(E,Z)-1-(4-Chloro-phen-yl)-5-phenyl-5-(phenyl-sulfan-yl)penta-2,4-dien-1-one.

The penta-2,4-dien-1-one fragment of the title compound, C23H17ClOS, is twisted by 20.0 (3)°, as measured by the dihedral angle between the planes of the carbonyl group and its attached C atom and the distant C=C double bond and its attached C atom. The 4-chloro-phenyl group forms a dihedral angle of 4.0 (3)° with the adjacent carbonyl group. Conjugation between the phenyl ring and the C=C double bond is absent; the dihedral angle between the phenyl ring and the C-C=C fragment is 34.3 (2)°. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming chains parallel to the b-axis direction.

Related literature

For the biological activity of chalcones, and their aryl­thio-containing derivatives, see: Chate et al. (2012 ▶); Nielsen et al. (2005 ▶); Wu et al. (2011 ▶), Karaman et al. (2012 ▶). For the synthesis and crystal structures of precursor 1,5-di­aryl­pent-2-en-4-yn-1-ones, see: Golovanov et al. (2013 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C23H17ClOS

M = 376.88

Orthorhombic,

a = 8.2663 (11) Å

b = 11.1661 (13) Å

c = 39.478 (6) Å

V = 3643.9 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 120 K

0.38 × 0.08 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.903, T max = 0.967

20709 measured reflections

5311 independent reflections

3104 reflections with I > 2σ(I)

R int = 0.088

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.100

S = 1.00

5311 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681302312X/ld2112sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302312X/ld2112Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302312X/ld2112Isup3.cml

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

C23H17ClOS	Dx = 1.374 Mg m−3
Mr = 376.88	Melting point = 366–280 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1957 reflections
a = 8.2663 (11) Å	θ = 2.7–27.8°
b = 11.1661 (13) Å	µ = 0.33 mm−1
c = 39.478 (6) Å	T = 120 K
V = 3643.9 (8) Å3	Needle, yellow
Z = 8	0.38 × 0.08 × 0.07 mm
F(000) = 1568

Bruker APEXII CCD diffractometer	5311 independent reflections
Radiation source: fine-focus sealed tube	3104 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.088
ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −11→11
Tmin = 0.903, Tmax = 0.967	k = −11→15
20709 measured reflections	l = −55→38

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.019P)2 + 2.8P] where P = (Fo2 + 2Fc2)/3
5311 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

Experimental. IR (KBr), ν/cm-1: 3051, 1648, 1589, 1573, 1559, 1481, 1441, 1397, 1356, 1333, 1272, 1225, 1176, 1091, 1025, 1009, 939. 1H NMR (400 MHz, CDCl3): δ = 7.02 (d, 1H, J = 11.2 Hz), 7.12 (d, 1H, J = 14.9 Hz), 7.20–8.00 (m, 14H), 8.27 (dd, 1H, J = 11.2 Hz, J = 15.0 Hz). 13C NMR (100 MHz, CDCl3): 77.5, 123.2, 127.3, 129.0, 130.1, 132.3, 134.7, 136.6, 139.2, 141.5, 153.9, 189.5. Anal. Calcd. for C23H17ClSO: C, 73.29; H, 4.67. Found: C, 73.33; H, 4.56.

