PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1133–o1134.
Published online 2009 April 25. doi:  10.1107/S1600536809014925
PMCID: PMC2977806

(E)-3-[4-(Dodec­yloxy)phen­yl]-1-(2-hydroxy­phen­yl)prop-2-en-1-one

Abstract

In the title compound, C27H36O3, the asymmetric unit consists of two crystallographically independent mol­ecules. The aromatic rings form dihedral angles of 17.1 (2) and 17.6 (2)° in the two molecules. In both mol­ecules, the enone groups adopt an scis conformation and the alkoxyl chains are in trans conformations curving out of the zigzag plane. Intra­molecular O—H(...)O hydrogen bonds involving the keto and hydr­oxy groups generate S(6) ring motifs. The mol­ecules are stacked alternately in a head-to-tail fashion along the a axis and the crystal structure is stabilized by weak C—H(...)π inter­actions. The crystal studied was a non-merohedral twin, the ratio of components being 0.788 (2):0.212 (2).

Related literature

For general background to the biological activity of chalcone derivatives, see: Bhat et al. (2005 [triangle]); Xue et al. (2004 [triangle]); Satyanarayana et al. (2004 [triangle]); Zhao et al. (2005 [triangle]); Lee et al. (2006 [triangle]). For related structures, see: Ng et al. (2006 [triangle]); Razak et al. (2009 [triangle]); Ngaini, Fadzillah et al. (2009 [triangle]); Ngaini, Rahman et al. (2009 [triangle]). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1133-scheme1.jpg

Experimental

Crystal data

  • C27H36O3
  • M r = 408.56
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1133-efi1.jpg
  • a = 7.4953 (6) Å
  • b = 13.4714 (9) Å
  • c = 23.7874 (18) Å
  • α = 75.116 (4)°
  • β = 83.876 (5)°
  • γ = 84.669 (5)°
  • V = 2302.7 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 K
  • 0.55 × 0.13 × 0.06 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.960, T max = 0.996
  • 8571 measured reflections
  • 8571 independent reflections
  • 4737 reflections with I > 2σ(I)

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.206
  • S = 1.03
  • 8571 reflections
  • 546 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.30 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014925/lh2802sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014925/lh2802Isup2.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 for 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 Malaysian Government and Universiti Malaysia Sarawak for providing a scholarship for postgraduate studies.

supplementary crystallographic information

Comment

Chalcone derivatives are of interest because of their biological properties such as anticancer (Bhat et al., 2005), antimalarial (Xue et al., 2004), antiangiogenic and antitumour (Lee et al., 2006), antiplatelet activity (Zhao et al., 2005) and antihyperglycemic activity (Satyanarayana et al., 2004). As part of our studies on their biological properties, we have synthesized the title chalcone derivative, (I). Its antibacterial activities were tested against E. coli ATCC 8739 and showed antimicrobial activity. The structure determination of (I) was carried out and is reported in this paper.

The asymmetric unit of (I) consists of two crystallographically independent molecules, A and B (Fig.1). The bond lengths show normal values (Allen et al., 1987). The mean plane through the enone moiety (O2/C7/C8/C9) makes dihedral angles with the two benzene rings with values of 3.4 (2)° (C1—C6) and 16.0 (2)° (C10—C15) in molecule A and 7.8 (2)° (C1—C6) and 15.7 (2)° (C10—C15) in molecule B. The two benzene rings form dihedral angles with each other of 17.1 (2)° and 17.6 (2)° in molecules A and B, respectively.

The enone moieties adopt s-cis conformation with the O2—C7—C8—C9 torsion angle being 6.5 (5)° for molecule A and 8.8 (5)° for B. In what follows, the distortion of the angles is relative to what is expected in terms of hybridization principles. In molecule A, the slight enlargement of the C5A—C6A—C7A (122.4 (3)°) and C6A—C7A—C8A (121.9 (3)°) angles may be the result of the short H5AA···H8AA (2.14 Å) contact whereas the short H8AA···H11A (2.35 Å) contact may widen the C8A—C9A—C10A (129.0 (3)°) and C9A—C10A—C11A (123.0 (3)°) angles. The short H14A···H16A (2.26 Å) contact may result in the opening of the O3A—C13A—C14A (124.9 (3)°) angle. Likewise, in molecule B, a close interatomic contact between H5BA and H8BA (2.13 Å) may result in the widening of the C5B—C6B—C7B (123.1 (3)°) and C6B—C7B—C8B (121.2 (3)°) angles whereas the opening of C8B—C9B—C10B and C9B—C10B—C11B angles to 128.6 (3)° and 123.0 (3)°, respectively, may be the result of the close H8BA···H11B (2.30 Å) contact. Similar strain induced by a short H14B···H16C (2.26 Å) contact may result in the opening of the O3B—C13B—C14B (125.2 (3)°) angle. These features were also reported in related structures (Ng et al., 2006; Razak et al., 2009; Ngaini, Fadzillah et al., 2009; Ngaini, Rahman et al., 2009).

The conformation throughout the zigzag alkoxyl tails in both molecules is trans with the largest deviation from the ideal value being -174.4 (3)° for the C19A—C20A—C21A—C22A torsion angle in molecule A and -173.5 (3)° for the C17B—C18B—C19B—C20B torsion angle in B. Even though the torsion angle C16—O3—C13—C14 in each molecule is -6.8 (5)° for A and -12.2 (5)° for B, the alkoxyl chains curve out of the zigzag plane with the least-squares plane through the chain making dihedral angle with the attached benzene ring of 17.02 (19)° [maximum deviation of -0.302 (4)Å at C21A] and 16.73 (19)° [maximum deviation of -0.256 (4)Å at C21B], for molecules A and B, respectively.

