Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008891/qa0323sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008891/qa0323IIsup2.hkl |
CCDC reference: 150372
Complex (II) was prepared by reaction of [Ru(p-cymene)Cl2]2, 1,2,4-triazepine (I) and triethyamine (molar ratio 1:4:8) in 2-propanol at 353 K. The resulting solid was filtered off and recrystallized from CHCl3.
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL (Otwinowski & Minor, 1997); data reduction: HKL; program(s) used to solve structure: DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1992); software used to prepare material for publication: SHELXL97.
[RuCl(C10H14)(C10H11N3OS)] | F(000) = 2048 |
Mr = 503.01 | Dx = 1.592 Mg m−3 |
Monoclinic, Cc | Cu Kα radiation, λ = 1.54184 Å |
a = 20.647 (2) Å | Cell parameters from 8671 reflections |
b = 11.835 (1) Å | θ = 4.3–68.2° |
c = 17.275 (2) Å | µ = 8.28 mm−1 |
β = 96.253 (5)° | T = 293 K |
V = 4196.2 (7) Å3 | Prismatic, colourless |
Z = 8 | 0.7 × 0.2 × 0.2 mm |
Nonius KappaCCD diffractometer | 5007 independent reflections |
Radiation source: fine-focus sealed tube | 4791 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 9.43 pixels mm-1 | θmax = 68.2°, θmin = 4.3° |
ω scans | h = −24→23 |
Absorption correction: empirical (using intensity measurements) (using ΔF; Parkin et al., 1995) | k = 0→14 |
Tmin = 0.050, Tmax = 0.189 | l = −20→20 |
8671 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | Calculated w = 1/[σ2(Fo2) + (0.0718P)2 + 9.2057P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5007 reflections | Δρmax = 0.95 e Å−3 |
584 parameters | Δρmin = −0.80 e Å−3 |
2 restraints | Absolute structure: Flack (1983), Friedel pairs merged |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.467 (14) |
[RuCl(C10H14)(C10H11N3OS)] | V = 4196.2 (7) Å3 |
Mr = 503.01 | Z = 8 |
Monoclinic, Cc | Cu Kα radiation |
a = 20.647 (2) Å | µ = 8.28 mm−1 |
b = 11.835 (1) Å | T = 293 K |
c = 17.275 (2) Å | 0.7 × 0.2 × 0.2 mm |
β = 96.253 (5)° |
Nonius KappaCCD diffractometer | 5007 independent reflections |
Absorption correction: empirical (using intensity measurements) (using ΔF; Parkin et al., 1995) | 4791 reflections with I > 2σ(I) |
Tmin = 0.050, Tmax = 0.189 | Rint = 0.052 |
8671 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | Δρmax = 0.95 e Å−3 |
S = 1.03 | Δρmin = −0.80 e Å−3 |
5007 reflections | Absolute structure: Flack (1983), Friedel pairs merged |
584 parameters | Absolute structure parameter: 0.467 (14) |
2 restraints |
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 | ||
Ru1 | 0.50133 (3) | 0.33202 (5) | 0.49972 (4) | 0.0267 (2) | |
Cl1 | 0.41055 (12) | 0.2478 (3) | 0.42157 (16) | 0.0529 (7) | |
S1 | 0.45099 (11) | 0.25636 (19) | 0.61058 (15) | 0.0352 (6) | |
O1 | 0.4188 (4) | 0.5740 (6) | 0.4445 (4) | 0.0504 (19) | |
N1 | 0.4322 (4) | 0.4410 (7) | 0.5401 (5) | 0.0298 (18) | |
N2 | 0.3796 (4) | 0.4311 (7) | 0.6584 (5) | 0.042 (2) | |
N3 | 0.3766 (4) | 0.5476 (7) | 0.6740 (5) | 0.0357 (19) | |
C1 | 0.4149 (5) | 0.3884 (8) | 0.6036 (6) | 0.028 (2) | |
C2 | 0.3602 (4) | 0.6116 (7) | 0.6172 (6) | 0.030 (2) | |
C3 | 0.3393 (5) | 0.5683 (9) | 0.5373 (6) | 0.039 (2) | |
H31 | 0.3156 | 0.6238 | 0.5040 | 0.073 (7)* | |
