Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010100659X/sk1475sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010100659X/sk1475Isup2.hkl |
CCDC reference: 169952
N,N'-dicyclohexylthiourea was obtained from Lancaster. The synthesis of the tellurium complex followed a modification of the literature method of Foss & Hauge (1959, 1961). TeO2 (1.603 g, 10 mmol) was dissolved in hot concentrated HCl (20 ml). This solution was added rapidly with stirring to N,N'-dicyclohexylthiourea (9.62 g, 40 mmol) dissolved in hot 95% ethanol (110 ml). Upon cooling the resulting red-brown solution to room temperature, small yellow crystals of (I) and some red lumps formed. The latter were discarded and the rest was filtered and washed with cold ethanol to which a few drops of concentrated HCl were added [yield 6.1 g, 66.7%; m.p. 415–417 K (decomposition)]. Analysis, found: Cl 7.75, S 10.45%; calculated for C39H72Cl2N6S3Te: Cl 7.73, S 10.49%.
All H atoms were treated as riding, with N—H = 0.88, C—H (CH) = 1.00 and C—H (CH2) = 0.99 Å. The isotropic displacement parameters of the H atoms were fixed at 1.2Ueq of their parent atoms. The maximum residual peak was located 0.82 Å from Te.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C39H72ClN6S3Te+·Cl− | Dx = 1.290 Mg m−3 |
Mr = 919.71 | Melting point = 415–417 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 20.1931 (5) Å | Cell parameters from 8192 reflections |
b = 20.2156 (4) Å | θ = 1.7–32.9° |
c = 23.1990 (4) Å | µ = 0.91 mm−1 |
V = 9470.2 (3) Å3 | T = 173 K |
Z = 8 | Octahedron, yellow |
F(000) = 3856 | 0.37 × 0.25 × 0.22 mm |
Bruker SMART 2K CCD diffractometer | 17005 independent reflections |
Radiation source: normal-focus sealed tube | 10136 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans | θmax = 32.9°, θmin = 1.7° |
Absorption correction: numerical (SHELXTL; Sheldrick, 2001) | h = −30→30 |
Tmin = 0.809, Tmax = 0.831 | k = −30→29 |
124117 measured reflections | l = −34→33 |
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) = 0.066 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0322P)2] where P = (Fo2 + 2Fc2)/3 |
17005 reflections | (Δ/σ)max = 0.005 |
460 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C39H72ClN6S3Te+·Cl− | V = 9470.2 (3) Å3 |
Mr = 919.71 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 20.1931 (5) Å | µ = 0.91 mm−1 |
b = 20.2156 (4) Å | T = 173 K |
c = 23.1990 (4) Å | 0.37 × 0.25 × 0.22 mm |
Bruker SMART 2K CCD diffractometer | 17005 independent reflections |
Absorption correction: numerical (SHELXTL; Sheldrick, 2001) | 10136 reflections with I > 2σ(I) |
Tmin = 0.809, Tmax = 0.831 | Rint = 0.055 |
124117 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.066 | H-atom parameters constrained |
S = 0.92 | Δρmax = 0.47 e Å−3 |
17005 reflections | Δρmin = −0.29 e Å−3 |
460 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. Dihedral angles from final SHELXL refinement run: Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 10.9408 (0.0018) x - 5.7535 (0.0020) y + 18.3469 (0.0015) z = 7.6008 (0.0015) * 0.2023 (0.0002) S1 * -0.1688 (0.0002) S2 * 0.1771 (0.0002) S3 * -0.1652 (0.0002) Cl1 * -0.0454 (0.0002) Te Rms deviation of fitted atoms = 0.1613 3.3802 (0.0146) x + 15.2531 (0.0060) y + 14.7214 (0.0102) z = 13.0364 (0.0083) Angle to previous plane (with approximate e.s.d.) = 67.80 (0.03) * 0.0033 (0.0003) S1 * -0.0122 (0.0013) C1 * 0.0045 (0.0005) N1 * 0.0044 (0.0005) N2 Rms deviation of fitted atoms = 0.0070 10.9408 (0.0018) x - 5.7535 (0.0020) y + 18.3469 (0.0015) z = 7.6008 (0.0015) Angle to previous plane (with approximate e.s.d.) = 67.80 (0.03) * 0.2023 (0.0002) S1 * -0.1688 (0.0002) S2 * 0.1771 (0.0002) S3 * -0.1652 (0.0002) Cl1 * -0.0454 (0.0002) Te Rms deviation of fitted atoms = 0.1613 9.5563 (0.0129) x + 16.6390 (0.0056) y + 7.2840 (0.0130) z = 12.2906 (0.0043) Angle to previous plane (with approximate e.s.d.) = 74.31 (0.03) * -0.0010 (0.0003) S2 * 0.0037 (0.0012) C14 * -0.0013 (0.0004) N3 * -0.0014 (0.0005) N4 Rms deviation of fitted atoms = 0.0021 10.9408 (0.0018) x - 5.7535 (0.0020) y + 18.3469 (0.0015) z = 7.6008 (0.0015) Angle to previous plane (with approximate e.s.d.) = 74.31 (0.03) * 0.2023 (0.0002) S1 * -0.1688 (0.0002) S2 * 0.1771 (0.0002) S3 * -0.1652 (0.0002) Cl1 * -0.0454 (0.0002) Te Rms deviation of fitted atoms = 0.1613 14.1347 (0.0104) x - 12.3804 (0.0140) y - 8.5232 (0.0107) z = 5.4869 (0.0114) Angle to previous plane (with approximate e.s.d.) = 74.75 (0.03) * 0.0006 (0.0004) S3 * -0.0021 (0.0013) C27 * 0.0007 (0.0005) N5 * 0.0007 (0.0005) N6 Rms deviation of fitted atoms = 0.0012 |
