Acta Cryst. (2008). E64, o853 [ doi:10.1107/S1600536808009884 ]
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 [CO = 3.279 (15) and 3.407 (16) Å] link the molecules into chains extended along the c axis.
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%.
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).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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).
![[Figure 1]](./cv2395fig1thm.gif)
| Fig. 1. Drawing of the title compound with atomic numbering scheme and 30% probability displacement ellipsoids. Hydrogen atoms are omitted for clarity. |
| C19H16O2S2 | Dx = 1.327 Mg m−3 |
| Mr = 340.44 | Mo Kα radiation λ = 0.71073 Å |
| Orthorhombic, Pna21 | Cell parameters from 1120 reflections |
| a = 27.912 (3) Å | θ = 2.9–25.0º |
| b = 5.8607 (8) Å | µ = 0.32 mm−1 |
| c = 20.841 (2) Å | T = 298 (2) K |
| V = 3409.2 (7) Å3 | Block, yellow |
| Z = 8 | 0.26 × 0.17 × 0.09 mm |
| F000 = 1424 |
| Bruker SMART CCD area-detector diffractometer | 5636 independent reflections |
| Radiation source: fine-focus sealed tube | 2006 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.120 |
| T = 298(2) K | θmax = 25.0º |
| φ and ω scans | θmin = 1.5º |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→33 |
| Tmin = 0.922, Tmax = 0.972 | k = −6→6 |
| 13190 measured reflections | l = −24→20 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-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 = 1.02 | Δρmax = 0.36 e Å−3 |
| 5636 reflections | Δρmin = −0.45 e Å−3 |
| 415 parameters | Extinction correction: none |
| 1 restraint | Absolute structure: Flack (1983), 2565 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.18 (15) |
| Secondary atom site location: difference Fourier map |
| C19H16O2S2 | V = 3409.2 (7) Å3 |
| Mr = 340.44 | Z = 8 |
| Orthorhombic, Pna21 | Mo Kα |
| a = 27.912 (3) Å | µ = 0.32 mm−1 |
| b = 5.8607 (8) Å | T = 298 (2) K |
| c = 20.841 (2) Å | 0.26 × 0.17 × 0.09 mm |
| Bruker SMART CCD area-detector diffractometer | 5636 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2006 reflections with I > 2σ(I) |
| Tmin = 0.922, Tmax = 0.972 | Rint = 0.120 |
| 13190 measured reflections |
| R[F2 > 2σ(F2)] = 0.086 | H-atom parameters constrained |
| wR(F2) = 0.192 | Δρmax = 0.36 e Å−3 |
| S = 1.02 | Δρmin = −0.45 e Å−3 |
| 5636 reflections | Absolute structure: Flack (1983), 2565 Friedel pairs |
