The title compound, [Ru(C
18H
12N
5)Cl(C
8H
4N
2)(C
2H
6OS)], consists of an Ru
II atom hexagonally coordinated by a tridendate isoindoline ligand, a Cl atom, the S atom of a dimethyl sulfoxide molecule and an N atom of a CN group of dicyanobenzene. In the crystal structure, a three-dimensional network is built up owing to the presence of weak C—H
O and C—H
Cl intermolecular hydrogen bonds.
Supporting information
CCDC reference: 262242
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.094
- Data-to-parameter ratio = 20.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.15 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.22 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for N6 - C19 .. 6.53 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ru1 - Cl1 .. 9.13 su
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C19 - C20 ... 1.43 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C25 - C26 ... 1.44 Ang.
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 0.949
Tmax scaled 0.921 Tmin scaled 0.691
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
8 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2004); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
[1,3-Bis(2-pyridylimino)isoindolinato-
κ3N,
N',
N'']chloro(1,2-dicyanobenzene-
κN)(dimethyl
sulfoxide-
κS)ruthenium(II)
top
Crystal data top
[Ru(C18H12N5)Cl(C8H4N2)(C2H6OS)] | F(000) = 1296 |
Mr = 641.11 | Dx = 1.642 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 40303 reflections |
a = 11.5299 (5) Å | θ = 1.8–29.6° |
b = 12.9081 (5) Å | µ = 0.83 mm−1 |
c = 17.4774 (9) Å | T = 153 K |
β = 94.538 (4)° | Block, dark_red |
V = 2593.0 (2) Å3 | 0.35 × 0.24 × 0.10 mm |
Z = 4 | |
Data collection top
Stoe IPDS-II diffractometer | 7199 independent reflections |
Radiation source: fine-focus sealed tube | 6291 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 29.6°, θmin = 2.0° |
Absorption correction: multi-scan (MULrefABS in PLATON; Spek, 2003) | h = −15→15 |
Tmin = 0.728, Tmax = 0.970 | k = −17→17 |
37823 measured reflections | l = −24→24 |
Refinement top
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0441P)2 + 3.0086P] where P = (Fo2 + 2Fc2)/3 |
7199 reflections | (Δ/σ)max = 0.001 |
354 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.98 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All su's are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ru1 | 0.46569 (1) | 0.33773 (1) | 0.27080 (1) | 0.0225 (1) | |
