(2E)-1-(2,5-Dichloro-3-thien-yl)-3-(6-meth-oxy-2-naphth-yl)prop-2-en-1-one.

In the title compound, C(18)H(12)Cl(2)O(2)S, the dihedral angle between the thio-phene ring and the naphthalene ring system is 2.13 (4)°. In the crystal, pairs of weak inter-molecular C-H⋯O hydrogen bonds form centrosymmetric dimers.

Related literature

For the biological activity of thio­phene-containing compounds, see: Ferreira et al. (2006 ▶); Bonini et al. (2005 ▶); Kulikova et al. (1980 ▶). For the anti­radiation activity of thio­phenes, see: Hassan et al. (1998 ▶). For the synthesis and anti­microbial evaluation of new chalcones, see: Tomar et al. (2007 ▶). For the biological activity of chalcone derivatives, see: Nowakowska et al. (2007 ▶). For related structures, see: Butcher et al. (2007 ▶); Harrison et al. (2007a ▶,b ▶); Li et al. (2009 ▶); Yathirajan et al. (2006 ▶).

Experimental

Crystal data

C18H12Cl2O2S

M = 363.24

Monoclinic,

a = 7.3237 (5) Å

b = 9.4919 (6) Å

c = 22.4037 (15) Å

β = 96.183 (1)°

V = 1548.35 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.56 mm−1

T = 100 K

0.55 × 0.40 × 0.39 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.748, T max = 0.811

17429 measured reflections

4780 independent reflections

4373 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.077

S = 0.97

4780 reflections

209 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.26 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022725/ci5100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022725/ci5100Isup2.hkl

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

C18H12Cl2O2S	F(000) = 744
Mr = 363.24	Dx = 1.558 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9959 reflections
a = 7.3237 (5) Å	θ = 2.3–31.3°
b = 9.4919 (6) Å	µ = 0.56 mm−1
c = 22.4037 (15) Å	T = 100 K
β = 96.183 (1)°	Block, yellow
V = 1548.35 (18) Å3	0.55 × 0.40 × 0.39 mm
Z = 4

Bruker APEXII CCD diffractometer	4780 independent reflections
Radiation source: fine-focus sealed tube	4373 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 31.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.748, Tmax = 0.811	k = −13→13
17429 measured reflections	l = −31→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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0374P)2 + 1.0425P] where P = (Fo2 + 2Fc2)/3
4780 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.97320 (4)	0.57727 (3)	0.666046 (12)	0.02001 (7)
Cl2	1.12452 (4)	1.16879 (3)	0.677155 (14)	0.02261 (7)
S1	1.08482 (4)	0.86262 (3)	0.702059 (12)	0.01784 (7)
O1	0.35474 (12)	−0.11321 (9)	0.30656 (4)	0.01761 (16)
O2	0.81055 (13)	0.85374 (9)	0.49460 (4)	0.02136 (18)
C1	0.93801 (15)	0.81919 (11)	0.59314 (5)	0.01381 (19)
C2	0.97881 (15)	0.96709 (12)	0.59807 (5)	0.01517 (19)
H18	0.9548	1.0307	0.5667	0.018*
C3	1.05603 (15)	1.00339 (12)	0.65347 (5)	0.0166 (2)
C4	0.99005 (15)	0.75105 (12)	0.64645 (5)	0.01516 (19)
C5	0.84960 (15)	0.76639 (12)	0.53422 (5)	0.01448 (19)
C6	0.81083 (16)	0.61554 (12)	0.52385 (5)	0.0159 (2)
H13	0.8391	0.5501	0.5544	0.019*
C7	0.73400 (15)	0.57431 (12)	0.46967 (5)	0.0159 (2)
H12	0.7128	0.6448	0.4409	0.019*
C8	0.67971 (15)	0.43260 (11)	0.45033 (5)	0.01457 (19)
C9	0.70770 (15)	0.31296 (12)	0.48855 (5)	0.01504 (19)
H9	0.7650	0.3241	0.5274	0.018*
C10	0.65144 (15)	0.18169 (12)	0.46900 (5)	0.01494 (19)
H8	0.6709	0.1050	0.4947	0.018*
C11	0.56360 (14)	0.16097 (11)	0.40986 (5)	0.01316 (19)
C12	0.53666 (14)	0.27935 (11)	0.37112 (5)	0.01365 (19)
C13	0.59605 (15)	0.41327 (11)	0.39266 (5)	0.0152 (2)
H11	0.5783	0.4907	0.3673	0.018*
C14	0.50474 (15)	0.02566 (11)	0.38918 (5)	0.01431 (19)
H2	0.5229	−0.0522	0.4143	0.017*
C15	0.42044 (15)	0.01046 (12)	0.33156 (5)	0.01419 (19)
C16	0.39546 (15)	0.12772 (12)	0.29236 (5)	0.0157 (2)
H6	0.3402	0.1154	0.2533	0.019*
C17	0.45213 (15)	0.25871 (12)	0.31159 (5)	0.0155 (2)
H5	0.4353	0.3350	0.2855	0.019*
C18	0.37100 (18)	−0.23386 (13)	0.34421 (6)	0.0225 (2)
H1A	0.4978	−0.2487	0.3586	0.034*
H1B	0.3246	−0.3149	0.3218	0.034*
H1C	0.3016	−0.2196	0.3777	0.034*

