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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o881–o882.
Published online 2009 March 28. doi:  10.1107/S160053680901054X
PMCID: PMC2969075

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

Abstract

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 R 1 2(6) ring motifs. These inter­molecular inter­actions link the mol­ecules into one-dimensional chains along the [10An external file that holds a picture, illustration, etc.
Object name is e-65-0o881-efi2.jpg] 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 [triangle]); Xue et al. (2004 [triangle]); Satyanarayana et al. (2004 [triangle]); Zhao et al. (2005 [triangle]); Yayli et al. (2006 [triangle]). For related structures, see: Ng, Razak et al. (2006 [triangle]); Ng, Patil et al. (2006 [triangle]). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o881-scheme1.jpg

Experimental

Crystal data

  • C25H32O3
  • M r = 380.51
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o881-efi3.jpg
  • 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 [triangle]) T min = 0.962, T max = 0.974
  • 62626 measured reflections
  • 16928 independent reflections
  • 12634 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901054X/at2746sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901054X/at2746Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
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.

Crystal data

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

Bruker APEXII CCD area-detector diffractometer16928 independent reflections
Radiation source: sealed tube12634 reflections with I > 2σ(I)
graphiteRint = 0.027
[var phi] and ω scansθmax = 33.6°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −19→12
Tmin = 0.962, Tmax = 0.974k = −47→55
62626 measured reflectionsl = −15→15

Refinement

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 = 1.04w = 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

Special details

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)

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)
H1AA0.4143−0.04470.79890.019*
C2A0.31110 (9)−0.07833 (3)0.88043 (11)0.01666 (18)
H2AA0.2810−0.05950.92820.020*
C3A0.27532 (8)−0.11552 (3)0.88759 (10)0.01508 (17)
C4A0.32006 (9)−0.14375 (3)0.81526 (11)0.01803 (19)
H4AA0.2966−0.16850.81920.022*
C5A0.39998 (9)−0.13443 (3)0.73730 (11)0.01765 (19)
H5AA0.4295−0.15330.68900.021*
C6A0.43747 (8)−0.09747 (3)0.72928 (10)0.01372 (17)
C7A0.52133 (8)−0.09029 (3)0.64537 (10)0.01487 (17)
H7AA0.5451−0.11110.60110.018*
C8A0.56916 (8)−0.05727 (3)0.62344 (10)0.01469 (17)
H8AA0.5488−0.03530.66440.018*
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)
H11A0.8116−0.04390.39770.021*
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*
H22B1.33270.1781−0.06070.021*
C23A1.39557 (9)0.23103 (3)−0.01474 (11)0.01709 (18)
H23A1.33470.2443−0.06800.021*
H23B1.41850.24520.06950.021*
C24A1.48909 (10)0.23004 (3)−0.09762 (13)0.0224 (2)
H24A1.46640.2162−0.18270.027*
H24B1.55030.2168−0.04490.027*
C25A1.52534 (10)0.26954 (3)−0.13242 (13)0.0231 (2)
H25A1.58450.2677−0.18400.035*
H25B1.54880.2832−0.04840.035*
H25C1.46550.2825−0.18670.035*
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)
H23C0.2216−0.03171.14980.019*
H23D0.1349−0.02801.01560.019*
C24B0.07056 (9)−0.01719 (3)1.19178 (11)0.01754 (19)
H24C0.0101−0.00201.14710.021*
H24D0.0969−0.00611.28140.021*
C25B0.03045 (10)−0.05710 (3)1.21225 (13)0.0231 (2)
H25D−0.0276−0.05621.26590.035*
H25E0.0893−0.07191.25990.035*
H25F0.0044−0.06821.12380.035*
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)

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, °)

