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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 66| Part 8| August 2010| Page o1952
https://doi.org/10.1107/S1600536810025638

(E)-1-(2-Bromo­phen­yl)-3-(2,5-dimeth­­oxy­phen­yl)prop-2-en-1-one

Jerry P. Jasinski,a* Ray J. Butcher,b K. Veena,c B. Narayanac and H. S. Yathirajand

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, Mangalore University, Mangalagangotri 574 199, India, and dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 9 June 2010; accepted 29 June 2010; online 7 July 2010)

The title compound, C17H15BrO3, is a chalcone with the 2-bromo­phenyl and 2,5-dimeth­oxy­phenyl rings bonded at opposite ends of a propene group. The dihedral angle between the mean planes of the ortho-bromo and ortho,meta-dimeth­oxy-substituted benzene rings is 77.3 (1)°. The dihedral angles between the mean plane of the prop-2-ene-1-one group and the mean planes of the 2-bromo­phenyl and 2,5-dimeth­oxy­phenyl rings are 58.6 (1) and 30.7 (4)°, respectively. Weak C—H⋯O, C—H⋯Br and π–π stacking inter­molecular inter­actions [centroid–centroid distance = 3.650 (2) Å] are present in the structure.

Related literature

For the radical quenching properties of included phenol groups, see: Dhar (1981[Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds. New York: John Wiley.]). For their anti­cancer activity, see Dimmock et al. (1999[Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.]). For related structures, see: Ng et al. (2006[Ng, S.-L., Shettigar, V., Razak, I. A., Fun, H.-K., Patil, P. S. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o1570-o1572.]); Rosli et al. (2006[Rosli, M. M., Patil, P. S., Fun, H.-K., Razak, I. A., Dharmaprakash, S. M. & Karthikeyan, M. S. (2006). Acta Cryst. E62, o1460-o1462.]). 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

  • C17H15BrO3

  • Mr = 347.20

  • Triclinic, [P \overline 1]

  • a = 7.7643 (9) Å

  • b = 9.7006 (11) Å

  • c = 10.2722 (10) Å

  • α = 72.901 (10)°

  • β = 78.487 (9)°

  • γ = 86.359 (9)°

  • V = 724.59 (14) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 3.93 mm−1

  • T = 110 K

  • 0.54 × 0.26 × 0.08 mm
Data collection

  • Oxford Diffraction Xcalibur diffractometer

  • Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.179, Tmax = 0.635

  • 4759 measured reflections

  • 2835 independent reflections

  • 2749 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.146

  • S = 1.05

  • 2835 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 2.51 e Å−3

  • Δρmin = −1.11 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C4—H4⋯Br1i 0.95 2.95 3.834 (4) 155
C3—H3⋯O2ii 0.95 2.62 3.463 (5) 148
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+2, -z.

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 PRO; 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: https://doi.org/10.1107/S1600536810025638/fb2201sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810025638/fb2201Isup2.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. A vast number of naturally occurring chalcones are polyhydroxylated in the aryl rings. The radical quenching properties of the phenol groups present in many chalcones have raised interest in using the compounds or chalcone rich plant extracts as drugs or food preservatives (Dhar, 1981). Chalcones have been reported to possess many useful biological properties, including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, anticancer activities (Dimmock et al., 1999). The crystal structures of closely related chalcones, viz., 1-(4-bromophenyl)-3-(2,5-dimethoxyphenyl)prop-2-en-1-one, (Rosli et al., 2006); 1-(4-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (Ng et al., 2006) have been reported. Hence in continuation with the synthesis and crystal structure determination and also owing to the importance of these flavanoid analogs, this new bromo chalcone C17H15BrO3 has been synthesized (Fig. 1) and its crystal structure is reported.

The title compound, C17H15BrO3, is a chalcone with 2-bromophenyl and 2,5-dimethoxyphenyl rings bonded at opposite ends of a propene group (Fig. 2). The dihedral angle between mean planes of the benzene rings in the ortho-bromo and ortho- meta-diimethoxy substituted rings is 77.3 (1)°. The angles between the mean plane of the prop-2-ene-1-one group (C1/C7/O1/C8) and the mean planes of the benzene rings in the 2-bromophenyl (C1–C6)and 2,5-dimethoxyphenyl rings (C10—C15) are 58.6 (1)° and 30.7 (4)°, respectively. Bond distances and angles are in normal ranges (Allen et al., 1987). While no classical hydrogen bonds are present, weak C3—H3···O2, C4—H4···Br1 (Tab. 1) and π-electron ring - π-electron ring interactions [Cg1···Cg1i = 3.650 (2) Å; i: -x, 1 - y, 1 - z; Cg1 is the centroid of the ring C10—C15] are observed which contribute to the stability of crystal packing (Fig. 3).

