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The title compound [RuCl2(C33H44N3O)] is an example of a new generation of N,N-dialkyl metallocomplex ruthenium catalysts with an N→Ru coordination bond in a six-membered chelate ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023010381/tx2079sup1.cif
Contains datablocks I, shelx

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023010381/tx2079Isup2.hkl
Contains datablock I

CCDC reference: 2311600

Key indicators

Structure: I
  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.035
  • wR factor = 0.079
  • Data-to-parameter ratio = 23.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C NonSolvent Resd 1 C Ueq(max)/Ueq(min) Range 4.1 Ratio PLAT222_ALERT_3_C NonSolvent Resd 1 H Uiso(max)/Uiso(min) Range 5.1 Ratio PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 6 Note 1 1 0, -1 0 1, -1 1 1, 0 1 1, 1 0 1, 0 0 2, PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 5 Report 2 0 0, -7 10 1, -1 1 2, -1 0 3, -6 3 8,
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 21 Note PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 9 Report PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records 5 Report PLAT230_ALERT_2_G Hirshfeld Test Diff for C24 --C25 . 7.0 s.u. PLAT230_ALERT_2_G Hirshfeld Test Diff for C24 --C25A . 6.5 s.u. PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Ru1 --Cl1 . 6.7 s.u. PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) Ru1 --C2 . 5.2 s.u. PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 23% Note PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C14 Check PLAT398_ALERT_2_G Deviating C-O-C Angle From 120 for O1A . 133.5 Degree PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 1 Info PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 39 Note PLAT883_ALERT_1_G No Info/Value for _atom_sites_solution_primary . Please Do ! PLAT899_ALERT_4_G SHELXL2018 is Deprecated and Succeeded by SHELXL 2019/3 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 53 Note PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File 7 Note 0 0 2, 1 0 1, 0 1 1, -1 0 1, -1 1 2, -6 3 8, -7 10 1, PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 6 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 4 ALERT level C = Check. Ensure it is not caused by an omission or oversight 17 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 6 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

[1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene]dichlorido(2-{[(2-methoxyethyl)(methyl)amino]methyl}benzylidene)ruthenium top
Crystal data top
[RuCl2(C21H26N2)(C12H17NO)]F(000) = 1392
Mr = 669.67Dx = 1.412 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.6801 (13) ÅCell parameters from 9880 reflections
b = 10.7078 (11) Åθ = 2.4–29.8°
