(2E)-1-(5-Chloro­thio­phen-2-yl)-3-(2,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one

Prabhu, A.N.; Jayarama, A.; Row, T.N.G.; Upadhyaya, V.

doi:10.1107/S1600536811028236

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2086

doi:10.1107/S1600536811028236

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(2E)-1-(5-Chlorothiophen-2-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

A. N. Prabhu,^a A. Jayarama,^b T. N. Guru Row ^c and V. Upadhyaya ^a ^*

^aPhysics Department, Manipal Institute of Technology, Manipal University, Manipal 576 104, India, ^bDepartment of Physics, Mangalore Institute of Technology & Engineering (MITE), Badagamijar, Moodabidri, Karnataka, India, and ^cSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, India
^*Correspondence e-mail: v.upadhyaya@manipal.edu

(Received 13 June 2011; accepted 14 July 2011; online 23 July 2011)

In the title molecule, C₁₆H₁₅ClO₄S, the chlorothiophene and trimethoxyphenyl rings make a dihedral angle of 31.12 (5)°. The C=C double bond exhibits an E conformation. In the crystal, C—H⋯O interactions generate bifurcated bonds, linking the molecules into chains along the b axis.

Related literature

For general background to chalcones, see: Tomazela et al. (2000 ); Uchida et al. (1998 ); Zyss & Chemla (1987 ). For related structures, see: Benmekhbi et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₅ClO₄S
M_r = 338.79
Monoclinic, P 2₁ /c
a = 18.2795 (12) Å
b = 9.0393 (7) Å
c = 9.8673 (6) Å
β = 99.390 (4)°
V = 1608.57 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 296 K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.928, T_max = 0.935
11590 measured reflections
4590 independent reflections
1621 reflections with I > 2σ(I)
R_int = 0.065

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.197
S = 0.94
4590 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.93	2.71	3.476 (4)	140
C6—H6⋯O1ⁱ	0.93	2.68	3.597 (5)	169
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1999 ); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811028236/pv2418sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028236/pv2418Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811028236/pv2418Isup3.cml

checkCIF report

Comment top

Chalcones represent one of the most abundant and ubiquitous group of natural products (Tomazela et al., 2000). Recently, it has been noted that, among many organic compounds reported for their second harmonic generation, chalcone derivatives are known for their excellent blue light transmittance and good crystallizability (Uchida et al., 1998). The title compound is found to be of interest as an organic non-linear optical material (Zyss & Chemla, 1987).

In the title molecule (Fig. 1), the chlorothiophene and trimethoxyphenyl rings are non-planar with a dihedral angle of 31.12 (5)°. The C═C double bond exhibits an E conformation. In the crystal structure, C—H···O interaction generates H-bonds from two donors, C3 and C6 to the same acceptor, O1 linking the molecules into chains along the c-axis (Fig 2).

Related literature top

For general background to chalcones, see: Tomazela et al. (2000); Uchida et al. (1998); Zyss & Chemla (1987). For related structures, see: Benmekhbi et al. (2009).

Experimental top

To synthesize the title compound, commercially available Analytical Reagent (AR)-grade chemicals were used. 2-Acetyl-5-chlorothiophene (0.01 mol) and 2,4,5-trimethoxybenzaldehyde (0.01 mol) were dissolved in methanol (60 ml). Sodium hydroxide (5 ml, 20%) was then added drop wise to the solution, and stirred for 2 h. The content of the flask were poured into ice-cold water, and the resulting crude solid was collected by filtration. The compound was dried in a hot-air-oven at 323 K and re-crystallized twice from acetone.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. ORTEP (Farrugia, 1999) view of the title compound, showing 50% probability ellipsoids and the atom numbering scheme.
	Fig. 2. A unit cell packing of the title compound showing intermolecular interactions with dotted lines. H-atoms not involved in hydrogen bonding have been excluded.

