(2E)-1-(4-Bromo­phen­yl)-3-(4-fluoro­phen­yl)prop-2-en-1-one

Dutkiewicz, G.; Veena, K.; Narayana, B.; Yathirajan, H.S.; Kubicki, M.

doi:10.1107/S1600536810015485

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Pages o1243-o1244

https://doi.org/10.1107/S1600536810015485

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(2E)-1-(4-Bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one

Grzegorz Dutkiewicz,^a K. Veena,^b B. Narayana,^b H. S. Yathirajan ^c and Maciej Kubicki ^a ^*

^aDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: mkubicki@amu.edu.pl

(Received 16 April 2010; accepted 27 April 2010; online 30 April 2010)

The title compound, C₁₅H₁₀BrFO, is isostructural with (2E)-1-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one [Qiu et al. (2006 ). Acta Cryst. E62, o3525–o3526], but the structures of other dihalogen analogues, without fluorine, are different, although they are also isostructural within the series. The molecule is approximately flat, the dihedral angle between the ring planes being 8.49 (13)°. In the crystal structure, intermolecular C—H⋯O, C—H⋯F and C—H⋯Br hydrogen bonds link molecules into V-shaped ribbons running parallel to [101] and stacked with an interplanar distance of approximately 3.53 Å (centroid–vcentroid distance = 3.857 Å)..

Related literature

For general background to chalcones, see: Dhar (1981 ); Goto et al. (1991 ); Uchida et al. (1998 ); Indira et al. (2002 ); Sarojini et al. (2006 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For the isostructurality index, see: Kálmán et al. (1991 ). For related halogen derivatives, see: Ng, Razak, et al. (2006 ); Ng, Shettigar et al. (2006 ); Qiu et al. (2006); Wang et al. (2005 ); Yang et al. (2006 ).

Experimental

Crystal data

C₁₅H₁₀BrFO
M_r = 305.14
Monoclinic, P 2₁ /n
a = 4.0060 (5) Å
b = 23.1253 (12) Å
c = 13.4933 (9) Å
β = 96.344 (6)°
V = 1242.36 (19) Å³
Z = 4
Cu Kα radiation
μ = 4.49 mm⁻¹
T = 295 K
0.4 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction SuperNova (single source at offset) Atlas diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.386, T_max = 1.000
4548 measured reflections
2435 independent reflections
2299 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.116
S = 1.12
2435 reflections
203 parameters
All H-atom parameters refined
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O9ⁱ	0.98 (3)	2.62 (3)	3.512 (3)	151 (2)
C3—H3⋯O9ⁱ	0.99 (3)	2.41 (3)	3.358 (3)	160 (2)
C15—H15⋯Br1ⁱⁱ	1.02 (3)	2.92 (3)	3.845 (2)	151 (2)
C12—H12⋯F1ⁱⁱⁱ	1.00 (3)	2.55 (3)	3.351 (3)	137 (2)
Symmetry codes: (i) -x, -y, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z-1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: XP (Siemens, 1989 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810015485/rz2439sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015485/rz2439Isup2.hkl

checkCIF report

Comment top

Chalcones or 1,3-diaryl-2-propen-1-ones (Ar—CH=CH—CO—Ar) are one of the major classes of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based foodstuff. These compounds have been recently subjects of great interest for their interesting pharmacological activities (Dhar, 1981). They are finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006). Among several organic compounds reported which have NLO properties, chalcones derivatives are recognized material because of their excellent blue light transmittance and good crystallization ability (Goto et al., 1991; Uchida et al. (1998); Indira et al., 2002).

In the Cambridge Structural Database (Allen, 2002; Version 5.31, Nov. 2009) there are structural data for a series of the (2E)-1-(4-X)-3-(4-Y)prop-2-en-1-ones (X, Y - halogen). Those which have chloro- and/or bromo-substituents (X = Y = Cl: Wang et al., 2005; X = Cl, Y = Br: Ng, Razak et al., 2006; X = Y = Br: Ng, Shettigar et al., 2006, and X = Br, Y = Cl: Yang et al., 2006) are isostructural (P2₁/c space group), and their crystal structure is similarly organized by π–π and halogen–halogen interactions. The only fluoro-derivative in the CCDC, (E)-1-(4-chlorophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (i.e. X = Cl, Y = F, Qiu et al., 2006) does not fit into this scheme; although it crystallizes in the same space group, however in different setting (P2₁/n), both the molecular geometry and the crystal packing are different. Here we present the crystal structure of another fluoro-derivative, (2E)-1-(4-bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (I, Scheme 1), which turned out to be isostructural with the latter example.

