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In the monocationic octa­hedral complex, [RuCl(C6H18N4)(CO)]Cl, the ruthenium(II) centre is coordinated by a chloride and a carbonyl ligand and by the tetra­dentate tris­(2-amino­ethyl)amine (tren) chelator. The complex has approximate non-crystallographic Cs symmetry. In the crystal structure, N—H...Cl hydrogen bonds are found, mainly with the chloride counter-ion as the acceptor.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058874/hg2353sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058874/hg2353Isup2.hkl
Contains datablock I

CCDC reference: 672691

Key indicators

  • Single-crystal X-ray study
  • T = 200 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.020
  • wR factor = 0.048
  • Data-to-parameter ratio = 20.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ru - C1 .. 8.55 su
Author Response: situation checked, assignment of scattering sites correct
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H42    ...          ?
Author Response: situation checked, no suitable acceptor present

0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title compound, C7H18Cl2N4ORu, was obtained on the attempted preparation of [RuCl2(tren)] by refluxing RuCl3 with an equimolar amount of tris(2-aminoethyl)amine (tren) in DMF.

The molecular structure is shown in Fig. 1. The complex features three 5-membered rings: Ru–N1–C2–C3–N4 adopts a twist conformation on N1–C2 (Q2 = 0.444 (2) Å, ϕ2 = 241.5 (2)°), whereas Ru–N1–C5–C6–N7 (Q2 = 0.359 (2) Å, ϕ2 = 294.6 (3)°) shows an envelope conformation on C6. Ru–N1–C8–C9–N10 is twisted on N1–C8 (Q2 = 0.459 (2) Å, ϕ2 = 55.6 (2)°). Ring puckering parameters (Cremer & Pople, 1975) were calculated with PLATON (Spek, 2007).

Bond lengths and angles are normal.

The molecular packing including the hydrogen bond system is shown in Fig. 2. The search for hydrogen bonded molecular aggregates provided an infinite two-dimensional network (base vectors = [0 1 0], [2 0 1]) along the (1 0 - 2)-plane.

Related literature top

For related literature, see: Sullivan et al. (1978; Cremer & Pople (1975).

Experimental top

The title compound was obtained accidentally on the attempted preparation of [RuCl2(tren)] by refluxing RuCl3 * 3 H2O with an equimolar amount of tris(2-aminoethyl)amine (tren) and 7 equivalents of LiCl in DMF in analogy to a published procedure (Sullivan et al., 1978).

Refinement top

All H atoms were constructed and refined as riding on their parent atoms with one common isotropic displacement parameter.

Computing details top

Data collection: COLLECT (Hooft, 1997–2004); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level) for non-H atoms.
[Figure 2] Fig. 2. The packing of (I), viewed along [0 1 0].
Carbonylchlorido[tris(2-aminoethyl)amine]ruthenium(II) chloride top
Crystal data top
[RuCl(C6H18N4)(CO)]ClF(000) = 696
Mr = 346.22Dx = 1.840 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3049 reflections
a = 10.1514 (2) Åθ = 3.1–27.5°
b = 8.5268 (1) ŵ = 1.66 mm1
c = 14.7413 (3) ÅT = 200 K
β = 101.6790 (7)°Block, yellow
V = 1249.58 (4) Å30.17 × 0.12 × 0.07 mm
Z = 4
Data collection top
KappaCCD
diffractometer
2863 independent reflections
Radiation source: rotating anode2562 reflections with I > 2σ(I)
MONTEL, graded multilayered X-ray optics monochromatorRint = 0.031
ϕ and ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1313
Tmin = 0.800, Tmax = 0.890k = 1110
23413 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.048H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0181P)2 + 1.1292P]
where P = (Fo2 + 2Fc2)/3
2863 reflections(Δ/σ)max = 0.001
137 parametersΔρmax = 0.56 e Å3
0 restraintsΔρmin = 0.53 e Å3
Crystal data top
[RuCl(C6H18N4)(CO)]ClV = 1249.58 (4) Å3
Mr = 346.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.1514 (2) ŵ = 1.66 mm1
b = 8.5268 (1) ÅT = 200 K
c = 14.7413 (3) Å0.17 × 0.12 × 0.07 mm
β = 101.6790 (7)°
Data collection top
KappaCCD
diffractometer
2863 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
2562 reflections with I > 2σ(I)
Tmin = 0.800, Tmax = 0.890Rint = 0.031
23413 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0200 restraints
wR(F2) = 0.048H-atom parameters constrained
S = 1.06Δρmax = 0.56 e Å3
2863 reflectionsΔρmin = 0.53 e Å3
137 parameters
Special details top

