(2E)-3-(3-Bromo­phen­yl)-1-(4-chloro­phen­yl)prop-2-en-1-one: a non-merohedral twin

Li, H.; Kamath, K.P.; Narayana, B.; Yathirajan, H.S.; Harrison, W.T.A.

doi:10.1107/S1600536809027615

organic compounds

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doi:10.1107/S1600536809027615

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(2E)-3-(3-Bromophenyl)-1-(4-chlorophenyl)prop-2-en-1-one: a non-merohedral twin

Hongqi Li,^a ^* K. Prakash Kamath,^b B. Narayana,^c H. S. Yathirajan ^d and William T. A. Harrison ^e

^aKey Laboratory of Science & Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering & Biotechnology, Donghua University, Shanghai 201620, People's Republic of China, ^bDepartment of Studies in Physics, Mangalore University, Mangalagangotri 574 199, India, ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^eDepartment of Chemistry, University of Aberdeen, Aberdeen AB24 3UE, Scotland
^*Correspondence e-mail: hongqili@dhu.edu.cn

(Received 21 April 2009; accepted 14 July 2009; online 18 July 2009)

In the title compound, C₁₅H₁₀BrClO, the molecule adopts an E configuration with respect to the C=C double bond and the dihedral angle between the aromatic ring planes is 3.98 (16)°. In the crystal, inversion dimers linked by pairs of C—H⋯O bonds are seen and weak π–π stacking [centroid–centroid separation = 3.8776 (19) Å] may further consolidate the structure. The crystal studied was a non-merohedral twin with a ratio of the twin components of 0.9093 (13):0.0907 (13). The twin operation is a twofold rotation around c*.

Related literature

For related structures and background to bromo- and chloro-substituted chalcones, see: Yathirajan et al. (2006 ), Sarojini et al. (2007 ).

Experimental

Crystal data

C₁₅H₁₀BrClO
M_r = 321.59
Monoclinic, P 2₁ /n
a = 14.7421 (10) Å
b = 6.1024 (4) Å
c = 15.1874 (10) Å
β = 103.905 (2)°
V = 1326.25 (15) Å³
Z = 4
Mo Kα radiation
μ = 3.28 mm⁻¹
T = 296 K
0.59 × 0.58 × 0.41 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.248, T_max = 0.346 (expected range = 0.186–0.260)
2609 measured reflections
2609 independent reflections
2273 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.120
S = 1.05
2609 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1ⁱ	0.93	2.53	3.328 (4)	144
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809027615/kj2127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027615/kj2127Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of bromo- and chloro-substituted chalcones (Yathirajan, et al., 2006; Sarojini, et al., 2007), we now present the synthesis and structure of the title compound (Fig. 1).

The molecule adopts an E configuration with respect to the C=C double bond of the propenone unit. The two benzene rings are approximately coplanar, with a dihedral angle of 3.98 (16)° between their mean planes. The bromine atom is displaced from the C1–C6 mean plane by -0.051 (1)Å and the chlorine atom is displaced from C10–C15 by 0.028 (1) Å. In the crystal, inversion dimers linked by pairs of weak C—H···O interactions (Table 1, Fig. 2) occur.

Related literature top

For related structures and background to bromo- and chloro-substituted chalcones, see: Yathirajan et al. (2006), Sarojini et al. (2007).

Experimental top

50% KOH was added to a solution of 4-chloroacetophenone (1.54 g, 0.01 mol) and 3-bromobenzaldehyde (1.86 g, 0.01 mol) in 25 ml of ethanol at 273 K. The mixture was stirred for an hour at room temperature and then poured onto crushed ice. A yellow precipitate was collected by filtration and purified by recrystallization from ethanol. Yellow blocks of the title compound were grown from a mixture of acetone and toluene (1:1) by slow evaporation. Yield of the compound was 80%. Analysis: found (calculated): C%, 55.94 (56.02); H%, 3.10 (3.13).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level and H atoms shown as spheres of arbitrary radius.
	Fig. 2. An inversion dimer in the crystal of the title compound linked by two C—H···O bonds (double dashed lines). Symmetry code: (i) 1–x, –y, 1–z.