The crystal structure of I is isostructural with the F-Cl analogue; both compounds crystallize in the P2₁/n space group and their crystal packings are almost identical. The isostructurality index (Kálmán et al., 1991), which measures the differences in the positions of the atoms in the respective unit cell, is 0.9%, which is very close to the ideal value of 0.

The molecule of I is approximately planar (Fig. 1), the dihedral angle between the planes of the aromatic rings is 8.49 (13)°, and the central C=C-C=O fragment, is inclined by about 10° with respect to both rings. This conformation is of course similar to the F-Cl analogue, where the terminal planes make a angle of 9.1°, but is essentially different from the other group of halogeno- derivatives, where the conformation is much more folded, the dihedral angles being around 45°. It might be noted that there is also another difference: in the latter structures the angles between the central plane and the ring planes approximately sum up to the value of the angle between terminal planes. That means that in these cases the rings are twisted in opposite directions with respect to the central plane, while in I they are twisted in the same direction.

In the crystal structure, the molecules are connected by means of weak C—H···O hydrogen bonds into centrosymmetric dimers, and these dimers are connected by weak C—H···F interactions into two-molecule wide ribbons (Fig. 2). Neighbouring ribbons, inclined by an angle of approximately 58°, are connected by C—H···Br contacts (Fig. 3). In spite of the compounds without fluorine, there are no short halogen···halogen contacts. This might be regarded as another evidence of the essential difference between fluorine and other halogen atoms.

Additionally, thanks to the short unit cell parameter of 4.0060 (5)Å, the planes of molecules are stacked one onto another with an interplanar distance of about 3.53Å.

Related literature top

For general background to chalcones, see: Dhar (1981); Goto et al. (1991); Uchida et al. (1998); Indira et al. (2002); Sarojini et al. (2006). For reference structural data, see: Allen (2002). For the isostructurality index, see: Kálmán et al. (1991). For related halogen derivatives, see: Ng, Razak, et al. (2006); Ng, Shettigar et al. (2006); Qiu et al. (2006); Wang et al. (2005); Yang et al. (2006).

Experimental top

10 ml of 10% KOH was added to a mixture of 4-bromoacetophenone (0.01 mol) and p-fluorobenzaldehyde (0.01 mol) in 40 mL of ethyl alcohol. The reaction mixture was then kept under constant stirring. The solid product was filtered and recrystallized from an ethyl acetate solution at room temperature. C₁₅H₁₀BrFO, calculated: C 59.04% 3.30%, found: C 58.98, H 3.25. M.P.: 362-366 K.

Structure description top

Additionally, thanks to the short unit cell parameter of 4.0060 (5)Å, the planes of molecules are stacked one onto another with an interplanar distance of about 3.53Å.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Siemens, 1989); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Perspective view of the title compound with labelling scheme and displacement ellipsoids drawn at 50% probability level. Hydrogen atoms are depicted as spheres with arbitrary radii.
	Fig. 2. A fragment of the hydrogen bonded ribbon as seen approximately along the [100] direction. The hydrogen-bonding interactions are shown as dashed lines. Symmetry codes: (i) x, y, z; (ii) -x, -y, 1-z; (iii) 1-x, -y, 2-z; (iv) 1+x, y, 1+z.
	Fig. 3. The crystal packing of the title compound showing neighbouring ribbons connected by weak C-H···Br contacts. Hydrogen-bonding interactions are shown as dashed lines.