Cl1 | 0.33623 (5) | 0.35500 (5) | 0.15468 (4) | 0.0295 (2) | |
S1 | 0.58304 (6) | 0.32097 (5) | 0.37623 (4) | 0.0302 (2) | |
O1 | 0.56308 (19) | 0.23245 (18) | 0.42604 (13) | 0.0431 (7) | |
N1 | 0.48688 (18) | 0.17767 (15) | 0.25140 (13) | 0.0263 (5) | |
N2 | 0.63069 (18) | 0.19282 (16) | 0.15703 (12) | 0.0277 (6) | |
N3 | 0.59775 (17) | 0.36426 (15) | 0.20611 (12) | 0.0242 (5) | |
N4 | 0.62250 (19) | 0.54847 (16) | 0.22296 (14) | 0.0307 (6) | |
N5 | 0.45035 (17) | 0.49807 (15) | 0.28520 (12) | 0.0253 (5) | |
N6 | 0.32508 (18) | 0.30844 (16) | 0.33006 (12) | 0.0263 (5) | |
N7 | 0.1547 (3) | 0.4996 (2) | 0.47166 (18) | 0.0497 (9) | |
C1 | 0.4272 (2) | 0.1088 (2) | 0.29132 (17) | 0.0340 (8) | |
C2 | 0.4264 (2) | 0.0037 (2) | 0.28020 (18) | 0.0360 (8) | |
C3 | 0.4929 (3) | −0.03681 (19) | 0.22503 (18) | 0.0356 (8) | |
C4 | 0.5575 (3) | 0.0305 (2) | 0.18498 (16) | 0.0342 (8) | |
C5 | 0.5555 (2) | 0.13740 (18) | 0.19918 (15) | 0.0266 (6) | |
C6 | 0.6481 (2) | 0.29164 (19) | 0.16261 (14) | 0.0251 (6) | |
C7 | 0.7338 (2) | 0.34367 (19) | 0.11736 (15) | 0.0275 (6) | |
C8 | 0.8067 (2) | 0.3068 (2) | 0.06452 (16) | 0.0311 (7) | |
C9 | 0.8730 (2) | 0.3787 (2) | 0.02800 (18) | 0.0391 (8) | |
C10 | 0.8655 (3) | 0.4838 (2) | 0.0446 (2) | 0.0447 (9) | |
C11 | 0.7951 (2) | 0.5201 (2) | 0.09955 (19) | 0.0400 (9) | |
C12 | 0.7300 (2) | 0.4482 (2) | 0.13548 (15) | 0.0293 (7) | |
C13 | 0.6444 (2) | 0.45926 (18) | 0.19302 (15) | 0.0271 (6) | |
C14 | 0.5321 (2) | 0.56760 (19) | 0.26785 (15) | 0.0279 (6) | |
C15 | 0.5256 (3) | 0.6714 (2) | 0.29218 (18) | 0.0356 (8) | |
C16 | 0.4329 (3) | 0.7058 (2) | 0.32970 (18) | 0.0385 (8) | |
C17 | 0.3446 (3) | 0.6358 (2) | 0.34167 (18) | 0.0369 (8) | |
C18 | 0.3574 (2) | 0.5352 (2) | 0.31927 (17) | 0.0325 (7) | |
C19 | 0.2461 (2) | 0.28527 (19) | 0.36179 (15) | 0.0281 (6) | |
C20 | 0.1512 (2) | 0.2462 (2) | 0.40096 (14) | 0.0276 (6) | |
C21 | 0.1216 (2) | 0.1420 (2) | 0.39264 (15) | 0.0309 (7) | |
C22 | 0.0327 (2) | 0.1022 (2) | 0.43229 (17) | 0.0362 (8) | |
C23 | −0.0274 (2) | 0.1650 (2) | 0.47970 (17) | 0.0374 (8) | |
C24 | 0.0020 (2) | 0.2682 (2) | 0.48905 (15) | 0.0331 (7) | |
C25 | 0.0911 (2) | 0.3093 (2) | 0.45012 (15) | 0.0294 (7) | |
C26 | 0.1262 (2) | 0.4152 (2) | 0.46225 (17) | 0.0352 (8) | |
C27 | 0.7337 (3) | 0.3138 (3) | 0.3576 (2) | 0.0510 (10) | |
C28 | 0.5871 (5) | 0.4324 (3) | 0.4360 (2) | 0.0792 (16) | |