c = 22.035 (2) ŵ = 0.70 mm1
β = 102.553 (4)°T = 100 K
V = 3150.6 (5) Å3Bulk, dark green
Z = 40.40 × 0.36 × 0.24 mm
Data collection top
Bruker Kappa APEXII area-detector
diffractometer
7087 reflections with I > 2σ(I)
φ and ω scansRint = 0.049
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
θmax = 30.2°, θmin = 2.7°
Tmin = 0.679, Tmax = 0.746h = 1918
54060 measured reflectionsk = 1515
9279 independent reflectionsl = 3131
Refinement top
Refinement on F2460 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.023P)2 + 2.0327P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
9279 reflectionsΔρmax = 0.43 e Å3
493 parametersΔρmin = 0.58 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ru10.99437 (2)0.50148 (2)0.24032 (2)0.01454 (4)
Cl10.88778 (4)0.56961 (5)0.30419 (2)0.02505 (10)
Cl21.13328 (6)0.40424 (9)0.21357 (6)0.02561 (19)0.889 (2)
Cl2'1.1181 (6)0.3787 (9)0.2073 (5)0.02561 (19)0.111 (2)
N10.87352 (12)0.29680 (14)0.15568 (7)0.0189 (3)
N30.92109 (12)0.24251 (14)0.25209 (7)0.0195 (3)
C20.91734 (13)0.33997 (17)0.21276 (8)0.0166 (3)
C40.88154 (17)0.12448 (18)0.22184 (9)0.0287 (5)
H4A0.8265090.0912620.2398290.034*
H4B0.9348340.0606040.2255990.034*
C50.84371 (16)0.16398 (18)0.15466 (9)0.0252 (4)
H5A0.8759130.1147990.1263480.030*
H5B0.7701260.1545530.1417190.030*
C60.83979 (14)0.36710 (17)0.09962 (8)0.0194 (4)
C70.89679 (16)0.36545 (18)0.05392 (9)0.0240 (4)
C80.86167 (16)0.4348 (2)0.00026 (9)0.0279 (4)
H80.8993260.4352880.0317610.034*
C90.77363 (16)0.5029 (2)0.00927 (9)0.0273 (4)
C100.71724 (15)0.49803 (19)0.03628 (9)0.0252 (4)
H100.6555360.5420400.0297670.030*
C110.74867 (14)0.43064 (18)0.09096 (8)0.0212 (4)
C120.99271 (17)0.2928 (2)0.06261 (10)0.0341 (5)
H12A0.9774750.2036410.0564600.051*
H12B1.0324650.3063770.1047670.051*
H12C1.0308010.3208670.0322650.051*
C130.73922 (19)0.5826 (2)0.06635 (10)0.0393 (6)
H13A0.7528680.6706310.0555360.059*
H13B0.6671520.5709360.0822520.059*
H13C0.7752990.5580990.0983300.059*
C140.68862 (15)0.4321 (2)0.14068 (9)0.0269 (4)
H14A0.6273240.4808230.1262580.040*
H14B0.7284440.4700740.1785340.040*
H14C0.6709930.3463590.1496080.040*
C150.94359 (15)0.24718 (17)0.31907 (8)0.0207 (4)
C160.86644 (15)0.27982 (18)0.34872 (9)0.0236 (4)
C170.88825 (17)0.2812 (2)0.41338 (9)0.0308 (5)
H170.8377250.3062890.4343640.037*
C180.98179 (18)0.2470 (2)0.44827 (10)0.0347 (5)
C191.05376 (17)0.2080 (2)0.41729 (10)0.0332 (5)
H191.1168530.1809960.4408090.040*
C201.03692 (16)0.20690 (19)0.35252 (9)0.0265 (4)
C210.76253 (15)0.3087 (2)0.31286 (10)0.0292 (5)
H21A0.7286260.2309190.2969920.044*
H21B0.7661930.3638790.2779410.044*
H21C0.7249050.3501500.3402230.044*
C221.0032 (2)0.2503 (3)0.51858 (11)0.0548 (8)
H22A1.0331920.1708810.5351670.082*
H22B0.9405640.2635880.5323790.082*
H22C1.0497490.3187080.5337200.082*
C231.11778 (17)0.1615 (2)0.32081 (11)0.0373 (5)