(2E)-1-(4-Bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₀BrFO	F(000) = 608
M_r = 305.14	D_x = 1.631 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 4020 reflections
a = 4.0060 (5) Å	θ = 3.3–75.1°
b = 23.1253 (12) Å	µ = 4.49 mm⁻¹
c = 13.4933 (9) Å	T = 295 K
β = 96.344 (6)°	Prism, colourless
V = 1242.36 (19) Å³	0.4 × 0.2 × 0.1 mm
Z = 4

Data collection top

Oxford Diffraction SuperNova (single source at offset) Atlas diffractometer	2435 independent reflections
Radiation source: Nova (Cu) X-ray Source	2299 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.018
Detector resolution: 5.2679 pixels mm^-1	θ_max = 75.2°, θ_min = 3.8°
ω–scan	h = −3→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −28→27
T_min = 0.386, T_max = 1.000	l = −16→14
4548 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	All H-atom parameters refined
S = 1.12	w = 1/[σ²(F_o²) + (0.0695P)² + 0.5227P] where P = (F_o² + 2F_c²)/3
2435 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₅H₁₀BrFO	V = 1242.36 (19) Å³
M_r = 305.14	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 4.0060 (5) Å	µ = 4.49 mm⁻¹
b = 23.1253 (12) Å	T = 295 K
c = 13.4933 (9) Å	0.4 × 0.2 × 0.1 mm
β = 96.344 (6)°

Data collection top

Oxford Diffraction SuperNova (single source at offset) Atlas diffractometer	2435 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2299 reflections with I > 2σ(I)
T_min = 0.386, T_max = 1.000	R_int = 0.018
4548 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.116	All H-atom parameters refined
S = 1.12	Δρ_max = 0.73 e Å⁻³
2435 reflections	Δρ_min = −0.50 e Å⁻³
203 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Br1	0.64900 (8)	0.251119 (13)	0.06664 (2)	0.06378 (18)
F1	0.8178 (6)	0.08073 (9)	0.99300 (12)	0.0843 (6)
C1	0.7067 (7)	0.07919 (13)	0.89344 (19)	0.0548 (6)
C2	0.5320 (8)	0.03177 (13)	0.85733 (18)	0.0544 (6)
H2	0.507 (9)	−0.0022 (15)	0.902 (3)	0.073 (10)*
C3	0.4195 (7)	0.03031 (11)	0.75622 (18)	0.0482 (6)
H3	0.297 (9)	−0.0027 (13)	0.722 (3)	0.073 (10)*
C4	0.4894 (6)	0.07548 (10)	0.69363 (16)	0.0400 (5)
C5	0.6687 (7)	0.12313 (12)	0.73467 (19)	0.0489 (6)
H5	0.725 (10)	0.1543 (15)	0.699 (3)	0.078 (10)*
C6	0.7766 (8)	0.12519 (14)	0.8363 (2)	0.0572 (7)
