2-[(Dodecylsulfanyl)carbonothioyl­sulfanyl]­propanoic acid

Xiao, S.; Charpentier, P.A.

doi:10.1107/S1600536811007963

organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Page o811

doi:10.1107/S1600536811007963

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2-[(Dodecylsulfanyl)carbonothioylsulfanyl]propanoic acid

Shude Xiao ^a and Paul A. Charpentier ^a ^*

^aDept. of Chemical and Biochemical Engineering, Faculty of Engineering, The University of Western Ontario, London, Ontario, Canada N6A 5B9
^*Correspondence e-mail: pcharpentier@eng.uwo.ca

(Received 8 February 2011; accepted 2 March 2011; online 9 March 2011)

In the title compound, C₁₆H₃₀O₂S₃, the decyl chain adopts an extended zigzag conformation. Two molecules are disposed about a center of inversion, forming an O—H⋯O hydrogen-bonded dimer.

Related literature

For use in polymerization of acrylic acid and acrylates, see: Alb et al. (2008 , 2009 ); Konkolewicz et al. (2009 ). Various vinyl monomers can be polymerized via the RAFT (addition-fragmentation chain-transfer) mechanism by varying the substitutes of the trithiocarbonates, see: Moad et al. (2005 , 2008 ). For related structures, see: Xiao & Charpentier (2010 , 2011 ).

Experimental

Crystal data

C₁₆H₃₀O₂S₃
M_r = 350.58
Triclinic, $[P \overline 1]$
a = 6.5632 (4) Å
b = 7.0872 (4) Å
c = 22.0276 (14) Å
α = 85.819 (2)°
β = 86.873 (2)°
γ = 68.313 (2)°
V = 949.13 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 150 K
0.14 × 0.08 × 0.06 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.949, T_max = 0.977
40281 measured reflections
4522 independent reflections
3696 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.098
S = 1.08
4522 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.84	1.79	2.6292 (15)	175
Symmetry code: (i) -x, -y-1, -z+1.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007963/ng5117sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811007963/ng5117Isup2.hkl

checkCIF report

Comment top

Trithiocarbonates are a type of chain transfer agents (CTA) that are used in addition-fragmentation chain-transfer (RAFT) polymerization. Various vinyl monomers can be polymerized via the RAFT mechanism by varying the substitutes of the trithiocarbonates (Moad et al., 2005, 2008). 2-(Dodecylthiocarbonothioylthio)propanoic acid was synthesized as the RAFT-CTA mainly for polymerization of acrylic acid and acrylates, but a few other vinyl monomers were also successfully polymerized, such as acrylonitrile / 1,3-butadiene and N-isopropylacrylamide. From solution or emulsion RAFT polymerization, diblock and triblock copolymers were prepared from acrylates/acrylic acid and other vinyl monomers. Via its carboxylic acid group, 2-(dodecylthiocarbonothioylthio)propanoic acid was immobilized onto nanoparticles, such as SiO₂ and carbon black, followed by RAFT polymerization yielding hybrid nanocomposites.

Related literature top

For use of the title compound [OK?] in polymerization of acrylic acid and acrylates, see: Alb et al. (2008, 2009); Konkolewicz et al. (2009). Various vinyl monomers can be polymerized via the RAFT (addition-fragmentation chain-transfer) mechanism by varying the substitutes of the trithiocarbonates, see: Moad et al. (2005, 2008).For related structures, see: Xiao & Charpentier (2010, 2011).

Experimental top

1-Dodecanethiol 20 g (0.1 mol), triethylamine 12 g (0.12 mol) were mixed in THF 30 ml, and then carbon disulfide 11 g was added into the mixture dropwise at room temperature. The mixture was kept stirred for 1 day, and 2- bromopropionic acid 15.3 g (0.1 mol) / THF 5 ml were charged into it. The reaction lasted for 2 days at room temperature. Excess ethyl ether was used to precipitate the salts, and the solvents were evaporated. The crude product was treated with hydrobromic acid followed by extraction with ethyl ether. When the solvents were being removed, toluene was added to get rid of the residual water. Yellow crystals of 2-(dodecylthiocarbonothioylthio)propanoic acid were obtained from recrystalization in hexane/cyclohexane (10:1). m.p.: 77.21°C (DSC).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title compound (50% probability displacement ellipsoids).
	Fig. 2. Packing diagram of the structure with H-bonds.

