(E)-2-(3-Oxo-3-phenyl­prop-1-en­yl)thio­phene-3-carbaldehyde

Elumalai, K.; Raja, R.; Karunakaran, J.; Mohanakrishnan, A.K.; Murugesan, K.S.

doi:10.1107/S241431461800041X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 1| January 2018| x180041

https://doi.org/10.1107/S241431461800041X

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(E)-2-(3-Oxo-3-phenylprop-1-enyl)thiophene-3-carbaldehyde

K. Elumalai,^a R. Raja,^a Jayachandran Karunakaran,^b Arasambattu K. Mohanakrishnan ^b and K. Sakthi Murugesan ^a ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: elumalai9176@gmail.com

Edited by I. Brito, University of Antofagasta, Chile (Received 3 November 2017; accepted 7 January 2018; online 19 January 2018)

The title compound, C₁₄H₁₀O₂S, crystallizes with two independent molecules (A and B) in the asymmetric unit. They have very similar conformations with the thiophene ring having an envelope conformation in both molecules. In molecule A, the benzene and thiophene rings makes a dihedral angle of 11.01 (9)°. The corresponding angle in molecule B is 9.58 (9)°. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds, forming dimers with an R₂²(18)set-graph motif. The dimers are linked via C—H⋯O hydrogen bonds, forming slabs lying parallel to (100).

Keywords: crystal structure.

CCDC reference: 1815183

Structure description

Thiophenes are important heterocyclic compounds that are widely used as building blocks in many agrochemicals (Ansary & Omar, 2001 ). Thiophene possesses antimicrobial (Russel et al., 1988 ), analgesic and anti-inflammatory (Chen et al., 2008 ), antihypertensive (Mongevega et al., 1980 ), anti diabetes mellitus (Abdelhamid et al., 2009 ), gonadotropin releasing hormone antagonist (Sabins et al., 1944 ) activities.

Fig. 1 shows the asymmertic unit consisting of the two independent molecules (A and B) of the title compound. The two molecules have the same geometrical parameters within the precision of the experiment. In molecule A, the benzene and thiophene rings make a dihedral angle of 11.01 (9)°, the corresponding angle in molecule B being 9.58 (9)°. In molecule A, the propane group assumes an extended conformation as can be seen from the C9—C8—C7—C6 torsion angle of 178.82 (15)° [in B, C19—C20—C21—C22 = 178.14 (15)°].

Figure 1
The molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

In the crystal, the A and B molecules are linked via pairs of C—H⋯O hydrogen bonds, forming dimers with an $[R_{2}^{2}]$ (18) ring motif. The dimers are linked via C—H⋯O hydrogen bonds, forming slabs lying parallel to (100) (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O4ⁱ	0.93	2.49	3.125 (2)	126
C10—H1O⋯O3ⁱ	0.93	2.59	3.466 (2)	158
C15—H15⋯O2ⁱⁱ	0.93	2.44	3.287 (2)	152
Symmetry codes: (i) x, y-1, z; (ii) x+1, y, z.

Figure 2
A view along the b axis of the partial crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

Synthesis and crystallization

To a stirred solution of (E)-3-(3-(bromomethyl)thiophen-2-yl)-1-phenylprop-2-en-1-one (1 g, 3.26 mmol) in dry DCM, N-methylmorpholine N-oxide (0.57 g, 4.87 mmol), was added and the reaction mixture was stirred at room temperature for 6 h. Removal of solvent followed by purification by column chromatographic (silica gel; 15% ethyl acetate in hexane) gave (E)-2-(3-oxo-3-phenylprop-1-enyl)-thiophene-3-carbaldehyde as a yellow solid (0.585 g, 74%). Crystals suitable for X-ray analysis were recrystallized by slow evaporation of a ethylacetate and methanol (1:1) solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₀O₂S
M_r	242.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	10.4355 (4), 8.6955 (4), 25.7106 (9)
β (°)	95.420 (3)
V (Å³)	2322.60 (16)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.26
Crystal size (mm)	0.23 × 0.17 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.941, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	24652, 5662, 4287
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.116, 1.04
No. of reflections	5662
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXS97 and SHELXTL (Sheldrick 2008 ) and SHELXL2014 (Sheldrick, 2015 ).

