2-Bromo-1-(4-methyl­phen­yl)-3-phenyl­prop-2-en-1-one

Fun, H.-K.; Jebas, S.R.; Patil, P.S.; Karthikeyan, M.S.; Dharmaprakash, S.M.

doi:10.1107/S1600536808022289

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1559

doi:10.1107/S1600536808022289

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ADDENDA AND ERRATA

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2-Bromo-1-(4-methylphenyl)-3-phenylprop-2-en-1-one

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ P. S. Patil,^b M. S. Karthikeyan ^c and S. M. Dharmaprakash ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Physics, Mangalore University, Mangalagangotri, Mangalore 574 199, India, and ^cSyngene International Pvt Limited, Plot Nos. 2 and 3 C, Unit-II, Bommansandra, Industrial Area, Banglore 560 099, India
^*Correspondence e-mail: hkfun@usm.my

(Received 14 July 2008; accepted 16 July 2008; online 19 July 2008)

In the crystal structure of the title compound, C₁₆H₁₃BrO, the two benzene rings are twisted from each other with a dihedral angle of 52.55 (9)°. Both an intramolecular C—H⋯Br hydrogen bond, which generates an S(6) ring motif, and a short Br⋯O contact [2.9907 (19) Å] may influence the conformation of the molecule. The crystal packing is stabilized by weak intermolecular C—H⋯O interactions.

Related literature

For related literature on chalcone derivatives, see: Fun et al. (2008 ); Patil et al. (2006 , 2007 ). For related literature on experimental preparation, see: Shivarama Holla et al. (2006 ). For standard bond-length data, see: Allen et al. (1987 ). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₃BrO
M_r = 301.17
Orthorhombic, P b c a
a = 8.7192 (2) Å
b = 11.5819 (2) Å
c = 26.4769 (6) Å
V = 2673.77 (10) Å³
Z = 8
Mo Kα radiation
μ = 3.06 mm⁻¹
T = 100.0 (1) K
0.20 × 0.20 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.556, T_max = 0.715
14370 measured reflections
3893 independent reflections
2462 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.090
S = 1.00
3893 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O1ⁱ	0.93	2.54	3.163 (3)	124
C11—H11A⋯Br1	0.93	2.69	3.377 (3)	131
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022289/lh2662sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022289/lh2662Isup2.hkl

checkCIF report

Comment top

As part of our crystallographic studies on chalcone derivatives (Fun et al., 2008; Patil et al., 2006,2007) the title compound (I) was synthesized and its crystal structure is reported here.

In the crystal structure of the title compound (I), the bond lengths have have normal values (Allen et al., 1987). The two benzene rings (C1—C6 & C10—C15) are twisted from each other with the dihedral angle of 52.55 (9)°.

Both an intramolecular C—H··· Br hydrogen bond, which generates an S(6) ring motif, and a short Br···O =2.9907 (19)Å contact may influence the conformation of the molecule. The crystal packing is stabilized by weak C—H···O intermolecular interactions.

Related literature top

For related literature on chalcone derivatives, see: Fun et al. (2008); Patil et al. (2006, 2007). For related literature on experimental preparation, see: Shivarama Holla et al. (2006). For standard bond-length data, see: Allen et al. (1987). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

1-(4-methylphenyl)-3-phenylprop-2-en-1-one (1 mmol) was prepared by a literature procedure (Shivarama Holla et al., 2006). To a solution of 1- (4-methylphenyl)-3-phenylprop-2-en-1-one (1 mmol) in chloroform (25 ml), bromine (1 mmol) was added slowly with stirring. After the completion of addition of bromine (1 mmol), the reaction mixture was stirred for 24 h. Excess of chloroform was distilled off and the precipitated 2,3- dibromo-1-(4- methylphenyl)-3-phenylpropan-1-one was filtered off and dried. A mixture of dibromopropanone (1 mmol) and triethylamine(1 mmol) in dry benzene (30 ml) was added and the resultant mixture was stirred for 24 h. The excess of solvent when removed under reduced pressure gave the title compound which crystallized from acetone by slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. Hydrogen bonds and Br···O short contacts are shown as dashed lines.