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 | ||
Te | 0.656148 (5) | 0.419956 (5) | 0.152223 (4) | 0.03465 (3) | |
S1 | 0.60668 (2) | 0.50599 (2) | 0.222202 (16) | 0.04977 (11) | |
S2 | 0.558814 (19) | 0.33958 (2) | 0.178341 (16) | 0.04086 (9) | |
S3 | 0.722615 (18) | 0.31793 (2) | 0.092726 (15) | 0.03654 (9) | |
Cl1 | 0.74515 (2) | 0.50907 (2) | 0.120565 (17) | 0.04852 (10) | |
Cl2 | 0.584896 (19) | 0.186503 (19) | 0.390211 (14) | 0.03861 (8) | |
N1 | 0.50470 (7) | 0.57313 (6) | 0.17613 (5) | 0.0422 (3) | |
H1A | 0.4903 | 0.6088 | 0.1584 | 0.051* | |
C1 | 0.56897 (9) | 0.56059 (8) | 0.17323 (6) | 0.0419 (4) | |
N2 | 0.60757 (7) | 0.59019 (6) | 0.13482 (6) | 0.0450 (3) | |
H2A | 0.6505 | 0.5897 | 0.1415 | 0.054* | |
C2 | 0.45503 (8) | 0.53249 (8) | 0.20658 (6) | 0.0411 (4) | |
H2B | 0.4782 | 0.5063 | 0.2371 | 0.049* | |
N3 | 0.65212 (6) | 0.26522 (6) | 0.22576 (5) | 0.0385 (3) | |
H3A | 0.6643 | 0.2601 | 0.1896 | 0.046* | |
C3 | 0.42358 (8) | 0.48461 (9) | 0.16450 (7) | 0.0471 (4) | |
H3B | 0.4582 | 0.4552 | 0.1485 | 0.056* | |
H3C | 0.4038 | 0.5097 | 0.1321 | 0.056* | |
N4 | 0.56410 (6) | 0.28963 (6) | 0.28545 (5) | 0.0384 (3) | |
H4A | 0.5796 | 0.2596 | 0.3094 | 0.046* | |
C4 | 0.37006 (10) | 0.44279 (10) | 0.19335 (8) | 0.0635 (5) | |
H4B | 0.3481 | 0.4148 | 0.1640 | 0.076* | |
H4C | 0.3908 | 0.4132 | 0.2222 | 0.076* | |
N5 | 0.69269 (6) | 0.35750 (6) | −0.01440 (5) | 0.0433 (3) | |
H5A | 0.6690 | 0.3529 | −0.0460 | 0.052* | |
C5 | 0.31860 (10) | 0.48602 (12) | 0.22278 (8) | 0.0698 (6) | |
H5B | 0.2940 | 0.5116 | 0.1934 | 0.084* | |
H5C | 0.2866 | 0.4577 | 0.2436 | 0.084* | |
N6 | 0.63414 (7) | 0.26871 (7) | 0.01749 (5) | 0.0473 (3) | |
H6A | 0.6170 | 0.2686 | −0.0174 | 0.057* | |
C6 | 0.35123 (11) | 0.53330 (10) | 0.26491 (9) | 0.0688 (6) | |
H6B | 0.3720 | 0.5077 | 0.2965 | 0.083* | |
H6C | 0.3171 | 0.5624 | 0.2821 | 0.083* | |
C7 | 0.40392 (11) | 0.57586 (9) | 0.23543 (9) | 0.0709 (7) | |
H7A | 0.3827 | 0.6047 | 0.2063 | 0.085* | |
H7B | 0.4258 | 0.6045 | 0.2644 | 0.085* | |
C8 | 0.58495 (8) | 0.62394 (8) | 0.08183 (6) | 0.0402 (4) | |
H8A | 0.5508 | 0.6576 | 0.0924 | 0.048* | |
C9 | 0.55427 (9) | 0.57453 (8) | 0.03950 (7) | 0.0464 (4) | |
H9A | 0.5867 | 0.5392 | 0.0308 | 0.056* | |
H9B | 0.5149 | 0.5537 | 0.0573 | 0.056* | |
C10 | 0.53408 (9) | 0.60916 (9) | −0.01627 (7) | 0.0512 (4) | |
H10A | 0.4986 | 0.6416 | −0.0079 | 0.061* | |
H10B | 0.5162 | 0.5761 | −0.0437 | 0.061* | |
C11 | 0.59288 (9) | 0.64478 (9) | −0.04386 (7) | 0.0531 (5) | |
H11A | 0.6264 | 0.6119 | −0.0560 | 0.064* | |
H11B | 0.5778 | 0.6688 | −0.0786 | 0.064* | |
C12 | 0.62396 (9) | 0.69325 (9) | −0.00183 (8) | 0.0536 (5) | |
H12A | 0.5920 | 0.7291 | 0.0066 | 0.064* | |
H12B | 0.6636 | 0.7134 | −0.0198 | 0.064* | |
C13 | 0.64395 (8) | 0.65927 (9) | 0.05464 (8) | 0.0497 (4) | |
H13A | 0.6796 | 0.6268 | 0.0469 | 0.060* | |
H13B | 0.6614 | 0.6927 | 0.0819 | 0.060* | |
C14 | 0.59426 (7) | 0.29470 (8) | 0.23501 (6) | 0.0349 (3) | |
C15 | 0.69785 (7) | 0.24027 (8) | 0.27046 (6) | 0.0370 (3) | |
H15A | 0.6733 | 0.2087 | 0.2959 | 0.044* | |
C16 | 0.75419 (8) | 0.20343 (9) | 0.24123 (8) | 0.0526 (4) | |
H16A | 0.7770 | 0.2334 | 0.2139 | 0.063* | |
H16B | 0.7362 | 0.1656 | 0.2191 | 0.063* | |
C17 | 0.80408 (10) | 0.17791 (11) | 0.28630 (9) | 0.0684 (6) | |
H17A | 0.7826 | 0.1436 | 0.3104 | 0.082* | |
H17B | 0.8421 | 0.1572 | 0.2663 | 0.082* | |