H1 | 0.38220 | 0.13530 | 0.33010 | 0.0410* | |
H2 | 0.38120 | −0.04030 | 0.30970 | 0.0430* | |
H3 | 0.49380 | −0.10910 | 0.21510 | 0.0430* | |
H4 | 0.60430 | 0.00430 | 0.14700 | 0.0410* | |
H8 | 0.81140 | 0.23490 | 0.05360 | 0.0370* | |
H9 | 0.92390 | 0.35580 | −0.00870 | 0.0470* | |
H10 | 0.90970 | 0.53180 | 0.01760 | 0.0540* | |
H11 | 0.79190 | 0.59170 | 0.11190 | 0.0480* | |
H15 | 0.58630 | 0.71820 | 0.28250 | 0.0430* | |
H16 | 0.42910 | 0.77540 | 0.34700 | 0.0460* | |
H17 | 0.27690 | 0.65730 | 0.36490 | 0.0440* | |
H18 | 0.29670 | 0.48800 | 0.32820 | 0.0390* | |
H21 | 0.16220 | 0.09860 | 0.35990 | 0.0370* | |
H22 | 0.01270 | 0.03110 | 0.42700 | 0.0430* | |
H23 | −0.08920 | 0.13690 | 0.50600 | 0.0450* | |
H24 | −0.03890 | 0.31080 | 0.52210 | 0.0400* | |
H27A | 0.74650 | 0.25250 | 0.32630 | 0.0770* | |
H27B | 0.78160 | 0.30890 | 0.40640 | 0.0770* | |
H27C | 0.75520 | 0.37620 | 0.33010 | 0.0770* | |
H28A | 0.61700 | 0.49150 | 0.40830 | 0.1190* | |
H28B | 0.63820 | 0.41920 | 0.48250 | 0.1190* | |
H28C | 0.50850 | 0.44800 | 0.45020 | 0.1190* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ru1 | 0.0219 (1) | 0.0182 (1) | 0.0281 (1) | 0.0007 (1) | 0.0056 (1) | −0.0001 (1) |
Cl1 | 0.0281 (3) | 0.0284 (3) | 0.0321 (3) | −0.0026 (2) | 0.0034 (2) | 0.0008 (2) |
S1 | 0.0312 (3) | 0.0272 (3) | 0.0319 (3) | 0.0035 (2) | 0.0014 (2) | 0.0007 (2) |
O1 | 0.0417 (11) | 0.0474 (12) | 0.0409 (11) | 0.0020 (9) | 0.0071 (9) | 0.0153 (9) |
N1 | 0.0269 (9) | 0.0178 (9) | 0.0347 (10) | 0.0017 (7) | 0.0051 (8) | 0.0010 (7) |
N2 | 0.0293 (10) | 0.0234 (9) | 0.0310 (10) | 0.0021 (8) | 0.0066 (8) | −0.0006 (8) |
N3 | 0.0237 (9) | 0.0210 (8) | 0.0288 (10) | −0.0011 (7) | 0.0082 (7) | −0.0020 (7) |
N4 | 0.0293 (10) | 0.0237 (9) | 0.0400 (12) | −0.0037 (8) | 0.0085 (9) | −0.0047 (8) |
N5 | 0.0265 (9) | 0.0187 (8) | 0.0311 (10) | 0.0037 (7) | 0.0042 (7) | −0.0017 (7) |
N6 | 0.0264 (9) | 0.0223 (9) | 0.0311 (10) | 0.0002 (7) | 0.0086 (8) | 0.0008 (7) |
N7 | 0.0534 (16) | 0.0373 (14) | 0.0590 (17) | 0.0007 (12) | 0.0092 (13) | −0.0076 (12) |
C1 | 0.0341 (13) | 0.0237 (11) | 0.0456 (15) | 0.0016 (10) | 0.0125 (11) | 0.0037 (10) |
C2 | 0.0348 (13) | 0.0226 (11) | 0.0514 (16) | −0.0005 (10) | 0.0089 (11) | 0.0045 (11) |
C3 | 0.0418 (14) | 0.0185 (10) | 0.0464 (15) | −0.0001 (10) | 0.0038 (12) | 0.0017 (10) |
C4 | 0.0433 (14) | 0.0222 (11) | 0.0378 (14) | 0.0015 (10) | 0.0085 (11) | −0.0029 (10) |
