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

Escobar, C.A.; Trujillo, A.; Howard, J.A.K.; Fuentealba, M.

doi:10.1107/S1600536812006836

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o887

doi:10.1107/S1600536812006836

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

Carlos A. Escobar,^a ^* Alexander Trujillo,^a Judith A. K. Howard ^b and Mauricio Fuentealba ^b

^aDepartamento de Ciencias Quimicas, Facultad de Ciencias Exactas, Universidad Andres Bello, Santiago, Chile, and ^bDepartment of Chemistry, Durham University, Durham DH1 3LE, England
^*Correspondence e-mail: cescobar@unab.cl

(Received 1 February 2012; accepted 15 February 2012; online 29 February 2012)

The molecular structure of the title compound, C₁₇H₁₅BrO₃, consists of a bromophenyl and a 3,4-dimethoxyphenyl group linked through a prop-2-en-1-one spacer. The C=C double bond displays an E conformation, while the carbonyl group shows an S-cis conformation relative to the double bond.

Related literature

For the Suzuki reaction, see: Miyaura & Suzuki (1995 ); Bringmann et al. (2005 ). For bichalcone derivatives, see: Shetonde et al. (2010 ). For related structures, see: Escobar et al. (2008 ); Valdebenito et al. (2010 ); Chu et al. (2004 ); Radha Krishna et al. (2005 ); Wu et al. (2005 ).

Experimental

Crystal data

C₁₇H₁₅BrO₃
M_r = 347.20
Monoclinic, P 2₁ /c
a = 12.7946 (5) Å
b = 3.9373 (1) Å
c = 29.8209 (10) Å
β = 109.219 (3)°
V = 1418.54 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.91 mm⁻¹
T = 120 K
0.2 × 0.12 × 0.08 mm

Data collection

Agilent Xcalibur Sapphire3 Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.802, T_max = 1.000
12861 measured reflections
3429 independent reflections
2895 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.074
S = 1.10
3429 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006836/fj2515sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006836/fj2515Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006836/fj2515Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536812006836/fj2515Isup4.cml

checkCIF report

Comment top

From the synthetic point of view, bromochalcones are the choice precursors to accomplish the C—C bond formation, through the Suzuki reaction, one of the most popular and powerful methods for coupling aryl–aryl moieties (Miyaura & Suzuki, 1995; Bringmann et al., 2005), to produce symmetric or asymmetric biphenyls, this being the entry to bichalcones (Shetonde et al., 2010).

The molecular structure of the title compound displays two phenyl rings connected through the organic prop-2-en-1-one spacer. As shown in Fig. 1, one phenyl ring is substituted at positions 3 and 4 with methoxy groups, while the other is substituted at position 3' with one Br atom.

The dihedral angle between the two aromatic rings joined by the conjugated spacer is 26.59 (9)°. On the other hand, the spacer formed by C10—C9—C8—C7—O1—C1 can be considered as a plane with a RMSD of 0.029 Å. This feature is also observed in other chalcones (Escobar et al. 2008; Valdebenito et al., 2010; Chu et al. 2004; Radha Krishna et al. 2005; Wu et al. 2005).

Finally, both inter- and intramolecular hydrogen bonds are not observed in the crystalline packing of title compound.

Related literature top

For the Suzuki reaction, see: Miyaura & Suzuki (1995); Bringmann et al. (2005). For bichalcone derivatives, see: Shetonde et al. (2010). For related structures, see: Escobar et al. (2008); Valdebenito et al. (2010); Chu et al. (2004); Radha Krishna et al. (2005); Wu et al. (2005).

Experimental top

A mixture of 3-bromoacetophenone (0.5 g, 2,5 mmol) and 3,4-dimethoxibenzaldehyde (0.41 g, 2,5 mmol), were dissolved in Methanol (50 ml), and were treated with KOH (2 g, dissolved in 20 ml methanol). After 20 min 30 ml of water were added, and the title compound precipitated as a yellow solid. Then, it was filtered and recrystallized in ethanol to yield 1.27 g (73%) of a yellow solid. m.p.117–120°C. IR (KBr): ν = 1657 (CO), cm^-1. ¹H-NMR (400 MHz, CDCl₃): d = 3.94 (3H, s, OCH₃), 3.96 (3H, s, OCH₃), 6.90 (1H, d, J = 8.3 Hz, H5), 7.16 (1H, m, H2), 7.24 (1H, d, J = 7.2 Hz., H6), 7.32 (1H, d, J = 15.6 Hz., Ha), 7.38 (1H, t, J = 7.8 Hz., H5), 7.70 (1H, d, J = 7.9 Hz., H4), 7.77 (1H, d, J = 15.6 Hz., Hb), 7.93 (1H, d, J = 7.7 Hz., H6), 8.13 (1H, m, H2). ¹³C-NMR (400 MHz, CDCl₃): d = 56.1, 110.2, 111.2, 119.4, 122.9, 123.5, 127.0, 127.6, 130.2, 131.4, 135.4, 140.4, 146.0, 149.3, 151.8, 189.1. HRMS calc. for C₁₇H₁₅BrO₃ 346.02046; Found 346.019994.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of title compound with full atom numbering scheme. Displacement ellipsoids are presented at 30% probability level and H atoms are shown as spheres.