H32 | 0.3113 | 0.5032 | 0.5415 | 0.073 (7)* | |
C4 | 0.3998 (4) | 0.5286 (8) | 0.5021 (6) | 0.034 (2) | |
C5 | 0.3667 (4) | 0.7351 (9) | 0.6349 (6) | 0.033 (2) | |
C6 | 0.3658 (5) | 0.8144 (9) | 0.5742 (7) | 0.039 (3) | |
H6 | 0.3605 | 0.7910 | 0.5226 | 0.02 (2)* | |
C7 | 0.3732 (5) | 0.9289 (10) | 0.5927 (7) | 0.045 (3) | |
H7 | 0.3729 | 0.9817 | 0.5528 | 0.04 (3)* | |
C8 | 0.3806 (5) | 0.9640 (9) | 0.6671 (8) | 0.049 (3) | |
H8 | 0.3846 | 1.0408 | 0.6780 | 0.04 (3)* | |
C9 | 0.3824 (6) | 0.8884 (10) | 0.7269 (8) | 0.047 (3) | |
H9 | 0.388 (5) | 0.904 (8) | 0.783 (7) | 0.04 (3)* | |
C10 | 0.3746 (5) | 0.7731 (10) | 0.7108 (7) | 0.042 (3) | |
H10 | 0.375 (7) | 0.737 (13) | 0.743 (8) | 0.073 (7)* | |
C11 | 0.3645 (6) | 0.3589 (11) | 0.7235 (8) | 0.055 (3) | |
H111 | 0.3250 | 0.3594 | 0.7262 | 0.073 (7)* | |
H112 | 0.3865 | 0.3874 | 0.7713 | 0.073 (7)* | |
H113 | 0.3784 | 0.2828 | 0.7155 | 0.073 (7)* | |
C12 | 0.6004 (5) | 0.3370 (7) | 0.5571 (6) | 0.028 (2) | |
C13 | 0.5937 (4) | 0.2431 (8) | 0.5065 (6) | 0.030 (2) | |
H13 | 0.610 (7) | 0.186 (11) | 0.534 (8) | 0.073 (7)* | |
C14 | 0.5701 (5) | 0.2546 (9) | 0.4290 (7) | 0.037 (2) | |
H14 | 0.5617 | 0.2221 | 0.3799 | 0.05 (3)* | |
C15 | 0.5529 (5) | 0.3660 (10) | 0.3963 (7) | 0.040 (2) | |
C16 | 0.5609 (5) | 0.4553 (10) | 0.4461 (6) | 0.041 (3) | |
H16 | 0.5542 | 0.5185 | 0.4141 | 0.07 (4)* | |
C17 | 0.5813 (5) | 0.4423 (10) | 0.5276 (7) | 0.040 (3) | |
H17 | 0.5893 | 0.5154 | 0.5460 | 0.073 (7)* | |
C18 | 0.6256 (5) | 0.3143 (10) | 0.6420 (6) | 0.040 (3) | |
H18 | 0.5973 | 0.2538 | 0.6574 | 0.04 (3)* | |
C19 | 0.6998 (5) | 0.3028 (12) | 0.6462 (7) | 0.058 (3) | |
H191 | 0.7147 | 0.3556 | 0.6230 | 0.073 (7)* | |
H192 | 0.7102 | 0.2327 | 0.6224 | 0.073 (7)* | |
H193 | 0.7183 | 0.3032 | 0.6997 | 0.073 (7)* | |
C20 | 0.6073 (6) | 0.4073 (10) | 0.6964 (7) | 0.058 (3) | |
H201 | 0.5740 | 0.4390 | 0.6771 | 0.073 (7)* | |
H202 | 0.6423 | 0.4610 | 0.7032 | 0.073 (7)* | |
H203 | 0.6000 | 0.3763 | 0.7461 | 0.073 (7)* | |
C21 | 0.5247 (7) | 0.3805 (12) | 0.3124 (7) | 0.059 (3) | |
H211 | 0.4909 | 0.4173 | 0.3107 | 0.10 (6)* | |
H212 | 0.5154 | 0.3075 | 0.2897 | 0.11 (6)* | |
H213 | 0.5552 | 0.4193 | 0.2837 | 0.13 (7)* | |
Ru2 | −0.39153 (3) | 0.09821 (5) | 0.04224 (3) | 0.0262 (2) | |
Cl2 | −0.29934 (12) | 0.0401 (3) | 0.13026 (17) | 0.0600 (8) | |
S2 | −0.33700 (12) | 0.0103 (2) | −0.05997 (15) | 0.0374 (6) | |
O2 | −0.3221 (4) | 0.3533 (6) | 0.0808 (4) | 0.0482 (18) | |
N21 | −0.3269 (4) | 0.2078 (7) | −0.0056 (5) | 0.0278 (17) | |
N22 | −0.2641 (4) | 0.1774 (6) | −0.1137 (5) | 0.034 (2) | |
N23 | −0.2616 (4) | 0.2893 (7) | −0.1375 (5) | 0.0343 (19) | |
C31 | −0.3042 (5) | 0.1443 (8) | −0.0587 (6) | 0.029 (2) | |
C32 | −0.2502 (4) | 0.3664 (9) | −0.0853 (5) | 0.035 (2) | |
C33 | −0.2357 (5) | 0.3394 (8) | −0.0008 (6) | 0.036 (2) | |
H331 | −0.2096 | 0.2725 | 0.0119 | 0.02 (2)* | |
H332 | −0.2200 | 0.3994 | 0.0346 | 0.05 (3)* | |
C34 | −0.2970 (4) | 0.3052 (8) | 0.0298 (6) | 0.033 (2) | |
C35 | −0.2544 (4) | 0.4866 (8) | −0.1106 (6) | 0.034 (2) | |
C36 | −0.2631 (5) | 0.5740 (10) | −0.0608 (7) | 0.045 (3) | |
H36 | −0.2640 | 0.5624 | −0.0077 | 0.08 (4)* | |
C37 | −0.2694 (5) | 0.6847 (11) | −0.0881 (10) | 0.056 (4) | |