H6	0.914 (9)	0.1585 (15)	0.870 (3)	0.078 (11)*
C7	0.3685 (6)	0.07087 (10)	0.58732 (16)	0.0417 (5)
H7	0.190 (7)	0.0422 (13)	0.571 (2)	0.051 (8)*
C8	0.4515 (6)	0.10426 (10)	0.51437 (17)	0.0423 (5)
H8	0.627 (7)	0.1331 (13)	0.525 (2)	0.053 (8)*
O9	0.1120 (5)	0.05436 (8)	0.38882 (13)	0.0589 (5)
C9	0.3051 (6)	0.09403 (10)	0.41020 (17)	0.0401 (5)
C10	0.3943 (5)	0.13412 (10)	0.32965 (16)	0.0368 (5)
C11	0.2928 (6)	0.11865 (11)	0.23070 (17)	0.0426 (5)
H11	0.184 (8)	0.0847 (13)	0.217 (2)	0.060 (8)*
C12	0.3662 (6)	0.15324 (11)	0.15256 (17)	0.0462 (5)
H12	0.294 (7)	0.1403 (12)	0.083 (2)	0.054 (8)*
C13	0.5401 (6)	0.20384 (11)	0.17354 (17)	0.0427 (5)
C14	0.6406 (6)	0.22126 (11)	0.27017 (19)	0.0461 (5)
H14	0.716 (12)	0.2556 (13)	0.277 (3)	0.075 (13)*
C15	0.5676 (6)	0.18557 (10)	0.34762 (17)	0.0436 (5)
H15	0.646 (8)	0.1983 (13)	0.419 (2)	0.059 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0534 (3)	0.0764 (3)	0.0619 (3)	0.00176 (12)	0.00788 (16)	0.03331 (14)
F1	0.1142 (16)	0.1010 (15)	0.0343 (8)	−0.0239 (12)	−0.0074 (9)	−0.0034 (8)
C1	0.0614 (16)	0.0684 (16)	0.0341 (12)	−0.0027 (13)	0.0027 (10)	−0.0040 (11)
C2	0.0702 (17)	0.0569 (15)	0.0362 (12)	−0.0062 (13)	0.0067 (11)	0.0058 (11)
C3	0.0589 (14)	0.0470 (13)	0.0386 (11)	−0.0078 (11)	0.0049 (10)	0.0009 (10)
C4	0.0422 (12)	0.0436 (11)	0.0344 (10)	0.0012 (9)	0.0052 (8)	0.0013 (9)
C5	0.0573 (15)	0.0465 (13)	0.0429 (12)	−0.0077 (11)	0.0059 (10)	0.0020 (10)
C6	0.0648 (17)	0.0624 (16)	0.0437 (13)	−0.0148 (13)	0.0031 (12)	−0.0074 (12)
C7	0.0449 (12)	0.0435 (11)	0.0365 (11)	−0.0004 (9)	0.0036 (9)	−0.0011 (9)
C8	0.0441 (12)	0.0455 (12)	0.0368 (11)	−0.0024 (10)	0.0021 (9)	−0.0005 (9)
O9	0.0744 (13)	0.0577 (11)	0.0428 (9)	−0.0259 (10)	−0.0017 (8)	0.0021 (8)
C9	0.0440 (12)	0.0411 (11)	0.0351 (10)	−0.0001 (9)	0.0038 (8)	−0.0003 (9)
C10	0.0357 (11)	0.0393 (11)	0.0349 (10)	0.0039 (8)	0.0019 (8)	−0.0005 (8)
C11	0.0483 (13)	0.0418 (12)	0.0366 (11)	−0.0031 (9)	0.0000 (9)	−0.0012 (9)
C12	0.0499 (13)	0.0536 (13)	0.0337 (11)	0.0025 (10)	−0.0014 (9)	0.0032 (9)
C13	0.0360 (11)	0.0487 (12)	0.0432 (11)	0.0063 (9)	0.0037 (8)	0.0111 (9)
C14	0.0435 (12)	0.0430 (13)	0.0513 (13)	−0.0063 (10)	0.0027 (10)	0.0005 (10)
C15	0.0474 (12)	0.0454 (12)	0.0372 (11)	−0.0032 (10)	0.0008 (9)	−0.0032 (9)

