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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, cDepartment of Chemistry, P.A. College of Engineering, Mangalore 574 153, India, and dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 28 February 2011; accepted 4 March 2011; online 12 March 2011)

In the title compound, C17H16O4, the dihedral angle between the mean planes of the hy­droxy­phenyl and dimeth­oxy­phenyl rings is 5.9 (6)°. The mean plane of the prop-2-en-1-one group makes dihedral angles of 3.6 (0) and 2.6 (7)° with the hy­droxy­phenyl and dimeth­oxy­phenyl rings, respectively. An intra­molecular O—H⋯O hydrogen bond occurs. The crystal packing is stabilized by weak inter­molecular C—H⋯O contacts and ππ stacking inter­actions [centroid–centroid distance = 3.6571 (8) Å].

Related literature

For related structures, see: Butcher et al. (2006[Butcher, R. J., Yathirajan, H. S., Anilkumar, H. G., Sarojini, B. K. & Narayana, B. (2006). Acta Cryst. E62, o1633-o1635.]); Cao et al. (2005[Cao, D.-X., Li, G.-Z., Xue, G., Yu, W.-T. & Liu, Z.-Q. (2005). Acta Cryst. E61, o977-o979.]); Harrison et al. (2007[Harrison, W. T. A., Kumari, V., Ravindra, H. J. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2928.]); Jasinski et al. (2010[Jasinski, J. P., Butcher, R. J., Chidan Kumar, C. S., Yathirajan, H. S. & Mayekar, A. N. (2010). Acta Cryst. E66, o2936-o2937.], 2011a[Jasinski, J. P., Butcher, R. J., Siddaraju, B. P., Narayana, B. & Yathirajan, H. S. (2011a). Acta Cryst. E67, o313-o314.],b[Jasinski, J. P., Butcher, R. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011b). Acta Cryst. E67, o352-o353.]); Ngaini et al. (2009[Ngaini, Z., Fadzillah, S. M. H., Hussain, H., Razak, I. A. & Fun, H.-K. (2009). Acta Cryst. E65, o1301-o1302.]); Radha Krishna et al. (2005[Radha Krishna, J., Jagadeesh Kumar, N., Krishnaiah, M., Venkata Rao, C., Koteswara Rao, Y. & Puranik, V. G. (2005). Acta Cryst. E61, o1323-o1325.]); Sharma et al. (1997[Sharma, N. K., Kumar, R., Parmar, V. S. & Errington, W. (1997). Acta Cryst. C53, 1438-1440.]); Wu et al. (2005[Wu, H., Xu, Z. & Liang, Y.-M. (2005). Acta Cryst. E61, o1434-o1435.]). For standard bond lengths, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16O4

  • Mr = 284.30

  • Monoclinic, P 21 /c

  • a = 14.2315 (2) Å

  • b = 8.0292 (1) Å

  • c = 13.6027 (2) Å

  • β = 110.0531 (14)°

  • V = 1460.11 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.76 mm−1

  • T = 295 K

  • 0.51 × 0.47 × 0.35 mm

Data collection
  • Oxford Diffraction Gemini R diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Oxfordshire, England.]) Tmin = 0.065, Tmax = 1.000