H37 | −0.2886 | 0.7066 | −0.0442 | 0.16 (10)* | |
C38 | −0.2675 (6) | 0.7076 (12) | −0.1650 (9) | 0.062 (4) | |
H38 | −0.2788 | 0.7780 | −0.1862 | 0.073 (7)* | |
C39 | −0.2572 (6) | 0.6224 (11) | −0.2162 (8) | 0.054 (3) | |
H39 | −0.2643 | 0.6558 | −0.2651 | 0.06 (3)* | |
C40 | −0.2513 (5) | 0.5113 (10) | −0.1917 (6) | 0.046 (3) | |
H40 | −0.2508 | 0.4548 | −0.2290 | 0.03 (2)* | |
C41 | −0.2441 (7) | 0.0992 (11) | −0.1707 (8) | 0.061 (4) | |
H411 | −0.2251 | 0.1402 | −0.2105 | 0.073 (7)* | |
H412 | −0.2813 | 0.0579 | −0.1937 | 0.073 (7)* | |
H413 | −0.2126 | 0.0474 | −0.1458 | 0.073 (7)* | |
C42 | −0.4880 (5) | 0.1199 (10) | −0.0234 (6) | 0.032 (2) | |
C43 | −0.4680 (5) | 0.0066 (9) | 0.0972 (7) | 0.040 (3) | |
H43 | −0.4610 | −0.0571 | 0.1285 | 0.04 (3)* | |
C44 | −0.4862 (4) | 0.0135 (9) | 0.0163 (6) | 0.036 (2) | |
H44 | −0.4930 | −0.0569 | −0.0071 | 0.073 (7)* | |
C45 | −0.4505 (5) | 0.1044 (8) | 0.1422 (6) | 0.037 (3) | |
C46 | −0.4716 (5) | 0.2171 (8) | 0.0207 (6) | 0.036 (2) | |
H46 | −0.4711 | 0.2870 | −0.0037 | 0.073 (7)* | |
C47 | −0.4536 (5) | 0.2095 (11) | 0.1040 (7) | 0.044 (3) | |
H47 | −0.4369 | 0.2710 | 0.1332 | 0.06 (4)* | |
C48 | −0.5075 (5) | 0.1226 (9) | −0.1103 (6) | 0.040 (2) | |
H48 | −0.5015 | 0.0468 | −0.1311 | 0.073 (7)* | |
C49 | −0.5824 (5) | 0.1299 (11) | −0.1259 (7) | 0.057 (3) | |
H491 | −0.5978 | 0.1914 | −0.0966 | 0.073 (7)* | |
H492 | −0.6013 | 0.0605 | −0.1104 | 0.073 (7)* | |
H493 | −0.5947 | 0.1425 | −0.1804 | 0.073 (7)* | |
C50 | −0.4772 (6) | 0.2195 (12) | −0.1507 (7) | 0.065 (3) | |
H501 | −0.4326 | 0.2284 | −0.1294 | 0.073 (7)* | |
H502 | −0.5007 | 0.2879 | −0.1428 | 0.073 (7)* | |
H503 | −0.4791 | 0.2040 | −0.2054 | 0.073 (7)* | |
C51 | −0.4297 (7) | 0.0938 (12) | 0.2274 (7) | 0.060 (4) | |
H511 | −0.3839 | 0.1087 | 0.2374 | 0.08 (5)* | |
H512 | −0.4386 | 0.0186 | 0.2443 | 0.20 (11)* | |
H513 | −0.4533 | 0.1472 | 0.2554 | 0.14 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.0262 (3) | 0.0247 (4) | 0.0291 (4) | 0.0012 (3) | 0.0028 (3) | −0.0014 (3) |
Cl1 | 0.0382 (13) | 0.076 (2) | 0.0432 (16) | −0.0151 (12) | 0.0005 (11) | −0.0119 (13) |
S1 | 0.0377 (12) | 0.0289 (13) | 0.0401 (15) | 0.0047 (9) | 0.0086 (11) | 0.0075 (10) |
O1 | 0.066 (5) | 0.047 (5) | 0.041 (5) | 0.021 (4) | 0.018 (4) | 0.018 (4) |
N1 | 0.038 (4) | 0.025 (4) | 0.029 (5) | 0.002 (3) | 0.013 (4) | 0.001 (3) |
N2 | 0.046 (5) | 0.033 (5) | 0.046 (6) | 0.004 (4) | 0.007 (5) | 0.010 (4) |
N3 | 0.036 (4) | 0.039 (5) | 0.032 (5) | 0.007 (4) | 0.007 (3) | 0.001 (4) |
C1 | 0.033 (5) | 0.031 (6) | 0.021 (5) | 0.004 (4) | 0.004 (4) | 0.003 (4) |
C2 | 0.029 (4) | 0.032 (5) | 0.031 (5) | 0.011 (4) | 0.010 (4) | −0.001 (4) |
C3 | 0.039 (5) | 0.035 (6) | 0.041 (6) | 0.008 (4) | −0.008 (4) | −0.006 (4) |
C4 | 0.036 (5) | 0.037 (6) | 0.027 (6) | 0.012 (4) | −0.003 (4) | −0.002 (4) |
C5 | 0.027 (4) | 0.044 (6) | 0.030 (6) | 0.013 (4) | 0.001 (4) | −0.002 (4) |
C6 | 0.031 (5) | 0.045 (7) | 0.041 (7) | 0.005 (4) | 0.002 (5) | 0.008 (5) |
C7 | 0.031 (5) | 0.038 (7) | 0.068 (9) | 0.011 (4) | 0.016 (5) | 0.009 (6) |
C8 | 0.046 (6) | 0.031 (7) | 0.071 (9) | −0.003 (5) | 0.006 (6) | −0.005 (5) |
C9 | 0.056 (7) | 0.045 (7) | 0.041 (8) | −0.001 (5) | 0.012 (6) | −0.005 (5) |
