3-(6-Meth­oxy-2-naphth­yl)-1-(2-thienyl)prop-2-en-1-one

The mol­ecule of the title compound, C₁₈H₁₄O₂S, is essentially planar. The central C=C double bond is trans-configured. Geometric parameters are in normal ranges.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.037
• wR factor = 0.102
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

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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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

3-(6-Methoxy-2-naphthyl)-1-(2-thienyl)prop-2-en-1-one

Crystal data

C18H14O2S	F(000) = 616
Mr = 294.35	Dx = 1.397 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12809 reflections
a = 3.9155 (3) Å	θ = 2.0–26.1°
b = 10.6776 (8) Å	µ = 0.23 mm^−1
c = 33.521 (3) Å	T = 173 K
β = 93.164 (7)°	Rod, yellow
V = 1399.3 (2) Å^3	0.22 × 0.12 × 0.12 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer	2641 independent reflections
Radiation source: fine-focus sealed tube	2315 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scans	θmax = 25.7°, θmin = 2.0°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −4→4
Tmin = 0.951, Tmax = 0.970	k = −13→12
10698 measured reflections	l = −40→32

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0685P)^2 + 0.1527P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2641 reflections	Δρmax = 0.28 e Å^−3
192 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.036 (5)

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	0.96148 (10)	0.18994 (4)	0.459951 (12)	0.03735 (17)
O1	1.0535 (3)	0.07505 (11)	0.38098 (3)	0.0427 (3)
O2	0.5708 (3)	0.26037 (11)	0.07268 (3)	0.0372 (3)
C1	0.8345 (4)	0.32248 (16)	0.48332 (5)	0.0411 (4)
H1	0.8539	0.3343	0.5114	0.049*
C2	0.7015 (4)	0.40982 (16)	0.45699 (5)	0.0392 (4)
H2	0.6193	0.4895	0.4647	0.047*
C3	0.7004 (4)	0.36780 (15)	0.41698 (5)	0.0326 (3)
H3	0.6148	0.4160	0.3948	0.039*
C4	0.8368 (3)	0.24959 (14)	0.41358 (4)	0.0299 (3)
C5	0.9002 (3)	0.17519 (14)	0.37781 (5)	0.0312 (3)
C6	0.7806 (3)	0.22670 (14)	0.33854 (4)	0.0306 (3)
H6	0.6376	0.2986	0.3373	0.037*
C7	0.8725 (3)	0.17274 (13)	0.30468 (5)	0.0289 (3)
H7	1.0156	0.1011	0.3077	0.035*
C11	0.7795 (3)	0.21059 (13)	0.26372 (4)	0.0280 (3)
C12	0.6046 (3)	0.32488 (13)	0.25431 (4)	0.0293 (3)
H12	0.5397	0.3782	0.2753	0.035*
