(E,Z)-1-(4-Chloro­phen­yl)-5-phenyl-5-(phenyl­sulfan­yl)penta-2,4-dien-1-one

Vologzhanina, A.V.; Gusev, D.M.; Golovanov, A.A.; Pisareva, V.S.

doi:10.1107/S160053681302312X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1479

doi:10.1107/S160053681302312X

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(E,Z)-1-(4-Chlorophenyl)-5-phenyl-5-(phenylsulfanyl)penta-2,4-dien-1-one

Anna V. Vologzhanina,^a ^* Dmitry M. Gusev,^b Alexander A. Golovanov ^b and Valentina S. Pisareva ^b

^aNesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, 119991 Moscow, Russian Federation, and ^bDepartment of Chemical and Chemical Technology, Togliatti State University, 445667 Togliatti, Russian Federation
^*Correspondence e-mail: vologzhanina@mail.ru

(Received 26 July 2013; accepted 17 August 2013; online 31 August 2013)

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-chlorophenyl 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, molecules 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_r = 376.88
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.100
S = 1.00
5311 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.37 e Å⁻³

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) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

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.

Supporting information

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

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

Supporting information file. DOI: 10.1107/S160053681302312X/ld2112Isup3.cml

checkCIF report

Comment top

The family of chalcones exhibit antibiotic (Nielsen et al., 2005) and anti-inflammatory (Wu et al., 2011) activity. Arylthio-containing ketones are also active against some human pathogenic microorganisms (Chate et al., 2012; Karaman et al., 2012). Thus, a molecule which contains both fragments may have a high biological effect. Herein, we present the structure of (E, Z)-1-(4-chlorophenyl)-5-phenyl-5-phenylthio-penta-2,4-dien-1-one prepared by Michael-type addition reaction between thiophenol and 1-(4-chlorophenyl)-5-phenyl-2-penten-4-yn-1-one.

All bond lengths have characteristic values (Allen et al., 1987), although the length of the C3—C4 bond (1.429 (3) Å) indicates some electron delocalization along polyene C═C—C═C chain. The S—C distances of 1.769 (2) and 1.774 (2) Å, are slightly shortened due to mesomeric effect of sulfur electron pairs. The penta-2,4-dien-1-one fragment is twisted, the angle between two meanplanes (O1═C1—C2 and C3—C4═C5) is equal to 20.0 (3) °. The 4-chlorophenyl ring makes with the carbonyl group a dihedral angle of 4.0 (3) °. A dihedral angle between the phenyl ring and C3—C4═C5 fragment is 34.3 (2)°.

The molecules are linked in the crystal via C7—H7A···O bonds into chains parallel to the crystallographic b axis. It is worth mentioning that the C—H···O bonds which involve the hydrogen atom at o position of phenyl ring are typical for 1,5-diarylsubstituted penten-yn-ones (Golovanov, et al., 2013).

Related literature top

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 top

Three drops of triethylamine were added to a solution of 1-(4-chlorophenyl)-5-phenylpent-2-en-4-yn-1-one (322 mg, 1.21 mmol) and thiophenol (133 mg, 1.21 mmol) in 3 ml 95% ethanol. After 12 h, the precipitated yellow crystals were filtered and washed with 2 ml of cold 40% alcohol. Yield 82%. The single crystal was obtained from mixture of acetone and water. M.p. 366–367K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at 50% probability level.
	Fig. 2. The C—H···O bonded chain viewed down the a axis. Dashed lines indicate hydrogen bonds.

(E,Z)-1-(4-Chlorophenyl)-5-phenyl-5-(phenylsulfanyl)penta-2,4-dien-1-one top

Crystal data top

C₂₃H₁₇ClOS	D_x = 1.374 Mg m⁻³
M_r = 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

Data collection top

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

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.019P)² + 2.8P] where P = (F_o² + 2F_c²)/3
5311 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₂₃H₁₇ClOS	V = 3643.9 (8) Å³
M_r = 376.88	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.2663 (11) Å	µ = 0.33 mm⁻¹
b = 11.1661 (13) Å	T = 120 K
c = 39.478 (6) Å	0.38 × 0.08 × 0.07 mm

Data collection top

Bruker APEXII CCD diffractometer	5311 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	3104 reflections with I > 2σ(I)
T_min = 0.903, T_max = 0.967	R_int = 0.088
20709 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.00	Δρ_max = 0.38 e Å⁻³
5311 reflections	Δρ_min = −0.37 e Å⁻³
235 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1ⁱ	0.95	2.566	3.515 (3)	178

Symmetry code: (i) −x+3/2, y+1/2, z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chate, A. V., Joshi, R. S., Mandhane, P. G., Mohekar, S. R. & Gill, C. H. (2012). Phosphorus Sulfur Silicon Relat. Elem. 187, 327–335. Web of Science CrossRef CAS Google Scholar
Golovanov, A. A., Latypova, D. R., Bekin, V. V., Pisareva, V. S., Vologzhanina, A. V. & Dokichev, V. A. (2013). Russ. J. Org. Chem. 49. In the press. Google Scholar
Karaman, I., Gezegen, H., Ceylan, M. & Dilmac, M. (2012). Phosphorus Sulfur Silicon Relat. Elem. 187, 580–586. Web of Science CrossRef CAS Google Scholar
Nielsen, S. F., Larsen, M., Boesen, T., Schonning, K. & Kromann, H. (2005). J. Med. Chem. 48, 2667–2677. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, J., Li, J., Cai, Y., Pan, Y., Ye, F., Zhang, Y., Zhao, Y., Yang, S., Li, X. & Liang, G. (2011). J. Med. Chem. 54, 8110–8123. Web of Science CrossRef CAS PubMed Google Scholar

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Volume 69| Part 9| September 2013| Page o1479

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