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

Jasinski, J.P.; Butcher, R.J.; Musthafa Khaleel, V.; Sarojini, B.K.; Yathirajan, H.S.

doi:10.1107/S1600536811008361

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o845

doi:10.1107/S1600536811008361

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

Jerry P. Jasinski,^a ^* Ray J. Butcher,^b V. Musthafa Khaleel,^c B. K. Sarojini ^c and H. S. Yathirajan ^d

^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 π–π stacking interactions [centroid–centroid distance = 3.6571 (8) Å].

Related literature

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

Crystal data

C₁₇H₁₆O₄
M_r = 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 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Oxfordshire, England.]$ ) T_min = 0.065, T_max = 1.000
6676 measured reflections
3014 independent reflections
2336 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.152
S = 1.12
3014 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811008361/kp2312sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811008361/kp2312Isup2.hkl

checkCIF report

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 π—π 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).

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

	Fig. 1. Reaction scheme for (I).
	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.
	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

C₁₇H₁₆O₄	F(000) = 600
M_r = 284.30	D_x = 1.293 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 4075 reflections
a = 14.2315 (2) Å	θ = 5.5–77.1°
b = 8.0292 (1) Å	µ = 0.76 mm⁻¹
c = 13.6027 (2) Å	T = 295 K
β = 110.0531 (14)°	Prism, pale yellow
V = 1460.11 (3) Å³	0.51 × 0.47 × 0.35 mm
Z = 4