An intramolecular O-H···O interaction involving the keto and hydroxy groups (Table 1) in both molecules generates S(6) ring motifs (Bernstein et al., 1995). In the crystal structure, the molecules are stacked alternately along the a axis in a head-to-tail manner (Fig. 2). In the absence of conventional hydrogen bonds, the crystal structure is stabilized by weak C—H···π interactions (Table 1).

Experimental

A mixture of 2-hydroxyacetophenone (2.72 ml, 20 mmol) and 4-dodecyloxybenzaldehyde (5.81 ml, 20 mmol) and KOH (4.04 g, 72 mmol) in 60 ml of methanol was heated at reflux for 10 h. The reaction was cooled to room temperature and acidified with cold diluted HCl (2 N). The resulting precipitate was filtered, washed and dried. After redissolving in hexane, followed by a few days of slow evaporation, crystals were collected.

Refinement

All H atoms were positioned geometrically and refined using a riding model. The Uiso(H) values were constrained to be 1.5Ueq(C,O) (methyl H and hydroxyl H atoms) and 1.2Ueq(C) (other H atoms). The rotating model group was considered for the methyl group. The crystal is a twin with a refined BASF = 0.212 (2).

Figures

Fig. 1.
The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. Intramolecular interactions were shown as dashed line.
Fig. 2.
Part of the crystal structure of (I) viewed along the a axis.

Crystal data

C27H36O3Z = 4
Mr = 408.56F(000) = 888
Triclinic, P1Dx = 1.179 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4953 (6) ÅCell parameters from 3668 reflections
b = 13.4714 (9) Åθ = 2.7–28.0°
c = 23.7874 (18) ŵ = 0.08 mm1
α = 75.116 (4)°T = 100 K
β = 83.876 (5)°Needle, yellow
γ = 84.669 (5)°0.55 × 0.13 × 0.06 mm
V = 2302.7 (3) Å3

Data collection

Bruker APEXII diffractometer8571 independent reflections
Radiation source: sealed tube4737 reflections with I > 2σ(I)
graphiteRint = 0.0000
π and ω scansθmax = 25.5°, θmin = 0.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −8→9
Tmin = 0.960, Tmax = 0.996k = −16→16
8571 measured reflectionsl = −28→28

