

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810035488/ya2128sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810035488/ya2128Isup2.hkl |
CCDC reference: 797735
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.119
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT900_ALERT_1_A No Matching Reflection File Found .............. ! PLAT900_ALERT_1_A No Matching Reflection File Found .............. ! PLAT902_ALERT_1_A No (Interpretable) Reflections found in FCF .... !
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.05
Alert level G PLAT154_ALERT_1_G The su's on the Cell Angles are Equal (x 10000) 200 Deg.
3 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was synthesized in three steps. Tritylated aminothiophenol was prepared following the literature procedure (Noveron et al., 2001). Under a nitrogen atmosphere, dimethylmalonyl dichloride (0.40 ml, 2.97 mmol) was dissolved in a solution of triethylamine (0.95 g, 6.84 mmol) in 10 ml of chloroform, then added dropwise to a degassed solution of tritylated aminothiophenol (2.190 g, 5.95 mmol) and triethylamine (0.95 g, 6.84 mmol) in 10 ml of chloroform. The mixture was allowed to react for 16 h at room temperature, and then the solvent was removed under vacuum. Cold methanol was added to the tan solid, then filtered under vacuum. The precipitate was washed with cold methanol to yield a colorless solid, 2,2-dimethyl-N,N'-bis(2-(tritylthio)phenyl)malonamide (Try-DMPS). Yield: 6.02 g (71%). 1H NMR (CDCl3, 300 MHz) δ from TMS: 1.17 (s, 6H), 6.84 (t, 2H), 7.19–7.34 (m, 34H), 8.4 (d, 2H), 9.22 (s, 2H). 13C NMR (CDCl3, 75.4 MHz) δ 24.2, 51.7, 71.9, 120.3, 122.1, 123.7, 127.3, 127.9, 130.2, 131.1, 137.1, 142.5, 143.9, 170.9. Selected IR bands (KBr pellet, cm-1) 3348 (w), 3056 (w), 1688 (m), 1575 (m), 1504 (s), 1430 (m), 1297 (m), 701 (s). Try-DMPS (1.45 g, 1.75 mmol) was added to a mixture of 5 mL of trifluoroacetic acid and 3 mL of dichloromethane under stirring, and the solution instantly turned bright red. Triethylsilane (0.56 ml, 3.5 mmol) was added dropwise, with the color gradually changing from red to yellow to colorless. The solution was stirred for 15 minutes at room temperature, and then dichloromethane was removed under vacuum. The slurry was filtered to remove the triphenylmethane sideproduct, and the solvent was removed from the filtrate under vacuum to obtain a colorless solid. The solid was recrystallized twice in methanol to yield X-ray quality colorless crystals of the title compound. Yield: 1.4504 g (43%). 1H NMR (CDCl3, 300 MHz) δ from TMS: 2.18 (s, 6H), 7.36 (t, 2H), 7.41 (t, 2H), 7.85 (dd, 2H), 8.07 (d, 2H). 13C NMR (CDCl3, 75.4 MHz) δ 29.7, 47.8, 121.8, 123.5, 125.4, 126.3, 135.8, 153.1, 176.9. Selected IR bands (KBr pellet, cm-1) 3427 (w), 2986 (m), 1492 (s), 1435 (s), 1207 (s), 760 (s).
The H atoms were located in the difference map and included in the subsequent refinement with isotropic thermal parameters; C—H 0.88 (3)–1.04 (2) Å.
