(E)-1-(4-Bromo-phen-yl)-3-(3,4,5-trimethoxy-phen-yl)prop-2-en-1-one.

In the title compound, C(18)H(17)BrO(4), the dihedral angle between the 4-bromo-phenyl and 3,4,5-trimethoxy-phenyl rings is 44.18 (6)°. In the crystal structure, the mol-ecules are linked by C-H⋯O and C-H⋯π inter-actions.

Related literature

For background and applications to chalcones, see: Jung et al. (2008 ▶); Patil et al. (2007 ▶); Patil & Dharmaprakash (2008 ▶); Prasad et al. (2008 ▶); Schlogl & Egger (1963 ▶). For related structures, see: Ng et al. (2006 ▶); Patil et al. (2006 ▶; 2007 ▶). For on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H17BrO4

M = 377.22

Tetragonal,

a = 26.6517 (3) Å

c = 4.4238 (1) Å

V = 3142.28 (9) Å3

Z = 8

Mo Kα radiation

μ = 2.63 mm−1

T = 100.0 (1) K

0.55 × 0.12 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.320, T max = 0.726

142737 measured reflections

9693 independent reflections

6638 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.097

S = 1.07

9693 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041780/pk2134sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041780/pk2134Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H17BrO4	Dx = 1.595 Mg m−3
Mr = 377.22	Melting point = 403–404 K
Tetragonal, P42/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 4bc	Cell parameters from 9693 reflections
a = 26.6517 (3) Å	θ = 1.1–40.0°
c = 4.4238 (1) Å	µ = 2.63 mm−1
V = 3142.28 (9) Å3	T = 100 K
Z = 8	Block, colorless
F(000) = 1536	0.55 × 0.12 × 0.12 mm

Bruker SMART APEXII CCD area-detector diffractometer	9693 independent reflections
Radiation source: fine-focus sealed tube	6638 reflections with I > 2σ(I)
graphite	Rint = 0.062
Detector resolution: 8.33 pixels mm-1	θmax = 40.0°, θmin = 1.1°
ω scans	h = −41→48
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −48→44
Tmin = 0.320, Tmax = 0.726	l = −7→7
142737 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.774P] where P = (Fo2 + 2Fc2)/3
9693 reflections	(Δ/σ)max = 0.003
211 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Experimental. The low-temperature data was collected with the Oxford Cryosystem 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. Data up to 2theta = 80 degrees is used in the final refinement