Experimental. µ × r = 0.116, Tmin/Tmax = 0.899

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ru0.263803 (15)0.685462 (18)0.091163 (10)0.01895 (6)
Cl10.09940 (5)0.70362 (7)0.05312 (3)0.03170 (13)
O10.3830 (2)0.3964 (2)0.02630 (15)0.0593 (5)
N10.18612 (16)0.8875 (2)0.14884 (11)0.0220 (3)
N40.37625 (18)0.8578 (2)0.03603 (12)0.0285 (4)
H410.46670.84100.05770.0381 (16)*
H420.35930.84990.02750.0381 (16)*
N70.39797 (17)0.6894 (2)0.21966 (12)0.0247 (4)
H710.41620.58840.24030.0381 (16)*
H720.47750.73520.21300.0381 (16)*
N100.11750 (16)0.5702 (2)0.15115 (11)0.0240 (4)
H1010.06250.51100.10680.0381 (16)*
H1020.15950.50380.19720.0381 (16)*
C10.3369 (2)0.5085 (3)0.04993 (16)0.0343 (5)
C20.1995 (2)1.0192 (3)0.08523 (16)0.0310 (5)
H210.18451.12020.11470.0381 (16)*
H220.13101.00880.02730.0381 (16)*
C30.3396 (2)1.0170 (3)0.06317 (16)0.0329 (5)
H310.34281.09130.01200.0381 (16)*
H320.40601.05210.11820.0381 (16)*
C50.2655 (2)0.9209 (3)0.24410 (14)0.0300 (5)
H510.20380.95820.28360.0381 (16)*
H520.33081.00570.24050.0381 (16)*
C60.3403 (2)0.7782 (3)0.28834 (14)0.0307 (5)
H610.41330.81140.34000.0381 (16)*
H620.27790.71000.31410.0381 (16)*
C80.0435 (2)0.8471 (3)0.14896 (16)0.0299 (5)
H810.00930.84820.08470.0381 (16)*
H820.00470.92640.18510.0381 (16)*
C90.0346 (2)0.6870 (3)0.19081 (15)0.0292 (5)
H910.06680.69300.25880.0381 (16)*
H920.06040.65220.17850.0381 (16)*
Cl20.32744 (5)0.36408 (7)0.31352 (4)0.03583 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ru0.01829 (9)0.02010 (9)0.01801 (9)0.00241 (6)0.00263 (6)0.00132 (6)
Cl10.0317 (3)0.0424 (3)0.0181 (2)0.0134 (2)0.0020 (2)0.0007 (2)
O10.0670 (13)0.0386 (11)0.0765 (14)0.0085 (10)0.0243 (11)0.0213 (10)
N10.0230 (8)0.0200 (8)0.0226 (8)0.0004 (7)0.0039 (7)0.0014 (7)
N40.0253 (9)0.0384 (11)0.0225 (8)0.0102 (8)0.0060 (7)0.0013 (8)
N70.0212 (8)0.0261 (9)0.0247 (9)0.0008 (7)0.0001 (7)0.0038 (7)
N100.0228 (8)0.0243 (9)0.0233 (8)0.0079 (7)0.0007 (7)0.0025 (7)
C10.0345 (12)0.0319 (12)0.0371 (12)0.0037 (10)0.0082 (10)0.0065 (10)
C20.0319 (11)0.0236 (11)0.0352 (12)0.0013 (9)0.0017 (9)0.0087 (9)
C30.0351 (12)0.0275 (12)0.0348 (12)0.0104 (9)0.0045 (9)0.0082 (10)