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—O1A−179.91 (10)C1B—C2B—C3B—O1B178.25 (11)
C1A—C2A—C3A—C4A−0.38 (16)C1B—C2B—C3B—C4B−1.61 (17)
O1A—C3A—C4A—C5A179.69 (10)O1B—C3B—C4B—C5B−178.78 (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—C1A−0.38 (16)C4B—C5B—C6B—C1B−1.13 (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—C7B−178.35 (11)
C5A—C6A—C7A—C8A−179.76 (11)C5B—C6B—C7B—C8B−174.80 (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—O2A−1.22 (16)C7B—C8B—C9B—O2B−7.31 (17)
C7A—C8A—C9A—C10A179.25 (9)C7B—C8B—C9B—C10B172.58 (10)
O2A—C9A—C10A—C11A−4.18 (15)O2B—C9B—C10B—C11B−5.15 (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—C15A−4.49 (15)C8B—C9B—C10B—C15B−6.39 (17)
C15A—C10A—C11A—C12A0.99 (16)C15B—C10B—C11B—C12B−1.09 (16)
C9A—C10A—C11A—C12A−178.88 (10)C9B—C10B—C11B—C12B177.65 (10)
C10A—C11A—C12A—C13A−0.74 (17)C10B—C11B—C12B—C13B0.02 (17)
C16A—O3A—C13A—C12A1.79 (15)C16B—O3B—C13B—C12B5.06 (15)
C16A—O3A—C13A—C14A−178.55 (9)C16B—O3B—C13B—C14B−174.26 (9)
C11A—C12A—C13A—O3A179.64 (10)C11B—C12B—C13B—O3B−178.14 (10)
C11A—C12A—C13A—C14A0.00 (16)C11B—C12B—C13B—C14B1.16 (16)
O3A—C13A—C14A—C15A−179.21 (9)O3B—C13B—C14B—C15B178.11 (10)
C12A—C13A—C14A—C15A0.47 (16)C12B—C13B—C14B—C15B−1.24 (17)
C13A—C14A—C15A—C10A−0.21 (16)C13B—C14B—C15B—C10B0.14 (17)
C11A—C10A—C15A—C14A−0.50 (15)C11B—C10B—C15B—C14B1.00 (16)
C9A—C10A—C15A—C14A179.35 (10)C9B—C10B—C15B—C14B−177.66 (11)
C13A—O3A—C16A—C17A179.19 (9)C13B—O3B—C16B—C17B179.40 (9)
O3A—C16A—C17A—C18A179.77 (9)O3B—C16B—C17B—C18B−178.19 (8)
C16A—C17A—C18A—C19A176.24 (10)C16B—C17B—C18B—C19B−178.88 (9)
C17A—C18A—C19A—C20A178.47 (9)C17B—C18B—C19B—C20B179.18 (9)
C18A—C19A—C20A—C21A176.60 (9)C18B—C19B—C20B—C21B−178.06 (9)
C19A—C20A—C21A—C22A−178.54 (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—C24B−179.19 (9)
C22A—C23A—C24A—C25A−179.64 (10)C22B—C23B—C24B—C25B179.50 (9)

Hydrogen-bond geometry (Å, °)

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, y−1/2, −z+3/2; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+1, −y, −z+2; (iv) x, −y−1/2, z−3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2746).

References

  • 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.
  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.
  • 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. [PubMed]
  • Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107.
  • Ng, S.-L., Patil, P. S., Razak, I. A., Fun, H.-K. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o1228–o1230.
  • Ng, S.-L., Razak, I. A., Fun, H.-K., Shettigar, V., Patil, P. S. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o2175–o2177.
  • Satyanarayana, M., Tiwari, P., Tripathi, B. K., Srivastava, A. K. & Pratap, R. (2004). Bioorg. Med. Chem. Lett.12, 883–889. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Xue, C. X., Cui, S. Y., Liu, M. C., Hu, Z. D. & Fan, B. T. (2004). Eur. J. Med. Chem.39, 745–753. [PubMed]
  • Yayli, N., Ucuncu, O., Yasar, A., Kucuk, M., Yayli, N., Akyuz, E. & Alpay-Karaoglu, S. (2006). Turk. J. Chem.30, 505–514.
  • Zhao, L. M., Jin, H. S., Sun, L. P., Piao, H. R. & Quan, Z. S. (2005). Chem. Lett.15, 5027–5029. [PubMed]

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