(2E)-3-(5-Bromo-2-thien­yl)-1-(4-hydroxy­phen­yl)prop-2-en-1-one

Geometric parameters of the title compound, C₁₃H₉BrO₂S, a chalcone derivative, are in the usual ranges. The C=C double bond is trans configured. The mol­ecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.069 Å). The crystal packing is stabilized by an O—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.031
• wR factor = 0.066
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT415_ALERT_2_B Short Inter D-H..H-X       H2O    ..  H12     ..       2.09 Ang.

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.90
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.85 Ratio
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  O1      ..       3.27 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.903
            Tmax scaled      0.465 Tmin scaled      0.360

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Chalcone derivatives are of interest because of their pharmacological properties (Batt et al., 1993; Sogawa et al., 1994; Arty et al., 2000). They have a wide variety of pharmaceutical activities including anticancer (Modzelewska et al., 2006), anti inflammatory (Won et al., 2005) and antipyretic (De Leon et al., 2003). Chalcones and their heterocyclic derivatives show numerous biological effects (Opletalova & Sedivy, 1999). The cytotoxic, anticancer, chemopreventative and mutagenic properties of a number of chalcones have been reviewed (Dimmock et al., 1999). Chalcones and their analogues are used as potential therapeutic agents in diseases of the cardiovascular system (Opletalova et al., 2003). Photo-cross-linkable polymers having the chalcone moiety act as negative photo resist materials used in a wide variety of applications (Balaji et al., 2003). Chalcones are also used in designing effective second-order non-linear optical materials (Zhao et al., 2000)·The crystal structures of 3-(5-bromo-2-thienyl)-1-(4-methoxyphenyl)-prop-2-en-1-one (Patil et al., 2007), 1-(3-bromo-2-thienyl)-3-(4-methoxyphenyl)prop-2-en-1-one (Harrison et al., 2006), 1-(4-chlorophenyl)-3-(2-thienyl)prop-2-en-1-one (Ng et al., 2006), 1-(3-bromo-2-thienyl)-3-(4,5-dimethoxy-2-nitrophenyl)prop-2-en-1-one (Yathirajan et al., 2006) have been reported. The structure determination of the title compound, (I), was undertaken as a part of our study on chalcones.

Geometric parameters of the title compound are in the usual ranges. The C—C double bond is trans configured. The molecule is essentially planar (r.m.s. deviation for all non-H atoms 0.069 Å). The crystal packing is stabilized by a O—H···O hydrogen bond.

Related literature

For related literature, see: Arty et al. (2000); Balaji et al. (2003); Batt et al. (1993); De Leon et al. (2003); Dimmock et al. (1999); Harrison et al. (2006); Modzelewska et al. (2006); Ng et al. (2006); Opletalova & Sedivy (1999); Opletalova et al. (2003); Patil et al. (2007); Sogawa et al. (1994); Won et al. (2005); Yathirajan et al. (2006); Zhao et al. (2000).

S2. Experimental

5-Bromo-2-thiophene carbaldehyde (1.91 g, 0.01 mol) and 4-hydroxyacetophenone (1.36 g, 0.01 mol) were stirred in ethanol (30 ml) at 298 K. 10 ml of a 10% aqueous NaOH solution was added slowly. The mixture was stirred for 2 h. The resulting precipitate was filtered off, washed with water and dried. The resulting crude product was recrystallized from 1,4-dioxane. Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of the solution of the compound in 1,4-dioxane.

S3. Refinement

All H atoms were found in a difference map, but those bonded to C were geometrically positioned and refined with fixed individual displacement parameters [U_iso(H) = 1.2 U_eq(C)] using a riding model with C—H = 0.95 Å. The hydroxyl H atom was freely refined.

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.

(2E)-3-(5-Bromo-2-thienyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

Crystal data

C13H9BrO2S	F(000) = 1232
Mr = 309.17	Dx = 1.740 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 17692 reflections
a = 13.2344 (8) Å	θ = 3.5–26.7°
b = 11.0471 (8) Å	µ = 3.64 mm^−1
c = 16.1466 (9) Å	T = 173 K
V = 2360.7 (3) Å^3	Block, yellow
Z = 8	0.31 × 0.26 × 0.21 mm

Data collection

Stoe IPDSII two-circle diffractometer	2461 independent reflections
Radiation source: fine-focus sealed tube	2186 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω scans	θmax = 26.6°, θmin = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −16→13
Tmin = 0.398, Tmax = 0.515	k = −13→13
18671 measured reflections	l = −20→20

