(E)-1-(5-Iodo-thio-phen-2-yl)-3-(3,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

In the title compound, C(16)H(15)IO(4)S, the dihedral angle between the thio-phene and benzene rings is 11.50 (2)°. The methoxy O atoms deviate by 0.0060 (2), -0.1319 (2) and 0.0426 (2) Å from the phenyl ring plane. The crystal packing features C-H⋯O hydrogen bonds, which link the molecules into C(11) chains propagating in [100xxx].

Related literature

For the biological activity of chalcones, see: Di Carlo et al. (1999 ▶); Lin et al. (2002 ▶). For a related structure, see Ranjith et al. (2010 ▶).

Experimental

Crystal data

C16H15IO4S

M = 430.25

Orthorhombic,

a = 17.2328 (12) Å

b = 8.1885 (6) Å

c = 23.7049 (17) Å

V = 3345.0 (4) Å3

Z = 8

Mo Kα radiation

μ = 2.05 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.578, T max = 0.684

17211 measured reflections

4092 independent reflections

3263 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.062

S = 1.06

4092 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP 3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038226/bt6834sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038226/bt6834Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038226/bt6834Isup3.cml

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

C16H15IO4S	F(000) = 1696
Mr = 430.25	Dx = 1.709 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4092 reflections
a = 17.2328 (12) Å	θ = 1.7–28.2°
b = 8.1885 (6) Å	µ = 2.05 mm−1
c = 23.7049 (17) Å	T = 293 K
V = 3345.0 (4) Å3	Block, colourless
Z = 8	0.30 × 0.25 × 0.20 mm

Bruker APEXII area-detector diffractometer	4092 independent reflections
Radiation source: fine-focus sealed tube	3263 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω and φ scans	θmax = 28.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −22→12
Tmin = 0.578, Tmax = 0.684	k = −8→10
17211 measured reflections	l = −25→31

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0255P)2 + 1.7451P] where P = (Fo2 + 2Fc2)/3
4092 reflections	(Δ/σ)max = 0.003
202 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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 > 2sigma(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
I1	0.772746 (8)	0.12196 (2)	0.038840 (8)	0.04680 (7)
S1	0.58646 (3)	0.18751 (8)	0.02816 (2)	0.04050 (13)
O3	0.06960 (10)	−0.0979 (2)	0.24845 (7)	0.0542 (5)
O2	0.21744 (11)	−0.1501 (3)	0.27590 (8)	0.0596 (5)
O1	0.41760 (9)	0.2434 (2)	0.02460 (7)	0.0520 (4)
O4	0.02969 (9)	0.0186 (3)	0.14688 (8)	0.0567 (5)
C8	0.24287 (13)	0.0457 (3)	0.13714 (9)	0.0390 (5)
C13	0.51699 (12)	0.1111 (3)	0.07348 (9)	0.0351 (5)
C5	0.12645 (14)	−0.0588 (3)	0.21007 (9)	0.0409 (5)
C4	0.10723 (13)	0.0096 (3)	0.15811 (10)	0.0407 (5)
C10	0.30318 (13)	0.1074 (3)	0.09885 (10)	0.0412 (5)
H10	0.2866	0.1721	0.0690	0.049*
C7	0.26207 (13)	−0.0265 (3)	0.18831 (9)	0.0417 (5)
H7	0.3139	−0.0397	0.1982	0.050*
C15	0.63199 (13)	0.0081 (3)	0.10998 (10)	0.0422 (5)
H15	0.6634	−0.0502	0.1347	0.051*
C16	0.65890 (12)	0.0932 (3)	0.06498 (10)	0.0363 (5)
C14	0.55074 (13)	0.0186 (3)	0.11476 (9)	0.0402 (5)
H14	0.5227	−0.0324	0.1433	0.048*
C6	0.20423 (15)	−0.0790 (3)	0.22465 (9)	0.0421 (5)
C9	0.16523 (13)	0.0637 (3)	0.12198 (10)	0.0418 (5)
H9	0.1523	0.1118	0.0877	0.050*
C11	0.37838 (13)	0.0804 (3)	0.10249 (10)	0.0425 (5)
H11	0.3963	0.0124	0.1311	0.051*
C12	0.43547 (13)	0.1525 (3)	0.06352 (10)	0.0384 (5)
C3	0.00578 (16)	0.0851 (4)	0.09421 (12)	0.0601 (7)
H3A	0.0247	0.1949	0.0908	0.090*
H3B	−0.0499	0.0852	0.0922	0.090*
H3C	0.0264	0.0199	0.0641	0.090*
C1	0.2956 (2)	−0.1641 (5)	0.29405 (13)	0.0774 (10)
H1A	0.3240	−0.2302	0.2678	0.116*
H1B	0.2970	−0.2141	0.3307	0.116*
H1C	0.3186	−0.0575	0.2960	0.116*
C2	0.0342 (2)	−0.2524 (4)	0.24123 (16)	0.0881 (12)
H2A	0.0099	−0.2572	0.2048	0.132*
H2B	−0.0041	−0.2684	0.2701	0.132*
H2C	0.0729	−0.3363	0.2439	0.132*