| 415 parameters | Flack parameter: 0.18 (15) |
| 1 restraint |
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 | ||
| O1 | 0.4895 (3) | 0.4760 (15) | −0.0653 (3) | 0.100 (3) | |
| O2 | 0.5431 (3) | 0.5207 (16) | 0.1105 (5) | 0.117 (3) | |
| O3 | 0.2607 (3) | 1.1103 (14) | 0.1107 (3) | 0.093 (2) | |
| O4 | 0.2020 (3) | 0.8734 (18) | −0.0734 (4) | 0.117 (3) | |
| S1 | 0.49589 (12) | 0.5733 (5) | −0.20432 (17) | 0.0981 (11) | |
| S2 | 0.62799 (13) | 0.6688 (7) | 0.18264 (19) | 0.1168 (13) | |
| S3 | 0.25330 (11) | 1.0432 (5) | 0.24992 (17) | 0.0937 (10) | |
| S4 | 0.11681 (15) | 0.6173 (10) | −0.1171 (2) | 0.1467 (19) | |
| C1 | 0.4854 (4) | 0.772 (2) | −0.2610 (6) | 0.091 (4) | |
| H1 | 0.4894 | 0.7482 | −0.3048 | 0.109* | |
| C2 | 0.4704 (4) | 0.969 (2) | −0.2348 (6) | 0.081 (3) | |
| H2 | 0.4640 | 1.1001 | −0.2585 | 0.098* | |
| C3 | 0.4655 (4) | 0.957 (2) | −0.1689 (6) | 0.078 (3) | |
| H3 | 0.4550 | 1.0777 | −0.1436 | 0.094* | |
| C4 | 0.4779 (3) | 0.747 (2) | −0.1452 (6) | 0.064 (3) | |
| C5 | 0.4773 (4) | 0.676 (2) | −0.0809 (6) | 0.074 (3) | |
| C6 | 0.4575 (4) | 0.8254 (19) | −0.0275 (5) | 0.075 (3) | |
| H6A | 0.4648 | 0.9830 | −0.0378 | 0.089* | |
| H6B | 0.4229 | 0.8103 | −0.0276 | 0.089* | |
| C7 | 0.4748 (4) | 0.7802 (17) | 0.0391 (5) | 0.058 (3) | |
| H7 | 0.4733 | 0.6147 | 0.0455 | 0.070* | |
| C8 | 0.5276 (3) | 0.8490 (17) | 0.0456 (5) | 0.064 (3) | |
| H8A | 0.5434 | 0.8245 | 0.0047 | 0.077* | |
| H8B | 0.5293 | 1.0107 | 0.0552 | 0.077* | |
| C9 | 0.5549 (4) | 0.718 (2) | 0.0976 (6) | 0.075 (4) | |
| C10 | 0.5955 (4) | 0.820 (2) | 0.1275 (5) | 0.087 (4) | |
| C11 | 0.6126 (4) | 1.045 (2) | 0.1228 (6) | 0.090 (4) | |
| H11 | 0.5995 | 1.1584 | 0.0970 | 0.108* | |
| C12 | 0.6526 (5) | 1.072 (2) | 0.1631 (7) | 0.102 (4) | |
| H12 | 0.6699 | 1.2077 | 0.1654 | 0.123* | |
| C13 | 0.6638 (4) | 0.890 (2) | 0.1975 (6) | 0.107 (4) | |
| H13 | 0.6890 | 0.8860 | 0.2268 | 0.128* | |
| C14 | 0.4456 (3) | 0.8857 (19) | 0.0911 (6) | 0.061 (3) | |
| C15 | 0.4379 (4) | 0.782 (2) | 0.1486 (7) | 0.078 (3) | |
| H15 | 0.4512 | 0.6389 | 0.1559 | 0.093* | |
| C16 | 0.4109 (4) | 0.883 (3) | 0.1972 (7) | 0.095 (4) | |
| H16 | 0.4060 | 0.8063 | 0.2356 | 0.114* | |
| C17 | 0.3914 (5) | 1.096 (3) | 0.1884 (7) | 0.100 (5) | |
| H17 | 0.3740 | 1.1666 | 0.2210 | 0.121* | |
| C18 | 0.3979 (4) | 1.200 (2) | 0.1324 (8) | 0.088 (4) | |
| H18 | 0.3832 | 1.3399 | 0.1258 | 0.105* | |
