1-(4-Bromo­phen­yl)-3-(3,4-dimethyl­phen­yl)prop-2-en-1-one

Zhou, Y.

doi:10.1107/S1600536810018106

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1412

https://doi.org/10.1107/S1600536810018106

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1-(4-Bromophenyl)-3-(3,4-dimethylphenyl)prop-2-en-1-one

Yu-xia Zhou ^a ^*

^aShandong Vocational College of Science and Technology, Weifang 261061, People's Republic of China
^*Correspondence e-mail: zhouyuxiajidian@163.com

(Received 13 May 2010; accepted 16 May 2010; online 22 May 2010)

In the title chalcone derivative, C₁₇H₁₅BrO, the dihedral angle between the two benzene rings is 48.13 (4)°. In the crystal, a short Br⋯Br contact of 3.5052 (10) Å occurs.

Related literature

For a related structure and background to chalcones, see: Fun et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₅BrO
M_r = 315.20
Triclinic, $[P \overline 1]$
a = 5.9786 (14) Å
b = 7.8437 (19) Å
c = 15.744 (4) Å
α = 99.054 (4)°
β = 99.602 (4)°
γ = 95.659 (4)°
V = 713.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 2.87 mm⁻¹
T = 298 K
0.25 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
3911 measured reflections
2620 independent reflections
2198 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.095
S = 1.09
2620 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810018106/hb5445sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018106/hb5445Isup2.hkl

checkCIF report

Comment top

As part of our search for new biologically active compounds we synthesized the title compound(I) and report its crystal structure herein.

In the crystal structure of compound(I)(fig.1),the dihedral angle between the two benzene rings(C1—C6) and (C7—C12) is 48.13 (4)°. All of the bond lengths and bond angles are in normal ranges and comparable to those in related structure (Fun et al., 2008).

Related literature top

For a related structure and background to chalcones, see: Fun et al. (2008).

Experimental top

A mixture of 4-bromohypnone (0.02 mol) and 3,4-dimethylbenzaldehyde (0.02 mol) and 10%NaOH (5 ml) was stirred in ethanol (30 ml) for 1.5 h to afford the title compound (yield 73%). Yellow blocks of (I) were obtailed by recrystallization from ethyl acetate at room temperature.

Structure description top

As part of our search for new biologically active compounds we synthesized the title compound(I) and report its crystal structure herein.

For a related structure and background to chalcones, see: Fun et al. (2008).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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

Fig. 1. The molecular structure of (I) with displacement ellipsoids are drawn at the 30% probability level.

1-(4-Bromophenyl)-3-(3,4-dimethylphenyl)prop-2-en-1-one top

Crystal data top

C₁₇H₁₅BrO	Z = 2
M_r = 315.20	F(000) = 320
Triclinic, P1	D_x = 1.468 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9786 (14) Å	Cell parameters from 2198 reflections
b = 7.8437 (19) Å	θ = 1.3–25.5°
c = 15.744 (4) Å	µ = 2.87 mm⁻¹
α = 99.054 (4)°	T = 298 K
β = 99.602 (4)°	Bar, yellow
γ = 95.659 (4)°	0.25 × 0.22 × 0.20 mm
V = 713.0 (3) Å³

Data collection top

Bruker SMART CCD diffractometer	2198 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Graphite monochromator	θ_max = 25.5°, θ_min = 1.3°
phi and ω scans	h = −7→7
3911 measured reflections	k = −9→6
2620 independent reflections	l = −18→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.048P)² + 0.2458P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2620 reflections	Δρ_max = 0.45 e Å⁻³
173 parameters	Δρ_min = −0.60 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.048 (4)

Crystal data top

C₁₇H₁₅BrO	γ = 95.659 (4)°
M_r = 315.20	V = 713.0 (3) Å³
Triclinic, P1	Z = 2
a = 5.9786 (14) Å	Mo Kα radiation
b = 7.8437 (19) Å	µ = 2.87 mm⁻¹
c = 15.744 (4) Å	T = 298 K
α = 99.054 (4)°	0.25 × 0.22 × 0.20 mm
β = 99.602 (4)°

