organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2,4-Di­ethyl­thioxanthen-9-one

aChifeng University, Chifeng 024000, People's Republic of China
*Correspondence e-mail: liu_ge2008@163.com

(Received 16 February 2009; accepted 20 February 2009; online 28 February 2009)

The asymmetric unit of the title compound, C17H16OS, contains two crystallographically independent mol­ecules, one of which is nearly planar, the outer rings making dihedral angles of 1.51 (3) and 1.09 (3)° with the central ring. In the crystal structure, weak inter­molecular C—H⋯O hydrogen bonds link mol­ecules into chains parallel to the a axis. ππ Contacts between the thioxanthone rings [centroid–centroid distances = 3.798 (3) and 3.781 (3) Å] may further stabilize the structure.

Related literature

For general background, see: Fouassier et al. (1995[Fouassier, J. P., Ruhlmann, D., Graff, D., Morlet-Savary, F. & Wieder, F. (1995). Prog. Org. Coat. 25, 235-271.]); Roffey (1997[Roffey, C. (1997). In Photogeneration of reactive species for UV-curing. Sussex, England: Wiley.]). For a related structure, see: Bearson et al. (1996[Bearson, A. L., Eubanks, J. R. I., Farmer, A. D., Haydel, D. B. & Muller, A. J. (1996). First Chemical Corporation, Pascaquola, Michigan. US Patent No. 5 712 401.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16OS

  • Mr = 268.37

  • Triclinic, [P \overline 1]

  • a = 9.5403 (19) Å

  • b = 11.083 (2) Å

  • c = 13.807 (3) Å

  • α = 77.19 (3)°

  • β = 87.72 (3)°

  • γ = 79.35 (3)°

  • V = 1399.0 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 294 K

  • 0.15 × 0.12 × 0.10 mm

Data collection
  • Rigaku R-AXIS RAPID-S diffractometer

  • Absorption correction: none

  • 12071 measured reflections

  • 4920 independent reflections

  • 3346 reflections with I > 2σ(I)

  • Rint = 0.041

Refinement
  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.138

  • S = 1.07

  • 4920 reflections

  • 344 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14A⋯O2i 0.93 2.54 3.334 (3) 143
C32—H32A⋯O1ii 0.93 2.61 3.466 (3) 154
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation,Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Thioxanthone derivatives are good photoinitiators with excellent capabilities in UV-curing materials. They have been widely used in UV-curing applications because they absorb at a longer UV wavelength and have a faster photocuring speed than other photoinitiators. They have been introduced in processes such as printing inks, surface coatings, microelectronics and photoresists (Fouassier et al., 1995; Roffey, 1997). We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are generally within normal ranges. Rings A (S1/C1-C5), B (C4-C9), C (C2/C3/C14-C17) and D (S2/C18-C22), E (C19/C20/C23-C26), F (C21/C22/C31-C34) are, of course, planar, and they are oriented at dihedral angles of A/B = 1.51 (3), A/C = 1.09 (3), B/C = 2.54 (3) ° and D/E = 2.95 (3), D/F = 2.85 (3), E/F = 5.75 (3) °. So, rings A, B and C are nearly coplanar.

In the crystal structure, weak intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into chains parallel to the a-axis (Fig. 2), in which they may be effective in the stabilization of the structure. The π-π contacts between the thioxanthone rings, Cg1—Cg2i and Cg4—Cg4ii [symmetry codes: (i) -x, -y, 2 - z; (ii) 1 - x, 1 - y, 1 - z, where Cg1, Cg2 and Cg4 are centroids of the rings A (S1/C1-C5), B (C4-C9) and D (S2/C18-C22), respectively] may further stabilize the structure, with centroid-centroid distances of 3.798 (3) and 3.781 (3) Å, respectively.

Related literature top

For general background, see: Fouassier et al. (1995); Roffey (1997). For a related structure, see: Bearson et al. (1996). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the literature method (Bearson et al., 1996). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (80.5 mg, 0.3 mmol) in ethanol (10 ml) and evaporating ethanol slowly at room temperature for about 10 d.