| C19 | 0.4253 (4) | 1.1110 (19) | 0.0834 (6) | 0.083 (3) | |
| H19 | 0.4307 | 1.1945 | 0.0462 | 0.100* | |
| C20 | 0.2648 (4) | 0.857 (3) | 0.3085 (5) | 0.099 (4) | |
| H20 | 0.2570 | 0.8801 | 0.3514 | 0.119* | |
| C21 | 0.2870 (4) | 0.667 (2) | 0.2862 (7) | 0.094 (4) | |
| H21 | 0.2972 | 0.5507 | 0.3135 | 0.113* | |
| C22 | 0.2936 (3) | 0.6553 (17) | 0.2214 (4) | 0.049 (3) | |
| H22 | 0.3067 | 0.5334 | 0.1988 | 0.058* | |
| C23 | 0.2767 (3) | 0.8648 (17) | 0.1944 (5) | 0.059 (3) | |
| C24 | 0.2767 (3) | 0.925 (2) | 0.1271 (6) | 0.067 (3) | |
| C25 | 0.2983 (4) | 0.7695 (18) | 0.0785 (5) | 0.069 (3) | |
| H25A | 0.3320 | 0.8066 | 0.0746 | 0.083* | |
| H25B | 0.2961 | 0.6145 | 0.0946 | 0.083* | |
| C26 | 0.2767 (3) | 0.7758 (17) | 0.0135 (5) | 0.060 (3) | |
| H26 | 0.2717 | 0.9366 | 0.0024 | 0.072* | |
| C27 | 0.2264 (4) | 0.6603 (19) | 0.0151 (5) | 0.072 (3) | |
| H27A | 0.2310 | 0.4973 | 0.0203 | 0.087* | |
| H27B | 0.2095 | 0.7148 | 0.0527 | 0.087* | |
| C28 | 0.1956 (5) | 0.698 (3) | −0.0415 (7) | 0.090 (4) | |
| C29 | 0.1564 (5) | 0.554 (4) | −0.0595 (8) | 0.125 (6) | |
| C30 | 0.1481 (6) | 0.341 (4) | −0.0319 (8) | 0.141 (7) | |
| H30 | 0.1666 | 0.2724 | 0.0000 | 0.169* | |
| C31 | 0.1071 (6) | 0.247 (3) | −0.0608 (8) | 0.141 (7) | |
| H31 | 0.0953 | 0.1058 | −0.0480 | 0.169* | |
| C32 | 0.0852 (6) | 0.368 (3) | −0.1074 (9) | 0.144 (7) | |
| H32 | 0.0581 | 0.3241 | −0.1302 | 0.173* | |
| C33 | 0.3080 (3) | 0.6706 (19) | −0.0394 (5) | 0.054 (3) | |
| C34 | 0.3164 (4) | 0.7746 (18) | −0.0964 (6) | 0.066 (3) | |
| H34 | 0.3017 | 0.9139 | −0.1048 | 0.079* | |
| C35 | 0.3456 (5) | 0.683 (3) | −0.1420 (6) | 0.086 (4) | |
| H35 | 0.3525 | 0.7628 | −0.1793 | 0.103* | |
| C36 | 0.3646 (4) | 0.470 (3) | −0.1320 (7) | 0.098 (4) | |
| H36 | 0.3828 | 0.4010 | −0.1638 | 0.117* | |
| C37 | 0.3570 (4) | 0.364 (2) | −0.0771 (7) | 0.088 (4) | |
| H37 | 0.3719 | 0.2247 | −0.0703 | 0.106* | |
| C38 | 0.3279 (4) | 0.4499 (18) | −0.0293 (5) | 0.071 (3) | |
| H38 | 0.3216 | 0.3671 | 0.0078 | 0.086* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.139 (7) | 0.062 (6) | 0.100 (6) | 0.030 (5) | −0.003 (5) | −0.002 (5) |
| O2 | 0.103 (7) | 0.085 (7) | 0.163 (8) | −0.004 (5) | −0.025 (6) | 0.055 (6) |
| O3 | 0.127 (7) | 0.055 (6) | 0.096 (6) | −0.017 (5) | −0.016 (5) | −0.007 (5) |
| O4 | 0.072 (6) | 0.154 (10) | 0.125 (8) | 0.003 (6) | 0.026 (5) | 0.043 (7) |
