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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 4| April 2011| Page o756
doi:10.1107/S160053681100701X

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

Jerry P. Jasinski,a* Ray J. Butcher,b H. S. Yathirajan,c B.K. Sarojinid and V. Musthafa Khaleeld

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 Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and dDepartment of Chemistry, P. A. College of Engineering, Mangalore, 574 153, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 20 February 2011; accepted 23 February 2011; online 2 March 2011)

In the title compound, C15H11ClO2, the dihedral angle between the mean planes of the chloro­benzene and hy­droxy­benzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group makes an angle of 18.0 (1)° with the hy­droxy­phenyl ring and 11.5 (1)° with the chloro­phenyl ring. The crystal packing is stabilized by inter­molecular O—H⋯O hydrogen bonds, weak C—H⋯O, C—H⋯π and π–π stacking inter­actions [centroid–centroid distances = 3.7771 (7) and 3.6917 (7) Å].

Related literature

For the biological properties of chalcones, see: Nowakowska (2007[Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125-137.]) and for their role in tubulin polymerization inhibition, see: Edwards et al. (1989[Edwards, M. L., Sunkara, S. P. & Stemerick, D. M. (1989). US Patent No. 4 863 968, Sept. 5.]). For related structures, see: 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.]); Butcher et al. (2007a[Butcher, R. J., Jasinski, J. P., Narayana, B., Lakshmana, K. & Yathirajan, H. S. (2007a). Acta Cryst. E63, o3586.],b[Butcher, R. J., Jasinski, J. P., Narayana, B., Lakshmana, K. & Yathirajan, H. S. (2007b). Acta Cryst. E63, o3660.]); Narayana et al. (2007[Narayana, B., Lakshmana, K., Sarojini, B. K., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o4552.]); Sarojini et al. (2007a[Sarojini, B. K., Yathirajan, H. S., Mustafa, K., Sarfraz, H. & Bolte, M. (2007a). Acta Cryst. E63, o4448.],b[Sarojini, B. K., Yathirajan, H. S., Mustafa, K., Sarfraz, H. & Bolte, M. (2007b). Acta Cryst. E63, o4477.]). 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

  • C15H11ClO2

  • Mr = 258.69

  • Monoclinic, P 21 /n

  • a = 7.3570 (2) Å

  • b = 15.6450 (5) Å

  • c = 10.4954 (3) Å

  • β = 90.518 (3)°

  • V = 1207.97 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 200 K

  • 0.51 × 0.45 × 0.36 mm
Data collection

  • Oxford Diffraction Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.984, Tmax = 1.000

  • 10126 measured reflections

  • 4020 independent reflections

  • 2924 reflections with I > 2σ(I)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.115

  • S = 1.07

  • 4020 reflections

  • 164 parameters

  • H-atom parameters constrained

  • Δρmax = 0.38 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1O⋯O2i 0.84 1.83 2.6556 (12) 167
C6—H6A⋯O1ii 0.95 2.57 3.5070 (13) 169
C11—H11A⋯O1ii 0.95 2.55 3.3382 (15) 141
C14—H14A⋯Cg1iii 0.95 2.79 3.7090 (14) 163
Symmetry codes: (i) [x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100701X/sj5108sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100701X/sj5108Isup2.hkl

checkCIF report


Comment top

Chalcones, or 1,3-diaryl-2-propen-1-ones, belong to the flavonoid family. Chemically they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using the compounds or chalcone rich plant extracts as drugs or food preservatives. Chalcones have been reported to possess many useful properties, including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Nowakowska, 2007). Certain chalcone derivatives are reported to inhibit the polymerization of tubulin to form microtubules and are therefore antimitotic agents which can be used as antigout agents. The chalcone derivatives are also reported to inhibit the destruction of the myelin sheath in the central nervous system of multiple sclerosis patients and are thus useful in controlling the progressive nature of the disease (Edwards et al., 1989).

In a continuation of our studies on the crystal structures of chalcones (Jasinski et al., 2010, 2011a, 2011b), we report here the synthesis and crystal structure of the title compound, C15H11ClO2, (I), Fig. 2. The dihedral angle between the mean planes of the chlorobenzene and hydroxybenzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group, the active site in this molecule, makes angles of 18.0 (1)° with the hydroxy benzene and 11.5 (1)° with the chlorobenzene rings, respectively. Bond lengths are normal (Allen et al., 1987) and correspond to those observed in related compounds (Butcher et al., 2007a, 2007b; Narayana et al., 2007; Sarojini et al., 2007a, 2007b). Crystal packing is stabilized by O—H···O hydrogen bonds, weak C—H···O, C—H···Cg π—ring (Table 1) and π—π intermolecular stacking interactions (Table 2 & Fig. 3).