H23A1.1062500.0733840.3095240.056*
H23B1.1833290.1707490.3491520.056*
H23C1.1162020.2110090.2831980.056*
N21.09671 (18)0.6647 (2)0.27615 (12)0.0244 (5)0.889 (2)
C241.14556 (18)0.7073 (2)0.22554 (12)0.0311 (6)0.889 (2)
H24A1.1807050.6355770.2115590.037*0.889 (2)
H24B1.1965070.7711950.2424780.037*0.889 (2)
C251.07400 (18)0.7610 (2)0.17056 (12)0.0290 (5)0.889 (2)
C261.1015 (2)0.8680 (2)0.14238 (14)0.0432 (7)0.889 (2)
H261.1636910.9068320.1596980.052*0.889 (2)
C271.0406 (3)0.9191 (3)0.08989 (17)0.0488 (8)0.889 (2)
H271.0612840.9919240.0714740.059*0.889 (2)
C280.9496 (3)0.8640 (3)0.06428 (15)0.0403 (8)0.889 (2)
H280.9076830.8983250.0280520.048*0.889 (2)
C290.9199 (2)0.7582 (3)0.09186 (13)0.0276 (6)0.889 (2)
H290.8573680.7206260.0739490.033*0.889 (2)
C300.9797 (4)0.7052 (3)0.14538 (14)0.0226 (6)0.889 (2)
C310.9409 (2)0.5948 (3)0.17136 (18)0.0178 (7)0.889 (2)
H310.8775110.5667810.1487490.021*0.889 (2)
C321.04729 (19)0.7748 (2)0.29788 (13)0.0299 (6)0.889 (2)
H32A1.0953730.8436830.3073090.045*0.889 (2)
H32B1.0237700.7524370.3354070.045*0.889 (2)
H32C0.9902110.8007370.2652270.045*0.889 (2)
C331.18122 (18)0.6234 (2)0.32777 (13)0.0321 (6)0.889 (2)
H33A1.2181490.6980510.3469980.039*0.889 (2)
H33B1.2281890.5718750.3100110.039*0.889 (2)
C341.1470 (2)0.5491 (3)0.37763 (13)0.0355 (6)0.889 (2)
H34A1.0863850.5872420.3875420.043*0.889 (2)
H34B1.1311070.4621510.3635920.043*0.889 (2)
O11.2275 (2)0.5512 (2)0.43055 (14)0.0521 (7)0.889 (2)
C351.2131 (3)0.4664 (4)0.47665 (16)0.0668 (11)0.889 (2)
H35A1.1471480.4803490.4860170.100*0.889 (2)
H35B1.2652160.4789920.5143980.100*0.889 (2)
H35C1.2169490.3807690.4616150.100*0.889 (2)
N2'1.1124 (14)0.6405 (16)0.2836 (8)0.027 (3)0.111 (2)
C24'1.0648 (15)0.7630 (16)0.2703 (7)0.028 (3)0.111 (2)
H24C1.1088070.8273100.2944280.034*0.111 (2)
H24D1.0009410.7631770.2844950.034*0.111 (2)
C25'1.0439 (14)0.7977 (14)0.2021 (7)0.029 (2)0.111 (2)
C26'1.0770 (16)0.9117 (16)0.1837 (8)0.037 (3)0.111 (2)
H26'1.1141950.9669220.2138160.044*0.111 (2)
C27'1.0559 (18)0.944 (2)0.1216 (9)0.039 (3)0.111 (2)
H27'1.0920081.0108710.1080940.047*0.111 (2)
C28'0.983 (2)0.883 (2)0.0789 (11)0.037 (2)0.111 (2)
H28'0.9528860.9211490.0405440.045*0.111 (2)
C29'0.9555 (19)0.762 (2)0.0934 (10)0.032 (3)0.111 (2)
H29'0.9132610.7115480.0630230.038*0.111 (2)
C30'0.992 (4)0.717 (3)0.1543 (11)0.025 (2)0.111 (2)
C31'0.958 (3)0.594 (3)0.1700 (16)0.0178 (7)0.111 (2)
H31'0.9096060.5562180.1380680.021*0.111 (2)
C32'1.2026 (13)0.6327 (17)0.2576 (10)0.034 (4)0.111 (2)
H32D1.2337560.5504960.2667940.052*0.111 (2)
H32E1.1840020.6447080.2124400.052*0.111 (2)
H32F1.2501840.6978110.2761450.052*0.111 (2)
C33'1.1427 (16)0.6235 (17)0.3521 (8)0.031 (2)0.111 (2)
H33C1.2048650.6720260.3671820.037*0.111 (2)
H33D1.0901340.6611970.3708470.037*0.111 (2)
C34'1.160 (2)0.4947 (19)0.3763 (11)0.038 (3)0.111 (2)