Data collection top

Oxford Diffraction Gemini R diffractometer	3014 independent reflections
Radiation source: fine-focus sealed tube	2336 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 10.5081 pixels mm^-1	θ_max = 77.4°, θ_min = 6.4°
ϕ and ω scans	h = −17→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −9→9
T_min = 0.065, T_max = 1.000	l = −15→17
6676 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0968P)² + 0.0366P] where P = (F_o² + 2F_c²)/3
3014 reflections	(Δ/σ)_max < 0.001
193 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₆O₄	V = 1460.11 (3) Å³
M_r = 284.30	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 14.2315 (2) Å	µ = 0.76 mm⁻¹
b = 8.0292 (1) Å	T = 295 K
c = 13.6027 (2) Å	0.51 × 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)
T_min = 0.065, T_max = 1.000	R_int = 0.021
6676 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.12	Δρ_max = 0.18 e Å⁻³
3014 reflections	Δρ_min = −0.18 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	0.88704 (12)	0.7981 (2)	0.17236 (10)	0.0876 (4)
H1A	0.8351	0.7455	0.1617	0.131*
O2	0.76002 (8)	0.62603 (18)	0.21587 (8)	0.0737 (4)
O3	0.63965 (8)	0.32097 (14)	0.68696 (7)	0.0648 (3)
O4	0.47076 (8)	0.18452 (14)	0.59076 (8)	0.0638 (3)
C1	0.90537 (11)	0.71605 (18)	0.34900 (11)	0.0558 (3)
C2	0.94152 (13)	0.7937 (2)	0.27531 (14)	0.0670 (4)
C3	1.03495 (17)	0.8674 (3)	0.3086 (2)	0.0921 (6)
H3A	1.0588	0.9173	0.2601	0.110*
C4	1.09263 (17)	0.8676 (3)	0.4123 (2)	0.1082 (8)
H4A	1.1553	0.9177	0.4338	0.130*
C5	1.05822 (17)	0.7935 (3)	0.4855 (2)	0.1030 (8)
H5A	1.0979	0.7934	0.5559	0.124*
C6	0.96559 (14)	0.7203 (2)	0.45407 (14)	0.0744 (5)
H6A	0.9425	0.6726	0.5038	0.089*
C7	0.80752 (10)	0.63257 (19)	0.31157 (10)	0.0536 (3)
C8	0.76620 (10)	0.55612 (18)	0.38547 (10)	0.0545 (3)
H8A	0.8025	0.5598	0.4568	0.065*
C9	0.67732 (10)	0.48135 (18)	0.35199 (10)	0.0531 (3)
H9A	0.6448	0.4794	0.2799	0.064*
C10	0.62489 (10)	0.40250 (17)	0.41423 (10)	0.0502 (3)
C11	0.66334 (10)	0.40028 (17)	0.52433 (10)	0.0505 (3)
H11A	0.7254	0.4481	0.5593	0.061*
C12	0.61015 (10)	0.32804 (17)	0.58086 (10)	0.0497 (3)
C13	0.51638 (10)	0.25396 (17)	0.52792 (10)	0.0501 (3)
C14	0.47888 (10)	0.25475 (19)	0.41980 (11)	0.0553 (3)
H14A	0.4173	0.2058	0.3845	0.066*
C15	0.53281 (10)	0.3283 (2)	0.36387 (10)	0.0567 (4)
H15A	0.5068	0.3279	0.2911	0.068*
C16	0.73098 (14)	0.3979 (3)	0.74455 (12)	0.0755 (5)
H16A	0.7843	0.3472	0.7271	0.113*
H16B	0.7432	0.3845	0.8180	0.113*
H16C	0.7276	0.5144	0.7278	0.113*
C17	0.37373 (12)	0.1167 (2)	0.54210 (14)	0.0681 (4)
H17A	0.3287	0.2033	0.5056	0.102*
H17B	0.3505	0.0692	0.5944	0.102*
H17C	0.3763	0.0318	0.4934	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1035 (10)	0.1039 (11)	0.0682 (8)	−0.0071 (8)	0.0458 (7)	0.0160 (7)
O2	0.0640 (6)	0.1134 (10)	0.0441 (5)	−0.0038 (6)	0.0193 (5)	0.0099 (5)
O3	0.0718 (6)	0.0810 (7)	0.0380 (5)	−0.0125 (5)	0.0142 (4)	0.0055 (4)
O4	0.0672 (6)	0.0759 (7)	0.0503 (5)	−0.0126 (5)	0.0226 (5)	0.0033 (5)
C1	0.0575 (7)	0.0584 (8)	0.0558 (8)	0.0092 (6)	0.0248 (6)	0.0038 (6)
C2	0.0745 (10)	0.0630 (9)	0.0739 (10)	0.0041 (7)	0.0389 (8)	0.0062 (7)
C3	0.0863 (13)	0.0863 (13)	0.1165 (18)	−0.0127 (10)	0.0514 (13)	0.0123 (12)
C4	0.0760 (13)	0.1022 (16)	0.141 (2)	−0.0257 (11)	0.0305 (14)	0.0055 (15)
C5	0.0775 (12)	0.1164 (18)	0.0948 (15)	−0.0212 (12)	0.0034 (11)	0.0067 (13)
C6	0.0695 (9)	0.0837 (11)	0.0647 (10)	−0.0050 (8)	0.0159 (8)	0.0055 (8)
C7	0.0538 (7)	0.0663 (8)	0.0440 (6)	0.0109 (6)	0.0210 (5)	0.0039 (6)
C8	0.0574 (7)	0.0671 (8)	0.0416 (6)	0.0069 (6)	0.0205 (5)	0.0025 (6)
C9	0.0590 (7)	0.0632 (8)	0.0407 (6)	0.0082 (6)	0.0218 (5)	0.0010 (6)
C10	0.0552 (7)	0.0572 (7)	0.0408 (6)	0.0063 (5)	0.0197 (5)	−0.0008 (5)
C11	0.0523 (7)	0.0570 (7)	0.0417 (6)	−0.0003 (5)	0.0154 (5)	−0.0014 (5)
C12	0.0572 (7)	0.0530 (7)	0.0377 (6)	0.0026 (5)	0.0145 (5)	0.0009 (5)
C13	0.0547 (7)	0.0526 (7)	0.0452 (7)	0.0027 (5)	0.0201 (5)	0.0008 (6)
C14	0.0495 (6)	0.0680 (8)	0.0471 (7)	−0.0012 (6)	0.0147 (5)	−0.0056 (6)
C15	0.0568 (7)	0.0755 (9)	0.0364 (6)	0.0049 (6)	0.0143 (5)	−0.0027 (6)
C16	0.0726 (10)	0.1061 (14)	0.0400 (7)	−0.0133 (9)	0.0094 (6)	−0.0028 (8)
C17	0.0642 (9)	0.0744 (10)	0.0710 (10)	−0.0079 (7)	0.0300 (7)	−0.0029 (8)

Geometric parameters (Å, º) top

O1—C2	1.349 (2)	C8—C9	1.331 (2)
O1—H1A	0.8200	C8—H8A	0.9300
O2—C7	1.2454 (16)	C9—C10	1.4517 (19)
O3—C12	1.3591 (15)	C9—H9A	0.9300
O3—C16	1.4094 (19)	C10—C15	1.388 (2)
O4—C13	1.3578 (16)	C10—C11	1.4073 (17)
O4—C17	1.4193 (19)	C11—C12	1.3784 (19)
C1—C6	1.392 (2)	C11—H11A	0.9300
C1—C2	1.418 (2)	C12—C13	1.4121 (19)
C1—C7	1.470 (2)	C13—C14	1.3820 (18)
C2—C3	1.382 (3)	C14—C15	1.384 (2)
C3—C4	1.367 (3)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.386 (4)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.371 (3)	C16—H16C	0.9600
C5—H5A	0.9300	C17—H17A	0.9600
C6—H6A	0.9300	C17—H17B	0.9600
C7—C8	1.4623 (19)	C17—H17C	0.9600

