




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808014712/ci2597sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808014712/ci2597Isup2.hkl |
CCDC reference: 690992
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.088
- wR factor = 0.205
- Data-to-parameter ratio = 21.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.12 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT480_ALERT_4_C Long H...A H-Bond Reported H18B .. S1 .. 2.99 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
All starting materials were of reagent grade and used without further purification. 1,2-Bis(undecylthio)benzene was prepared by a literature procedure (Salvatore et al., 2005): Benzene-1,2-dithiol (1 mmol) was stirred under argon atmosphere at temperature for 1 h in the presence of caesium carbonate (2.2 mmol), tetrabutylammonium iodide (TBAI; 2.2 mmol) and anhydrous DMF. The reaction mixture was subsequently cooled to 273 K, added with undecylbromide (2.2 mmol), and the reaction mixture stirred for 2 h and then allowed to return to room temperature. The title compound was obtained by slow evaporation method from the reaction mixture at room temperature. White needle-shaped crystals of suitable size for X-ray diffraction were obtained. 1H NMR (CDCl3): δ 0.88 (t, J = 6.7, 6H), 1.26–1.44 (m, 32H), 1.66 (quin, J = 7.3, 4H), 2.90 (t, J = 7.4, 4H), 7.11–7.14 (m, 2H), 7.24–7.27 (m, 2H). 13C NMR (CDCl3): δ 14.1, 22.7, 28.8, 29.0, 29.2, 29.3, 29.5, 29.6, 31.9, 33.2, 125.9, 128.5, 137.2.
All H atoms were positioned geometrically and allowed to ride on their attached atoms, with C-H = 0.95–0.99 Å and Uiso = 1.2Ueq(C) or 1.5Ueq(methyl C).
Data collection: SMART (Bruker, 2001); 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: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), KENX (Sakai, 2002), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006).
C28H50S2 | F(000) = 1000 |
Mr = 450.80 | Dx = 1.110 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3006 reflections |
a = 5.4024 (10) Å | θ = 2.4–27.7° |
b = 16.863 (3) Å | µ = 0.21 mm−1 |
c = 29.611 (5) Å | T = 100 K |
β = 91.245 (3)° | Needle, white |
V = 2696.9 (8) Å3 | 0.55 × 0.11 × 0.10 mm |
Z = 4 |
Bruker SMART APEX CCD-detector diffractometer | 5958 independent reflections |
Radiation source: fine-focus sealed tube | 4452 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.086 |
Detector resolution: 8.366 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −6→5 |
Absorption correction: analytical (XPREP; Bruker 2000) | k = −21→21 |