C10 | 0.034 (5) | 0.043 (7) | 0.049 (8) | 0.002 (5) | 0.003 (5) | 0.008 (5) |
C11 | 0.069 (8) | 0.048 (7) | 0.055 (8) | 0.020 (6) | 0.038 (6) | 0.020 (6) |
C12 | 0.024 (4) | 0.028 (6) | 0.033 (6) | −0.001 (4) | 0.002 (4) | −0.005 (4) |
C13 | 0.023 (4) | 0.025 (5) | 0.042 (6) | 0.003 (4) | 0.008 (4) | 0.003 (4) |
C14 | 0.041 (5) | 0.031 (6) | 0.037 (6) | −0.005 (4) | 0.001 (5) | −0.002 (5) |
C15 | 0.043 (6) | 0.034 (6) | 0.043 (7) | −0.002 (5) | 0.008 (5) | 0.005 (5) |
C16 | 0.044 (6) | 0.040 (7) | 0.039 (7) | −0.003 (5) | −0.001 (5) | 0.010 (5) |
C17 | 0.026 (5) | 0.044 (7) | 0.052 (8) | −0.012 (5) | 0.010 (5) | −0.002 (5) |
C18 | 0.036 (5) | 0.051 (7) | 0.035 (6) | −0.012 (5) | 0.004 (5) | −0.003 (5) |
C19 | 0.046 (6) | 0.086 (9) | 0.038 (7) | 0.010 (6) | −0.011 (5) | −0.005 (6) |
C20 | 0.062 (8) | 0.072 (9) | 0.039 (7) | 0.003 (6) | 0.003 (6) | −0.017 (5) |
C21 | 0.060 (8) | 0.070 (9) | 0.047 (8) | −0.006 (7) | 0.002 (6) | 0.013 (6) |
Ru2 | 0.0265 (3) | 0.0255 (4) | 0.0269 (4) | −0.0008 (3) | 0.0037 (3) | 0.0019 (3) |
Cl2 | 0.0378 (13) | 0.091 (2) | 0.0508 (18) | 0.0139 (14) | 0.0010 (12) | 0.0214 (15) |
S2 | 0.0424 (13) | 0.0289 (13) | 0.0432 (16) | −0.0053 (10) | 0.0148 (12) | −0.0066 (10) |
O2 | 0.054 (4) | 0.051 (5) | 0.040 (4) | −0.008 (4) | 0.010 (4) | −0.014 (4) |
N21 | 0.031 (4) | 0.028 (4) | 0.025 (4) | −0.003 (3) | 0.006 (3) | −0.003 (3) |
N22 | 0.035 (4) | 0.033 (5) | 0.036 (5) | −0.005 (3) | 0.014 (4) | −0.005 (4) |
N23 | 0.043 (4) | 0.035 (5) | 0.026 (5) | −0.009 (4) | 0.011 (3) | 0.000 (3) |
C31 | 0.030 (5) | 0.025 (5) | 0.033 (6) | 0.003 (4) | 0.009 (5) | −0.005 (4) |
C32 | 0.028 (5) | 0.047 (6) | 0.028 (6) | −0.008 (4) | 0.000 (4) | −0.003 (4) |
C33 | 0.035 (5) | 0.028 (6) | 0.042 (7) | −0.001 (4) | −0.005 (4) | −0.011 (4) |
C34 | 0.037 (5) | 0.030 (5) | 0.030 (6) | 0.007 (4) | −0.003 (5) | 0.000 (4) |
C35 | 0.027 (4) | 0.038 (6) | 0.037 (6) | −0.013 (4) | 0.003 (4) | 0.003 (4) |
C36 | 0.035 (5) | 0.054 (7) | 0.046 (8) | −0.006 (5) | 0.006 (5) | 0.000 (6) |
C37 | 0.034 (6) | 0.045 (8) | 0.089 (12) | −0.007 (5) | 0.011 (7) | 0.007 (7) |
C38 | 0.041 (6) | 0.059 (9) | 0.084 (12) | −0.006 (6) | −0.006 (6) | 0.014 (8) |
C39 | 0.058 (7) | 0.058 (8) | 0.043 (8) | −0.009 (6) | 0.002 (6) | 0.012 (6) |
C40 | 0.053 (6) | 0.049 (7) | 0.035 (7) | −0.020 (5) | 0.006 (5) | 0.010 (5) |
C41 | 0.065 (8) | 0.078 (10) | 0.045 (8) | −0.022 (6) | 0.038 (7) | −0.017 (6) |
C42 | 0.024 (5) | 0.049 (6) | 0.025 (6) | −0.007 (4) | 0.010 (4) | 0.002 (4) |
C43 | 0.039 (5) | 0.034 (6) | 0.048 (7) | 0.004 (4) | 0.015 (5) | 0.011 (5) |
C44 | 0.031 (5) | 0.035 (6) | 0.038 (6) | −0.002 (4) | −0.013 (4) | −0.002 (4) |
C45 | 0.034 (5) | 0.043 (7) | 0.031 (6) | −0.005 (4) | −0.006 (4) | 0.008 (4) |
C46 | 0.040 (5) | 0.024 (6) | 0.043 (7) | 0.001 (4) | −0.003 (5) | 0.011 (4) |
C47 | 0.034 (5) | 0.045 (7) | 0.054 (8) | 0.007 (5) | 0.014 (5) | −0.008 (6) |
C48 | 0.051 (6) | 0.034 (6) | 0.037 (6) | 0.008 (5) | 0.003 (5) | 0.001 (5) |
C49 | 0.048 (6) | 0.067 (8) | 0.052 (8) | 0.004 (6) | −0.015 (6) | −0.003 (6) |
C50 | 0.072 (8) | 0.091 (10) | 0.029 (7) | −0.001 (7) | −0.001 (6) | 0.020 (6) |
C51 | 0.068 (8) | 0.090 (11) | 0.020 (6) | −0.002 (7) | 0.004 (6) | 0.008 (6) |
