(E)-1-(4-Bromo-phen-yl)-3-(2,4,6-trimethoxy-phen-yl)prop-2-en-1-one.

The mol-ecule of the title chalcone derivative, C(18)H(17)BrO(4), is twisted, the dihedral angle between the 4-bromo-phenyl and 2,4,6-trimethoxy-phenyl rings being 39.17 (6)°. The three meth-oxy groups are oriented in two different conformations whereby two meth-oxy groups are coplanar, whereas the third is twisted with respect to the attached benzene ring [C-O-C-C torsion angles of -2.84 (18), -2.80 (18) and -9.31 (18)°]. Weak intra-molecular C-H⋯O inter-actions generate two S(5) and one S(6) ring motifs. In the crystal structure, mol-ecules are linked into supra-molecular sheets parallel to the bc plane by weak C-H⋯O inter-actions. These sheets are stacked along the a axis. The crystal structure is further stabilized by weak C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a related structure, see: Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Fayed & Awad (2004 ▶); Jung et al. (2008 ▶); Patil & Dharmaprakash (2008 ▶); Prasad et al. (2008 ▶); Sens & Drexhage (1981 ▶) and Xu et al. (2005 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C18H17BrO4

M = 377.22

Triclinic,

a = 6.3690 (1) Å

b = 9.2553 (1) Å

c = 14.1884 (2) Å

α = 104.397 (1)°

β = 93.748 (1)°

γ = 98.799 (1)°

V = 795.88 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.60 mm−1

T = 100 K

0.27 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.541, T max = 0.701

16214 measured reflections

4607 independent reflections

4118 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.060

S = 1.02

4607 reflections

276 parameters

All H-atom parameters refined

Δρmax = 0.42 e Å−3

Δρmin = −0.23 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010496/sj2593sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010496/sj2593Isup2.hkl

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

C18H17BrO4	Z = 2
Mr = 377.22	F(000) = 384
Triclinic, P1	Dx = 1.574 Mg m−3
Hall symbol: -P 1	Melting point = 425–426 K
a = 6.3690 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2553 (1) Å	Cell parameters from 4607 reflections
c = 14.1884 (2) Å	θ = 2.3–30.0°
α = 104.397 (1)°	µ = 2.60 mm−1
β = 93.748 (1)°	T = 100 K
γ = 98.799 (1)°	Block, colorless
V = 795.88 (2) Å3	0.27 × 0.20 × 0.15 mm

Bruker APEXII CCD area-detector diffractometer	4607 independent reflections
Radiation source: sealed tube	4118 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.541, Tmax = 0.701	k = −13→13
16214 measured reflections	l = −19→19