C50.0385 (12)0.0267 (11)0.0239 (10)0.0036 (9)0.0041 (9)0.0065 (9)
C60.0337 (12)0.0374 (13)0.0180 (10)0.0053 (10)0.0020 (9)0.0018 (9)
C80.0207 (10)0.0337 (12)0.0364 (12)0.0040 (9)0.0089 (9)0.0010 (10)
C90.0234 (10)0.0375 (12)0.0282 (11)0.0055 (9)0.0087 (8)0.0010 (9)
Cl20.0257 (3)0.0361 (3)0.0443 (3)0.0040 (2)0.0038 (2)0.0146 (3)
Geometric parameters (Å, º) top
Ru—C11.838 (2)N10—H1010.9200
Ru—N72.0975 (17)N10—H1020.9200
Ru—N102.1176 (16)C2—C31.522 (3)
Ru—N42.1208 (17)C2—H210.9900
Ru—N12.1409 (17)C2—H220.9900
Ru—Cl12.4281 (5)C3—H310.9900
O1—C11.149 (3)C3—H320.9900
N1—C21.487 (3)C5—C61.510 (3)
N1—C81.489 (3)C5—H510.9900
N1—C51.498 (3)C5—H520.9900
N4—C31.484 (3)C6—H610.9900
N4—H410.9200C6—H620.9900
N4—H420.9200C8—C91.508 (3)
N7—C61.477 (3)C8—H810.9900
N7—H710.9200C8—H820.9900
N7—H720.9200C9—H910.9900
N10—C91.497 (3)C9—H920.9900
C1—Ru—N794.58 (9)H101—N10—H102108.1
C1—Ru—N1096.99 (8)O1—C1—Ru178.3 (2)
N7—Ru—N1090.72 (6)N1—C2—C3109.53 (17)
C1—Ru—N499.04 (9)N1—C2—H21109.8
N7—Ru—N491.91 (7)C3—C2—H21109.8
N10—Ru—N4163.50 (7)N1—C2—H22109.8
C1—Ru—N1175.95 (9)C3—C2—H22109.8
N7—Ru—N181.51 (6)H21—C2—H22108.2
N10—Ru—N182.04 (6)N4—C3—C2111.40 (17)
N4—Ru—N182.24 (7)N4—C3—H31109.3
C1—Ru—Cl190.85 (7)C2—C3—H31109.3
N7—Ru—Cl1174.57 (5)N4—C3—H32109.3
N10—Ru—Cl188.83 (5)C2—C3—H32109.3
N4—Ru—Cl187.02 (5)H31—C3—H32108.0
N1—Ru—Cl193.06 (5)N1—C5—C6112.32 (17)
C2—N1—C8112.88 (16)N1—C5—H51109.1
C2—N1—C5110.32 (16)C6—C5—H51109.1
C8—N1—C5112.42 (16)N1—C5—H52109.1
C2—N1—Ru105.61 (12)C6—C5—H52109.1
C8—N1—Ru104.53 (12)H51—C5—H52107.9
C5—N1—Ru110.72 (12)N7—C6—C5110.56 (17)
C3—N4—Ru110.29 (12)N7—C6—H61109.5
C3—N4—H41109.6C5—C6—H61109.5
Ru—N4—H41109.6N7—C6—H62109.5
C3—N4—H42109.6C5—C6—H62109.5
Ru—N4—H42109.6H61—C6—H62108.1
H41—N4—H42108.1N1—C8—C9110.39 (17)
C6—N7—Ru110.62 (12)N1—C8—H81109.6
C6—N7—H71109.5C9—C8—H81109.6
Ru—N7—H71109.5N1—C8—H82109.6
C6—N7—H72109.5C9—C8—H82109.6
Ru—N7—H72109.5H81—C8—H82108.1
H71—N7—H72108.1N10—C9—C8110.95 (16)
C9—N10—Ru110.59 (12)N10—C9—H91109.4
C9—N10—H101109.5C8—C9—H91109.4
Ru—N10—H101109.5N10—C9—H92109.4
C9—N10—H102109.5C8—C9—H92109.4
Ru—N10—H102109.5H91—C9—H92108.0
N7—Ru—N1—C2119.66 (13)C1—Ru—N10—C9178.62 (14)