Tmin = 0.901, Tmax = 0.991 | l = −24→37 |
15683 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)] = 0.088 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.205 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0976P)2] where P = (Fo2 + 2Fc2)/3 |
5958 reflections | (Δ/σ)max = 0.001 |
273 parameters | Δρmax = 0.75 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
C28H50S2 | V = 2696.9 (8) Å3 |
Mr = 450.80 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.4024 (10) Å | µ = 0.21 mm−1 |
b = 16.863 (3) Å | T = 100 K |
c = 29.611 (5) Å | 0.55 × 0.11 × 0.10 mm |
β = 91.245 (3)° |
Bruker SMART APEX CCD-detector diffractometer | 5958 independent reflections |
Absorption correction: analytical (XPREP; Bruker 2000) | 4452 reflections with I > 2σ(I) |
Tmin = 0.901, Tmax = 0.991 | Rint = 0.086 |
15683 measured reflections |
R[F2 > 2σ(F2)] = 0.088 | 0 restraints |
wR(F2) = 0.205 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.75 e Å−3 |
5958 reflections | Δρmin = −0.55 e Å−3 |
273 parameters |
Experimental. The first 50 frames were rescanned at the end of data collection to evaluate any possible decay phenomenon. Since it was judged to be negligible, no decay correction was applied to the data. |
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. Mean-plane data from final SHELXL refinement run:- Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 3.2338 (0.0068) x - 0.2627 (0.0262) y + 24.0951 (0.0272) z = 10.3067 (0.0188) * -0.0131 (0.0025) C1 * 0.0083 (0.0027) C2 * 0.0004 (0.0029) C3 * -0.0044 (0.0028) C4 * -0.0004 (0.0026) C5 * 0.0092 (0.0026) C6 Rms deviation of fitted atoms = 0.0076 1.5719 (0.0210) x + 16.1263 (0.0188) y + 0.6605 (0.0846) z = 2.7127 (0.0343) Angle to previous plane (with approximate e.s.d.) = 80.44 (0.21) * 0.0000 (0.0001) S2 * 0.0000 (0.0000) C18 * 0.0000 (0.0000) C19 Rms deviation of fitted atoms = 0.0000 |
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 | ||
C1 | 0.3636 (6) | 0.23339 (18) | 0.47850 (11) | 0.0143 (7) | |
C2 | 0.3445 (6) | 0.31584 (19) | 0.47775 (11) | 0.0177 (7) | |
H2 | 0.2129 | 0.3404 | 0.4611 | 0.021* | |
C3 | 0.5152 (6) | 0.36204 (19) | 0.50091 (12) | 0.0206 (8) | |
H3 | 0.5028 | 0.4182 | 0.4998 | 0.025* | |
C4 | 0.7044 (6) | 0.3267 (2) | 0.52580 (11) | 0.0196 (7) | |
H4 | 0.8218 | 0.3588 | 0.5417 | 0.024* | |
C5 | 0.7236 (6) | 0.24514 (19) | 0.52766 (11) | 0.0172 (7) | |
H5 | 0.8540 | 0.2213 | 0.5449 | 0.021* | |
C6 | 0.5529 (6) | 0.19786 (18) | 0.50448 (10) | 0.0126 (6) | |
C7 | −0.0418 (6) | 0.23663 (19) | 0.41612 (11) | 0.0161 (7) | |
