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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o853.
Published online 2008 April 16. doi:  10.1107/S1600536808009884
PMCID: PMC2961221

3-Phenyl-1,5-di-2-thienylpentane-1,5-dione

Abstract

The asymmetric unit of the title compound, C19H16O2S2, contains two independent mol­ecules with slightly different conformations. In the crystal structure, weak inter­molecular C—H(...)O hydrogen bonds [C(...)O = 3.279 (15) and 3.407 (16) Å] link the mol­ecules into chains extended along the c axis.

Related literature

For related crystal structures, see: Das et al. (1994 [triangle]); Huang et al. (2006 [triangle]). For general background, see: Bose et al. (2004 [triangle]).

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Object name is e-64-0o853-scheme1.jpg

Experimental

Crystal data

  • C19H16O2S2
  • M r = 340.44
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o853-efi1.jpg
  • a = 27.912 (3) Å
  • b = 5.8607 (8) Å
  • c = 20.841 (2) Å
  • V = 3409.2 (7) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.32 mm−1
  • T = 298 (2) K
  • 0.26 × 0.17 × 0.09 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.922, T max = 0.972
  • 13190 measured reflections
  • 5636 independent reflections
  • 2006 reflections with I > 2σ(I)
  • R int = 0.120

Refinement

  • R[F 2 > 2σ(F 2)] = 0.086
  • wR(F 2) = 0.192
  • S = 1.02
  • 5636 reflections
  • 415 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.45 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2565 Friedel pairs
  • Flack parameter: 0.18 (15)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009884/cv2395sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808009884/cv2395Isup2.hkl

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

Acknowledgments

The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (grant No. X051040).

supplementary crystallographic information

Comment

In continuation of our ongoing program directed to the development of environmentally benign methods of chemical synthesis (Bose et al., 2004), we have discovered a convenient one-step method for the preparation of 1,5-diketones starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH under solvent-free conditions. Using this method, which can be considered as a general method for the synthesis of 1,5-diketones, we obtained the title compound, (I). We present here its crystal structure.

In (I) (Fig. 1), the asymmetric unit contains two independent molecules with slightly different conformations and normal bond lengths and angles comparable to those observed in 1,3,5-triphenyl-pentane-1,5-diketone (Das et al., 1994) and 1,5-diphenyl-3-(2-pyridyl)pentane-1,5-dione (Huang et al., 2006). The weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into one-dimensional chains extending along the c axis.

Experimental

2-Acetylthiophene (6.25 mmol) and freshly distilled benzaldehyde (3.125 mmol), NaOH (0.25 g, 6.25 mmol) were aggregated with glass paddle in an open flask. The resulting mixture was washed with water for several times for removing NaOH, and recrystalized from ethanol, and afforded the title compound as crystalline solid. Elemental analysis: calculated for C19H16O2S2: C 67.03, H 4.74%; Found: C 67.08, H 4.72%.

Refinement

All H atoms were positioned geometrically and refined using a riding model with C-H = 0.93-0.98 Å and Uiso(H) = Ueq(C).

Figures

Fig. 1.
Drawing of the title compound with atomic numbering scheme and 30% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity.

Crystal data

C19H16O2S2Dx = 1.327 Mg m3
Mr = 340.44Mo Kα radiation λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 1120 reflections
a = 27.912 (3) Åθ = 2.9–25.0º
b = 5.8607 (8) ŵ = 0.32 mm1
c = 20.841 (2) ÅT = 298 (2) K
V = 3409.2 (7) Å3Block, yellow
Z = 80.26 × 0.17 × 0.09 mm
F000 = 1424

Data collection

Bruker SMART CCD area-detector diffractometer5636 independent reflections
Radiation source: fine-focus sealed tube2006 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.120
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −14→33
Tmin = 0.922, Tmax = 0.972k = −6→6
13190 measured reflectionsl = −24→20