H34C1.0989000.4598730.3864680.046*0.111 (2)
H34D1.1813670.4399510.3452260.046*0.111 (2)
O1'1.2380 (19)0.5042 (18)0.4307 (11)0.040 (3)0.111 (2)
C35'1.253 (2)0.391 (2)0.4642 (12)0.053 (5)0.111 (2)
H35D1.3066120.4020330.5012240.080*0.111 (2)
H35E1.1908020.3680670.4768240.080*0.111 (2)
H35F1.2710990.3255970.4378490.080*0.111 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru10.01335 (7)0.01573 (7)0.01514 (7)0.00000 (6)0.00443 (5)0.00009 (6)
Cl10.0265 (2)0.0272 (2)0.0246 (2)0.00392 (19)0.01267 (19)0.00192 (19)
Cl20.0183 (4)0.0286 (5)0.0318 (4)0.0050 (3)0.0098 (3)0.0013 (3)
Cl2'0.0183 (4)0.0286 (5)0.0318 (4)0.0050 (3)0.0098 (3)0.0013 (3)
N10.0259 (8)0.0156 (7)0.0162 (8)0.0041 (6)0.0065 (6)0.0008 (6)
N30.0259 (9)0.0166 (8)0.0167 (8)0.0034 (6)0.0062 (6)0.0022 (6)
C20.0156 (8)0.0193 (9)0.0169 (9)0.0008 (7)0.0079 (7)0.0010 (7)
C40.0408 (13)0.0188 (10)0.0259 (11)0.0061 (9)0.0057 (9)0.0018 (8)
C50.0372 (12)0.0172 (9)0.0226 (10)0.0085 (8)0.0095 (8)0.0021 (7)
C60.0280 (10)0.0170 (9)0.0136 (8)0.0043 (7)0.0051 (7)0.0011 (7)
C70.0329 (11)0.0217 (10)0.0191 (10)0.0029 (8)0.0090 (8)0.0027 (7)
C80.0375 (12)0.0303 (11)0.0186 (10)0.0058 (9)0.0119 (8)0.0010 (8)
C90.0374 (11)0.0270 (10)0.0163 (9)0.0079 (10)0.0029 (8)0.0010 (8)
C100.0283 (10)0.0266 (10)0.0182 (9)0.0010 (9)0.0004 (7)0.0007 (8)
C110.0255 (10)0.0227 (10)0.0153 (9)0.0063 (8)0.0041 (7)0.0042 (7)
C120.0410 (13)0.0385 (13)0.0289 (11)0.0087 (10)0.0206 (10)0.0043 (9)
C130.0520 (15)0.0416 (14)0.0220 (11)0.0020 (11)0.0032 (10)0.0080 (10)
C140.0245 (10)0.0374 (12)0.0193 (10)0.0006 (9)0.0062 (8)0.0014 (8)
C150.0256 (10)0.0204 (9)0.0167 (9)0.0036 (8)0.0061 (7)0.0036 (7)
C160.0258 (10)0.0249 (10)0.0212 (10)0.0053 (8)0.0078 (8)0.0037 (8)
C170.0349 (12)0.0379 (12)0.0226 (10)0.0018 (10)0.0126 (9)0.0031 (9)
C180.0419 (13)0.0426 (13)0.0198 (10)0.0013 (11)0.0070 (9)0.0036 (9)
C190.0341 (12)0.0388 (13)0.0231 (11)0.0041 (10)0.0014 (9)0.0100 (9)
C200.0302 (11)0.0259 (10)0.0238 (10)0.0020 (8)0.0070 (8)0.0064 (8)
C210.0246 (11)0.0367 (12)0.0277 (11)0.0054 (9)0.0087 (8)0.0028 (9)
C220.0585 (18)0.084 (2)0.0208 (12)0.0085 (15)0.0064 (12)0.0079 (13)
C230.0353 (13)0.0426 (13)0.0358 (13)0.0141 (11)0.0114 (10)0.0124 (10)
N20.0206 (11)0.0230 (12)0.0281 (11)0.0029 (9)0.0018 (8)0.0048 (9)
C240.0252 (12)0.0284 (12)0.0416 (14)0.0114 (10)0.0113 (10)0.0011 (10)
C250.0327 (13)0.0228 (11)0.0363 (13)0.0056 (10)0.0178 (10)0.0006 (10)
C260.0494 (16)0.0289 (13)0.0576 (18)0.0106 (12)0.0256 (14)0.0059 (12)
C270.070 (2)0.0288 (15)0.058 (2)0.0015 (15)0.0365 (18)0.0157 (14)
C280.063 (2)0.0300 (15)0.0356 (17)0.0111 (14)0.0279 (14)0.0118 (13)
C290.0398 (16)0.0235 (11)0.0250 (12)0.0070 (12)0.0191 (12)0.0043 (9)
C300.0277 (19)0.0165 (12)0.0273 (14)0.0006 (10)0.0138 (12)0.0003 (11)
C310.0166 (17)0.0179 (9)0.0202 (9)0.0001 (10)0.0066 (11)0.0014 (7)