  • 6676 measured reflections

  • 3014 independent reflections

  • 2336 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.152

  • S = 1.12

  • 3014 reflections

  • 193 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯O2 0.82 1.77 2.5021 (18) 147
C14—H14A⋯O2i 0.93 2.51 3.4250 (19) 170
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Oxfordshire, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Oxfordshire, England.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In continuation to our studies on crystal structures of chalcones (Jasinski et al., 2010, 2011a, 2011b), we report here the synthesis (Fig. 1) and crystal structure of a new chalcone, C17H16O4, (I). The dihedral angle between the mean planes of the hydroxyphenyl and dimethoxyphenyl rings is 5.9 (6)° (Fig. 2). The mean plane of the prop-2-en-1-one group, the active site in this molecule, makes angles of 3.6 (0)° and 2.6 (7)°, respectively, with the hydroxyphenyl and dimethoxyphenyl rings. Bond lengths and angles are normal (Allen et al., 1987) and corespond to those observed in related compounds (Butcher et al., 2006; Cao et al., 2005; Harrison et al., 2007; Jasinski et al., 2010, 2011a, 2011b; Ngaini et al., 2009; Radha Krishna et al., 2005; Sharma et al., 1997; Wu et al., 2005). Crystal packing is stabilized by O—H···O intramolecular hydrogen bonds, weak C—H···O intermolecular (Table 1) and ππ stacking interactions (Table 2, Fig. 3).

Related literature top

For related structures, see: Butcher et al. (2006); Cao et al. (2005); Harrison et al. (2007); Jasinski et al. (2010, 2011a,b); Ngaini et al. (2009); Radha Krishna et al. (2005); Sharma et al. (1997); Wu et al. (2005). For standard bond lengths, see: Allen et al. (1987).

Experimental top

2-Hydroxyacetophenone (1.36 g, 0.01 mol) was mixed with 3,4-dimethoxybenzaldehyde (1.66 g, 0.01 mol) and dissolved in ethanol (40 ml) (Fig. 1). To this solution, 5 mL of KOH (50%) was added at 278 K. The reaction mixture stirred overnight at room temperature and poured on to crushed ice. The pH of this mixture was adjusted to 3–4 with 2 M HCl aqueous solution. The resulting crude solid was filtered, washed successively with dilute HCl solution and distilled water and finally recrystallized from ethanol (95%) to give the pure chalcone. Crystals suitable for X-ray diffraction studies were grown by the slow evaporation of the solution of the compound in ethyl alcohol (m.p.: 378–381 K). Composition: Found (Calculated) for C17H16O4, C 75.25 (75.28); H: 5.98 (5.92).