H7A | −0.1406 | 0.2689 | 0.4370 | 0.019* | |
H7B | 0.0570 | 0.2729 | 0.3973 | 0.019* | |
C8 | −0.2111 (6) | 0.18638 (19) | 0.38639 (11) | 0.0156 (7) | |
H8A | −0.3070 | 0.1502 | 0.4057 | 0.019* | |
H8B | −0.1091 | 0.1534 | 0.3663 | 0.019* | |
C9 | −0.3894 (6) | 0.23563 (19) | 0.35769 (11) | 0.0160 (7) | |
H9A | −0.4946 | 0.2674 | 0.3778 | 0.019* | |
H9B | −0.2933 | 0.2730 | 0.3391 | 0.019* | |
C10 | −0.5543 (6) | 0.18594 (19) | 0.32679 (11) | 0.0166 (7) | |
H10A | −0.6531 | 0.1496 | 0.3455 | 0.020* | |
H10B | −0.4486 | 0.1531 | 0.3073 | 0.020* | |
C11 | −0.7305 (6) | 0.23463 (19) | 0.29673 (11) | 0.0165 (7) | |
H11A | −0.8384 | 0.2668 | 0.3162 | 0.020* | |
H11B | −0.6320 | 0.2716 | 0.2784 | 0.020* | |
C12 | −0.8924 (6) | 0.1844 (2) | 0.26526 (11) | 0.0175 (7) | |
H12A | −0.7845 | 0.1524 | 0.2458 | 0.021* | |
H12B | −0.9904 | 0.1473 | 0.2836 | 0.021* | |
C13 | −1.0683 (6) | 0.23277 (19) | 0.23545 (11) | 0.0171 (7) | |
H13A | −1.1768 | 0.2645 | 0.2550 | 0.021* | |
H13B | −0.9702 | 0.2702 | 0.2173 | 0.021* | |
C14 | −1.2293 (6) | 0.18315 (19) | 0.20373 (11) | 0.0167 (7) | |
H14A | −1.3252 | 0.1451 | 0.2219 | 0.020* | |
H14B | −1.1208 | 0.1521 | 0.1838 | 0.020* | |
C15 | −1.4082 (6) | 0.2314 (2) | 0.17450 (11) | 0.0174 (7) | |
H15A | −1.3129 | 0.2701 | 0.1567 | 0.021* | |
H15B | −1.5193 | 0.2616 | 0.1943 | 0.021* | |
C16 | −1.5645 (6) | 0.1807 (2) | 0.14234 (11) | 0.0203 (8) | |
H16A | −1.6564 | 0.1411 | 0.1601 | 0.024* | |
H16B | −1.4533 | 0.1514 | 0.1221 | 0.024* | |
C17 | −1.7491 (7) | 0.2284 (2) | 0.11360 (12) | 0.0247 (8) | |
H17A | −1.8648 | 0.2558 | 0.1333 | 0.037* | |
H17B | −1.8413 | 0.1926 | 0.0933 | 0.037* | |
H17C | −1.6598 | 0.2675 | 0.0957 | 0.037* | |
C18 | 0.8229 (6) | 0.06584 (19) | 0.53962 (10) | 0.0147 (7) | |
H18A | 0.8749 | 0.0117 | 0.5311 | 0.018* | |
H18B | 0.9610 | 0.1021 | 0.5327 | 0.018* | |
C19 | 0.7839 (6) | 0.06751 (19) | 0.58997 (11) | 0.0151 (7) | |
H19A | 0.6565 | 0.0280 | 0.5979 | 0.018* | |
H19B | 0.7241 | 0.1206 | 0.5990 | 0.018* | |
C20 | 1.0263 (6) | 0.04874 (19) | 0.61545 (11) | 0.0169 (7) | |
H20A | 1.0864 | −0.0037 | 0.6055 | 0.020* | |
H20B | 1.1518 | 0.0886 | 0.6071 | 0.020* | |
C21 | 1.0057 (6) | 0.04781 (19) | 0.66646 (11) | 0.0182 (7) | |
H21A | 0.9020 | 0.0022 | 0.6753 | 0.022* | |
H21B | 0.9214 | 0.0969 | 0.6762 | 0.022* | |
C22 | 1.2558 (6) | 0.0419 (2) | 0.69080 (11) | 0.0172 (7) | |
H22A | 1.3383 | −0.0074 | 0.6811 | 0.021* | |
H22B | 1.3597 | 0.0870 | 0.6813 | 0.021* | |
C23 | 1.2446 (6) | 0.04204 (19) | 0.74200 (11) | 0.0190 (7) | |