C18 | 0.82896 (9) | 0.23336 (11) | 0.32477 (9) | 0.0674 (6) | |
H18A | 0.8580 | 0.2146 | 0.3550 | 0.081* | |
H18B | 0.8557 | 0.2646 | 0.3015 | 0.081* | |
C19 | 0.77275 (9) | 0.27026 (10) | 0.35276 (7) | 0.0557 (5) | |
H19A | 0.7906 | 0.3076 | 0.3756 | 0.067* | |
H19B | 0.7488 | 0.2403 | 0.3794 | 0.067* | |
C20 | 0.72465 (8) | 0.29678 (8) | 0.30747 (7) | 0.0456 (4) | |
H20A | 0.6874 | 0.3196 | 0.3268 | 0.055* | |
H20B | 0.7477 | 0.3293 | 0.2826 | 0.055* | |
C21 | 0.50724 (7) | 0.32912 (8) | 0.30557 (6) | 0.0374 (3) | |
H21A | 0.4946 | 0.3606 | 0.2742 | 0.045* | |
C22 | 0.44834 (8) | 0.28519 (9) | 0.31802 (7) | 0.0464 (4) | |
H22A | 0.4610 | 0.2511 | 0.3466 | 0.056* | |
H22B | 0.4347 | 0.2623 | 0.2822 | 0.056* | |
C23 | 0.39024 (9) | 0.32563 (10) | 0.34138 (8) | 0.0568 (5) | |
H23A | 0.3743 | 0.3561 | 0.3110 | 0.068* | |
H23B | 0.3534 | 0.2954 | 0.3514 | 0.068* | |
C24 | 0.40961 (10) | 0.36528 (10) | 0.39410 (8) | 0.0635 (5) | |
H24A | 0.4202 | 0.3348 | 0.4262 | 0.076* | |
H24B | 0.3719 | 0.3933 | 0.4062 | 0.076* | |
C25 | 0.46926 (10) | 0.40882 (10) | 0.38163 (9) | 0.0668 (6) | |
H25A | 0.4830 | 0.4314 | 0.4176 | 0.080* | |
H25B | 0.4566 | 0.4432 | 0.3533 | 0.080* | |
C26 | 0.52773 (9) | 0.36913 (9) | 0.35791 (8) | 0.0528 (4) | |
H26A | 0.5640 | 0.3997 | 0.3472 | 0.063* | |
H26B | 0.5446 | 0.3390 | 0.3882 | 0.063* | |
C27 | 0.68024 (7) | 0.31447 (8) | 0.02781 (6) | 0.0362 (3) | |
C28 | 0.74112 (7) | 0.41152 (7) | −0.01438 (6) | 0.0367 (3) | |
H28A | 0.7480 | 0.4264 | 0.0263 | 0.044* | |
C29 | 0.71280 (8) | 0.46861 (9) | −0.04848 (8) | 0.0546 (5) | |
H29A | 0.6711 | 0.4836 | −0.0302 | 0.066* | |
H29B | 0.7023 | 0.4536 | −0.0880 | 0.066* | |
C30 | 0.76150 (9) | 0.52635 (9) | −0.05136 (9) | 0.0630 (5) | |
H30A | 0.7424 | 0.5619 | −0.0755 | 0.076* | |
H30B | 0.7683 | 0.5443 | −0.0121 | 0.076* | |
C31 | 0.82687 (10) | 0.50572 (11) | −0.07596 (9) | 0.0675 (6) | |
H31A | 0.8580 | 0.5435 | −0.0751 | 0.081* | |
H31B | 0.8211 | 0.4919 | −0.1166 | 0.081* | |
C32 | 0.85528 (9) | 0.44852 (11) | −0.04109 (11) | 0.0756 (7) | |
H32A | 0.8647 | 0.4638 | −0.0014 | 0.091* | |
H32B | 0.8976 | 0.4341 | −0.0586 | 0.091* | |
C33 | 0.80722 (9) | 0.38965 (9) | −0.03875 (9) | 0.0585 (5) | |
H33A | 0.8008 | 0.3716 | −0.0780 | 0.070* | |
H33B | 0.8261 | 0.3543 | −0.0143 | 0.070* | |
C34 | 0.60891 (8) | 0.21889 (8) | 0.05719 (7) | 0.0404 (4) | |
H34A | 0.6212 | 0.2324 | 0.0972 | 0.048* | |
C35 | 0.53411 (8) | 0.21638 (8) | 0.05333 (9) | 0.0534 (5) | |
H35A | 0.5209 | 0.2053 | 0.0134 | 0.064* | |
H35B | 0.5156 | 0.2604 | 0.0628 | 0.064* | |
C36 | 0.50584 (10) | 0.16501 (9) | 0.09468 (10) | 0.0675 (6) | |
H36A | 0.5152 | 0.1787 | 0.1348 | 0.081* | |
H36B | 0.4572 | 0.1628 | 0.0898 | 0.081* | |
C37 | 0.53518 (9) | 0.09730 (9) | 0.08417 (11) | 0.0700 (6) | |
H37A | 0.5217 | 0.0813 | 0.0456 | 0.084* | |
H37B | 0.5180 | 0.0659 | 0.1133 | 0.084* | |
C38 | 0.61008 (10) | 0.09982 (10) | 0.08767 (11) | 0.0725 (6) | |
H38A | 0.6284 | 0.0556 | 0.0785 | 0.087* | |
H38B | 0.6235 | 0.1113 | 0.1275 | 0.087* | |
C39 | 0.63862 (9) | 0.15079 (9) | 0.04575 (9) | 0.0591 (5) | |
H39A | 0.6873 | 0.1528 | 0.0503 | 0.071* | |
H39B | 0.6288 | 0.1372 | 0.0057 | 0.071* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Te | 0.03150 (5) | 0.04802 (6) | 0.02443 (4) | −0.00137 (4) | −0.00503 (4) | 0.00449 (4) |
S1 | 0.0625 (3) | 0.0582 (3) | 0.02862 (18) | 0.0089 (2) | 0.00225 (18) | −0.00049 (18) |
S2 | 0.03182 (19) | 0.0584 (3) | 0.03241 (18) | −0.00061 (18) | −0.00359 (15) | 0.01299 (17) |
S3 | 0.02987 (19) | 0.0475 (2) | 0.03225 (17) | 0.00064 (17) | −0.00586 (14) | 0.00238 (16) |
Cl1 | 0.0380 (2) | 0.0654 (3) | 0.0421 (2) | −0.0145 (2) | −0.00347 (16) | −0.00345 (19) |
Cl2 | 0.03915 (19) | 0.0488 (2) | 0.02788 (15) | 0.00325 (17) | −0.00153 (14) | 0.00699 (15) |
N1 | 0.0515 (8) | 0.0399 (8) | 0.0351 (6) | 0.0019 (6) | 0.0102 (6) | 0.0044 (6) |
C1 | 0.0535 (11) | 0.0408 (9) | 0.0313 (7) | 0.0009 (8) | 0.0067 (7) | −0.0057 (6) |
N2 | 0.0464 (8) | 0.0474 (8) | 0.0412 (7) | 0.0000 (6) | 0.0067 (6) | 0.0025 (6) |