C13	0.5292 (3)	0.35855 (13)	0.21548 (4)	0.0293 (3)
H13	0.4161	0.4358	0.2100	0.035*
C14	0.6160 (3)	0.28061 (13)	0.18313 (4)	0.0272 (3)
C15	0.7860 (3)	0.16540 (13)	0.19236 (4)	0.0276 (3)
C16	0.8657 (3)	0.13393 (13)	0.23266 (4)	0.0284 (3)
H16	0.9824	0.0576	0.2386	0.034*
C17	0.5392 (3)	0.31563 (13)	0.14296 (5)	0.0294 (3)
H17	0.4259	0.3925	0.1369	0.035*
C18	0.6300 (3)	0.23738 (14)	0.11270 (4)	0.0300 (3)
C19	0.8007 (3)	0.12286 (14)	0.12139 (5)	0.0325 (3)
H19	0.8642	0.0703	0.1002	0.039*
C20	0.8744 (3)	0.08758 (14)	0.15999 (5)	0.0314 (3)
H20	0.9864	0.0100	0.1654	0.038*
C21	0.4147 (4)	0.37813 (16)	0.06171 (5)	0.0378 (4)
H21A	0.1850	0.3820	0.0719	0.057*
H21B	0.3986	0.3860	0.0325	0.057*
H21C	0.5540	0.4467	0.0732	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0409 (2)	0.0377 (3)	0.0328 (2)	0.00101 (16)	−0.00328 (16)	0.00329 (16)
O1	0.0533 (7)	0.0339 (6)	0.0403 (6)	0.0136 (5)	−0.0025 (5)	0.0004 (5)
O2	0.0446 (6)	0.0367 (6)	0.0302 (6)	0.0016 (5)	−0.0001 (4)	−0.0027 (5)
C1	0.0434 (8)	0.0460 (10)	0.0342 (9)	−0.0061 (7)	0.0046 (7)	−0.0041 (7)
C2	0.0412 (8)	0.0366 (9)	0.0405 (9)	−0.0011 (7)	0.0084 (6)	−0.0052 (7)
C3	0.0327 (7)	0.0309 (8)	0.0345 (8)	0.0000 (6)	0.0037 (6)	0.0017 (6)
C4	0.0272 (6)	0.0307 (8)	0.0316 (8)	−0.0028 (5)	0.0013 (5)	0.0015 (6)
C5	0.0285 (7)	0.0281 (8)	0.0367 (8)	−0.0012 (5)	−0.0005 (6)	0.0014 (6)
C6	0.0290 (7)	0.0274 (7)	0.0351 (8)	−0.0004 (5)	−0.0007 (6)	0.0008 (6)
C7	0.0251 (6)	0.0254 (7)	0.0360 (8)	−0.0017 (5)	−0.0010 (5)	−0.0004 (6)
C11	0.0242 (6)	0.0259 (7)	0.0337 (8)	−0.0037 (5)	0.0009 (5)	0.0000 (6)
C12	0.0291 (7)	0.0254 (7)	0.0334 (8)	−0.0017 (5)	0.0024 (6)	−0.0032 (6)
C13	0.0292 (7)	0.0225 (7)	0.0363 (8)	0.0016 (5)	0.0024 (6)	−0.0017 (6)
C14	0.0233 (6)	0.0242 (7)	0.0342 (8)	−0.0032 (5)	0.0019 (5)	−0.0019 (6)
C15	0.0233 (6)	0.0240 (7)	0.0358 (8)	−0.0025 (5)	0.0025 (5)	−0.0026 (6)
C16	0.0256 (6)	0.0234 (7)	0.0363 (8)	−0.0007 (5)	0.0014 (5)	−0.0005 (6)
C17	0.0285 (7)	0.0252 (7)	0.0343 (8)	−0.0010 (5)	0.0004 (6)	−0.0003 (6)
C18	0.0288 (7)	0.0303 (8)	0.0310 (8)	−0.0051 (5)	0.0012 (5)	−0.0013 (6)
C19	0.0323 (7)	0.0304 (8)	0.0353 (8)	−0.0021 (6)	0.0048 (6)	−0.0071 (6)
C20	0.0302 (7)	0.0254 (7)	0.0386 (8)	0.0017 (5)	0.0035 (6)	−0.0032 (6)
C21	0.0383 (8)	0.0390 (9)	0.0353 (8)	0.0013 (6)	−0.0042 (6)	0.0010 (7)

Geometric parameters (Å, º)