H23A | 1.1481 | −0.0046 | 0.7517 | 0.023* | |
H23B | 1.1555 | 0.0902 | 0.7518 | 0.023* | |
C24 | 1.4977 (6) | 0.0400 (2) | 0.76552 (11) | 0.0182 (7) | |
H24A | 1.5864 | −0.0082 | 0.7558 | 0.022* | |
H24B | 1.5943 | 0.0865 | 0.7556 | 0.022* | |
C25 | 1.4887 (6) | 0.0404 (2) | 0.81672 (11) | 0.0188 (7) | |
H25A | 1.3865 | −0.0049 | 0.8266 | 0.023* | |
H25B | 1.4065 | 0.0897 | 0.8266 | 0.023* | |
C26 | 1.7422 (6) | 0.0350 (2) | 0.83994 (11) | 0.0194 (7) | |
H26A | 1.8269 | −0.0133 | 0.8292 | 0.023* | |
H26B | 1.8421 | 0.0813 | 0.8309 | 0.023* | |
C27 | 1.7338 (7) | 0.0323 (2) | 0.89105 (12) | 0.0243 (8) | |
H27A | 1.6665 | 0.0831 | 0.9022 | 0.029* | |
H27B | 1.6197 | −0.0105 | 0.9001 | 0.029* | |
C28 | 1.9854 (7) | 0.0181 (2) | 0.91318 (13) | 0.0298 (9) | |
H28A | 2.0508 | −0.0330 | 0.9031 | 0.045* | |
H28B | 1.9693 | 0.0176 | 0.9461 | 0.045* | |
H28C | 2.0989 | 0.0606 | 0.9046 | 0.045* | |
S1 | 0.16106 (14) | 0.17012 (5) | 0.44775 (3) | 0.0151 (2) | |
S2 | 0.55814 (15) | 0.09312 (5) | 0.50441 (3) | 0.0171 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0147 (16) | 0.0167 (16) | 0.0114 (17) | −0.0035 (13) | −0.0017 (12) | 0.0033 (13) |
C2 | 0.0188 (17) | 0.0186 (17) | 0.0156 (18) | 0.0018 (14) | −0.0028 (13) | 0.0007 (14) |
C3 | 0.0254 (18) | 0.0135 (17) | 0.0228 (19) | 0.0004 (14) | −0.0050 (14) | −0.0015 (14) |
C4 | 0.0227 (17) | 0.0221 (18) | 0.0137 (17) | −0.0030 (14) | −0.0066 (13) | −0.0013 (14) |
C5 | 0.0180 (17) | 0.0187 (17) | 0.0149 (17) | 0.0012 (13) | −0.0027 (13) | 0.0018 (13) |
C6 | 0.0147 (15) | 0.0123 (15) | 0.0109 (16) | −0.0034 (12) | −0.0017 (12) | 0.0021 (12) |
C7 | 0.0131 (16) | 0.0191 (17) | 0.0160 (18) | 0.0021 (13) | −0.0040 (12) | 0.0025 (13) |
C8 | 0.0166 (16) | 0.0161 (16) | 0.0139 (17) | 0.0007 (13) | −0.0045 (13) | −0.0011 (13) |
C9 | 0.0153 (16) | 0.0156 (16) | 0.0169 (18) | 0.0011 (13) | −0.0027 (13) | 0.0024 (13) |
C10 | 0.0137 (16) | 0.0195 (17) | 0.0163 (18) | 0.0010 (13) | −0.0050 (13) | −0.0014 (13) |
C11 | 0.0141 (16) | 0.0189 (17) | 0.0163 (18) | −0.0008 (13) | −0.0022 (13) | 0.0003 (13) |
C12 | 0.0157 (16) | 0.0210 (18) | 0.0157 (18) | −0.0016 (13) | −0.0041 (13) | 0.0011 (14) |
C13 | 0.0144 (16) | 0.0204 (17) | 0.0164 (18) | −0.0026 (13) | −0.0041 (13) | 0.0013 (14) |
C14 | 0.0155 (16) | 0.0190 (17) | 0.0155 (18) | −0.0002 (13) | −0.0038 (13) | 0.0006 (13) |
C15 | 0.0155 (16) | 0.0211 (17) | 0.0153 (18) | −0.0014 (13) | −0.0058 (13) | 0.0030 (13) |
C16 | 0.0206 (17) | 0.0234 (18) | 0.0165 (18) | −0.0009 (14) | −0.0083 (14) | 0.0005 (14) |