(I) top

Crystal data top

C₁₆H₁₃BrO	F(000) = 1216
M_r = 301.17	D_x = 1.496 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1664 reflections
a = 8.7192 (2) Å	θ = 2.8–23.7°
b = 11.5819 (2) Å	µ = 3.06 mm⁻¹
c = 26.4769 (6) Å	T = 100 K
V = 2673.77 (10) Å³	Block, colourless
Z = 8	0.20 × 0.20 × 0.11 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3893 independent reflections
Radiation source: fine-focus sealed tube	2462 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
ϕ and ω scans	θ_max = 30.1°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→9
T_min = 0.556, T_max = 0.715	k = −16→12
14370 measured reflections	l = −36→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0317P)²] where P = (F_o² + 2F_c²)/3
3893 reflections	(Δ/σ)_max < 0.001
164 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₁₆H₁₃BrO	V = 2673.77 (10) Å³
M_r = 301.17	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.7192 (2) Å	µ = 3.06 mm⁻¹
b = 11.5819 (2) Å	T = 100 K
c = 26.4769 (6) Å	0.20 × 0.20 × 0.11 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3893 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2462 reflections with I > 2σ(I)
T_min = 0.556, T_max = 0.715	R_int = 0.070
14370 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.00	Δρ_max = 0.43 e Å⁻³
3893 reflections	Δρ_min = −0.54 e Å⁻³
164 parameters