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
S1	0.88212 (7)	0.25480 (5)	0.159299 (14)	0.02170 (13)
Cl1	0.91964 (8)	−0.02110 (5)	−0.110391 (14)	0.02792 (15)
O1	0.6697 (2)	0.08592 (16)	0.04724 (4)	0.0328 (4)
C1	0.7800 (3)	0.1369 (2)	0.03200 (6)	0.0222 (5)
C2	0.8736 (3)	0.2331 (2)	0.04818 (6)	0.0220 (5)
H2A	0.9446	0.2803	0.0348	0.026*
C3	0.8611 (3)	0.2558 (2)	0.08142 (5)	0.0210 (5)
H3A	0.7946	0.2043	0.0946	0.025*
C4	0.9409 (3)	0.35209 (19)	0.09840 (6)	0.0207 (5)
H4A	0.9973	0.4078	0.0845	0.025*
C5	0.9444 (3)	0.37216 (19)	0.13219 (6)	0.0188 (5)
C6	1.0132 (3)	0.48280 (19)	0.14683 (6)	0.0173 (5)
C7	1.0076 (3)	0.5896 (2)	0.12817 (6)	0.0233 (5)
H7A	0.9575	0.5906	0.1065	0.028*
C8	1.0748 (3)	0.6937 (2)	0.14119 (7)	0.0294 (6)
H8A	1.0716	0.7655	0.1283	0.035*
C9	1.1464 (3)	0.6935 (2)	0.17291 (7)	0.0293 (6)
H9A	1.1925	0.7648	0.1817	0.035*
C10	1.1504 (3)	0.5892 (2)	0.19162 (6)	0.0266 (6)
H10A	1.1986	0.5890	0.2135	0.032*
C11	1.0847 (3)	0.4850 (2)	0.17873 (6)	0.0213 (5)
H11A	1.0884	0.4137	0.1918	0.026*
C12	0.8177 (3)	0.1007 (2)	−0.00365 (6)	0.0199 (5)
C13	0.9341 (3)	0.1579 (2)	−0.02328 (6)	0.0275 (6)
H13A	0.9929	0.2234	−0.0141	0.033*
C14	0.9652 (3)	0.1205 (2)	−0.05610 (6)	0.0292 (6)
H14A	1.0441	0.1605	−0.0695	0.035*
C15	0.8809 (3)	0.0248 (2)	−0.06919 (5)	0.0206 (5)
C16	0.7655 (3)	−0.0342 (2)	−0.05040 (6)	0.0262 (6)
H16A	0.7082	−0.1002	−0.0597	0.031*
C17	0.7343 (3)	0.0043 (2)	−0.01770 (6)	0.0261 (5)
H17A	0.6546	−0.0358	−0.0046	0.031*
C18	0.7446 (3)	0.32191 (19)	0.18812 (6)	0.0176 (5)
C19	0.7105 (3)	0.2586 (2)	0.21755 (6)	0.0209 (5)
H19A	0.7657	0.1857	0.2222	0.025*
C20	0.5960 (3)	0.3016 (2)	0.24015 (6)	0.0229 (5)
H20A	0.5721	0.2575	0.2601	0.028*
C21	0.5163 (3)	0.4082 (2)	0.23384 (6)	0.0243 (5)
H21A	0.4386	0.4380	0.2495	0.029*
C22	0.5510 (3)	0.4712 (2)	0.20447 (6)	0.0232 (5)
H22A	0.4961	0.5442	0.2000	0.028*
C23	0.6647 (3)	0.4293 (2)	0.18159 (6)	0.0204 (5)
H23A	0.6879	0.4735	0.1616	0.024*