	U11	U22	U33	U12	U13	U23
Cl1	0.02618 (14)	0.01646 (13)	0.01724 (13)	0.00090 (10)	0.00169 (10)	0.00379 (9)
Cl2	0.02353 (14)	0.01989 (14)	0.02423 (14)	−0.00595 (10)	0.00179 (10)	−0.00808 (10)
S1	0.01786 (13)	0.02130 (14)	0.01387 (12)	−0.00047 (10)	−0.00050 (9)	−0.00146 (10)
O1	0.0221 (4)	0.0145 (4)	0.0154 (4)	−0.0021 (3)	−0.0015 (3)	−0.0017 (3)
O2	0.0305 (5)	0.0157 (4)	0.0167 (4)	−0.0021 (3)	−0.0032 (3)	0.0020 (3)
C1	0.0133 (4)	0.0139 (4)	0.0142 (4)	−0.0005 (3)	0.0019 (3)	−0.0009 (4)
C2	0.0150 (5)	0.0142 (5)	0.0163 (5)	−0.0010 (4)	0.0016 (4)	−0.0012 (4)
C3	0.0154 (5)	0.0164 (5)	0.0181 (5)	−0.0025 (4)	0.0022 (4)	−0.0029 (4)
C4	0.0150 (5)	0.0154 (5)	0.0151 (5)	−0.0006 (4)	0.0016 (4)	−0.0007 (4)
C5	0.0143 (5)	0.0147 (5)	0.0145 (4)	−0.0014 (4)	0.0017 (3)	−0.0010 (4)
C6	0.0189 (5)	0.0129 (5)	0.0156 (5)	−0.0005 (4)	0.0009 (4)	0.0005 (4)
C7	0.0173 (5)	0.0141 (5)	0.0161 (5)	−0.0003 (4)	0.0015 (4)	0.0000 (4)
C8	0.0145 (5)	0.0139 (5)	0.0154 (5)	−0.0005 (4)	0.0020 (4)	−0.0006 (4)
C9	0.0163 (5)	0.0156 (5)	0.0128 (4)	−0.0007 (4)	−0.0004 (4)	−0.0003 (4)
C10	0.0164 (5)	0.0146 (5)	0.0134 (4)	0.0003 (4)	−0.0004 (4)	0.0016 (4)
C11	0.0122 (4)	0.0142 (5)	0.0131 (4)	0.0002 (3)	0.0013 (3)	−0.0002 (3)
C12	0.0127 (4)	0.0148 (5)	0.0135 (4)	0.0008 (4)	0.0012 (3)	0.0000 (4)
C13	0.0170 (5)	0.0135 (5)	0.0148 (5)	0.0001 (4)	0.0010 (4)	0.0014 (4)
C14	0.0154 (5)	0.0138 (5)	0.0134 (4)	0.0000 (4)	0.0003 (3)	0.0004 (4)
C15	0.0131 (4)	0.0147 (5)	0.0148 (5)	−0.0003 (4)	0.0018 (3)	−0.0019 (4)
C16	0.0152 (5)	0.0187 (5)	0.0130 (4)	0.0007 (4)	0.0000 (4)	−0.0006 (4)
C17	0.0166 (5)	0.0170 (5)	0.0126 (4)	0.0007 (4)	0.0004 (4)	0.0016 (4)
C18	0.0285 (6)	0.0152 (5)	0.0223 (6)	−0.0033 (4)	−0.0042 (5)	0.0007 (4)