Refinement top

H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A partial packing diagram of the title compound [symmetry code ('): -x, -y, -z]. Hydrogen bonds are shown as dashed lines.
2,4-Diethylthioxanthen-9-one top
Crystal data top
C17H16OSZ = 4
Mr = 268.37F(000) = 568
Triclinic, P1Dx = 1.274 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5403 (19) ÅCell parameters from 10591 reflections
b = 11.083 (2) Åθ = 3.0–27.7°
c = 13.807 (3) ŵ = 0.22 mm1
α = 77.19 (3)°T = 294 K
β = 87.72 (3)°Block, yellow
γ = 79.35 (3)°0.15 × 0.12 × 0.10 mm
V = 1399.0 (5) Å3
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
3346 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 25.0°, θmin = 3.0°
ω scansh = 1111
12071 measured reflectionsk = 1313
4920 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0457P)2 + 0.6633P]
where P = (Fo2 + 2Fc2)/3
4920 reflections(Δ/σ)max < 0.001
344 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C17H16OSγ = 79.35 (3)°
Mr = 268.37V = 1399.0 (5) Å3
Triclinic, P1Z = 4
a = 9.5403 (19) ÅMo Kα radiation
b = 11.083 (2) ŵ = 0.22 mm1
c = 13.807 (3) ÅT = 294 K
α = 77.19 (3)°0.15 × 0.12 × 0.10 mm
β = 87.72 (3)°
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer
3346 reflections with I > 2σ(I)
12071 measured reflectionsRint = 0.041
4920 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 1.07Δρmax = 0.30 e Å3
4920 reflectionsΔρmin = 0.27 e Å3
344 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
xyzUiso*/Ueq
S10.05043 (8)0.12220 (8)0.80789 (6)0.0520 (2)
S20.44522 (9)0.39943 (8)0.38211 (7)0.0609 (3)
O10.3940 (2)0.0576 (2)0.89662 (19)0.0776 (7)
O20.2369 (3)0.7698 (2)0.43252 (18)0.0775 (7)
C10.2704 (3)0.0079 (3)0.8721 (2)0.0514 (8)
C20.2069 (3)0.0339 (3)0.7856 (2)0.0453 (7)
C30.0682 (3)0.0190 (3)0.7522 (2)0.0453 (7)
C40.0448 (3)0.1358 (3)0.9095 (2)0.0443 (7)
C50.1864 (3)0.0751 (3)0.9311 (2)0.0465 (7)
C60.2526 (3)0.0939 (3)1.0140 (2)0.0550 (8)
H6A0.34690.05531.02800.066*
C70.1827 (4)0.1672 (3)1.0750 (2)0.0562 (8)
C80.0407 (4)0.2253 (3)1.0513 (2)0.0578 (8)
H8A0.00790.27501.09250.069*
C90.0300 (3)0.2125 (3)0.9707 (2)0.0490 (8)
C100.2553 (4)0.1865 (3)1.1643 (3)0.0711 (10)
H10A0.18450.19961.21510.085*
H10B0.32370.11131.19120.085*
C110.3296 (4)0.2955 (4)1.1394 (3)0.0839 (12)
H11A0.37300.30491.19820.126*
H11B0.26220.37041.11330.126*
H11C0.40180.28181.09060.126*
C120.1830 (3)0.2763 (3)0.9459 (2)0.0595 (9)
H12A0.18510.32920.87960.071*
H12B0.23880.21190.94430.071*
C130.2552 (4)0.3561 (3)1.0161 (3)0.0764 (11)
H13A0.35110.39200.99400.115*
H13B0.20330.42231.01690.115*
H13C0.25690.30461.08180.115*
C140.0149 (3)0.0109 (3)0.6691 (2)0.0561 (8)
H14A0.07770.02430.64730.067*
C150.0988 (4)0.0917 (3)0.6202 (3)0.0643 (9)
H15A0.06290.11150.56520.077*