Refinement top

The hydroxyl hydrogem (H1A) was located by a Fourier map, fixed at 0.82 Å and refined using the riding model. All of the remaining H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.93Å (CH), 0.96Å (CH3). Isotropic displacement parameters for these atoms were set to 1.19–1.20 (CH), 1.49 (CH3) or 1.49 (OH) times Ueq of the parent atom.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Reaction scheme for (I).
[Figure 2] Fig. 2. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids. Dashed line indicates an O—H···O intramolecular bond.
[Figure 3] Fig. 3. Packing diagram of the title compound viewed down the c axis. Dashed lines indicate O—H···O intramolecular hydrogen bonds and weak C—H···O intermolecular interactions.
(E)-3-(3,4-Dimethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one top
Crystal data top
C17H16O4F(000) = 600
Mr = 284.30Dx = 1.293 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 4075 reflections
a = 14.2315 (2) Åθ = 5.5–77.1°
b = 8.0292 (1) ŵ = 0.76 mm1
c = 13.6027 (2) ÅT = 295 K
β = 110.0531 (14)°Prism, pale yellow
V = 1460.11 (3) Å30.51 × 0.47 × 0.35 mm
Z = 4
Data collection top
Oxford Diffraction Gemini R
diffractometer
3014 independent reflections
Radiation source: fine-focus sealed tube2336 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 10.5081 pixels mm-1θmax = 77.4°, θmin = 6.4°
ϕ and ω scansh = 1716
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 99
Tmin = 0.065, Tmax = 1.000l = 1517
6676 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.12 w = 1/[σ2(Fo2) + (0.0968P)2 + 0.0366P]
where P = (Fo2 + 2Fc2)/3
3014 reflections(Δ/σ)max < 0.001
193 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C17H16O4V = 1460.11 (3) Å3
Mr = 284.30Z = 4
Monoclinic, P21/cCu Kα radiation
a = 14.2315 (2) ŵ = 0.76 mm1
b = 8.0292 (1) ÅT = 295 K
c = 13.6027 (2) Å0.51 × 0.47 × 0.35 mm
β = 110.0531 (14)°
Data collection top
Oxford Diffraction Gemini R
diffractometer
3014 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
2336 reflections with I > 2σ(I)
Tmin = 0.065, Tmax = 1.000Rint = 0.021
6676 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 1.12Δρmax = 0.18 e Å3
3014 reflectionsΔρmin = 0.18 e Å3
193 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.88704 (12)0.7981 (2)0.17236 (10)0.0876 (4)
H1A0.83510.74550.16170.131*
O20.76002 (8)0.62603 (18)0.21587 (8)0.0737 (4)
O30.63965 (8)0.32097 (14)0.68696 (7)0.0648 (3)
O40.47076 (8)0.18452 (14)0.59076 (8)0.0638 (3)
C10.90537 (11)0.71605 (18)0.34900 (11)0.0558 (3)
C20.94152 (13)0.7937 (2)0.27531 (14)0.0670 (4)
C31.03495 (17)0.8674 (3)0.3086 (2)0.0921 (6)
H3A1.05880.91730.26010.110*
C41.09263 (17)0.8676 (3)0.4123 (2)0.1082 (8)
H4A1.15530.91770.43380.130*
C51.05822 (17)0.7935 (3)0.4855 (2)0.1030 (8)
H5A1.09790.79340.55590.124*
C60.96559 (14)0.7203 (2)0.45407 (14)0.0744 (5)
H6A0.94250.67260.50380.089*
C70.80752 (10)0.63257 (19)0.31157 (10)0.0536 (3)
C80.76620 (10)0.55612 (18)0.38547 (10)0.0545 (3)
H8A0.80250.55980.45680.065*
C90.67732 (10)0.48135 (18)0.35199 (10)0.0531 (3)