Related literature top

For the biological properties of chalcones, see: Nowakowska (2007) and for their role in tubulin polymerization inhibition, see: Edwards et al. (1989). For related structures, see: Jasinski et al. (2010, 2011a,b); Butcher et al. (2007a,b); Narayana et al. (2007); Sarojini et al. (2007a,b). For standard bond lengths, see: Allen et al., (1987).

Experimental top

4-Hydroxyacetophenone (1.36 g, 0.01 mol) was mixed with 4-chlorobenzaldeyde (1.40 g, 0.01 mol) and dissolved in ethanol (20 ml) (Fig. 1). To this solution 4 ml of KOH (50%) (10 mL) was added at 0°C. The reaction mixture was stirred for 4 h 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 yellow 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 acetone. M.P:419 K. Composition: Found (Calculated) for C15H11ClO2, C: 69.53 (69.64); H: 4.26 (4.29).

Refinement top

The hydroxyl hydrogem (H1O) was located by a Fourier map, fixed at 0.84 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 0.95Å (CH). Isotropic displacement parameters for these atoms were set to 1.18–1.21 (CH) or 1.18 (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 the preparation of (I).
[Figure 2] Fig. 2. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
[Figure 3] Fig. 3. Packing diagram of the title compound viewed down the a axis. Dashed lines indicate O—H···O hydrogen bonds and weak C—H···O intermolecular interactions.
(2E)-3-(4-Chlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one top
Crystal data top
C15H11ClO2F(000) = 536
Mr = 258.69Dx = 1.422 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4738 reflections
a = 7.3570 (2) Åθ = 4.7–32.4°
b = 15.6450 (5) ŵ = 0.31 mm−1
c = 10.4954 (3) ÅT = 200 K
β = 90.518 (3)°Irregular chunk, colorless
V = 1207.97 (6) Å30.51 × 0.45 × 0.36 mm
Z = 4
Data collection top
Oxford Diffraction Gemini
diffractometer		4020 independent reflections
Radiation source: fine-focus sealed tube2924 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 10.5081 pixels mm-1θmax = 32.6°, θmin = 4.7°
ϕ and ω scansh = −10→10
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		k = −23→17
Tmin = 0.984, Tmax = 1.000l = −11→15
10126 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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0648P)2]
where P = (Fo2 + 2Fc2)/3
4020 reflections(Δ/σ)max < 0.001
164 parametersΔρmax = 0.38 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C15H11ClO2V = 1207.97 (6) Å3
Mr = 258.69Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.3570 (2) ŵ = 0.31 mm−1
b = 15.6450 (5) ÅT = 200 K
c = 10.4954 (3) Å0.51 × 0.45 × 0.36 mm
β = 90.518 (3)°
Data collection top
Oxford Diffraction Gemini
diffractometer		4020 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)		2924 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 1.000Rint = 0.022
10126 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.07Δρmax = 0.38 e Å−3
4020 reflectionsΔρmin = −0.19 e Å−3
164 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
Cl0.13335 (5)0.12309 (2)0.03417 (3)0.03910 (12)
O10.83226 (11)−0.31714 (6)−0.88736 (8)0.0269 (2)
H1O0.7288−0.3393−0.89520.032*