C5 | 0.0261 (11) | 0.0219 (10) | 0.0318 (12) | 0.0001 (8) | 0.0028 (9) | 0.0006 (9) |
C6 | 0.0216 (10) | 0.0270 (11) | 0.0266 (11) | 0.0022 (8) | 0.0017 (8) | −0.0009 (9) |
C7 | 0.0209 (10) | 0.0297 (11) | 0.0322 (12) | −0.0008 (8) | 0.0041 (8) | −0.0012 (9) |
C8 | 0.0269 (11) | 0.0318 (12) | 0.0351 (13) | −0.0007 (9) | 0.0058 (9) | −0.0038 (10) |
C9 | 0.0324 (13) | 0.0420 (15) | 0.0449 (15) | −0.0055 (11) | 0.0154 (11) | −0.0053 (12) |
C10 | 0.0384 (15) | 0.0395 (15) | 0.0595 (19) | −0.0136 (12) | 0.0246 (14) | −0.0040 (14) |
C11 | 0.0347 (13) | 0.0308 (13) | 0.0566 (18) | −0.0098 (11) | 0.0177 (12) | −0.0055 (12) |
C12 | 0.0229 (10) | 0.0297 (12) | 0.0360 (13) | −0.0033 (9) | 0.0063 (9) | −0.0031 (10) |
C13 | 0.0234 (10) | 0.0237 (11) | 0.0346 (12) | −0.0034 (8) | 0.0048 (9) | −0.0011 (9) |
C14 | 0.0279 (11) | 0.0233 (10) | 0.0329 (12) | 0.0007 (9) | 0.0043 (9) | −0.0014 (9) |
C15 | 0.0418 (14) | 0.0213 (11) | 0.0445 (15) | −0.0040 (10) | 0.0083 (11) | −0.0042 (10) |
C16 | 0.0467 (15) | 0.0224 (11) | 0.0474 (16) | 0.0041 (10) | 0.0103 (13) | −0.0047 (11) |
C17 | 0.0379 (14) | 0.0265 (12) | 0.0475 (16) | 0.0091 (10) | 0.0119 (12) | −0.0005 (11) |
C18 | 0.0311 (12) | 0.0245 (11) | 0.0429 (14) | 0.0040 (9) | 0.0084 (10) | −0.0012 (10) |
C19 | 0.0295 (11) | 0.0241 (10) | 0.0308 (12) | 0.0025 (9) | 0.0027 (9) | −0.0009 (9) |
C20 | 0.0252 (11) | 0.0290 (11) | 0.0289 (11) | 0.0012 (9) | 0.0042 (9) | 0.0020 (9) |
C21 | 0.0327 (12) | 0.0295 (12) | 0.0309 (12) | −0.0005 (9) | 0.0054 (9) | −0.0013 (9) |
C22 | 0.0383 (14) | 0.0338 (13) | 0.0370 (14) | −0.0072 (11) | 0.0055 (11) | 0.0036 (11) |
C23 | 0.0308 (12) | 0.0453 (16) | 0.0369 (14) | −0.0057 (11) | 0.0076 (10) | 0.0060 (12) |
C24 | 0.0261 (11) | 0.0441 (15) | 0.0297 (12) | 0.0049 (10) | 0.0060 (9) | 0.0009 (11) |
C25 | 0.0263 (11) | 0.0321 (12) | 0.0300 (12) | 0.0035 (9) | 0.0038 (9) | 0.0011 (9) |
C26 | 0.0325 (13) | 0.0355 (13) | 0.0382 (14) | 0.0043 (10) | 0.0071 (10) | −0.0033 (11) |
C27 | 0.0269 (13) | 0.067 (2) | 0.058 (2) | −0.0042 (14) | −0.0027 (13) | 0.0221 (17) |
C28 | 0.120 (4) | 0.055 (2) | 0.055 (2) | 0.035 (2) | −0.041 (2) | −0.0268 (19) |
Geometric parameters (Å, º) top
Ru1—Cl1 | 2.4325 (7) | C15—C16 | 1.371 (5) |
Ru1—S1 | 2.2087 (7) | C16—C17 | 1.389 (4) |
Ru1—N1 | 2.111 (2) | C17—C18 | 1.368 (4) |
Ru1—N3 | 1.997 (2) | C19—C20 | 1.428 (3) |
Ru1—N5 | 2.094 (2) | C20—C21 | 1.392 (4) |