2-[(Dodecylsulfanyl)carbonothioylsulfanyl]propanoic acid top

Crystal data top

C₁₆H₃₀O₂S₃	Z = 2
M_r = 350.58	F(000) = 380
Triclinic, P1	D_x = 1.227 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5632 (4) Å	Cell parameters from 8106 reflections
b = 7.0872 (4) Å	θ = 3.1–28.2°
c = 22.0276 (14) Å	µ = 0.39 mm⁻¹
α = 85.819 (2)°	T = 150 K
β = 86.873 (2)°	Block, yellow
γ = 68.313 (2)°	0.14 × 0.08 × 0.06 mm
V = 949.13 (10) Å³

Data collection top

Bruker APEXII diffractometer	4522 independent reflections
Radiation source: fine-focus sealed tube	3696 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 27.9°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
T_min = 0.949, T_max = 0.977	k = −9→9
40281 measured reflections	l = −28→28

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0524P)² + 0.166P] where P = (F_o² + 2F_c²)/3
4522 reflections	(Δ/σ)_max = 0.002
193 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₃₀O₂S₃	γ = 68.313 (2)°
M_r = 350.58	V = 949.13 (10) Å³
Triclinic, P1	Z = 2
a = 6.5632 (4) Å	Mo Kα radiation
b = 7.0872 (4) Å	µ = 0.39 mm⁻¹
c = 22.0276 (14) Å	T = 150 K
α = 85.819 (2)°	0.14 × 0.08 × 0.06 mm
β = 86.873 (2)°

Data collection top

Bruker APEXII diffractometer	4522 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3696 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.977	R_int = 0.050
40281 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.08	Δρ_max = 0.48 e Å⁻³
4522 reflections	Δρ_min = −0.23 e Å⁻³
193 parameters