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.086  w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.192(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.36 e Å3
5636 reflectionsΔρmin = −0.45 e Å3
415 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), 2565 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.18 (15)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
O10.4895 (3)0.4760 (15)−0.0653 (3)0.100 (3)
O20.5431 (3)0.5207 (16)0.1105 (5)0.117 (3)
O30.2607 (3)1.1103 (14)0.1107 (3)0.093 (2)
O40.2020 (3)0.8734 (18)−0.0734 (4)0.117 (3)
S10.49589 (12)0.5733 (5)−0.20432 (17)0.0981 (11)
S20.62799 (13)0.6688 (7)0.18264 (19)0.1168 (13)
S30.25330 (11)1.0432 (5)0.24992 (17)0.0937 (10)
S40.11681 (15)0.6173 (10)−0.1171 (2)0.1467 (19)
C10.4854 (4)0.772 (2)−0.2610 (6)0.091 (4)
H10.48940.7482−0.30480.109*
C20.4704 (4)0.969 (2)−0.2348 (6)0.081 (3)
H20.46401.1001−0.25850.098*
C30.4655 (4)0.957 (2)−0.1689 (6)0.078 (3)
H30.45501.0777−0.14360.094*
C40.4779 (3)0.747 (2)−0.1452 (6)0.064 (3)
C50.4773 (4)0.676 (2)−0.0809 (6)0.074 (3)
C60.4575 (4)0.8254 (19)−0.0275 (5)0.075 (3)
H6A0.46480.9830−0.03780.089*
H6B0.42290.8103−0.02760.089*
C70.4748 (4)0.7802 (17)0.0391 (5)0.058 (3)
H70.47330.61470.04550.070*
C80.5276 (3)0.8490 (17)0.0456 (5)0.064 (3)
H8A0.54340.82450.00470.077*
H8B0.52931.01070.05520.077*
C90.5549 (4)0.718 (2)0.0976 (6)0.075 (4)
C100.5955 (4)0.820 (2)0.1275 (5)0.087 (4)
C110.6126 (4)1.045 (2)0.1228 (6)0.090 (4)
H110.59951.15840.09700.108*
C120.6526 (5)1.072 (2)0.1631 (7)0.102 (4)
H120.66991.20770.16540.123*
C130.6638 (4)0.890 (2)0.1975 (6)0.107 (4)
H130.68900.88600.22680.128*
C140.4456 (3)0.8857 (19)0.0911 (6)0.061 (3)
C150.4379 (4)0.782 (2)0.1486 (7)0.078 (3)
H150.45120.63890.15590.093*
C160.4109 (4)0.883 (3)0.1972 (7)0.095 (4)
H160.40600.80630.23560.114*
C170.3914 (5)1.096 (3)0.1884 (7)0.100 (5)
H170.37401.16660.22100.121*
C180.3979 (4)1.200 (2)0.1324 (8)0.088 (4)
H180.38321.33990.12580.105*
C190.4253 (4)1.1110 (19)0.0834 (6)0.083 (3)
H190.43071.19450.04620.100*
C200.2648 (4)0.857 (3)0.3085 (5)0.099 (4)
H200.25700.88010.35140.119*
C210.2870 (4)0.667 (2)0.2862 (7)0.094 (4)
H210.29720.55070.31350.113*
C220.2936 (3)0.6553 (17)0.2214 (4)0.049 (3)
H220.30670.53340.19880.058*
C230.2767 (3)0.8648 (17)0.1944 (5)0.059 (3)
C240.2767 (3)0.925 (2)0.1271 (6)0.067 (3)
C250.2983 (4)0.7695 (18)0.0785 (5)0.069 (3)
H25A0.33200.80660.07460.083*
H25B0.29610.61450.09460.083*
C260.2767 (3)0.7758 (17)0.0135 (5)0.060 (3)
H260.27170.93660.00240.072*
C270.2264 (4)0.6603 (19)0.0151 (5)0.072 (3)
H27A0.23100.49730.02030.087*
H27B0.20950.71480.05270.087*
C280.1956 (5)0.698 (3)−0.0415 (7)0.090 (4)
C290.1564 (5)0.554 (4)−0.0595 (8)0.125 (6)
C300.1481 (6)0.341 (4)−0.0319 (8)0.141 (7)
H300.16660.27240.00000.169*
C310.1071 (6)0.247 (3)−0.0608 (8)0.141 (7)
H310.09530.1058−0.04800.169*
C320.0852 (6)0.368 (3)−0.1074 (9)0.144 (7)
H320.05810.3241−0.13020.173*
C330.3080 (3)0.6706 (19)−0.0394 (5)0.054 (3)
C340.3164 (4)0.7746 (18)−0.0964 (6)0.066 (3)
H340.30170.9139−0.10480.079*
C350.3456 (5)0.683 (3)−0.1420 (6)0.086 (4)
H350.35250.7628−0.17930.103*