C2 | 0.0515 (10) | 0.0415 (9) | 0.0305 (7) | −0.0014 (7) | 0.0065 (7) | 0.0064 (6) |
N3 | 0.0360 (7) | 0.0507 (8) | 0.0288 (6) | 0.0055 (6) | 0.0010 (5) | 0.0041 (5) |
C3 | 0.0457 (10) | 0.0584 (11) | 0.0371 (8) | −0.0016 (8) | 0.0066 (7) | −0.0030 (7) |
N4 | 0.0328 (7) | 0.0472 (8) | 0.0352 (6) | 0.0067 (6) | 0.0033 (5) | 0.0137 (6) |
C4 | 0.0646 (12) | 0.0775 (14) | 0.0483 (10) | −0.0218 (11) | 0.0059 (9) | −0.0041 (10) |
N5 | 0.0471 (8) | 0.0523 (9) | 0.0305 (6) | −0.0137 (7) | −0.0109 (6) | 0.0037 (6) |
C5 | 0.0503 (11) | 0.1038 (18) | 0.0552 (11) | −0.0003 (12) | 0.0127 (9) | 0.0257 (12) |
N6 | 0.0528 (8) | 0.0538 (9) | 0.0355 (7) | −0.0170 (7) | −0.0109 (6) | 0.0034 (6) |
C6 | 0.0828 (15) | 0.0656 (13) | 0.0580 (12) | 0.0075 (11) | 0.0406 (11) | 0.0079 (10) |
C7 | 0.0963 (17) | 0.0523 (12) | 0.0643 (12) | −0.0012 (11) | 0.0509 (12) | −0.0038 (9) |
C8 | 0.0467 (9) | 0.0334 (8) | 0.0405 (8) | 0.0028 (7) | 0.0133 (7) | 0.0006 (6) |
C9 | 0.0665 (11) | 0.0343 (9) | 0.0384 (8) | −0.0046 (8) | 0.0132 (8) | −0.0014 (7) |
C10 | 0.0711 (12) | 0.0454 (10) | 0.0371 (8) | −0.0002 (9) | 0.0101 (8) | −0.0006 (7) |
C11 | 0.0668 (12) | 0.0488 (11) | 0.0437 (9) | 0.0103 (9) | 0.0196 (8) | 0.0096 (8) |
C12 | 0.0539 (11) | 0.0420 (10) | 0.0650 (11) | 0.0014 (9) | 0.0224 (9) | 0.0152 (9) |
C13 | 0.0470 (10) | 0.0455 (10) | 0.0566 (10) | −0.0024 (8) | 0.0146 (8) | 0.0061 (8) |
C14 | 0.0328 (8) | 0.0398 (9) | 0.0321 (7) | −0.0031 (7) | −0.0019 (6) | 0.0048 (6) |
C15 | 0.0341 (8) | 0.0406 (9) | 0.0365 (7) | 0.0021 (7) | 0.0004 (6) | 0.0106 (6) |
C16 | 0.0476 (10) | 0.0601 (12) | 0.0502 (10) | 0.0153 (9) | 0.0065 (8) | 0.0072 (9) |
C17 | 0.0557 (12) | 0.0766 (15) | 0.0727 (13) | 0.0312 (11) | 0.0079 (10) | 0.0204 (11) |
C18 | 0.0418 (11) | 0.0916 (17) | 0.0689 (13) | 0.0041 (10) | −0.0095 (9) | 0.0272 (12) |
C19 | 0.0464 (10) | 0.0683 (13) | 0.0523 (10) | −0.0061 (9) | −0.0139 (8) | 0.0099 (9) |
C20 | 0.0403 (9) | 0.0483 (10) | 0.0482 (9) | −0.0010 (8) | −0.0067 (7) | 0.0075 (8) |
C21 | 0.0339 (8) | 0.0429 (9) | 0.0352 (7) | 0.0056 (7) | 0.0032 (6) | 0.0114 (6) |
C22 | 0.0344 (9) | 0.0550 (11) | 0.0497 (9) | −0.0044 (8) | 0.0004 (7) | −0.0040 (8) |
C23 | 0.0363 (9) | 0.0774 (14) | 0.0566 (11) | 0.0026 (9) | 0.0085 (8) | 0.0059 (10) |
C24 | 0.0610 (12) | 0.0832 (15) | 0.0462 (10) | 0.0198 (11) | 0.0152 (9) | 0.0048 (10) |
C25 | 0.0728 (14) | 0.0576 (13) | 0.0700 (13) | 0.0121 (11) | −0.0039 (11) | −0.0189 (10) |
C26 | 0.0451 (10) | 0.0457 (10) | 0.0676 (12) | −0.0036 (8) | −0.0048 (8) | −0.0094 (9) |
C27 | 0.0329 (8) | 0.0432 (9) | 0.0326 (7) | −0.0005 (7) | −0.0019 (6) | −0.0031 (6) |
C28 | 0.0357 (8) | 0.0426 (9) | 0.0317 (7) | −0.0048 (7) | −0.0014 (6) | −0.0019 (6) |
C29 | 0.0396 (10) | 0.0565 (12) | 0.0677 (12) | −0.0004 (8) | 0.0008 (8) | 0.0182 (9) |
C30 | 0.0570 (12) | 0.0521 (12) | 0.0800 (14) | −0.0012 (9) | 0.0037 (10) | 0.0189 (10) |
C31 | 0.0641 (13) | 0.0747 (15) | 0.0636 (12) | −0.0232 (11) | 0.0189 (10) | 0.0002 (11) |
C32 | 0.0384 (11) | 0.0733 (15) | 0.1151 (19) | −0.0036 (10) | 0.0181 (11) | −0.0105 (14) |
C33 | 0.0435 (10) | 0.0539 (12) | 0.0779 (13) | 0.0032 (9) | 0.0089 (9) | −0.0100 (10) |
C34 | 0.0395 (9) | 0.0400 (9) | 0.0416 (8) | −0.0051 (7) | −0.0043 (7) | 0.0020 (7) |
C35 | 0.0411 (10) | 0.0371 (10) | 0.0820 (13) | 0.0053 (8) | −0.0013 (9) | 0.0073 (9) |
C36 | 0.0424 (11) | 0.0504 (12) | 0.1096 (17) | −0.0014 (9) | 0.0146 (11) | 0.0081 (11) |
C37 | 0.0517 (12) | 0.0391 (11) | 0.1193 (19) | −0.0017 (9) | 0.0037 (12) | 0.0146 (11) |
C38 | 0.0526 (12) | 0.0464 (11) | 0.1185 (19) | 0.0123 (9) | −0.0041 (12) | 0.0187 (12) |
C39 | 0.0374 (10) | 0.0574 (12) | 0.0825 (14) | 0.0085 (8) | 0.0032 (9) | −0.0002 (10) |
Te—S1 | 2.5803 (4) | C16—H16B | 0.9900 |
Te—S2 | 2.6211 (4) | C17—C18 | 1.518 (3) |
Te—S3 | 2.8214 (4) | C17—H17A | 0.9900 |
Te—Cl1 | 2.6485 (4) | C17—H17B | 0.9900 |
S1—C1 | 1.7576 (17) | C18—C19 | 1.505 (3) |
N1—C1 | 1.324 (2) | C18—H18A | 0.9900 |
N1—H1A | 0.8800 | C18—H18B | 0.9900 |
N1—C2 | 1.4766 (19) | C19—C20 | 1.528 (2) |