Related literature top

For radical quenching properties of included phenol groups, see: Dhar (1981). For their anticancer activity, see Dimmock et al. (1999). For related structureset al987 , see: Ng et al. (2006); Rosli et al. (2006). For standard bond lengths, see: Allen et al. (1987).

Experimental top

A 50% (wt) KOH solution (50 ml) was added to a mixture of 2-bromo acetophenone (0.01 mol, 1.99 g) and 2,5-dimethoxy benzaldehyde (0.01 mol, 1.66 g) in 25 ml of ethanol (Fig. 1). The mixture was stirred for an hour at room temperature and the precipitate was collected by filtration and purified by recrystallization from ethanol. Single crystals (triangular plates with their longest edges 0.3 - 0.5 mm long) were grown from ethyl acetate by slow evaporation method and yield of the compound was 75% (m.p. 355–357 K). Analytical data: Found (Calculated): C %: 58.76 (58.81%); H%: 4.31 (4.35%).

Refinement top

All the hydrogen atoms could have been discerned in the difference electron density map, nevertheless, all the H atoms were constrained in the riding motion approximation. Caryl—H = 0.95 Å, with Uĩso(H) = 1.20Ueq(C). Cmethyl—H = 0.98 Å, with Uiso(H)=1.50Ueq(C).

Structure description 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. A vast number of naturally occurring chalcones are polyhydroxylated in the aryl rings. The radical quenching properties of the phenol groups present in many chalcones have raised interest in using the compounds or chalcone rich plant extracts as drugs or food preservatives (Dhar, 1981). Chalcones have been reported to possess many useful biological properties, including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, anticancer activities (Dimmock et al., 1999). The crystal structures of closely related chalcones, viz., 1-(4-bromophenyl)-3-(2,5-dimethoxyphenyl)prop-2-en-1-one, (Rosli et al., 2006); 1-(4-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (Ng et al., 2006) have been reported. Hence in continuation with the synthesis and crystal structure determination and also owing to the importance of these flavanoid analogs, this new bromo chalcone C17H15BrO3 has been synthesized (Fig. 1) and its crystal structure is reported.

The title compound, C17H15BrO3, is a chalcone with 2-bromophenyl and 2,5-dimethoxyphenyl rings bonded at opposite ends of a propene group (Fig. 2). The dihedral angle between mean planes of the benzene rings in the ortho-bromo and ortho- meta-diimethoxy substituted rings is 77.3 (1)°. The angles between the mean plane of the prop-2-ene-1-one group (C1/C7/O1/C8) and the mean planes of the benzene rings in the 2-bromophenyl (C1–C6)and 2,5-dimethoxyphenyl rings (C10—C15) are 58.6 (1)° and 30.7 (4)°, respectively. Bond distances and angles are in normal ranges (Allen et al., 1987). While no classical hydrogen bonds are present, weak C3—H3···O2, C4—H4···Br1 (Tab. 1) and π-electron ring - π-electron ring interactions [Cg1···Cg1i = 3.650 (2) Å; i: -x, 1 - y, 1 - z; Cg1 is the centroid of the ring C10—C15] are observed which contribute to the stability of crystal packing (Fig. 3).