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.066	w = 1/[σ^2(Fo^2) + (0.0295P)^2 + 2.4425P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2461 reflections	Δρmax = 0.38 e Å^−3
159 parameters	Δρmin = −0.44 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0129 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.864761 (19)	0.01930 (2)	0.897108 (16)	0.02544 (11)
S1	0.79325 (4)	0.23561 (5)	0.78663 (4)	0.02105 (15)
O1	0.80436 (13)	0.61367 (15)	0.57092 (11)	0.0227 (4)
O2	0.32915 (13)	0.69338 (18)	0.52976 (12)	0.0272 (4)
H2O	0.318 (4)	0.761 (4)	0.499 (3)	0.077 (14)*
C1	0.73140 (17)	0.5591 (2)	0.60266 (14)	0.0170 (4)
C2	0.75165 (19)	0.4590 (2)	0.66109 (14)	0.0199 (5)
H2	0.6972	0.4235	0.6908	0.024*
C3	0.84604 (18)	0.41744 (19)	0.67284 (14)	0.0174 (5)
H3	0.8977	0.4551	0.6412	0.021*
C4	0.87774 (17)	0.3218 (2)	0.72835 (14)	0.0178 (5)
C5	0.97564 (18)	0.2833 (2)	0.74100 (14)	0.0191 (5)
H5	1.0323	0.3196	0.7147	0.023*
C6	0.98421 (19)	0.1849 (2)	0.79680 (14)	0.0202 (5)
H6	1.0463	0.1485	0.8126	0.024*
C7	0.89154 (19)	0.1490 (2)	0.82491 (14)	0.0195 (5)
C11	0.62570 (17)	0.5936 (2)	0.58404 (13)	0.0152 (4)
C12	0.60622 (18)	0.6967 (2)	0.53534 (14)	0.0178 (5)
H12	0.6612	0.7430	0.5146	0.021*
C13	0.50800 (17)	0.7317 (2)	0.51712 (13)	0.0169 (4)
H13	0.4962	0.8017	0.4844	0.020*
C14	0.42628 (17)	0.6641 (2)	0.54686 (13)	0.0176 (5)
C15	0.44386 (19)	0.5611 (2)	0.59508 (14)	0.0201 (5)
H15	0.3887	0.5147	0.6153	0.024*
C16	0.54232 (18)	0.5271 (2)	0.61317 (13)	0.0182 (5)
H16	0.5537	0.4571	0.6461	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02815 (16)	0.02015 (15)	0.02802 (15)	0.00418 (10)	0.00377 (10)	0.00766 (10)
S1	0.0174 (3)	0.0206 (3)	0.0251 (3)	0.0030 (2)	0.0005 (2)	0.0052 (2)
O1	0.0151 (8)	0.0228 (9)	0.0303 (9)	−0.0014 (7)	0.0005 (7)	0.0082 (7)
O2	0.0135 (8)	0.0327 (10)	0.0355 (10)	0.0010 (7)	−0.0017 (7)	0.0147 (8)
C1	0.0174 (11)	0.0165 (10)	0.0171 (10)	0.0017 (8)	−0.0010 (9)	−0.0009 (9)
C2	0.0187 (11)	0.0192 (11)	0.0217 (11)	−0.0003 (9)	0.0005 (9)	0.0044 (9)
C3	0.0202 (12)	0.0135 (10)	0.0185 (11)	0.0005 (8)	−0.0018 (9)	−0.0012 (8)
C4	0.0171 (11)	0.0172 (11)	0.0191 (11)	0.0000 (8)	−0.0015 (9)	−0.0016 (8)
C5	0.0183 (11)	0.0178 (11)	0.0211 (11)	−0.0015 (9)	−0.0020 (9)	−0.0003 (9)
C6	0.0202 (11)	0.0204 (11)	0.0200 (11)	0.0044 (9)	−0.0034 (9)	−0.0002 (9)
C7	0.0243 (12)	0.0154 (10)	0.0189 (11)	0.0040 (9)	−0.0019 (9)	0.0005 (9)
C11	0.0156 (11)	0.0156 (10)	0.0144 (10)	0.0011 (8)	−0.0009 (8)	0.0003 (8)
C12	0.0167 (11)	0.0168 (10)	0.0200 (11)	−0.0018 (9)	0.0023 (9)	0.0021 (9)
C13	0.0168 (11)	0.0173 (10)	0.0167 (11)	0.0010 (8)	0.0003 (8)	0.0044 (8)
C14	0.0147 (11)	0.0209 (11)	0.0171 (10)	0.0009 (8)	−0.0003 (8)	0.0011 (9)
C15	0.0172 (11)	0.0212 (11)	0.0218 (11)	−0.0034 (9)	0.0019 (9)	0.0056 (9)
C16	0.0193 (11)	0.0169 (11)	0.0185 (11)	0.0003 (9)	−0.0007 (9)	0.0036 (9)