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

Crystal data top

C₁₅H₁₀BrClO	F(000) = 640
M_r = 321.59	D_x = 1.611 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7751 reflections
a = 14.7421 (10) Å	θ = 2.2–28.0°
b = 6.1024 (4) Å	µ = 3.28 mm⁻¹
c = 15.1874 (10) Å	T = 296 K
β = 103.905 (2)°	Block, yellow
V = 1326.25 (15) Å³	0.59 × 0.58 × 0.41 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2609 independent reflections
Radiation source: fine-focus sealed tube	2273 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→18
T_min = 0.248, T_max = 0.346	k = −7→7
2609 measured reflections	l = −7→18

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0724P)² + 0.8199P] where P = (F_o² + 2F_c²)/3
2609 reflections	(Δ/σ)_max < 0.001
164 parameters	Δρ_max = 0.88 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₅H₁₀BrClO	V = 1326.25 (15) Å³
M_r = 321.59	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.7421 (10) Å	µ = 3.28 mm⁻¹
b = 6.1024 (4) Å	T = 296 K
c = 15.1874 (10) Å	0.59 × 0.58 × 0.41 mm
β = 103.905 (2)°

Data collection top

Bruker SMART CCD diffractometer	2609 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2273 reflections with I > 2σ(I)
T_min = 0.248, T_max = 0.346	R_int = 0.000
2609 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.05	Δρ_max = 0.88 e Å⁻³
2609 reflections	Δρ_min = −0.29 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