N2—C1 | 1.326 (2) | C19—H19A | 0.9900 |
N2—C8 | 1.478 (2) | C19—H19B | 0.9900 |
N2—H2A | 0.8800 | C20—H20A | 0.9900 |
S2—C14 | 1.7504 (14) | C20—H20B | 0.9900 |
N3—C14 | 1.3290 (18) | C21—C22 | 1.512 (2) |
N3—H3A | 0.8800 | C21—C26 | 1.517 (2) |
N3—C15 | 1.4774 (17) | C21—H21A | 1.0000 |
S3—C27 | 1.7336 (14) | C22—C23 | 1.529 (2) |
N4—C14 | 1.3232 (17) | C22—H22A | 0.9900 |
N4—C21 | 1.4743 (19) | C22—H22B | 0.9900 |
N4—H4A | 0.8800 | C23—C24 | 1.514 (3) |
N5—C27 | 1.3337 (18) | C23—H23A | 0.9900 |
N5—C28 | 1.4660 (19) | C23—H23B | 0.9900 |
N5—H5A | 0.8800 | C24—C25 | 1.520 (3) |
N6—C27 | 1.3341 (19) | C24—H24A | 0.9900 |
N6—C34 | 1.4568 (19) | C24—H24B | 0.9900 |
N6—H6A | 0.8800 | C25—C26 | 1.530 (3) |
C2—C7 | 1.511 (2) | C25—H25A | 0.9900 |
C2—C3 | 1.514 (2) | C25—H25B | 0.9900 |
C2—H2B | 1.0000 | C26—H26A | 0.9900 |
C3—C4 | 1.527 (2) | C26—H26B | 0.9900 |
C3—H3B | 0.9900 | C28—C29 | 1.511 (2) |
C3—H3C | 0.9900 | C28—C33 | 1.516 (2) |
C4—C5 | 1.520 (3) | C28—H28A | 1.0000 |
C4—H4B | 0.9900 | C29—C30 | 1.528 (2) |
C4—H4C | 0.9900 | C29—H29A | 0.9900 |
C5—C6 | 1.518 (3) | C29—H29B | 0.9900 |
C5—H5B | 0.9900 | C30—C31 | 1.497 (3) |
C5—H5C | 0.9900 | C30—H30A | 0.9900 |
C6—C7 | 1.530 (2) | C30—H30B | 0.9900 |
C6—H6B | 0.9900 | C31—C32 | 1.523 (3) |
C6—H6C | 0.9900 | C31—H31A | 0.9900 |
C7—H7A | 0.9900 | C31—H31B | 0.9900 |
C7—H7B | 0.9900 | C32—C33 | 1.537 (3) |
C8—C13 | 1.526 (2) | C32—H32A | 0.9900 |
C8—C9 | 1.532 (2) | C32—H32B | 0.9900 |
C8—H8A | 1.0000 | C33—H33A | 0.9900 |
C9—C10 | 1.527 (2) | C33—H33B | 0.9900 |
C9—H9A | 0.9900 | C34—C35 | 1.514 (2) |
C9—H9B | 0.9900 | C34—C39 | 1.525 (2) |
C10—C11 | 1.529 (2) | C34—H34A | 1.0000 |
C10—H10A | 0.9900 | C35—C36 | 1.525 (2) |
C10—H10B | 0.9900 | C35—H35A | 0.9900 |
C11—C12 | 1.518 (3) | C35—H35B | 0.9900 |
C11—H11A | 0.9900 | C36—C37 | 1.511 (3) |
C11—H11B | 0.9900 | C36—H36A | 0.9900 |
C12—C13 | 1.533 (2) | C36—H36B | 0.9900 |
C12—H12A | 0.9900 | C37—C38 | 1.515 (3) |
C12—H12B | 0.9900 | C37—H37A | 0.9900 |
C13—H13A | 0.9900 | C37—H37B | 0.9900 |
C13—H13B | 0.9900 | C38—C39 | 1.530 (3) |
C15—C16 | 1.519 (2) | C38—H38A | 0.9900 |
C15—C20 | 1.528 (2) | C38—H38B | 0.9900 |
C15—H15A | 1.0000 | C39—H39A | 0.9900 |
C16—C17 | 1.541 (2) | C39—H39B | 0.9900 |
C16—H16A | 0.9900 | ||
S1—Te—S2 | 88.971 (15) | C19—C18—H18B | 109.3 |
S1—Te—S3 | 169.951 (12) | C17—C18—H18B | 109.3 |
S1—Te—Cl1 | 88.782 (15) | H18A—C18—H18B | 107.9 |
S2—Te—S3 | 90.956 (13) | C18—C19—C20 | 110.88 (15) |
S2—Te—Cl1 | 174.031 (13) | C18—C19—H19A | 109.5 |
S3—Te—Cl1 | 92.220 (13) | C20—C19—H19A | 109.5 |
Te—S1—C1 | 100.63 (5) | C18—C19—H19B | 109.5 |
Te—S2—C14 | 100.85 (5) | C20—C19—H19B | 109.5 |
Te—S3—C27 | 102.70 (5) | H19A—C19—H19B | 108.1 |
S1—C1—N1 | 120.81 (12) | C15—C20—C19 | 110.44 (14) |
S1—C1—N2 | 117.57 (13) | C15—C20—H20A | 109.6 |
N1—C1—N2 | 121.58 (15) | C19—C20—H20A | 109.6 |
C1—N1—C2 | 125.70 (14) | C15—C20—H20B | 109.6 |
C1—N1—H1A | 117.1 | C19—C20—H20B | 109.6 |
C2—N1—H1A | 117.1 | H20A—C20—H20B | 108.1 |
C1—N2—C8 | 125.82 (15) | N4—C21—C22 | 110.80 (13) |
C1—N2—H2A | 117.1 | N4—C21—C26 | 109.25 (13) |
C8—N2—H2A | 117.1 | C22—C21—C26 | 112.02 (13) |
N1—C2—C7 | 110.67 (13) | N4—C21—H21A | 108.2 |
N1—C2—C3 | 109.39 (12) | C22—C21—H21A | 108.2 |
C7—C2—C3 | 111.73 (16) | C26—C21—H21A | 108.2 |
N1—C2—H2B | 108.3 | C21—C22—C23 | 110.93 (14) |
C7—C2—H2B | 108.3 | C21—C22—H22A | 109.5 |
C3—C2—H2B | 108.3 | C23—C22—H22A | 109.5 |
C14—N3—C15 | 126.10 (12) | C21—C22—H22B | 109.5 |
C14—N3—H3A | 117.0 | C23—C22—H22B | 109.5 |
C15—N3—H3A | 117.0 | H22A—C22—H22B | 108.0 |
C2—C3—C4 | 111.60 (13) | C24—C23—C22 | 111.79 (15) |
C2—C3—H3B | 109.3 | C24—C23—H23A | 109.3 |
C4—C3—H3B | 109.3 | C22—C23—H23A | 109.3 |
C2—C3—H3C | 109.3 | C24—C23—H23B | 109.3 |
C4—C3—H3C | 109.3 | C22—C23—H23B | 109.3 |
H3B—C3—H3C | 108.0 | H23A—C23—H23B | 107.9 |
C14—N4—C21 | 126.62 (12) | C23—C24—C25 | 110.95 (15) |
C14—N4—H4A | 116.7 | C23—C24—H24A | 109.5 |
C21—N4—H4A | 116.7 | C25—C24—H24A | 109.5 |
C5—C4—C3 | 111.25 (17) | C23—C24—H24B | 109.5 |