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.060	All H-atom parameters refined
S = 1.02	w = 1/[σ2(Fo2) + (0.029P)2 + 0.2809P] where P = (Fo2 + 2Fc2)/3
4607 reflections	(Δ/σ)max = 0.001
276 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
Br1	1.13952 (2)	−0.293272 (16)	0.461372 (11)	0.02616 (5)
O1	0.44064 (16)	−0.15866 (11)	0.80334 (7)	0.0216 (2)
O2	−0.08941 (16)	0.10051 (10)	0.90599 (7)	0.01977 (19)
O3	−0.16385 (15)	0.59990 (10)	0.87549 (7)	0.01789 (18)
O4	0.35439 (15)	0.34158 (10)	0.71793 (7)	0.01744 (18)
C1	0.6621 (2)	−0.08380 (15)	0.59115 (10)	0.0193 (2)
C2	0.8032 (2)	−0.13463 (16)	0.52476 (10)	0.0213 (3)
C3	0.9448 (2)	−0.22219 (14)	0.55005 (10)	0.0184 (2)
C4	0.9487 (2)	−0.25950 (15)	0.63902 (10)	0.0197 (3)
C5	0.8037 (2)	−0.21054 (14)	0.70324 (10)	0.0183 (2)
C6	0.6585 (2)	−0.12259 (13)	0.67994 (9)	0.0153 (2)
C7	0.4967 (2)	−0.07889 (14)	0.74854 (9)	0.0158 (2)
C8	0.4106 (2)	0.06017 (14)	0.74754 (9)	0.0168 (2)
C9	0.2408 (2)	0.08983 (14)	0.79633 (9)	0.0154 (2)
C10	0.13257 (19)	0.21967 (13)	0.81164 (9)	0.0141 (2)
C11	−0.0378 (2)	0.22448 (13)	0.87113 (9)	0.0147 (2)
C12	−0.1436 (2)	0.34794 (14)	0.89404 (9)	0.0155 (2)
C13	−0.0755 (2)	0.47186 (14)	0.85774 (9)	0.0145 (2)
C14	0.0926 (2)	0.47405 (14)	0.79966 (9)	0.0153 (2)
C15	0.19197 (19)	0.34849 (13)	0.77554 (9)	0.0139 (2)
C16	−0.2346 (2)	0.10739 (16)	0.97956 (10)	0.0194 (3)
C17	−0.3435 (2)	0.60468 (16)	0.93123 (10)	0.0196 (3)
C18	0.4171 (2)	0.46747 (15)	0.67761 (11)	0.0198 (3)
H1	0.562 (3)	−0.026 (2)	0.5736 (13)	0.027 (4)*
H2	0.802 (3)	−0.108 (2)	0.4646 (14)	0.029 (5)*
H4	1.047 (3)	−0.321 (2)	0.6562 (13)	0.027 (4)*
H5	0.809 (3)	−0.2327 (19)	0.7633 (13)	0.024 (4)*
H8	0.481 (3)	0.1247 (19)	0.7154 (12)	0.017 (4)*
H9	0.185 (3)	0.0164 (19)	0.8273 (12)	0.021 (4)*
H12	−0.257 (3)	0.3470 (19)	0.9351 (13)	0.022 (4)*
H14	0.134 (3)	0.5637 (19)	0.7793 (12)	0.020 (4)*
H16A	−0.182 (3)	0.1914 (19)	1.0344 (13)	0.022 (4)*
H16B	−0.233 (3)	0.011 (2)	0.9971 (14)	0.030 (5)*
H16C	−0.379 (3)	0.1129 (18)	0.9542 (12)	0.016 (4)*
H17A	−0.383 (3)	0.700 (2)	0.9308 (14)	0.030 (5)*
H17B	−0.455 (3)	0.5210 (19)	0.8990 (12)	0.020 (4)*
H17C	−0.302 (3)	0.6012 (18)	0.9976 (13)	0.020 (4)*
H18A	0.456 (3)	0.561 (2)	0.7289 (14)	0.028 (5)*
H18B	0.535 (3)	0.444 (2)	0.6459 (14)	0.029 (5)*
H18C	0.302 (3)	0.4758 (19)	0.6301 (13)	0.023 (4)*

	U11	U22	U33	U12	U13	U23
Br1	0.02155 (8)	0.02786 (8)	0.02793 (8)	0.00852 (5)	0.00972 (5)	0.00087 (5)
O1	0.0250 (5)	0.0186 (4)	0.0258 (5)	0.0072 (4)	0.0092 (4)	0.0105 (4)
O2	0.0227 (5)	0.0166 (4)	0.0246 (5)	0.0054 (4)	0.0119 (4)	0.0106 (4)
O3	0.0185 (5)	0.0176 (4)	0.0220 (5)	0.0089 (3)	0.0091 (4)	0.0081 (4)
O4	0.0197 (5)	0.0152 (4)	0.0211 (4)	0.0062 (3)	0.0102 (4)	0.0078 (3)
C1	0.0199 (6)	0.0216 (6)	0.0183 (6)	0.0097 (5)	0.0017 (5)	0.0053 (5)
C2	0.0223 (7)	0.0260 (7)	0.0170 (6)	0.0081 (5)	0.0033 (5)	0.0054 (5)
C3	0.0158 (6)	0.0168 (6)	0.0204 (6)	0.0033 (5)	0.0036 (5)	0.0002 (5)
C4	0.0178 (6)	0.0161 (6)	0.0271 (7)	0.0065 (5)	0.0030 (5)	0.0067 (5)
C5	0.0196 (6)	0.0161 (6)	0.0213 (6)	0.0046 (5)	0.0031 (5)	0.0076 (5)
C6	0.0154 (6)	0.0118 (5)	0.0180 (6)	0.0021 (4)	0.0021 (4)	0.0027 (4)
C7	0.0168 (6)	0.0140 (5)	0.0164 (6)	0.0031 (4)	0.0018 (4)	0.0030 (4)
C8	0.0203 (6)	0.0137 (5)	0.0176 (6)	0.0044 (5)	0.0042 (5)	0.0051 (4)
C9	0.0171 (6)	0.0131 (5)	0.0158 (6)	0.0022 (4)	0.0013 (4)	0.0039 (4)
C10	0.0143 (6)	0.0141 (5)	0.0137 (5)	0.0023 (4)	0.0021 (4)	0.0031 (4)
C11	0.0155 (6)	0.0137 (5)	0.0149 (5)	0.0012 (4)	0.0019 (4)	0.0049 (4)
C12	0.0143 (6)	0.0175 (6)	0.0155 (6)	0.0037 (4)	0.0038 (4)	0.0047 (4)
C13	0.0143 (6)	0.0149 (5)	0.0149 (5)	0.0047 (4)	0.0011 (4)	0.0036 (4)
C14	0.0171 (6)	0.0147 (5)	0.0157 (6)	0.0040 (4)	0.0035 (4)	0.0057 (4)
C15	0.0135 (5)	0.0151 (5)	0.0132 (5)	0.0027 (4)	0.0030 (4)	0.0036 (4)
C16	0.0197 (6)	0.0206 (6)	0.0203 (6)	0.0026 (5)	0.0082 (5)	0.0087 (5)
C17	0.0172 (6)	0.0228 (6)	0.0212 (6)	0.0076 (5)	0.0070 (5)	0.0061 (5)
C18	0.0229 (7)	0.0165 (6)	0.0244 (7)	0.0062 (5)	0.0125 (5)	0.0093 (5)