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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0924P)2 + 0.763P] where P = (Fo2 + 2Fc2)/3
8571 reflections(Δ/σ)max < 0.001
546 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.30 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
O1A0.6765 (4)0.69790 (18)0.78918 (11)0.0307 (6)
H1A0.66090.69850.75550.046*
O2A0.6335 (3)0.62359 (18)0.70527 (11)0.0290 (6)
O3A0.6291 (3)0.19687 (18)0.50595 (10)0.0255 (6)
C1A0.6917 (5)0.5994 (3)0.82144 (16)0.0249 (8)
C2A0.7137 (5)0.5837 (3)0.88068 (16)0.0273 (9)
H2AA0.71580.63970.89660.033*
C3A0.7324 (5)0.4852 (3)0.91544 (16)0.0294 (9)
H3AA0.74560.47510.95500.035*
C4A0.7320 (5)0.4007 (3)0.89221 (15)0.0288 (9)
H4AA0.74690.33440.91590.035*
C5A0.7094 (5)0.4154 (3)0.83407 (15)0.0256 (8)
H5AA0.70880.35850.81870.031*
C6A0.6871 (4)0.5145 (3)0.79750 (15)0.0210 (8)
C7A0.6563 (4)0.5329 (3)0.73494 (15)0.0220 (8)
C8A0.6552 (5)0.4480 (3)0.70683 (15)0.0235 (8)
H8AA0.65970.38020.72910.028*
C9A0.6477 (4)0.4687 (3)0.64905 (15)0.0231 (8)
H9AA0.64320.53810.62970.028*
C10A0.6455 (4)0.3974 (3)0.61220 (15)0.0214 (8)
C11A0.6156 (5)0.2928 (3)0.63470 (15)0.0230 (8)
H11A0.59880.26600.67490.028*
C12A0.6109 (4)0.2297 (3)0.59822 (15)0.0221 (8)
H12A0.59050.16060.61390.027*
C13A0.6362 (4)0.2674 (3)0.53777 (15)0.0203 (8)
C14A0.6673 (5)0.3704 (3)0.51432 (15)0.0229 (8)
H14A0.68620.39610.47410.028*
C15A0.6698 (5)0.4344 (3)0.55132 (15)0.0233 (8)
H15A0.68820.50370.53540.028*
C16A0.6352 (5)0.2302 (3)0.44325 (15)0.0236 (8)
H16A0.74100.26800.42770.028*
H16B0.52920.27460.43130.028*
C17A0.6417 (5)0.1341 (3)0.42151 (15)0.0252 (8)
H17A0.54010.09510.44060.030*
H17B0.75020.09230.43340.030*
C18A0.6386 (5)0.1513 (3)0.35641 (15)0.0233 (8)
H18A0.74410.18610.33680.028*
H18B0.53310.19530.34370.028*
C19A0.6354 (5)0.0500 (3)0.33918 (15)0.0240 (8)
H19A0.73600.00460.35500.029*
H19B0.52610.01780.35750.029*
C20A0.6443 (5)0.0575 (3)0.27412 (15)0.0255 (8)
H20A0.75420.08850.25540.031*
H20B0.54370.10230.25780.031*
C21A0.6396 (5)−0.0469 (3)0.26067 (15)0.0252 (8)
H21A0.7325−0.09350.28060.030*
H21B0.5246−0.07460.27640.030*
C22A0.6664 (5)−0.0442 (3)0.19601 (15)0.0246 (8)
H22A0.7767−0.01160.17940.029*
H22B0.5678−0.00250.17650.029*
C23A0.6765 (5)−0.1509 (3)0.18409 (15)0.0251 (8)
H23A0.7717−0.19360.20510.030*
H23B0.5641−0.18230.19920.030*
C24A0.7112 (5)−0.1494 (3)0.11987 (15)0.0265 (9)
H24A0.8193−0.11390.10410.032*
H24B0.6119−0.11050.09930.032*
C25A0.7332 (5)−0.2558 (3)0.10808 (15)0.0276 (9)
H25A0.8331−0.29460.12840.033*
H25B0.6254−0.29150.12400.033*
C26A0.7664 (5)−0.2538 (3)0.04410 (15)0.0288 (9)
H26A0.8748−0.21870.02820.035*
H26B0.6671−0.21450.02370.035*
C27A0.7868 (6)−0.3608 (3)0.03238 (16)0.0336 (10)
H27A0.8210−0.3548−0.00840.050*
H27B0.6745−0.39250.04310.050*
H27C0.8778−0.40230.05510.050*
O1B0.1478 (4)−0.19486 (18)0.21550 (11)0.0324 (7)
H1B0.1245−0.19490.25000.049*
O2B0.0945 (3)−0.11900 (18)0.30324 (11)0.0290 (6)
O3B0.1502 (3)0.30711 (17)0.50023 (10)0.0251 (6)
C1B0.1699 (5)−0.0980 (3)0.18370 (16)0.0248 (8)
C2B0.2029 (5)−0.0831 (3)0.12353 (17)0.0296 (9)
H2BA0.2081−0.13900.10710.036*
C3B0.2280 (5)0.0137 (3)0.08821 (17)0.0328 (10)
H3BA0.24870.02300.04800.039*
C4B0.2224 (5)0.0976 (3)0.11249 (16)0.0310 (9)
H4BA0.23950.16310.08860.037*
C5B0.1917 (5)0.0837 (3)0.17155 (16)0.0252 (8)
H5BA0.18920.14020.18740.030*
C6B0.1638 (4)−0.0137 (3)0.20895 (16)0.0224 (8)
C7B0.1286 (4)−0.0313 (3)0.27275 (15)0.0224 (8)
C8B0.1362 (4)0.0522 (3)0.30173 (15)0.0230 (8)
H8BA0.14480.11950.27940.028*
C9B0.1308 (4)0.0320 (3)0.35977 (15)0.0217 (8)
H9BA0.1227−0.03670.37960.026*
C10B0.1359 (5)0.1032 (3)0.39596 (15)0.0231 (8)
C11B0.1184 (5)0.2102 (3)0.37436 (15)0.0234 (8)
H11B0.10370.23790.33500.028*
C12B0.1225 (5)0.2748 (3)0.41016 (16)0.0258 (9)
H12B0.11000.34570.39490.031*
C13B0.1452 (5)0.2351 (3)0.46948 (16)0.0230 (8)
C14B0.1622 (5)0.1297 (3)0.49237 (16)0.0249 (8)
H14B0.17600.10240.53190.030*
C15B0.1585 (5)0.0651 (3)0.45546 (16)0.0259 (9)
H15B0.1713−0.00570.47080.031*
C16B0.1390 (5)0.2755 (3)0.56305 (15)0.0237 (8)
H16C0.23510.22400.57610.028*
H16D0.02470.24660.57830.028*
C17B0.1564 (5)0.3710 (3)0.58335 (15)0.0247 (8)
H17C0.06580.42320.56660.030*
H17D0.27320.39690.56840.030*
C18B0.1366 (5)0.3554 (3)0.64911 (15)0.0245 (8)
H18C0.22920.30500.66630.029*
H18D0.02060.32890.66460.029*
C19B0.1520 (5)0.4559 (3)0.66580 (15)0.0249 (8)
H19C0.26130.48580.64570.030*
H19D0.05170.50310.65150.030*
C20B0.1549 (5)0.4484 (3)0.73017 (15)0.0231 (8)
H20C0.26000.40550.74440.028*
H20D0.04920.41530.75100.028*
C21B0.1587 (5)0.5525 (3)0.74315 (15)0.0248 (8)
H21C0.04800.59270.73210.030*
H21D0.25720.58820.71890.030*
C22B0.1799 (5)0.5491 (3)0.80653 (15)0.0255 (8)
H22C0.07800.51700.83070.031*
H22D0.28750.50630.81840.031*
C23B0.1928 (5)0.6542 (3)0.81750 (15)0.0262 (8)