Structural data

CCDC reference: 1815183

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S241431461800041X/bx4009sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461800041X/bx4009Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461800041X/bx4009Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick 2008); software used to prepare material for publication: SHELXTL (Sheldrick 2008).

(E)-2-(3-Oxo-3-phenylprop-1-enyl)thiophene-3-carbaldehyde top

Crystal data top

C₁₄H₁₀O₂S	F(000) = 1008
M_r = 242.28	D_x = 1.386 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5662 reflections
a = 10.4355 (4) Å	θ = 3.8–29.3°
b = 8.6955 (4) Å	µ = 0.26 mm⁻¹
c = 25.7106 (9) Å	T = 273 K
β = 95.420 (3)°	Colorless, yellow
V = 2322.60 (16) Å³	0.23 × 0.17 × 0.11 mm
Z = 8

Data collection top

Bruker SMART APEXII area-detector diffractometer	5662 independent reflections
Radiation source: fine-focus sealed tube	4287 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and φ scans	θ_max = 29.3°, θ_min = 3.8°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −14→13
T_min = 0.941, T_max = 0.971	k = −11→11
24652 measured reflections	l = −34→35

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0534P)² + 0.4625P] where P = (F_o² + 2F_c²)/3
5662 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Special details top

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.

N and C-bound H atoms were positioned geometrically (C–H = 0.93–0.98 Å) and allowed to ride on their parent atoms, with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for all other H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.58222 (4)	0.17941 (5)	0.533986 (17)	0.05201 (13)
C7	0.41701 (15)	0.25005 (19)	0.42763 (6)	0.0456 (4)
H7	0.4819	0.1764	0.4300	0.055*
C5	0.45568 (14)	0.30548 (17)	0.52220 (6)	0.0406 (3)
C8	0.34529 (15)	0.28131 (18)	0.37647 (6)	0.0451 (4)
C6	0.39093 (15)	0.32474 (18)	0.47036 (6)	0.0439 (3)
H6	0.3246	0.3964	0.4666	0.053*
C9	0.38064 (14)	0.19583 (17)	0.32955 (6)	0.0424 (3)
O2	0.25734 (13)	0.37418 (15)	0.37253 (5)	0.0645 (3)
C3	0.43096 (14)	0.37960 (18)	0.56796 (6)	0.0432 (3)
O1	0.31113 (15)	0.55770 (17)	0.61230 (6)	0.0794 (4)
C1	0.60052 (17)	0.2255 (2)	0.59868 (7)	0.0564 (4)
H1	0.6627	0.1820	0.6225	0.068*
C4	0.33211 (17)	0.4959 (2)	0.57214 (8)	0.0555 (4)
H4	0.2820	0.5241	0.5418	0.067*
C2	0.51515 (16)	0.3316 (2)	0.61143 (7)	0.0516 (4)
H2	0.5117	0.3694	0.6451	0.062*
C14	0.29804 (17)	0.2032 (2)	0.28401 (7)	0.0561 (4)
H14	0.2242	0.2635	0.2831	0.067*
C12	0.43303 (19)	0.0341 (2)	0.24080 (7)	0.0599 (5)
H12	0.4499	−0.0218	0.2114	0.072*
C13	0.32441 (19)	0.1220 (3)	0.24013 (7)	0.0643 (5)
H13	0.2679	0.1272	0.2100	0.077*
C10	0.49070 (18)	0.1090 (2)	0.32932 (7)	0.0597 (5)
H10	0.5482	0.1041	0.3592	0.072*
C11	0.5166 (2)	0.0289 (3)	0.28494 (7)	0.0693 (6)
H11	0.5917	−0.0289	0.2852	0.083*
S2	1.06667 (4)	0.65651 (6)	0.463918 (18)	0.05982 (15)
O4	0.82888 (11)	0.99222 (14)	0.60156 (5)	0.0575 (3)
C19	0.93792 (14)	0.77858 (19)	0.46540 (6)	0.0434 (3)
C21	0.96631 (16)	0.8293 (2)	0.56034 (6)	0.0487 (4)
H21	1.0366	0.7632	0.5646	0.058*
C22	0.92485 (14)	0.91119 (18)	0.60602 (6)	0.0445 (4)
C20	0.90501 (15)	0.84822 (19)	0.51326 (6)	0.0450 (4)
H20	0.8337	0.9128	0.5109	0.054*
C23	1.00267 (14)	0.89828 (18)	0.65772 (6)	0.0428 (3)