Ru1—N1 | 2.099 (8) | Ru2—N21 | 2.095 (8) |
Ru1—C17 | 2.119 (10) | Ru2—C46 | 2.171 (9) |
Ru1—C13 | 2.171 (9) | Ru2—C47 | 2.194 (11) |
Ru1—C14 | 2.174 (12) | Ru2—C42 | 2.196 (10) |
Ru1—C12 | 2.174 (9) | Ru2—C44 | 2.199 (9) |
Ru1—C16 | 2.180 (11) | Ru2—C43 | 2.213 (11) |
Ru1—C15 | 2.214 (12) | Ru2—C45 | 2.219 (12) |
Ru1—Cl1 | 2.404 (2) | Ru2—Cl2 | 2.404 (2) |
Ru1—S1 | 2.446 (3) | Ru2—S2 | 2.429 (3) |
S1—C1 | 1.731 (10) | S2—C31 | 1.724 (10) |
O1—C4 | 1.230 (12) | O2—C34 | 1.212 (12) |
N1—C1 | 1.342 (13) | N21—C31 | 1.310 (13) |
N1—C4 | 1.364 (12) | N21—C34 | 1.415 (12) |
N2—C1 | 1.354 (14) | N22—C31 | 1.383 (14) |
N2—N3 | 1.406 (12) | N22—N23 | 1.391 (11) |
N2—C11 | 1.473 (14) | N22—C41 | 1.444 (14) |
N3—C2 | 1.257 (12) | N23—C32 | 1.287 (12) |
C2—C3 | 1.492 (14) | C32—C35 | 1.488 (14) |
C2—C5 | 1.496 (14) | C32—C33 | 1.492 (14) |
C3—C4 | 1.522 (14) | C33—C34 | 1.481 (14) |
C3—H31 | 0.9697 | C33—H331 | 0.9688 |
C3—H32 | 0.9702 | C33—H332 | 0.9694 |
C5—C10 | 1.378 (16) | C35—C36 | 1.371 (16) |
C5—C6 | 1.406 (14) | C35—C40 | 1.438 (15) |
C6—C7 | 1.396 (15) | C36—C37 | 1.394 (17) |
C6—H6 | 0.9300 | C36—H36 | 0.9300 |
C7—C8 | 1.344 (16) | C37—C38 | 1.36 (2) |
C7—H7 | 0.9300 | C37—H37 | 0.9305 |
C8—C9 | 1.364 (17) | C38—C39 | 1.37 (2) |
C8—H8 | 0.9300 | C38—H38 | 0.9299 |
C9—C10 | 1.398 (17) | C39—C40 | 1.383 (16) |
C9—H9 | 0.98 (11) | C39—H39 | 0.9301 |
C10—H10 | 0.70 (14) | C40—H40 | 0.9300 |
C11—H111 | 0.8200 | C41—H411 | 0.9600 |
C11—H112 | 0.9600 | C41—H412 | 0.9600 |
C11—H113 | 0.9600 | C41—H413 | 0.9600 |
C12—C17 | 1.387 (15) | C42—C46 | 1.401 (15) |
C12—C13 | 1.412 (13) | C42—C44 | 1.432 (15) |
C12—C18 | 1.525 (16) | C42—C48 | 1.512 (16) |
C13—C14 | 1.381 (15) | C43—C44 | 1.410 (15) |
C13—H13 | 0.87 (13) | C43—C45 | 1.419 (15) |
C14—C15 | 1.463 (15) | C43—H43 | 0.9299 |
C14—H14 | 0.9303 | C44—H44 | 0.9298 |
C15—C16 | 1.361 (16) | C45—C47 | 1.406 (16) |
C15—C21 | 1.511 (16) | C45—C51 | 1.494 (16) |
C16—C17 | 1.434 (16) | C46—C47 | 1.448 (16) |
C16—H16 | 0.9302 | C46—H46 | 0.9301 |
C17—H17 | 0.9300 | C47—H47 | 0.9297 |
C18—C20 | 1.522 (16) | C48—C50 | 1.513 (17) |
C18—C19 | 1.532 (15) | C48—C49 | 1.543 (15) |
C18—H18 | 0.9798 | C48—H48 | 0.9794 |
C19—H191 | 0.8200 | C49—H491 | 0.9600 |
C19—H192 | 0.9600 | C49—H492 | 0.9600 |
C19—H193 | 0.9600 | C49—H493 | 0.9600 |
C20—H201 | 0.8200 | C50—H501 | 0.9600 |
C20—H202 | 0.9600 | C50—H502 | 0.9600 |
C20—H203 | 0.9599 | C50—H503 | 0.9600 |
C21—H211 | 0.8200 | C51—H511 | 0.9600 |
C21—H212 | 0.9601 | C51—H512 | 0.9600 |
C21—H213 | 0.9599 | C51—H513 | 0.9600 |
N1—Ru1—C17 | 95.0 (4) | N21—Ru2—C46 | 92.1 (3) |
N1—Ru1—C13 | 154.9 (3) | N21—Ru2—C47 | 104.6 (4) |
C17—Ru1—C13 | 68.2 (4) | C46—Ru2—C47 | 38.8 (4) |
N1—Ru1—C14 | 162.8 (3) | N21—Ru2—C42 | 107.7 (3) |
C17—Ru1—C14 | 81.2 (4) | C46—Ru2—C42 | 37.4 (4) |
C13—Ru1—C14 | 37.1 (4) | C47—Ru2—C42 | 68.7 (4) |
N1—Ru1—C12 | 118.1 (3) | N21—Ru2—C44 | 142.4 (3) |
C17—Ru1—C12 | 37.7 (4) | C46—Ru2—C44 | 67.5 (4) |
C13—Ru1—C12 | 37.9 (3) | C47—Ru2—C44 | 79.6 (4) |
C14—Ru1—C12 | 68.2 (4) | C42—Ru2—C44 | 38.0 (4) |
N1—Ru1—C16 | 99.6 (3) | N21—Ru2—C43 | 171.1 (4) |
C17—Ru1—C16 | 38.9 (4) | C46—Ru2—C43 | 79.9 (4) |
C13—Ru1—C16 | 79.3 (4) | C47—Ru2—C43 | 66.6 (5) |
