mer-Trichloro­(dimethyl sulfoxide-κS)-cis-bis­(1-methyl­imidazole-κN³)iridium(III)

The title compound, [IrCl₃(C₄H₆N₂)₂(C₂H₆OS)], has been synthesized and structurally characterized. The DMSO ligand is S-bonded and is trans to one and cis to the other 1-methyl­imidazole ligand. The two 1-methyl­imidazole ligands are cis to each other with an N...N...N...N pseudo-torsion angle between the planes of the two 1-methyl­imidazoles of 141.9 (5) °.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.023
• wR factor = 0.048
• Data-to-parameter ratio = 20.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .        100 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4

   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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: enCIFer (Allen et al., 2004).

mer-Trichloro(dimethyl sulfoxide-κS)-cis-bis(1-methylimidazole-κN³)iridium(III)

Crystal data

[IrCl3(C4H6N2)2(C2H6OS)]	F(000) = 2064
Mr = 540.92	Dx = 2.172 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 186 reflections
a = 30.741 (1) Å	θ = 3.9–23.7°
b = 8.614 (1) Å	µ = 8.68 mm^−1
c = 13.667 (1) Å	T = 183 K
β = 113.90 (1)°	Plate, colourless
V = 3308.7 (5) Å^3	0.46 × 0.11 × 0.04 mm
Z = 8

Data collection

Nonius KappaCCD diffractometer	3734 independent reflections
Radiation source: fine-focus sealed tube	3155 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
Detector resolution: 9 pixels mm^-1	θmax = 27.4°, θmin = 3.9°
φ? ω? scans	h = −39→39
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −10→11
Tmin = 0.109, Tmax = 0.701	l = −17→17
28714 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.048	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0127P)^2 + 12.7531P] where P = (Fo^2 + 2Fc^2)/3
3734 reflections	(Δ/σ)max = 0.003
185 parameters	Δρmax = 1.01 e Å^−3
0 restraints	Δρmin = −1.37 e Å^−3

Special details

Experimental. Preliminary examination and data collection were carried out on a Nonius KappaCCD device with an Oxford Cryosystems cooling system at the window of a sealed X-ray tube with graphite-monochromated Mo K_α radiation (λ = 0.71073 Å). The reflections were integrated. Raw data were corrected for Lorentz and polarization and, arising from the scaling procedure, for latent decay. An absorption correction was applied using SADABS (Sheldrick, 2003). After merging, all independent reflections were used to refine the structure. The structure was solved by a combination of direct methods and difference Fourier syntheses.