C15	1.03801 (19)	0.6268 (2)	0.39857 (7)	0.0609 (5)
H15	1.0874	0.5631	0.3793	0.073*
C17	0.87663 (15)	0.79548 (19)	0.41555 (6)	0.0458 (4)
O3	0.71768 (14)	0.98696 (18)	0.42779 (6)	0.0736 (4)
C28	1.10468 (16)	0.7968 (2)	0.66730 (7)	0.0527 (4)
H28	1.1264	0.7309	0.6410	0.063*
C24	0.97212 (17)	0.9946 (2)	0.69792 (7)	0.0536 (4)
H24	0.9033	1.0624	0.6923	0.064*
C16	0.93469 (17)	0.7069 (2)	0.37799 (7)	0.0554 (4)
H16	0.9047	0.7042	0.3428	0.066*
C18	0.76643 (17)	0.8961 (2)	0.40051 (7)	0.0574 (4)
H18	0.7304	0.8888	0.3661	0.069*
C25	1.0425 (2)	0.9910 (2)	0.74601 (7)	0.0622 (5)
H25	1.0216	1.0571	0.7724	0.075*
C26	1.14275 (19)	0.8910 (3)	0.75513 (7)	0.0651 (5)
H26	1.1899	0.8884	0.7877	0.078*
C27	1.17403 (18)	0.7935 (2)	0.71576 (8)	0.0652 (5)
H27	1.2423	0.7251	0.7220	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0495 (2)	0.0542 (3)	0.0525 (2)	0.00988 (19)	0.00581 (18)	−0.00906 (19)
C7	0.0494 (8)	0.0405 (8)	0.0468 (8)	−0.0003 (7)	0.0038 (7)	0.0011 (7)
C5	0.0396 (7)	0.0359 (8)	0.0471 (8)	−0.0042 (6)	0.0088 (6)	−0.0017 (6)
C8	0.0483 (8)	0.0388 (8)	0.0483 (9)	−0.0022 (7)	0.0047 (7)	0.0037 (7)
C6	0.0429 (8)	0.0403 (8)	0.0489 (8)	−0.0021 (6)	0.0071 (6)	0.0000 (7)
C9	0.0455 (8)	0.0402 (8)	0.0413 (8)	−0.0055 (6)	0.0036 (6)	0.0057 (6)
O2	0.0710 (8)	0.0602 (8)	0.0610 (7)	0.0215 (7)	−0.0007 (6)	−0.0020 (6)
C3	0.0436 (8)	0.0388 (8)	0.0486 (8)	−0.0043 (6)	0.0114 (6)	−0.0043 (7)
O1	0.0856 (10)	0.0746 (10)	0.0820 (10)	0.0174 (8)	0.0291 (8)	−0.0217 (8)
C1	0.0542 (10)	0.0630 (11)	0.0507 (10)	0.0058 (9)	−0.0018 (8)	−0.0049 (8)
C4	0.0554 (10)	0.0504 (10)	0.0623 (11)	0.0028 (8)	0.0141 (8)	−0.0049 (8)
C2	0.0541 (9)	0.0555 (10)	0.0455 (9)	−0.0011 (8)	0.0065 (7)	−0.0081 (7)
C14	0.0516 (9)	0.0617 (11)	0.0535 (10)	0.0044 (8)	−0.0026 (8)	0.0039 (8)
C12	0.0702 (12)	0.0670 (12)	0.0436 (9)	−0.0065 (10)	0.0115 (8)	−0.0052 (8)
C13	0.0668 (12)	0.0818 (14)	0.0421 (9)	−0.0051 (10)	−0.0055 (8)	−0.0015 (9)
C10	0.0602 (11)	0.0753 (13)	0.0423 (9)	0.0153 (9)	−0.0015 (7)	−0.0011 (8)
C11	0.0700 (12)	0.0863 (15)	0.0523 (10)	0.0223 (11)	0.0089 (9)	−0.0025 (10)
S2	0.0575 (3)	0.0694 (3)	0.0529 (3)	0.0180 (2)	0.0068 (2)	0.0085 (2)
O4	0.0496 (7)	0.0635 (8)	0.0595 (7)	0.0141 (6)	0.0052 (5)	−0.0009 (6)
C19	0.0408 (8)	0.0437 (8)	0.0459 (8)	−0.0037 (6)	0.0059 (6)	0.0057 (7)
C21	0.0466 (8)	0.0512 (10)	0.0486 (9)	0.0057 (7)	0.0057 (7)	0.0009 (7)
C22	0.0415 (8)	0.0431 (9)	0.0498 (9)	−0.0017 (7)	0.0087 (6)	0.0036 (7)
C20	0.0403 (8)	0.0459 (9)	0.0497 (9)	−0.0028 (7)	0.0083 (6)	0.0043 (7)
C23	0.0411 (8)	0.0429 (9)	0.0457 (8)	−0.0023 (6)	0.0103 (6)	0.0035 (7)
C15	0.0667 (11)	0.0616 (12)	0.0563 (10)	0.0059 (9)	0.0152 (9)	−0.0034 (9)
C17	0.0431 (8)	0.0465 (9)	0.0477 (8)	−0.0064 (7)	0.0035 (7)	0.0042 (7)
O3	0.0663 (8)	0.0775 (10)	0.0759 (9)	0.0185 (7)	0.0006 (7)	0.0077 (8)
C28	0.0538 (9)	0.0519 (10)	0.0536 (10)	0.0064 (8)	0.0109 (8)	0.0027 (8)
C24	0.0546 (10)	0.0533 (10)	0.0538 (9)	0.0056 (8)	0.0097 (8)	−0.0010 (8)
C16	0.0587 (10)	0.0611 (11)	0.0462 (9)	−0.0068 (9)	0.0044 (8)	−0.0012 (8)
C18	0.0508 (10)	0.0638 (12)	0.0563 (10)	−0.0051 (9)	−0.0014 (8)	0.0083 (9)
C25	0.0721 (12)	0.0672 (12)	0.0479 (9)	−0.0041 (10)	0.0099 (9)	−0.0057 (9)
C26	0.0687 (12)	0.0758 (13)	0.0495 (10)	−0.0013 (10)	−0.0016 (8)	0.0077 (9)
C27	0.0587 (11)	0.0705 (13)	0.0653 (12)	0.0144 (9)	0.0009 (9)	0.0136 (10)