H23C0.08370.69630.80670.031*
H23D0.29240.68710.79240.031*
C24B0.2195 (5)0.6512 (3)0.88035 (15)0.0262 (8)
H24C0.32100.60320.89250.031*
H24D0.11370.62520.90490.031*
C25B0.2525 (5)0.7555 (3)0.89035 (15)0.0276 (9)
H25C0.36010.78080.86660.033*
H25D0.15240.80410.87740.033*
C26B0.2743 (5)0.7519 (3)0.95361 (15)0.0281 (9)
H26C0.38180.70900.96540.034*
H26D0.17240.72000.97790.034*
C27B0.2879 (6)0.8576 (3)0.96430 (17)0.0361 (10)
H27D0.31220.84981.00410.054*
H27E0.17640.89790.95700.054*
H27F0.38350.89150.93860.054*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0346 (16)0.0267 (14)0.0343 (16)−0.0020 (11)−0.0117 (13)−0.0102 (12)
O2A0.0320 (15)0.0243 (14)0.0325 (15)−0.0041 (11)−0.0084 (12)−0.0074 (11)
O3A0.0314 (15)0.0256 (14)0.0220 (14)−0.0052 (11)−0.0045 (11)−0.0081 (11)
C1A0.0151 (19)0.027 (2)0.033 (2)−0.0025 (15)−0.0031 (16)−0.0072 (17)
C2A0.022 (2)0.031 (2)0.034 (2)−0.0024 (16)−0.0058 (17)−0.0160 (17)
C3A0.025 (2)0.043 (2)0.023 (2)−0.0046 (17)−0.0076 (17)−0.0121 (18)
C4A0.032 (2)0.029 (2)0.025 (2)−0.0052 (17)−0.0047 (17)−0.0054 (16)
C5A0.025 (2)0.027 (2)0.027 (2)−0.0053 (16)−0.0017 (16)−0.0102 (16)
C6A0.0143 (18)0.027 (2)0.024 (2)−0.0053 (15)−0.0010 (15)−0.0078 (16)
C7A0.0136 (18)0.025 (2)0.027 (2)−0.0029 (14)−0.0030 (15)−0.0055 (16)
C8A0.020 (2)0.024 (2)0.027 (2)−0.0006 (15)−0.0037 (16)−0.0048 (16)
C9A0.0148 (19)0.025 (2)0.029 (2)−0.0038 (14)−0.0057 (16)−0.0032 (16)
C10A0.0111 (18)0.028 (2)0.028 (2)−0.0022 (14)−0.0037 (15)−0.0102 (16)
C11A0.0179 (19)0.029 (2)0.023 (2)−0.0024 (15)−0.0054 (15)−0.0049 (16)
C12A0.0167 (19)0.0210 (19)0.028 (2)−0.0016 (14)−0.0059 (15)−0.0042 (16)
C13A0.0132 (18)0.0224 (19)0.029 (2)0.0012 (14)−0.0062 (15)−0.0130 (16)
C14A0.022 (2)0.027 (2)0.021 (2)−0.0014 (15)−0.0082 (16)−0.0062 (16)
C15A0.0210 (19)0.0197 (19)0.029 (2)−0.0052 (15)−0.0059 (16)−0.0035 (15)
C16A0.022 (2)0.026 (2)0.025 (2)−0.0033 (15)−0.0034 (16)−0.0098 (16)
C17A0.022 (2)0.030 (2)0.025 (2)−0.0019 (16)−0.0032 (16)−0.0084 (16)
C18A0.021 (2)0.025 (2)0.026 (2)−0.0010 (15)−0.0059 (16)−0.0073 (16)
C19A0.021 (2)0.026 (2)0.025 (2)−0.0035 (15)−0.0063 (16)−0.0045 (16)
C20A0.020 (2)0.030 (2)0.028 (2)−0.0011 (16)−0.0066 (16)−0.0077 (16)
C21A0.024 (2)0.0225 (19)0.031 (2)−0.0004 (15)−0.0100 (17)−0.0057 (16)
C22A0.022 (2)0.028 (2)0.026 (2)−0.0028 (15)−0.0058 (16)−0.0092 (16)
C23A0.021 (2)0.027 (2)0.027 (2)0.0012 (15)−0.0087 (16)−0.0061 (16)
C24A0.026 (2)0.029 (2)0.025 (2)−0.0020 (16)−0.0028 (16)−0.0075 (16)
C25A0.026 (2)0.030 (2)0.028 (2)−0.0037 (16)−0.0076 (17)−0.0067 (16)
C26A0.032 (2)0.029 (2)0.026 (2)−0.0017 (17)−0.0053 (17)−0.0075 (16)
C27A0.040 (3)0.036 (2)0.028 (2)−0.0003 (18)−0.0104 (19)−0.0130 (18)
O1B0.0386 (17)0.0279 (15)0.0329 (16)−0.0060 (12)−0.0052 (14)−0.0094 (12)
O2B0.0291 (15)0.0265 (14)0.0324 (15)−0.0084 (11)−0.0100 (12)−0.0040 (12)
O3B0.0280 (15)0.0236 (13)0.0250 (14)−0.0037 (11)−0.0058 (11)−0.0064 (11)
C1B0.0171 (19)0.027 (2)0.032 (2)−0.0024 (15)−0.0081 (16)−0.0070 (17)
C2B0.029 (2)0.029 (2)0.036 (2)−0.0018 (17)−0.0062 (18)−0.0156 (18)
C3B0.034 (2)0.040 (2)0.026 (2)0.0029 (18)−0.0060 (18)−0.0129 (18)
C4B0.034 (2)0.027 (2)0.030 (2)−0.0030 (17)−0.0050 (18)−0.0033 (17)
C5B0.025 (2)0.023 (2)0.030 (2)0.0008 (15)−0.0060 (17)−0.0105 (16)
C6B0.0127 (18)0.0245 (19)0.032 (2)0.0008 (14)−0.0059 (16)−0.0104 (16)
C7B0.0121 (18)0.027 (2)0.029 (2)−0.0004 (14)−0.0098 (15)−0.0060 (16)
C8B0.0172 (19)0.0221 (19)0.031 (2)−0.0010 (15)−0.0056 (16)−0.0068 (16)
C9B0.0161 (19)0.0212 (19)0.028 (2)−0.0028 (14)−0.0046 (15)−0.0053 (15)
C10B0.0159 (19)0.025 (2)0.030 (2)−0.0054 (15)−0.0028 (16)−0.0078 (16)
C11B0.0180 (19)0.030 (2)0.022 (2)−0.0036 (15)−0.0038 (15)−0.0049 (16)
C12B0.019 (2)0.026 (2)0.033 (2)−0.0031 (15)−0.0057 (16)−0.0059 (17)
C13B0.0152 (19)0.027 (2)0.028 (2)−0.0052 (15)−0.0021 (15)−0.0082 (16)
C14B0.025 (2)0.029 (2)0.021 (2)−0.0026 (16)−0.0044 (16)−0.0067 (16)
C15B0.023 (2)0.024 (2)0.030 (2)−0.0020 (15)−0.0055 (17)−0.0046 (16)
C16B0.0204 (19)0.026 (2)0.024 (2)−0.0050 (15)−0.0049 (15)−0.0031 (16)
C17B0.0174 (19)0.028 (2)0.029 (2)−0.0025 (15)−0.0041 (16)−0.0058 (16)
C18B0.020 (2)0.027 (2)0.026 (2)−0.0006 (15)−0.0043 (16)−0.0061 (16)
C19B0.022 (2)0.025 (2)0.027 (2)−0.0014 (15)−0.0054 (16)−0.0034 (16)
C20B0.0196 (19)0.025 (2)0.024 (2)−0.0023 (15)−0.0044 (15)−0.0046 (15)
C21B0.019 (2)0.027 (2)0.028 (2)−0.0025 (15)−0.0023 (16)−0.0061 (16)
C22B0.021 (2)0.028 (2)0.028 (2)0.0007 (15)−0.0052 (16)−0.0069 (16)
C23B0.024 (2)0.025 (2)0.030 (2)−0.0040 (16)−0.0052 (17)−0.0072 (16)
C24B0.025 (2)0.027 (2)0.028 (2)−0.0034 (16)−0.0079 (17)−0.0068 (16)
C25B0.027 (2)0.029 (2)0.028 (2)−0.0027 (16)−0.0070 (17)−0.0079 (16)
C26B0.030 (2)0.031 (2)0.024 (2)−0.0031 (17)−0.0047 (17)−0.0084 (16)
C27B0.044 (3)0.035 (2)0.033 (2)−0.0091 (19)−0.006 (2)−0.0123 (18)