	U11	U22	U33	U12	U13	U23
I1	0.02665 (9)	0.04840 (11)	0.06536 (12)	−0.00074 (6)	0.00204 (7)	−0.00160 (8)
S1	0.0274 (3)	0.0511 (3)	0.0430 (3)	−0.0001 (2)	0.0009 (2)	0.0131 (3)
O3	0.0510 (10)	0.0671 (12)	0.0447 (9)	−0.0104 (9)	0.0219 (8)	−0.0070 (9)
O2	0.0588 (12)	0.0806 (14)	0.0393 (9)	0.0107 (10)	0.0099 (8)	0.0124 (9)
O1	0.0302 (8)	0.0679 (11)	0.0580 (10)	−0.0010 (8)	−0.0014 (7)	0.0209 (9)
O4	0.0311 (9)	0.0854 (14)	0.0537 (10)	−0.0024 (9)	0.0062 (7)	0.0030 (10)
C8	0.0313 (11)	0.0469 (14)	0.0387 (11)	−0.0043 (10)	0.0050 (9)	−0.0018 (11)
C13	0.0301 (10)	0.0406 (12)	0.0347 (10)	−0.0029 (9)	0.0028 (8)	0.0021 (10)
C5	0.0411 (12)	0.0431 (12)	0.0384 (11)	−0.0027 (10)	0.0139 (10)	−0.0068 (10)
C4	0.0324 (11)	0.0482 (13)	0.0413 (12)	−0.0019 (10)	0.0072 (9)	−0.0078 (10)
C10	0.0324 (11)	0.0512 (14)	0.0398 (12)	−0.0052 (10)	0.0022 (9)	0.0034 (11)
C7	0.0333 (12)	0.0531 (15)	0.0388 (11)	0.0007 (10)	0.0037 (9)	−0.0032 (11)
C15	0.0353 (12)	0.0503 (14)	0.0411 (12)	0.0051 (10)	−0.0052 (9)	0.0055 (11)
C16	0.0263 (10)	0.0400 (12)	0.0425 (12)	0.0002 (9)	−0.0035 (9)	−0.0044 (10)
C14	0.0364 (12)	0.0489 (14)	0.0352 (11)	−0.0006 (10)	0.0033 (9)	0.0064 (10)
C6	0.0490 (13)	0.0455 (13)	0.0318 (11)	0.0042 (11)	0.0071 (10)	−0.0035 (10)
C9	0.0369 (12)	0.0500 (13)	0.0384 (12)	−0.0013 (10)	0.0043 (9)	0.0022 (11)
C11	0.0340 (12)	0.0531 (14)	0.0404 (12)	−0.0008 (10)	0.0033 (9)	0.0054 (11)
C12	0.0300 (11)	0.0445 (13)	0.0405 (11)	−0.0030 (9)	0.0000 (9)	−0.0003 (10)
C3	0.0392 (14)	0.0727 (19)	0.0684 (18)	0.0050 (13)	−0.0044 (13)	0.0029 (15)
C1	0.070 (2)	0.111 (3)	0.0507 (16)	0.024 (2)	0.0007 (15)	0.0221 (18)
C2	0.099 (3)	0.076 (2)	0.089 (2)	−0.034 (2)	0.044 (2)	−0.0086 (19)