Special details top

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	−0.09326 (7)	0.13333 (7)	0.295324 (18)	0.02645 (12)
S2	−0.35456 (6)	−0.07612 (6)	0.347313 (17)	0.02119 (11)
S3	−0.15639 (7)	0.12153 (6)	0.432049 (18)	0.02365 (11)
O1	−0.27164 (17)	−0.31220 (17)	0.51448 (5)	0.0248 (3)
H1	−0.1628	−0.3995	0.5317	0.037*
O2	−0.05484 (17)	−0.39868 (16)	0.43093 (5)	0.0217 (2)
C1	1.3203 (3)	1.3296 (3)	0.02501 (9)	0.0390 (5)
H1A	1.4290	1.2072	0.0081	0.059*
H1B	1.3941	1.4182	0.0369	0.059*
H1C	1.2121	1.4022	−0.0058	0.059*
C2	1.2050 (3)	1.2690 (3)	0.08064 (8)	0.0287 (4)
H2A	1.3149	1.2010	0.1121	0.034*
H2B	1.0971	1.3938	0.0976	0.034*
C3	1.0870 (3)	1.1280 (3)	0.06765 (7)	0.0250 (4)
H3A	1.1945	1.0026	0.0509	0.030*
H3B	0.9766	1.1956	0.0363	0.030*
C4	0.9730 (3)	1.0703 (2)	0.12409 (7)	0.0239 (3)
H4A	0.8645	1.1960	0.1404	0.029*
H4B	1.0835	1.0055	0.1556	0.029*
C5	0.8561 (3)	0.9263 (2)	0.11290 (7)	0.0236 (3)
H5A	0.9641	0.7998	0.0969	0.028*
H5B	0.7451	0.9906	0.0815	0.028*
C6	0.7434 (3)	0.8722 (2)	0.17038 (7)	0.0227 (3)
H6A	0.8554	0.8058	0.2014	0.027*
H6B	0.6385	0.9994	0.1869	0.027*
C7	0.6207 (3)	0.7320 (2)	0.16040 (7)	0.0230 (3)
H7A	0.5085	0.7980	0.1294	0.028*
H7B	0.7254	0.6042	0.1442	0.028*
C8	0.5090 (3)	0.6809 (2)	0.21833 (7)	0.0226 (3)
H8A	0.6212	0.6164	0.2494	0.027*
H8B	0.4036	0.8088	0.2343	0.027*
C9	0.3876 (3)	0.5393 (2)	0.20916 (7)	0.0221 (3)
H9A	0.4929	0.4109	0.1935	0.027*
H9B	0.2755	0.6034	0.1780	0.027*
C10	0.2757 (3)	0.4903 (2)	0.26735 (7)	0.0218 (3)
H10A	0.1689	0.6182	0.2829	0.026*
H10B	0.3871	0.4267	0.2987	0.026*
C11	0.1569 (3)	0.3471 (2)	0.25700 (7)	0.0218 (3)
H11A	0.2634	0.2199	0.2410	0.026*
H11B	0.0444	0.4114	0.2260	0.026*
C12	0.0468 (3)	0.2959 (2)	0.31527 (7)	0.0210 (3)
H12A	−0.0591	0.4217	0.3323	0.025*
H12B	0.1579	0.2249	0.3461	0.025*
C13	−0.1976 (2)	0.0663 (2)	0.36428 (7)	0.0183 (3)
C14	−0.4285 (2)	−0.1630 (2)	0.42127 (7)	0.0183 (3)
H14	−0.5124	−0.0434	0.4456	0.022*
C15	−0.2289 (2)	−0.3009 (2)	0.45571 (7)	0.0174 (3)
C16	−0.5746 (3)	−0.2836 (3)	0.41072 (8)	0.0262 (4)
H16A	−0.4925	−0.3999	0.3865	0.039*
H16B	−0.7051	−0.1953	0.3889	0.039*
H16C	−0.6195	−0.3323	0.4501	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0348 (2)	0.0340 (2)	0.0210 (2)	−0.0251 (2)	0.00321 (17)	−0.00228 (16)
S2	0.0230 (2)	0.0240 (2)	0.02111 (19)	−0.01424 (17)	−0.00368 (15)	0.00279 (15)
S3	0.0282 (2)	0.0258 (2)	0.0219 (2)	−0.01563 (17)	0.00128 (16)	−0.00304 (15)
O1	0.0193 (6)	0.0284 (6)	0.0204 (5)	−0.0024 (5)	0.0014 (4)	0.0034 (5)
O2	0.0189 (6)	0.0198 (5)	0.0231 (5)	−0.0038 (5)	0.0022 (4)	−0.0004 (4)
C1	0.0373 (11)	0.0417 (11)	0.0447 (11)	−0.0248 (9)	0.0076 (9)	0.0050 (9)
C2	0.0302 (9)	0.0303 (9)	0.0310 (9)	−0.0182 (8)	0.0051 (7)	−0.0013 (7)
C3	0.0268 (9)	0.0269 (8)	0.0253 (8)	−0.0152 (7)	0.0034 (7)	0.0000 (7)
C4	0.0260 (8)	0.0225 (8)	0.0266 (8)	−0.0134 (7)	0.0046 (7)	−0.0021 (6)
C5	0.0249 (8)	0.0253 (8)	0.0246 (8)	−0.0147 (7)	0.0012 (6)	0.0013 (6)
C6	0.0230 (8)	0.0231 (8)	0.0253 (8)	−0.0129 (7)	0.0016 (6)	0.0003 (6)
C7	0.0226 (8)	0.0242 (8)	0.0261 (8)	−0.0136 (7)	0.0015 (6)	−0.0010 (6)
C8	0.0220 (8)	0.0241 (8)	0.0253 (8)	−0.0132 (7)	0.0006 (6)	0.0005 (6)
C9	0.0220 (8)	0.0227 (8)	0.0254 (8)	−0.0131 (7)	0.0020 (6)	−0.0006 (6)
C10	0.0216 (8)	0.0229 (8)	0.0240 (8)	−0.0122 (7)	0.0007 (6)	−0.0010 (6)
C11	0.0236 (8)	0.0215 (8)	0.0236 (8)	−0.0125 (7)	0.0035 (6)	−0.0017 (6)
C12	0.0217 (8)	0.0238 (8)	0.0222 (7)	−0.0142 (7)	0.0028 (6)	−0.0020 (6)
C13	0.0144 (7)	0.0151 (7)	0.0241 (7)	−0.0042 (6)	0.0001 (6)	0.0010 (6)
C14	0.0153 (7)	0.0178 (7)	0.0218 (7)	−0.0065 (6)	−0.0004 (6)	0.0006 (6)
C15	0.0167 (7)	0.0150 (7)	0.0233 (7)	−0.0092 (6)	−0.0003 (6)	−0.0005 (6)
C16	0.0216 (8)	0.0287 (9)	0.0327 (9)	−0.0147 (7)	−0.0010 (7)	0.0007 (7)

Geometric parameters (Å, º) top

S1—C13	1.7388 (15)	C6—H6A	0.9900
S1—C12	1.8073 (15)	C6—H6B	0.9900
S2—C13	1.7565 (15)	C7—C8	1.525 (2)
S2—C14	1.8047 (15)	C7—H7A	0.9900
S3—C13	1.6316 (16)	C7—H7B	0.9900
O1—C15	1.3126 (18)	C8—C9	1.523 (2)
O1—H1	0.8400	C8—H8A	0.9900
O2—C15	1.2189 (18)	C8—H8B	0.9900
C1—C2	1.523 (2)	C9—C10	1.524 (2)
C1—H1A	0.9800	C9—H9A	0.9900
C1—H1B	0.9800	C9—H9B	0.9900
C1—H1C	0.9800	C10—C11	1.525 (2)
C2—C3	1.523 (2)	C10—H10A	0.9900
C2—H2A	0.9900	C10—H10B	0.9900
C2—H2B	0.9900	C11—C12	1.525 (2)
C3—C4	1.524 (2)	C11—H11A	0.9900
C3—H3A	0.9900	C11—H11B	0.9900
C3—H3B	0.9900	C12—H12A	0.9900
C4—C5	1.525 (2)	C12—H12B	0.9900
C4—H4A	0.9900	C14—C15	1.516 (2)
C4—H4B	0.9900	C14—C16	1.537 (2)
C5—C6	1.528 (2)	C14—H14	1.0000
C5—H5A	0.9900	C16—H16A	0.9800
C5—H5B	0.9900	C16—H16B	0.9800
C6—C7	1.525 (2)	C16—H16C	0.9800