(2E)-1-(5-Chlorothiophen-2-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₅ClO₄S	F(000) = 704
M_r = 338.79	D_x = 1.399 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4590 reflections
a = 18.2795 (12) Å	θ = 2.3–30.5°
b = 9.0393 (7) Å	µ = 0.38 mm⁻¹
c = 9.8673 (6) Å	T = 296 K
β = 99.390 (4)°	Block, yellow
V = 1608.57 (19) Å³	0.20 × 0.18 × 0.18 mm
Z = 4

Data collection top

Bruker SMART APEX CCD detector diffractometer	4590 independent reflections
Radiation source: fine-focus sealed tube	1621 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.065
ω scans	θ_max = 30.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −26→26
T_min = 0.928, T_max = 0.935	k = −12→12
11590 measured reflections	l = −13→11

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.197	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0776P)²] where P = (F_o² + 2F_c²)/3
4590 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₆H₁₅ClO₄S	V = 1608.57 (19) Å³
M_r = 338.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.2795 (12) Å	µ = 0.38 mm⁻¹
b = 9.0393 (7) Å	T = 296 K
c = 9.8673 (6) Å	0.20 × 0.18 × 0.18 mm
β = 99.390 (4)°

Data collection top

Bruker SMART APEX CCD detector diffractometer	4590 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1621 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.935	R_int = 0.065
11590 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.197	H-atom parameters constrained
S = 0.94	Δρ_max = 0.39 e Å⁻³
4590 reflections	Δρ_min = −0.32 e Å⁻³
202 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl1	1.19089 (6)	0.43556 (14)	0.13180 (12)	0.0853 (4)
S1	1.03627 (5)	0.43686 (11)	0.18651 (10)	0.0602 (3)
O1	0.88221 (14)	0.3967 (3)	0.2335 (3)	0.0681 (8)
O2	0.66429 (13)	0.1207 (3)	0.2390 (3)	0.0726 (8)
O3	0.55841 (13)	−0.2151 (3)	−0.1240 (3)	0.0709 (8)
O4	0.66030 (14)	−0.1426 (3)	−0.2658 (3)	0.0810 (9)
C1	1.10339 (19)	0.3619 (4)	0.1052 (4)	0.0596 (10)
C2	1.0792 (2)	0.2480 (5)	0.0231 (4)	0.0704 (12)
H2	1.1088	0.1949	−0.0279	0.085*
C3	1.00321 (19)	0.2181 (4)	0.0233 (4)	0.0547 (9)
H3	0.9770	0.1434	−0.0282	0.066*
C4	0.97267 (17)	0.3111 (4)	0.1075 (3)	0.0489 (9)
C5	0.89668 (19)	0.3155 (4)	0.1409 (4)	0.0553 (10)
C6	0.84197 (18)	0.2173 (4)	0.0627 (4)	0.0539 (9)
H6	0.8521	0.1744	−0.0179	0.065*
C7	0.77806 (18)	0.1879 (4)	0.1045 (4)	0.0537 (9)
H7	0.7700	0.2364	0.1839	0.064*
C8	0.71877 (17)	0.0894 (4)	0.0419 (4)	0.0474 (9)