	x	y	z	Uiso*/Ueq
Br1	0.332148 (4)	0.255150 (5)	−0.02867 (3)	0.01727 (4)
O1	0.44846 (4)	0.45051 (4)	0.6855 (3)	0.02383 (19)
O2	0.71139 (3)	0.49941 (3)	1.1449 (2)	0.01727 (16)
O3	0.76246 (3)	0.42445 (3)	0.88670 (19)	0.01535 (15)
O4	0.71518 (3)	0.34984 (3)	0.5922 (2)	0.01822 (16)
C1	0.44558 (5)	0.32060 (5)	0.4779 (3)	0.0174 (2)
H1A	0.4729	0.3097	0.5908	0.021*
C2	0.41434 (4)	0.28571 (4)	0.3389 (3)	0.0167 (2)
H2A	0.4201	0.2515	0.3625	0.020*
C3	0.37450 (4)	0.30249 (4)	0.1647 (3)	0.01471 (19)
C4	0.36484 (4)	0.35344 (4)	0.1273 (3)	0.01654 (19)
H4A	0.3383	0.3642	0.0071	0.020*
C5	0.39549 (4)	0.38788 (4)	0.2725 (3)	0.01630 (19)
H5A	0.3890	0.4220	0.2523	0.020*
C6	0.43604 (4)	0.37201 (5)	0.4488 (3)	0.01541 (19)
C7	0.46729 (4)	0.41065 (5)	0.6074 (3)	0.0169 (2)
C8	0.52093 (4)	0.39895 (5)	0.6544 (3)	0.0179 (2)
H8A	0.5337	0.3689	0.5811	0.022*
C9	0.55163 (4)	0.43071 (5)	0.8004 (3)	0.0167 (2)
H9A	0.5369	0.4586	0.8901	0.020*
C10	0.60602 (4)	0.42570 (4)	0.8320 (3)	0.01485 (19)
C11	0.63128 (4)	0.46298 (4)	0.9952 (3)	0.01516 (19)
H11A	0.6132	0.4878	1.0950	0.018*
C12	0.68354 (4)	0.46278 (4)	1.0079 (2)	0.01394 (18)
C13	0.71100 (4)	0.42475 (4)	0.8662 (3)	0.01360 (18)
C14	0.68527 (4)	0.38623 (4)	0.7139 (3)	0.01435 (18)
C15	0.63325 (4)	0.38689 (4)	0.6936 (3)	0.01565 (19)
H15A	0.6165	0.3617	0.5887	0.019*
C16	0.68428 (5)	0.53482 (5)	1.3242 (3)	0.0180 (2)
H16A	0.7073	0.5587	1.4098	0.027*
H16B	0.6670	0.5175	1.4837	0.027*
H16C	0.6604	0.5521	1.1996	0.027*
C17	0.78718 (5)	0.43783 (5)	0.6083 (3)	0.0191 (2)
H17A	0.8228	0.4337	0.6311	0.029*
H17B	0.7799	0.4722	0.5601	0.029*
H17C	0.7754	0.4165	0.4485	0.029*
C18	0.69070 (5)	0.31032 (5)	0.4311 (3)	0.0198 (2)
H18A	0.7153	0.2866	0.3617	0.030*
H18B	0.6731	0.3241	0.2608	0.030*