Data collection top

Bruker SMART CCD diffractometer	2198 reflections with I > 2σ(I)
3911 measured reflections	R_int = 0.019
2620 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.09	Δρ_max = 0.45 e Å⁻³
2620 reflections	Δρ_min = −0.60 e Å⁻³
173 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Br	0.57731 (6)	0.43242 (4)	0.100602 (19)	0.06655 (18)
C11	0.5449 (5)	0.3857 (3)	0.21288 (17)	0.0440 (6)
O	0.2750 (3)	0.2761 (3)	0.48223 (13)	0.0628 (6)
C10	0.7328 (5)	0.4220 (4)	0.27985 (18)	0.0482 (6)
H10A	0.8724	0.4717	0.2706	0.058*
C17	0.4645 (5)	0.2760 (4)	0.46327 (17)	0.0455 (6)
C12	0.3349 (5)	0.3142 (4)	0.22550 (18)	0.0506 (7)
H12A	0.2100	0.2898	0.1796	0.061*
C9	0.7107 (4)	0.3834 (3)	0.36099 (17)	0.0448 (6)
H9A	0.8374	0.4048	0.4061	0.054*
C8	0.5010 (4)	0.3129 (3)	0.37593 (16)	0.0395 (5)
C6	1.1464 (4)	0.0981 (3)	0.80706 (18)	0.0453 (6)
C5	0.9589 (4)	0.1781 (4)	0.82839 (17)	0.0448 (6)
C3	0.8289 (4)	0.1904 (3)	0.67426 (17)	0.0408 (6)
C4	0.8024 (4)	0.2208 (3)	0.76150 (17)	0.0437 (6)
H4A	0.6759	0.2714	0.7755	0.052*
C16	0.6528 (5)	0.2356 (3)	0.60745 (17)	0.0437 (6)
H16A	0.5194	0.2656	0.6256	0.052*
C2	1.0206 (5)	0.1157 (3)	0.65442 (18)	0.0459 (6)
H2A	1.0448	0.0967	0.5970	0.055*
C7	0.3131 (5)	0.2796 (4)	0.30725 (17)	0.0464 (6)
H7A	0.1717	0.2335	0.3167	0.056*
C15	0.6631 (5)	0.2384 (4)	0.52402 (18)	0.0477 (6)
H15A	0.7966	0.2164	0.5036	0.057*
C1	1.1749 (5)	0.0697 (3)	0.72054 (19)	0.0474 (6)
H1A	1.3008	0.0184	0.7064	0.057*
C14	0.9249 (6)	0.2180 (5)	0.9221 (2)	0.0674 (9)
H14A	0.7885	0.2726	0.9242	0.101*
H14B	1.0541	0.2950	0.9567	0.101*
H14C	0.9103	0.1119	0.9450	0.101*
C13	1.3147 (6)	0.0413 (4)	0.8765 (2)	0.0635 (8)
H13A	1.4312	−0.0106	0.8501	0.095*
H13B	1.2362	−0.0421	0.9034	0.095*
H13C	1.3838	0.1406	0.9201	0.095*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.0949 (3)	0.0686 (3)	0.0421 (2)	0.01006 (17)	0.01910 (16)	0.02128 (15)
C11	0.0583 (16)	0.0408 (13)	0.0358 (13)	0.0098 (12)	0.0132 (12)	0.0091 (11)
O	0.0507 (12)	0.0955 (16)	0.0468 (11)	0.0114 (11)	0.0174 (9)	0.0161 (11)
C10	0.0477 (15)	0.0507 (15)	0.0470 (15)	0.0019 (12)	0.0133 (12)	0.0092 (12)
C17	0.0508 (16)	0.0485 (15)	0.0367 (13)	0.0058 (12)	0.0101 (11)	0.0043 (11)
C12	0.0514 (16)	0.0571 (17)	0.0394 (14)	0.0025 (13)	−0.0017 (12)	0.0104 (12)
C9	0.0420 (14)	0.0502 (15)	0.0387 (14)	0.0038 (11)	0.0027 (11)	0.0042 (11)
C8	0.0449 (14)	0.0387 (13)	0.0361 (13)	0.0085 (10)	0.0108 (10)	0.0052 (10)
C6	0.0446 (14)	0.0401 (13)	0.0501 (15)	0.0030 (11)	0.0045 (12)	0.0112 (12)
C5	0.0434 (14)	0.0507 (15)	0.0403 (14)	0.0011 (11)	0.0081 (11)	0.0106 (12)
C3	0.0434 (14)	0.0406 (13)	0.0395 (13)	0.0027 (10)	0.0096 (11)	0.0104 (11)
C4	0.0417 (14)	0.0500 (15)	0.0421 (14)	0.0088 (11)	0.0120 (11)	0.0098 (12)
C16	0.0459 (14)	0.0452 (14)	0.0413 (14)	0.0061 (11)	0.0113 (11)	0.0086 (11)
C2	0.0528 (15)	0.0460 (14)	0.0401 (14)	0.0052 (12)	0.0147 (12)	0.0052 (11)
C7	0.0423 (14)	0.0534 (16)	0.0428 (15)	0.0010 (12)	0.0067 (11)	0.0107 (12)
C15	0.0525 (16)	0.0562 (16)	0.0389 (14)	0.0138 (13)	0.0139 (12)	0.0120 (12)
C1	0.0432 (14)	0.0430 (14)	0.0580 (17)	0.0092 (11)	0.0149 (12)	0.0071 (12)
C14	0.0606 (19)	0.103 (3)	0.0422 (17)	0.0175 (17)	0.0120 (14)	0.0157 (17)
C13	0.0604 (19)	0.067 (2)	0.064 (2)	0.0181 (15)	0.0032 (15)	0.0181 (16)