C160.2371 (4)0.1445 (3)0.6517 (3)0.0663 (10)
H16A0.29410.19920.61770.080*
C170.2892 (3)0.1158 (3)0.7328 (2)0.0595 (9)
H17A0.38210.15170.75360.071*
C180.2905 (3)0.6672 (3)0.4167 (2)0.0542 (8)
C190.2565 (3)0.5507 (3)0.4814 (2)0.0499 (8)
C200.3206 (3)0.4300 (3)0.4732 (2)0.0501 (8)
C210.4573 (3)0.5467 (3)0.3105 (2)0.0522 (8)
C220.3880 (3)0.6599 (3)0.3316 (2)0.0500 (8)
C230.2871 (4)0.3240 (3)0.5413 (3)0.0633 (9)
C240.1856 (4)0.3452 (4)0.6124 (3)0.0777 (11)
H24A0.16270.27580.65740.093*
C250.1153 (4)0.4639 (4)0.6209 (3)0.0777 (11)
C260.1542 (4)0.5643 (3)0.5557 (3)0.0664 (10)
H26A0.11090.64500.56080.080*
C270.3561 (5)0.1909 (3)0.5352 (3)0.0816 (12)
H27A0.45610.18900.51870.098*
H27B0.35050.13540.59970.098*
C280.2864 (5)0.1424 (4)0.4588 (3)0.1110 (16)
H28A0.33450.05870.45740.166*
H28B0.29250.19640.39460.166*
H28C0.18810.14140.47590.166*
C290.0003 (5)0.4844 (5)0.6996 (3)0.1119 (17)
H29A0.07370.55470.67040.134*
H29B0.04430.41030.71740.134*
C300.0492 (6)0.5081 (6)0.7860 (4)0.149 (2)
H30A0.02900.52060.83080.223*
H30B0.09150.58220.76960.223*
H30C0.11930.43760.81710.223*
C310.4111 (4)0.7717 (3)0.2682 (3)0.0639 (9)
H31A0.36680.84830.28160.077*
C320.4975 (4)0.7706 (4)0.1867 (3)0.0789 (12)
H32A0.51120.84600.14520.095*
C330.5642 (4)0.6576 (5)0.1661 (3)0.0829 (12)
H33A0.62250.65690.11050.099*
C340.5451 (4)0.5471 (4)0.2270 (3)0.0709 (10)
H34A0.59080.47130.21290.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0420 (4)0.0550 (5)0.0615 (5)0.0026 (4)0.0015 (4)0.0228 (4)
S20.0662 (6)0.0485 (5)0.0674 (6)0.0057 (4)0.0047 (4)0.0166 (4)
O10.0514 (14)0.0868 (18)0.0989 (19)0.0108 (13)0.0142 (13)0.0459 (15)
O20.106 (2)0.0464 (14)0.0747 (17)0.0024 (13)0.0078 (14)0.0170 (12)
C10.0417 (18)0.0479 (19)0.063 (2)0.0035 (15)0.0013 (15)0.0117 (16)
C20.0421 (17)0.0393 (17)0.053 (2)0.0049 (14)0.0026 (14)0.0094 (14)
C30.0500 (18)0.0387 (17)0.0473 (19)0.0078 (14)0.0048 (14)0.0107 (13)
C40.0464 (17)0.0392 (17)0.0474 (19)0.0108 (14)0.0051 (14)0.0084 (13)
C50.0447 (18)0.0444 (17)0.0499 (19)0.0088 (14)0.0008 (14)0.0088 (14)
C60.0531 (19)0.054 (2)0.056 (2)0.0091 (16)0.0034 (16)0.0063 (16)
C70.062 (2)0.057 (2)0.049 (2)0.0121 (17)0.0038 (16)0.0084 (16)
C80.068 (2)0.054 (2)0.052 (2)0.0087 (17)0.0076 (17)0.0167 (16)
C90.0491 (18)0.0455 (18)0.051 (2)0.0063 (15)0.0024 (15)0.0105 (14)
C100.080 (3)0.076 (3)0.058 (2)0.008 (2)0.0083 (19)0.0192 (19)
C110.091 (3)0.085 (3)0.083 (3)0.017 (2)0.014 (2)0.031 (2)
C120.057 (2)0.058 (2)0.062 (2)0.0022 (16)0.0087 (16)0.0204 (17)
C130.073 (2)0.073 (3)0.078 (3)0.010 (2)0.0063 (19)0.025 (2)
C140.055 (2)0.053 (2)0.059 (2)0.0010 (16)0.0046 (16)0.0164 (16)
C150.074 (2)0.059 (2)0.060 (2)0.0007 (19)0.0069 (18)0.0224 (18)
C160.074 (2)0.057 (2)0.065 (2)0.0071 (19)0.0036 (19)0.0253 (18)
C170.054 (2)0.056 (2)0.063 (2)0.0049 (16)0.0005 (16)0.0121 (17)
