52 × 0.44 × 0.35
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.962, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
62626, 16928, 12634
Rint0.027
(sin θ/λ)max1)0.779
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.153, 1.04
No. of reflections16928
No. of parameters515
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.54, 0.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···O2Bi0.91 (2)1.80 (2)2.711 (1)179 (3)
O1B—H1OB···O2Aii0.91 (2)1.81 (2)2.716 (1)176 (2)
C4A—H4AA···O2Bi0.932.503.185 (1)131
C4B—H4BA···O2Aii0.932.503.192 (1)131
C14B—H14B···O3A0.932.563.485 (1)173
C18B—H18C···Cg1iii0.972.853.696 (1)146
C24B—H24D···Cg2iii0.972.713.554 (1)145
C22A—H22B···Cg3iv0.972.953.743 (1)140
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+2, y+1/2, z+1/2; (iii) x+1, y, z+2; (iv) x, y1/2, z3/2.
 

Footnotes

Additional correspondence author, email: hkfun@usm.my.

Acknowledgements

HKF and IAR thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312 and the Research University Golden Goose grant No.1001/PFIZIK/811012. ZN and HH thank Universiti Malaysia Sarawak for the Geran Penyelidikan Dana Khas Inovasi, grant No. DI/01/2007(01). SMHF thanks the Malaysian Government and Universiti Malaysia Sarawak for a providing scholarship for postgraduate studies.

References

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Volume 65| Part 4| April 2009| Pages o881-o882
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