	U11	U22	U33	U12	U13	U23
S1	0.0278 (3)	0.0179 (3)	0.0194 (3)	0.0019 (3)	0.0046 (3)	0.0014 (2)
Cl1	0.0348 (3)	0.0317 (3)	0.0173 (3)	0.0022 (3)	0.0017 (3)	−0.0028 (2)
O1	0.0357 (11)	0.0387 (10)	0.0240 (9)	−0.0100 (9)	0.0075 (8)	−0.0041 (8)
C1	0.0218 (13)	0.0246 (13)	0.0202 (13)	0.0011 (10)	0.0013 (10)	0.0018 (10)
C2	0.0254 (12)	0.0218 (12)	0.0188 (11)	−0.0005 (10)	−0.0001 (10)	0.0009 (9)
C3	0.0217 (12)	0.0217 (11)	0.0197 (11)	0.0028 (10)	0.0003 (9)	0.0012 (10)
C4	0.0218 (12)	0.0204 (12)	0.0198 (12)	−0.0018 (10)	0.0022 (10)	0.0011 (9)
C5	0.0176 (11)	0.0188 (11)	0.0200 (11)	0.0027 (9)	0.0012 (10)	0.0020 (9)
C6	0.0152 (11)	0.0184 (11)	0.0183 (11)	0.0014 (9)	0.0032 (9)	0.0004 (9)
C7	0.0226 (13)	0.0239 (12)	0.0233 (13)	0.0047 (10)	0.0025 (10)	0.0005 (10)
C8	0.0338 (15)	0.0199 (13)	0.0344 (15)	0.0018 (11)	0.0083 (12)	0.0022 (11)
C9	0.0247 (14)	0.0253 (13)	0.0381 (15)	−0.0041 (11)	0.0018 (12)	−0.0099 (12)
C10	0.0208 (13)	0.0343 (14)	0.0247 (13)	0.0020 (11)	−0.0023 (11)	−0.0093 (11)
C11	0.0204 (12)	0.0230 (12)	0.0205 (11)	0.0041 (10)	0.0020 (10)	−0.0001 (10)
C12	0.0230 (12)	0.0217 (12)	0.0149 (11)	0.0028 (10)	−0.0004 (10)	0.0012 (9)
C13	0.0326 (15)	0.0299 (14)	0.0199 (12)	−0.0100 (12)	0.0000 (11)	−0.0037 (10)
C14	0.0281 (14)	0.0381 (15)	0.0213 (13)	−0.0121 (12)	0.0055 (11)	−0.0006 (11)
C15	0.0244 (12)	0.0252 (12)	0.0122 (10)	0.0059 (11)	−0.0013 (9)	−0.0003 (9)
C16	0.0330 (14)	0.0240 (13)	0.0216 (13)	−0.0065 (11)	−0.0009 (11)	−0.0022 (10)
C17	0.0297 (14)	0.0263 (13)	0.0223 (12)	−0.0086 (11)	0.0043 (11)	0.0000 (11)
C18	0.0171 (11)	0.0189 (11)	0.0168 (11)	−0.0018 (9)	−0.0001 (9)	−0.0013 (9)
C19	0.0228 (12)	0.0198 (12)	0.0203 (12)	0.0004 (10)	−0.0027 (9)	0.0016 (10)
C20	0.0266 (13)	0.0259 (12)	0.0164 (11)	−0.0048 (11)	0.0009 (10)	0.0033 (9)
C21	0.0222 (13)	0.0273 (13)	0.0232 (13)	−0.0016 (10)	0.0045 (10)	−0.0045 (10)
C22	0.0215 (13)	0.0212 (12)	0.0271 (13)	0.0000 (10)	0.0003 (10)	−0.0003 (10)
C23	0.0211 (12)	0.0198 (11)	0.0202 (12)	−0.0018 (10)	0.0012 (10)	0.0030 (9)