C360.3646 (4)0.470 (3)−0.1320 (7)0.098 (4)
H360.38280.4010−0.16380.117*
C370.3570 (4)0.364 (2)−0.0771 (7)0.088 (4)
H370.37190.2247−0.07030.106*
C380.3279 (4)0.4499 (18)−0.0293 (5)0.071 (3)
H380.32160.36710.00780.086*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.139 (7)0.062 (6)0.100 (6)0.030 (5)−0.003 (5)−0.002 (5)
O20.103 (7)0.085 (7)0.163 (8)−0.004 (5)−0.025 (6)0.055 (6)
O30.127 (7)0.055 (6)0.096 (6)−0.017 (5)−0.016 (5)−0.007 (5)
O40.072 (6)0.154 (10)0.125 (8)0.003 (6)0.026 (5)0.043 (7)
S10.127 (3)0.068 (2)0.100 (2)0.006 (2)0.014 (2)−0.017 (2)
S20.098 (3)0.120 (3)0.133 (3)0.028 (2)−0.036 (2)−0.004 (3)
S30.102 (2)0.085 (2)0.094 (2)0.001 (2)−0.003 (2)−0.020 (2)
S40.077 (3)0.214 (5)0.149 (4)−0.018 (3)0.024 (3)−0.068 (4)
C10.115 (10)0.074 (10)0.083 (10)−0.017 (8)0.020 (8)−0.015 (8)
C20.108 (9)0.056 (9)0.080 (10)0.004 (7)0.004 (8)0.009 (7)
C30.091 (9)0.071 (10)0.072 (9)0.007 (7)0.003 (7)−0.005 (8)
C40.046 (6)0.090 (11)0.056 (8)−0.007 (6)−0.005 (6)−0.001 (7)
C50.063 (8)0.059 (8)0.100 (10)0.015 (6)−0.009 (7)−0.021 (8)
C60.074 (7)0.073 (8)0.076 (9)0.013 (6)−0.008 (7)−0.011 (7)
C70.068 (8)0.047 (7)0.060 (7)−0.002 (5)−0.008 (7)0.000 (5)
C80.062 (8)0.065 (8)0.066 (7)−0.005 (6)−0.004 (6)0.011 (6)
C90.042 (7)0.089 (10)0.094 (10)0.010 (7)0.009 (7)0.017 (8)
C100.067 (9)0.085 (10)0.109 (10)0.023 (8)−0.022 (7)−0.013 (8)
C110.077 (9)0.083 (10)0.110 (10)0.016 (8)−0.016 (8)−0.022 (8)
C120.091 (10)0.088 (11)0.128 (12)0.010 (8)−0.020 (9)−0.017 (9)
C130.087 (10)0.107 (12)0.125 (11)0.026 (9)−0.024 (8)−0.023 (10)
C140.056 (7)0.054 (8)0.072 (9)−0.004 (6)−0.015 (6)−0.004 (7)
C150.083 (9)0.065 (8)0.085 (10)−0.002 (7)−0.014 (8)0.005 (8)
C160.068 (9)0.124 (14)0.094 (11)−0.019 (9)0.000 (8)0.003 (10)
C170.076 (9)0.149 (16)0.077 (11)−0.008 (10)0.008 (8)−0.025 (11)
C180.076 (9)0.088 (10)0.099 (11)0.009 (7)−0.006 (8)−0.032 (10)
C190.105 (10)0.051 (9)0.093 (9)−0.005 (7)0.002 (8)−0.018 (7)
C200.076 (8)0.176 (15)0.046 (8)0.022 (9)0.006 (6)−0.008 (9)
C210.073 (8)0.087 (10)0.123 (13)−0.017 (7)0.022 (8)0.012 (10)
C220.067 (7)0.053 (7)0.026 (6)−0.008 (5)0.001 (5)0.002 (5)
C230.052 (6)0.074 (8)0.050 (7)0.013 (5)−0.011 (6)−0.003 (6)
C240.054 (7)0.048 (8)0.098 (10)−0.002 (6)−0.006 (6)0.010 (8)
C250.074 (8)0.069 (8)0.064 (8)−0.016 (6)−0.002 (7)−0.011 (6)
C260.052 (7)0.057 (7)0.069 (8)−0.001 (5)0.004 (6)0.013 (6)
C270.066 (8)0.084 (9)0.067 (8)−0.001 (6)0.004 (6)0.002 (6)
C280.091 (10)0.103 (11)0.076 (10)−0.019 (9)−0.007 (8)0.008 (8)
C290.057 (10)0.182 (19)0.134 (15)0.002 (12)0.018 (10)−0.077 (14)
C300.078 (12)0.18 (2)0.163 (17)0.000 (13)0.018 (11)−0.081 (15)
C310.079 (13)0.19 (2)0.159 (17)−0.002 (12)0.017 (11)−0.078 (15)
C320.080 (12)0.19 (2)0.161 (17)0.004 (12)0.023 (11)−0.088 (14)
C330.046 (6)0.064 (8)0.052 (7)0.011 (5)0.002 (5)−0.006 (6)
C340.075 (8)0.059 (8)0.063 (9)0.015 (6)0.004 (7)0.015 (6)
C350.091 (10)0.109 (13)0.058 (9)0.012 (8)−0.020 (8)0.005 (8)
C360.085 (9)0.134 (16)0.074 (10)−0.019 (10)0.004 (8)−0.043 (10)
C370.092 (10)0.084 (10)0.088 (10)−0.024 (8)0.012 (9)−0.039 (10)
C380.093 (8)0.039 (7)0.083 (9)−0.013 (6)0.001 (7)−0.002 (6)