	x	y	z	U_iso*/U_eq
C1	0.4051 (2)	0.2640 (5)	0.2830 (2)	0.0443 (7)
H1	0.4322	0.1261	0.2945	0.053*
C2	0.3780 (2)	0.3405 (5)	0.1953 (2)	0.0441 (7)
C3	0.3410 (2)	0.5470 (6)	0.1759 (2)	0.0509 (8)
H3	0.3226	0.5956	0.1163	0.061*
C4	0.3316 (2)	0.6805 (5)	0.2464 (2)	0.0504 (8)
H4	0.3079	0.8214	0.2342	0.060*
C5	0.3567 (2)	0.6075 (5)	0.3344 (2)	0.0477 (7)
H5	0.3506	0.7000	0.3813	0.057*
C6	0.3918 (2)	0.3935 (6)	0.3544 (2)	0.0472 (7)
C7	0.4073 (2)	0.2956 (6)	0.4461 (2)	0.0515 (8)
H7	0.4370	0.1601	0.4544	0.062*
C8	0.3834 (3)	0.3799 (6)	0.5171 (3)	0.0582 (9)
H8	0.3525	0.5139	0.5112	0.070*
C9	0.4039 (2)	0.2704 (6)	0.6041 (2)	0.0503 (8)
C10	0.3899 (2)	0.3888 (5)	0.6857 (2)	0.0422 (7)
C11	0.3495 (2)	0.5970 (6)	0.6819 (2)	0.0481 (7)
H11	0.3302	0.6680	0.6264	0.058*
C12	0.3382 (3)	0.6981 (6)	0.7600 (2)	0.0518 (8)
H12	0.3104	0.8355	0.7571	0.062*
C13	0.3684 (2)	0.5938 (6)	0.8414 (2)	0.0523 (8)
C14	0.4088 (3)	0.3879 (7)	0.8473 (2)	0.0580 (9)
H14	0.4292	0.3190	0.9032	0.070*
C15	0.4182 (2)	0.2872 (6)	0.7689 (2)	0.0525 (8)
H15	0.4442	0.1478	0.7721	0.063*
Br1	0.39001 (3)	0.15363 (7)	0.09849 (2)	0.06520 (19)
Cl1	0.35623 (9)	0.7258 (2)	0.93947 (7)	0.0815 (4)
O1	0.4300 (2)	0.0808 (5)	0.61022 (19)	0.0731 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0517 (16)	0.0409 (16)	0.0405 (16)	0.0034 (13)	0.0114 (13)	−0.0024 (13)
C2	0.0526 (17)	0.0432 (16)	0.0401 (16)	−0.0059 (13)	0.0181 (13)	−0.0060 (13)
C3	0.0623 (19)	0.0523 (19)	0.0414 (16)	0.0001 (16)	0.0187 (14)	0.0089 (15)
C4	0.0551 (18)	0.0391 (16)	0.060 (2)	0.0048 (14)	0.0191 (15)	0.0078 (14)
C5	0.0545 (18)	0.0426 (17)	0.0468 (17)	0.0035 (13)	0.0139 (14)	−0.0091 (14)
C6	0.0535 (17)	0.0461 (17)	0.0403 (16)	0.0080 (14)	0.0078 (13)	−0.0028 (13)
C7	0.0591 (19)	0.0495 (18)	0.0469 (18)	0.0030 (15)	0.0145 (15)	−0.0012 (15)
C8	0.071 (2)	0.059 (2)	0.0481 (19)	0.0158 (17)	0.0221 (17)	0.0028 (15)
C9	0.0515 (17)	0.0513 (19)	0.0463 (18)	0.0074 (15)	0.0081 (14)	−0.0043 (14)
C10	0.0420 (15)	0.0409 (16)	0.0451 (16)	−0.0005 (12)	0.0129 (12)	−0.0015 (13)
C11	0.0614 (18)	0.0457 (17)	0.0396 (16)	0.0064 (14)	0.0173 (14)	0.0036 (13)
C12	0.066 (2)	0.0447 (17)	0.0488 (18)	0.0072 (15)	0.0212 (15)	−0.0015 (14)
C13	0.0562 (18)	0.064 (2)	0.0406 (17)	−0.0010 (16)	0.0194 (14)	−0.0062 (15)
C14	0.068 (2)	0.067 (2)	0.0410 (18)	0.0094 (18)	0.0172 (16)	0.0081 (16)
C15	0.0568 (18)	0.0491 (18)	0.0523 (19)	0.0081 (15)	0.0147 (15)	0.0062 (15)
Br1	0.1023 (3)	0.0578 (3)	0.0422 (2)	−0.00177 (19)	0.0304 (2)	−0.00801 (15)
Cl1	0.1037 (8)	0.0997 (9)	0.0472 (5)	0.0144 (7)	0.0302 (5)	−0.0135 (5)
O1	0.102 (2)	0.0526 (15)	0.0671 (17)	0.0213 (15)	0.0250 (15)	−0.0046 (13)

Geometric parameters (Å, º) top

C1—C2	1.377 (5)	C8—H8	0.9300
C1—C6	1.393 (4)	C9—O1	1.216 (5)
C1—H1	0.9300	C9—C10	1.491 (4)
C2—C3	1.377 (5)	C10—C15	1.379 (5)
C2—Br1	1.902 (3)	C10—C11	1.398 (4)
C3—C4	1.379 (5)	C11—C12	1.382 (5)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.373 (5)	C12—C13	1.366 (5)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.411 (5)	C13—C14	1.384 (5)
C5—H5	0.9300	C13—Cl1	1.740 (3)
C6—C7	1.482 (5)	C14—C15	1.375 (5)
C7—C8	1.317 (5)	C14—H14	0.9300
C7—H7	0.9300	C15—H15	0.9300
C8—C9	1.446 (5)