H9A0.64480.47940.27990.064*
C100.62489 (10)0.40250 (17)0.41423 (10)0.0502 (3)
C110.66334 (10)0.40028 (17)0.52433 (10)0.0505 (3)
H11A0.72540.44810.55930.061*
C120.61015 (10)0.32804 (17)0.58086 (10)0.0497 (3)
C130.51638 (10)0.25396 (17)0.52792 (10)0.0501 (3)
C140.47888 (10)0.25475 (19)0.41980 (11)0.0553 (3)
H14A0.41730.20580.38450.066*
C150.53281 (10)0.3283 (2)0.36387 (10)0.0567 (4)
H15A0.50680.32790.29110.068*
C160.73098 (14)0.3979 (3)0.74455 (12)0.0755 (5)
H16A0.78430.34720.72710.113*
H16B0.74320.38450.81800.113*
H16C0.72760.51440.72780.113*
C170.37373 (12)0.1167 (2)0.54210 (14)0.0681 (4)
H17A0.32870.20330.50560.102*
H17B0.35050.06920.59440.102*
H17C0.37630.03180.49340.102*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1035 (10)0.1039 (11)0.0682 (8)0.0071 (8)0.0458 (7)0.0160 (7)
O20.0640 (6)0.1134 (10)0.0441 (5)0.0038 (6)0.0193 (5)0.0099 (5)
O30.0718 (6)0.0810 (7)0.0380 (5)0.0125 (5)0.0142 (4)0.0055 (4)
O40.0672 (6)0.0759 (7)0.0503 (5)0.0126 (5)0.0226 (5)0.0033 (5)
C10.0575 (7)0.0584 (8)0.0558 (8)0.0092 (6)0.0248 (6)0.0038 (6)
C20.0745 (10)0.0630 (9)0.0739 (10)0.0041 (7)0.0389 (8)0.0062 (7)
C30.0863 (13)0.0863 (13)0.1165 (18)0.0127 (10)0.0514 (13)0.0123 (12)
C40.0760 (13)0.1022 (16)0.141 (2)0.0257 (11)0.0305 (14)0.0055 (15)
C50.0775 (12)0.1164 (18)0.0948 (15)0.0212 (12)0.0034 (11)0.0067 (13)
C60.0695 (9)0.0837 (11)0.0647 (10)0.0050 (8)0.0159 (8)0.0055 (8)
C70.0538 (7)0.0663 (8)0.0440 (6)0.0109 (6)0.0210 (5)0.0039 (6)
C80.0574 (7)0.0671 (8)0.0416 (6)0.0069 (6)0.0205 (5)0.0025 (6)
C90.0590 (7)0.0632 (8)0.0407 (6)0.0082 (6)0.0218 (5)0.0010 (6)
C100.0552 (7)0.0572 (7)0.0408 (6)0.0063 (5)0.0197 (5)0.0008 (5)
C110.0523 (7)0.0570 (7)0.0417 (6)0.0003 (5)0.0154 (5)0.0014 (5)
C120.0572 (7)0.0530 (7)0.0377 (6)0.0026 (5)0.0145 (5)0.0009 (5)
C130.0547 (7)0.0526 (7)0.0452 (7)0.0027 (5)0.0201 (5)0.0008 (6)
C140.0495 (6)0.0680 (8)0.0471 (7)0.0012 (6)0.0147 (5)0.0056 (6)
C150.0568 (7)0.0755 (9)0.0364 (6)0.0049 (6)0.0143 (5)0.0027 (6)
C160.0726 (10)0.1061 (14)0.0400 (7)0.0133 (9)0.0094 (6)0.0028 (8)
C170.0642 (9)0.0744 (10)0.0710 (10)0.0079 (7)0.0300 (7)0.0029 (8)
Geometric parameters (Å, º) top
O1—C21.349 (2)C8—C91.331 (2)
O1—H1A0.8200C8—H8A0.9300
O2—C71.2454 (16)C9—C101.4517 (19)
O3—C121.3591 (15)C9—H9A0.9300
O3—C161.4094 (19)C10—C151.388 (2)
O4—C131.3578 (16)C10—C111.4073 (17)
O4—C171.4193 (19)C11—C121.3784 (19)
C1—C61.392 (2)C11—H11A0.9300
C1—C21.418 (2)C12—C131.4121 (19)
C1—C71.470 (2)C13—C141.3820 (18)
C2—C31.382 (3)C14—C151.384 (2)
C3—C41.367 (3)C14—H14A0.9300
C3—H3A0.9300C15—H15A0.9300
C4—C51.386 (4)C16—H16A0.9600
C4—H4A0.9300C16—H16B0.9600
C5—C61.371 (3)C16—H16C0.9600
C5—H5A0.9300C17—H17A0.9600
C6—H6A0.9300C17—H17B0.9600
C7—C81.4623 (19)C17—H17C0.9600
C2—O1—H1A109.5C15—C10—C11118.47 (12)
C12—O3—C16117.53 (12)C15—C10—C9119.11 (12)
C13—O4—C17117.57 (11)C11—C10—C9122.41 (12)
C6—C1—C2118.03 (15)C12—C11—C10120.76 (12)
C6—C1—C7122.90 (14)C12—C11—H11A119.6
C2—C1—C7119.06 (13)C10—C11—H11A119.6
O1—C2—C3118.35 (17)O3—C12—C11125.54 (12)
