(2E)-1-(3-Methyl-2-thien­yl)-3-(3-nitro­phen­yl)prop-2-en-1-one

Chalcones are a major class of natural products having inter­esting pharmaceutical activities. The title compound, C₁₄H₁₁NO₃S, is of inter­est as a potential bioactive agent. The central acyclic C=C double bond is trans configured. All non-H atoms lie in a common plane (r.m.s. deviation 0.075 Å). In the crystal structure, the mol­ecules form a herringbone pattern.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.161
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C15     ..       6.14 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Chalcones are one of the major classes of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based foodstuff have been recently subjects of great interest for their interesting pharmacological activities. A vast number of naturally occurring chalcones are polyhydroxylated in the aryl rings. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using the compounds or chalcone rich plant extracts as drugs or food preservatives. Reviews on the bioactivities of varieties of chalcones are given by Dimmock et al. (1999) and Go et al. (2005). 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. Thiophene analogs of antiviral chalcones have been reported. In continuation of our work on chalcones, the present paper reports the crystal structure of a newly synthesized chalcone.

Geometric parameters of the title compound (Fig. 2) are in the usual ranges. All non-H atoms lie in a common plane (r.m.s. deviation 0.075 Å). In the crystal, the molecules crystallize in a herringbone pattern.

Related literature

For related structures, see: Yathirajan et al. (2006); Yathirajan, Mayekar, Narayana et al. (2007); Fischer et al. (2007); Yathirajan, Mayekar, Sarojini et al. (2007); Sarojini et al. (2007). For pharmacological activities, see: Di Carlo et al. (1999); for bioactvities of chalcones, see: Dimmock et al. (1999); Go et al. (2005); for anti-infective and anti-inflammatory activities see: Nowakowska (2007); for cancer chemopreventive agents see: Won et al. (2005); for HIV-1 integrase inhibitors see: Deng et al. (2007); for potent tyrosinase inhibitors see: Khatib et al. (2005); for the excellent blue light transmittance and good crystallizability of chalcones see: Fichou et al. (1988); Goto et al. (1991); Sarojini et al. (2006).

S2. Experimental

To a thoroughly stirred solution of 1-(3-methyl-2-thienyl)ethanone (1.40 g, 0.01 mol) and 3-nitrobenzaldehyde (1.51 g, 0.01 mol) in 25 ml me thanol, 5 ml of 40% KOH solution was added, stirred overnight and filtered. The product was crystallized from acetone (m.p.: 395–397 K). Analysis for C₁₄H₁₁NO₃S: Found (Calculated): C: 61.47 (61.52); H: 4.00 (4.06); S: 11.62% (11.73%).

S3. Refinement

H atoms were found in a difference map, but they were refined using a riding model with C—H = 0.95Å and U_iso(H) = 1.2U_eq(C) [C—H = 0.98Å and U_iso(H) = 1.5U_eq(C) for the methyl group, which was allowed to rotate but not to tip].

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. Reaction scheme.
	Fig. 2. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.
	Fig. 3. Packing diagram of the title compound with view onto the bc plane.

(2E)-1-(3-Methyl-2-thienyl)-3-(3-nitrophenyl)prop-2-en-1-one

Crystal data

C14H11NO3S	F(000) = 568
Mr = 273.30	Dx = 1.423 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6618 reflections
a = 13.9340 (18) Å	θ = 4.0–25.3°
b = 5.4166 (4) Å	µ = 0.26 mm^−1
c = 17.789 (2) Å	T = 173 K
β = 108.13 (1)°	Block, colourless
V = 1276.0 (2) Å^3	0.49 × 0.48 × 0.48 mm
Z = 4