C320.0332 (14)0.0194 (11)0.0349 (14)0.0032 (10)0.0027 (11)0.0090 (10)
C330.0214 (12)0.0338 (13)0.0362 (14)0.0044 (10)0.0046 (10)0.0061 (11)
C340.0298 (14)0.0379 (16)0.0325 (14)0.0016 (13)0.0071 (11)0.0045 (13)
O10.0465 (14)0.0516 (17)0.0440 (12)0.0089 (14)0.0216 (10)0.0068 (14)
C350.067 (2)0.069 (3)0.048 (2)0.016 (2)0.0226 (18)0.0153 (18)
N2'0.025 (4)0.027 (4)0.031 (4)0.007 (4)0.008 (4)0.006 (4)
C24'0.028 (5)0.025 (5)0.032 (5)0.009 (4)0.009 (4)0.006 (5)
C25'0.034 (4)0.021 (4)0.037 (4)0.009 (4)0.015 (4)0.005 (4)
C26'0.045 (5)0.025 (5)0.044 (5)0.008 (5)0.017 (5)0.005 (5)
C27'0.053 (5)0.026 (4)0.045 (5)0.000 (4)0.025 (5)0.009 (4)
C28'0.051 (4)0.026 (4)0.040 (4)0.003 (4)0.025 (4)0.012 (4)
C29'0.041 (5)0.025 (4)0.034 (4)0.000 (5)0.017 (5)0.000 (4)
C30'0.030 (4)0.018 (4)0.028 (4)0.002 (4)0.010 (4)0.004 (4)
C31'0.0166 (17)0.0179 (9)0.0202 (9)0.0001 (10)0.0066 (11)0.0014 (7)
C32'0.028 (7)0.020 (7)0.054 (8)0.008 (6)0.005 (7)0.002 (7)
C33'0.027 (4)0.031 (4)0.030 (4)0.010 (4)0.006 (4)0.006 (4)
C34'0.035 (5)0.037 (5)0.035 (4)0.007 (5)0.008 (4)0.001 (5)
O1'0.034 (5)0.041 (6)0.036 (5)0.008 (5)0.014 (4)0.008 (5)
C35'0.048 (10)0.053 (10)0.045 (9)0.017 (9)0.018 (8)0.023 (9)
Geometric parameters (Å, º) top
Ru1—C31'1.81 (3)N2—C331.501 (3)
Ru1—C311.833 (4)C24—C251.497 (3)
Ru1—C22.0474 (18)C24—H24A0.9900
Ru1—N2'2.251 (15)C24—H24B0.9900
Ru1—N22.271 (2)C25—C261.393 (3)
Ru1—Cl22.3515 (8)C25—C301.421 (5)
Ru1—Cl12.3519 (5)C26—C271.383 (5)
Ru1—Cl2'2.379 (7)C26—H260.9500
N1—C21.352 (2)C27—C281.382 (5)
N1—C61.434 (2)C27—H270.9500
N1—C51.478 (2)C28—C291.388 (4)
N3—C21.350 (2)C28—H280.9500
N3—C151.441 (2)C29—C301.401 (4)
N3—C41.476 (2)C29—H290.9500
C4—C51.518 (3)C30—C311.462 (3)
C4—H4A0.9900C31—H310.9500
C4—H4B0.9900C32—H32A0.9800
C5—H5A0.9900C32—H32B0.9800
C5—H5B0.9900C32—H32C0.9800
C6—C111.396 (3)C33—C341.511 (4)
C6—C71.401 (3)C33—H33A0.9900
C7—C81.400 (3)C33—H33B0.9900
C7—C121.502 (3)C34—O11.420 (3)
C8—C91.384 (3)C34—H34A0.9900
C8—H80.9500C34—H34B0.9900
C9—C101.393 (3)O1—C351.408 (4)
C9—C131.508 (3)C35—H35A0.9800
C10—C111.390 (3)C35—H35B0.9800
C10—H100.9500C35—H35C0.9800
C11—C141.505 (3)N2'—C24'1.465 (17)
C12—H12A0.9800N2'—C32'1.472 (18)
C12—H12B0.9800N2'—C33'1.486 (16)
C12—H12C0.9800C24'—C25'1.514 (15)
C13—H13A0.9800C24'—H24C0.9900
C13—H13B0.9800C24'—H24D0.9900
C13—H13C0.9800C25'—C26'1.393 (15)
C14—H14A0.9800C25'—C30'1.423 (17)
C14—H14B0.9800C26'—C27'1.380 (17)
C14—H14C0.9800C26'—H26'0.9500
C15—C201.397 (3)C27'—C28'1.379 (18)
C15—C161.401 (3)C27'—H27'0.9500
C16—C171.391 (3)C28'—C29'1.407 (17)
C16—C211.501 (3)C28'—H28'0.9500
C17—C181.391 (3)C29'—C30'1.410 (16)
C17—H170.9500C29'—H29'0.9500
C18—C191.379 (3)C30'—C31'1.465 (17)
C18—C221.513 (3)C31'—H31'0.9500
C19—C201.396 (3)C32'—H32D0.9800
C19—H190.9500C32'—H32E0.9800
C20—C231.511 (3)C32'—H32F0.9800