Geometric parameters (Å, °)

O1A—C1A1.353 (4)O1B—C1B1.345 (4)
O1A—H1A0.8200O1B—H1B0.8200
O2A—C7A1.251 (4)O2B—C7B1.251 (4)
O3A—C13A1.366 (4)O3B—C13B1.361 (4)
O3A—C16A1.440 (4)O3B—C16B1.440 (4)
C1A—C2A1.396 (5)C1B—C2B1.392 (5)
C1A—C6A1.407 (5)C1B—C6B1.410 (5)
C2A—C3A1.374 (5)C2B—C3B1.375 (5)
C2A—H2AA0.9300C2B—H2BA0.9300
C3A—C4A1.388 (5)C3B—C4B1.392 (5)
C3A—H3AA0.9300C3B—H3BA0.9300
C4A—C5A1.372 (5)C4B—C5B1.366 (5)
C4A—H4AA0.9300C4B—H4BA0.9300
C5A—C6A1.400 (5)C5B—C6B1.403 (5)
C5A—H5AA0.9300C5B—H5BA0.9300
C6A—C7A1.484 (5)C6B—C7B1.473 (5)
C7A—C8A1.467 (5)C7B—C8B1.470 (5)
C8A—C9A1.337 (5)C8B—C9B1.334 (5)
C8A—H8AA0.9300C8B—H8BA0.9300
C9A—C10A1.459 (5)C9B—C10B1.449 (5)
C9A—H9AA0.9300C9B—H9BA0.9300
C10A—C15A1.403 (5)C10B—C15B1.399 (5)
C10A—C11A1.404 (5)C10B—C11B1.399 (5)
C11A—C12A1.366 (5)C11B—C12B1.370 (5)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.395 (5)C12B—C13B1.397 (5)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.387 (5)C13B—C14B1.384 (5)
C14A—C15A1.384 (5)C14B—C15B1.389 (5)
C14A—H14A0.9300C14B—H14B0.9300
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.508 (5)C16B—C17B1.507 (5)
C16A—H16A0.9700C16B—H16C0.9700
C16A—H16B0.9700C16B—H16D0.9700
C17A—C18A1.508 (5)C17B—C18B1.517 (5)
C17A—H17A0.9700C17B—H17C0.9700
C17A—H17B0.9700C17B—H17D0.9700
C18A—C19A1.525 (5)C18B—C19B1.522 (5)
C18A—H18A0.9700C18B—H18C0.9700
C18A—H18B0.9700C18B—H18D0.9700
C19A—C20A1.519 (5)C19B—C20B1.511 (5)
C19A—H19A0.9700C19B—H19C0.9700
C19A—H19B0.9700C19B—H19D0.9700
C20A—C21A1.525 (5)C20B—C21B1.515 (5)
C20A—H20A0.9700C20B—H20C0.9700
C20A—H20B0.9700C20B—H20D0.9700
C21A—C22A1.522 (5)C21B—C22B1.521 (5)
C21A—H21A0.9700C21B—H21C0.9700
C21A—H21B0.9700C21B—H21D0.9700
C22A—C23A1.529 (5)C22B—C23B1.518 (5)
C22A—H22A0.9700C22B—H22C0.9700
C22A—H22B0.9700C22B—H22D0.9700
C23A—C24A1.517 (5)C23B—C24B1.519 (5)
C23A—H23A0.9700C23B—H23C0.9700
C23A—H23B0.9700C23B—H23D0.9700
C24A—C25A1.520 (5)C24B—C25B1.531 (5)
C24A—H24A0.9700C24B—H24C0.9700
C24A—H24B0.9700C24B—H24D0.9700
C25A—C26A1.510 (5)C25B—C26B1.519 (5)
C25A—H25A0.9700C25B—H25C0.9700
C25A—H25B0.9700C25B—H25D0.9700
C26A—C27A1.528 (5)C26B—C27B1.523 (5)
C26A—H26A0.9700C26B—H26C0.9700
C26A—H26B0.9700C26B—H26D0.9700
C27A—H27A0.9600C27B—H27D0.9600
C27A—H27B0.9600C27B—H27E0.9600
C27A—H27C0.9600C27B—H27F0.9600
C1A—O1A—H1A109.5C1B—O1B—H1B109.5
C13A—O3A—C16A119.7 (3)C13B—O3B—C16B119.3 (3)
O1A—C1A—C2A117.3 (3)O1B—C1B—C2B117.2 (3)
O1A—C1A—C6A122.7 (3)O1B—C1B—C6B122.8 (3)
C2A—C1A—C6A120.0 (3)C2B—C1B—C6B120.0 (3)
C3A—C2A—C1A119.9 (3)C3B—C2B—C1B120.5 (3)
C3A—C2A—H2AA120.0C3B—C2B—H2BA119.7
C1A—C2A—H2AA120.0C1B—C2B—H2BA119.7
C2A—C3A—C4A120.8 (3)C2B—C3B—C4B120.1 (4)
C2A—C3A—H3AA119.6C2B—C3B—H3BA119.9
C4A—C3A—H3AA119.6C4B—C3B—H3BA119.9
C5A—C4A—C3A119.7 (3)C5B—C4B—C3B119.8 (3)
C5A—C4A—H4AA120.1C5B—C4B—H4BA120.1
C3A—C4A—H4AA120.1C3B—C4B—H4BA120.1
C4A—C5A—C6A121.1 (3)C4B—C5B—C6B121.7 (3)
C4A—C5A—H5AA119.5C4B—C5B—H5BA119.2
C6A—C5A—H5AA119.5C6B—C5B—H5BA119.2
C5A—C6A—C1A118.5 (3)C5B—C6B—C1B117.8 (3)
C5A—C6A—C7A122.4 (3)C5B—C6B—C7B123.1 (3)
C1A—C6A—C7A119.1 (3)C1B—C6B—C7B119.1 (3)
O2A—C7A—C8A119.3 (3)O2B—C7B—C8B119.0 (3)
O2A—C7A—C6A118.8 (3)O2B—C7B—C6B119.8 (3)
C8A—C7A—C6A121.9 (3)C8B—C7B—C6B121.2 (3)
C9A—C8A—C7A119.6 (3)C9B—C8B—C7B120.5 (3)