Br1—C3	1.8963 (13)	C8—H8	0.920 (17)
O1—C7	1.2321 (15)	C9—C10	1.4524 (17)
O2—C11	1.3627 (14)	C9—H9	0.936 (17)
O2—C16	1.4351 (15)	C10—C11	1.4171 (17)
O3—C13	1.3634 (15)	C10—C15	1.4205 (16)
O3—C17	1.4326 (16)	C11—C12	1.3943 (17)
O4—C15	1.3591 (14)	C12—C13	1.3927 (17)
O4—C18	1.4364 (15)	C12—H12	0.957 (18)
C1—C2	1.3910 (19)	C13—C14	1.3937 (17)
C1—C6	1.3939 (18)	C14—C15	1.3870 (17)
C1—H1	0.953 (18)	C14—H14	0.950 (17)
C2—C3	1.388 (2)	C16—H16A	0.953 (18)
C2—H2	0.943 (19)	C16—H16B	0.985 (19)
C3—C4	1.3888 (19)	C16—H16C	0.980 (17)
C4—C5	1.3858 (19)	C17—H17A	0.956 (18)
C4—H4	0.965 (18)	C17—H17B	0.961 (17)
C5—C6	1.3969 (18)	C17—H17C	0.971 (17)
C5—H5	0.924 (18)	C18—H18A	0.971 (19)
C6—C7	1.4954 (17)	C18—H18B	0.93 (2)
C7—C8	1.4768 (17)	C18—H18C	0.987 (18)
C8—C9	1.3486 (18)
C11—O2—C16	118.40 (10)	O2—C11—C12	122.08 (11)
C13—O3—C17	118.06 (10)	O2—C11—C10	115.23 (11)
C15—O4—C18	117.90 (10)	C12—C11—C10	122.69 (11)
C2—C1—C6	121.15 (12)	C13—C12—C11	118.12 (11)
C2—C1—H1	118.8 (11)	C13—C12—H12	121.9 (10)
C6—C1—H1	120.0 (11)	C11—C12—H12	120.0 (10)
C3—C2—C1	118.35 (13)	O3—C13—C12	123.91 (11)
C3—C2—H2	121.6 (11)	O3—C13—C14	114.39 (11)
C1—C2—H2	120.1 (11)	C12—C13—C14	121.70 (11)
C2—C3—C4	121.82 (13)	C15—C14—C13	119.29 (11)
C2—C3—Br1	119.49 (10)	C15—C14—H14	123.6 (10)
C4—C3—Br1	118.70 (10)	C13—C14—H14	117.1 (10)
C5—C4—C3	118.94 (12)	O4—C15—C14	122.54 (11)
C5—C4—H4	119.5 (11)	O4—C15—C10	115.72 (10)
C3—C4—H4	121.5 (11)	C14—C15—C10	121.72 (11)
C4—C5—C6	120.70 (12)	O2—C16—H16A	110.1 (11)
C4—C5—H5	118.9 (11)	O2—C16—H16B	102.7 (11)
C6—C5—H5	120.4 (11)	H16A—C16—H16B	110.8 (15)
C1—C6—C5	119.01 (12)	O2—C16—H16C	112.1 (10)
C1—C6—C7	121.73 (11)	H16A—C16—H16C	110.4 (14)
C5—C6—C7	119.20 (11)	H16B—C16—H16C	110.5 (14)
O1—C7—C8	122.63 (12)	O3—C17—H17A	103.5 (11)
O1—C7—C6	119.49 (11)	O3—C17—H17B	108.7 (10)
C8—C7—C6	117.87 (11)	H17A—C17—H17B	112.0 (15)
C9—C8—C7	119.33 (11)	O3—C17—H17C	110.5 (10)
C9—C8—H8	123.4 (10)	H17A—C17—H17C	110.8 (15)
C7—C8—H8	117.2 (10)	H17B—C17—H17C	111.1 (14)
C8—C9—C10	130.75 (12)	O4—C18—H18A	111.0 (11)
C8—C9—H9	115.1 (11)	O4—C18—H18B	104.2 (11)