Geometric parameters (Å, º)

Br1—C7	1.881 (2)	C5—H5	0.9500
S1—C7	1.729 (2)	C6—C7	1.366 (4)
S1—C4	1.744 (2)	C6—H6	0.9500
O1—C1	1.249 (3)	C11—C16	1.407 (3)
O2—C14	1.354 (3)	C11—C12	1.408 (3)
O2—H2O	0.92 (5)	C12—C13	1.388 (3)
C1—C2	1.478 (3)	C12—H12	0.9500
C1—C11	1.481 (3)	C13—C14	1.399 (3)
C2—C3	1.344 (3)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.398 (3)
C3—C4	1.448 (3)	C15—C16	1.387 (3)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.379 (3)	C16—H16	0.9500
C5—C6	1.417 (3)
C7—S1—C4	90.71 (11)	C6—C7—Br1	126.56 (18)
C14—O2—H2O	118 (3)	S1—C7—Br1	120.08 (14)
O1—C1—C2	118.9 (2)	C16—C11—C12	117.8 (2)
O1—C1—C11	121.5 (2)	C16—C11—C1	122.6 (2)
C2—C1—C11	119.6 (2)	C12—C11—C1	119.6 (2)
C3—C2—C1	120.9 (2)	C13—C12—C11	121.0 (2)
C3—C2—H2	119.5	C13—C12—H12	119.5
C1—C2—H2	119.5	C11—C12—H12	119.5
C2—C3—C4	127.3 (2)	C12—C13—C14	120.2 (2)
C2—C3—H3	116.4	C12—C13—H13	119.9
C4—C3—H3	116.4	C14—C13—H13	119.9
C5—C4—C3	126.1 (2)	O2—C14—C15	117.8 (2)
C5—C4—S1	110.76 (17)	O2—C14—C13	122.4 (2)
C3—C4—S1	123.13 (18)	C15—C14—C13	119.8 (2)
C4—C5—C6	113.9 (2)	C16—C15—C14	119.6 (2)
C4—C5—H5	123.0	C16—C15—H15	120.2
C6—C5—H5	123.0	C14—C15—H15	120.2
C7—C6—C5	111.2 (2)	C15—C16—C11	121.7 (2)
C7—C6—H6	124.4	C15—C16—H16	119.2
C5—C6—H6	124.4	C11—C16—H16	119.2
C6—C7—S1	113.35 (17)
O1—C1—C2—C3	−7.7 (3)	O1—C1—C11—C16	174.3 (2)
C11—C1—C2—C3	173.2 (2)	C2—C1—C11—C16	−6.6 (3)
C1—C2—C3—C4	179.1 (2)	O1—C1—C11—C12	−5.7 (3)
C2—C3—C4—C5	−177.9 (2)	C2—C1—C11—C12	173.4 (2)
C2—C3—C4—S1	4.2 (3)	C16—C11—C12—C13	0.3 (3)
C7—S1—C4—C5	−0.92 (18)	C1—C11—C12—C13	−179.7 (2)
C7—S1—C4—C3	177.3 (2)	C11—C12—C13—C14	−0.3 (3)
C3—C4—C5—C6	−177.9 (2)	C12—C13—C14—O2	−179.0 (2)
S1—C4—C5—C6	0.3 (3)	C12—C13—C14—C15	0.0 (3)
C4—C5—C6—C7	0.8 (3)	O2—C14—C15—C16	179.2 (2)
C5—C6—C7—S1	−1.5 (3)	C13—C14—C15—C16	0.1 (3)
C5—C6—C7—Br1	177.93 (17)	C14—C15—C16—C11	−0.1 (4)
C4—S1—C7—C6	1.41 (19)	C12—C11—C16—C15	−0.1 (3)
C4—S1—C7—Br1	−178.06 (14)	C1—C11—C16—C15	179.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1^i	0.92 (5)	1.79 (5)	2.701 (3)	173 (5)

Symmetry code: (i) x−1/2, −y+3/2, −z+1.