C21—H21A0.9800C33'—C34'1.480 (16)
C21—H21B0.9800C33'—H33C0.9900
C21—H21C0.9800C33'—H33D0.9900
C22—H22A0.9800C34'—O1'1.421 (17)
C22—H22B0.9800C34'—H34C0.9900
C22—H22C0.9800C34'—H34D0.9900
C23—H23A0.9800O1'—C35'1.407 (17)
C23—H23B0.9800C35'—H35D0.9800
C23—H23C0.9800C35'—H35E0.9800
N2—C321.489 (3)C35'—H35F0.9800
N2—C241.491 (4)
C31'—Ru1—C2100.5 (8)C24—N2—C33105.1 (2)
C31—Ru1—C297.33 (11)C32—N2—Ru1115.62 (17)
C31'—Ru1—N2'92.1 (8)C24—N2—Ru1108.54 (16)
C2—Ru1—N2'163.8 (5)C33—N2—Ru1110.59 (15)
C31—Ru1—N288.48 (11)N2—C24—C25113.7 (2)
C2—Ru1—N2172.68 (8)N2—C24—H24A108.8
C31—Ru1—Cl2103.42 (13)C25—C24—H24A108.8
C2—Ru1—Cl286.77 (5)N2—C24—H24B108.8
N2—Ru1—Cl287.55 (7)C25—C24—H24B108.8
C31'—Ru1—Cl1104.7 (14)H24A—C24—H24B107.7
C31—Ru1—Cl198.02 (13)C26—C25—C30118.8 (3)
C2—Ru1—Cl195.36 (5)C26—C25—C24119.0 (2)
N2'—Ru1—Cl191.3 (6)C30—C25—C24122.2 (2)
N2—Ru1—Cl188.21 (7)C27—C26—C25121.8 (3)
Cl2—Ru1—Cl1158.02 (3)C27—C26—H26119.1
C31'—Ru1—Cl2'96.9 (15)C25—C26—H26119.1
C2—Ru1—Cl2'78.3 (2)C28—C27—C26119.8 (3)
N2'—Ru1—Cl2'90.2 (6)C28—C27—H27120.1
Cl1—Ru1—Cl2'158.4 (3)C26—C27—H27120.1
C2—N1—C6128.05 (15)C27—C28—C29119.6 (3)
C2—N1—C5114.09 (15)C27—C28—H28120.2
C6—N1—C5117.11 (15)C29—C28—H28120.2
C2—N3—C15126.88 (16)C28—C29—C30121.8 (3)
C2—N3—C4114.39 (15)C28—C29—H29119.1
C15—N3—C4117.90 (15)C30—C29—H29119.1
N3—C2—N1106.27 (15)C29—C30—C25118.2 (3)
N3—C2—Ru1121.14 (13)C29—C30—C31117.5 (3)
N1—C2—Ru1131.33 (13)C25—C30—C31124.3 (3)
N3—C4—C5102.46 (15)C30—C31—Ru1130.7 (2)
N3—C4—H4A111.3C30—C31—H31114.7
C5—C4—H4A111.3Ru1—C31—H31114.7
N3—C4—H4B111.3N2—C32—H32A109.5
C5—C4—H4B111.3N2—C32—H32B109.5
H4A—C4—H4B109.2H32A—C32—H32B109.5
N1—C5—C4102.64 (15)N2—C32—H32C109.5
N1—C5—H5A111.2H32A—C32—H32C109.5
C4—C5—H5A111.2H32B—C32—H32C109.5
N1—C5—H5B111.2N2—C33—C34113.4 (2)
C4—C5—H5B111.2N2—C33—H33A108.9
H5A—C5—H5B109.2C34—C33—H33A108.9
C11—C6—C7121.84 (17)N2—C33—H33B108.9
C11—C6—N1118.94 (16)C34—C33—H33B108.9
C7—C6—N1119.16 (17)H33A—C33—H33B107.7
C8—C7—C6117.70 (19)O1—C34—C33106.3 (2)
C8—C7—C12120.82 (18)O1—C34—H34A110.5
C6—C7—C12121.48 (18)C33—C34—H34A110.5
C9—C8—C7121.88 (19)O1—C34—H34B110.5
C9—C8—H8119.1C33—C34—H34B110.5
C7—C8—H8119.1H34A—C34—H34B108.7
C8—C9—C10118.54 (18)C35—O1—C34112.1 (3)
C8—C9—C13121.43 (19)O1—C35—H35A109.5
C10—C9—C13120.0 (2)O1—C35—H35B109.5
C11—C10—C9121.89 (19)H35A—C35—H35B109.5
C11—C10—H10119.1O1—C35—H35C109.5
C9—C10—H10119.1H35A—C35—H35C109.5
C10—C11—C6118.04 (18)H35B—C35—H35C109.5
C10—C11—C14120.70 (18)C24'—N2'—C32'110.3 (15)
C6—C11—C14121.18 (17)C24'—N2'—C33'109.1 (15)
C7—C12—H12A109.5C32'—N2'—C33'108.5 (15)
C7—C12—H12B109.5C24'—N2'—Ru1105.1 (11)
H12A—C12—H12B109.5C32'—N2'—Ru1112.5 (13)
C7—C12—H12C109.5C33'—N2'—Ru1111.4 (12)
H12A—C12—H12C109.5N2'—C24'—C25'113.5 (15)
H12B—C12—H12C109.5N2'—C24'—H24C108.9
C9—C13—H13A109.5C25'—C24'—H24C108.9
C9—C13—H13B109.5N2'—C24'—H24D108.9