O21.03166 (11)−0.08981 (6)−0.40899 (9)0.0300 (2)
C10.86149 (15)−0.16357 (7)−0.56445 (10)0.0217 (2)
C21.01626 (15)−0.18219 (7)−0.63990 (11)0.0233 (2)
H2A1.1307−0.1587−0.61620.028*
C31.00442 (15)−0.23337 (7)−0.74638 (11)0.0240 (2)
H3A1.1090−0.2440−0.79640.029*
C40.83821 (15)−0.26923 (7)−0.77995 (11)0.0218 (2)
C50.68456 (15)−0.25387 (8)−0.70399 (11)0.0249 (2)
H5A0.5718−0.2800−0.72530.030*
C60.69667 (15)−0.20111 (8)−0.59876 (11)0.0250 (2)
H6A0.5916−0.1903−0.54940.030*
C70.88030 (15)−0.10548 (7)−0.45464 (11)0.0228 (2)
C80.71613 (16)−0.06563 (8)−0.39876 (11)0.0257 (2)
H8A0.5998−0.0789−0.43350.031*
C90.72854 (16)−0.01152 (7)−0.30074 (11)0.0244 (2)
H9A0.84820.0042−0.27530.029*
C100.57985 (15)0.02682 (7)−0.22700 (11)0.0232 (2)
C110.39739 (16)0.00729 (8)−0.25006 (12)0.0269 (3)
H11A0.3655−0.0270−0.32150.032*
C120.26083 (16)0.03728 (8)−0.16994 (12)0.0286 (3)
H12A0.13760.0221−0.18560.034*
C130.30593 (17)0.08902 (8)−0.06791 (11)0.0267 (3)
C140.48422 (18)0.11178 (8)−0.04434 (12)0.0296 (3)
H14A0.51440.14830.02500.036*
C150.61975 (17)0.08026 (8)−0.12423 (12)0.0277 (3)
H15A0.74270.0957−0.10800.033*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0429 (2)0.0418 (2)0.03272 (18)0.01436 (15)0.01185 (14)0.00176 (13)
O10.0232 (4)0.0314 (5)0.0261 (4)−0.0042 (3)0.0043 (3)−0.0055 (3)
O20.0223 (4)0.0345 (5)0.0330 (5)0.0028 (4)−0.0034 (3)−0.0045 (4)
C10.0207 (5)0.0229 (5)0.0216 (5)0.0009 (4)0.0022 (4)0.0022 (4)
C20.0175 (5)0.0265 (6)0.0259 (6)−0.0006 (4)0.0006 (4)0.0022 (5)
C30.0190 (5)0.0280 (6)0.0250 (6)0.0004 (4)0.0053 (4)0.0015 (4)
C40.0236 (5)0.0218 (5)0.0203 (5)0.0008 (4)0.0022 (4)0.0034 (4)
C50.0185 (5)0.0296 (6)0.0265 (6)−0.0049 (4)0.0031 (4)0.0009 (5)
C60.0204 (5)0.0296 (6)0.0250 (6)−0.0003 (4)0.0057 (4)0.0003 (5)
C70.0219 (5)0.0241 (6)0.0226 (5)0.0012 (4)0.0013 (4)0.0033 (4)
C80.0203 (5)0.0312 (6)0.0257 (6)0.0018 (5)−0.0001 (4)−0.0020 (5)
C90.0221 (5)0.0250 (6)0.0262 (6)−0.0004 (4)−0.0004 (4)0.0004 (5)
C100.0243 (5)0.0210 (5)0.0241 (5)0.0009 (4)0.0001 (4)−0.0003 (4)
C110.0265 (6)0.0274 (6)0.0267 (6)0.0013 (5)−0.0025 (5)−0.0048 (5)
C120.0226 (6)0.0319 (6)0.0312 (6)0.0027 (5)−0.0010 (5)−0.0002 (5)
C130.0311 (6)0.0239 (6)0.0251 (6)0.0074 (5)0.0041 (5)0.0028 (5)
C140.0381 (7)0.0244 (6)0.0263 (6)0.0012 (5)−0.0021 (5)−0.0048 (5)
C150.0273 (6)0.0268 (6)0.0290 (6)−0.0029 (5)−0.0031 (5)−0.0029 (5)
Geometric parameters (Å, º) top
Cl—C131.7517 (12)C7—C81.4846 (15)
O1—C41.3541 (14)C8—C91.3348 (16)
O1—H1O0.8400C8—H8A0.9500
O2—C71.2328 (14)C9—C101.4734 (15)
C1—C61.3917 (16)C9—H9A0.9500
C1—C21.4230 (14)C10—C151.3939 (16)
C1—C71.4733 (16)C10—C111.3957 (17)
C2—C31.3770 (16)C11—C121.3971 (16)
C2—H2A0.9500C11—H11A0.9500
C3—C41.3879 (16)C12—C131.3804 (18)
C3—H3A0.9500C12—H12A0.9500
C4—C51.4098 (15)C13—C141.3793 (18)
C5—C61.3811 (17)C14—C151.3984 (17)
C5—H5A0.9500C14—H14A0.9500
C6—H6A0.9500C15—H15A0.9500
C4—O1—H1O109.5C9—C8—H8A119.3
C6—C1—C2117.99 (10)C7—C8—H8A119.3
C6—C1—C7122.56 (10)C8—C9—C10128.11 (11)
C2—C1—C7119.45 (10)C8—C9—H9A115.9
C3—C2—C1121.71 (10)C10—C9—H9A115.9
C3—C2—H2A119.1C15—C10—C11117.45 (10)
C1—C2—H2A119.1C15—C10—C9119.90 (11)
C2—C3—C4119.35 (10)C11—C10—C9122.49 (11)