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![]() | Fig. 1. Asymmetric unit of the structure of the title compound with displacement ellipsoids, drawn at 50% probability level. |
C17H14N2S2 | Z = 4 |
Mr = 310.42 | F(000) = 648 |
Triclinic, P1 | Dx = 1.403 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3791 (13) Å | Cell parameters from 3754 reflections |
b = 11.8832 (15) Å | θ = 2.4–26.4° |
c = 12.3391 (15) Å | µ = 0.36 mm−1 |
α = 86.730 (2)° | T = 173 K |
β = 78.048 (2)° | Plate, colorless |
γ = 80.779 (2)° | 0.42 × 0.24 × 0.05 mm |
V = 1469.2 (3) Å3 |
Bruker APEX CCD area-detector diffractometer | 6379 independent reflections |
Radiation source: fine-focus sealed tube | 5007 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
phi and ω scans | θmax = 27.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1995) | h = −13→13 |
Tmin = 0.865, Tmax = 0.982 | k = −15→15 |
17048 measured reflections | l = −15→15 |
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)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.119 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0637P)2 + 0.1616P] where P = (Fo2 + 2Fc2)/3 |
6379 reflections | (Δ/σ)max = 0.001 |
491 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C17H14N2S2 | γ = 80.779 (2)° |
Mr = 310.42 | V = 1469.2 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.3791 (13) Å | Mo Kα radiation |
b = 11.8832 (15) Å | µ = 0.36 mm−1 |
c = 12.3391 (15) Å | T = 173 K |
α = 86.730 (2)° | 0.42 × 0.24 × 0.05 mm |
β = 78.048 (2)° |
Bruker APEX CCD area-detector diffractometer | 6379 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1995) | 5007 reflections with I > 2σ(I) |
Tmin = 0.865, Tmax = 0.982 | Rint = 0.032 |
17048 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.119 | All H-atom parameters refined |
S = 1.04 | Δρmax = 0.43 e Å−3 |
6379 reflections | Δρmin = −0.21 e Å−3 |
491 parameters |
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 | ||
S1 | 0.11702 (5) | 0.06830 (4) | 0.74433 (5) | 0.03295 (15) | |
S2 | 0.15867 (6) | 0.39956 (5) | 0.46027 (5) | 0.03744 (16) | |
N1 | 0.07371 (17) | 0.28776 (14) | 0.75471 (14) | 0.0285 (4) | |
N2 | 0.14744 (17) | 0.18478 (14) | 0.45096 (14) | 0.0274 (4) | |
C1 | −0.0143 (2) | 0.12842 (18) | 0.84422 (17) | 0.0275 (4) | |
C2 | −0.1057 (2) | 0.0764 (2) | 0.9223 (2) | 0.0364 (5) | |
C3 | −0.2036 (2) | 0.1445 (2) | 0.99230 (19) | 0.0379 (6) | |
C4 | −0.2109 (2) | 0.2623 (2) | 0.98686 (19) | 0.0378 (6) | |
C5 | −0.1214 (2) | 0.3150 (2) | 0.91101 (19) | 0.0367 (5) | |
C6 | −0.0223 (2) | 0.24736 (17) | 0.83812 (17) | 0.0264 (4) | |
C7 | 0.15016 (19) | 0.20478 (16) | 0.70011 (16) | 0.0236 (4) | |
C8 | 0.2599 (2) | 0.22277 (17) | 0.60006 (16) | 0.0258 (4) | |
C9 | 0.19052 (19) | 0.25650 (16) | 0.50325 (16) | 0.0248 (4) | |
C10 | 0.0816 (2) | 0.24018 (17) | 0.37034 (16) | 0.0267 (4) | |
C11 | 0.0191 (2) | 0.1870 (2) | 0.30272 (19) | 0.0359 (5) | |