C2—C1—C6	119.9 (3)	C9—C8—H8	119.0
C2—C1—H1	120.1	O1—C9—C8	120.1 (3)
C6—C1—H1	120.1	O1—C9—C10	120.2 (3)
C3—C2—C1	121.6 (3)	C8—C9—C10	119.7 (3)
C3—C2—Br1	119.3 (2)	C15—C10—C11	118.6 (3)
C1—C2—Br1	119.0 (2)	C15—C10—C9	118.2 (3)
C2—C3—C4	118.9 (3)	C11—C10—C9	123.2 (3)
C2—C3—H3	120.5	C12—C11—C10	120.5 (3)
C4—C3—H3	120.5	C12—C11—H11	119.7
C5—C4—C3	120.7 (3)	C10—C11—H11	119.7
C5—C4—H4	119.6	C13—C12—C11	119.2 (3)
C3—C4—H4	119.6	C13—C12—H12	120.4
C4—C5—C6	120.6 (3)	C11—C12—H12	120.4
C4—C5—H5	119.7	C12—C13—C14	121.5 (3)
C6—C5—H5	119.7	C12—C13—Cl1	118.7 (3)
C1—C6—C5	118.1 (3)	C14—C13—Cl1	119.7 (3)
C1—C6—C7	118.9 (3)	C15—C14—C13	118.7 (3)
C5—C6—C7	122.7 (3)	C15—C14—H14	120.6
C8—C7—C6	126.9 (3)	C13—C14—H14	120.6
C8—C7—H7	116.5	C14—C15—C10	121.4 (3)
C6—C7—H7	116.5	C14—C15—H15	119.3
C7—C8—C9	122.0 (3)	C10—C15—H15	119.3
C7—C8—H8	119.0

C6—C1—C2—C3	2.5 (5)	O1—C9—C10—C15	7.9 (5)
C6—C1—C2—Br1	−176.2 (2)	C8—C9—C10—C15	−174.1 (3)
C1—C2—C3—C4	0.5 (5)	O1—C9—C10—C11	−172.1 (3)
Br1—C2—C3—C4	179.3 (3)	C8—C9—C10—C11	5.9 (5)
C2—C3—C4—C5	−1.4 (5)	C15—C10—C11—C12	−0.2 (5)
C3—C4—C5—C6	−0.7 (5)	C9—C10—C11—C12	179.8 (3)
C2—C1—C6—C5	−4.5 (5)	C10—C11—C12—C13	1.1 (5)
C2—C1—C6—C7	170.4 (3)	C11—C12—C13—C14	−1.0 (6)
C4—C5—C6—C1	3.6 (5)	C11—C12—C13—Cl1	178.5 (3)
C4—C5—C6—C7	−171.1 (3)	C12—C13—C14—C15	−0.2 (6)
C1—C6—C7—C8	−167.8 (4)	Cl1—C13—C14—C15	−179.6 (3)
C5—C6—C7—C8	6.9 (6)	C13—C14—C15—C10	1.2 (5)
C6—C7—C8—C9	−178.8 (3)	C11—C10—C15—C14	−1.0 (5)
C7—C8—C9—O1	−12.1 (6)	C9—C10—C15—C14	179.0 (3)
C7—C8—C9—C10	169.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱ	0.93	2.53	3.328 (4)	144

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrClO
M_r	321.59
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	14.7421 (10), 6.1024 (4), 15.1874 (10)
β (°)	103.905 (2)
V (Å³)	1326.25 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.28
Crystal size (mm)	0.59 × 0.58 × 0.41

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.248, 0.346
No. of measured, independent and observed [I > 2σ(I)] reflections	2609, 2609, 2273
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.120, 1.05
No. of reflections	2609
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.88, −0.29

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ⁱ	0.93	2.53	3.328 (4)	144

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

BN thanks Mangalore University for providing research facilities.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sarojini, B. K., Narayana, B., Vijesh, A. M., Yathirajan, H. S. & Bolte, M. (2007). Acta Cryst. E63, o3656. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yathirajan, H. S., Sarojini, B. K., Bindya, S., Narayana, B. & Bolte, M. (2006). Acta Cryst. E62, o4046–o4047. Web of Science CSD CrossRef IUCr Journals Google Scholar

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(2E)-3-(3-Bromo­phen­yl)-1-(4-chloro­phen­yl)prop-2-en-1-one: a non-merohedral twin

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(2E)-3-(3-Bromophenyl)-1-(4-chlorophenyl)prop-2-en-1-one: a non-merohedral twin