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Br1	0.13862 (3)	0.42397 (2)	0.062535 (10)	0.02216 (9)
O1	0.3082 (2)	0.38663 (17)	0.15935 (7)	0.0253 (5)
C1	0.4236 (3)	0.6775 (2)	0.16809 (10)	0.0177 (6)
H1A	0.3563	0.7084	0.1444	0.021*
C2	0.4991 (4)	0.7501 (3)	0.20151 (10)	0.0228 (7)
H2A	0.4813	0.8292	0.2005	0.027*
C3	0.6008 (4)	0.7049 (3)	0.23638 (10)	0.0262 (7)
H3A	0.6512	0.7537	0.2588	0.031*
C4	0.6275 (4)	0.5867 (3)	0.23785 (10)	0.0266 (7)
H4A	0.6977	0.5565	0.2608	0.032*
C5	0.5499 (3)	0.5141 (3)	0.20533 (10)	0.0214 (6)
H5A	0.5657	0.4348	0.2071	0.026*
C6	0.4477 (3)	0.5591 (2)	0.16967 (9)	0.0158 (6)
C7	0.3529 (3)	0.4759 (2)	0.13968 (9)	0.0159 (6)
C8	0.3122 (3)	0.5048 (2)	0.08629 (9)	0.0144 (6)
C9	0.3995 (3)	0.5748 (2)	0.05796 (9)	0.0143 (5)
H9A	0.4848	0.6018	0.0754	0.017*
C10	0.3931 (3)	0.6191 (2)	0.00603 (9)	0.0150 (6)
C11	0.2836 (3)	0.5907 (2)	−0.03059 (10)	0.0188 (6)
H11A	0.2098	0.5348	−0.0238	0.023*
C12	0.2854 (3)	0.6461 (3)	−0.07730 (10)	0.0214 (6)
H12A	0.2119	0.6268	−0.1013	0.026*
C13	0.3942 (3)	0.7295 (2)	−0.08878 (9)	0.0198 (6)
C14	0.5065 (4)	0.7535 (2)	−0.05306 (9)	0.0208 (6)
H14A	0.5829	0.8070	−0.0605	0.025*
C15	0.5059 (3)	0.6990 (2)	−0.00666 (9)	0.0176 (6)
H15A	0.5825	0.7160	0.0166	0.021*
C16	0.3901 (4)	0.7951 (3)	−0.13811 (10)	0.0304 (8)
H16A	0.3307	0.7526	−0.1624	0.046*
H16B	0.4928	0.8047	−0.1506	0.046*
H16C	0.3444	0.8694	−0.1328	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02062 (15)	0.02191 (16)	0.02395 (15)	−0.00743 (14)	−0.00516 (12)	0.00364 (12)
O1	0.0315 (13)	0.0193 (11)	0.0252 (11)	−0.0079 (10)	−0.0037 (9)	0.0057 (9)
C1	0.0193 (15)	0.0186 (15)	0.0152 (13)	0.0013 (13)	0.0009 (11)	0.0003 (11)
C2	0.0271 (17)	0.0233 (16)	0.0180 (13)	−0.0026 (14)	0.0031 (12)	−0.0054 (12)
C3	0.0308 (19)	0.0347 (19)	0.0130 (13)	−0.0064 (16)	−0.0013 (12)	−0.0074 (12)
C4	0.0237 (16)	0.039 (2)	0.0169 (13)	−0.0012 (17)	−0.0041 (12)	0.0032 (12)
C5	0.0280 (17)	0.0193 (16)	0.0170 (13)	0.0043 (14)	0.0008 (13)	0.0025 (11)
C6	0.0167 (14)	0.0197 (16)	0.0110 (12)	0.0007 (12)	0.0033 (10)	0.0019 (10)
C7	0.0152 (14)	0.0149 (14)	0.0177 (13)	0.0020 (12)	0.0008 (11)	0.0013 (11)
C8	0.0141 (13)	0.0136 (14)	0.0155 (13)	−0.0018 (11)	−0.0013 (11)	−0.0022 (10)
C9	0.0121 (13)	0.0138 (13)	0.0168 (12)	0.0022 (12)	−0.0004 (10)	−0.0039 (11)
C10	0.0198 (16)	0.0109 (13)	0.0142 (12)	0.0038 (12)	−0.0001 (11)	−0.0029 (10)
C11	0.0184 (15)	0.0199 (16)	0.0181 (13)	0.0010 (13)	0.0005 (11)	−0.0011 (11)
C12	0.0199 (16)	0.0273 (17)	0.0171 (13)	0.0038 (14)	−0.0025 (11)	−0.0013 (12)
C13	0.0250 (17)	0.0218 (15)	0.0125 (13)	0.0074 (13)	0.0041 (11)	0.0027 (11)
C14	0.0274 (17)	0.0174 (15)	0.0177 (13)	−0.0021 (13)	0.0047 (12)	0.0022 (11)
C15	0.0214 (15)	0.0157 (15)	0.0157 (13)	−0.0024 (13)	−0.0004 (11)	−0.0033 (11)
C16	0.036 (2)	0.0352 (19)	0.0198 (14)	0.0072 (16)	−0.0008 (13)	0.0096 (13)

Geometric parameters (Å, º) top

Br1—C8	1.888 (3)	C9—C10	1.469 (3)
O1—C7	1.221 (3)	C9—H9A	0.9300
C1—C2	1.386 (4)	C10—C15	1.391 (4)
C1—C6	1.388 (4)	C10—C11	1.400 (4)
C1—H1A	0.9300	C11—C12	1.394 (4)
C2—C3	1.383 (4)	C11—H11A	0.9300
C2—H2A	0.9300	C12—C13	1.387 (4)
C3—C4	1.390 (4)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.389 (4)
C4—C5	1.381 (4)	C13—C16	1.511 (4)
C4—H4A	0.9300	C14—C15	1.382 (3)
C5—C6	1.399 (4)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C6—C7	1.497 (4)	C16—H16A	0.9600
C7—C8	1.496 (3)	C16—H16B	0.9600
C8—C9	1.341 (4)	C16—H16C	0.9600