C180.059 (2)0.050 (2)0.054 (2)0.0042 (17)0.0154 (16)0.0142 (16)
C190.059 (2)0.051 (2)0.0440 (19)0.0134 (16)0.0034 (15)0.0153 (15)
C200.0575 (19)0.0508 (19)0.0447 (19)0.0147 (16)0.0066 (14)0.0108 (15)
C210.0472 (18)0.061 (2)0.049 (2)0.0108 (16)0.0042 (15)0.0114 (15)
C220.0477 (18)0.052 (2)0.050 (2)0.0111 (15)0.0106 (15)0.0061 (15)
C230.081 (2)0.058 (2)0.056 (2)0.0234 (19)0.0054 (18)0.0120 (17)
C240.109 (3)0.076 (3)0.058 (2)0.047 (2)0.007 (2)0.010 (2)
C250.098 (3)0.087 (3)0.064 (3)0.044 (3)0.016 (2)0.029 (2)
C260.072 (2)0.070 (2)0.066 (2)0.0183 (19)0.0078 (19)0.031 (2)
C270.117 (3)0.057 (2)0.072 (3)0.028 (2)0.004 (2)0.0056 (19)
C280.159 (5)0.072 (3)0.113 (4)0.045 (3)0.016 (3)0.021 (3)
C290.126 (4)0.162 (5)0.076 (3)0.079 (4)0.037 (3)0.047 (3)
C300.117 (4)0.236 (7)0.140 (5)0.067 (4)0.053 (4)0.120 (5)
C310.059 (2)0.055 (2)0.072 (3)0.0135 (17)0.0111 (18)0.0026 (18)
C320.063 (2)0.082 (3)0.079 (3)0.024 (2)0.005 (2)0.017 (2)
C330.062 (2)0.112 (4)0.065 (3)0.017 (2)0.0095 (19)0.001 (2)
C340.062 (2)0.081 (3)0.068 (3)0.011 (2)0.0078 (19)0.015 (2)
Geometric parameters (Å, º) top
C1—O11.232 (3)C18—O21.220 (3)
C1—C21.467 (4)C18—C221.477 (4)
C1—C51.470 (4)C18—C191.479 (4)
C2—C31.396 (4)C19—C201.392 (4)
C2—C171.398 (4)C19—C261.401 (4)
C3—C141.402 (4)C20—C231.411 (4)
C3—S11.739 (3)C20—S21.741 (3)
C4—C51.405 (4)C21—C221.392 (4)
C4—C91.411 (4)C21—C341.398 (4)
C4—S11.750 (3)C21—S21.732 (3)
C5—C61.400 (4)C22—C311.398 (4)
C6—C71.368 (4)C23—C241.379 (5)
C6—H6A0.9300C23—C271.520 (5)
C7—C81.407 (4)C24—C251.390 (5)
C7—C101.511 (4)C24—H24A0.9300
C8—C91.371 (4)C25—C261.367 (5)
C8—H8A0.9300C25—C291.540 (5)
C9—C121.516 (4)C26—H26A0.9300
C10—C111.480 (5)C27—C281.510 (5)
C10—H10A0.9700C27—H27A0.9700
C10—H10B0.9700C27—H27B0.9700
C11—H11A0.9600C28—H28A0.9600
C11—H11B0.9600C28—H28B0.9600
C11—H11C0.9600C28—H28C0.9600
C12—C131.516 (4)C29—C301.395 (6)
C12—H12A0.9700C29—H29A0.9700
C12—H12B0.9700C29—H29B0.9700
C13—H13A0.9600C30—H30A0.9600
C13—H13B0.9600C30—H30B0.9600
C13—H13C0.9600C30—H30C0.9600
C14—C151.363 (4)C31—C321.370 (5)
C14—H14A0.9300C31—H31A0.9300
C15—C161.386 (5)C32—C331.379 (5)
C15—H15A0.9300C32—H32A0.9300
C16—C171.366 (4)C33—C341.362 (5)
C16—H16A0.9300C33—H33A0.9300
C17—H17A0.9300C34—H34A0.9300
O1—C1—C2119.9 (3)O2—C18—C19120.3 (3)
O1—C1—C5119.7 (3)C22—C18—C19120.1 (3)
C2—C1—C5120.4 (3)C20—C19—C26118.7 (3)
C3—C2—C17117.7 (3)C20—C19—C18124.0 (3)
C3—C2—C1123.7 (3)C26—C19—C18117.3 (3)
C17—C2—C1118.7 (3)C19—C20—C23120.3 (3)
C2—C3—C14120.3 (3)C19—C20—S2123.5 (2)
C2—C3—S1124.5 (2)C23—C20—S2116.2 (2)
C14—C3—S1115.1 (2)C22—C21—C34119.9 (3)
C5—C4—C9120.8 (3)C22—C21—S2124.6 (2)
C5—C4—S1123.5 (2)C34—C21—S2115.5 (3)
C9—C4—S1115.7 (2)C21—C22—C31118.1 (3)
C6—C5—C4118.6 (3)C21—C22—C18123.1 (3)