H13A—C13—H13B109.5C25'—C24'—H24D108.9
C9—C13—H13C109.5H24C—C24'—H24D107.7
H13A—C13—H13C109.5C26'—C25'—C30'117.1 (15)
H13B—C13—H13C109.5C26'—C25'—C24'120.1 (14)
C11—C14—H14A109.5C30'—C25'—C24'122.8 (14)
C11—C14—H14B109.5C27'—C26'—C25'120.0 (16)
H14A—C14—H14B109.5C27'—C26'—H26'120.0
C11—C14—H14C109.5C25'—C26'—H26'120.0
H14A—C14—H14C109.5C28'—C27'—C26'121.3 (17)
H14B—C14—H14C109.5C28'—C27'—H27'119.3
C20—C15—C16121.73 (17)C26'—C27'—H27'119.3
C20—C15—N3119.80 (17)C27'—C28'—C29'118.4 (18)
C16—C15—N3118.11 (17)C27'—C28'—H28'120.8
C17—C16—C15117.70 (19)C29'—C28'—H28'120.8
C17—C16—C21120.32 (18)C28'—C29'—C30'118.0 (18)
C15—C16—C21121.95 (17)C28'—C29'—H29'121.0
C16—C17—C18122.0 (2)C30'—C29'—H29'121.0
C16—C17—H17119.0C29'—C30'—C25'121.1 (17)
C18—C17—H17119.0C29'—C30'—C31'117.7 (18)
C19—C18—C17118.4 (2)C25'—C30'—C31'120.1 (19)
C19—C18—C22120.9 (2)C30'—C31'—Ru1130.8 (19)
C17—C18—C22120.6 (2)C30'—C31'—H31'114.6
C18—C19—C20122.1 (2)Ru1—C31'—H31'114.6
C18—C19—H19118.9N2'—C32'—H32D109.5
C20—C19—H19118.9N2'—C32'—H32E109.5
C19—C20—C15117.78 (19)H32D—C32'—H32E109.5
C19—C20—C23120.05 (19)N2'—C32'—H32F109.5
C15—C20—C23122.17 (18)H32D—C32'—H32F109.5
C16—C21—H21A109.5H32E—C32'—H32F109.5
C16—C21—H21B109.5C34'—C33'—N2'117.9 (16)
H21A—C21—H21B109.5C34'—C33'—H33C107.8
C16—C21—H21C109.5N2'—C33'—H33C107.8
H21A—C21—H21C109.5C34'—C33'—H33D107.8
H21B—C21—H21C109.5N2'—C33'—H33D107.8
C18—C22—H22A109.5H33C—C33'—H33D107.2
C18—C22—H22B109.5O1'—C34'—C33'105.7 (15)
H22A—C22—H22B109.5O1'—C34'—H34C110.6
C18—C22—H22C109.5C33'—C34'—H34C110.6
H22A—C22—H22C109.5O1'—C34'—H34D110.6
H22B—C22—H22C109.5C33'—C34'—H34D110.6
C20—C23—H23A109.5H34C—C34'—H34D108.7
C20—C23—H23B109.5C35'—O1'—C34'112.1 (17)
H23A—C23—H23B109.5O1'—C35'—H35D109.5
C20—C23—H23C109.5O1'—C35'—H35E109.5
H23A—C23—H23C109.5H35D—C35'—H35E109.5
H23B—C23—H23C109.5O1'—C35'—H35F109.5
C32—N2—C24107.9 (2)H35D—C35'—H35F109.5
C32—N2—C33108.6 (2)H35E—C35'—H35F109.5
C15—N3—C2—N1167.34 (17)C33—N2—C24—C25176.1 (2)
C4—N3—C2—N11.9 (2)Ru1—N2—C24—C2565.6 (2)
C15—N3—C2—Ru124.1 (2)N2—C24—C25—C26138.3 (2)
C4—N3—C2—Ru1166.63 (14)N2—C24—C25—C3042.9 (4)
C6—N1—C2—N3170.61 (17)C30—C25—C26—C271.6 (5)
C5—N1—C2—N30.9 (2)C24—C25—C26—C27177.2 (3)
C6—N1—C2—Ru122.5 (3)C25—C26—C27—C280.3 (5)
C5—N1—C2—Ru1167.80 (14)C26—C27—C28—C290.5 (5)
C2—N3—C4—C53.7 (2)C27—C28—C29—C300.2 (5)
C15—N3—C4—C5166.58 (17)C28—C29—C30—C251.5 (6)
C2—N1—C5—C43.1 (2)C28—C29—C30—C31179.1 (4)
C6—N1—C5—C4174.01 (16)C26—C25—C30—C292.2 (6)
N3—C4—C5—N13.7 (2)C24—C25—C30—C29176.6 (3)
C2—N1—C6—C1178.7 (2)C26—C25—C30—C31178.5 (4)
C5—N1—C6—C1190.8 (2)C24—C25—C30—C312.8 (7)
C2—N1—C6—C7104.2 (2)C29—C30—C31—Ru1178.9 (3)
C5—N1—C6—C786.3 (2)C25—C30—C31—Ru11.7 (8)
C11—C6—C7—C82.9 (3)C2—Ru1—C31—C30156.7 (4)
N1—C6—C7—C8179.88 (17)N2—Ru1—C31—C3018.9 (5)
C11—C6—C7—C12177.59 (19)Cl2—Ru1—C31—C3068.3 (5)