C9A—C8A—H8AA120.2C9B—C8B—H8BA119.7
C7A—C8A—H8AA120.2C7B—C8B—H8BA119.7
C8A—C9A—C10A129.0 (3)C8B—C9B—C10B128.6 (3)
C8A—C9A—H9AA115.5C8B—C9B—H9BA115.7
C10A—C9A—H9AA115.5C10B—C9B—H9BA115.7
C15A—C10A—C11A117.7 (3)C15B—C10B—C11B117.3 (3)
C15A—C10A—C9A119.3 (3)C15B—C10B—C9B119.7 (3)
C11A—C10A—C9A123.0 (3)C11B—C10B—C9B123.0 (3)
C12A—C11A—C10A120.7 (3)C12B—C11B—C10B121.3 (3)
C12A—C11A—H11A119.6C12B—C11B—H11B119.4
C10A—C11A—H11A119.6C10B—C11B—H11B119.4
C11A—C12A—C13A121.0 (3)C11B—C12B—C13B120.5 (3)
C11A—C12A—H12A119.5C11B—C12B—H12B119.8
C13A—C12A—H12A119.5C13B—C12B—H12B119.8
O3A—C13A—C14A124.9 (3)O3B—C13B—C14B125.2 (3)
O3A—C13A—C12A115.5 (3)O3B—C13B—C12B115.0 (3)
C14A—C13A—C12A119.6 (3)C14B—C13B—C12B119.8 (3)
C15A—C14A—C13A119.4 (3)C13B—C14B—C15B119.0 (3)
C15A—C14A—H14A120.3C13B—C14B—H14B120.5
C13A—C14A—H14A120.3C15B—C14B—H14B120.5
C14A—C15A—C10A121.7 (3)C14B—C15B—C10B122.2 (3)
C14A—C15A—H15A119.1C14B—C15B—H15B118.9
C10A—C15A—H15A119.1C10B—C15B—H15B118.9
O3A—C16A—C17A106.4 (3)O3B—C16B—C17B106.2 (3)
O3A—C16A—H16A110.4O3B—C16B—H16C110.5
C17A—C16A—H16A110.4C17B—C16B—H16C110.5
O3A—C16A—H16B110.4O3B—C16B—H16D110.5
C17A—C16A—H16B110.4C17B—C16B—H16D110.5
H16A—C16A—H16B108.6H16C—C16B—H16D108.7
C16A—C17A—C18A115.6 (3)C16B—C17B—C18B114.6 (3)
C16A—C17A—H17A108.4C16B—C17B—H17C108.6
C18A—C17A—H17A108.4C18B—C17B—H17C108.6
C16A—C17A—H17B108.4C16B—C17B—H17D108.6
C18A—C17A—H17B108.4C18B—C17B—H17D108.6
H17A—C17A—H17B107.4H17C—C17B—H17D107.6
C17A—C18A—C19A111.6 (3)C17B—C18B—C19B111.2 (3)
C17A—C18A—H18A109.3C17B—C18B—H18C109.4
C19A—C18A—H18A109.3C19B—C18B—H18C109.4
C17A—C18A—H18B109.3C17B—C18B—H18D109.4
C19A—C18A—H18B109.3C19B—C18B—H18D109.4
H18A—C18A—H18B108.0H18C—C18B—H18D108.0
C20A—C19A—C18A116.1 (3)C20B—C19B—C18B116.2 (3)
C20A—C19A—H19A108.3C20B—C19B—H19C108.2
C18A—C19A—H19A108.3C18B—C19B—H19C108.2
C20A—C19A—H19B108.3C20B—C19B—H19D108.2
C18A—C19A—H19B108.3C18B—C19B—H19D108.2
H19A—C19A—H19B107.4H19C—C19B—H19D107.4
C19A—C20A—C21A112.7 (3)C19B—C20B—C21B112.7 (3)
C19A—C20A—H20A109.0C19B—C20B—H20C109.1
C21A—C20A—H20A109.0C21B—C20B—H20C109.1
C19A—C20A—H20B109.0C19B—C20B—H20D109.1
C21A—C20A—H20B109.0C21B—C20B—H20D109.1
H20A—C20A—H20B107.8H20C—C20B—H20D107.8
C22A—C21A—C20A114.4 (3)C20B—C21B—C22B115.0 (3)
C22A—C21A—H21A108.6C20B—C21B—H21C108.5
C20A—C21A—H21A108.6C22B—C21B—H21C108.5
C22A—C21A—H21B108.6C20B—C21B—H21D108.5
C20A—C21A—H21B108.6C22B—C21B—H21D108.5
H21A—C21A—H21B107.6H21C—C21B—H21D107.5
C21A—C22A—C23A113.3 (3)C23B—C22B—C21B113.7 (3)
C21A—C22A—H22A108.9C23B—C22B—H22C108.8
C23A—C22A—H22A108.9C21B—C22B—H22C108.8
C21A—C22A—H22B108.9C23B—C22B—H22D108.8
C23A—C22A—H22B108.9C21B—C22B—H22D108.8
H22A—C22A—H22B107.7H22C—C22B—H22D107.7
C24A—C23A—C22A113.7 (3)C22B—C23B—C24B114.0 (3)
C24A—C23A—H23A108.8C22B—C23B—H23C108.7
C22A—C23A—H23A108.8C24B—C23B—H23C108.7
C24A—C23A—H23B108.8C22B—C23B—H23D108.7
C22A—C23A—H23B108.8C24B—C23B—H23D108.7
H23A—C23A—H23B107.7H23C—C23B—H23D107.6
C23A—C24A—C25A113.9 (3)C23B—C24B—C25B114.2 (3)
C23A—C24A—H24A108.8C23B—C24B—H24C108.7
C25A—C24A—H24A108.8C25B—C24B—H24C108.7
C23A—C24A—H24B108.8C23B—C24B—H24D108.7
C25A—C24A—H24B108.8C25B—C24B—H24D108.7
H24A—C24A—H24B107.7H24C—C24B—H24D107.6
C26A—C25A—C24A113.7 (3)C26B—C25B—C24B113.7 (3)