C10—C9—H9	114.1 (11)	H18A—C18—H18B	110.1 (15)
C11—C10—C15	116.44 (11)	O4—C18—H18C	110.9 (10)
C11—C10—C9	118.69 (11)	H18A—C18—H18C	110.4 (15)
C15—C10—C9	124.78 (11)	H18B—C18—H18C	110.0 (15)
C6—C1—C2—C3	−1.6 (2)	C15—C10—C11—O2	−179.05 (11)
C1—C2—C3—C4	0.0 (2)	C9—C10—C11—O2	−2.38 (17)
C1—C2—C3—Br1	−179.94 (10)	C15—C10—C11—C12	−0.09 (18)
C2—C3—C4—C5	1.4 (2)	C9—C10—C11—C12	176.58 (12)
Br1—C3—C4—C5	−178.66 (10)	O2—C11—C12—C13	177.93 (11)
C3—C4—C5—C6	−1.2 (2)	C10—C11—C12—C13	−0.96 (19)
C2—C1—C6—C5	1.8 (2)	C17—O3—C13—C12	−2.84 (18)
C2—C1—C6—C7	−175.19 (12)	C17—O3—C13—C14	177.45 (11)
C4—C5—C6—C1	−0.4 (2)	C11—C12—C13—O3	−179.38 (11)
C4—C5—C6—C7	176.71 (12)	C11—C12—C13—C14	0.31 (19)
C1—C6—C7—O1	151.49 (13)	O3—C13—C14—C15	−178.89 (11)
C5—C6—C7—O1	−25.51 (18)	C12—C13—C14—C15	1.40 (19)
C1—C6—C7—C8	−28.65 (18)	C18—O4—C15—C14	−2.80 (18)
C5—C6—C7—C8	154.35 (12)	C18—O4—C15—C10	178.51 (11)
O1—C7—C8—C9	−10.8 (2)	C13—C14—C15—O4	178.88 (11)
C6—C7—C8—C9	169.35 (12)	C13—C14—C15—C10	−2.52 (19)
C7—C8—C9—C10	176.36 (12)	C11—C10—C15—O4	−179.45 (10)
C8—C9—C10—C11	−176.74 (13)	C9—C10—C15—O4	4.10 (18)
C8—C9—C10—C15	−0.4 (2)	C11—C10—C15—C14	1.86 (18)
C16—O2—C11—C12	−9.31 (18)	C9—C10—C15—C14	−174.59 (12)
C16—O2—C11—C10	169.65 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3i	0.925 (18)	2.497 (18)	3.3572 (17)	154.9 (15)
C8—H8···O4	0.920 (18)	2.268 (18)	2.8103 (16)	117.2 (14)
C9—H9···O1	0.936 (18)	2.449 (19)	2.8128 (17)	103.1 (13)
C9—H9···O2	0.936 (18)	2.269 (19)	2.6960 (16)	107.1 (14)
C18—H18A···O1ii	0.968 (19)	2.566 (19)	3.4518 (18)	152.1 (15)
C17—H17C···Cg1iii	0.971 (17)	2.754 (18)	3.6601 (14)	155.6 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3i	0.925 (18)	2.497 (18)	3.3572 (17)	154.9 (15)
C8—H8⋯O4	0.920 (18)	2.268 (18)	2.8103 (16)	117.2 (14)
C9—H9⋯O1	0.936 (18)	2.449 (19)	2.8128 (17)	103.1 (13)
C9—H9⋯O2	0.936 (18)	2.269 (19)	2.6960 (16)	107.1 (14)
C18—H18A⋯O1ii	0.968 (19)	2.566 (19)	3.4518 (18)	152.1 (15)
C17—H17C⋯Cg1iii	0.971 (17)	2.754 (18)	3.6601 (14)	155.6 (14)

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