I1—C16	2.071 (2)	C10—H10	0.9300
S1—C16	1.708 (2)	C7—C6	1.386 (3)
S1—C13	1.726 (2)	C7—H7	0.9300
O3—C5	1.375 (3)	C15—C16	1.356 (3)
O3—C2	1.414 (3)	C15—C14	1.407 (3)
O2—C6	1.366 (3)	C15—H15	0.9300
O2—C1	1.418 (4)	C14—H14	0.9300
O1—C12	1.225 (3)	C9—H9	0.9300
O4—C4	1.364 (3)	C11—C12	1.473 (3)
O4—C3	1.423 (3)	C11—H11	0.9300
C8—C7	1.390 (3)	C3—H3A	0.9600
C8—C9	1.393 (3)	C3—H3B	0.9600
C8—C10	1.469 (3)	C3—H3C	0.9600
C13—C14	1.367 (3)	C1—H1A	0.9600
C13—C12	1.464 (3)	C1—H1B	0.9600
C5—C4	1.393 (3)	C1—H1C	0.9600
C5—C6	1.394 (4)	C2—H2A	0.9600
C4—C9	1.389 (3)	C2—H2B	0.9600
C10—C11	1.317 (3)	C2—H2C	0.9600
C16—S1—C13	91.44 (11)	O2—C6—C7	124.4 (2)
C5—O3—C2	115.8 (2)	O2—C6—C5	115.6 (2)
C6—O2—C1	117.5 (2)	C7—C6—C5	120.0 (2)
C4—O4—C3	118.39 (19)	C4—C9—C8	119.9 (2)
C7—C8—C9	119.9 (2)	C4—C9—H9	120.1
C7—C8—C10	121.1 (2)	C8—C9—H9	120.1
C9—C8—C10	118.9 (2)	C10—C11—C12	123.3 (2)
C14—C13—C12	130.7 (2)	C10—C11—H11	118.4
C14—C13—S1	110.55 (16)	C12—C11—H11	118.4
C12—C13—S1	118.78 (16)	O1—C12—C13	120.2 (2)
O3—C5—C4	120.6 (2)	O1—C12—C11	123.2 (2)
O3—C5—C6	119.6 (2)	C13—C12—C11	116.6 (2)
C4—C5—C6	119.7 (2)	O4—C3—H3A	109.5
O4—C4—C9	124.6 (2)	O4—C3—H3B	109.5
O4—C4—C5	115.3 (2)	H3A—C3—H3B	109.5
C9—C4—C5	120.2 (2)	O4—C3—H3C	109.5
C11—C10—C8	126.7 (2)	H3A—C3—H3C	109.5
C11—C10—H10	116.6	H3B—C3—H3C	109.5
C8—C10—H10	116.6	O2—C1—H1A	109.5
C6—C7—C8	120.2 (2)	O2—C1—H1B	109.5
C6—C7—H7	119.9	H1A—C1—H1B	109.5
C8—C7—H7	119.9	O2—C1—H1C	109.5
C16—C15—C14	111.8 (2)	H1A—C1—H1C	109.5
C16—C15—H15	124.1	H1B—C1—H1C	109.5
C14—C15—H15	124.1	O3—C2—H2A	109.5
C15—C16—S1	112.61 (17)	O3—C2—H2B	109.5
C15—C16—I1	128.15 (17)	H2A—C2—H2B	109.5
S1—C16—I1	119.23 (12)	O3—C2—H2C	109.5
C13—C14—C15	113.6 (2)	H2A—C2—H2C	109.5
C13—C14—H14	123.2	H2B—C2—H2C	109.5
C15—C14—H14	123.2
C16—S1—C13—C14	0.39 (18)	C16—C15—C14—C13	0.0 (3)
C16—S1—C13—C12	179.91 (19)	C1—O2—C6—C7	3.0 (4)
C2—O3—C5—C4	84.7 (3)	C1—O2—C6—C5	−176.2 (3)
C2—O3—C5—C6	−99.0 (3)	C8—C7—C6—O2	−179.5 (2)
C3—O4—C4—C9	1.2 (4)	C8—C7—C6—C5	−0.3 (4)
C3—O4—C4—C5	−179.1 (2)	O3—C5—C6—O2	5.0 (3)
O3—C5—C4—O4	−6.1 (3)	C4—C5—C6—O2	−178.7 (2)
C6—C5—C4—O4	177.6 (2)	O3—C5—C6—C7	−174.3 (2)
O3—C5—C4—C9	173.6 (2)	C4—C5—C6—C7	2.0 (4)
C6—C5—C4—C9	−2.7 (4)	O4—C4—C9—C8	−178.7 (2)
C7—C8—C10—C11	11.7 (4)	C5—C4—C9—C8	1.6 (4)
C9—C8—C10—C11	−169.6 (3)	C7—C8—C9—C4	0.2 (4)
C9—C8—C7—C6	−0.8 (4)	C10—C8—C9—C4	−178.6 (2)
C10—C8—C7—C6	177.9 (2)	C8—C10—C11—C12	−177.4 (2)
C14—C15—C16—S1	0.3 (3)	C14—C13—C12—O1	177.4 (2)
C14—C15—C16—I1	179.10 (17)	S1—C13—C12—O1	−2.1 (3)
C13—S1—C16—C15	−0.38 (19)	C14—C13—C12—C11	−2.2 (4)
C13—S1—C16—I1	−179.33 (13)	S1—C13—C12—C11	178.35 (17)
C12—C13—C14—C15	−179.8 (2)	C10—C11—C12—O1	0.1 (4)
S1—C13—C14—C15	−0.3 (3)	C10—C11—C12—C13	179.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O2i	0.93	2.45	3.341 (3)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O2i	0.93	2.45	3.341 (3)	159

Symmetry code: (i) .