C13—S1—C12	104.56 (7)	C7—C8—H8A	108.8
C13—S2—C14	103.56 (7)	C9—C8—H8B	108.8
C15—O1—H1	109.5	C7—C8—H8B	108.8
C2—C1—H1A	109.5	H8A—C8—H8B	107.7
C2—C1—H1B	109.5	C8—C9—C10	113.18 (13)
H1A—C1—H1B	109.5	C8—C9—H9A	108.9
C2—C1—H1C	109.5	C10—C9—H9A	108.9
H1A—C1—H1C	109.5	C8—C9—H9B	108.9
H1B—C1—H1C	109.5	C10—C9—H9B	108.9
C3—C2—C1	114.08 (15)	H9A—C9—H9B	107.8
C3—C2—H2A	108.7	C9—C10—C11	112.08 (13)
C1—C2—H2A	108.7	C9—C10—H10A	109.2
C3—C2—H2B	108.7	C11—C10—H10A	109.2
C1—C2—H2B	108.7	C9—C10—H10B	109.2
H2A—C2—H2B	107.6	C11—C10—H10B	109.2
C2—C3—C4	112.89 (14)	H10A—C10—H10B	107.9
C2—C3—H3A	109.0	C10—C11—C12	112.22 (13)
C4—C3—H3A	109.0	C10—C11—H11A	109.2
C2—C3—H3B	109.0	C12—C11—H11A	109.2
C4—C3—H3B	109.0	C10—C11—H11B	109.2
H3A—C3—H3B	107.8	C12—C11—H11B	109.2
C3—C4—C5	114.28 (13)	H11A—C11—H11B	107.9
C3—C4—H4A	108.7	C11—C12—S1	107.01 (10)
C5—C4—H4A	108.7	C11—C12—H12A	110.3
C3—C4—H4B	108.7	S1—C12—H12A	110.3
C5—C4—H4B	108.7	C11—C12—H12B	110.3
H4A—C4—H4B	107.6	S1—C12—H12B	110.3
C4—C5—C6	112.82 (13)	H12A—C12—H12B	108.6
C4—C5—H5A	109.0	S3—C13—S1	127.02 (9)
C6—C5—H5A	109.0	S3—C13—S2	126.17 (9)
C4—C5—H5B	109.0	S1—C13—S2	106.81 (8)
C6—C5—H5B	109.0	C15—C14—C16	108.83 (12)
H5A—C5—H5B	107.8	C15—C14—S2	112.00 (10)
C7—C6—C5	114.09 (13)	C16—C14—S2	107.08 (11)
C7—C6—H6A	108.7	C15—C14—H14	109.6
C5—C6—H6A	108.7	C16—C14—H14	109.6
C7—C6—H6B	108.7	S2—C14—H14	109.6
C5—C6—H6B	108.7	O2—C15—O1	124.51 (14)
H6A—C6—H6B	107.6	O2—C15—C14	123.51 (14)
C8—C7—C6	113.13 (13)	O1—C15—C14	111.83 (12)
C8—C7—H7A	109.0	C14—C16—H16A	109.5
C6—C7—H7A	109.0	C14—C16—H16B	109.5
C8—C7—H7B	109.0	H16A—C16—H16B	109.5
C6—C7—H7B	109.0	C14—C16—H16C	109.5
H7A—C7—H7B	107.8	H16A—C16—H16C	109.5
C9—C8—C7	113.71 (13)	H16B—C16—H16C	109.5
C9—C8—H8A	108.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.79	2.6292 (15)	175

Symmetry code: (i) −x, −y−1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₃₀O₂S₃
M_r	350.58
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	6.5632 (4), 7.0872 (4), 22.0276 (14)
α, β, γ (°)	85.819 (2), 86.873 (2), 68.313 (2)
V (Å³)	949.13 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.14 × 0.08 × 0.06

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.949, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	40281, 4522, 3696
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.098, 1.08
No. of reflections	4522
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.79	2.6292 (15)	175

Symmetry code: (i) −x, −y−1, −z+1.

Acknowledgements

This work was supported by the Canadian Natural Sciences and Engineering Research Council (NSERC) Idea to Innovation (I2I) Program. The authors are grateful to Dr Guerman Popov in the Department of Chemistry, the University of Western Ontario, for the data acquisition and interpretation.

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