C26A—C25A—H25A108.8C26B—C25B—H25C108.8
C24A—C25A—H25A108.8C24B—C25B—H25C108.8
C26A—C25A—H25B108.8C26B—C25B—H25D108.8
C24A—C25A—H25B108.8C24B—C25B—H25D108.8
H25A—C25A—H25B107.7H25C—C25B—H25D107.7
C25A—C26A—C27A113.5 (3)C25B—C26B—C27B113.4 (3)
C25A—C26A—H26A108.9C25B—C26B—H26C108.9
C27A—C26A—H26A108.9C27B—C26B—H26C108.9
C25A—C26A—H26B108.9C25B—C26B—H26D108.9
C27A—C26A—H26B108.9C27B—C26B—H26D108.9
H26A—C26A—H26B107.7H26C—C26B—H26D107.7
C26A—C27A—H27A109.5C26B—C27B—H27D109.5
C26A—C27A—H27B109.5C26B—C27B—H27E109.5
H27A—C27A—H27B109.5H27D—C27B—H27E109.5
C26A—C27A—H27C109.5C26B—C27B—H27F109.5
H27A—C27A—H27C109.5H27D—C27B—H27F109.5
H27B—C27A—H27C109.5H27E—C27B—H27F109.5
O1A—C1A—C2A—C3A−179.1 (3)O1B—C1B—C2B—C3B−179.6 (3)
C6A—C1A—C2A—C3A0.6 (5)C6B—C1B—C2B—C3B−0.7 (5)
C1A—C2A—C3A—C4A0.8 (6)C1B—C2B—C3B—C4B0.7 (6)
C2A—C3A—C4A—C5A−1.2 (6)C2B—C3B—C4B—C5B−0.1 (6)
C3A—C4A—C5A—C6A0.2 (6)C3B—C4B—C5B—C6B−0.6 (6)
C4A—C5A—C6A—C1A1.2 (5)C4B—C5B—C6B—C1B0.6 (5)
C4A—C5A—C6A—C7A−177.9 (3)C4B—C5B—C6B—C7B−179.4 (3)
O1A—C1A—C6A—C5A178.1 (3)O1B—C1B—C6B—C5B178.9 (3)
C2A—C1A—C6A—C5A−1.5 (5)C2B—C1B—C6B—C5B0.1 (5)
O1A—C1A—C6A—C7A−2.8 (5)O1B—C1B—C6B—C7B−1.1 (5)
C2A—C1A—C6A—C7A177.6 (3)C2B—C1B—C6B—C7B180.0 (3)
C5A—C6A—C7A—O2A178.4 (3)C5B—C6B—C7B—O2B175.9 (3)
C1A—C6A—C7A—O2A−0.7 (5)C1B—C6B—C7B—O2B−4.1 (5)
C5A—C6A—C7A—C8A−2.7 (5)C5B—C6B—C7B—C8B−5.4 (5)
C1A—C6A—C7A—C8A178.2 (3)C1B—C6B—C7B—C8B174.7 (3)
O2A—C7A—C8A—C9A6.5 (5)O2B—C7B—C8B—C9B8.8 (5)
C6A—C7A—C8A—C9A−172.3 (3)C6B—C7B—C8B—C9B−169.9 (3)
C7A—C8A—C9A—C10A179.9 (3)C7B—C8B—C9B—C10B−179.7 (3)
C8A—C9A—C10A—C15A−168.6 (4)C8B—C9B—C10B—C15B−169.5 (4)
C8A—C9A—C10A—C11A13.0 (6)C8B—C9B—C10B—C11B10.8 (6)
C15A—C10A—C11A—C12A0.1 (5)C15B—C10B—C11B—C12B−0.2 (5)
C9A—C10A—C11A—C12A178.5 (3)C9B—C10B—C11B—C12B179.5 (3)
C10A—C11A—C12A—C13A0.2 (5)C10B—C11B—C12B—C13B0.3 (5)
C16A—O3A—C13A—C14A−6.8 (5)C16B—O3B—C13B—C14B−12.2 (5)
C16A—O3A—C13A—C12A173.7 (3)C16B—O3B—C13B—C12B168.4 (3)
C11A—C12A—C13A—O3A179.8 (3)C11B—C12B—C13B—O3B178.9 (3)
C11A—C12A—C13A—C14A0.3 (5)C11B—C12B—C13B—C14B−0.5 (5)
O3A—C13A—C14A—C15A179.5 (3)O3B—C13B—C14B—C15B−178.6 (3)
C12A—C13A—C14A—C15A−1.0 (5)C12B—C13B—C14B—C15B0.8 (5)
C13A—C14A—C15A—C10A1.4 (5)C13B—C14B—C15B—C10B−0.7 (5)
C11A—C10A—C15A—C14A−0.9 (5)C11B—C10B—C15B—C14B0.5 (5)
C9A—C10A—C15A—C14A−179.4 (3)C9B—C10B—C15B—C14B−179.2 (3)
C13A—O3A—C16A—C17A175.0 (3)C13B—O3B—C16B—C17B177.5 (3)
O3A—C16A—C17A—C18A176.8 (3)O3B—C16B—C17B—C18B176.5 (3)
C16A—C17A—C18A—C19A−176.9 (3)C16B—C17B—C18B—C19B−178.8 (3)
C17A—C18A—C19A—C20A−176.2 (3)C17B—C18B—C19B—C20B−173.5 (3)
C18A—C19A—C20A—C21A−179.7 (3)C18B—C19B—C20B—C21B−176.4 (3)
C19A—C20A—C21A—C22A−174.4 (3)C19B—C20B—C21B—C22B−174.4 (3)
C20A—C21A—C22A—C23A175.3 (3)C20B—C21B—C22B—C23B177.0 (3)
C21A—C22A—C23A—C24A−177.5 (3)C21B—C22B—C23B—C24B−178.3 (3)
C22A—C23A—C24A—C25A176.3 (3)C22B—C23B—C24B—C25B173.9 (3)
C23A—C24A—C25A—C26A179.6 (3)C23B—C24B—C25B—C26B178.6 (3)
C24A—C25A—C26A—C27A−179.5 (3)C24B—C25B—C26B—C27B−174.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1A—H1A···O2A0.821.792.513 (4)146
O1B—H1B···O2B0.821.812.530 (4)146
C22B—H22C···Cg1i0.972.773.654 (4)151
C16B—H16D···Cg2i0.973.003.736 (4)134
C17B—H17D···Cg20.972.823.612 (4)139
C22A—H22B···Cg30.972.933.765 (4)145