C14—Ru1—C16 | 67.0 (4) | C42—Ru2—C43 | 68.3 (4) |
C12—Ru1—C16 | 68.2 (4) | C44—Ru2—C43 | 37.3 (4) |
N1—Ru1—C15 | 124.1 (4) | N21—Ru2—C45 | 135.5 (3) |
C17—Ru1—C15 | 68.9 (4) | C46—Ru2—C45 | 68.9 (4) |
C13—Ru1—C15 | 68.6 (4) | C47—Ru2—C45 | 37.1 (4) |
C14—Ru1—C15 | 38.9 (4) | C42—Ru2—C45 | 81.6 (4) |
C12—Ru1—C15 | 81.5 (4) | C44—Ru2—C45 | 67.9 (4) |
C16—Ru1—C15 | 36.1 (4) | C43—Ru2—C45 | 37.3 (4) |
N1—Ru1—Cl1 | 85.7 (2) | N21—Ru2—Cl2 | 86.1 (2) |
C17—Ru1—Cl1 | 157.5 (3) | C46—Ru2—Cl2 | 146.0 (3) |
C13—Ru1—Cl1 | 117.1 (3) | C47—Ru2—Cl2 | 109.2 (3) |
C14—Ru1—Cl1 | 91.5 (3) | C42—Ru2—Cl2 | 166.1 (3) |
C12—Ru1—Cl1 | 154.8 (2) | C44—Ru2—Cl2 | 128.6 (3) |
C16—Ru1—Cl1 | 118.7 (3) | C43—Ru2—Cl2 | 98.1 (3) |
C15—Ru1—Cl1 | 92.1 (3) | C45—Ru2—Cl2 | 88.9 (3) |
N1—Ru1—S1 | 66.5 (2) | N21—Ru2—S2 | 67.2 (2) |
C17—Ru1—S1 | 115.8 (3) | C46—Ru2—S2 | 123.9 (3) |
C13—Ru1—S1 | 103.1 (3) | C47—Ru2—S2 | 162.2 (3) |
C14—Ru1—S1 | 130.2 (3) | C42—Ru2—S2 | 98.1 (3) |
C12—Ru1—S1 | 96.4 (3) | C44—Ru2—S2 | 97.4 (3) |
C16—Ru1—S1 | 152.3 (3) | C43—Ru2—S2 | 120.7 (3) |
C15—Ru1—S1 | 168.8 (3) | C45—Ru2—S2 | 156.4 (3) |
Cl1—Ru1—S1 | 85.19 (9) | Cl2—Ru2—S2 | 86.53 (10) |
C1—S1—Ru1 | 80.3 (4) | C31—S2—Ru2 | 79.0 (3) |
C1—N1—C4 | 125.9 (8) | C31—N21—C34 | 126.7 (8) |
C1—N1—Ru1 | 103.8 (6) | C31—N21—Ru2 | 102.3 (6) |
C4—N1—Ru1 | 128.5 (7) | C34—N21—Ru2 | 126.9 (7) |
C1—N2—N3 | 122.5 (8) | C31—N22—N23 | 121.1 (8) |
C1—N2—C11 | 119.5 (9) | C31—N22—C41 | 121.6 (8) |
N3—N2—C11 | 113.9 (9) | N23—N22—C41 | 112.7 (9) |
C2—N3—N2 | 117.1 (8) | C32—N23—N22 | 118.5 (8) |
N1—C1—N2 | 127.6 (8) | N21—C31—N22 | 127.2 (9) |
N1—C1—S1 | 108.9 (7) | N21—C31—S2 | 111.5 (7) |
N2—C1—S1 | 123.3 (7) | N22—C31—S2 | 121.0 (7) |
N3—C2—C3 | 122.7 (9) | N23—C32—C35 | 118.1 (9) |
N3—C2—C5 | 114.8 (8) | N23—C32—C33 | 122.4 (9) |
C3—C2—C5 | 122.4 (8) | C35—C32—C33 | 119.5 (8) |
C2—C3—C4 | 108.0 (7) | C34—C33—C32 | 108.6 (7) |
C2—C3—H31 | 113.1 | C34—C33—H331 | 99.9 |
C4—C3—H31 | 110.8 | C32—C33—H331 | 116.4 |
C2—C3—H32 | 108.6 | C34—C33—H332 | 102.5 |
C4—C3—H32 | 107.9 | C32—C33—H332 | 118.5 |
H31—C3—H32 | 108.4 | H331—C33—H332 | 108.4 |
O1—C4—N1 | 122.7 (9) | O2—C34—N21 | 119.8 (9) |
O1—C4—C3 | 122.4 (8) | O2—C34—C33 | 125.6 (9) |
N1—C4—C3 | 114.9 (9) | N21—C34—C33 | 114.7 (8) |
C10—C5—C6 | 118.8 (10) | C36—C35—C40 | 118.7 (10) |
C10—C5—C2 | 120.8 (9) | C36—C35—C32 | 123.0 (10) |
C6—C5—C2 | 120.4 (9) | C40—C35—C32 | 118.3 (10) |
C7—C6—C5 | 119.0 (11) | C35—C36—C37 | 120.7 (12) |
C7—C6—H6 | 120.5 | C35—C36—H36 | 121.8 |
C5—C6—H6 | 120.5 | C37—C36—H36 | 117.5 |
C8—C7—C6 | 121.1 (11) | C38—C37—C36 | 120.4 (14) |
C8—C7—H7 | 119.5 | C38—C37—H37 | 143.3 |
C6—C7—H7 | 119.5 | C36—C37—H37 | 91.0 |
C7—C8—C9 | 120.8 (11) | C37—C38—C39 | 120.4 (13) |
C7—C8—H8 | 119.6 | C37—C38—H38 | 122.0 |
C9—C8—H8 | 119.6 | C39—C38—H38 | 117.1 |
C8—C9—C10 | 119.8 (11) | C38—C39—C40 | 121.1 (13) |
C8—C9—H9 | 128 (5) | C38—C39—H39 | 104.7 |
C10—C9—H9 | 112 (5) | C40—C39—H39 | 133.0 |
C5—C10—C9 | 120.4 (10) | C39—C40—C35 | 118.7 (12) |
C5—C10—H10 | 123 (10) | C39—C40—H40 | 118.6 |
C9—C10—H10 | 116 (10) | C35—C40—H40 | 122.2 |
N2—C11—H111 | 109.5 | N22—C41—H411 | 109.5 |
N2—C11—H112 | 109.4 | N22—C41—H412 | 109.5 |