C17 | 0.0254 (19) | 0.029 (2) | 0.0190 (19) | 0.0005 (15) | −0.0125 (15) | 0.0036 (15) |
C18 | 0.0125 (15) | 0.0175 (16) | 0.0139 (17) | −0.0016 (13) | −0.0055 (12) | 0.0001 (13) |
C19 | 0.0159 (16) | 0.0152 (16) | 0.0141 (17) | 0.0024 (13) | −0.0033 (12) | 0.0016 (13) |
C20 | 0.0173 (16) | 0.0176 (17) | 0.0157 (18) | 0.0003 (13) | −0.0054 (13) | −0.0002 (13) |
C21 | 0.0222 (17) | 0.0167 (17) | 0.0154 (18) | 0.0014 (14) | −0.0043 (14) | 0.0030 (13) |
C22 | 0.0204 (17) | 0.0181 (17) | 0.0128 (17) | 0.0009 (13) | −0.0070 (13) | −0.0017 (13) |
C23 | 0.0228 (18) | 0.0155 (16) | 0.0184 (19) | 0.0007 (14) | −0.0061 (14) | 0.0017 (13) |
C24 | 0.0208 (17) | 0.0181 (17) | 0.0153 (18) | 0.0010 (14) | −0.0071 (13) | 0.0001 (13) |
C25 | 0.0218 (18) | 0.0183 (17) | 0.0160 (18) | 0.0014 (14) | −0.0052 (14) | 0.0020 (13) |
C26 | 0.0244 (18) | 0.0154 (16) | 0.0180 (19) | 0.0018 (14) | −0.0090 (14) | −0.0032 (14) |
C27 | 0.030 (2) | 0.0217 (18) | 0.020 (2) | 0.0010 (15) | −0.0054 (15) | 0.0003 (15) |
C28 | 0.039 (2) | 0.029 (2) | 0.020 (2) | 0.0013 (17) | −0.0158 (17) | 0.0016 (16) |
S1 | 0.0137 (4) | 0.0177 (4) | 0.0135 (4) | −0.0001 (3) | −0.0076 (3) | 0.0013 (3) |
S2 | 0.0189 (4) | 0.0147 (4) | 0.0173 (5) | −0.0011 (3) | −0.0110 (3) | 0.0021 (3) |
C1—C2 | 1.394 (4) | C16—C17 | 1.526 (4) |
C1—C6 | 1.401 (4) | C16—H16A | 0.99 |
C1—S1 | 1.767 (3) | C16—H16B | 0.99 |
C2—C3 | 1.379 (4) | C17—H17A | 0.98 |
C2—H2 | 0.95 | C17—H17B | 0.98 |
C3—C4 | 1.382 (4) | C17—H17C | 0.98 |
C3—H3 | 0.95 | C18—C19 | 1.511 (4) |
C4—C5 | 1.381 (4) | C18—S2 | 1.811 (3) |
C4—H4 | 0.95 | C18—H18A | 0.99 |
C5—C6 | 1.389 (4) | C18—H18B | 0.99 |
C5—H5 | 0.95 | C19—C20 | 1.530 (4) |
C6—S2 | 1.766 (3) | C19—H19A | 0.99 |
C7—C8 | 1.515 (4) | C19—H19B | 0.99 |
C7—S1 | 1.814 (3) | C20—C21 | 1.517 (4) |
C7—H7A | 0.99 | C20—H20A | 0.99 |
C7—H7B | 0.99 | C20—H20B | 0.99 |
C8—C9 | 1.518 (4) | C21—C22 | 1.521 (4) |
C8—H8A | 0.99 | C21—H21A | 0.99 |
C8—H8B | 0.99 | C21—H21B | 0.99 |
C9—C10 | 1.516 (4) | C22—C23 | 1.519 (5) |
C9—H9A | 0.99 | C22—H22A | 0.99 |
C9—H9B | 0.99 | C22—H22B | 0.99 |
C10—C11 | 1.528 (4) | C23—C24 | 1.522 (4) |
C10—H10A | 0.99 | C23—H23A | 0.99 |
C10—H10B | 0.99 | C23—H23B | 0.99 |
C11—C12 | 1.521 (4) | C24—C25 | 1.518 (4) |
C11—H11A | 0.99 | C24—H24A | 0.99 |
C11—H11B | 0.99 | C24—H24B | 0.99 |
C12—C13 | 1.520 (4) | C25—C26 | 1.521 (4) |
C12—H12A | 0.99 | C25—H25A | 0.99 |
C12—H12B | 0.99 | C25—H25B | 0.99 |
C13—C14 | 1.517 (4) | C26—C27 | 1.516 (5) |
C13—H13A | 0.99 | C26—H26A | 0.99 |
C13—H13B | 0.99 | C26—H26B | 0.99 |