C2—C3—H3A120.3C10—C11—C12121.18 (11)
C4—C3—H3A120.3C10—C11—H11A119.4
O1—C4—C3117.18 (10)C12—C11—H11A119.4
O1—C4—C5123.03 (10)C13—C12—C11119.66 (11)
C3—C4—C5119.78 (10)C13—C12—H12A120.2
C6—C5—C4120.52 (11)C11—C12—H12A120.2
C6—C5—H5A119.7C14—C13—C12120.79 (11)
C4—C5—H5A119.7C14—C13—Cl120.34 (10)
C5—C6—C1120.59 (10)C12—C13—Cl118.84 (10)
C5—C6—H6A119.7C13—C14—C15118.92 (12)
C1—C6—H6A119.7C13—C14—H14A120.5
O2—C7—C1120.32 (10)C15—C14—H14A120.5
O2—C7—C8119.88 (11)C10—C15—C14121.95 (11)
C1—C7—C8119.80 (10)C10—C15—H15A119.0
C9—C8—C7121.37 (11)C14—C15—H15A119.0
C6—C1—C2—C32.13 (17)C1—C7—C8—C9−178.78 (11)
C7—C1—C2—C3−177.42 (11)C7—C8—C9—C10−173.67 (11)
C1—C2—C3—C4−1.28 (17)C8—C9—C10—C15177.89 (12)
C2—C3—C4—O1178.21 (10)C8—C9—C10—C112.43 (19)
C2—C3—C4—C5−0.86 (17)C15—C10—C11—C12−2.62 (18)
O1—C4—C5—C6−176.85 (11)C9—C10—C11—C12172.94 (12)
C3—C4—C5—C62.17 (18)C10—C11—C12—C131.71 (19)
C4—C5—C6—C1−1.29 (18)C11—C12—C13—C140.26 (19)
C2—C1—C6—C5−0.81 (17)C11—C12—C13—Cl−178.00 (10)
C7—C1—C6—C5178.72 (11)C12—C13—C14—C15−1.18 (19)
C6—C1—C7—O2162.67 (11)Cl—C13—C14—C15177.05 (10)
C2—C1—C7—O2−17.81 (17)C11—C10—C15—C141.68 (18)
C6—C1—C7—C8−17.34 (17)C9—C10—C15—C14−174.00 (11)
C2—C1—C7—C8162.18 (11)C13—C14—C15—C100.19 (19)
O2—C7—C8—C91.20 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O2i0.841.832.6556 (12)167
C6—H6A···O1ii0.952.573.5070 (13)169
C11—H11A···O1ii0.952.553.3382 (15)141
C14—H14A···Cg1iii0.952.793.7090 (14)163
Symmetry codes: (i) x−1/2, −y−1/2, z−1/2; (ii) x−1/2, −y−1/2, z+1/2; (iii) −x+3/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC15H11ClO2
Mr258.69
Crystal system, space groupMonoclinic, P21/n
Temperature (K)200
a, b, c (Å)7.3570 (2), 15.6450 (5), 10.4954 (3)
β (°) 90.518 (3)
V (Å3)1207.97 (6)
Z4
Radiation typeMo Kα
µ (mm−1)0.31
Crystal size (mm)0.51 × 0.45 × 0.36
Data collection
DiffractometerOxford Diffraction Gemini
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.984, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		10126, 4020, 2924
Rint0.022
(sin θ/λ)max (Å−1)0.759
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.115, 1.07
No. of reflections4020
No. of parameters164
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.38, −0.19

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—H1O···O2i0.841.832.6556 (12)167
C6—H6A···O1ii0.952.573.5070 (13)169
C11—H11A···O1ii0.952.553.3382 (15)141
C14—H14A···Cg1iii0.952.793.7090 (14)163
Symmetry codes: (i) x−1/2, −y−1/2, z−1/2; (ii) x−1/2, −y−1/2, z+1/2; (iii) −x+3/2, y+1/2, −z+3/2.
Selected geometric parmeters (Å): Cg···Cg π stacking interactions, Cg1, Cg2 are the centroids of rings C1—C6 and C10—C15 [Symmetry codes: (i) 1-x, 2-y, 1-z; (ii) 1-x, 2-y, 2-z] top
CgI···CgJCg···Cg (Å)CgI Perp (Å)Cgj Perp (Å)Slippage (Å)
Cg1···Cg2i3.7771 (7)3.3144 (5)3.4958 (5)
Cg2···Cg2ii3.6917 (7)-3.3684 (5)-3.3683 (5)1.51 (1)
 

Acknowledgements

BKS thanks the 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.

References

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ISSN: 2056-9890
Volume 67| Part 4| April 2011| Page o756
doi:10.1107/S160053681100701X
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