C6—C5—C1117.5 (3)C31—C22—C18118.8 (3)
C4—C5—C1124.0 (3)C24—C23—C20117.5 (3)
C7—C6—C5122.1 (3)C24—C23—C27120.7 (3)
C7—C6—H6A119.0C20—C23—C27121.8 (3)
C5—C6—H6A119.0C23—C24—C25124.0 (4)
C6—C7—C8117.6 (3)C23—C24—H24A118.0
C6—C7—C10121.6 (3)C25—C24—H24A118.0
C8—C7—C10120.8 (3)C26—C25—C24116.7 (4)
C9—C8—C7123.4 (3)C26—C25—C29120.5 (4)
C9—C8—H8A118.3C24—C25—C29122.8 (4)
C7—C8—H8A118.3C25—C26—C19122.8 (3)
C8—C9—C4117.6 (3)C25—C26—H26A118.6
C8—C9—C12122.8 (3)C19—C26—H26A118.6
C4—C9—C12119.7 (3)C28—C27—C23112.8 (3)
C11—C10—C7112.3 (3)C28—C27—H27A109.0
C11—C10—H10A109.1C23—C27—H27A109.0
C7—C10—H10A109.1C28—C27—H27B109.0
C11—C10—H10B109.1C23—C27—H27B109.0
C7—C10—H10B109.1H27A—C27—H27B107.8
H10A—C10—H10B107.9C27—C28—H28A109.5
C10—C11—H11A109.5C27—C28—H28B109.5
C10—C11—H11B109.5H28A—C28—H28B109.5
H11A—C11—H11B109.5C27—C28—H28C109.5
C10—C11—H11C109.5H28A—C28—H28C109.5
H11A—C11—H11C109.5H28B—C28—H28C109.5
H11B—C11—H11C109.5C30—C29—C25114.5 (4)
C13—C12—C9116.0 (3)C30—C29—H29A108.6
C13—C12—H12A108.3C25—C29—H29A108.6
C9—C12—H12A108.3C30—C29—H29B108.6
C13—C12—H12B108.3C25—C29—H29B108.6
C9—C12—H12B108.3H29A—C29—H29B107.6
H12A—C12—H12B107.4C29—C30—H30A109.5
C12—C13—H13A109.5C29—C30—H30B109.5
C12—C13—H13B109.5H30A—C30—H30B109.5
H13A—C13—H13B109.5C29—C30—H30C109.5
C12—C13—H13C109.5H30A—C30—H30C109.5
H13A—C13—H13C109.5H30B—C30—H30C109.5
H13B—C13—H13C109.5C32—C31—C22121.3 (4)
C15—C14—C3119.9 (3)C32—C31—H31A119.3
C15—C14—H14A120.0C22—C31—H31A119.3
C3—C14—H14A120.0C31—C32—C33119.9 (4)
C14—C15—C16120.6 (3)C31—C32—H32A120.0
C14—C15—H15A119.7C33—C32—H32A120.0
C16—C15—H15A119.7C34—C33—C32120.2 (4)
C17—C16—C15119.5 (3)C34—C33—H33A119.9
C17—C16—H16A120.2C32—C33—H33A119.9
C15—C16—H16A120.2C33—C34—C21120.6 (4)
C16—C17—C2121.9 (3)C33—C34—H34A119.7
C16—C17—H17A119.1C21—C34—H34A119.7
C2—C17—H17A119.1C3—S1—C4103.87 (14)
O2—C18—C22119.5 (3)C21—S2—C20104.32 (15)
O1—C1—C2—C3179.5 (3)C26—C19—C20—C232.6 (4)
C5—C1—C2—C31.8 (4)C18—C19—C20—C23176.7 (3)
O1—C1—C2—C170.2 (5)C26—C19—C20—S2178.0 (2)
C5—C1—C2—C17178.5 (3)C18—C19—C20—S22.6 (4)
C17—C2—C3—C140.5 (4)C34—C21—C22—C311.0 (4)
C1—C2—C3—C14179.7 (3)S2—C21—C22—C31178.3 (2)
C17—C2—C3—S1179.8 (2)C34—C21—C22—C18178.2 (3)
C1—C2—C3—S10.5 (4)S2—C21—C22—C182.4 (4)
C9—C4—C5—C61.0 (4)O2—C18—C22—C21177.7 (3)
S1—C4—C5—C6179.4 (2)C19—C18—C22—C213.3 (4)
C9—C4—C5—C1178.8 (3)O2—C18—C22—C313.0 (4)
S1—C4—C5—C10.8 (4)C19—C18—C22—C31176.0 (3)
O1—C1—C5—C60.1 (4)C19—C20—C23—C242.5 (5)
C2—C1—C5—C6178.7 (3)S2—C20—C23—C24178.1 (3)
O1—C1—C5—C4179.8 (3)C19—C20—C23—C27179.4 (3)
C2—C1—C5—C41.1 (4)S2—C20—C23—C270.1 (4)
C4—C5—C6—C71.2 (5)C20—C23—C24—C250.2 (6)
C1—C5—C6—C7178.6 (3)C27—C23—C24—C25178.3 (4)
C5—C6—C7—C80.6 (5)C23—C24—C25—C261.9 (6)
C5—C6—C7—C10179.9 (3)C23—C24—C25—C29178.5 (4)
C6—C7—C8—C90.3 (5)C24—C25—C26—C191.8 (6)