C12 | −0.0461 (2) | 0.2534 (2) | 0.2295 (2) | 0.0428 (6) | |
C13 | −0.0488 (2) | 0.3704 (2) | 0.2221 (2) | 0.0445 (6) | |
C14 | 0.0126 (3) | 0.4251 (2) | 0.2877 (2) | 0.0413 (6) | |
C15 | 0.0782 (2) | 0.35846 (18) | 0.36298 (17) | 0.0305 (5) | |
C16 | 0.3328 (2) | 0.3175 (2) | 0.6252 (2) | 0.0349 (5) | |
C17 | 0.3583 (2) | 0.1129 (2) | 0.5719 (2) | 0.0339 (5) | |
S1' | 0.50721 (6) | 0.09629 (5) | 0.85604 (5) | 0.03416 (15) | |
S2' | 0.40874 (6) | 0.43208 (4) | 1.12466 (5) | 0.03095 (15) | |
N1' | 0.53067 (17) | 0.31085 (14) | 0.83732 (14) | 0.0276 (4) | |
N2' | 0.45605 (18) | 0.21160 (15) | 1.14371 (15) | 0.0313 (4) | |
C1' | 0.6330 (2) | 0.13756 (19) | 0.75345 (17) | 0.0324 (5) | |
C2' | 0.7266 (3) | 0.0710 (2) | 0.6744 (2) | 0.0429 (6) | |
C3' | 0.8170 (3) | 0.1245 (3) | 0.6013 (2) | 0.0497 (7) | |
C4' | 0.8160 (2) | 0.2417 (3) | 0.6045 (2) | 0.0467 (7) | |
C5' | 0.7239 (2) | 0.3082 (2) | 0.68130 (19) | 0.0389 (6) | |
C6' | 0.6309 (2) | 0.25492 (18) | 0.75653 (17) | 0.0288 (5) | |
C7' | 0.4600 (2) | 0.23898 (16) | 0.89364 (16) | 0.0245 (4) | |
C8' | 0.3426 (2) | 0.27369 (17) | 0.98818 (17) | 0.0268 (4) | |
C9' | 0.4025 (2) | 0.29371 (16) | 1.08699 (17) | 0.0256 (4) | |
C10' | 0.5093 (2) | 0.25520 (18) | 1.22437 (17) | 0.0292 (5) | |
C11' | 0.5780 (3) | 0.1898 (2) | 1.2976 (2) | 0.0395 (6) | |
C12' | 0.6284 (2) | 0.2443 (2) | 1.3717 (2) | 0.0426 (6) | |
C13' | 0.6111 (2) | 0.3625 (2) | 1.37387 (19) | 0.0390 (6) | |
C14' | 0.5442 (2) | 0.4291 (2) | 1.30219 (19) | 0.0361 (5) | |
C15' | 0.4932 (2) | 0.37455 (17) | 1.22706 (17) | 0.0278 (5) | |
C16' | 0.2577 (2) | 0.3819 (2) | 0.9530 (2) | 0.0331 (5) | |
C17' | 0.2573 (3) | 0.1780 (2) | 1.0184 (2) | 0.0368 (5) | |
H2 | −0.099 (2) | −0.002 (2) | 0.925 (2) | 0.049 (7)* | |
H2' | 0.727 (2) | −0.010 (2) | 0.6737 (18) | 0.036 (6)* | |
H3 | −0.269 (2) | 0.1105 (19) | 1.045 (2) | 0.042 (7)* | |
H3' | 0.882 (3) | 0.081 (2) | 0.553 (2) | 0.050 (7)* | |
H4 | −0.275 (2) | 0.307 (2) | 1.0317 (19) | 0.039 (7)* | |
H4' | 0.874 (3) | 0.278 (2) | 0.551 (2) | 0.066 (9)* | |
H5 | −0.127 (2) | 0.398 (2) | 0.904 (2) | 0.051 (7)* | |
H5' | 0.721 (2) | 0.3962 (19) | 0.6852 (18) | 0.038 (6)* | |
H11 | 0.023 (2) | 0.109 (2) | 0.307 (2) | 0.045 (7)* | |
H11' | 0.590 (3) | 0.115 (2) | 1.295 (2) | 0.058 (8)* | |
H12 | −0.086 (3) | 0.219 (2) | 0.181 (2) | 0.056 (8)* | |
H12' | 0.679 (2) | 0.198 (2) | 1.418 (2) | 0.045 (7)* | |
H13 | −0.091 (2) | 0.410 (2) | 0.163 (2) | 0.043 (7)* | |
H13' | 0.648 (2) | 0.3967 (18) | 1.4283 (18) | 0.033 (6)* | |
H14 | 0.009 (2) | 0.5014 (19) | 0.2881 (18) | 0.034 (6)* | |
H14' | 0.531 (2) | 0.5098 (19) | 1.3029 (18) | 0.033 (6)* | |
H16A | 0.373 (2) | 0.2928 (19) | 0.687 (2) | 0.041 (7)* | |
H16B | 0.398 (2) | 0.3325 (19) | 0.5604 (19) | 0.039 (6)* | |
H16C | 0.265 (2) | 0.3889 (19) | 0.6484 (18) | 0.036 (6)* | |
H16D | 0.184 (2) | 0.4074 (18) | 1.0135 (19) | 0.036 (6)* | |