| S1 | 0.127 (3) | 0.068 (2) | 0.100 (2) | 0.006 (2) | 0.014 (2) | −0.017 (2) |
| S2 | 0.098 (3) | 0.120 (3) | 0.133 (3) | 0.028 (2) | −0.036 (2) | −0.004 (3) |
| S3 | 0.102 (2) | 0.085 (2) | 0.094 (2) | 0.001 (2) | −0.003 (2) | −0.020 (2) |
| S4 | 0.077 (3) | 0.214 (5) | 0.149 (4) | −0.018 (3) | 0.024 (3) | −0.068 (4) |
| C1 | 0.115 (10) | 0.074 (10) | 0.083 (10) | −0.017 (8) | 0.020 (8) | −0.015 (8) |
| C2 | 0.108 (9) | 0.056 (9) | 0.080 (10) | 0.004 (7) | 0.004 (8) | 0.009 (7) |
| C3 | 0.091 (9) | 0.071 (10) | 0.072 (9) | 0.007 (7) | 0.003 (7) | −0.005 (8) |
| C4 | 0.046 (6) | 0.090 (11) | 0.056 (8) | −0.007 (6) | −0.005 (6) | −0.001 (7) |
| C5 | 0.063 (8) | 0.059 (8) | 0.100 (10) | 0.015 (6) | −0.009 (7) | −0.021 (8) |
| C6 | 0.074 (7) | 0.073 (8) | 0.076 (9) | 0.013 (6) | −0.008 (7) | −0.011 (7) |
| C7 | 0.068 (8) | 0.047 (7) | 0.060 (7) | −0.002 (5) | −0.008 (7) | 0.000 (5) |
| C8 | 0.062 (8) | 0.065 (8) | 0.066 (7) | −0.005 (6) | −0.004 (6) | 0.011 (6) |
| C9 | 0.042 (7) | 0.089 (10) | 0.094 (10) | 0.010 (7) | 0.009 (7) | 0.017 (8) |
| C10 | 0.067 (9) | 0.085 (10) | 0.109 (10) | 0.023 (8) | −0.022 (7) | −0.013 (8) |
| C11 | 0.077 (9) | 0.083 (10) | 0.110 (10) | 0.016 (8) | −0.016 (8) | −0.022 (8) |
| C12 | 0.091 (10) | 0.088 (11) | 0.128 (12) | 0.010 (8) | −0.020 (9) | −0.017 (9) |
| C13 | 0.087 (10) | 0.107 (12) | 0.125 (11) | 0.026 (9) | −0.024 (8) | −0.023 (10) |
| C14 | 0.056 (7) | 0.054 (8) | 0.072 (9) | −0.004 (6) | −0.015 (6) | −0.004 (7) |
| C15 | 0.083 (9) | 0.065 (8) | 0.085 (10) | −0.002 (7) | −0.014 (8) | 0.005 (8) |
| C16 | 0.068 (9) | 0.124 (14) | 0.094 (11) | −0.019 (9) | 0.000 (8) | 0.003 (10) |
| C17 | 0.076 (9) | 0.149 (16) | 0.077 (11) | −0.008 (10) | 0.008 (8) | −0.025 (11) |
| C18 | 0.076 (9) | 0.088 (10) | 0.099 (11) | 0.009 (7) | −0.006 (8) | −0.032 (10) |
| C19 | 0.105 (10) | 0.051 (9) | 0.093 (9) | −0.005 (7) | 0.002 (8) | −0.018 (7) |
| C20 | 0.076 (8) | 0.176 (15) | 0.046 (8) | 0.022 (9) | 0.006 (6) | −0.008 (9) |
| C21 | 0.073 (8) | 0.087 (10) | 0.123 (13) | −0.017 (7) | 0.022 (8) | 0.012 (10) |
| C22 | 0.067 (7) | 0.053 (7) | 0.026 (6) | −0.008 (5) | 0.001 (5) | 0.002 (5) |
| C23 | 0.052 (6) | 0.074 (8) | 0.050 (7) | 0.013 (5) | −0.011 (6) | −0.003 (6) |
| C24 | 0.054 (7) | 0.048 (8) | 0.098 (10) | −0.002 (6) | −0.006 (6) | 0.010 (8) |
| C25 | 0.074 (8) | 0.069 (8) | 0.064 (8) | −0.016 (6) | −0.002 (7) | −0.011 (6) |
| C26 | 0.052 (7) | 0.057 (7) | 0.069 (8) | −0.001 (5) | 0.004 (6) | 0.013 (6) |
| C27 | 0.066 (8) | 0.084 (9) | 0.067 (8) | −0.001 (6) | 0.004 (6) | 0.002 (6) |
| C28 | 0.091 (10) | 0.103 (11) | 0.076 (10) | −0.019 (9) | −0.007 (8) | 0.008 (8) |
| C29 | 0.057 (10) | 0.182 (19) | 0.134 (15) | 0.002 (12) | 0.018 (10) | −0.077 (14) |
| C30 | 0.078 (12) | 0.18 (2) | 0.163 (17) | 0.000 (13) | 0.018 (11) | −0.081 (15) |
| C31 | 0.079 (13) | 0.19 (2) | 0.159 (17) | −0.002 (12) | 0.017 (11) | −0.078 (15) |
| C32 | 0.080 (12) | 0.19 (2) | 0.161 (17) | 0.004 (12) | 0.023 (11) | −0.088 (14) |
| C33 | 0.046 (6) | 0.064 (8) | 0.052 (7) | 0.011 (5) | 0.002 (5) | −0.006 (6) |
| C34 | 0.075 (8) | 0.059 (8) | 0.063 (9) | 0.015 (6) | 0.004 (7) | 0.015 (6) |
| C35 | 0.091 (10) | 0.109 (13) | 0.058 (9) | 0.012 (8) | −0.020 (8) | 0.005 (8) |
| C36 | 0.085 (9) | 0.134 (16) | 0.074 (10) | −0.019 (10) | 0.004 (8) | −0.043 (10) |
| C37 | 0.092 (10) | 0.084 (10) | 0.088 (10) | −0.024 (8) | 0.012 (9) | −0.039 (10) |
| C38 | 0.093 (8) | 0.039 (7) | 0.083 (9) | −0.013 (6) | 0.001 (7) | −0.002 (6) |
| O1—C5 | 1.263 (12) | C16—H16 | 0.9300 |
| O2—C9 | 1.232 (12) | C17—C18 | 1.328 (16) |
| O3—C24 | 1.225 (11) | C17—H17 | 0.9300 |
| O4—C28 | 1.239 (13) | C18—C19 | 1.376 (14) |
| S1—C4 | 1.674 (11) | C18—H18 | 0.9300 |
| S1—C1 | 1.683 (13) | C19—H19 | 0.9300 |
| S2—C13 | 1.667 (14) | C20—C21 | 1.356 (15) |
| S2—C10 | 1.712 (11) | C20—H20 | 0.9300 |
| S3—C20 | 1.671 (13) | C21—C22 | 1.364 (13) |
| S3—C23 | 1.692 (10) | C21—H21 | 0.9300 |
| S4—C29 | 1.672 (17) | C22—C23 | 1.430 (12) |
| S4—C32 | 1.72 (2) | C22—H22 | 0.9300 |
| C1—C2 | 1.346 (14) | C23—C24 | 1.445 (14) |
| C1—H1 | 0.9300 | C24—C25 | 1.488 (14) |
| C2—C3 | 1.380 (12) | C25—C26 | 1.484 (12) |
| C2—H2 | 0.9300 | C25—H25A | 0.9700 |
| C3—C4 | 1.373 (13) | C25—H25B | 0.9700 |
| C3—H3 | 0.9300 | C26—C33 | 1.536 (13) |
| C4—C5 | 1.404 (15) | C26—C27 | 1.557 (12) |
| C5—C6 | 1.520 (14) | C26—H26 | 0.9800 |
| C6—C7 | 1.493 (13) | C27—C28 | 1.477 (16) |
| C6—H6A | 0.9700 | C27—H27A | 0.9700 |
| C6—H6B | 0.9700 | C27—H27B | 0.9700 |
| C7—C14 | 1.489 (13) | C28—C29 | 1.433 (19) |
| C7—C8 | 1.534 (12) | C29—C30 | 1.39 (2) |
| C7—H7 | 0.9800 | C30—C31 | 1.41 (2) |
| C8—C9 | 1.530 (14) | C30—H30 | 0.9300 |
| C8—H8A | 0.9700 | C31—C32 | 1.35 (2) |
| C8—H8B | 0.9700 | C31—H31 | 0.9300 |
| C9—C10 | 1.425 (15) | C32—H32 | 0.9300 |
| C10—C11 | 1.405 (15) | C33—C34 | 1.357 (13) |
| C11—C12 | 1.408 (15) | C33—C38 | 1.423 (13) |
| C11—H11 | 0.9300 | C34—C35 | 1.362 (14) |
| C12—C13 | 1.323 (15) | C34—H34 | 0.9300 |
| C12—H12 | 0.9300 | C35—C36 | 1.368 (16) |
| C13—H13 | 0.9300 | C35—H35 | 0.9300 |
| C14—C15 | 1.361 (14) | C36—C37 | 1.318 (15) |
| C14—C19 | 1.446 (14) | C36—H36 | 0.9300 |
| C15—C16 | 1.394 (15) | C37—C38 | 1.379 (14) |
| C15—H15 | 0.9300 | C37—H37 | 0.9300 |
| C16—C17 | 1.374 (17) | C38—H38 | 0.9300 |
| C4—S1—C1 | 92.5 (6) | C18—C19—H19 | 120.6 |
| C13—S2—C10 | 92.3 (7) | C14—C19—H19 | 120.6 |
| C20—S3—C23 | 91.2 (6) | C21—C20—S3 | 112.0 (10) |
| C29—S4—C32 | 93.7 (10) | C21—C20—H20 | 124.0 |
| C2—C1—S1 | 111.3 (10) | S3—C20—H20 | 124.0 |
| C2—C1—H1 | 124.3 | C20—C21—C22 | 116.1 (13) |
| S1—C1—H1 | 124.3 | C20—C21—H21 | 121.9 |
| C1—C2—C3 | 113.0 (12) | C22—C21—H21 | 121.9 |
| C1—C2—H2 | 123.5 | C21—C22—C23 | 107.7 (10) |
| C3—C2—H2 | 123.5 | C21—C22—H22 | 126.2 |
| C4—C3—C2 | 112.2 (11) | C23—C22—H22 | 126.2 |
| C4—C3—H3 | 123.9 | C22—C23—C24 | 126.2 (9) |
| C2—C3—H3 | 123.9 | C22—C23—S3 | 112.8 (8) |
| C3—C4—C5 | 127.3 (11) | C24—C23—S3 | 120.9 (8) |
| C3—C4—S1 | 110.9 (9) | O3—C24—C23 | 119.1 (11) |
| C5—C4—S1 | 121.8 (10) | O3—C24—C25 | 120.0 (11) |
| O1—C5—C4 | 121.0 (11) | C23—C24—C25 | 120.7 (10) |
| O1—C5—C6 | 116.4 (12) | C26—C25—C24 | 116.2 (10) |
| C4—C5—C6 | 122.3 (11) | C26—C25—H25A | 108.2 |
| C7—C6—C5 | 117.4 (10) | C24—C25—H25A | 108.2 |
| C7—C6—H6A | 107.9 | C26—C25—H25B | 108.2 |
| C5—C6—H6A | 107.9 | C24—C25—H25B | 108.2 |
| C7—C6—H6B | 107.9 | H25A—C25—H25B | 107.4 |
| C5—C6—H6B | 107.9 | C25—C26—C33 | 114.4 (9) |
| H6A—C6—H6B | 107.2 | C25—C26—C27 | 109.6 (8) |
| C14—C7—C6 | 115.2 (9) | C33—C26—C27 | 110.7 (8) |
| C14—C7—C8 | 110.6 (9) | C25—C26—H26 | 107.3 |
| C6—C7—C8 | 110.2 (9) | C33—C26—H26 | 107.3 |
| C14—C7—H7 | 106.8 | C27—C26—H26 | 107.3 |
| C6—C7—H7 | 106.8 | C28—C27—C26 | 116.3 (10) |
| C8—C7—H7 | 106.8 | C28—C27—H27A | 108.2 |
| C9—C8—C7 | 114.1 (9) | C26—C27—H27A | 108.2 |
| C9—C8—H8A | 108.7 | C28—C27—H27B | 108.2 |
| C7—C8—H8A | 108.7 | C26—C27—H27B | 108.2 |
| C9—C8—H8B | 108.7 | H27A—C27—H27B | 107.4 |
| C7—C8—H8B | 108.7 | O4—C28—C29 | 117.4 (15) |
| H8A—C8—H8B | 107.6 | O4—C28—C27 | 117.9 (13) |
| O2—C9—C10 | 120.7 (11) | C29—C28—C27 | 124.6 (15) |
| O2—C9—C8 | 119.5 (11) | C30—C29—C28 | 123.0 (19) |
| C10—C9—C8 | 119.6 (11) | C30—C29—S4 | 112.8 (14) |
| C11—C10—C9 | 129.3 (11) | C28—C29—S4 | 124.1 (17) |
| C11—C10—S2 | 110.6 (10) | C29—C30—C31 | 108 (2) |
| C9—C10—S2 | 119.9 (10) | C29—C30—H30 | 126.1 |
| C10—C11—C12 | 109.5 (12) | C31—C30—H30 | 126.1 |
| C10—C11—H11 | 125.2 | C32—C31—C30 | 118 (2) |
| C12—C11—H11 | 125.2 | C32—C31—H31 | 120.9 |
| C13—C12—C11 | 114.8 (14) | C30—C31—H31 | 120.9 |
| C13—C12—H12 | 122.6 | C31—C32—S4 | 107.4 (15) |
| C11—C12—H12 | 122.6 | C31—C32—H32 | 126.3 |
| C12—C13—S2 | 112.7 (11) | S4—C32—H32 | 126.3 |
| C12—C13—H13 | 123.7 | C34—C33—C38 | 118.0 (10) |
| S2—C13—H13 | 123.7 | C34—C33—C26 | 123.2 (10) |
| C15—C14—C19 | 116.2 (11) | C38—C33—C26 | 118.8 (10) |
| C15—C14—C7 | 122.8 (11) | C33—C34—C35 | 122.4 (11) |
| C19—C14—C7 | 120.9 (11) | C33—C34—H34 | 118.8 |
| C14—C15—C16 | 122.4 (12) | C35—C34—H34 | 118.8 |
| C14—C15—H15 | 118.8 | C34—C35—C36 | 119.1 (13) |
| C16—C15—H15 | 118.8 | C34—C35—H35 | 120.5 |
| C17—C16—C15 | 120.3 (14) | C36—C35—H35 | 120.5 |
| C17—C16—H16 | 119.9 | C37—C36—C35 | 119.9 (14) |
| C15—C16—H16 | 119.9 | C37—C36—H36 | 120.1 |
| C18—C17—C16 | 118.4 (14) | C35—C36—H36 | 120.1 |
| C18—C17—H17 | 120.8 | C36—C37—C38 | 123.3 (14) |
| C16—C17—H17 | 120.8 | C36—C37—H37 | 118.3 |
| C17—C18—C19 | 123.8 (13) | C38—C37—H37 | 118.3 |
| C17—C18—H18 | 118.1 | C37—C38—C33 | 117.0 (11) |
| C19—C18—H18 | 118.1 | C37—C38—H38 | 121.5 |
| C18—C19—C14 | 118.7 (12) | C33—C38—H38 | 121.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C21—H21···O4i | 0.93 | 2.58 | 3.407 (16) | 149 |
| C1—H1···O2ii | 0.93 | 2.54 | 3.279 (15) | 137 |
| Symmetry codes: (i) −x+1/2, y−1/2, z+1/2; (ii) −x+1, −y+1, z−1/2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| C21—H21···O4i | 0.93 | 2.58 | 3.407 (16) | 149 |
| C1—H1···O2ii | 0.93 | 2.54 | 3.279 (15) | 137 |
| Symmetry codes: (i) −x+1/2, y−1/2, z+1/2; (ii) −x+1, −y+1, z−1/2. |
The authors acknowledge the support of the National Natural Science Foundation of Liaocheng University (grant No. X051040).
Bose, A. K., Pednekar, S., Ganguly, S. N., Chakraborty, G. & Manhas, M. S. (2004). Tetrahedron Lett. 45, 8351–8353.
Das, G. C., Hursthouse, M. B., Malik, K. M. A., Rahman, M. M., Rahman, M. T. & Olsson, T. (1994). J. Chem. Crystallogr. 24, 511–515.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Huang, X.-Q., Wang, D.-Q., Dou, J.-M. & Wang, J.-X. (2006). Acta Cryst. E62, o60–o61.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
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.