H18C	0.6673	0.2938	0.5625	0.030*

	U11	U22	U33	U12	U13	U23
Br1	0.01487 (6)	0.01441 (6)	0.02252 (6)	−0.00131 (4)	−0.00146 (4)	−0.00109 (4)
O1	0.0156 (4)	0.0196 (4)	0.0364 (5)	0.0027 (3)	−0.0021 (4)	−0.0084 (4)
O2	0.0142 (4)	0.0161 (4)	0.0215 (4)	−0.0018 (3)	−0.0011 (3)	−0.0040 (3)
O3	0.0099 (3)	0.0223 (4)	0.0138 (3)	0.0010 (3)	−0.0009 (3)	0.0006 (3)
O4	0.0127 (4)	0.0169 (4)	0.0250 (4)	0.0019 (3)	−0.0016 (3)	−0.0061 (3)
C1	0.0148 (5)	0.0171 (5)	0.0204 (5)	0.0026 (4)	−0.0025 (4)	−0.0007 (4)
C2	0.0168 (5)	0.0140 (5)	0.0193 (5)	0.0026 (4)	−0.0012 (4)	0.0000 (4)
C3	0.0123 (4)	0.0145 (5)	0.0174 (5)	−0.0013 (3)	0.0011 (4)	−0.0005 (4)
C4	0.0132 (5)	0.0153 (5)	0.0211 (5)	0.0012 (4)	−0.0019 (4)	0.0017 (4)
C5	0.0131 (5)	0.0137 (5)	0.0221 (5)	0.0012 (4)	−0.0009 (4)	0.0008 (4)
C6	0.0115 (4)	0.0165 (5)	0.0182 (5)	0.0005 (4)	0.0003 (4)	−0.0012 (4)
C7	0.0120 (5)	0.0179 (5)	0.0209 (5)	0.0003 (4)	−0.0006 (4)	−0.0018 (4)
C8	0.0121 (5)	0.0186 (5)	0.0231 (5)	0.0014 (4)	−0.0007 (4)	−0.0040 (4)
C9	0.0122 (5)	0.0158 (5)	0.0220 (5)	0.0004 (4)	0.0002 (4)	−0.0014 (4)
C10	0.0115 (4)	0.0145 (5)	0.0185 (5)	−0.0001 (3)	−0.0003 (3)	0.0001 (4)
C11	0.0124 (4)	0.0141 (5)	0.0190 (5)	−0.0002 (3)	0.0000 (4)	0.0001 (4)
C12	0.0130 (4)	0.0133 (4)	0.0156 (4)	−0.0011 (3)	−0.0005 (3)	0.0007 (3)
C13	0.0110 (4)	0.0156 (5)	0.0143 (4)	0.0000 (3)	−0.0008 (3)	0.0007 (3)
C14	0.0130 (4)	0.0137 (4)	0.0163 (4)	0.0014 (3)	−0.0008 (3)	−0.0003 (4)
C15	0.0131 (5)	0.0147 (5)	0.0191 (5)	0.0000 (4)	−0.0013 (4)	−0.0015 (4)
C16	0.0196 (5)	0.0159 (5)	0.0186 (5)	0.0003 (4)	−0.0014 (4)	−0.0019 (4)
C17	0.0148 (5)	0.0258 (6)	0.0168 (5)	−0.0009 (4)	0.0009 (4)	0.0024 (4)
C18	0.0170 (5)	0.0165 (5)	0.0259 (6)	0.0002 (4)	−0.0004 (4)	−0.0051 (4)