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2802).

References

  • 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.
  • Lee, Y. S., Lim, S. S., Shin, K. H., Kim, Y. S., Ohuchi, K. & Jung, S. H. (2006). Biol. Pharm. Bull.29, 1028–1031. [PubMed]
  • Ng, S.-L., Razak, I. A., Fun, H.-K., Shettigar, V., Patil, P. S. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o2175–o2177.
  • Ngaini, Z., Fadzillah, S. M. H., Rahman, N. I. A., Hussain, H., Razak, I. A. & Fun, H.-K. (2009). Acta Cryst. E65, o879–o880. [PMC free article] [PubMed]
  • Ngaini, Z., Rahman, N. I. A., Hussain, H., Razak, I. A. & Fun, H.-K. (2009). Acta Cryst. E65, o889–o890. [PMC free article] [PubMed]
  • Razak, I. A., Fun, H.-K., Ngaini, Z., Fadzillah, S. M. H. & Hussain, H. (2009). Acta Cryst. E65, o881–o882. [PMC free article] [PubMed]
  • 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]
  • Xue, C. X., Cui, S. Y., Liu, M. C., Hu, Z. D. & Fan, B. T. (2004). Eur. J. Med. Chem.39, 745–753. [PubMed]
  • Zhao, L. M., Jin, H. S., Sun, L. P., Piao, H. R. & Quan, Z. S. (2005). Chem. Lett 15, 5027–5029. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography