Acta Cryst. (2010). E66, o795 [ doi:10.1107/S1600536810008755 ]
In the title compound, C14H16N2S2, the C atoms of the aromatic ring, the two cyanide groups and the two S atoms of the isopropylsulfanyl groups are almost coplanar [maximum deviation from the mean plane = 0.042 (7) Å]. In the crystal, inversion dimers linked by aromatic ![[pi]](/logos/entities/pi_rmgif.gif)
- stacking occur, with a centroid-centroid separation of 3.7543 (8) Å.
The title compound was prepared according to the literature (Rey et al., 1998) and colourless plates of (I) were recrystallized from ethanol solution.
All H-atoms bound to carbon were refined using a riding model with distance C—H = 0.93 Å, Uiso = 1.2Ueq (C) for aromatic atoms, C—H = 0.98 Å, Uiso = 1.2Ueq (C) for methenyl atoms, and C—H = 0.96 Å, Uiso = 1.5Ueq (C) for methyl atoms.
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./hb5352fig1thm.gif)
| Fig. 1. A view of (I) with displacement ellipsoids are drawn at the 30% probability level. |
| C14H16N2S2 | F(000) = 584 |
| Mr = 276.41 | Dx = 1.218 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 4590 reflections |
| a = 10.4929 (7) Å | θ = 2.5–27.4° |
| b = 9.3613 (6) Å | µ = 0.34 mm−1 |
| c = 15.4491 (11) Å | T = 298 K |
| β = 96.467 (1)° | Plate, colorless |
| V = 1507.87 (18) Å3 | 0.20 × 0.12 × 0.05 mm |
| Z = 4 |
| Bruker APEXII CCD area-detector diffractometer | 2653 independent reflections |
| Radiation source: fine-focus sealed tube | 2371 reflections with I > 2σ(I) |
| graphite | Rint = 0.016 |
| Detector resolution: 0 pixels mm-1 | θmax = 25.0°, θmin = 2.2° |
| ω scans | h = −12→9 |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | k = −11→11 |
| Tmin = 0.936, Tmax = 0.983 | l = −17→18 |
| 7215 measured reflections |
| 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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.083 | H-atom parameters constrained |
| S = 1.05 | w = 1/[σ2(Fo2) + (0.0476P)2 + 0.2613P] where P = (Fo2 + 2Fc2)/3 |
| 2653 reflections | (Δ/σ)max = 0.001 |
| 163 parameters | Δρmax = 0.15 e Å−3 |
| 0 restraints | Δρmin = −0.20 e Å−3 |
| C14H16N2S2 | V = 1507.87 (18) Å3 |
| Mr = 276.41 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 10.4929 (7) Å | µ = 0.34 mm−1 |
| b = 9.3613 (6) Å | T = 298 K |
| c = 15.4491 (11) Å | 0.20 × 0.12 × 0.05 mm |
| β = 96.467 (1)° |
| Bruker APEXII CCD area-detector diffractometer | 2653 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2371 reflections with I > 2σ(I) |
| Tmin = 0.936, Tmax = 0.983 | Rint = 0.016 |
| 7215 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
| wR(F2) = 0.083 | Δρmax = 0.15 e Å−3 |
| S = 1.05 | Δρmin = −0.20 e Å−3 |
| 2653 reflections | Absolute structure: ? |
| 163 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
| S1 | 0.19579 (3) | −0.17837 (4) | 0.39373 (3) | 0.05107 (14) | |
| S2 | 0.31036 (3) | 0.05041 (4) | 0.51139 (2) | 0.04640 (14) | |
| C1 | −0.02406 (13) | 0.23666 (15) | 0.41156 (9) | 0.0420 (3) | |
| C4 | 0.10593 (12) | −0.02113 (15) | 0.39674 (9) | 0.0374 (3) | |
| C5 | 0.16133 (12) | 0.08841 (14) | 0.45253 (8) | 0.0362 (3) | |
| C6 | 0.09506 (13) | 0.21542 (15) | 0.45910 (9) | 0.0418 (3) | |
| H6 | 0.1307 | 0.2873 | 0.4957 | 0.050* | |
| C3 | −0.01420 (13) | 0.00042 (16) | 0.35047 (9) | 0.0416 (3) | |
| H3 | −0.0515 | −0.0718 | 0.3148 | 0.050* | |
| C2 | −0.07884 (13) | 0.12884 (16) | 0.35707 (9) | 0.0408 (3) | |
| C13 | 0.35421 (14) | 0.20982 (16) | 0.57640 (9) | 0.0448 (3) | |
| H13 | 0.2780 | 0.2470 | 0.6001 | 0.054* | |
| C7 | −0.08952 (15) | 0.37074 (18) | 0.41839 (11) | 0.0538 (4) | |
| C14 | 0.45028 (15) | 0.1574 (2) | 0.65105 (10) | 0.0583 (4) | |
| H14A | 0.4111 | 0.0850 | 0.6832 | 0.088* | |
| H14B | 0.4762 | 0.2360 | 0.6890 | 0.088* | |
| H14C | 0.5240 | 0.1184 | 0.6280 | 0.088* | |
| N1 | −0.14093 (17) | 0.47715 (17) | 0.42345 (12) | 0.0778 (5) | |
| C10 | 0.10888 (15) | −0.29469 (16) | 0.31245 (10) | 0.0471 (4) | |
| H10 | 0.0191 | −0.3013 | 0.3240 | 0.057* | |
| C8 | −0.20085 (14) | 0.15434 (18) | 0.30676 (10) | 0.0507 (4) | |
| N2 | −0.29515 (14) | 0.1806 (2) | 0.26646 (11) | 0.0752 (5) | |
| C12 | 0.4102 (2) | 0.3253 (2) | 0.52361 (13) | 0.0714 (5) | |
| H12A | 0.3471 | 0.3552 | 0.4773 | 0.107* | |
| H12B | 0.4840 | 0.2887 | 0.4995 | 0.107* | |
| H12C | 0.4349 | 0.4054 | 0.5605 | 0.107* | |
| C11 | 0.1728 (2) | −0.43966 (18) | 0.32843 (14) | 0.0722 (5) | |
| H11A | 0.1680 | −0.4681 | 0.3877 | 0.108* | |
| H11B | 0.2610 | −0.4333 | 0.3179 | 0.108* | |
| H11C | 0.1296 | −0.5090 | 0.2898 | 0.108* | |
| C9 | 0.1141 (2) | −0.2436 (2) | 0.22038 (12) | 0.0700 (5) | |
| H9A | 0.0734 | −0.1519 | 0.2130 | 0.105* | |
| H9B | 0.0702 | −0.3106 | 0.1805 | 0.105* | |
| H9C | 0.2019 | −0.2358 | 0.2091 | 0.105* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0376 (2) | 0.0453 (2) | 0.0673 (3) | 0.00601 (15) | −0.00753 (17) | −0.01699 (17) |
| S2 | 0.0365 (2) | 0.0456 (2) | 0.0536 (2) | 0.00658 (15) | −0.01006 (16) | −0.00971 (16) |
| C1 | 0.0399 (7) | 0.0423 (8) | 0.0430 (7) | 0.0060 (6) | 0.0014 (6) | 0.0032 (6) |
| C4 | 0.0323 (7) | 0.0402 (7) | 0.0398 (7) | −0.0001 (5) | 0.0044 (5) | −0.0015 (6) |
| C5 | 0.0315 (7) | 0.0403 (7) | 0.0363 (7) | 0.0011 (5) | 0.0020 (5) | −0.0001 (5) |
| C6 | 0.0409 (8) | 0.0401 (8) | 0.0426 (8) | 0.0028 (6) | −0.0031 (6) | −0.0029 (6) |
| C3 | 0.0354 (7) | 0.0453 (8) | 0.0433 (7) | −0.0034 (6) | 0.0005 (6) | −0.0035 (6) |
| C2 | 0.0320 (7) | 0.0489 (8) | 0.0406 (7) | 0.0008 (6) | 0.0005 (6) | 0.0062 (6) |
| C13 | 0.0383 (7) | 0.0513 (9) | 0.0434 (8) | 0.0002 (6) | −0.0017 (6) | −0.0117 (6) |
| C7 | 0.0507 (9) | 0.0505 (9) | 0.0569 (9) | 0.0110 (7) | −0.0083 (7) | 0.0004 (7) |
| C14 | 0.0425 (8) | 0.0797 (12) | 0.0499 (9) | 0.0037 (8) | −0.0078 (7) | −0.0122 (8) |
| N1 | 0.0790 (11) | 0.0594 (10) | 0.0895 (12) | 0.0271 (9) | −0.0150 (9) | −0.0073 (8) |
| C10 | 0.0425 (8) | 0.0420 (8) | 0.0561 (9) | −0.0071 (6) | 0.0025 (6) | −0.0093 (7) |
| C8 | 0.0384 (8) | 0.0609 (10) | 0.0513 (9) | 0.0004 (7) | −0.0022 (7) | 0.0051 (7) |
| N2 | 0.0455 (8) | 0.1017 (13) | 0.0736 (10) | 0.0064 (8) | −0.0150 (7) | 0.0103 (9) |
| C12 | 0.0734 (13) | 0.0612 (11) | 0.0777 (13) | −0.0156 (9) | 0.0006 (10) | 0.0011 (9) |
| C11 | 0.0770 (13) | 0.0440 (10) | 0.0921 (14) | 0.0008 (9) | −0.0066 (11) | −0.0183 (9) |
| C9 | 0.0839 (13) | 0.0701 (12) | 0.0574 (10) | −0.0124 (10) | 0.0142 (9) | −0.0105 (9) |
| S1—C4 | 1.7515 (14) | C7—N1 | 1.140 (2) |
| S1—C10 | 1.8265 (15) | C14—H14A | 0.9600 |
| S2—C5 | 1.7545 (13) | C14—H14B | 0.9600 |
| S2—C13 | 1.8284 (15) | C14—H14C | 0.9600 |
| C1—C6 | 1.3909 (19) | C10—C9 | 1.507 (2) |
| C1—C2 | 1.396 (2) | C10—C11 | 1.521 (2) |
| C1—C7 | 1.440 (2) | C10—H10 | 0.9800 |
| C4—C3 | 1.3920 (19) | C8—N2 | 1.135 (2) |
| C4—C5 | 1.4211 (19) | C12—H12A | 0.9600 |
| C5—C6 | 1.3868 (19) | C12—H12B | 0.9600 |
| C6—H6 | 0.9300 | C12—H12C | 0.9600 |
| C3—C2 | 1.390 (2) | C11—H11A | 0.9600 |
| C3—H3 | 0.9300 | C11—H11B | 0.9600 |
| C2—C8 | 1.441 (2) | C11—H11C | 0.9600 |
| C13—C12 | 1.512 (2) | C9—H9A | 0.9600 |
| C13—C14 | 1.525 (2) | C9—H9B | 0.9600 |
| C13—H13 | 0.9800 | C9—H9C | 0.9600 |
| C4—S1—C10 | 106.90 (7) | H14A—C14—H14B | 109.5 |
| C5—S2—C13 | 105.88 (7) | C13—C14—H14C | 109.5 |
| C6—C1—C2 | 119.97 (13) | H14A—C14—H14C | 109.5 |
| C6—C1—C7 | 119.57 (13) | H14B—C14—H14C | 109.5 |
| C2—C1—C7 | 120.46 (13) | C9—C10—C11 | 111.96 (15) |
| C3—C4—C5 | 119.46 (13) | C9—C10—S1 | 113.04 (11) |
| C3—C4—S1 | 124.56 (11) | C11—C10—S1 | 104.09 (11) |
| C5—C4—S1 | 115.97 (10) | C9—C10—H10 | 109.2 |
| C6—C5—C4 | 119.26 (12) | C11—C10—H10 | 109.2 |
| C6—C5—S2 | 124.12 (10) | S1—C10—H10 | 109.2 |
| C4—C5—S2 | 116.61 (10) | N2—C8—C2 | 176.87 (19) |
| C5—C6—C1 | 120.80 (13) | C13—C12—H12A | 109.5 |
| C5—C6—H6 | 119.6 | C13—C12—H12B | 109.5 |
| C1—C6—H6 | 119.6 | H12A—C12—H12B | 109.5 |
| C2—C3—C4 | 120.59 (13) | C13—C12—H12C | 109.5 |
| C2—C3—H3 | 119.7 | H12A—C12—H12C | 109.5 |
| C4—C3—H3 | 119.7 | H12B—C12—H12C | 109.5 |
| C3—C2—C1 | 119.90 (12) | C10—C11—H11A | 109.5 |
| C3—C2—C8 | 121.00 (14) | C10—C11—H11B | 109.5 |
| C1—C2—C8 | 119.08 (13) | H11A—C11—H11B | 109.5 |
| C12—C13—C14 | 111.97 (14) | C10—C11—H11C | 109.5 |
| C12—C13—S2 | 112.10 (11) | H11A—C11—H11C | 109.5 |
| C14—C13—S2 | 104.90 (11) | H11B—C11—H11C | 109.5 |
| C12—C13—H13 | 109.3 | C10—C9—H9A | 109.5 |
| C14—C13—H13 | 109.3 | C10—C9—H9B | 109.5 |
| S2—C13—H13 | 109.3 | H9A—C9—H9B | 109.5 |
| N1—C7—C1 | 179.6 (2) | C10—C9—H9C | 109.5 |
| C13—C14—H14A | 109.5 | H9A—C9—H9C | 109.5 |
| C13—C14—H14B | 109.5 | H9B—C9—H9C | 109.5 |
This work was supported by the Postdoctoral Scientific Foundation of China (grant No. 20070411093), the Postdoctoral Scientific Foundation of Shandong Province (grant No. 200603070) and the Independent Innovation Foundation of Shandong University, IIFSDU.
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As part of our ongoing studies of phthalocyanines (Zhang et al., 2009), we now report the synthesis and structure of the title compound, (I).
As shown in the Fig. 1, the aromatic carbon atoms, two nitrogen atoms and two carbon atoms of two cyanide groups, and two sulfur atoms in the substituted isopropylthio groups build the main skeleton for (I). The skeleton is almost planar with the maximum deviation from the mean plane of 0.042 (7) Å. The bond distances of cyanide groups are consistent with those in similar compounds (Zhang et al., 2009).
In the crystal, inversion dimers (–x, –y, 1–z) linked by aromatic π-π stacking occur, with a centroid-centroid separation of 3.7543 (8)Å.