Br1—C3	1.8967 (11)	C8—H8A	0.9300
O1—C7	1.2247 (15)	C9—C10	1.4624 (16)
O2—C12	1.3678 (14)	C9—H9A	0.9300
O2—C16	1.4292 (15)	C10—C11	1.4007 (16)
O3—C13	1.3746 (13)	C10—C15	1.4039 (16)
O3—C17	1.4413 (15)	C11—C12	1.3941 (16)
O4—C14	1.3658 (14)	C11—H11A	0.9300
O4—C18	1.4294 (15)	C12—C13	1.3984 (16)
C1—C2	1.3916 (17)	C13—C14	1.4065 (16)
C1—C6	1.3997 (17)	C14—C15	1.3894 (16)
C1—H1A	0.9300	C15—H15A	0.9300
C2—C3	1.3862 (16)	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.3917 (16)	C16—H16C	0.9600
C4—C5	1.3866 (17)	C17—H17A	0.9600
C4—H4A	0.9300	C17—H17B	0.9600
C5—C6	1.3981 (16)	C17—H17C	0.9600
C5—H5A	0.9300	C18—H18A	0.9600
C6—C7	1.4990 (17)	C18—H18B	0.9600
C7—C8	1.4777 (16)	C18—H18C	0.9600
C8—C9	1.3428 (17)
C12—O2—C16	116.30 (9)	C12—C11—C10	119.88 (11)
C13—O3—C17	113.47 (9)	C12—C11—H11A	120.1
C14—O4—C18	116.97 (9)	C10—C11—H11A	120.1
C2—C1—C6	120.31 (11)	O2—C12—C11	123.86 (11)
C2—C1—H1A	119.8	O2—C12—C13	115.59 (10)
C6—C1—H1A	119.8	C11—C12—C13	120.51 (10)
C3—C2—C1	119.24 (11)	O3—C13—C12	119.79 (10)
C3—C2—H2A	120.4	O3—C13—C14	120.92 (10)
C1—C2—H2A	120.4	C12—C13—C14	119.25 (10)
C2—C3—C4	121.50 (11)	O4—C14—C15	124.47 (10)
C2—C3—Br1	119.46 (9)	O4—C14—C13	115.00 (10)
C4—C3—Br1	119.04 (9)	C15—C14—C13	120.54 (10)
C5—C4—C3	118.81 (11)	C14—C15—C10	119.81 (11)
C5—C4—H4A	120.6	C14—C15—H15A	120.1
C3—C4—H4A	120.6	C10—C15—H15A	120.1
C4—C5—C6	120.89 (11)	O2—C16—H16A	109.5
C4—C5—H5A	119.6	O2—C16—H16B	109.5
C6—C5—H5A	119.6	H16A—C16—H16B	109.5
C5—C6—C1	119.21 (11)	O2—C16—H16C	109.5
C5—C6—C7	118.87 (11)	H16A—C16—H16C	109.5
C1—C6—C7	121.89 (11)	H16B—C16—H16C	109.5
O1—C7—C8	122.66 (11)	O3—C17—H17A	109.5
O1—C7—C6	120.02 (11)	O3—C17—H17B	109.5
C8—C7—C6	117.29 (10)	H17A—C17—H17B	109.5
C9—C8—C7	121.62 (11)	O3—C17—H17C	109.5
C9—C8—H8A	119.2	H17A—C17—H17C	109.5
C7—C8—H8A	119.2	H17B—C17—H17C	109.5
C8—C9—C10	126.33 (11)	O4—C18—H18A	109.5
C8—C9—H9A	116.8	O4—C18—H18B	109.5
C10—C9—H9A	116.8	H18A—C18—H18B	109.5
C11—C10—C15	119.93 (10)	O4—C18—H18C	109.5
C11—C10—C9	117.44 (10)	H18A—C18—H18C	109.5
C15—C10—C9	122.55 (10)	H18B—C18—H18C	109.5
C6—C1—C2—C3	1.71 (18)	C16—O2—C12—C11	10.38 (16)
C1—C2—C3—C4	−0.42 (18)	C16—O2—C12—C13	−171.99 (10)
C1—C2—C3—Br1	179.40 (9)	C10—C11—C12—O2	175.59 (11)
C2—C3—C4—C5	−1.05 (18)	C10—C11—C12—C13	−1.93 (17)
Br1—C3—C4—C5	179.12 (9)	C17—O3—C13—C12	−107.90 (12)
C3—C4—C5—C6	1.25 (18)	C17—O3—C13—C14	74.48 (14)
C4—C5—C6—C1	0.01 (18)	O2—C12—C13—O3	3.79 (15)
C4—C5—C6—C7	−178.49 (11)	C11—C12—C13—O3	−178.50 (10)
C2—C1—C6—C5	−1.51 (18)	O2—C12—C13—C14	−178.55 (10)
C2—C1—C6—C7	176.94 (11)	C11—C12—C13—C14	−0.84 (17)
C5—C6—C7—O1	28.97 (18)	C18—O4—C14—C15	0.71 (17)
C1—C6—C7—O1	−149.50 (13)	C18—O4—C14—C13	−179.04 (11)
C5—C6—C7—C8	−149.21 (12)	O3—C13—C14—O4	−0.08 (16)
C1—C6—C7—C8	32.33 (17)	C12—C13—C14—O4	−177.72 (10)
O1—C7—C8—C9	3.4 (2)	O3—C13—C14—C15	−179.84 (10)
C6—C7—C8—C9	−178.44 (12)	C12—C13—C14—C15	2.53 (17)
C7—C8—C9—C10	−173.04 (12)	O4—C14—C15—C10	178.83 (11)
C8—C9—C10—C11	−179.68 (12)	C13—C14—C15—C10	−1.43 (18)
C8—C9—C10—C15	3.6 (2)	C11—C10—C15—C14	−1.35 (18)
C15—C10—C11—C12	3.03 (17)	C9—C10—C15—C14	175.30 (11)
C9—C10—C11—C12	−173.80 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1i	0.93	2.52	3.4391 (16)	170
C17—H17C···O3ii	0.96	2.52	3.2789 (16)	136
C16—H16B···Cg1iii	0.96	2.97	3.8080 (14)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1i	0.93	2.52	3.4391 (16)	170
C17—H17C⋯O3ii	0.96	2.52	3.2789 (16)	136
C16—H16B⋯Cg1iii	0.96	2.97	3.8080 (14)	147

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C10–C15 ring.