N10—Ru—N1—C2148.41 (13)N7—Ru—N10—C986.67 (13)
N4—Ru—N1—C226.54 (12)N4—Ru—N10—C912.5 (3)
Cl1—Ru—N1—C260.03 (12)N1—Ru—N10—C95.35 (13)
N7—Ru—N1—C8121.04 (13)Cl1—Ru—N10—C987.91 (12)
N10—Ru—N1—C829.11 (12)C8—N1—C2—C3160.53 (18)
N4—Ru—N1—C8145.84 (13)C5—N1—C2—C372.8 (2)
Cl1—Ru—N1—C859.28 (12)Ru—N1—C2—C346.91 (19)
N7—Ru—N1—C50.25 (13)Ru—N4—C3—C223.8 (2)
N10—Ru—N1—C592.17 (13)N1—C2—C3—N448.3 (2)
N4—Ru—N1—C592.87 (13)C2—N1—C5—C6138.18 (19)
Cl1—Ru—N1—C5179.44 (12)C8—N1—C5—C694.9 (2)
C1—Ru—N4—C3177.75 (15)Ru—N1—C5—C621.6 (2)
N7—Ru—N4—C382.80 (14)Ru—N7—C6—C539.3 (2)
N10—Ru—N4—C316.2 (3)N1—C5—C6—N740.3 (2)
N1—Ru—N4—C31.64 (13)C2—N1—C8—C9163.23 (18)
Cl1—Ru—N4—C391.87 (13)C5—N1—C8—C971.2 (2)
C1—Ru—N7—C6157.49 (15)Ru—N1—C8—C948.95 (19)
N10—Ru—N7—C660.42 (14)Ru—N10—C9—C820.0 (2)
N4—Ru—N7—C6103.28 (14)N1—C8—C9—N1047.2 (2)
N1—Ru—N7—C621.42 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H41···Cl2i0.922.533.3569 (19)150
N7—H71···Cl20.922.463.2442 (18)144
N7—H72···Cl2i0.922.363.2830 (18)176
N10—H101···Cl1ii0.922.483.3319 (17)154
N10—H102···Cl20.922.473.3609 (18)164
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula[RuCl(C6H18N4)(CO)]Cl
Mr346.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)10.1514 (2), 8.5268 (1), 14.7413 (3)
β (°) 101.6790 (7)
V3)1249.58 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.66
Crystal size (mm)0.17 × 0.12 × 0.07
Data collection
DiffractometerKappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.800, 0.890
No. of measured, independent and
observed [I > 2σ(I)] reflections
23413, 2863, 2562
Rint0.031
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.020, 0.048, 1.06
No. of reflections2863
No. of parameters137
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.56, 0.53

Computer programs: COLLECT (Hooft, 1997–2004), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H41···Cl2i0.922.533.3569 (19)149.7
N7—H71···Cl20.922.463.2442 (18)143.9
N7—H72···Cl2i0.922.363.2830 (18)175.6
N10—H101···Cl1ii0.922.483.3319 (17)154.1
N10—H102···Cl20.922.473.3609 (18)164.2
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+1, z.
 

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