Cl1—C4	1.7148 (12)	C9—C10	1.3694 (15)
Cl2—C3	1.7148 (12)	C9—H9	0.93
S1—C3	1.7220 (12)	C10—C11	1.4230 (15)
S1—C4	1.7231 (11)	C10—H8	0.93
O1—C15	1.3657 (13)	C11—C14	1.4167 (15)
O1—C18	1.4198 (14)	C11—C12	1.4206 (15)
O2—C5	1.2257 (14)	C12—C13	1.4116 (15)
C1—C4	1.3756 (15)	C12—C17	1.4220 (15)
C1—C2	1.4371 (15)	C13—H11	0.93
C1—C5	1.4930 (15)	C14—C15	1.3772 (15)
C2—C3	1.3519 (15)	C14—H2	0.93
C2—H18	0.93	C15—C16	1.4174 (15)
C5—C6	1.4732 (15)	C16—C17	1.3658 (16)
C6—C7	1.3403 (15)	C16—H6	0.93
C6—H13	0.93	C17—H5	0.93
C7—C8	1.4553 (15)	C18—H1A	0.96
C7—H12	0.93	C18—H1B	0.96
C8—C13	1.3811 (15)	C18—H1C	0.96
C8—C9	1.4238 (15)
C3—S1—C4	90.43 (5)	C9—C10—H8	119.5
C15—O1—C18	116.50 (9)	C11—C10—H8	119.5
C4—C1—C2	110.89 (10)	C14—C11—C12	120.00 (10)
C4—C1—C5	131.54 (10)	C14—C11—C10	121.40 (10)
C2—C1—C5	117.57 (10)	C12—C11—C10	118.60 (10)
C3—C2—C1	112.49 (10)	C13—C12—C11	119.07 (10)
C3—C2—H18	123.8	C13—C12—C17	122.12 (10)
C1—C2—H18	123.8	C11—C12—C17	118.80 (10)
C2—C3—Cl2	126.65 (9)	C8—C13—C12	121.93 (10)
C2—C3—S1	113.15 (9)	C8—C13—H11	119.0
Cl2—C3—S1	120.20 (7)	C12—C13—H11	119.0
C1—C4—Cl1	130.82 (9)	C15—C14—C11	119.43 (10)
C1—C4—S1	113.03 (8)	C15—C14—H2	120.3
Cl1—C4—S1	116.14 (6)	C11—C14—H2	120.3
O2—C5—C6	121.16 (10)	O1—C15—C14	125.24 (10)
O2—C5—C1	117.28 (10)	O1—C15—C16	113.86 (9)
C6—C5—C1	121.57 (10)	C14—C15—C16	120.89 (10)
C7—C6—C5	118.79 (10)	C17—C16—C15	120.32 (10)
C7—C6—H13	120.6	C17—C16—H6	119.8
C5—C6—H13	120.6	C15—C16—H6	119.8
C6—C7—C8	127.89 (10)	C16—C17—C12	120.54 (10)
C6—C7—H12	116.1	C16—C17—H5	119.7
C8—C7—H12	116.1	C12—C17—H5	119.7
C13—C8—C9	118.50 (10)	O1—C18—H1A	109.5
C13—C8—C7	118.74 (10)	O1—C18—H1B	109.5
C9—C8—C7	122.76 (10)	H1A—C18—H1B	109.5
C10—C9—C8	120.97 (10)	O1—C18—H1C	109.5
C10—C9—H9	119.5	H1A—C18—H1C	109.5
C8—C9—H9	119.5	H1B—C18—H1C	109.5
C9—C10—C11	120.92 (10)
C4—C1—C2—C3	−0.59 (14)	C8—C9—C10—C11	0.10 (17)
C5—C1—C2—C3	179.12 (10)	C9—C10—C11—C14	−179.96 (10)
C1—C2—C3—Cl2	179.91 (8)	C9—C10—C11—C12	0.54 (16)
C1—C2—C3—S1	0.38 (13)	C14—C11—C12—C13	179.89 (10)
C4—S1—C3—C2	−0.07 (9)	C10—C11—C12—C13	−0.61 (15)
C4—S1—C3—Cl2	−179.63 (8)	C14—C11—C12—C17	−0.70 (16)
C2—C1—C4—Cl1	179.61 (9)	C10—C11—C12—C17	178.80 (10)
C5—C1—C4—Cl1	−0.04 (19)	C9—C8—C13—C12	0.61 (17)
C2—C1—C4—S1	0.53 (12)	C7—C8—C13—C12	−178.84 (10)
C5—C1—C4—S1	−179.12 (10)	C11—C12—C13—C8	0.03 (16)
C3—S1—C4—C1	−0.28 (9)	C17—C12—C13—C8	−179.36 (10)
C3—S1—C4—Cl1	−179.50 (7)	C12—C11—C14—C15	−0.45 (16)
C4—C1—C5—O2	176.66 (12)	C10—C11—C14—C15	−179.94 (10)
C2—C1—C5—O2	−2.97 (15)	C18—O1—C15—C14	1.95 (16)
C4—C1—C5—C6	−3.43 (18)	C18—O1—C15—C16	−178.24 (10)
C2—C1—C5—C6	176.94 (10)	C11—C14—C15—O1	−178.83 (10)
O2—C5—C6—C7	1.01 (17)	C11—C14—C15—C16	1.37 (16)
C1—C5—C6—C7	−178.90 (10)	O1—C15—C16—C17	179.05 (10)
C5—C6—C7—C8	−178.11 (11)	C14—C15—C16—C17	−1.13 (17)
C6—C7—C8—C13	177.68 (12)	C15—C16—C17—C12	−0.06 (17)
C6—C7—C8—C9	−1.74 (19)	C13—C12—C17—C16	−179.65 (10)
C13—C8—C9—C10	−0.68 (17)	C11—C12—C17—C16	0.96 (16)
C7—C8—C9—C10	178.74 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H18···O2i	0.93	2.56	3.2051 (14)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H18⋯O2i	0.93	2.56	3.2051 (14)	127

Symmetry code: (i) .