H16E | 0.223 (2) | 0.3664 (18) | 0.8903 (19) | 0.033 (6)* | |
H16F | 0.309 (2) | 0.442 (2) | 0.9308 (18) | 0.033 (6)* | |
H17A | 0.425 (2) | 0.1270 (19) | 0.508 (2) | 0.042 (7)* | |
H17B | 0.397 (2) | 0.093 (2) | 0.633 (2) | 0.039 (7)* | |
H17C | 0.316 (2) | 0.052 (2) | 0.5537 (19) | 0.037 (6)* | |
H17D | 0.224 (3) | 0.163 (2) | 0.954 (2) | 0.060 (8)* | |
H17E | 0.187 (3) | 0.203 (2) | 1.079 (2) | 0.056 (8)* | |
H17F | 0.308 (2) | 0.110 (2) | 1.0472 (19) | 0.040 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0344 (3) | 0.0212 (3) | 0.0415 (3) | −0.0073 (2) | −0.0008 (2) | −0.0024 (2) |
S2 | 0.0574 (4) | 0.0217 (3) | 0.0366 (3) | −0.0094 (3) | −0.0153 (3) | 0.0029 (2) |
N1 | 0.0336 (10) | 0.0234 (9) | 0.0275 (9) | −0.0048 (8) | −0.0037 (8) | 0.0008 (7) |
N2 | 0.0304 (9) | 0.0253 (9) | 0.0269 (9) | −0.0047 (7) | −0.0063 (8) | −0.0014 (7) |
C1 | 0.0280 (11) | 0.0306 (11) | 0.0267 (11) | −0.0098 (9) | −0.0076 (9) | −0.0009 (9) |
C2 | 0.0367 (13) | 0.0360 (13) | 0.0384 (13) | −0.0158 (11) | −0.0059 (10) | 0.0055 (10) |
C3 | 0.0339 (13) | 0.0538 (15) | 0.0284 (12) | −0.0171 (11) | −0.0057 (10) | 0.0058 (11) |
C4 | 0.0321 (12) | 0.0517 (15) | 0.0264 (12) | −0.0020 (11) | −0.0008 (10) | −0.0041 (11) |
C5 | 0.0416 (13) | 0.0331 (13) | 0.0320 (13) | 0.0000 (11) | −0.0038 (10) | −0.0021 (10) |
C6 | 0.0275 (10) | 0.0282 (11) | 0.0248 (11) | −0.0043 (9) | −0.0084 (9) | 0.0018 (8) |
C7 | 0.0253 (10) | 0.0234 (10) | 0.0247 (10) | −0.0061 (8) | −0.0096 (8) | 0.0007 (8) |
C8 | 0.0279 (10) | 0.0262 (10) | 0.0244 (10) | −0.0070 (8) | −0.0062 (8) | 0.0011 (8) |
C9 | 0.0254 (10) | 0.0217 (10) | 0.0257 (11) | −0.0045 (8) | −0.0005 (8) | −0.0006 (8) |
C10 | 0.0254 (10) | 0.0289 (11) | 0.0236 (11) | −0.0016 (9) | −0.0016 (8) | −0.0004 (8) |
C11 | 0.0379 (13) | 0.0385 (14) | 0.0334 (13) | −0.0075 (11) | −0.0103 (10) | −0.0019 (10) |
C12 | 0.0371 (13) | 0.0606 (17) | 0.0308 (13) | −0.0027 (12) | −0.0104 (11) | −0.0032 (12) |
C13 | 0.0416 (14) | 0.0590 (17) | 0.0273 (13) | 0.0082 (12) | −0.0081 (11) | 0.0056 (12) |
C14 | 0.0524 (15) | 0.0316 (13) | 0.0340 (13) | 0.0044 (12) | −0.0054 (11) | 0.0066 (10) |
C15 | 0.0357 (12) | 0.0299 (11) | 0.0230 (11) | −0.0012 (9) | −0.0025 (9) | 0.0009 (9) |
C16 | 0.0353 (13) | 0.0420 (14) | 0.0313 (13) | −0.0176 (11) | −0.0064 (11) | −0.0010 (11) |
C17 | 0.0293 (12) | 0.0379 (13) | 0.0324 (13) | 0.0011 (10) | −0.0064 (10) | −0.0001 (10) |
S1' | 0.0426 (3) | 0.0233 (3) | 0.0359 (3) | −0.0007 (2) | −0.0079 (3) | −0.0062 (2) |
S2' | 0.0405 (3) | 0.0226 (3) | 0.0323 (3) | −0.0048 (2) | −0.0129 (2) | −0.0014 (2) |
N1' | 0.0282 (9) | 0.0284 (9) | 0.0259 (9) | −0.0047 (7) | −0.0033 (7) | −0.0048 (7) |
N2' | 0.0377 (10) | 0.0258 (9) | 0.0294 (10) | −0.0036 (8) | −0.0050 (8) | −0.0016 (7) |
C1' | 0.0316 (11) | 0.0379 (12) | 0.0272 (11) | 0.0067 (10) | −0.0119 (9) | −0.0083 (9) |
C2' | 0.0430 (14) | 0.0448 (15) | 0.0385 (14) | 0.0138 (12) | −0.0151 (12) | −0.0137 (12) |