For radical quenching properties of included phenol groups, see: Dhar (1981). For their anticancer activity, see Dimmock et al. (1999). For related structureset al987 , see: Ng et al. (2006); Rosli et al. (2006). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (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 C17H15BrO3.
[Figure 2] Fig. 2. Title molecule, showing the atom labelling scheme with 50% probability displacement ellipsoids.
[Figure 3] Fig. 3. Packing diagram of the title compound, C17H15BrO3 viewed down the a axis. Dashed lines indicate a weak C—H···O intermolecular hydrogen bond interaction.
(E)-1-(2-Bromophenyl)-3-(2,5-dimethoxyphenyl)prop-2-en-1-one top
Crystal data top
C17H15BrO3Z = 2
Mr = 347.20F(000) = 352
Triclinic, P1Dx = 1.591 Mg m−3
Hall symbol: -P 1Melting point = 355–357 K
a = 7.7643 (9) ÅCu Kα radiation, λ = 1.54184 Å
b = 9.7006 (11) ÅCell parameters from 4418 reflections
c = 10.2722 (10) Åθ = 4.6–73.9°
α = 72.901 (10)°µ = 3.93 mm−1
β = 78.487 (9)°T = 110 K
γ = 86.359 (9)°Triangular plate, colorless
V = 724.59 (14) Å30.54 × 0.26 × 0.08 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer		2835 independent reflections
Radiation source: Enhance (Cu) X-ray Source2749 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
Detector resolution: 10.5081 pixels mm-1θmax = 74.2°, θmin = 4.6°
ω scansh = −9→9
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2007)		k = −12→11
Tmin = 0.179, Tmax = 0.635l = −12→10
4759 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)] = 0.053Hydrogen site location: difference Fourier map
wR(F2) = 0.146H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1005P)2 + 1.9956P]
where P = (Fo2 + 2Fc2)/3
2835 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 2.51 e Å−3
0 restraintsΔρmin = −1.11 e Å−3
58 constraints
Crystal data top
C17H15BrO3γ = 86.359 (9)°
Mr = 347.20V = 724.59 (14) Å3
Triclinic, P1Z = 2
a = 7.7643 (9) ÅCu Kα radiation
b = 9.7006 (11) ŵ = 3.93 mm−1
c = 10.2722 (10) ÅT = 110 K
α = 72.901 (10)°0.54 × 0.26 × 0.08 mm
β = 78.487 (9)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer		2835 independent reflections
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2007)		2749 reflections with I > 2σ(I)
Tmin = 0.179, Tmax = 0.635Rint = 0.037
4759 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.146H-atom parameters constrained
S = 1.05Δρmax = 2.51 e Å−3
2835 reflectionsΔρmin = −1.11 e Å−3
192 parameters
Special details top

Experimental. IR data (KBr) ν cm-1: 2832 cm-1, 2949 cm-1, 2987 cm-1 (C—H al. str), 3453 cm-1 (C—H ar. str) 1680 cm-1 (C=O), 1593 cm-1 (C=C); 1231 cm-1 (C—O—C).