C9	0.71853 (19)	0.0245 (4)	−0.0852 (4)	0.0520 (9)
H9	0.7561	0.0484	−0.1348	0.062*
C10	0.66447 (19)	−0.0742 (4)	−0.1407 (4)	0.0555 (10)
C11	0.60855 (18)	−0.1124 (4)	−0.0638 (4)	0.0535 (10)
C12	0.60767 (18)	−0.0500 (4)	0.0619 (4)	0.0541 (10)
H12	0.5708	−0.0757	0.1123	0.065*
C13	0.66189 (18)	0.0522 (4)	0.1149 (4)	0.0516 (9)
C14	0.6146 (2)	0.0767 (5)	0.3268 (4)	0.0876 (15)
H14A	0.5646	0.0937	0.2821	0.131*
H14C	0.6240	0.1331	0.4102	0.131*
H14B	0.6213	−0.0266	0.3477	0.131*
C15	0.5106 (2)	−0.2793 (4)	−0.0396 (5)	0.0771 (13)
H15C	0.5398	−0.3263	0.0383	0.116*
H15A	0.4792	−0.3515	−0.0916	0.116*
H15B	0.4805	−0.2034	−0.0084	0.116*
C16	0.7194 (2)	−0.1165 (5)	−0.3418 (4)	0.0914 (16)
H16B	0.7202	−0.0137	−0.3658	0.137*
H16C	0.7118	−0.1753	−0.4239	0.137*
H16A	0.7657	−0.1430	−0.2866	0.137*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0596 (6)	0.1155 (10)	0.0833 (9)	−0.0246 (6)	0.0194 (5)	−0.0174 (7)
S1	0.0600 (6)	0.0680 (7)	0.0544 (7)	−0.0145 (5)	0.0151 (4)	−0.0090 (5)
O1	0.0639 (16)	0.083 (2)	0.0595 (19)	−0.0111 (14)	0.0169 (13)	−0.0174 (16)
O2	0.0636 (17)	0.089 (2)	0.074 (2)	−0.0108 (14)	0.0351 (14)	−0.0162 (17)
O3	0.0568 (15)	0.0707 (18)	0.087 (2)	−0.0218 (14)	0.0168 (14)	−0.0001 (15)
O4	0.0796 (19)	0.103 (2)	0.063 (2)	−0.0404 (17)	0.0187 (15)	−0.0202 (17)
C1	0.052 (2)	0.070 (3)	0.057 (3)	−0.008 (2)	0.0081 (17)	0.007 (2)
C2	0.063 (2)	0.079 (3)	0.072 (3)	0.000 (2)	0.019 (2)	−0.017 (2)
C3	0.053 (2)	0.052 (2)	0.059 (3)	−0.0082 (18)	0.0088 (17)	−0.018 (2)
C4	0.051 (2)	0.054 (2)	0.042 (2)	−0.0120 (17)	0.0071 (16)	0.0042 (18)
C5	0.058 (2)	0.060 (2)	0.047 (3)	−0.0123 (19)	0.0077 (17)	0.009 (2)
C6	0.053 (2)	0.064 (2)	0.047 (2)	−0.0090 (18)	0.0144 (17)	−0.0016 (19)
C7	0.055 (2)	0.055 (2)	0.052 (2)	0.0010 (18)	0.0088 (17)	0.0050 (19)
C8	0.0426 (18)	0.048 (2)	0.052 (2)	−0.0011 (16)	0.0083 (16)	0.0051 (18)
C9	0.050 (2)	0.062 (2)	0.046 (2)	−0.0100 (18)	0.0128 (16)	0.0075 (19)
C10	0.054 (2)	0.060 (2)	0.052 (2)	−0.0082 (19)	0.0065 (17)	0.004 (2)
C11	0.0377 (18)	0.052 (2)	0.070 (3)	0.0009 (16)	0.0071 (17)	0.007 (2)
C12	0.0421 (19)	0.056 (2)	0.068 (3)	0.0032 (17)	0.0200 (17)	0.007 (2)
C13	0.0451 (19)	0.055 (2)	0.057 (3)	0.0070 (18)	0.0159 (16)	0.002 (2)
C14	0.073 (3)	0.127 (4)	0.070 (3)	−0.002 (3)	0.032 (2)	0.000 (3)
C15	0.049 (2)	0.065 (3)	0.121 (4)	−0.011 (2)	0.024 (2)	0.010 (3)
C16	0.102 (3)	0.118 (4)	0.062 (3)	−0.052 (3)	0.033 (2)	−0.021 (3)