C3' | 0.0353 (14) | 0.078 (2) | 0.0301 (14) | 0.0172 (14) | −0.0085 (11) | −0.0159 (13) |
C4' | 0.0315 (13) | 0.075 (2) | 0.0299 (14) | −0.0016 (13) | −0.0028 (11) | −0.0033 (13) |
C5' | 0.0322 (12) | 0.0533 (16) | 0.0306 (12) | −0.0082 (11) | −0.0039 (10) | −0.0007 (11) |
C6' | 0.0263 (11) | 0.0368 (12) | 0.0241 (11) | −0.0021 (9) | −0.0074 (9) | −0.0047 (9) |
C7' | 0.0276 (10) | 0.0211 (10) | 0.0263 (11) | −0.0025 (8) | −0.0095 (8) | −0.0026 (8) |
C8' | 0.0280 (11) | 0.0259 (11) | 0.0260 (11) | −0.0054 (9) | −0.0026 (9) | −0.0032 (8) |
C9' | 0.0277 (10) | 0.0218 (10) | 0.0264 (11) | −0.0065 (8) | −0.0012 (8) | −0.0005 (8) |
C10' | 0.0300 (11) | 0.0296 (11) | 0.0265 (11) | −0.0052 (9) | −0.0021 (9) | 0.0010 (9) |
C11' | 0.0457 (14) | 0.0354 (14) | 0.0360 (13) | −0.0018 (11) | −0.0107 (11) | 0.0077 (11) |
C12' | 0.0401 (14) | 0.0534 (16) | 0.0347 (13) | −0.0059 (12) | −0.0127 (11) | 0.0108 (12) |
C13' | 0.0375 (13) | 0.0541 (16) | 0.0294 (13) | −0.0155 (12) | −0.0093 (10) | −0.0007 (11) |
C14' | 0.0376 (13) | 0.0373 (13) | 0.0361 (13) | −0.0103 (11) | −0.0095 (10) | −0.0021 (10) |
C15' | 0.0280 (11) | 0.0289 (11) | 0.0255 (11) | −0.0050 (9) | −0.0029 (9) | 0.0014 (9) |
C16' | 0.0328 (12) | 0.0328 (12) | 0.0327 (13) | 0.0005 (10) | −0.0074 (10) | −0.0054 (10) |
C17' | 0.0354 (13) | 0.0388 (14) | 0.0380 (14) | −0.0152 (11) | −0.0029 (11) | −0.0037 (11) |
S1—C1 | 1.726 (2) | S1'—C1' | 1.731 (2) |
S1—C7 | 1.7455 (19) | S1'—C7' | 1.749 (2) |
S2—C15 | 1.729 (2) | S2'—C15' | 1.732 (2) |
S2—C9 | 1.752 (2) | S2'—C9' | 1.749 (2) |
N1—C7 | 1.288 (2) | N1'—C7' | 1.293 (3) |
N1—C6 | 1.398 (3) | N1'—C6' | 1.393 (3) |
N2—C9 | 1.283 (2) | N2'—C9' | 1.289 (3) |
N2—C10 | 1.398 (3) | N2'—C10' | 1.394 (3) |
C1—C2 | 1.397 (3) | C1'—C6' | 1.394 (3) |
C1—C6 | 1.401 (3) | C1'—C2' | 1.403 (3) |
C2—C3 | 1.373 (3) | C2'—C3' | 1.369 (4) |
C2—H2 | 0.92 (2) | C2'—H2' | 0.96 (2) |
C3—C4 | 1.388 (3) | C3'—C4' | 1.394 (4) |
C3—H3 | 0.96 (2) | C3'—H3' | 0.91 (3) |
C4—C5 | 1.375 (3) | C4'—C5' | 1.381 (3) |
C4—H4 | 0.89 (2) | C4'—H4' | 0.93 (3) |
C5—C6 | 1.396 (3) | C5'—C6' | 1.397 (3) |
C5—H5 | 0.98 (2) | C5'—H5' | 1.04 (2) |
C7—C8 | 1.527 (3) | C7'—C8' | 1.524 (3) |
C8—C9 | 1.522 (3) | C8'—C9' | 1.524 (3) |
C8—C16 | 1.531 (3) | C8'—C16' | 1.534 (3) |
C8—C17 | 1.532 (3) | C8'—C17' | 1.534 (3) |
C10—C11 | 1.390 (3) | C10'—C11' | 1.393 (3) |
C10—C15 | 1.399 (3) | C10'—C15' | 1.403 (3) |
C11—C12 | 1.378 (3) | C11'—C12' | 1.379 (3) |
C11—H11 | 0.92 (2) | C11'—H11' | 0.88 (3) |
C12—C13 | 1.384 (4) | C12'—C13' | 1.388 (4) |
C12—H12 | 0.94 (3) | C12'—H12' | 0.95 (2) |
C13—C14 | 1.374 (4) | C13'—C14' | 1.375 (3) |
C13—H13 | 0.99 (2) | C13'—H13' | 0.97 (2) |
C14—C15 | 1.400 (3) | C14'—C15' | 1.394 (3) |
C14—H14 | 0.90 (2) | C14'—H14' | 0.95 (2) |
C16—H16A | 0.95 (2) | C16'—H16D | 0.97 (2) |
C16—H16B | 0.96 (2) | C16'—H16E | 0.95 (2) |
C16—H16C | 1.02 (2) | C16'—H16F | 0.95 (2) |
C17—H17A | 0.96 (3) | C17'—H17D | 0.97 (3) |