C10—C7—C8—C9179.1 (3)C29—C25—C26—C19178.6 (3)
C7—C8—C9—C40.5 (5)C20—C19—C26—C250.4 (5)
C7—C8—C9—C12179.7 (3)C18—C19—C26—C25179.0 (3)
C5—C4—C9—C80.1 (4)C24—C23—C27—C2896.8 (4)
S1—C4—C9—C8179.8 (2)C20—C23—C27—C2881.2 (4)
C5—C4—C9—C12179.7 (3)C26—C25—C29—C3084.2 (6)
S1—C4—C9—C120.0 (4)C24—C25—C29—C3095.4 (6)
C6—C7—C10—C1189.0 (4)C21—C22—C31—C320.9 (5)
C8—C7—C10—C1190.4 (4)C18—C22—C31—C32178.3 (3)
C8—C9—C12—C130.1 (5)C22—C31—C32—C330.3 (5)
C4—C9—C12—C13179.7 (3)C31—C32—C33—C340.4 (6)
C2—C3—C14—C150.2 (5)C32—C33—C34—C210.3 (6)
S1—C3—C14—C15179.6 (3)C22—C21—C34—C330.4 (5)
C3—C14—C15—C160.2 (5)S2—C21—C34—C33179.0 (3)
C14—C15—C16—C170.4 (5)C2—C3—S1—C41.2 (3)
C15—C16—C17—C20.1 (5)C14—C3—S1—C4178.2 (2)
C3—C2—C17—C160.3 (5)C5—C4—S1—C31.8 (3)
C1—C2—C17—C16179.9 (3)C9—C4—S1—C3177.9 (2)
O2—C18—C19—C20175.1 (3)C22—C21—S2—C204.8 (3)
C22—C18—C19—C205.9 (4)C34—C21—S2—C20175.8 (2)
O2—C18—C19—C264.3 (4)C19—C20—S2—C212.3 (3)
C22—C18—C19—C26174.8 (3)C23—C20—S2—C21178.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O2i0.932.543.334 (3)143
C32—H32A···O1ii0.932.613.466 (3)154
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC17H16OS
Mr268.37
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)9.5403 (19), 11.083 (2), 13.807 (3)
α, β, γ (°)77.19 (3), 87.72 (3), 79.35 (3)
V3)1399.0 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.22
Crystal size (mm)0.15 × 0.12 × 0.10
Data collection
DiffractometerRigaku R-AXIS RAPID-S
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12071, 4920, 3346
Rint0.041
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.138, 1.07
No. of reflections4920
No. of parameters344
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.27

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14A···O2i0.932.543.334 (3)143
C32—H32A···O1ii0.932.613.466 (3)154
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1.
 

Acknowledgements

The author thanks Chifeng University for supporting this work.

References

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First citationBearson, A. L., Eubanks, J. R. I., Farmer, A. D., Haydel, D. B. & Muller, A. J. (1996). First Chemical Corporation, Pascaquola, Michigan. US Patent No. 5 712 401.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFouassier, J. P., Ruhlmann, D., Graff, D., Morlet-Savary, F. & Wieder, F. (1995). Prog. Org. Coat. 25, 235-271.  CrossRef CAS Web of Science Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation,Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.  Google Scholar
First citationRoffey, C. (1997). In Photogeneration of reactive species for UV-curing. Sussex, England: Wiley.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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