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
Br10.28123 (4)1.19671 (4)−0.00743 (4)0.01849 (18)
O10.1583 (4)1.1329 (3)0.3257 (3)0.0208 (6)
O20.4450 (3)0.5470 (3)0.2755 (3)0.0161 (5)
O30.0011 (4)0.4011 (3)0.7884 (3)0.0177 (5)
C10.4421 (5)1.0666 (3)0.2299 (4)0.0129 (7)
C20.4701 (5)1.1455 (4)0.0894 (4)0.0135 (7)
C30.6379 (5)1.1881 (4)0.0155 (4)0.0160 (7)
H30.65481.2397−0.08020.019*
C40.7801 (5)1.1552 (4)0.0819 (4)0.0194 (8)
H40.89451.18570.03180.023*
C50.7563 (5)1.0772 (4)0.2223 (4)0.0203 (8)
H50.85361.05600.26840.024*
C60.5884 (5)1.0312 (4)0.2936 (4)0.0164 (7)
H60.57290.97430.38780.020*
C70.2612 (5)1.0331 (4)0.3178 (4)0.0138 (7)
C80.2125 (5)0.8849 (4)0.3976 (4)0.0138 (7)
H80.10940.86970.46760.017*
C90.3058 (4)0.7685 (4)0.3774 (3)0.0119 (6)
H90.40860.78480.30700.014*
C100.2606 (4)0.6188 (3)0.4558 (3)0.0103 (6)
C110.3385 (4)0.5059 (4)0.4034 (3)0.0116 (6)
C120.3018 (5)0.3629 (4)0.4806 (4)0.0141 (7)
H120.35350.28650.44540.017*
C130.1900 (5)0.3323 (4)0.6086 (4)0.0149 (7)
H130.16760.23480.66170.018*
C140.1098 (5)0.4435 (4)0.6606 (4)0.0128 (7)
C150.1450 (4)0.5854 (4)0.5843 (3)0.0116 (6)
H150.09030.66110.61930.014*
C160.5285 (5)0.4359 (4)0.2187 (4)0.0184 (7)
H160.60430.47980.12910.028*
H16B0.43880.37720.20570.028*
H16C0.59960.37470.28250.028*
C17−0.0777 (5)0.5153 (4)0.8422 (4)0.0174 (7)
H17−0.15530.47440.93170.026*
H17B−0.14630.57750.77700.026*
H17C0.01440.57210.85480.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0173 (3)0.0181 (3)0.0190 (3)−0.00149 (16)−0.00464 (16)−0.00259 (16)
O10.0213 (13)0.0084 (12)0.0265 (14)0.0010 (10)0.0049 (11)−0.0020 (10)
O20.0204 (13)0.0086 (11)0.0171 (12)−0.0009 (9)0.0051 (10)−0.0060 (9)
O30.0238 (13)0.0101 (12)0.0131 (12)−0.0010 (10)0.0029 (10)0.0021 (9)
C10.0176 (17)0.0045 (14)0.0157 (16)−0.0038 (12)0.0021 (13)−0.0041 (12)
C20.0129 (16)0.0104 (15)0.0158 (16)−0.0017 (12)−0.0002 (13)−0.0032 (13)
C30.0171 (17)0.0103 (15)0.0167 (16)−0.0030 (13)0.0031 (13)−0.0016 (13)
C40.0165 (17)0.0133 (17)0.0248 (19)−0.0052 (13)0.0034 (14)−0.0038 (14)
C50.0188 (18)0.0118 (16)0.030 (2)−0.0014 (13)−0.0069 (15)−0.0042 (15)
C60.0220 (18)0.0076 (15)0.0176 (17)−0.0005 (13)−0.0011 (14)−0.0021 (13)
C70.0173 (17)0.0081 (15)0.0139 (15)−0.0034 (12)0.0015 (13)−0.0023 (12)
C80.0147 (16)0.0076 (15)0.0149 (16)−0.0041 (12)0.0044 (13)−0.0007 (12)
C90.0127 (15)0.0114 (16)0.0106 (15)−0.0036 (12)0.0004 (12)−0.0025 (12)
C100.0115 (15)0.0074 (15)0.0125 (15)−0.0011 (11)−0.0028 (12)−0.0029 (12)
C110.0109 (15)0.0113 (16)0.0124 (15)−0.0002 (12)−0.0010 (12)−0.0040 (12)
C120.0162 (16)0.0078 (15)0.0194 (17)0.0016 (12)−0.0041 (13)−0.0053 (13)
C130.0180 (17)0.0061 (15)0.0178 (17)−0.0027 (12)−0.0046 (13)0.0022 (12)
C140.0145 (16)0.0090 (15)0.0117 (15)−0.0025 (12)−0.0029 (12)0.0028 (12)
C150.0126 (15)0.0089 (15)0.0127 (15)−0.0013 (12)−0.0016 (12)−0.0022 (12)
C160.0189 (17)0.0139 (17)0.0225 (18)0.0011 (13)0.0030 (14)−0.0107 (14)
C170.0183 (17)0.0167 (17)0.0140 (16)−0.0010 (13)0.0019 (13)−0.0025 (13)
Geometric parameters (Å, º) top
Br1—C21.893 (4)C8—H80.9500
O1—C71.227 (4)C9—C101.465 (4)
O2—C111.367 (4)C9—H90.9500
O2—C161.433 (4)C10—C151.402 (5)
O3—C141.375 (4)C10—C111.410 (5)
O3—C171.430 (4)C11—C121.396 (5)
C1—C61.397 (5)C12—C131.384 (5)
C1—C21.401 (5)C12—H120.9500
C1—C71.507 (5)C13—C141.399 (5)
C2—C31.391 (5)C13—H130.9500
C3—C41.383 (6)C14—C151.383 (5)
C3—H30.9500C15—H150.9500
C4—C51.399 (6)C16—H160.9800
C4—H40.9500C16—H16B0.9800
C5—C61.392 (5)C16—H16C0.9800
C5—H50.9500C17—H170.9800
C6—H60.9500C17—H17B0.9800
C7—C81.461 (4)C17—H17C0.9800
C8—C91.348 (5)
C11—O2—C16117.8 (3)C15—C10—C9121.1 (3)
C14—O3—C17115.6 (3)C11—C10—C9119.5 (3)
C6—C1—C2117.9 (3)O2—C11—C12124.4 (3)
C6—C1—C7118.9 (3)O2—C11—C10115.8 (3)
C2—C1—C7122.8 (3)C12—C11—C10119.8 (3)