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

Crystal data top

C₁₇H₁₅BrO₃	F(000) = 704
M_r = 347.20	D_x = 1.626 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
a = 12.7946 (5) Å	Cell parameters from 3587 reflections
b = 3.9373 (1) Å	θ = 2.6–29.0°
c = 29.8209 (10) Å	µ = 2.91 mm⁻¹
β = 109.219 (3)°	T = 120 K
V = 1418.54 (8) Å³	Prism, colourless
Z = 4	0.2 × 0.12 × 0.08 mm

Data collection top

Agilent Xcalibur Sapphire3 Gemini ultra diffractometer	3429 independent reflections
Radiation source: Enhance (Mo) X-ray source	2895 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 16.1511 pixels mm^-1	θ_max = 29.0°, θ_min = 2.6°
ω scans	h = −17→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −5→5
T_min = 0.802, T_max = 1.000	l = −40→40
12861 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.019P)² + 1.5139P] where P = (F_o² + 2F_c²)/3
3429 reflections	(Δ/σ)_max = 0.002
192 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₇H₁₅BrO₃	V = 1418.54 (8) Å³
M_r = 347.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.7946 (5) Å	µ = 2.91 mm⁻¹
b = 3.9373 (1) Å	T = 120 K
c = 29.8209 (10) Å	0.2 × 0.12 × 0.08 mm
β = 109.219 (3)°

Data collection top

Agilent Xcalibur Sapphire3 Gemini ultra diffractometer	3429 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2895 reflections with I > 2σ(I)
T_min = 0.802, T_max = 1.000	R_int = 0.047
12861 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.10	Δρ_max = 0.63 e Å⁻³
3429 reflections	Δρ_min = −0.41 e Å⁻³
192 parameters

Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	−0.11568 (2)	0.90741 (7)	0.528213 (9)	0.01853 (9)
O1	−0.25274 (14)	0.3062 (5)	0.31571 (6)	0.0198 (4)
O2	0.40922 (14)	0.3072 (5)	0.32327 (6)	0.0173 (4)
O3	0.37580 (14)	0.5457 (5)	0.39741 (6)	0.0190 (4)
C16	0.4322 (2)	0.1612 (7)	0.28340 (10)	0.0205 (6)
H16A	0.3873	0.2751	0.2542	0.031*
H16B	0.4141	−0.0814	0.2813	0.031*
H16C	0.5109	0.1902	0.2874	0.031*
C9	−0.0247 (2)	0.2800 (7)	0.32953 (9)	0.0143 (5)
H9	−0.0759	0.1507	0.3052	0.017*
C11	0.1119 (2)	0.1273 (6)	0.29162 (9)	0.0143 (5)
H11	0.0535	0.0184	0.2676	0.017*
C12	0.2171 (2)	0.1330 (6)	0.28749 (9)	0.0148 (5)
H12	0.2298	0.0357	0.2606	0.018*
C14	0.2834 (2)	0.4212 (7)	0.36346 (9)	0.0143 (5)
C1	−0.2297 (2)	0.6078 (7)	0.38681 (9)	0.0140 (5)
C15	0.1780 (2)	0.4234 (7)	0.36627 (9)	0.0144 (5)
H15	0.1649	0.5243	0.3928	0.017*
C5	−0.3827 (2)	0.8723 (7)	0.40364 (10)	0.0201 (6)
H5	−0.4579	0.9429	0.3932	0.024*
C10	0.0897 (2)	0.2760 (6)	0.32972 (9)	0.0130 (5)
C3	−0.2072 (2)	0.8273 (6)	0.46427 (9)	0.0142 (5)
C4	−0.3163 (2)	0.9344 (7)	0.45004 (10)	0.0178 (6)
H4	−0.3450	1.0479	0.4716	0.021*
C8	−0.0668 (2)	0.4429 (7)	0.35928 (9)	0.0149 (5)
H8	−0.0187	0.5619	0.3858	0.018*
C2	−0.1622 (2)	0.6663 (6)	0.43363 (9)	0.0135 (5)
H2	−0.0869	0.5968	0.4442	0.016*
C13	0.3031 (2)	0.2829 (6)	0.32325 (9)	0.0138 (5)
C7	−0.1871 (2)	0.4390 (7)	0.35127 (9)	0.0143 (5)
C17	0.3612 (2)	0.6874 (7)	0.43882 (9)	0.0212 (6)
H17A	0.3096	0.8790	0.4298	0.032*
H17B	0.4327	0.7667	0.4604	0.032*
H17C	0.3313	0.5140	0.4548	0.032*
C6	−0.3401 (2)	0.7083 (7)	0.37247 (10)	0.0175 (6)
H6	−0.3866	0.6638	0.3409	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02037 (14)	0.02143 (14)	0.01387 (14)	−0.00093 (12)	0.00574 (10)	−0.00270 (12)
O1	0.0164 (9)	0.0267 (11)	0.0153 (10)	−0.0041 (8)	0.0037 (8)	−0.0030 (8)
O2	0.0138 (9)	0.0241 (10)	0.0154 (10)	0.0002 (8)	0.0068 (7)	−0.0033 (8)
O3	0.0141 (9)	0.0302 (11)	0.0126 (10)	−0.0035 (8)	0.0042 (7)	−0.0081 (9)
C16	0.0222 (14)	0.0244 (15)	0.0198 (15)	0.0009 (12)	0.0138 (12)	−0.0032 (12)
C9	0.0151 (13)	0.0143 (12)	0.0115 (13)	−0.0014 (11)	0.0017 (10)	0.0032 (11)
C11	0.0151 (12)	0.0144 (13)	0.0115 (13)	0.0002 (10)	0.0018 (10)	0.0005 (11)
C12	0.0198 (13)	0.0146 (13)	0.0115 (13)	0.0031 (11)	0.0073 (10)	−0.0011 (11)
C14	0.0173 (12)	0.0132 (12)	0.0113 (13)	−0.0004 (11)	0.0030 (10)	−0.0002 (11)
C1	0.0150 (12)	0.0128 (12)	0.0148 (13)	−0.0034 (11)	0.0058 (10)	0.0026 (11)
C15	0.0190 (13)	0.0143 (12)	0.0111 (13)	0.0019 (11)	0.0065 (10)	−0.0001 (11)
C5	0.0137 (13)	0.0235 (15)	0.0237 (15)	0.0011 (11)	0.0071 (11)	0.0050 (13)
C10	0.0150 (12)	0.0115 (12)	0.0126 (13)	0.0025 (10)	0.0048 (10)	0.0031 (10)
C3	0.0156 (12)	0.0133 (13)	0.0131 (14)	−0.0031 (10)	0.0039 (10)	0.0019 (10)
C4	0.0168 (13)	0.0176 (13)	0.0217 (15)	0.0010 (11)	0.0102 (11)	−0.0001 (12)
C8	0.0146 (12)	0.0164 (13)	0.0128 (13)	−0.0009 (11)	0.0033 (10)	0.0017 (11)
C2	0.0104 (12)	0.0140 (13)	0.0174 (14)	−0.0024 (10)	0.0064 (10)	0.0030 (11)
C13	0.0141 (12)	0.0135 (12)	0.0141 (13)	0.0016 (10)	0.0052 (10)	0.0031 (11)
C7	0.0155 (12)	0.0124 (12)	0.0141 (13)	−0.0005 (11)	0.0036 (10)	0.0036 (11)
C17	0.0201 (14)	0.0285 (16)	0.0147 (14)	−0.0036 (12)	0.0054 (11)	−0.0065 (12)
C6	0.0159 (13)	0.0203 (14)	0.0141 (14)	−0.0026 (11)	0.0019 (10)	0.0025 (11)

Geometric parameters (Å, º) top

Br1—C3	1.907 (3)	C1—C2	1.398 (3)
O1—C7	1.232 (3)	C1—C7	1.498 (4)
O2—C16	1.436 (3)	C1—C6	1.391 (4)
O2—C13	1.361 (3)	C15—H15	0.9500
O3—C14	1.369 (3)	C15—C10	1.411 (3)
O3—C17	1.422 (3)	C5—H5	0.9500
C16—H16A	0.9800	C5—C4	1.387 (4)
C16—H16B	0.9800	C5—C6	1.383 (4)
C16—H16C	0.9800	C3—C4	1.384 (4)
C9—H9	0.9500	C3—C2	1.384 (4)
C9—C10	1.462 (3)	C4—H4	0.9500
C9—C8	1.343 (4)	C8—H8	0.9500
C11—H11	0.9500	C8—C7	1.477 (3)
C11—C12	1.391 (3)	C2—H2	0.9500
C11—C10	1.388 (3)	C17—H17A	0.9800
C12—H12	0.9500	C17—H17B	0.9800
C12—C13	1.387 (3)	C17—H17C	0.9800
C14—C15	1.379 (3)	C6—H6	0.9500
C14—C13	1.413 (4)