Geometric parameters (Å, º) top

Cl1—C1	1.713 (4)	C7—C8	1.460 (5)
S1—C1	1.711 (4)	C7—H7	0.9300
S1—C4	1.719 (3)	C8—C9	1.384 (5)
O1—C5	1.234 (4)	C8—C13	1.399 (4)
O2—C13	1.367 (4)	C9—C10	1.377 (5)
O2—C14	1.411 (4)	C9—H9	0.9300
O3—C11	1.370 (4)	C10—C11	1.412 (4)
O3—C15	1.426 (4)	C11—C12	1.365 (5)
O4—C10	1.372 (4)	C12—C13	1.393 (5)
O4—C16	1.430 (4)	C12—H12	0.9300
C1—C2	1.340 (5)	C14—H14A	0.9600
C2—C3	1.415 (5)	C14—H14C	0.9600
C2—H2	0.9300	C14—H14B	0.9600
C3—C4	1.363 (4)	C15—H15C	0.9600
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.480 (4)	C15—H15B	0.9600
C5—C6	1.460 (5)	C16—H16B	0.9600
C6—C7	1.327 (4)	C16—H16C	0.9600
C6—H6	0.9300	C16—H16A	0.9600

C1—S1—C4	90.51 (18)	O4—C10—C9	125.5 (3)
C13—O2—C14	119.5 (3)	O4—C10—C11	115.8 (3)
C11—O3—C15	116.9 (3)	C9—C10—C11	118.7 (4)
C10—O4—C16	117.5 (3)	C12—C11—O3	124.6 (3)
C2—C1—S1	113.4 (3)	C12—C11—C10	120.3 (3)
C2—C1—Cl1	126.8 (3)	O3—C11—C10	115.1 (3)
S1—C1—Cl1	119.8 (2)	C11—C12—C13	120.1 (3)
C1—C2—C3	111.9 (3)	C11—C12—H12	119.9
C1—C2—H2	124.0	C13—C12—H12	119.9
C3—C2—H2	124.0	O2—C13—C12	123.6 (3)
C4—C3—C2	112.5 (3)	O2—C13—C8	115.8 (3)
C4—C3—H3	123.7	C12—C13—C8	120.6 (3)
C2—C3—H3	123.7	O2—C14—H14A	109.5
C3—C4—C5	130.2 (3)	O2—C14—H14C	109.5
C3—C4—S1	111.7 (2)	H14A—C14—H14C	109.5
C5—C4—S1	118.1 (3)	O2—C14—H14B	109.5
O1—C5—C6	122.8 (3)	H14A—C14—H14B	109.5
O1—C5—C4	120.2 (3)	H14C—C14—H14B	109.5
C6—C5—C4	116.9 (3)	O3—C15—H15C	109.5
C7—C6—C5	121.3 (3)	O3—C15—H15A	109.5
C7—C6—H6	119.4	H15C—C15—H15A	109.5
C5—C6—H6	119.4	O3—C15—H15B	109.5
C6—C7—C8	128.4 (4)	H15C—C15—H15B	109.5
C6—C7—H7	115.8	H15A—C15—H15B	109.5
C8—C7—H7	115.8	O4—C16—H16B	109.5
C9—C8—C13	118.2 (3)	O4—C16—H16C	109.5
C9—C8—C7	122.3 (3)	H16B—C16—H16C	109.5
C13—C8—C7	119.4 (3)	O4—C16—H16A	109.5
C10—C9—C8	122.1 (3)	H16B—C16—H16A	109.5
C10—C9—H9	119.0	H16C—C16—H16A	109.5
C8—C9—H9	119.0

C4—S1—C1—C2	−0.1 (3)	C16—O4—C10—C9	4.0 (6)
C4—S1—C1—Cl1	179.0 (2)	C16—O4—C10—C11	−174.8 (4)
S1—C1—C2—C3	0.4 (5)	C8—C9—C10—O4	179.8 (3)
Cl1—C1—C2—C3	−178.7 (3)	C8—C9—C10—C11	−1.4 (5)
C1—C2—C3—C4	−0.5 (5)	C15—O3—C11—C12	−11.5 (5)
C2—C3—C4—C5	−177.9 (4)	C15—O3—C11—C10	167.5 (3)
C2—C3—C4—S1	0.4 (4)	O4—C10—C11—C12	−179.8 (3)
C1—S1—C4—C3	−0.2 (3)	C9—C10—C11—C12	1.3 (5)
C1—S1—C4—C5	178.3 (3)	O4—C10—C11—O3	1.1 (5)
C3—C4—C5—O1	170.7 (4)	C9—C10—C11—O3	−177.8 (3)
S1—C4—C5—O1	−7.5 (5)	O3—C11—C12—C13	179.2 (3)
C3—C4—C5—C6	−7.5 (6)	C10—C11—C12—C13	0.2 (5)
S1—C4—C5—C6	174.3 (3)	C14—O2—C13—C12	6.9 (5)
O1—C5—C6—C7	−13.6 (6)	C14—O2—C13—C8	−172.4 (3)
C4—C5—C6—C7	164.6 (3)	C11—C12—C13—O2	179.2 (3)
C5—C6—C7—C8	−177.8 (3)	C11—C12—C13—C8	−1.6 (5)
C6—C7—C8—C9	−8.4 (6)	C9—C8—C13—O2	−179.2 (3)
C6—C7—C8—C13	168.2 (4)	C7—C8—C13—O2	4.0 (5)
C13—C8—C9—C10	0.0 (5)	C9—C8—C13—C12	1.5 (5)
C7—C8—C9—C10	176.6 (3)	C7—C8—C13—C12	−175.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.71	3.476 (4)	140
C6—H6···O1ⁱ	0.93	2.68	3.597 (5)	169

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅ClO₄S
M_r	338.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	18.2795 (12), 9.0393 (7), 9.8673 (6)
β (°)	99.390 (4)
V (Å³)	1608.57 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.20 × 0.18 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.928, 0.935
No. of measured, independent and observed [I > 2σ(I)] reflections	11590, 4590, 1621
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.197, 0.94
No. of reflections	4590
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.32

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1999), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.93	2.71	3.476 (4)	140
C6—H6···O1ⁱ	0.93	2.68	3.597 (5)	169

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

ANP is thankful to the Manipal Institute of Technology, Manipal University

References

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