C2—C1—C6	120.5 (3)	C10—C9—H9A	112.3
C2—C1—H1A	119.7	C15—C10—C11	118.1 (2)
C6—C1—H1A	119.7	C15—C10—C9	115.5 (2)
C3—C2—C1	120.1 (3)	C11—C10—C9	126.3 (3)
C3—C2—H2A	120.0	C12—C11—C10	119.9 (3)
C1—C2—H2A	120.0	C12—C11—H11A	120.1
C2—C3—C4	119.9 (3)	C10—C11—H11A	120.1
C2—C3—H3A	120.0	C13—C12—C11	121.5 (3)
C4—C3—H3A	120.0	C13—C12—H12A	119.2
C5—C4—C3	120.0 (3)	C11—C12—H12A	119.2
C5—C4—H4A	120.0	C12—C13—C14	118.2 (2)
C3—C4—H4A	120.0	C12—C13—C16	121.5 (3)
C4—C5—C6	120.4 (3)	C14—C13—C16	120.3 (3)
C4—C5—H5A	119.8	C15—C14—C13	120.7 (3)
C6—C5—H5A	119.8	C15—C14—H14A	119.6
C1—C6—C5	119.0 (3)	C13—C14—H14A	119.6
C1—C6—C7	122.4 (2)	C14—C15—C10	121.4 (3)
C5—C6—C7	118.0 (2)	C14—C15—H15A	119.3
O1—C7—C8	121.1 (2)	C10—C15—H15A	119.3
O1—C7—C6	119.7 (2)	C13—C16—H16A	109.5
C8—C7—C6	119.2 (2)	C13—C16—H16B	109.5
C9—C8—C7	122.0 (2)	H16A—C16—H16B	109.5
C9—C8—Br1	124.7 (2)	C13—C16—H16C	109.5
C7—C8—Br1	113.19 (19)	H16A—C16—H16C	109.5
C8—C9—C10	135.5 (3)	H16B—C16—H16C	109.5
C8—C9—H9A	112.3

C6—C1—C2—C3	0.8 (4)	C6—C7—C8—Br1	−158.5 (2)
C1—C2—C3—C4	0.1 (4)	C7—C8—C9—C10	179.8 (3)
C2—C3—C4—C5	−1.5 (4)	Br1—C8—C9—C10	5.1 (5)
C3—C4—C5—C6	2.0 (4)	C8—C9—C10—C15	175.3 (3)
C2—C1—C6—C5	−0.3 (4)	C8—C9—C10—C11	−3.2 (5)
C2—C1—C6—C7	171.0 (3)	C15—C10—C11—C12	−3.1 (4)
C4—C5—C6—C1	−1.1 (4)	C9—C10—C11—C12	175.3 (3)
C4—C5—C6—C7	−172.8 (3)	C10—C11—C12—C13	0.3 (4)
C1—C6—C7—O1	−136.9 (3)	C11—C12—C13—C14	2.5 (4)
C5—C6—C7—O1	34.5 (4)	C11—C12—C13—C16	−176.0 (3)
C1—C6—C7—C8	42.0 (4)	C12—C13—C14—C15	−2.4 (4)
C5—C6—C7—C8	−146.6 (3)	C16—C13—C14—C15	176.1 (3)
O1—C7—C8—C9	−154.8 (3)	C13—C14—C15—C10	−0.5 (4)
C6—C7—C8—C9	26.3 (4)	C11—C10—C15—C14	3.2 (4)
O1—C7—C8—Br1	20.4 (3)	C9—C10—C15—C14	−175.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1ⁱ	0.93	2.54	3.163 (3)	124
C11—H11A···Br1	0.93	2.69	3.377 (3)	131

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃BrO
M_r	301.17
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	8.7192 (2), 11.5819 (2), 26.4769 (6)
V (Å³)	2673.77 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.06
Crystal size (mm)	0.20 × 0.20 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.556, 0.715
No. of measured, independent and observed [I > 2σ(I)] reflections	14370, 3893, 2462
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.090, 1.00
No. of reflections	3893
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.54

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1ⁱ	0.93	2.54	3.163 (3)	124.3
C11—H11A···Br1	0.93	2.69	3.377 (3)	131.0

Symmetry code: (i) −x+1/2, y+1/2, z.

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for a postdoctoral research fellowship.

References

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