H111—C11—H112 | 109.2 | H411—C41—H412 | 109.5 |
N2—C11—H113 | 110.0 | N22—C41—H413 | 109.5 |
H111—C11—H113 | 109.3 | H411—C41—H413 | 109.5 |
H112—C11—H113 | 109.5 | H412—C41—H413 | 109.5 |
C17—C12—C13 | 118.3 (10) | C46—C42—C44 | 118.0 (9) |
C17—C12—C18 | 124.5 (9) | C46—C42—C48 | 123.1 (10) |
C13—C12—C18 | 117.2 (8) | C44—C42—C48 | 118.9 (9) |
C17—C12—Ru1 | 69.0 (6) | C46—C42—Ru2 | 70.3 (6) |
C13—C12—Ru1 | 70.9 (5) | C44—C42—Ru2 | 71.1 (5) |
C18—C12—Ru1 | 129.8 (7) | C48—C42—Ru2 | 130.1 (7) |
C14—C13—C12 | 121.6 (9) | C44—C43—C45 | 121.3 (9) |
C14—C13—Ru1 | 71.6 (6) | C44—C43—Ru2 | 70.8 (6) |
C12—C13—Ru1 | 71.2 (5) | C45—C43—Ru2 | 71.5 (6) |
C14—C13—H13 | 133 (9) | C44—C43—H43 | 129.2 |
C12—C13—H13 | 106 (9) | C45—C43—H43 | 109.2 |
Ru1—C13—H13 | 134 (9) | Ru2—C43—H43 | 124.9 |
C13—C14—C15 | 120.6 (9) | C43—C44—C42 | 121.0 (9) |
C13—C14—Ru1 | 71.3 (6) | C43—C44—Ru2 | 71.9 (5) |
C15—C14—Ru1 | 72.0 (6) | C42—C44—Ru2 | 70.9 (5) |
C13—C14—H14 | 148.7 | C43—C44—H44 | 112.9 |
C15—C14—H14 | 90.4 | C42—C44—H44 | 125.8 |
Ru1—C14—H14 | 128.2 | Ru2—C44—H44 | 125.9 |
C16—C15—C14 | 116.6 (10) | C47—C45—C43 | 118.0 (11) |
C16—C15—C21 | 121.7 (11) | C47—C45—C51 | 122.0 (11) |
C14—C15—C21 | 121.6 (11) | C43—C45—C51 | 120.0 (10) |
C16—C15—Ru1 | 70.6 (7) | C47—C45—Ru2 | 70.5 (7) |
C14—C15—Ru1 | 69.1 (6) | C43—C45—Ru2 | 71.1 (7) |
C21—C15—Ru1 | 128.7 (8) | C51—C45—Ru2 | 129.9 (8) |
C15—C16—C17 | 122.7 (10) | C42—C46—C47 | 120.7 (10) |
C15—C16—Ru1 | 73.3 (7) | C42—C46—Ru2 | 72.3 (6) |
C17—C16—Ru1 | 68.2 (6) | C47—C46—Ru2 | 71.5 (6) |
C15—C16—H16 | 104.4 | C42—C46—H46 | 119.8 |
C17—C16—H16 | 132.7 | C47—C46—H46 | 119.5 |
Ru1—C16—H16 | 137.3 | Ru2—C46—H46 | 127.5 |
C12—C17—C16 | 119.9 (11) | C45—C47—C46 | 120.9 (11) |
C12—C17—Ru1 | 73.3 (6) | C45—C47—Ru2 | 72.4 (7) |
C16—C17—Ru1 | 72.8 (6) | C46—C47—Ru2 | 69.8 (6) |
C12—C17—H17 | 132.6 | C45—C47—H47 | 116.3 |
C16—C17—H17 | 104.9 | C46—C47—H47 | 122.0 |
Ru1—C17—H17 | 139.0 | Ru2—C47—H47 | 122.1 |
C20—C18—C12 | 112.6 (9) | C42—C48—C50 | 113.3 (9) |
C20—C18—C19 | 110.5 (9) | C42—C48—C49 | 109.2 (9) |
C12—C18—C19 | 107.3 (9) | C50—C48—C49 | 109.5 (9) |
C20—C18—H18 | 99.4 | C42—C48—H48 | 108.3 |
C12—C18—H18 | 103.7 | C50—C48—H48 | 116.8 |
C19—C18—H18 | 123.1 | C49—C48—H48 | 98.7 |
C18—C19—H191 | 109.5 | C48—C49—H491 | 109.5 |
C18—C19—H192 | 108.9 | C48—C49—H492 | 109.5 |
H191—C19—H192 | 109.7 | H491—C49—H492 | 109.5 |
C18—C19—H193 | 109.6 | C48—C49—H493 | 109.5 |
H191—C19—H193 | 109.7 | H491—C49—H493 | 109.5 |
H192—C19—H193 | 109.5 | H492—C49—H493 | 109.5 |
C18—C20—H201 | 109.5 | C48—C50—H501 | 109.5 |
C18—C20—H202 | 108.6 | C48—C50—H502 | 109.5 |
H201—C20—H202 | 109.4 | H501—C50—H502 | 109.5 |
C18—C20—H203 | 110.5 | C48—C50—H503 | 109.5 |
H201—C20—H203 | 109.4 | H501—C50—H503 | 109.5 |
H202—C20—H203 | 109.5 | H502—C50—H503 | 109.5 |
C15—C21—H211 | 109.5 | C45—C51—H511 | 109.5 |
C15—C21—H212 | 109.2 | C45—C51—H512 | 109.5 |
H211—C21—H212 | 109.3 | H511—C51—H512 | 109.5 |
C15—C21—H213 | 110.1 | C45—C51—H513 | 109.5 |
H211—C21—H213 | 109.2 | H511—C51—H513 | 109.5 |
H212—C21—H213 | 109.5 | H512—C51—H513 | 109.5 |
Experimental details
Crystal data | |
Chemical formula | [RuCl(C10H14)(C10H11N3OS)] |
Mr | 503.01 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 293 |