C13—O2—C16	116.6 (2)	C11—C10—C15	118.5 (2)
C14—O3—C17	117.0 (2)	C15—C10—C9	123.0 (2)
O2—C16—H16A	109.5	C4—C3—Br1	118.8 (2)
O2—C16—H16B	109.5	C2—C3—Br1	118.96 (19)
O2—C16—H16C	109.5	C2—C3—C4	122.3 (2)
H16A—C16—H16B	109.5	C5—C4—H4	120.7
H16A—C16—H16C	109.5	C3—C4—C5	118.5 (2)
H16B—C16—H16C	109.5	C3—C4—H4	120.7
C10—C9—H9	115.8	C9—C8—H8	119.6
C8—C9—H9	115.8	C9—C8—C7	120.8 (2)
C8—C9—C10	128.5 (2)	C7—C8—H8	119.6
C12—C11—H11	119.0	C1—C2—H2	120.7
C10—C11—H11	119.0	C3—C2—C1	118.7 (2)
C10—C11—C12	122.0 (2)	C3—C2—H2	120.7
C11—C12—H12	120.5	O2—C13—C12	124.7 (2)
C13—C12—C11	119.0 (2)	O2—C13—C14	115.4 (2)
C13—C12—H12	120.5	C12—C13—C14	119.9 (2)
O3—C14—C15	125.2 (2)	O1—C7—C1	119.5 (2)
O3—C14—C13	114.5 (2)	O1—C7—C8	121.5 (2)
C15—C14—C13	120.3 (2)	C8—C7—C1	118.9 (2)
C2—C1—C7	122.0 (2)	O3—C17—H17A	109.5
C6—C1—C2	119.4 (2)	O3—C17—H17B	109.5
C6—C1—C7	118.6 (2)	O3—C17—H17C	109.5
C14—C15—H15	119.9	H17A—C17—H17B	109.5
C14—C15—C10	120.1 (2)	H17A—C17—H17C	109.5
C10—C15—H15	119.9	H17B—C17—H17C	109.5
C4—C5—H5	119.8	C1—C6—H6	119.6
C6—C5—H5	119.8	C5—C6—C1	120.7 (2)
C6—C5—C4	120.3 (2)	C5—C6—H6	119.6
C11—C10—C9	118.4 (2)

Br1—C3—C4—C5	−179.3 (2)	C10—C11—C12—C13	2.0 (4)
Br1—C3—C2—C1	179.90 (18)	C4—C5—C6—C1	−1.0 (4)
O3—C14—C15—C10	−177.6 (2)	C4—C3—C2—C1	−0.5 (4)
O3—C14—C13—O2	−2.7 (3)	C8—C9—C10—C11	−171.3 (3)
O3—C14—C13—C12	176.7 (2)	C8—C9—C10—C15	7.1 (4)
C16—O2—C13—C12	−0.9 (4)	C2—C1—C7—O1	159.4 (2)
C16—O2—C13—C14	178.5 (2)	C2—C1—C7—C8	−22.0 (4)
C9—C8—C7—O1	−4.7 (4)	C2—C1—C6—C5	1.6 (4)
C9—C8—C7—C1	176.7 (2)	C2—C3—C4—C5	1.1 (4)
C11—C12—C13—O2	−179.5 (2)	C13—C14—C15—C10	2.3 (4)
C11—C12—C13—C14	1.1 (4)	C7—C1—C2—C3	179.2 (2)
C12—C11—C10—C9	175.6 (2)	C7—C1—C6—C5	−178.5 (2)
C12—C11—C10—C15	−2.9 (4)	C17—O3—C14—C15	0.2 (4)
C14—C15—C10—C9	−177.7 (2)	C17—O3—C14—C13	−179.8 (2)
C14—C15—C10—C11	0.7 (4)	C6—C1—C2—C3	−0.8 (4)
C15—C14—C13—O2	177.3 (2)	C6—C1—C7—O1	−20.6 (4)
C15—C14—C13—C12	−3.3 (4)	C6—C1—C7—C8	158.1 (2)
C10—C9—C8—C7	175.1 (2)	C6—C5—C4—C3	−0.3 (4)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅BrO₃
M_r	347.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	12.7946 (5), 3.9373 (1), 29.8209 (10)
β (°)	109.219 (3)
V (Å³)	1418.54 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.91
Crystal size (mm)	0.2 × 0.12 × 0.08

Data collection
Diffractometer	Agilent Xcalibur Sapphire3 Gemini ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.802, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12861, 3429, 2895
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.683

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.074, 1.10
No. of reflections	3429
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.41

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

This work was supported by FONDECYT through grant Nos. 1080147 and 3110066. MF thanks to Becaschile Programme (Chile) for support through a postdoctoral fellowship.

References

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