Geometric parameters (Å, º) top

Br—C11	1.898 (3)	C3—C2	1.396 (4)
C11—C10	1.379 (4)	C3—C4	1.395 (4)
C11—C12	1.382 (4)	C3—C16	1.470 (4)
O—C17	1.219 (3)	C4—H4A	0.9300
C10—C9	1.382 (4)	C16—C15	1.329 (4)
C10—H10A	0.9300	C16—H16A	0.9300
C17—C15	1.480 (4)	C2—C1	1.389 (4)
C17—C8	1.495 (4)	C2—H2A	0.9300
C12—C7	1.381 (4)	C7—H7A	0.9300
C12—H12A	0.9300	C15—H15A	0.9300
C9—C8	1.391 (4)	C1—H1A	0.9300
C9—H9A	0.9300	C14—H14A	0.9600
C8—C7	1.396 (4)	C14—H14B	0.9600
C6—C1	1.387 (4)	C14—H14C	0.9600
C6—C5	1.400 (4)	C13—H13A	0.9600
C6—C13	1.510 (4)	C13—H13B	0.9600
C5—C4	1.393 (4)	C13—H13C	0.9600
C5—C14	1.512 (4)

C10—C11—C12	121.5 (2)	C3—C4—H4A	118.9
C10—C11—Br	119.1 (2)	C15—C16—C3	127.2 (3)
C12—C11—Br	119.4 (2)	C15—C16—H16A	116.4
C11—C10—C9	119.1 (2)	C3—C16—H16A	116.4
C11—C10—H10A	120.5	C1—C2—C3	119.9 (2)
C9—C10—H10A	120.5	C1—C2—H2A	120.1
O—C17—C15	122.0 (3)	C3—C2—H2A	120.1
O—C17—C8	119.9 (2)	C12—C7—C8	120.7 (2)
C15—C17—C8	118.0 (2)	C12—C7—H7A	119.7
C11—C12—C7	119.1 (2)	C8—C7—H7A	119.7
C11—C12—H12A	120.5	C16—C15—C17	120.7 (3)
C7—C12—H12A	120.5	C16—C15—H15A	119.6
C10—C9—C8	120.8 (2)	C17—C15—H15A	119.6
C10—C9—H9A	119.6	C6—C1—C2	121.8 (2)
C8—C9—H9A	119.6	C6—C1—H1A	119.1
C9—C8—C7	118.9 (2)	C2—C1—H1A	119.1
C9—C8—C17	123.1 (2)	C5—C14—H14A	109.5
C7—C8—C17	117.9 (2)	C5—C14—H14B	109.5
C1—C6—C5	119.0 (2)	H14A—C14—H14B	109.5
C1—C6—C13	120.0 (3)	C5—C14—H14C	109.5
C5—C6—C13	121.0 (3)	H14A—C14—H14C	109.5
C4—C5—C6	118.9 (2)	H14B—C14—H14C	109.5
C4—C5—C14	120.0 (2)	C6—C13—H13A	109.5
C6—C5—C14	121.1 (3)	C6—C13—H13B	109.5
C2—C3—C4	118.2 (2)	H13A—C13—H13B	109.5
C2—C3—C16	123.1 (2)	C6—C13—H13C	109.5
C4—C3—C16	118.8 (2)	H13A—C13—H13C	109.5
C5—C4—C3	122.3 (2)	H13B—C13—H13C	109.5
C5—C4—H4A	118.9

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BrO
M_r	315.20
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.9786 (14), 7.8437 (19), 15.744 (4)
α, β, γ (°)	99.054 (4), 99.602 (4), 95.659 (4)
V (Å³)	713.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.87
Crystal size (mm)	0.25 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3911, 2620, 2198
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.095, 1.09
No. of reflections	2620
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.60

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Bruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Chantrapromma, S., Patil, P. S., D'Silva, E. D. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o954–o955. 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