C17—H17B | 0.92 (2) | C17'—H17E | 0.95 (3) |
C17—H17C | 0.96 (2) | C17'—H17F | 0.98 (2) |
C1—S1—C7 | 89.31 (10) | C1'—S1'—C7' | 88.76 (10) |
C15—S2—C9 | 89.11 (10) | C15'—S2'—C9' | 88.97 (10) |
C7—N1—C6 | 111.00 (17) | C7'—N1'—C6' | 110.43 (17) |
C9—N2—C10 | 110.91 (17) | C9'—N2'—C10' | 110.13 (18) |
C2—C1—C6 | 120.6 (2) | C6'—C1'—C2' | 121.1 (2) |
C2—C1—S1 | 129.91 (18) | C6'—C1'—S1' | 109.69 (16) |
C6—C1—S1 | 109.51 (15) | C2'—C1'—S1' | 129.2 (2) |
C3—C2—C1 | 118.5 (2) | C3'—C2'—C1' | 118.0 (3) |
C3—C2—H2 | 122.4 (16) | C3'—C2'—H2' | 122.1 (14) |
C1—C2—H2 | 119.2 (16) | C1'—C2'—H2' | 119.8 (14) |
C2—C3—C4 | 121.0 (2) | C2'—C3'—C4' | 121.2 (2) |
C2—C3—H3 | 119.6 (14) | C2'—C3'—H3' | 118.8 (17) |
C4—C3—H3 | 119.4 (14) | C4'—C3'—H3' | 119.9 (17) |
C5—C4—C3 | 121.4 (2) | C5'—C4'—C3' | 121.3 (3) |
C5—C4—H4 | 117.6 (15) | C5'—C4'—H4' | 118.2 (18) |
C3—C4—H4 | 121.0 (15) | C3'—C4'—H4' | 120.3 (18) |
C4—C5—C6 | 118.5 (2) | C4'—C5'—C6' | 118.2 (2) |
C4—C5—H5 | 122.3 (15) | C4'—C5'—H5' | 122.8 (13) |
C6—C5—H5 | 119.1 (15) | C6'—C5'—H5' | 119.0 (13) |
C5—C6—N1 | 125.49 (19) | N1'—C6'—C1' | 115.01 (19) |
C5—C6—C1 | 120.1 (2) | N1'—C6'—C5' | 124.8 (2) |
N1—C6—C1 | 114.43 (18) | C1'—C6'—C5' | 120.2 (2) |
N1—C7—C8 | 122.99 (17) | N1'—C7'—C8' | 123.16 (18) |
N1—C7—S1 | 115.73 (15) | N1'—C7'—S1' | 116.10 (15) |
C8—C7—S1 | 121.24 (14) | C8'—C7'—S1' | 120.74 (14) |
C9—C8—C7 | 106.21 (15) | C7'—C8'—C9' | 106.10 (16) |
C9—C8—C16 | 111.35 (18) | C7'—C8'—C16' | 108.99 (17) |
C7—C8—C16 | 108.85 (17) | C9'—C8'—C16' | 111.91 (17) |
C9—C8—C17 | 108.69 (17) | C7'—C8'—C17' | 110.90 (18) |
C7—C8—C17 | 111.44 (17) | C9'—C8'—C17' | 109.02 (18) |
C16—C8—C17 | 110.24 (19) | C16'—C8'—C17' | 109.87 (19) |
N2—C9—C8 | 123.26 (18) | N2'—C9'—C8' | 122.76 (18) |
N2—C9—S2 | 115.81 (15) | N2'—C9'—S2' | 116.46 (16) |
C8—C9—S2 | 120.88 (14) | C8'—C9'—S2' | 120.71 (14) |
C11—C10—N2 | 125.01 (19) | C11'—C10'—N2' | 125.0 (2) |
C11—C10—C15 | 120.2 (2) | C11'—C10'—C15' | 119.6 (2) |
N2—C10—C15 | 114.78 (18) | N2'—C10'—C15' | 115.36 (18) |
C12—C11—C10 | 118.5 (2) | C12'—C11'—C10' | 119.0 (2) |
C12—C11—H11 | 121.8 (16) | C12'—C11'—H11' | 120.9 (18) |
C10—C11—H11 | 119.7 (16) | C10'—C11'—H11' | 120.1 (18) |
C11—C12—C13 | 121.2 (2) | C11'—C12'—C13' | 120.9 (2) |
C11—C12—H12 | 119.6 (17) | C11'—C12'—H12' | 117.4 (15) |
C13—C12—H12 | 119.2 (16) | C13'—C12'—H12' | 121.6 (15) |
C14—C13—C12 | 121.5 (2) | C14'—C13'—C12' | 121.4 (2) |
C14—C13—H13 | 122.9 (14) | C14'—C13'—H13' | 121.0 (13) |
C12—C13—H13 | 115.3 (14) | C12'—C13'—H13' | 117.7 (13) |
C13—C14—C15 | 117.8 (2) | C13'—C14'—C15' | 118.0 (2) |
C13—C14—H14 | 124.2 (14) | C13'—C14'—H14' | 122.6 (13) |
C15—C14—H14 | 117.9 (15) | C15'—C14'—H14' | 119.4 (13) |
C10—C15—C14 | 120.9 (2) | C14'—C15'—C10' | 121.2 (2) |
C10—C15—S2 | 109.38 (15) | C14'—C15'—S2' | 129.73 (17) |
C14—C15—S2 | 129.72 (19) | C10'—C15'—S2' | 109.08 (15) |