C14—C15 | 1.519 (4) | C27—C28 | 1.516 (5) |
C14—H14A | 0.99 | C27—H27A | 0.99 |
C14—H14B | 0.99 | C27—H27B | 0.99 |
C15—C16 | 1.522 (4) | C28—H28A | 0.98 |
C15—H15A | 0.99 | C28—H28B | 0.98 |
C15—H15B | 0.99 | C28—H28C | 0.98 |
S2···S2i | 3.2134 (18) | ||
C2—C1—C6 | 119.2 (3) | C17—C16—H16B | 108.9 |
C2—C1—S1 | 123.3 (2) | H16A—C16—H16B | 107.7 |
C6—C1—S1 | 117.5 (2) | C16—C17—H17A | 109.5 |
C3—C2—C1 | 120.5 (3) | C16—C17—H17B | 109.5 |
C3—C2—H2 | 119.8 | H17A—C17—H17B | 109.5 |
C1—C2—H2 | 119.8 | C16—C17—H17C | 109.5 |
C2—C3—C4 | 120.1 (3) | H17A—C17—H17C | 109.5 |
C2—C3—H3 | 120.0 | H17B—C17—H17C | 109.5 |
C4—C3—H3 | 120.0 | C19—C18—S2 | 116.0 (2) |
C5—C4—C3 | 120.3 (3) | C19—C18—H18A | 108.3 |
C5—C4—H4 | 119.9 | S2—C18—H18A | 108.3 |
C3—C4—H4 | 119.9 | C19—C18—H18B | 108.3 |
C4—C5—C6 | 120.3 (3) | S2—C18—H18B | 108.3 |
C4—C5—H5 | 119.9 | H18A—C18—H18B | 107.4 |
C6—C5—H5 | 119.9 | C18—C19—C20 | 110.3 (3) |
C5—C6—C1 | 119.6 (3) | C18—C19—H19A | 109.6 |
C5—C6—S2 | 124.3 (2) | C20—C19—H19A | 109.6 |
C1—C6—S2 | 116.0 (2) | C18—C19—H19B | 109.6 |
C8—C7—S1 | 107.7 (2) | C20—C19—H19B | 109.6 |
C8—C7—H7A | 110.2 | H19A—C19—H19B | 108.1 |
S1—C7—H7A | 110.2 | C21—C20—C19 | 114.3 (3) |
C8—C7—H7B | 110.2 | C21—C20—H20A | 108.7 |
S1—C7—H7B | 110.2 | C19—C20—H20A | 108.7 |
H7A—C7—H7B | 108.5 | C21—C20—H20B | 108.7 |
C7—C8—C9 | 112.8 (3) | C19—C20—H20B | 108.7 |
C7—C8—H8A | 109.0 | H20A—C20—H20B | 107.6 |
C9—C8—H8A | 109.0 | C20—C21—C22 | 112.9 (3) |
C7—C8—H8B | 109.0 | C20—C21—H21A | 109.0 |
C9—C8—H8B | 109.0 | C22—C21—H21A | 109.0 |
H8A—C8—H8B | 107.8 | C20—C21—H21B | 109.0 |
C10—C9—C8 | 113.1 (3) | C22—C21—H21B | 109.0 |
C10—C9—H9A | 108.9 | H21A—C21—H21B | 107.8 |
C8—C9—H9A | 108.9 | C23—C22—C21 | 114.7 (3) |
C10—C9—H9B | 108.9 | C23—C22—H22A | 108.6 |
C8—C9—H9B | 108.9 | C21—C22—H22A | 108.6 |
H9A—C9—H9B | 107.8 | C23—C22—H22B | 108.6 |
C9—C10—C11 | 113.9 (3) | C21—C22—H22B | 108.6 |
C9—C10—H10A | 108.8 | H22A—C22—H22B | 107.6 |
C11—C10—H10A | 108.8 | C22—C23—C24 | 113.7 (3) |
C9—C10—H10B | 108.8 | C22—C23—H23A | 108.8 |
C11—C10—H10B | 108.8 | C24—C23—H23A | 108.8 |
H10A—C10—H10B | 107.7 | C22—C23—H23B | 108.8 |
C12—C11—C10 | 113.6 (3) | C24—C23—H23B | 108.8 |
C12—C11—H11A | 108.8 | H23A—C23—H23B | 107.7 |
C10—C11—H11A | 108.8 | C25—C24—C23 | 114.1 (3) |
C12—C11—H11B | 108.8 | C25—C24—H24A | 108.7 |
C10—C11—H11B | 108.8 | C23—C24—H24A | 108.7 |
H11A—C11—H11B | 107.7 | C25—C24—H24B | 108.7 |
C13—C12—C11 | 113.7 (3) | C23—C24—H24B | 108.7 |
C13—C12—H12A | 108.8 | H24A—C24—H24B | 107.6 |