C3—C2—C1121.2 (3)C13—C12—C11120.0 (3)
C3—C2—Br1117.5 (3)C13—C12—H12120.0
C1—C2—Br1121.3 (3)C11—C12—H12120.0
C4—C3—C2119.8 (3)C12—C13—C14120.7 (3)
C4—C3—H3120.1C12—C13—H13119.6
C2—C3—H3120.1C14—C13—H13119.6
C3—C4—C5120.4 (3)O3—C14—C15124.5 (3)
C3—C4—H4119.8O3—C14—C13115.9 (3)
C5—C4—H4119.8C15—C14—C13119.6 (3)
C6—C5—C4119.1 (4)C14—C15—C10120.6 (3)
C6—C5—H5120.4C14—C15—H15119.7
C4—C5—H5120.4C10—C15—H15119.7
C5—C6—C1121.5 (3)O2—C16—H16109.5
C5—C6—H6119.2O2—C16—H16B109.5
C1—C6—H6119.2H16—C16—H16B109.5
O1—C7—C8120.6 (3)O2—C16—H16C109.5
O1—C7—C1118.9 (3)H16—C16—H16C109.5
C8—C7—C1120.5 (3)H16B—C16—H16C109.5
C9—C8—C7123.6 (3)O3—C17—H17109.5
C9—C8—H8118.2O3—C17—H17B109.5
C7—C8—H8118.2H17—C17—H17B109.5
C8—C9—C10124.9 (3)O3—C17—H17C109.5
C8—C9—H9117.6H17—C17—H17C109.5
C10—C9—H9117.6H17B—C17—H17C109.5
C15—C10—C11119.3 (3)
C6—C1—C2—C3−0.4 (5)C8—C9—C10—C11163.4 (3)
C7—C1—C2—C3172.8 (3)C16—O2—C11—C12−1.9 (5)
C6—C1—C2—Br1179.1 (2)C16—O2—C11—C10179.4 (3)
C7—C1—C2—Br1−7.7 (5)C15—C10—C11—O2177.9 (3)
C1—C2—C3—C4−1.4 (5)C9—C10—C11—O2−4.0 (5)
Br1—C2—C3—C4179.1 (3)C15—C10—C11—C12−0.9 (5)
C2—C3—C4—C51.1 (5)C9—C10—C11—C12177.2 (3)
C3—C4—C5—C61.1 (6)O2—C11—C12—C13−179.1 (3)
C4—C5—C6—C1−3.0 (5)C10—C11—C12—C13−0.4 (5)
C2—C1—C6—C52.6 (5)C11—C12—C13—C141.4 (5)
C7—C1—C6—C5−170.8 (3)C17—O3—C14—C15−0.1 (5)
C6—C1—C7—O1117.6 (4)C17—O3—C14—C13178.8 (3)
C2—C1—C7—O1−55.5 (5)C12—C13—C14—O3179.9 (3)
C6—C1—C7—C8−59.4 (4)C12—C13—C14—C15−1.1 (5)
C2—C1—C7—C8127.4 (4)O3—C14—C15—C10178.7 (3)
O1—C7—C8—C9168.8 (4)C13—C14—C15—C10−0.2 (5)
C1—C7—C8—C9−14.3 (5)C11—C10—C15—C141.2 (5)
C7—C8—C9—C10179.9 (3)C9—C10—C15—C14−176.8 (3)
C8—C9—C10—C15−18.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···Br1i0.952.953.834 (4)155
C3—H3···O2ii0.952.623.463 (5)148
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formulaC17H15BrO3
Mr347.20
Crystal system, space groupTriclinic, P1
Temperature (K)110
a, b, c (Å)7.7643 (9), 9.7006 (11), 10.2722 (10)
α, β, γ (°)72.901 (10), 78.487 (9), 86.359 (9)
V (Å3)724.59 (14)
Z2
Radiation typeCu Kα
µ (mm−1)3.93
Crystal size (mm)0.54 × 0.26 × 0.08
Data collection
DiffractometerOxford Diffraction Xcalibur
Absorption correctionAnalytical
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.179, 0.635
No. of measured, independent and
observed [I > 2σ(I)] reflections		4759, 2835, 2749
Rint0.037
(sin θ/λ)max (Å−1)0.624
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.146, 1.05
No. of reflections2835
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)2.51, −1.11

Computer programs: CrysAlis PRO (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
C4—H4···Br1i0.952.953.834 (4)154.7
C3—H3···O2ii0.952.623.463 (5)147.6
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z.
 

Acknowledgements

KV thanks the UGC for the sanction of a Junior Research Fellowship and for an SAP Chemical grant. HSY thanks the UOM for sabbatical leave. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationDhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds. New York: John Wiley.  Google Scholar
 First citationDimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125–1149.  Web of Science PubMed CAS Google Scholar
 First citationNg, S.-L., Shettigar, V., Razak, I. A., Fun, H.-K., Patil, P. S. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o1570–o1572.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationOxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
 First citationRosli, M. M., Patil, P. S., Fun, H.-K., Razak, I. A., Dharmaprakash, S. M. & Karthikeyan, M. S. (2006). Acta Cryst. E62, o1460–o1462.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 8| August 2010| Page o1952
https://doi.org/10.1107/S1600536810025638
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