Data collection

STOE IPDS II two-circle diffractometer	2252 independent reflections
Radiation source: fine-focus sealed tube	1989 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
ω scans	θmax = 25.0°, θmin = 4.0°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −16→15
Tmin = 0.885, Tmax = 0.887	k = −6→5
6347 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.161	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0815P)^2 + 1.859P] where P = (Fo^2 + 2Fc^2)/3
2252 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.65 e Å^−3
0 restraints	Δρmin = −0.50 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.65303 (5)	0.90494 (15)	0.09287 (4)	0.0336 (3)
N1	0.53891 (18)	0.0052 (5)	0.33857 (14)	0.0337 (6)
O1	0.92587 (15)	0.6119 (4)	0.17453 (14)	0.0389 (6)
O2	0.51014 (18)	−0.1315 (6)	0.38191 (15)	0.0560 (7)
O3	0.48346 (16)	0.1519 (5)	0.29313 (14)	0.0430 (6)
C1	0.8357 (2)	0.6517 (5)	0.16477 (16)	0.0262 (6)
C2	0.7792 (2)	0.4971 (5)	0.20648 (15)	0.0246 (6)
H2	0.7098	0.5291	0.1991	0.030*
C3	0.8258 (2)	0.3148 (5)	0.25392 (15)	0.0240 (6)
H3	0.8950	0.2903	0.2588	0.029*
C11	0.7828 (2)	0.8523 (5)	0.11302 (16)	0.0264 (6)
C12	0.8250 (2)	1.0284 (5)	0.07533 (16)	0.0312 (7)
C13	0.7517 (2)	1.1975 (6)	0.03129 (16)	0.0345 (7)
H13	0.7670	1.3292	0.0017	0.041*
C14	0.6564 (3)	1.1539 (6)	0.03523 (17)	0.0357 (7)
H14	0.5990	1.2511	0.0089	0.043*
C15	0.9313 (3)	1.0447 (6)	0.08332 (18)	0.0397 (8)
H15A	0.9700	1.0738	0.1389	0.060*
H15B	0.9425	1.1815	0.0510	0.060*
H15C	0.9536	0.8899	0.0655	0.060*
C21	0.78249 (19)	0.1471 (5)	0.29973 (15)	0.0227 (6)
C22	0.6811 (2)	0.1600 (5)	0.29780 (15)	0.0242 (6)
H22	0.6373	0.2830	0.2674	0.029*
C23	0.6465 (2)	−0.0106 (5)	0.34115 (15)	0.0250 (6)
C24	0.7056 (2)	−0.1942 (5)	0.38641 (16)	0.0284 (6)
H24	0.6786	−0.3086	0.4150	0.034*
C25	0.8057 (2)	−0.2053 (6)	0.38861 (16)	0.0309 (7)
H25	0.8486	−0.3295	0.4191	0.037*
C26	0.8442 (2)	−0.0355 (5)	0.34632 (16)	0.0274 (6)
H26	0.9133	−0.0441	0.3492	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0270 (4)	0.0387 (5)	0.0377 (4)	0.0044 (3)	0.0138 (3)	0.0058 (3)
N1	0.0249 (13)	0.0450 (15)	0.0345 (13)	−0.0067 (12)	0.0139 (10)	0.0022 (12)
O1	0.0269 (11)	0.0392 (12)	0.0567 (14)	−0.0010 (9)	0.0221 (10)	0.0088 (10)
O2	0.0361 (13)	0.0800 (19)	0.0592 (15)	−0.0079 (13)	0.0256 (12)	0.0275 (14)
O3	0.0255 (11)	0.0508 (14)	0.0569 (14)	0.0044 (10)	0.0190 (10)	0.0136 (12)
C1	0.0250 (14)	0.0273 (14)	0.0302 (13)	−0.0047 (11)	0.0144 (11)	−0.0038 (11)
C2	0.0200 (13)	0.0282 (14)	0.0291 (13)	−0.0029 (11)	0.0128 (11)	−0.0011 (11)
C3	0.0195 (12)	0.0270 (14)	0.0282 (13)	−0.0033 (11)	0.0115 (11)	−0.0042 (11)
C11	0.0303 (14)	0.0261 (14)	0.0269 (13)	−0.0043 (12)	0.0150 (11)	−0.0046 (11)
C12	0.0460 (17)	0.0263 (14)	0.0249 (13)	−0.0047 (13)	0.0165 (12)	−0.0045 (11)
C13	0.0502 (19)	0.0293 (15)	0.0250 (14)	0.0011 (14)	0.0130 (13)	0.0020 (12)
C14	0.0436 (17)	0.0346 (16)	0.0301 (15)	0.0052 (14)	0.0134 (13)	0.0028 (13)
C15	0.052 (2)	0.0311 (16)	0.0302 (15)	0.0027 (15)	0.0044 (14)	0.0014 (13)
C21	0.0211 (13)	0.0250 (13)	0.0230 (12)	−0.0022 (11)	0.0083 (10)	−0.0038 (10)
C22	0.0219 (13)	0.0272 (14)	0.0242 (12)	−0.0017 (11)	0.0082 (10)	−0.0004 (11)
C23	0.0223 (13)	0.0301 (14)	0.0250 (13)	−0.0055 (11)	0.0109 (11)	−0.0036 (11)
C24	0.0338 (15)	0.0289 (15)	0.0251 (13)	−0.0053 (12)	0.0131 (11)	−0.0004 (11)
C25	0.0338 (16)	0.0291 (15)	0.0302 (14)	0.0068 (12)	0.0106 (12)	0.0037 (12)
C26	0.0252 (14)	0.0306 (15)	0.0287 (14)	0.0010 (12)	0.0114 (11)	0.0004 (11)