a, b, c (Å) | 20.647 (2), 11.835 (1), 17.275 (2) |
β (°) | 96.253 (5) |
V (Å3) | 4196.2 (7) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 8.28 |
Crystal size (mm) | 0.7 × 0.2 × 0.2 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (using ΔF; Parkin et al., 1995) |
Tmin, Tmax | 0.050, 0.189 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8671, 5007, 4791 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.119, 1.03 |
No. of reflections | 5007 |
No. of parameters | 584 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.95, −0.80 |
Absolute structure | Flack (1983), Friedel pairs merged |
Absolute structure parameter | 0.467 (14) |
Computer programs: COLLECT (Nonius, 1998), HKL (Otwinowski & Minor, 1997), HKL, DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1992), SHELXL97.
Heterocylic compounds have found widespread application in both pharmacology as active drugs (Pauwels et al., 1990; Koop et al., 1991) and chemistry as useful reaction intermediates in organic synthesis (Anderson & Raju, 1989; Steinmeyer & Neef, 1992). They are also good ligands which coordinate readily with transition metals to provide versatile and useful complexes (Ghosh et al., 1998; Wills, 1998; Shi et al., 1999). However, the preparation of transition metal complexes with 1,2,4-tiazepines as ligands is not well documented. This can probably be ascribed to the difficulty of synthesis of these heterocycles and to the triazepine nucleus instability (Ait Itto et al., 1997).
In the course of our research on transition metal complexes (El Firdoussi et al., 1993, 1997; Abouhamza et al., 1999), we report here the crystal structure of a new triazepine based ruthenium(II) complex, namely Chloro(η6-p-cymene)(2-methyl-5-oxo-7-phenyl-5,6-dihydro-2H-1,2,4-triazepin- 3-thiolato-κ2N4,S)ruthenium(II), (II). This kind of complex which has a great conformational rigidity could lead to catalysts of high selectivity. The title compound was prepared by reaction in 2-propanol of the 1,2,4-triazepine (I) with [Ru(p-cymene)Cl2]2 in the presence of triethylamine. Crystals were isolated and characterized by X-ray diffraction. Various complexes of the type [Ru(arene)(heteroatomic ligand)Cl] have been crystallographically characterized (Nishiyama et al., 1989; Suzuki et al., 1996).
Complex (II) is, to the best of our knowledge, the first structural example of a transition metal complex containing a 1,2,4-triazepine ligand. The latter acts as a bidentate ligand (through N1 and S1), forming a four-membered chelate ring. The p-cymene and Cl ligands complete the coordination sphere of the RuII atom.
The crystal structure has two similar molecules in its asymmetric unit pseudo-centrosymmetrically arranged, but no additional crystallographic symmetry was found (Le Page, 1987, 1988). Both molecules have the same arrangement and have very close geometries. Average distances involving ruthenium coordination: Ru—N 2.097 (8), Ru—Cl 2.404 (2), Ru—S 2.438 (3) and Ru–centroid 1.67 (1) Å. Average angles involving ruthenium coordination: N—Ru—Cl 85.9 (2), Cl—Ru—S 82.08 (9), N—Ru—S 66.8 (2), N—Ru—centroid 133.0 (3), S—Ru—centroid 135.3 (3) and Cl—Ru—centroid 128.3 (3)°.