S1—C5	1.769 (2)	C11—H11A	0.9500
S1—C18	1.774 (2)	C12—C13	1.391 (3)
Cl1—C15	1.735 (2)	C12—C17	1.393 (3)
O1—C1	1.231 (3)	C13—C14	1.386 (3)
C1—C2	1.470 (3)	C13—H13A	0.9500
C1—C12	1.497 (3)	C14—C15	1.377 (3)
C2—C3	1.340 (3)	C14—H14A	0.9500
C2—H2A	0.9500	C15—C16	1.376 (3)
C3—C4	1.429 (3)	C16—C17	1.385 (3)
C3—H3A	0.9500	C16—H16A	0.9500
C4—C5	1.353 (3)	C17—H17A	0.9500
C4—H4A	0.9500	C18—C19	1.389 (3)
C5—C6	1.478 (3)	C18—C23	1.394 (3)
C6—C11	1.391 (3)	C19—C20	1.387 (3)
C6—C7	1.402 (3)	C19—H19A	0.9500
C7—C8	1.388 (3)	C20—C21	1.384 (3)
C7—H7A	0.9500	C20—H20A	0.9500
C8—C9	1.385 (3)	C21—C22	1.386 (3)
C8—H8A	0.9500	C21—H21A	0.9500
C9—C10	1.379 (3)	C22—C23	1.384 (3)
C9—H9A	0.9500	C22—H22A	0.9500
C10—C11	1.381 (3)	C23—H23A	0.9500
C10—H10A	0.9500
C5—S1—C18	105.17 (10)	C13—C12—C1	122.9 (2)
O1—C1—C2	121.0 (2)	C17—C12—C1	118.7 (2)
O1—C1—C12	119.2 (2)	C14—C13—C12	120.7 (2)
C2—C1—C12	119.8 (2)	C14—C13—H13A	119.6
C3—C2—C1	121.5 (2)	C12—C13—H13A	119.6
C3—C2—H2A	119.2	C15—C14—C13	119.4 (2)
C1—C2—H2A	119.2	C15—C14—H14A	120.3
C2—C3—C4	124.5 (2)	C13—C14—H14A	120.3
C2—C3—H3A	117.8	C16—C15—C14	121.3 (2)
C4—C3—H3A	117.8	C16—C15—Cl1	119.48 (18)
C5—C4—C3	126.7 (2)	C14—C15—Cl1	119.17 (18)
C5—C4—H4A	116.7	C15—C16—C17	118.9 (2)
C3—C4—H4A	116.7	C15—C16—H16A	120.6
C4—C5—C6	122.2 (2)	C17—C16—H16A	120.6
C4—C5—S1	117.89 (17)	C16—C17—C12	121.3 (2)
C6—C5—S1	119.65 (17)	C16—C17—H17A	119.4
C11—C6—C7	118.3 (2)	C12—C17—H17A	119.4
C11—C6—C5	122.2 (2)	C19—C18—C23	119.8 (2)
C7—C6—C5	119.5 (2)	C19—C18—S1	116.83 (17)
C8—C7—C6	120.3 (2)	C23—C18—S1	123.27 (17)
C8—C7—H7A	119.8	C20—C19—C18	120.0 (2)
C6—C7—H7A	119.8	C20—C19—H19A	120.0
C9—C8—C7	120.3 (2)	C18—C19—H19A	120.0
C9—C8—H8A	119.9	C21—C20—C19	120.5 (2)
C7—C8—H8A	119.9	C21—C20—H20A	119.8
C10—C9—C8	119.8 (2)	C19—C20—H20A	119.8
C10—C9—H9A	120.1	C20—C21—C22	119.2 (2)
C8—C9—H9A	120.1	C20—C21—H21A	120.4
C9—C10—C11	120.3 (2)	C22—C21—H21A	120.4
C9—C10—H10A	119.9	C23—C22—C21	121.0 (2)
C11—C10—H10A	119.9	C23—C22—H22A	119.5
C10—C11—C6	121.1 (2)	C21—C22—H22A	119.5
C10—C11—H11A	119.5	C22—C23—C18	119.5 (2)
C6—C11—H11A	119.5	C22—C23—H23A	120.3
C13—C12—C17	118.4 (2)	C18—C23—H23A	120.3
O1—C1—C2—C3	11.0 (4)	O1—C1—C12—C17	−4.6 (3)
C12—C1—C2—C3	−169.6 (2)	C2—C1—C12—C17	176.0 (2)
C1—C2—C3—C4	−176.1 (2)	C17—C12—C13—C14	0.6 (4)
C2—C3—C4—C5	−173.4 (2)	C1—C12—C13—C14	179.6 (2)
C3—C4—C5—C6	−172.1 (2)	C12—C13—C14—C15	−0.7 (4)
C3—C4—C5—S1	14.1 (3)	C13—C14—C15—C16	0.4 (4)
C18—S1—C5—C4	−131.58 (19)	C13—C14—C15—Cl1	179.6 (2)
C18—S1—C5—C6	54.5 (2)	C14—C15—C16—C17	0.0 (4)
C4—C5—C6—C11	−150.1 (2)	Cl1—C15—C16—C17	−179.20 (19)
S1—C5—C6—C11	23.6 (3)	C15—C16—C17—C12	−0.2 (4)
C4—C5—C6—C7	29.7 (3)	C13—C12—C17—C16	−0.1 (4)
S1—C5—C6—C7	−156.70 (18)	C1—C12—C17—C16	−179.2 (2)
C11—C6—C7—C8	1.2 (3)	C5—S1—C18—C19	−163.19 (18)
C5—C6—C7—C8	−178.6 (2)	C5—S1—C18—C23	20.6 (2)
C6—C7—C8—C9	−0.7 (4)	C23—C18—C19—C20	0.7 (3)
C7—C8—C9—C10	−0.1 (4)	S1—C18—C19—C20	−175.65 (18)
C8—C9—C10—C11	0.6 (4)	C18—C19—C20—C21	−0.8 (3)
C9—C10—C11—C6	−0.1 (4)	C19—C20—C21—C22	0.6 (4)
C7—C6—C11—C10	−0.8 (3)	C20—C21—C22—C23	−0.4 (4)
C5—C6—C11—C10	179.0 (2)	C21—C22—C23—C18	0.3 (4)
O1—C1—C12—C13	176.4 (2)	C19—C18—C23—C22	−0.5 (3)
C2—C1—C12—C13	−3.0 (3)	S1—C18—C23—C22	175.62 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1i	0.95	2.57	3.515 (3)	178

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O1i	0.95	2.57	3.515 (3)	178

Symmetry code: (i) .