C5—C4—H4B | 109.4 | C25—C24—H24B | 109.5 |
C3—C4—H4B | 109.4 | H24A—C24—H24B | 108.0 |
C5—C4—H4C | 109.4 | C24—C25—C26 | 112.12 (16) |
C3—C4—H4C | 109.4 | C24—C25—H25A | 109.2 |
H4B—C4—H4C | 108.0 | C26—C25—H25A | 109.2 |
C27—N5—C28 | 127.69 (12) | C24—C25—H25B | 109.2 |
C27—N5—H5A | 116.2 | C26—C25—H25B | 109.2 |
C28—N5—H5A | 116.2 | H25A—C25—H25B | 107.9 |
C6—C5—C4 | 110.77 (17) | C21—C26—C25 | 110.92 (15) |
C6—C5—H5B | 109.5 | C21—C26—H26A | 109.5 |
C4—C5—H5B | 109.5 | C25—C26—H26A | 109.5 |
C6—C5—H5C | 109.5 | C21—C26—H26B | 109.5 |
C4—C5—H5C | 109.5 | C25—C26—H26B | 109.5 |
H5B—C5—H5C | 108.1 | H26A—C26—H26B | 108.0 |
C27—N6—C34 | 127.59 (13) | S3—C27—N5 | 121.23 (12) |
C27—N6—H6A | 116.2 | S3—C27—N6 | 121.90 (12) |
C34—N6—H6A | 116.2 | N5—C27—N6 | 116.87 (13) |
C5—C6—C7 | 111.61 (16) | N5—C28—C29 | 108.43 (12) |
C5—C6—H6B | 109.3 | N5—C28—C33 | 111.72 (13) |
C7—C6—H6B | 109.3 | C29—C28—C33 | 111.14 (14) |
C5—C6—H6C | 109.3 | N5—C28—H28A | 108.5 |
C7—C6—H6C | 109.3 | C29—C28—H28A | 108.5 |
H6B—C6—H6C | 108.0 | C33—C28—H28A | 108.5 |
C2—C7—C6 | 110.28 (15) | C28—C29—C30 | 111.27 (14) |
C2—C7—H7A | 109.6 | C28—C29—H29A | 109.4 |
C6—C7—H7A | 109.6 | C30—C29—H29A | 109.4 |
C2—C7—H7B | 109.6 | C28—C29—H29B | 109.4 |
C6—C7—H7B | 109.6 | C30—C29—H29B | 109.4 |
H7A—C7—H7B | 108.1 | H29A—C29—H29B | 108.0 |
N2—C8—C13 | 108.58 (13) | C31—C30—C29 | 111.80 (17) |
N2—C8—C9 | 110.93 (12) | C31—C30—H30A | 109.3 |
C13—C8—C9 | 110.86 (13) | C29—C30—H30A | 109.3 |
N2—C8—H8A | 108.8 | C31—C30—H30B | 109.3 |
C13—C8—H8A | 108.8 | C29—C30—H30B | 109.3 |
C9—C8—H8A | 108.8 | H30A—C30—H30B | 107.9 |
C10—C9—C8 | 110.63 (13) | C30—C31—C32 | 109.94 (16) |
C10—C9—H9A | 109.5 | C30—C31—H31A | 109.7 |
C8—C9—H9A | 109.5 | C32—C31—H31A | 109.7 |
C10—C9—H9B | 109.5 | C30—C31—H31B | 109.7 |
C8—C9—H9B | 109.5 | C32—C31—H31B | 109.7 |
H9A—C9—H9B | 108.1 | H31A—C31—H31B | 108.2 |
C9—C10—C11 | 111.30 (15) | C31—C32—C33 | 111.64 (17) |
C9—C10—H10A | 109.4 | C31—C32—H32A | 109.3 |
C11—C10—H10A | 109.4 | C33—C32—H32A | 109.3 |
C9—C10—H10B | 109.4 | C31—C32—H32B | 109.3 |
C11—C10—H10B | 109.4 | C33—C32—H32B | 109.3 |
H10A—C10—H10B | 108.0 | H32A—C32—H32B | 108.0 |
C12—C11—C10 | 110.86 (13) | C28—C33—C32 | 110.08 (15) |
C12—C11—H11A | 109.5 | C28—C33—H33A | 109.6 |
C10—C11—H11A | 109.5 | C32—C33—H33A | 109.6 |
C12—C11—H11B | 109.5 | C28—C33—H33B | 109.6 |
C10—C11—H11B | 109.5 | C32—C33—H33B | 109.6 |
H11A—C11—H11B | 108.1 | H33A—C33—H33B | 108.2 |
C11—C12—C13 | 111.62 (14) | N6—C34—C35 | 109.56 (13) |
C11—C12—H12A | 109.3 | N6—C34—C39 | 112.11 (14) |
C13—C12—H12A | 109.3 | C35—C34—C39 | 110.62 (14) |
C11—C12—H12B | 109.3 | N6—C34—H34A | 108.1 |
C13—C12—H12B | 109.3 | C35—C34—H34A | 108.1 |
H12A—C12—H12B | 108.0 | C39—C34—H34A | 108.1 |
C8—C13—C12 | 110.94 (14) | C34—C35—C36 | 111.05 (14) |
C8—C13—H13A | 109.5 | C34—C35—H35A | 109.4 |
C12—C13—H13A | 109.5 | C36—C35—H35A | 109.4 |
C8—C13—H13B | 109.5 | C34—C35—H35B | 109.4 |
C12—C13—H13B | 109.5 | C36—C35—H35B | 109.4 |
H13A—C13—H13B | 108.0 | H35A—C35—H35B | 108.0 |
N3—C14—N4 | 120.85 (13) | C37—C36—C35 | 111.63 (17) |
S2—C14—N3 | 118.07 (11) | C37—C36—H36A | 109.3 |
S2—C14—N4 | 121.08 (11) | C35—C36—H36A | 109.3 |
N3—C15—C16 | 108.79 (12) | C37—C36—H36B | 109.3 |
N3—C15—C20 | 111.13 (12) | C35—C36—H36B | 109.3 |
C16—C15—C20 | 110.61 (13) | H36A—C36—H36B | 108.0 |
N3—C15—H15A | 108.8 | C36—C37—C38 | 110.62 (16) |
C16—C15—H15A | 108.8 | C36—C37—H37A | 109.5 |
C20—C15—H15A | 108.8 | C38—C37—H37A | 109.5 |
C15—C16—C17 | 110.54 (14) | C36—C37—H37B | 109.5 |
C15—C16—H16A | 109.5 | C38—C37—H37B | 109.5 |
C17—C16—H16A | 109.5 | H37A—C37—H37B | 108.1 |
C15—C16—H16B | 109.5 | C37—C38—C39 | 111.39 (16) |
C17—C16—H16B | 109.5 | C37—C38—H38A | 109.3 |
H16A—C16—H16B | 108.1 | C39—C38—H38A | 109.3 |
C18—C17—C16 | 111.59 (16) | C37—C38—H38B | 109.3 |
C18—C17—H17A | 109.3 | C39—C38—H38B | 109.3 |
C16—C17—H17A | 109.3 | H38A—C38—H38B | 108.0 |
C18—C17—H17B | 109.3 | C34—C39—C38 | 110.44 (15) |