C8—C16—H16A | 107.9 (14) | C8'—C16'—H16D | 110.2 (13) |
C8—C16—H16B | 109.1 (13) | C8'—C16'—H16E | 109.4 (13) |
H16A—C16—H16B | 112.0 (19) | H16D—C16'—H16E | 109.8 (18) |
C8—C16—H16C | 109.6 (12) | C8'—C16'—H16F | 111.6 (13) |
H16A—C16—H16C | 106.8 (18) | H16D—C16'—H16F | 109.2 (18) |
H16B—C16—H16C | 111.4 (18) | H16E—C16'—H16F | 106.7 (18) |
C8—C17—H17A | 109.2 (14) | C8'—C17'—H17D | 108.2 (16) |
C8—C17—H17B | 106.9 (15) | C8'—C17'—H17E | 107.9 (16) |
H17A—C17—H17B | 111 (2) | H17D—C17'—H17E | 112 (2) |
C8—C17—H17C | 112.3 (14) | C8'—C17'—H17F | 111.2 (13) |
H17A—C17—H17C | 106.9 (19) | H17D—C17'—H17F | 113 (2) |
H17B—C17—H17C | 111 (2) | H17E—C17'—H17F | 105 (2) |
C7—S1—C1—C2 | 178.3 (2) | C7'—S1'—C1'—C6' | 0.84 (15) |
C7—S1—C1—C6 | −0.96 (15) | C7'—S1'—C1'—C2' | −178.3 (2) |
C6—C1—C2—C3 | 0.3 (3) | C6'—C1'—C2'—C3' | 0.9 (3) |
S1—C1—C2—C3 | −178.91 (17) | S1'—C1'—C2'—C3' | 179.97 (18) |
C1—C2—C3—C4 | −0.8 (4) | C1'—C2'—C3'—C4' | −0.4 (4) |
C2—C3—C4—C5 | 0.4 (4) | C2'—C3'—C4'—C5' | 0.0 (4) |
C3—C4—C5—C6 | 0.5 (4) | C3'—C4'—C5'—C6' | 0.0 (4) |
C4—C5—C6—N1 | 178.3 (2) | C7'—N1'—C6'—C1' | 0.3 (2) |
C4—C5—C6—C1 | −0.9 (3) | C7'—N1'—C6'—C5' | 179.6 (2) |
C7—N1—C6—C5 | −179.0 (2) | C2'—C1'—C6'—N1' | 178.42 (19) |
C7—N1—C6—C1 | 0.2 (2) | S1'—C1'—C6'—N1' | −0.8 (2) |
C2—C1—C6—C5 | 0.6 (3) | C2'—C1'—C6'—C5' | −0.9 (3) |
S1—C1—C6—C5 | 179.95 (17) | S1'—C1'—C6'—C5' | 179.83 (16) |
C2—C1—C6—N1 | −178.73 (19) | C4'—C5'—C6'—N1' | −178.8 (2) |
S1—C1—C6—N1 | 0.7 (2) | C4'—C5'—C6'—C1' | 0.4 (3) |
C6—N1—C7—C8 | 176.71 (17) | C6'—N1'—C7'—C8' | 179.98 (17) |
C6—N1—C7—S1 | −1.0 (2) | C6'—N1'—C7'—S1' | 0.4 (2) |
C1—S1—C7—N1 | 1.18 (16) | C1'—S1'—C7'—N1' | −0.74 (17) |
C1—S1—C7—C8 | −176.57 (16) | C1'—S1'—C7'—C8' | 179.65 (16) |
N1—C7—C8—C9 | −77.6 (2) | N1'—C7'—C8'—C9' | −76.5 (2) |
S1—C7—C8—C9 | 99.98 (17) | S1'—C7'—C8'—C9' | 103.05 (17) |
N1—C7—C8—C16 | 42.4 (3) | N1'—C7'—C8'—C16' | 44.1 (3) |
S1—C7—C8—C16 | −140.02 (16) | S1'—C7'—C8'—C16' | −136.29 (16) |
N1—C7—C8—C17 | 164.18 (19) | N1'—C7'—C8'—C17' | 165.2 (2) |
S1—C7—C8—C17 | −18.2 (2) | S1'—C7'—C8'—C17' | −15.2 (2) |
C10—N2—C9—C8 | 176.62 (17) | C10'—N2'—C9'—C8' | 176.41 (17) |
C10—N2—C9—S2 | −0.8 (2) | C10'—N2'—C9'—S2' | −0.5 (2) |
C7—C8—C9—N2 | −77.1 (2) | C7'—C8'—C9'—N2' | −74.6 (2) |
C16—C8—C9—N2 | 164.55 (19) | C16'—C8'—C9'—N2' | 166.66 (19) |
C17—C8—C9—N2 | 42.9 (3) | C17'—C8'—C9'—N2' | 44.9 (3) |
C7—C8—C9—S2 | 100.20 (17) | C7'—C8'—C9'—S2' | 102.22 (17) |
C16—C8—C9—S2 | −18.2 (2) | C16'—C8'—C9'—S2' | −16.5 (2) |
C17—C8—C9—S2 | −139.79 (16) | C17'—C8'—C9'—S2' | −138.29 (17) |
C15—S2—C9—N2 | 0.49 (17) | C15'—S2'—C9'—N2' | 0.39 (17) |
C15—S2—C9—C8 | −176.98 (16) | C15'—S2'—C9'—C8' | −176.60 (16) |
C9—N2—C10—C11 | −177.3 (2) | C9'—N2'—C10'—C11' | −177.9 (2) |
C9—N2—C10—C15 | 0.8 (2) | C9'—N2'—C10'—C15' | 0.4 (3) |
N2—C10—C11—C12 | 177.7 (2) | N2'—C10'—C11'—C12' | 178.4 (2) |
C15—C10—C11—C12 | −0.3 (3) | C15'—C10'—C11'—C12' | 0.2 (3) |