Geometric parameters (Å, º) top

S1—C1	1.7040 (18)	S2—C15	1.6984 (19)
S1—C5	1.7209 (15)	S2—C19	1.7156 (16)
C7—C6	1.326 (2)	O4—C22	1.2211 (18)
C7—C8	1.476 (2)	C19—C17	1.385 (2)
C7—H7	0.9300	C19—C20	1.442 (2)
C5—C3	1.387 (2)	C21—C20	1.325 (2)
C5—C6	1.446 (2)	C21—C22	1.473 (2)
C8—O2	1.2195 (19)	C21—H21	0.9300
C8—C9	1.493 (2)	C22—C23	1.495 (2)
C6—H6	0.9300	C20—H20	0.9300
C9—C10	1.375 (2)	C23—C28	1.387 (2)
C9—C14	1.388 (2)	C23—C24	1.391 (2)
C3—C2	1.418 (2)	C15—C16	1.349 (3)
C3—C4	1.455 (2)	C15—H15	0.9300
O1—C4	1.203 (2)	C17—C16	1.416 (2)
C1—C2	1.345 (2)	C17—C18	1.468 (2)
C1—H1	0.9300	O3—C18	1.201 (2)
C4—H4	0.9300	C28—C27	1.381 (2)
C2—H2	0.9300	C28—H28	0.9300
C14—C13	1.380 (3)	C24—C25	1.378 (3)
C14—H14	0.9300	C24—H24	0.9300
C12—C11	1.365 (3)	C16—H16	0.9300
C12—C13	1.366 (3)	C18—H18	0.9300
C12—H12	0.9300	C25—C26	1.363 (3)
C13—H13	0.9300	C25—H25	0.9300
C10—C11	1.385 (3)	C26—C27	1.383 (3)
C10—H10	0.9300	C26—H26	0.9300
C11—H11	0.9300	C27—H27	0.9300