Geometric parameters (Å, °)

O1—C51.263 (12)C16—H160.9300
O2—C91.232 (12)C17—C181.328 (16)
O3—C241.225 (11)C17—H170.9300
O4—C281.239 (13)C18—C191.376 (14)
S1—C41.674 (11)C18—H180.9300
S1—C11.683 (13)C19—H190.9300
S2—C131.667 (14)C20—C211.356 (15)
S2—C101.712 (11)C20—H200.9300
S3—C201.671 (13)C21—C221.364 (13)
S3—C231.692 (10)C21—H210.9300
S4—C291.672 (17)C22—C231.430 (12)
S4—C321.72 (2)C22—H220.9300
C1—C21.346 (14)C23—C241.445 (14)
C1—H10.9300C24—C251.488 (14)
C2—C31.380 (12)C25—C261.484 (12)
C2—H20.9300C25—H25A0.9700
C3—C41.373 (13)C25—H25B0.9700
C3—H30.9300C26—C331.536 (13)
C4—C51.404 (15)C26—C271.557 (12)
C5—C61.520 (14)C26—H260.9800
C6—C71.493 (13)C27—C281.477 (16)
C6—H6A0.9700C27—H27A0.9700
C6—H6B0.9700C27—H27B0.9700
C7—C141.489 (13)C28—C291.433 (19)
C7—C81.534 (12)C29—C301.39 (2)
C7—H70.9800C30—C311.41 (2)
C8—C91.530 (14)C30—H300.9300
C8—H8A0.9700C31—C321.35 (2)
C8—H8B0.9700C31—H310.9300
C9—C101.425 (15)C32—H320.9300
C10—C111.405 (15)C33—C341.357 (13)
C11—C121.408 (15)C33—C381.423 (13)
C11—H110.9300C34—C351.362 (14)
C12—C131.323 (15)C34—H340.9300
C12—H120.9300C35—C361.368 (16)
C13—H130.9300C35—H350.9300
C14—C151.361 (14)C36—C371.318 (15)
C14—C191.446 (14)C36—H360.9300
C15—C161.394 (15)C37—C381.379 (14)
C15—H150.9300C37—H370.9300
C16—C171.374 (17)C38—H380.9300
C4—S1—C192.5 (6)C18—C19—H19120.6
C13—S2—C1092.3 (7)C14—C19—H19120.6
C20—S3—C2391.2 (6)C21—C20—S3112.0 (10)
C29—S4—C3293.7 (10)C21—C20—H20124.0
C2—C1—S1111.3 (10)S3—C20—H20124.0
C2—C1—H1124.3C20—C21—C22116.1 (13)
S1—C1—H1124.3C20—C21—H21121.9
C1—C2—C3113.0 (12)C22—C21—H21121.9
C1—C2—H2123.5C21—C22—C23107.7 (10)
C3—C2—H2123.5C21—C22—H22126.2
C4—C3—C2112.2 (11)C23—C22—H22126.2
C4—C3—H3123.9C22—C23—C24126.2 (9)
C2—C3—H3123.9C22—C23—S3112.8 (8)
C3—C4—C5127.3 (11)C24—C23—S3120.9 (8)
C3—C4—S1110.9 (9)O3—C24—C23119.1 (11)
C5—C4—S1121.8 (10)O3—C24—C25120.0 (11)
O1—C5—C4121.0 (11)C23—C24—C25120.7 (10)
O1—C5—C6116.4 (12)C26—C25—C24116.2 (10)
C4—C5—C6122.3 (11)C26—C25—H25A108.2
C7—C6—C5117.4 (10)C24—C25—H25A108.2
C7—C6—H6A107.9C26—C25—H25B108.2