Ru1—N6 | 2.027 (2) | C20—C25 | 1.406 (4) |
S1—O1 | 1.466 (2) | C21—C22 | 1.381 (4) |
S1—C27 | 1.795 (4) | C22—C23 | 1.384 (4) |
S1—C28 | 1.776 (4) | C23—C24 | 1.381 (4) |
N1—C1 | 1.352 (3) | C24—C25 | 1.382 (3) |
N1—C5 | 1.358 (3) | C25—C26 | 1.437 (4) |
N2—C5 | 1.381 (3) | C1—H1 | 0.9500 |
N2—C6 | 1.294 (3) | C2—H2 | 0.9500 |
N3—C6 | 1.365 (3) | C3—H3 | 0.9500 |
N3—C13 | 1.366 (3) | C4—H4 | 0.9500 |
N4—C13 | 1.298 (3) | C8—H8 | 0.9500 |
N4—C14 | 1.376 (3) | C9—H9 | 0.9500 |
N5—C14 | 1.353 (3) | C10—H10 | 0.9500 |
N5—C18 | 1.354 (3) | C11—H11 | 0.9500 |
N6—C19 | 1.143 (3) | C15—H15 | 0.9500 |
N7—C26 | 1.146 (4) | C16—H16 | 0.9500 |
C1—C2 | 1.370 (4) | C17—H17 | 0.9500 |
C2—C3 | 1.381 (4) | C18—H18 | 0.9500 |
C3—C4 | 1.372 (4) | C21—H21 | 0.9500 |
C4—C5 | 1.403 (3) | C22—H22 | 0.9500 |
C6—C7 | 1.475 (3) | C23—H23 | 0.9500 |
C7—C8 | 1.382 (4) | C24—H24 | 0.9500 |
C7—C12 | 1.387 (4) | C27—H27A | 0.9800 |
C8—C9 | 1.389 (4) | C27—H27B | 0.9800 |
C9—C10 | 1.391 (4) | C27—H27C | 0.9800 |
C10—C11 | 1.387 (4) | C28—H28A | 0.9800 |
C11—C12 | 1.376 (4) | C28—H28B | 0.9800 |
C12—C13 | 1.471 (3) | C28—H28C | 0.9800 |
C14—C15 | 1.410 (4) | | |
| | | |
Cl1—Ru1—S1 | 179.64 (3) | C15—C16—C17 | 118.0 (3) |
Cl1—Ru1—N1 | 91.54 (6) | C16—C17—C18 | 118.5 (3) |
Cl1—Ru1—N3 | 87.53 (6) | N5—C18—C17 | 124.7 (2) |
Cl1—Ru1—N5 | 87.57 (6) | N6—C19—C20 | 174.5 (3) |
Cl1—Ru1—N6 | 88.89 (6) | C19—C20—C21 | 118.8 (2) |
S1—Ru1—N1 | 88.12 (6) | C19—C20—C25 | 121.5 (2) |
S1—Ru1—N3 | 92.58 (6) | C21—C20—C25 | 119.7 (2) |
S1—Ru1—N5 | 92.78 (6) | C20—C21—C22 | 119.5 (2) |
S1—Ru1—N6 | 91.00 (6) | C21—C22—C23 | 120.6 (2) |
N1—Ru1—N3 | 88.50 (8) | C22—C23—C24 | 120.4 (2) |
N1—Ru1—N5 | 176.91 (8) | C23—C24—C25 | 119.8 (2) |
N1—Ru1—N6 | 90.40 (8) | C20—C25—C24 | 120.0 (2) |
N3—Ru1—N5 | 88.51 (8) | C20—C25—C26 | 119.7 (2) |
N3—Ru1—N6 | 176.22 (8) | C24—C25—C26 | 120.3 (2) |
N5—Ru1—N6 | 92.54 (8) | N7—C26—C25 | 179.6 (3) |
Ru1—S1—O1 | 117.21 (10) | N1—C1—H1 | 117.00 |
Ru1—S1—C27 | 113.05 (12) | C2—C1—H1 | 117.00 |
Ru1—S1—C28 | 113.41 (15) | C1—C2—H2 | 121.00 |
O1—S1—C27 | 105.50 (15) | C3—C2—H2 | 121.00 |
O1—S1—C28 | 106.27 (16) | C2—C3—H3 | 121.00 |
C27—S1—C28 | 99.7 (2) | C4—C3—H3 | 121.00 |
Ru1—N1—C1 | 119.39 (17) | C3—C4—H4 | 119.00 |
Ru1—N1—C5 | 124.31 (16) | C5—C4—H4 | 119.00 |
C1—N1—C5 | 116.3 (2) | C7—C8—H8 | 121.00 |
C5—N2—C6 | 124.8 (2) | C9—C8—H8 | 121.00 |
Ru1—N3—C6 | 125.07 (16) | C8—C9—H9 | 120.00 |