Geometric parameters (Å, º) top

Br1—C13	1.899 (2)	C8—C9	1.481 (3)
F1—C1	1.368 (3)	C8—H8	0.97 (3)
C1—C6	1.361 (4)	O9—C9	1.214 (3)
C1—C2	1.362 (4)	C9—C10	1.501 (3)
C2—C3	1.389 (3)	C10—C15	1.385 (3)
C2—H2	1.00 (3)	C10—C11	1.399 (3)
C3—C4	1.391 (3)	C11—C12	1.381 (3)
C3—H3	0.99 (3)	C11—H11	0.91 (3)
C4—C5	1.396 (3)	C12—C13	1.375 (4)
C4—C7	1.466 (3)	C12—H12	1.00 (3)
C5—C6	1.392 (4)	C13—C14	1.381 (3)
C5—H5	0.91 (4)	C14—C15	1.388 (3)
C6—H6	1.02 (4)	C14—H14	0.85 (3)
C7—C8	1.322 (3)	C15—H15	1.02 (3)
C7—H7	0.98 (3)

C6—C1—C2	123.8 (2)	C9—C8—H8	117.1 (18)
C6—C1—F1	118.1 (3)	O9—C9—C8	121.4 (2)
C2—C1—F1	118.1 (3)	O9—C9—C10	119.4 (2)
C1—C2—C3	118.0 (2)	C8—C9—C10	119.2 (2)
C1—C2—H2	119.8 (19)	C15—C10—C11	118.3 (2)
C3—C2—H2	122.0 (19)	C15—C10—C9	123.94 (19)
C2—C3—C4	120.9 (2)	C11—C10—C9	117.8 (2)
C2—C3—H3	124 (2)	C12—C11—C10	121.1 (2)
C4—C3—H3	115 (2)	C12—C11—H11	119 (2)
C3—C4—C5	118.8 (2)	C10—C11—H11	120 (2)
C3—C4—C7	118.2 (2)	C13—C12—C11	118.8 (2)
C5—C4—C7	123.0 (2)	C13—C12—H12	122.5 (17)
C6—C5—C4	120.5 (2)	C11—C12—H12	118.7 (17)
C6—C5—H5	115 (2)	C12—C13—C14	122.0 (2)
C4—C5—H5	124 (2)	C12—C13—Br1	119.16 (18)
C1—C6—C5	118.1 (3)	C14—C13—Br1	118.80 (19)
C1—C6—H6	118 (2)	C13—C14—C15	118.3 (2)
C5—C6—H6	124 (2)	C13—C14—H14	116 (3)
C8—C7—C4	127.1 (2)	C15—C14—H14	125 (3)
C8—C7—H7	118.0 (16)	C10—C15—C14	121.5 (2)
C4—C7—H7	114.6 (16)	C10—C15—H15	120.5 (17)
C7—C8—C9	120.5 (2)	C14—C15—H15	118.0 (17)
C7—C8—H8	122.0 (18)

C6—C1—C2—C3	0.1 (5)	O9—C9—C10—C15	169.3 (2)
F1—C1—C2—C3	−180.0 (3)	C8—C9—C10—C15	−9.8 (3)
C1—C2—C3—C4	1.2 (4)	O9—C9—C10—C11	−10.0 (3)
C2—C3—C4—C5	−1.5 (4)	C8—C9—C10—C11	170.8 (2)
C2—C3—C4—C7	179.0 (2)	C15—C10—C11—C12	0.7 (4)
C3—C4—C5—C6	0.3 (4)	C9—C10—C11—C12	−179.8 (2)
C7—C4—C5—C6	179.9 (3)	C10—C11—C12—C13	−0.4 (4)
C2—C1—C6—C5	−1.3 (5)	C11—C12—C13—C14	−0.6 (4)
F1—C1—C6—C5	178.9 (3)	C11—C12—C13—Br1	178.96 (18)
C4—C5—C6—C1	1.0 (5)	C12—C13—C14—C15	1.3 (4)
C3—C4—C7—C8	−168.8 (3)	Br1—C13—C14—C15	−178.27 (18)
C5—C4—C7—C8	11.6 (4)	C11—C10—C15—C14	0.0 (4)
C4—C7—C8—C9	−179.7 (2)	C9—C10—C15—C14	−179.4 (2)
C7—C8—C9—O9	−1.5 (4)	C13—C14—C15—C10	−1.0 (4)
C7—C8—C9—C10	177.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O9ⁱ	0.98 (3)	2.62 (3)	3.512 (3)	151 (2)
C3—H3···O9ⁱ	0.99 (3)	2.41 (3)	3.358 (3)	160 (2)
C15—H15···Br1ⁱⁱ	1.02 (3)	2.92 (3)	3.845 (2)	151 (2)
C12—H12···F1ⁱⁱⁱ	1.00 (3)	2.55 (3)	3.351 (3)	137 (2)

Symmetry codes: (i) −x, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrFO
M_r	305.14
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	4.0060 (5), 23.1253 (12), 13.4933 (9)
β (°)	96.344 (6)
V (Å³)	1242.36 (19)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.49
Crystal size (mm)	0.4 × 0.2 × 0.1

Data collection
Diffractometer	Oxford Diffraction SuperNova (single source at offset) Atlas
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.386, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4548, 2435, 2299
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.116, 1.12
No. of reflections	2435
No. of parameters	203
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.50

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), XP (Siemens, 1989).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O9ⁱ	0.98 (3)	2.62 (3)	3.512 (3)	151 (2)
C3—H3···O9ⁱ	0.99 (3)	2.41 (3)	3.358 (3)	160 (2)
C15—H15···Br1ⁱⁱ	1.02 (3)	2.92 (3)	3.845 (2)	151 (2)
C12—H12···F1ⁱⁱⁱ	1.00 (3)	2.55 (3)	3.351 (3)	137 (2)

Symmetry codes: (i) −x, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2; (iii) x−1, y, z−1.

Acknowledgements

BN thanks the UGC, New Delhi, Government of India, for the purchase of chemicals through the SAP-DRS-Phase 1 programme.

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