Geometric parameters (Å, º)

S1—C14	1.703 (3)	C13—H13	0.9500
S1—C11	1.754 (3)	C14—H14	0.9500
N1—O3	1.222 (3)	C15—H15A	0.9800
N1—O2	1.223 (3)	C15—H15B	0.9800
N1—C23	1.488 (3)	C15—H15C	0.9800
O1—C1	1.233 (3)	C21—C26	1.400 (4)
C1—C11	1.466 (4)	C21—C22	1.404 (4)
C1—C2	1.496 (4)	C22—C23	1.383 (4)
C2—C3	1.330 (4)	C22—H22	0.9500
C2—H2	0.9500	C23—C24	1.379 (4)
C3—C21	1.470 (4)	C24—C25	1.385 (4)
C3—H3	0.9500	C24—H24	0.9500
C11—C12	1.396 (4)	C25—C26	1.396 (4)
C12—C13	1.414 (4)	C25—H25	0.9500
C12—C15	1.446 (5)	C26—H26	0.9500
C13—C14	1.372 (5)
C14—S1—C11	91.85 (15)	C12—C15—H15A	109.5
O3—N1—O2	123.2 (2)	C12—C15—H15B	109.5
O3—N1—C23	118.8 (2)	H15A—C15—H15B	109.5
O2—N1—C23	118.1 (3)	C12—C15—H15C	109.5
O1—C1—C11	120.6 (2)	H15A—C15—H15C	109.5
O1—C1—C2	120.2 (3)	H15B—C15—H15C	109.5
C11—C1—C2	119.2 (2)	C26—C21—C22	118.5 (2)
C3—C2—C1	120.1 (2)	C26—C21—C3	118.8 (2)
C3—C2—H2	120.0	C22—C21—C3	122.6 (2)
C1—C2—H2	120.0	C23—C22—C21	118.4 (3)
C2—C3—C21	127.3 (2)	C23—C22—H22	120.8
C2—C3—H3	116.3	C21—C22—H22	120.8
C21—C3—H3	116.3	C24—C23—C22	124.0 (3)
C12—C11—C1	127.1 (3)	C24—C23—N1	118.2 (2)
C12—C11—S1	110.6 (2)	C22—C23—N1	117.8 (2)
C1—C11—S1	122.3 (2)	C23—C24—C25	117.4 (3)
C11—C12—C13	111.7 (3)	C23—C24—H24	121.3
C11—C12—C15	124.5 (3)	C25—C24—H24	121.3
C13—C12—C15	123.8 (3)	C24—C25—C26	120.6 (3)
C14—C13—C12	113.8 (3)	C24—C25—H25	119.7
C14—C13—H13	123.1	C26—C25—H25	119.7
C12—C13—H13	123.1	C25—C26—C21	121.1 (3)
C13—C14—S1	112.0 (2)	C25—C26—H26	119.5
C13—C14—H14	124.0	C21—C26—H26	119.5
S1—C14—H14	124.0
O1—C1—C2—C3	−0.4 (4)	C2—C3—C21—C26	179.6 (3)
C11—C1—C2—C3	−179.7 (2)	C2—C3—C21—C22	0.6 (4)
C1—C2—C3—C21	179.5 (2)	C26—C21—C22—C23	−0.9 (4)
O1—C1—C11—C12	−5.6 (4)	C3—C21—C22—C23	178.1 (2)
C2—C1—C11—C12	173.7 (3)	C21—C22—C23—C24	−0.1 (4)
O1—C1—C11—S1	176.3 (2)	C21—C22—C23—N1	180.0 (2)
C2—C1—C11—S1	−4.4 (4)	O3—N1—C23—C24	−173.3 (3)
C14—S1—C11—C12	0.4 (2)	O2—N1—C23—C24	6.1 (4)
C14—S1—C11—C1	178.8 (2)	O3—N1—C23—C22	6.6 (4)
C1—C11—C12—C13	−178.7 (3)	O2—N1—C23—C22	−173.9 (3)
S1—C11—C12—C13	−0.4 (3)	C22—C23—C24—C25	0.5 (4)
C1—C11—C12—C15	−1.7 (5)	N1—C23—C24—C25	−179.6 (2)
S1—C11—C12—C15	176.6 (2)	C23—C24—C25—C26	0.1 (4)
C11—C12—C13—C14	0.3 (4)	C24—C25—C26—C21	−1.1 (4)
C15—C12—C13—C14	−176.8 (3)	C22—C21—C26—C25	1.5 (4)
C12—C13—C14—S1	0.0 (3)	C3—C21—C26—C25	−177.6 (2)
C11—S1—C14—C13	−0.2 (2)