C11—C12—H12A | 108.8 | C24—C25—C26 | 113.8 (3) |
C13—C12—H12B | 108.8 | C24—C25—H25A | 108.8 |
C11—C12—H12B | 108.8 | C26—C25—H25A | 108.8 |
H12A—C12—H12B | 107.7 | C24—C25—H25B | 108.8 |
C14—C13—C12 | 114.0 (3) | C26—C25—H25B | 108.8 |
C14—C13—H13A | 108.8 | H25A—C25—H25B | 107.7 |
C12—C13—H13A | 108.8 | C27—C26—C25 | 114.0 (3) |
C14—C13—H13B | 108.8 | C27—C26—H26A | 108.8 |
C12—C13—H13B | 108.8 | C25—C26—H26A | 108.8 |
H13A—C13—H13B | 107.7 | C27—C26—H26B | 108.8 |
C13—C14—C15 | 114.0 (3) | C25—C26—H26B | 108.8 |
C13—C14—H14A | 108.8 | H26A—C26—H26B | 107.6 |
C15—C14—H14A | 108.8 | C28—C27—C26 | 113.0 (3) |
C13—C14—H14B | 108.8 | C28—C27—H27A | 109.0 |
C15—C14—H14B | 108.8 | C26—C27—H27A | 109.0 |
H14A—C14—H14B | 107.7 | C28—C27—H27B | 109.0 |
C14—C15—C16 | 113.2 (3) | C26—C27—H27B | 109.0 |
C14—C15—H15A | 108.9 | H27A—C27—H27B | 107.8 |
C16—C15—H15A | 108.9 | C27—C28—H28A | 109.5 |
C14—C15—H15B | 108.9 | C27—C28—H28B | 109.5 |
C16—C15—H15B | 108.9 | H28A—C28—H28B | 109.5 |
H15A—C15—H15B | 107.8 | C27—C28—H28C | 109.5 |
C15—C16—C17 | 113.6 (3) | H28A—C28—H28C | 109.5 |
C15—C16—H16A | 108.9 | H28B—C28—H28C | 109.5 |
C17—C16—H16A | 108.9 | C1—S1—C7 | 104.66 (15) |
C15—C16—H16B | 108.9 | C6—S2—C18 | 105.42 (15) |
C6—C1—C2—C3 | 2.4 (5) | C13—C14—C15—C16 | 179.0 (3) |
S1—C1—C2—C3 | −177.1 (3) | C14—C15—C16—C17 | 178.6 (3) |
C1—C2—C3—C4 | −1.2 (5) | S2—C18—C19—C20 | −176.2 (2) |
C2—C3—C4—C5 | −0.1 (5) | C18—C19—C20—C21 | −179.2 (3) |
C3—C4—C5—C6 | 0.1 (5) | C19—C20—C21—C22 | −171.0 (3) |
C4—C5—C6—C1 | 1.2 (5) | C20—C21—C22—C23 | 179.1 (3) |
C4—C5—C6—S2 | −179.9 (3) | C21—C22—C23—C24 | −177.3 (3) |
C2—C1—C6—C5 | −2.4 (5) | C22—C23—C24—C25 | 179.8 (3) |
S1—C1—C6—C5 | 177.1 (3) | C23—C24—C25—C26 | 177.6 (3) |
C2—C1—C6—S2 | 178.6 (3) | C24—C25—C26—C27 | −177.9 (3) |
S1—C1—C6—S2 | −1.9 (4) | C25—C26—C27—C28 | 173.9 (3) |
S1—C7—C8—C9 | −179.5 (2) | C2—C1—S1—C7 | 3.0 (3) |
C7—C8—C9—C10 | 178.3 (3) | C6—C1—S1—C7 | −176.4 (3) |
C8—C9—C10—C11 | −178.5 (3) | C8—C7—S1—C1 | 176.4 (2) |
C9—C10—C11—C12 | 179.0 (3) | C5—C6—S2—C18 | 0.0 (3) |
C10—C11—C12—C13 | 179.8 (3) | C1—C6—S2—C18 | 179.0 (3) |
C11—C12—C13—C14 | 179.6 (3) | C19—C18—S2—C6 | 80.8 (3) |
C12—C13—C14—C15 | 179.0 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18B···S1ii | 0.99 | 2.99 | 3.749 (4) | 134 |
C7—H7A···Cg1iii | 0.99 | 2.67 | 3.567 (16) | 151 |
Symmetry codes: (ii) x+1, y, z; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C28H50S2 |
Mr | 450.80 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 5.4024 (10), 16.863 (3), 29.611 (5) |