Ru1—N3—C13 | 125.24 (16) | C10—C9—H9 | 120.00 |
C6—N3—C13 | 109.4 (2) | C9—C10—H10 | 119.00 |
C13—N4—C14 | 124.7 (2) | C11—C10—H10 | 119.00 |
Ru1—N5—C14 | 124.17 (16) | C10—C11—H11 | 121.00 |
Ru1—N5—C18 | 118.68 (16) | C12—C11—H11 | 121.00 |
C14—N5—C18 | 117.0 (2) | C14—C15—H15 | 120.00 |
Ru1—N6—C19 | 175.4 (2) | C16—C15—H15 | 119.00 |
N1—C1—C2 | 125.2 (2) | C15—C16—H16 | 121.00 |
C1—C2—C3 | 118.4 (2) | C17—C16—H16 | 121.00 |
C2—C3—C4 | 118.1 (2) | C16—C17—H17 | 121.00 |
C3—C4—C5 | 121.0 (3) | C18—C17—H17 | 121.00 |
N1—C5—N2 | 125.7 (2) | N5—C18—H18 | 118.00 |
N1—C5—C4 | 121.0 (2) | C17—C18—H18 | 118.00 |
N2—C5—C4 | 113.3 (2) | C20—C21—H21 | 120.00 |
N2—C6—N3 | 130.5 (2) | C22—C21—H21 | 120.00 |
N2—C6—C7 | 121.0 (2) | C21—C22—H22 | 120.00 |
N3—C6—C7 | 108.6 (2) | C23—C22—H22 | 120.00 |
C6—C7—C8 | 132.1 (2) | C22—C23—H23 | 120.00 |
C6—C7—C12 | 106.6 (2) | C24—C23—H23 | 120.00 |
C8—C7—C12 | 121.3 (2) | C23—C24—H24 | 120.00 |
C7—C8—C9 | 117.6 (2) | C25—C24—H24 | 120.00 |
C8—C9—C10 | 120.7 (3) | S1—C27—H27A | 109.00 |
C9—C10—C11 | 121.5 (3) | S1—C27—H27B | 109.00 |
C10—C11—C12 | 117.3 (2) | S1—C27—H27C | 109.00 |
C7—C12—C11 | 121.6 (2) | H27A—C27—H27B | 110.00 |
C7—C12—C13 | 106.6 (2) | H27A—C27—H27C | 110.00 |
C11—C12—C13 | 131.8 (2) | H27B—C27—H27C | 109.00 |
N3—C13—N4 | 129.6 (2) | S1—C28—H28A | 109.00 |
N3—C13—C12 | 108.8 (2) | S1—C28—H28B | 109.00 |
N4—C13—C12 | 121.6 (2) | S1—C28—H28C | 109.00 |
N4—C14—N5 | 125.6 (2) | H28A—C28—H28B | 109.00 |
N4—C14—C15 | 113.8 (2) | H28A—C28—H28C | 109.00 |
N5—C14—C15 | 120.6 (2) | H28B—C28—H28C | 109.00 |
C14—C15—C16 | 120.9 (3) | | |
| | | |
N1—Ru1—S1—O1 | −45.14 (12) | C6—N3—C13—C12 | 1.2 (3) |
N1—Ru1—S1—C27 | 77.91 (15) | C13—N3—C6—C7 | −0.3 (3) |
N1—Ru1—S1—C28 | −169.60 (19) | C14—N4—C13—N3 | −10.0 (4) |
N3—Ru1—S1—O1 | −133.55 (12) | C14—N4—C13—C12 | 169.7 (2) |
N3—Ru1—S1—C27 | −10.51 (15) | C13—N4—C14—C15 | −178.8 (3) |
N3—Ru1—S1—C28 | 101.99 (19) | C13—N4—C14—N5 | −2.6 (4) |
N5—Ru1—S1—O1 | 137.82 (12) | C18—N5—C14—C15 | 6.7 (4) |
N5—Ru1—S1—C27 | −99.14 (15) | Ru1—N5—C18—C17 | 170.6 (2) |
N5—Ru1—S1—C28 | 13.36 (19) | C18—N5—C14—N4 | −169.3 (3) |
N6—Ru1—S1—O1 | 45.22 (12) | Ru1—N5—C14—C15 | −168.1 (2) |
N6—Ru1—S1—C27 | 168.27 (15) | Ru1—N5—C14—N4 | 15.9 (4) |
N6—Ru1—S1—C28 | −79.23 (19) | C14—N5—C18—C17 | −4.6 (4) |
Cl1—Ru1—N1—C1 | −101.52 (19) | N1—C1—C2—C3 | 1.2 (4) |
Cl1—Ru1—N1—C5 | 76.8 (2) | C1—C2—C3—C4 | 0.9 (4) |