C2—O1—H1A	109.5	C15—C10—C11	118.47 (12)
C12—O3—C16	117.53 (12)	C15—C10—C9	119.11 (12)
C13—O4—C17	117.57 (11)	C11—C10—C9	122.41 (12)
C6—C1—C2	118.03 (15)	C12—C11—C10	120.76 (12)
C6—C1—C7	122.90 (14)	C12—C11—H11A	119.6
C2—C1—C7	119.06 (13)	C10—C11—H11A	119.6
O1—C2—C3	118.35 (17)	O3—C12—C11	125.54 (12)
O1—C2—C1	121.78 (15)	O3—C12—C13	114.69 (12)
C3—C2—C1	119.88 (18)	C11—C12—C13	119.77 (12)
C4—C3—C2	120.5 (2)	O4—C13—C14	125.33 (13)
C4—C3—H3A	119.7	O4—C13—C12	115.10 (11)
C2—C3—H3A	119.7	C14—C13—C12	119.56 (12)
C3—C4—C5	120.4 (2)	C13—C14—C15	120.15 (13)
C3—C4—H4A	119.8	C13—C14—H14A	119.9
C5—C4—H4A	119.8	C15—C14—H14A	119.9
C6—C5—C4	119.9 (2)	C14—C15—C10	121.29 (12)
C6—C5—H5A	120.1	C14—C15—H15A	119.4
C4—C5—H5A	120.1	C10—C15—H15A	119.4
C5—C6—C1	121.2 (2)	O3—C16—H16A	109.5
C5—C6—H6A	119.4	O3—C16—H16B	109.5
C1—C6—H6A	119.4	H16A—C16—H16B	109.5
O2—C7—C8	119.91 (13)	O3—C16—H16C	109.5
O2—C7—C1	119.43 (13)	H16A—C16—H16C	109.5
C8—C7—C1	120.65 (12)	H16B—C16—H16C	109.5
C9—C8—C7	120.86 (12)	O4—C17—H17A	109.5
C9—C8—H8A	119.6	O4—C17—H17B	109.5
C7—C8—H8A	119.6	H17A—C17—H17B	109.5
C8—C9—C10	127.97 (12)	O4—C17—H17C	109.5
C8—C9—H9A	116.0	H17A—C17—H17C	109.5
C10—C9—H9A	116.0	H17B—C17—H17C	109.5

C6—C1—C2—O1	−178.66 (16)	C8—C9—C10—C11	2.0 (2)
C7—C1—C2—O1	2.4 (2)	C15—C10—C11—C12	−0.9 (2)
C6—C1—C2—C3	1.4 (2)	C9—C10—C11—C12	178.26 (12)
C7—C1—C2—C3	−177.60 (16)	C16—O3—C12—C11	1.9 (2)
O1—C2—C3—C4	179.4 (2)	C16—O3—C12—C13	−177.80 (14)
C1—C2—C3—C4	−0.6 (3)	C10—C11—C12—O3	−179.11 (12)
C2—C3—C4—C5	0.1 (4)	C10—C11—C12—C13	0.6 (2)
C3—C4—C5—C6	−0.4 (4)	C17—O4—C13—C14	−4.4 (2)
C4—C5—C6—C1	1.1 (4)	C17—O4—C13—C12	176.45 (13)
C2—C1—C6—C5	−1.6 (3)	O3—C12—C13—O4	−1.09 (18)
C7—C1—C6—C5	177.29 (19)	C11—C12—C13—O4	179.19 (12)
C6—C1—C7—O2	−176.19 (15)	O3—C12—C13—C14	179.70 (13)
C2—C1—C7—O2	2.7 (2)	C11—C12—C13—C14	0.0 (2)
C6—C1—C7—C8	3.2 (2)	O4—C13—C14—C15	−179.36 (13)
C2—C1—C7—C8	−177.88 (13)	C12—C13—C14—C15	−0.2 (2)
O2—C7—C8—C9	−1.0 (2)	C13—C14—C15—C10	−0.1 (2)
C1—C7—C8—C9	179.55 (13)	C11—C10—C15—C14	0.6 (2)
C7—C8—C9—C10	−178.80 (13)	C9—C10—C15—C14	−178.54 (13)
C8—C9—C10—C15	−178.87 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆O₄
M_r	284.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	14.2315 (2), 8.0292 (1), 13.6027 (2)
β (°)	110.0531 (14)
V (Å³)	1460.11 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.51 × 0.47 × 0.35

Data collection
Diffractometer	Oxford Diffraction Gemini R diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.065, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6676, 3014, 2336
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.152, 1.12
No. of reflections	3014
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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−1/2, −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···CgJ	Cg···Cg (Å)	CgI Perp (Å)	Cgj Perp (Å)	Slippage (Å)
Cg2···Cg2ⁱ	3.6571 (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.

References

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