N1—C6—C7—C120.6 (3)Cl1—Ru1—C31—C30106.8 (4)
C6—C7—C8—C90.3 (3)C32—N2—C33—C3478.3 (3)
C12—C7—C8—C9179.8 (2)C24—N2—C33—C34166.5 (2)
C7—C8—C9—C102.2 (3)Ru1—N2—C33—C3449.6 (3)
C7—C8—C9—C13176.8 (2)N2—C33—C34—O1162.1 (2)
C8—C9—C10—C112.2 (3)C33—C34—O1—C35169.0 (3)
C13—C9—C10—C11176.80 (19)C32'—N2'—C24'—C25'53 (2)
C9—C10—C11—C60.3 (3)C33'—N2'—C24'—C25'172.0 (16)
C9—C10—C11—C14177.06 (18)Ru1—N2'—C24'—C25'68.4 (17)
C7—C6—C11—C102.9 (3)N2'—C24'—C25'—C26'128 (2)
N1—C6—C11—C10179.88 (16)N2'—C24'—C25'—C30'51 (4)
C7—C6—C11—C14179.65 (18)C30'—C25'—C26'—C27'2 (4)
N1—C6—C11—C143.3 (3)C24'—C25'—C26'—C27'178 (2)
C2—N3—C15—C20105.2 (2)C25'—C26'—C27'—C28'16 (4)
C4—N3—C15—C2085.9 (2)C26'—C27'—C28'—C29'22 (5)
C2—N3—C15—C1681.5 (2)C27'—C28'—C29'—C30'9 (5)
C4—N3—C15—C1687.4 (2)C28'—C29'—C30'—C25'9 (7)
C20—C15—C16—C175.4 (3)C28'—C29'—C30'—C31'177 (4)
N3—C15—C16—C17178.51 (18)C26'—C25'—C30'—C29'15 (6)
C20—C15—C16—C21172.71 (19)C24'—C25'—C30'—C29'166 (3)
N3—C15—C16—C210.4 (3)C26'—C25'—C30'—C31'178 (4)
C15—C16—C17—C182.5 (3)C24'—C25'—C30'—C31'1 (7)
C21—C16—C17—C18175.7 (2)C29'—C30'—C31'—Ru1175 (3)
C16—C17—C18—C191.5 (3)C25'—C30'—C31'—Ru116 (8)
C16—C17—C18—C22179.6 (2)C2—Ru1—C31'—C30'174 (5)
C17—C18—C19—C202.7 (4)N2'—Ru1—C31'—C30'5 (5)
C22—C18—C19—C20178.4 (2)Cl1—Ru1—C31'—C30'87 (5)
C18—C19—C20—C150.1 (3)Cl2'—Ru1—C31'—C30'95 (5)
C18—C19—C20—C23179.1 (2)C24'—N2'—C33'—C34'160 (2)
C16—C15—C20—C194.2 (3)C32'—N2'—C33'—C34'80 (2)
N3—C15—C20—C19177.24 (18)Ru1—N2'—C33'—C34'44 (2)
C16—C15—C20—C23174.9 (2)N2'—C33'—C34'—O1'147 (2)
N3—C15—C20—C231.9 (3)C33'—C34'—O1'—C35'171 (3)
C32—N2—C24—C2560.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···Cl1i0.992.893.651 (2)134
C5—H5B···Cl1i0.992.833.622 (2)137
C24—H24A···Cl20.992.563.257 (3)127
C24—H24B···Cl2ii0.992.723.693 (3)167
C33—H33B···Cl20.992.873.399 (3)114
C34—H34A···Cl10.992.943.570 (3)123
C24—H24D···Cl10.992.683.391 (19)129
C32—H32D···Cl20.982.593.07 (2)110
C32—H32F···Cl2ii0.982.623.57 (2)164
C4—H4A···Cl1i0.992.893.651 (2)134
C5—H5B···Cl1i0.992.833.622 (2)137
C24—H24A···Cl20.992.563.257 (3)127
C24—H24B···Cl2ii0.992.723.693 (3)167
C33—H33B···Cl20.992.873.399 (3)114
C34—H34A···Cl10.992.943.570 (3)123
C24—H24D···Cl10.992.683.391 (19)129
C32—H32D···Cl20.982.593.07 (2)110
C32—H32F···Cl2ii0.982.623.57 (2)164
C34—H34C···Cg30.992.963.83 (2)149
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+5/2, y+1/2, z+1/2.
Summary of short interatomic contacts (Å) in the title compound top
ContactDistanceSymmetry operation
H14B···H4A2.463/2 - x, 1/2 + y, 1/2 - z
*H34D···*H262.175/2 - x, -1/2 + y, 1/2 - z
*H29'···H12C2.412 - x, 1 - y, -z
C9···H192.94-1/2 + x, 1/2 - y, -1/2 + z
*H28···*H35B2.32-1/2 + x, 3/2 - y, -1/2 + z
*H26'···H23A2.42x, 1 + y, z
*H33···H22B2.402 - x, 1 - y, 1 - z
 

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