C16—C17—H17B | 109.3 | C34—C39—H39A | 109.6 |
H17A—C17—H17B | 108.0 | C38—C39—H39A | 109.6 |
C19—C18—C17 | 111.71 (16) | C34—C39—H39B | 109.6 |
C19—C18—H18A | 109.3 | C38—C39—H39B | 109.6 |
C17—C18—H18A | 109.3 | H39A—C39—H39B | 108.1 |
S2—Te—S1—C1 | −102.77 (6) | C20—C15—C16—C17 | 56.32 (19) |
Cl1—Te—S1—C1 | 71.70 (6) | C15—C16—C17—C18 | −54.5 (2) |
S3—Te—S1—C1 | 167.56 (9) | C16—C17—C18—C19 | 54.4 (2) |
S1—Te—S2—C14 | −92.25 (5) | C17—C18—C19—C20 | −55.8 (2) |
Cl1—Te—S2—C14 | −160.16 (13) | N3—C15—C20—C19 | −179.01 (13) |
S3—Te—S2—C14 | 77.70 (5) | C16—C15—C20—C19 | −58.06 (18) |
S1—Te—S3—C27 | 167.79 (9) | C18—C19—C20—C15 | 57.5 (2) |
S2—Te—S3—C27 | 78.29 (6) | C14—N4—C21—C22 | 119.06 (16) |
Cl1—Te—S3—C27 | −96.66 (6) | C14—N4—C21—C26 | −117.05 (17) |
C2—N1—C1—N2 | 164.29 (14) | N4—C21—C22—C23 | 177.54 (13) |
C2—N1—C1—S1 | −18.0 (2) | C26—C21—C22—C23 | 55.26 (18) |
Te—S1—C1—N1 | 121.89 (12) | C21—C22—C23—C24 | −55.4 (2) |
Te—S1—C1—N2 | −60.32 (13) | C22—C23—C24—C25 | 54.9 (2) |
N1—C1—N2—C8 | −18.4 (2) | C23—C24—C25—C26 | −54.4 (2) |
S1—C1—N2—C8 | 163.83 (12) | N4—C21—C26—C25 | −177.76 (14) |
C1—N1—C2—C7 | 141.83 (17) | C22—C21—C26—C25 | −54.6 (2) |
C1—N1—C2—C3 | −94.65 (18) | C24—C25—C26—C21 | 54.1 (2) |
N1—C2—C3—C4 | −178.12 (14) | C28—N5—C27—N6 | −179.12 (14) |
C7—C2—C3—C4 | −55.2 (2) | C28—N5—C27—S3 | 0.5 (2) |
C2—C3—C4—C5 | 54.4 (2) | C34—N6—C27—N5 | −176.22 (15) |
C3—C4—C5—C6 | −54.8 (2) | C34—N6—C27—S3 | 4.2 (2) |
C4—C5—C6—C7 | 56.2 (2) | Te—S3—C27—N5 | 80.20 (13) |
N1—C2—C7—C6 | 177.85 (16) | Te—S3—C27—N6 | −100.19 (14) |
C3—C2—C7—C6 | 55.7 (2) | C27—N5—C28—C29 | −145.37 (16) |
C5—C6—C7—C2 | −56.5 (2) | C27—N5—C28—C33 | 91.81 (19) |
C1—N2—C8—C13 | 172.13 (15) | N5—C28—C29—C30 | −178.76 (15) |
C1—N2—C8—C9 | −65.8 (2) | C33—C28—C29—C30 | −55.6 (2) |
N2—C8—C9—C10 | −177.28 (13) | C28—C29—C30—C31 | 56.2 (2) |
C13—C8—C9—C10 | −56.55 (19) | C29—C30—C31—C32 | −56.1 (2) |
C8—C9—C10—C11 | 56.54 (19) | C30—C31—C32—C33 | 56.7 (2) |
C9—C10—C11—C12 | −55.90 (19) | N5—C28—C33—C32 | 176.88 (16) |
C10—C11—C12—C13 | 55.2 (2) | C29—C28—C33—C32 | 55.6 (2) |
N2—C8—C13—C12 | 177.99 (13) | C31—C32—C33—C28 | −56.5 (2) |
C9—C8—C13—C12 | 55.89 (19) | C27—N6—C34—C35 | 134.77 (17) |
C11—C12—C13—C8 | −55.56 (19) | C27—N6—C34—C39 | −102.0 (2) |
C21—N4—C14—N3 | 167.52 (14) | N6—C34—C35—C36 | −179.60 (15) |
C21—N4—C14—S2 | −13.2 (2) | C39—C34—C35—C36 | 56.3 (2) |
C15—N3—C14—N4 | −17.5 (2) | C34—C35—C36—C37 | −56.1 (2) |
C15—N3—C14—S2 | 163.20 (12) | C35—C36—C37—C38 | 55.5 (3) |
Te—S2—C14—N4 | 126.50 (12) | C36—C37—C38—C39 | −55.9 (3) |
Te—S2—C14—N3 | −54.17 (12) | N6—C34—C39—C38 | −179.12 (15) |
C14—N3—C15—C16 | 173.70 (15) | C35—C34—C39—C38 | −56.5 (2) |
C14—N3—C15—C20 | −64.28 (19) | C37—C38—C39—C34 | 56.6 (2) |
N3—C15—C16—C17 | 178.65 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl1 | 0.88 | 2.56 | 3.2431 (15) | 135 |
N3—H3A···S3 | 0.88 | 2.79 | 3.5618 (12) | 147 |
N1—H1A···Cl2i | 0.88 | 2.46 | 3.3007 (14) | 160 |
N4—H4A···Cl2 | 0.88 | 2.39 | 3.2294 (12) | 160 |
N5—H5A···Cl2ii | 0.88 | 2.39 | 3.2290 (13) | 160 |
N6—H6A···Cl2ii | 0.88 | 2.42 | 3.2445 (13) | 157 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C39H72ClN6S3Te+·Cl− |
Mr | 919.71 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 173 |
a, b, c (Å) | 20.1931 (5), 20.2156 (4), 23.1990 (4) |
V (Å3) | 9470.2 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.91 |
Crystal size (mm) | 0.37 × 0.25 × 0.22 |
Data collection | |
Diffractometer | Bruker SMART 2K CCD diffractometer |
Absorption correction | Numerical (SHELXTL; Sheldrick, 2001) |
Tmin, Tmax | 0.809, 0.831 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 124117, 17005, 10136 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.764 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.066, 0.92 |
No. of reflections | 17005 |
No. of parameters | 460 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.29 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1998), SAINT, SHELXS86 (Sheldrick, 1990), SHELXTL (Sheldrick, 2001), SHELXTL.