C5—C6—H6A107.9C24—C25—H25B108.2
C7—C6—H6B107.9H25A—C25—H25B107.4
C5—C6—H6B107.9C25—C26—C33114.4 (9)
H6A—C6—H6B107.2C25—C26—C27109.6 (8)
C14—C7—C6115.2 (9)C33—C26—C27110.7 (8)
C14—C7—C8110.6 (9)C25—C26—H26107.3
C6—C7—C8110.2 (9)C33—C26—H26107.3
C14—C7—H7106.8C27—C26—H26107.3
C6—C7—H7106.8C28—C27—C26116.3 (10)
C8—C7—H7106.8C28—C27—H27A108.2
C9—C8—C7114.1 (9)C26—C27—H27A108.2
C9—C8—H8A108.7C28—C27—H27B108.2
C7—C8—H8A108.7C26—C27—H27B108.2
C9—C8—H8B108.7H27A—C27—H27B107.4
C7—C8—H8B108.7O4—C28—C29117.4 (15)
H8A—C8—H8B107.6O4—C28—C27117.9 (13)
O2—C9—C10120.7 (11)C29—C28—C27124.6 (15)
O2—C9—C8119.5 (11)C30—C29—C28123.0 (19)
C10—C9—C8119.6 (11)C30—C29—S4112.8 (14)
C11—C10—C9129.3 (11)C28—C29—S4124.1 (17)
C11—C10—S2110.6 (10)C29—C30—C31108 (2)
C9—C10—S2119.9 (10)C29—C30—H30126.1
C10—C11—C12109.5 (12)C31—C30—H30126.1
C10—C11—H11125.2C32—C31—C30118 (2)
C12—C11—H11125.2C32—C31—H31120.9
C13—C12—C11114.8 (14)C30—C31—H31120.9
C13—C12—H12122.6C31—C32—S4107.4 (15)
C11—C12—H12122.6C31—C32—H32126.3
C12—C13—S2112.7 (11)S4—C32—H32126.3
C12—C13—H13123.7C34—C33—C38118.0 (10)
S2—C13—H13123.7C34—C33—C26123.2 (10)
C15—C14—C19116.2 (11)C38—C33—C26118.8 (10)
C15—C14—C7122.8 (11)C33—C34—C35122.4 (11)
C19—C14—C7120.9 (11)C33—C34—H34118.8
C14—C15—C16122.4 (12)C35—C34—H34118.8
C14—C15—H15118.8C34—C35—C36119.1 (13)
C16—C15—H15118.8C34—C35—H35120.5
C17—C16—C15120.3 (14)C36—C35—H35120.5
C17—C16—H16119.9C37—C36—C35119.9 (14)
C15—C16—H16119.9C37—C36—H36120.1
C18—C17—C16118.4 (14)C35—C36—H36120.1
C18—C17—H17120.8C36—C37—C38123.3 (14)
C16—C17—H17120.8C36—C37—H37118.3
C17—C18—C19123.8 (13)C38—C37—H37118.3
C17—C18—H18118.1C37—C38—C33117.0 (11)
C19—C18—H18118.1C37—C38—H38121.5
C18—C19—C14118.7 (12)C33—C38—H38121.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C21—H21···O4i0.932.583.407 (16)149
C1—H1···O2ii0.932.543.279 (15)137

Symmetry codes: (i) −x+1/2, y−1/2, z+1/2; (ii) −x+1, −y+1, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2395).

References

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