β (°) | 91.245 (3) |
V (Å3) | 2696.9 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.55 × 0.11 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD-detector diffractometer |
Absorption correction | Analytical (XPREP; Bruker 2000) |
Tmin, Tmax | 0.901, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15683, 5958, 4452 |
Rint | 0.086 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.088, 0.205, 1.14 |
No. of reflections | 5958 |
No. of parameters | 273 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.75, −0.55 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), KENX (Sakai, 2002), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006).
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18B···S1i | 0.99 | 2.99 | 3.749 (4) | 134 |
C7—H7A···Cg1ii | 0.99 | 2.67 | 3.567 (16) | 151 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Thioethers have emerged as preeminent classes of organic compounds, which hold useful applications as key reagents in organic synthesis, bio-organic, mechanical, and heterocyclic chemistry. The coordination chemistry of dithiolate ligands has also been extensively studied (Liu et al., 2007; Alves et al., 2004; Huynh et al., 2002). In recent years, transition metal bis(dithiolene) complexes, with square-planar coordination geometry, have been used widely as building blocks for conducting and magnetic materials (Robertson & Cronin, 2002). We previously reported the crystal structure of a dithiolate complex salt (Tomiyama et al., 2007). In order to explore crystal structures of new dithiole compounds and to gain more insight into the structure-regulating ability of intermolecular S···S, C—H···S interactions, the title compound was synthesized and its structure was analysized by X-ray analysis.
The structure of the title molecule is shown in Fig. 1. The alkyl chains are in the fully extended all-trans conformation and each alkyl chain is almost perfectly planar. The C8—C7—S1—C1 and C19—C18—S2—C6 torsion angles of 176.4 (2)° and 80.8 (3)°, respectively, indicate that non-hydrogen atoms of one of the side chains is coplanar with the benzene ring, and the other chain is twisted out of the benzene plane.
In the crystal structure, an intermolecular S···S interaction [S2···S2(1-x,-y,1-z) = 3.2123 (13) Å] shorter than 3.70 Å, the sum of van der Waals radii, links the molecules into a centrosymmetric dimer (Fig. 2). The dimers are linked through weak C—H···π (between C7—H7A and benzene ring) and C—H···S interactions (Table 1) to form a column along the a axis.