S1—Ru1—N1—C1 | 78.36 (19) | C2—C3—C4—C5 | −0.5 (5) |
S1—Ru1—N1—C5 | −103.4 (2) | C3—C4—C5—N1 | −2.0 (4) |
N3—Ru1—N1—C1 | 171.0 (2) | C3—C4—C5—N2 | 176.4 (3) |
N3—Ru1—N1—C5 | −10.7 (2) | N2—C6—C7—C8 | 0.5 (4) |
N6—Ru1—N1—C1 | −12.6 (2) | N2—C6—C7—C12 | 179.1 (2) |
N6—Ru1—N1—C5 | 165.7 (2) | N3—C6—C7—C8 | −179.3 (3) |
Cl1—Ru1—N3—C6 | −81.77 (19) | N3—C6—C7—C12 | −0.7 (3) |
Cl1—Ru1—N3—C13 | 91.9 (2) | C8—C7—C12—C13 | −179.9 (2) |
S1—Ru1—N3—C6 | 97.88 (19) | C6—C7—C12—C11 | −176.2 (2) |
S1—Ru1—N3—C13 | −88.5 (2) | C6—C7—C8—C9 | 176.1 (3) |
N1—Ru1—N3—C6 | 9.8 (2) | C12—C7—C8—C9 | −2.3 (4) |
N1—Ru1—N3—C13 | −176.5 (2) | C6—C7—C12—C13 | 1.4 (3) |
N5—Ru1—N3—C6 | −169.4 (2) | C8—C7—C12—C11 | 2.6 (4) |
N5—Ru1—N3—C13 | 4.2 (2) | C7—C8—C9—C10 | 0.0 (4) |
Cl1—Ru1—N5—C14 | −101.8 (2) | C8—C9—C10—C11 | 2.1 (5) |
Cl1—Ru1—N5—C18 | 83.45 (19) | C9—C10—C11—C12 | −1.9 (5) |
S1—Ru1—N5—C14 | 78.4 (2) | C10—C11—C12—C13 | −177.3 (3) |
S1—Ru1—N5—C18 | −96.45 (19) | C10—C11—C12—C7 | −0.4 (4) |
N3—Ru1—N5—C14 | −14.2 (2) | C11—C12—C13—N4 | −4.2 (4) |
N3—Ru1—N5—C18 | 171.0 (2) | C7—C12—C13—N3 | −1.7 (3) |
N6—Ru1—N5—C14 | 169.5 (2) | C7—C12—C13—N4 | 178.6 (2) |
N6—Ru1—N5—C18 | −5.3 (2) | C11—C12—C13—N3 | 175.6 (3) |
C5—N1—C1—C2 | −3.5 (4) | N5—C14—C15—C16 | −4.1 (4) |
C1—N1—C5—N2 | −174.4 (2) | N4—C14—C15—C16 | 172.4 (3) |
Ru1—N1—C5—N2 | 7.3 (4) | C14—C15—C16—C17 | −1.2 (5) |
Ru1—N1—C5—C4 | −174.5 (2) | C15—C16—C17—C18 | 3.5 (5) |
Ru1—N1—C1—C2 | 174.9 (2) | C16—C17—C18—N5 | −0.6 (5) |
C1—N1—C5—C4 | 3.8 (4) | C19—C20—C25—C26 | −0.7 (4) |
C6—N2—C5—C4 | −176.8 (2) | C19—C20—C25—C24 | −178.0 (2) |
C5—N2—C6—N3 | −2.7 (4) | C19—C20—C21—C22 | 177.7 (2) |
C5—N2—C6—C7 | 177.5 (2) | C25—C20—C21—C22 | 0.6 (4) |
C6—N2—C5—N1 | 1.5 (4) | C21—C20—C25—C24 | −0.9 (4) |
Ru1—N3—C6—C7 | 174.17 (16) | C21—C20—C25—C26 | 176.3 (2) |
C13—N3—C6—N2 | 179.9 (3) | C20—C21—C22—C23 | 0.4 (4) |
Ru1—N3—C6—N2 | −5.6 (4) | C21—C22—C23—C24 | −1.1 (4) |
Ru1—N3—C13—N4 | 6.5 (4) | C22—C23—C24—C25 | 0.8 (4) |
Ru1—N3—C13—C12 | −173.27 (16) | C23—C24—C25—C20 | 0.2 (4) |
C6—N3—C13—N4 | −179.1 (3) | C23—C24—C25—C26 | −177.0 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O1i | 0.95 | 2.34 | 3.264 (3) | 165 |
C11—H11···O1ii | 0.95 | 2.59 | 3.241 (4) | 126 |
C23—H23···Cl1iii | 0.95 | 2.80 | 3.557 (3) | 137 |
Symmetry codes: (i) x+1/2, −y+1/2, z−1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, z+1/2. |