C1—S1—C5	92.04 (8)	C15—S2—C19	92.92 (9)
C6—C7—C8	121.44 (15)	C17—C19—C20	128.23 (15)
C6—C7—H7	119.3	C17—C19—S2	109.84 (12)
C8—C7—H7	119.3	C20—C19—S2	121.93 (12)
C3—C5—C6	128.31 (14)	C20—C21—C22	121.03 (15)
C3—C5—S1	110.35 (12)	C20—C21—H21	119.5
C6—C5—S1	121.34 (12)	C22—C21—H21	119.5
O2—C8—C7	120.67 (15)	O4—C22—C21	120.29 (15)
O2—C8—C9	120.28 (14)	O4—C22—C23	119.90 (14)
C7—C8—C9	119.04 (14)	C21—C22—C23	119.79 (14)
C7—C6—C5	126.31 (15)	C21—C20—C19	126.46 (15)
C7—C6—H6	116.8	C21—C20—H20	116.8
C5—C6—H6	116.8	C19—C20—H20	116.8
C10—C9—C14	118.31 (16)	C28—C23—C24	118.51 (15)
C10—C9—C8	123.18 (14)	C28—C23—C22	123.30 (15)
C14—C9—C8	118.52 (15)	C24—C23—C22	118.18 (14)
C5—C3—C2	112.39 (14)	C16—C15—S2	111.64 (14)
C5—C3—C4	125.12 (15)	C16—C15—H15	124.2
C2—C3—C4	122.48 (15)	S2—C15—H15	124.2
C2—C1—S1	112.55 (13)	C19—C17—C16	112.55 (15)
C2—C1—H1	123.7	C19—C17—C18	126.08 (16)
S1—C1—H1	123.7	C16—C17—C18	121.33 (16)
O1—C4—C3	124.18 (18)	C27—C28—C23	120.12 (17)
O1—C4—H4	117.9	C27—C28—H28	119.9
C3—C4—H4	117.9	C23—C28—H28	119.9
C1—C2—C3	112.67 (15)	C25—C24—C23	120.86 (17)
C1—C2—H2	123.7	C25—C24—H24	119.6
C3—C2—H2	123.7	C23—C24—H24	119.6
C13—C14—C9	120.65 (17)	C15—C16—C17	113.03 (16)
C13—C14—H14	119.7	C15—C16—H16	123.5
C9—C14—H14	119.7	C17—C16—H16	123.5
C11—C12—C13	119.55 (17)	O3—C18—C17	127.09 (17)
C11—C12—H12	120.2	O3—C18—H18	116.5
C13—C12—H12	120.2	C17—C18—H18	116.5
C12—C13—C14	120.35 (16)	C26—C25—C24	120.30 (18)
C12—C13—H13	119.8	C26—C25—H25	119.9
C14—C13—H13	119.8	C24—C25—H25	119.9
C9—C10—C11	120.53 (16)	C25—C26—C27	119.70 (17)
C9—C10—H10	119.7	C25—C26—H26	120.1
C11—C10—H10	119.7	C27—C26—H26	120.1
C12—C11—C10	120.59 (18)	C28—C27—C26	120.51 (17)
C12—C11—H11	119.7	C28—C27—H27	119.7
C10—C11—H11	119.7	C26—C27—H27	119.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O4ⁱ	0.93	2.49	3.125 (2)	126
C10—H1O···O3ⁱ	0.93	2.59	3.466 (2)	158
C15—H15···O2ⁱⁱ	0.93	2.44	3.287 (2)	152

Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z.

Acknowledgements

The authors thank the Department of Chemistry, Pondicherry University, India, for X-ray intensity data collection.

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