Te—S1 | 2.5803 (4) | N3—C14 | 1.3290 (18) |
Te—S2 | 2.6211 (4) | N3—C15 | 1.4774 (17) |
Te—S3 | 2.8214 (4) | S3—C27 | 1.7336 (14) |
Te—Cl1 | 2.6485 (4) | N4—C14 | 1.3232 (17) |
S1—C1 | 1.7576 (17) | N4—C21 | 1.4743 (19) |
N1—C1 | 1.324 (2) | N5—C27 | 1.3337 (18) |
N1—C2 | 1.4766 (19) | N5—C28 | 1.4660 (19) |
N2—C1 | 1.326 (2) | N6—C27 | 1.3341 (19) |
N2—C8 | 1.478 (2) | N6—C34 | 1.4568 (19) |
S2—C14 | 1.7504 (14) | ||
S1—Te—S2 | 88.971 (15) | S1—C1—N1 | 120.81 (12) |
S1—Te—S3 | 169.951 (12) | S1—C1—N2 | 117.57 (13) |
S1—Te—Cl1 | 88.782 (15) | N1—C1—N2 | 121.58 (15) |
S2—Te—S3 | 90.956 (13) | N3—C14—N4 | 120.85 (13) |
S2—Te—Cl1 | 174.031 (13) | S2—C14—N3 | 118.07 (11) |
S3—Te—Cl1 | 92.220 (13) | S2—C14—N4 | 121.08 (11) |
Te—S1—C1 | 100.63 (5) | S3—C27—N5 | 121.23 (12) |
Te—S2—C14 | 100.85 (5) | S3—C27—N6 | 121.90 (12) |
Te—S3—C27 | 102.70 (5) | N5—C27—N6 | 116.87 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cl1 | 0.88 | 2.56 | 3.2431 (15) | 135 |
N3—H3A···S3 | 0.88 | 2.79 | 3.5618 (12) | 147 |
N1—H1A···Cl2i | 0.88 | 2.46 | 3.3007 (14) | 160 |
N4—H4A···Cl2 | 0.88 | 2.39 | 3.2294 (12) | 160 |
N5—H5A···Cl2ii | 0.88 | 2.39 | 3.2290 (13) | 160 |
N6—H6A···Cl2ii | 0.88 | 2.42 | 3.2445 (13) | 157 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z−1/2. |
The expected reaction between thioureas and TeO2 dissolved in HCl are Te4+ + 4stu + 4Cl- = [TeCl2(stu)2] + (stu)2Cl2 (Foss & Hauge, 1959; Husebye, 1983). In the present case, a third stu ligand has displaced one of the two chloride ligands to give the [TeCl(stu)3]Cl product, (I), where stu = (C6H11NH)2CS. \sch
The structure of the cation in (I) is square planar, with a TeClS3 coordination sphere. This is the first time such coordination has been observed for tellurium. The two thioureas trans to each other point up from the coordination plane, whereas the third points down. This is a conformation with a minimized steric interaction between the ligands (Fig. 1).
The SCN2 units of the thiourea ligands are approximately planar and the SCN2 units trans to each other (S1 and S3) form angles with the coordination plane of 67.80 (3) and 74.75 (3)°, respectively. The remaining thiourea assumes a corresponding angle of 74.31 (3)°. Angles around 70° seem to be common for trans-[TeCl2(stu)2] complexes (Husebye et al., 2001).
The interplanar SCN2/SCN2 angle is 54.69 (6)° for the two trans-related thioureas. This is a rather large angle compared with the values in the trans complexes mentioned above, which are around 13° (Husebye et al., 2001). An analogous bromide, [TeBr(stu)3]Br, has been synthesized and its structure reported by Kumar et al. (1990). Here, stu is 1-methylimidazole-2(3H)-thione, an N,N'-dimethyl-substituted ethylenethiourea ligand. In this complex, two adjacent thioureas point to the same side of the coordination plane, whereas the third points to the opposite side. This is a geometry that brings the thiourea ligands into closer contact compared with the geometry of the present chloride analogue, but then the bulk of the thiourea ligand is smaller in the bromide.
The Te—S bond lengths in (I) vary considerably. Bonding in square planar TeII complexes is of the three-centre four-electron (3c-4 e) type, with a bond order of 0.5. In the near linear S1—Te—S3 sequence, Te—S1 is 2.5803 (4) and Te—S3 2.8214 (4) Å. Asymmetry in two such weak and chemically equivalent bonds is not uncommon in TeII compounds. The average bond length of 2.7009 Å is slightly longer than 2.68 Å, the average found for such 3c-4 e systems (Husebye, 1983). However, great asymmetry in the two Te—S bond lengths is often seen to give an increase in average bond lengths in linear S—Te—S systems (Husebye, 1983). It is interesting to note that the corresponding average Te—S bond length in the bromide complex with a nearly symmetric S—Te—S sequence is 2.701 Å (Kumar et al., 1990), the same value as that found in the chloride. The Te—S2 bond length in (I) is 2.6211 (4) Å and it is positioned trans to Te—Cl1, which has a bond length of 2.6485 (4) Å, indicating a weak trans influence of the N,N'-dicyclohexylthiourea ligand. However, this influence is still greater than that of the Cl-, indicated by the shortening of the Te—S bond at the expense of the Te—Cl bond, which lengthens relative to the average found in Cl—Te—Cl 3c-4 e systems (Husebye et al., 2001).
In the ligands, the C═S bond lengths are C1═S1 1.7576 (17), C14═S2 1.7504 (14) and C27═S3 1.7336 (14) Å. These values may be compared with the corresponding length of 1.681 (20) Å found in free thioureas (Allen et al., 1987) and reflect a normal lengthening upon coordination, a long Te—S bond corresponding to a short C═S bond and vice versa. The C—N bond length within the SCN2 group of the three thioureas has an average of 1.328 Å. This indicates partial double-bond character through transfer of charge from N to S.
The Cl- anion is connected to the S2 thiourea by an N4—H4···Cl2 hydrogen bond. The Cl- ligand forms an intramolecular N2—H2···Cl1 bond with the S1 thiourea; this is reflected in a small S1—C1—N2 angle of only 117.57 (13)°. There is also a possible weak intramolecular N3—H3···S3 hydrogen bond. Intermolecular N—H···Cl hydrogen bonds connect the ions into a three-dimensional network, shown in Fig. 2. Data for the hydrogen bonds are given in Table 2.