O1—C2—C1121.78 (15)O3—C12—C13114.69 (12)
C3—C2—C1119.88 (18)C11—C12—C13119.77 (12)
C4—C3—C2120.5 (2)O4—C13—C14125.33 (13)
C4—C3—H3A119.7O4—C13—C12115.10 (11)
C2—C3—H3A119.7C14—C13—C12119.56 (12)
C3—C4—C5120.4 (2)C13—C14—C15120.15 (13)
C3—C4—H4A119.8C13—C14—H14A119.9
C5—C4—H4A119.8C15—C14—H14A119.9
C6—C5—C4119.9 (2)C14—C15—C10121.29 (12)
C6—C5—H5A120.1C14—C15—H15A119.4
C4—C5—H5A120.1C10—C15—H15A119.4
C5—C6—C1121.2 (2)O3—C16—H16A109.5
C5—C6—H6A119.4O3—C16—H16B109.5
C1—C6—H6A119.4H16A—C16—H16B109.5
O2—C7—C8119.91 (13)O3—C16—H16C109.5
O2—C7—C1119.43 (13)H16A—C16—H16C109.5
C8—C7—C1120.65 (12)H16B—C16—H16C109.5
C9—C8—C7120.86 (12)O4—C17—H17A109.5
C9—C8—H8A119.6O4—C17—H17B109.5
C7—C8—H8A119.6H17A—C17—H17B109.5
C8—C9—C10127.97 (12)O4—C17—H17C109.5
C8—C9—H9A116.0H17A—C17—H17C109.5
C10—C9—H9A116.0H17B—C17—H17C109.5
C6—C1—C2—O1178.66 (16)C8—C9—C10—C112.0 (2)
C7—C1—C2—O12.4 (2)C15—C10—C11—C120.9 (2)
C6—C1—C2—C31.4 (2)C9—C10—C11—C12178.26 (12)
C7—C1—C2—C3177.60 (16)C16—O3—C12—C111.9 (2)
O1—C2—C3—C4179.4 (2)C16—O3—C12—C13177.80 (14)
C1—C2—C3—C40.6 (3)C10—C11—C12—O3179.11 (12)
C2—C3—C4—C50.1 (4)C10—C11—C12—C130.6 (2)
C3—C4—C5—C60.4 (4)C17—O4—C13—C144.4 (2)
C4—C5—C6—C11.1 (4)C17—O4—C13—C12176.45 (13)
C2—C1—C6—C51.6 (3)O3—C12—C13—O41.09 (18)
C7—C1—C6—C5177.29 (19)C11—C12—C13—O4179.19 (12)
C6—C1—C7—O2176.19 (15)O3—C12—C13—C14179.70 (13)
C2—C1—C7—O22.7 (2)C11—C12—C13—C140.0 (2)
C6—C1—C7—C83.2 (2)O4—C13—C14—C15179.36 (13)
C2—C1—C7—C8177.88 (13)C12—C13—C14—C150.2 (2)
O2—C7—C8—C91.0 (2)C13—C14—C15—C100.1 (2)
C1—C7—C8—C9179.55 (13)C11—C10—C15—C140.6 (2)
C7—C8—C9—C10178.80 (13)C9—C10—C15—C14178.54 (13)
C8—C9—C10—C15178.87 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.821.772.5021 (18)147
C14—H14A···O2i0.932.513.4250 (19)170
Symmetry code: (i) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H16O4
Mr284.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)14.2315 (2), 8.0292 (1), 13.6027 (2)
β (°) 110.0531 (14)
V3)1460.11 (3)
Z4
Radiation typeCu Kα
µ (mm1)0.76
Crystal size (mm)0.51 × 0.47 × 0.35
Data collection
DiffractometerOxford Diffraction Gemini R
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.065, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
6676, 3014, 2336
Rint0.021
(sin θ/λ)max1)0.633
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.152, 1.12
No. of reflections3014
No. of parameters193
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O20.821.772.5021 (18)147
C14—H14A···O2i0.932.513.4250 (19)170
Symmetry code: (i) x+1, y1/2, z+1/2.
Selected geometric parmeters (Å): Cg···Cg π stacking interactions, Cg2 is the centroid of ring C10—C15 [Symmetry code: (i) 1-x, 1-y, 1-z] top
CgI···CgJCg···Cg (Å)CgI Perp (Å)Cgj Perp (Å)Slippage (Å)
Cg2···Cg2i3.6571 (8)3.5389 (6)3.5389 (6)0.92 (2)
 

Acknowledgements

BKS thanks the BRNS, DAE, Government of India (grant No. 2008/34/05-BRNS/457). VMK thanks P·A. College of Engineering for the research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

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