C10—C11—C12—C13 | 0.6 (4) | C10'—C11'—C12'—C13' | 0.1 (4) |
C11—C12—C13—C14 | −0.4 (4) | C11'—C12'—C13'—C14' | −0.4 (4) |
C12—C13—C14—C15 | −0.1 (4) | C12'—C13'—C14'—C15' | 0.3 (4) |
C11—C10—C15—C14 | −0.2 (3) | C13'—C14'—C15'—C10' | 0.0 (3) |
N2—C10—C15—C14 | −178.41 (19) | C13'—C14'—C15'—S2' | −178.20 (17) |
C11—C10—C15—S2 | 177.81 (17) | C11'—C10'—C15'—C14' | −0.3 (3) |
N2—C10—C15—S2 | −0.4 (2) | N2'—C10'—C15'—C14' | −178.64 (19) |
C13—C14—C15—C10 | 0.4 (3) | C11'—C10'—C15'—S2' | 178.25 (17) |
C13—C14—C15—S2 | −177.15 (18) | N2'—C10'—C15'—S2' | −0.1 (2) |
C9—S2—C15—C10 | −0.03 (16) | C9'—S2'—C15'—C14' | 178.2 (2) |
C9—S2—C15—C14 | 177.8 (2) | C9'—S2'—C15'—C10' | −0.14 (16) |
Experimental details
Crystal data | |
Chemical formula | C17H14N2S2 |
Mr | 310.42 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 173 |
a, b, c (Å) | 10.3791 (13), 11.8832 (15), 12.3391 (15) |
α, β, γ (°) | 86.730 (2), 78.048 (2), 80.779 (2) |
V (Å3) | 1469.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.36 |
Crystal size (mm) | 0.42 × 0.24 × 0.05 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1995) |
Tmin, Tmax | 0.865, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17048, 6379, 5007 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.119, 1.04 |
No. of reflections | 6379 |
No. of parameters | 491 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.43, −0.21 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).
Investigations in our lab are focused on the synthesis and study of nitrile hydration catalysts and their activity with respect to cyanohydrin substrates (Ahmed et al., 2009). Catalysts investigated by our group have been found to be susceptible to poisoning by cyanide produced from cyanohydrin decomposition. Nitrile hydratase enzymes are capable of hydrating cyanohydrins (Nagasawa & Yamada, 1989; Kobayashi et al., 1992). Additionally, some nitrile hydratase mimics have successfully hydrated acetonitrile in the presence of free cyanide (Tyler et al., 2003). With the goal of investigating these mimics for their activity towards cyanohydrins, attempts were made to synthesize nitrile hydratase mimics similar to those made earlier by Tyler et al. (2003), but based on dimethylmalonyl dichloride, rather than 2,6-pyridinedicarbonyl dichloride.
The present X-ray study of the product showed that deprotection of 2,2-dimethyl-N,N'-bis(2-(tritylthio)phenyl)malonamide with trifluoroacetic acid and triethylsilane resulted in a ring closing condensation which yielded 2,2-bis(benzothiazole)propane, rather than the desired N,N'-bis(2-mercaptophenyl)-2,2-dimethylmalonamide.
There are two symmetry independent, but geometrically very similar molecules in the crystal of the title compound (Fig. 1). Dihedral angles between the least squares planes of the benzothiazole groups are equal to 83.93 (3) and 81.26 (3)° in molecules N1—C17 and N1'-C17', respectively.