S1—C1	1.7050 (18)	C12—C13	1.367 (2)
S1—C4	1.7253 (15)	C12—H12	0.9500
O1—C5	1.2279 (18)	C13—C14	1.423 (2)
O2—C18	1.3710 (18)	C13—H13	0.9500
O2—C21	1.4371 (19)	C14—C17	1.414 (2)
C1—C2	1.367 (2)	C14—C15	1.425 (2)
C1—H1	0.9500	C15—C16	1.410 (2)
C2—C3	1.414 (2)	C15—C20	1.424 (2)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.378 (2)	C17—C18	1.376 (2)
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.471 (2)	C18—C19	1.416 (2)
C5—C6	1.478 (2)	C19—C20	1.363 (2)
C6—C7	1.340 (2)	C19—H19	0.9500
C6—H6	0.9500	C20—H20	0.9500
C7—C11	1.458 (2)	C21—H21A	0.9800
C7—H7	0.9500	C21—H21B	0.9800
C11—C16	1.381 (2)	C21—H21C	0.9800
C11—C12	1.426 (2)
C1—S1—C4	91.86 (8)	C12—C13—H13	119.2
C18—O2—C21	116.96 (11)	C14—C13—H13	119.2
C2—C1—S1	112.33 (13)	C17—C14—C13	121.59 (13)
C2—C1—H1	123.8	C17—C14—C15	120.49 (13)
S1—C1—H1	123.8	C13—C14—C15	117.91 (13)
C1—C2—C3	112.15 (15)	C16—C15—C20	122.72 (13)
C1—C2—H2	123.9	C16—C15—C14	119.32 (13)
C3—C2—H2	123.9	C20—C15—C14	117.95 (13)
C4—C3—C2	112.86 (14)	C11—C16—C15	122.05 (13)
C4—C3—H3	123.6	C11—C16—H16	119.0
C2—C3—H3	123.6	C15—C16—H16	119.0
C3—C4—C5	130.24 (13)	C18—C17—C14	119.45 (13)
C3—C4—S1	110.81 (11)	C18—C17—H17	120.3
C5—C4—S1	118.88 (11)	C14—C17—H17	120.3
O1—C5—C4	120.22 (14)	O2—C18—C17	125.19 (14)
O1—C5—C6	122.02 (14)	O2—C18—C19	114.10 (13)
C4—C5—C6	117.74 (13)	C17—C18—C19	120.71 (14)
C7—C6—C5	120.51 (14)	C20—C19—C18	120.45 (13)
C7—C6—H6	119.7	C20—C19—H19	119.8
C5—C6—H6	119.7	C18—C19—H19	119.8
C6—C7—C11	127.87 (13)	C19—C20—C15	120.94 (13)
C6—C7—H7	116.1	C19—C20—H20	119.5
C11—C7—H7	116.1	C15—C20—H20	119.5
C16—C11—C12	118.35 (14)	O2—C21—H21A	109.5
C16—C11—C7	119.14 (13)	O2—C21—H21B	109.5
C12—C11—C7	122.51 (13)	H21A—C21—H21B	109.5
C13—C12—C11	120.77 (13)	O2—C21—H21C	109.5
C13—C12—H12	119.6	H21A—C21—H21C	109.5
C11—C12—H12	119.6	H21B—C21—H21C	109.5
C12—C13—C14	121.58 (13)
C4—S1—C1—C2	−0.03 (13)	C12—C13—C14—C15	−0.11 (19)
S1—C1—C2—C3	0.44 (18)	C17—C14—C15—C16	178.73 (12)
C1—C2—C3—C4	−0.74 (19)	C13—C14—C15—C16	−0.92 (19)
C2—C3—C4—C5	−176.26 (14)	C17—C14—C15—C20	−0.07 (19)
C2—C3—C4—S1	0.71 (16)	C13—C14—C15—C20	−179.72 (12)
C1—S1—C4—C3	−0.39 (12)	C12—C11—C16—C15	0.0 (2)
C1—S1—C4—C5	176.97 (12)	C7—C11—C16—C15	−179.48 (11)
C3—C4—C5—O1	173.44 (14)	C20—C15—C16—C11	179.73 (12)
S1—C4—C5—O1	−3.33 (19)	C14—C15—C16—C11	1.0 (2)
C3—C4—C5—C6	−5.2 (2)	C13—C14—C17—C18	179.66 (12)
S1—C4—C5—C6	178.04 (10)	C15—C14—C17—C18	0.0 (2)
O1—C5—C6—C7	−8.2 (2)	C21—O2—C18—C17	2.8 (2)
C4—C5—C6—C7	170.45 (13)	C21—O2—C18—C19	−176.79 (12)
C5—C6—C7—C11	−179.96 (13)	C14—C17—C18—O2	−179.92 (12)
C6—C7—C11—C16	−172.17 (14)	C14—C17—C18—C19	−0.3 (2)
C6—C7—C11—C12	8.4 (2)	O2—C18—C19—C20	−179.63 (12)
C16—C11—C12—C13	−1.0 (2)	C17—C18—C19—C20	0.8 (2)
C7—C11—C12—C13	178.39 (12)	C18—C19—C20—C15	−0.8 (2)
C11—C12—C13—C14	1.1 (2)	C16—C15—C20—C19	−178.28 (13)
C12—C13—C14—C17	−179.76 (12)	C14—C15—C20—C19	0.5 (2)