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·A multi-scan absorption correction was applied (absorption coefficient = 8.681 mm-1), and the maximum and minimum transmission factors were 0.1086 and 0.7013. Systematically absent reflections were not deleted and symmetry equivalent reflections were averaged to yield the set of unique data. No statistical outlier was deleted from the data set. The resulting 3734 data were used in the least squares refinement. The structure was solved using the SIR92 (Altomare et al., 1993) software package. Subsequent least-squares refinement and difference Fourier calculations revealed the positions of the remaining non-hydrogen atoms. At this point, a calculation by PLATON (Spek, 2005) showed that there was no missed crystallographic symmetry. Nonhydrogen atoms were refined with independent anisotropic displacement parameters. H atoms attached to C atoms were all positioned geometrically and treated as riding on their parent atoms, with aromatic C–H distances of 0.95 Å and methyl C–H distances of 0.98 Å. The U_iso(H) values were set to 1.2 U_eq(C) for all C-bound H atoms. An isotropic extinction parameter (see the SHELX97 manual for the definition of the EXTI command) was not needed. The weighting parameters (see the SHELX97 manual for the definition of the WGHT command) were 0.0127 and 12.7531. Successful convergence was indicated by the maximum shift/error of 0.001 for the last cycle of least squares refinement. The largest peak in the final Fourier difference map (1.01 e Å-3) was located 1.40 Å from the Ir1 atom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C4	0.50944 (18)	0.6522 (6)	0.1195 (4)	0.0413 (12)
H4A	0.5323	0.5668	0.1346	0.062*
H4B	0.5199	0.7239	0.1804	0.062*
H4C	0.5075	0.7077	0.0553	0.062*
N2	0.40711 (12)	0.4217 (4)	0.0848 (2)	0.0188 (7)
C1	0.45315 (15)	0.4394 (5)	0.1099 (3)	0.0231 (8)
H1A	0.4760	0.3581	0.1303	0.028*
C14	0.24277 (18)	0.1709 (8)	−0.3442 (4)	0.0511 (16)
H14A	0.2217	0.1172	−0.3174	0.077*
H14B	0.2515	0.1001	−0.3894	0.077*
H14C	0.2263	0.2616	−0.3862	0.077*
Cl1	0.43593 (3)	0.08725 (11)	0.05357 (8)	0.02103 (19)
Ir1	0.372381 (5)	0.215242 (17)	0.075814 (11)	0.01573 (5)
N4	0.33961 (12)	0.2436 (4)	−0.0887 (3)	0.0217 (7)
N3	0.28614 (14)	0.2218 (5)	−0.2531 (3)	0.0321 (9)
N1	0.46257 (14)	0.5897 (4)	0.1020 (3)	0.0270 (8)
C11	0.29683 (16)	0.1899 (6)	−0.1494 (3)	0.0292 (10)
H11A	0.2766	0.1364	−0.1237	0.035*
C3	0.42122 (18)	0.6727 (5)	0.0716 (4)	0.0312 (10)
H3A	0.4176	0.7816	0.0606	0.037*
C12	0.35665 (18)	0.3141 (5)	−0.1557 (4)	0.0320 (10)
H12A	0.3867	0.3637	−0.1344	0.038*
C2	0.38620 (16)	0.5680 (5)	0.0601 (3)	0.0260 (9)
H2A	0.3534	0.5908	0.0391	0.031*
S1	0.40564 (4)	0.18433 (12)	0.25441 (7)	0.0205 (2)
Cl2	0.33284 (4)	−0.02596 (12)	0.05722 (8)	0.0249 (2)
O1	0.43795 (12)	0.3075 (4)	0.3185 (2)	0.0340 (8)
C20	0.36144 (16)	0.1529 (6)	0.3045 (3)	0.0328 (10)
H20A	0.3763	0.1116	0.3775	0.049*
H20B	0.3380	0.0783	0.2586	0.049*
H20C	0.3456	0.2513	0.3052	0.049*
C13	0.32358 (19)	0.3015 (6)	−0.2577 (4)	0.0394 (12)
H13A	0.3260	0.3406	−0.3203	0.047*
Cl3	0.30776 (4)	0.34714 (13)	0.08643 (8)	0.0287 (2)
C21	0.43630 (16)	0.0059 (5)	0.2903 (3)	0.0282 (9)
H21A	0.4474	−0.0098	0.3677	0.042*
H21B	0.4637	0.0074	0.2708	0.042*
H21C	0.4149	−0.0790	0.2524	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C4	0.043 (3)	0.027 (3)	0.059 (3)	−0.017 (2)	0.026 (3)	−0.001 (2)
N2	0.0237 (17)	0.0146 (16)	0.0200 (16)	0.0013 (14)	0.0111 (14)	0.0009 (13)
C1	0.029 (2)	0.017 (2)	0.025 (2)	−0.0039 (17)	0.0131 (18)	−0.0009 (16)
C14	0.035 (3)	0.087 (5)	0.025 (2)	0.015 (3)	0.005 (2)	−0.004 (3)
Cl1	0.0247 (5)	0.0163 (5)	0.0266 (5)	0.0015 (4)	0.0150 (4)	−0.0014 (4)
Ir1	0.01822 (7)	0.01462 (8)	0.01656 (7)	−0.00017 (6)	0.00931 (5)	0.00026 (6)
N4	0.0241 (17)	0.0236 (19)	0.0175 (16)	0.0045 (14)	0.0084 (14)	0.0045 (13)
N3	0.031 (2)	0.045 (2)	0.0183 (17)	0.0138 (19)	0.0082 (15)	0.0043 (17)
N1	0.037 (2)	0.0175 (18)	0.0301 (19)	−0.0054 (16)	0.0173 (17)	0.0002 (15)
C11	0.027 (2)	0.039 (3)	0.023 (2)	0.0065 (19)	0.0113 (18)	0.0035 (18)
C3	0.048 (3)	0.016 (2)	0.031 (2)	0.0007 (19)	0.017 (2)	−0.0003 (17)
C12	0.043 (3)	0.031 (3)	0.031 (2)	−0.004 (2)	0.024 (2)	−0.0006 (19)
C2	0.032 (2)	0.016 (2)	0.032 (2)	0.0079 (18)	0.0162 (19)	0.0028 (17)
S1	0.0223 (5)	0.0226 (5)	0.0173 (4)	−0.0016 (4)	0.0088 (4)	−0.0007 (4)
Cl2	0.0273 (5)	0.0224 (5)	0.0248 (5)	−0.0076 (4)	0.0105 (4)	−0.0006 (4)
O1	0.0391 (19)	0.0309 (19)	0.0266 (16)	−0.0108 (14)	0.0077 (14)	−0.0078 (13)
C20	0.030 (2)	0.050 (3)	0.026 (2)	0.002 (2)	0.0188 (19)	0.004 (2)
C13	0.056 (3)	0.042 (3)	0.028 (2)	0.005 (2)	0.025 (2)	0.008 (2)
Cl3	0.0241 (5)	0.0327 (6)	0.0331 (5)	0.0054 (4)	0.0156 (4)	−0.0009 (5)
C21	0.035 (2)	0.027 (2)	0.024 (2)	0.0061 (19)	0.0138 (19)	0.0068 (18)

Geometric parameters (Å, º)

C4—N1	1.464 (6)	N3—C11	1.346 (5)
C4—H4A	0.9800	N3—C13	1.364 (6)
C4—H4B	0.9800	N1—C3	1.368 (6)
C4—H4C	0.9800	C11—H11A	0.9500
N2—C1	1.323 (5)	C3—C2	1.364 (6)
N2—C2	1.392 (5)	C3—H3A	0.9500
C1—N1	1.341 (5)	C12—C13	1.356 (7)
C1—H1A	0.9500	C12—H12A	0.9500
C14—N3	1.475 (6)	C2—H2A	0.9500
C14—H14A	0.9800	S1—O1	1.475 (3)
C14—H14B	0.9800	S1—C21	1.766 (4)
C14—H14C	0.9800	S1—C20	1.773 (4)
Ir1—Cl1	2.3676 (9)	C20—H20A	0.9800
Ir1—Cl2	2.3683 (10)	C20—H20B	0.9800
Ir1—Cl3	2.3434 (10)	C20—H20C	0.9800
Ir1—N2	2.052 (3)	C13—H13A	0.9500
Ir1—N4	2.072 (3)	C21—H21A	0.9800
Ir1—S1	2.2477 (9)	C21—H21B	0.9800
N4—C11	1.322 (6)	C21—H21C	0.9800
N4—C12	1.368 (5)
N1—C4—H4A	109.5	C13—N3—C14	127.0 (4)
N1—C4—H4B	109.5	C1—N1—C3	108.9 (4)
H4A—C4—H4B	109.5	C1—N1—C4	124.9 (4)
N1—C4—H4C	109.5	C3—N1—C4	126.1 (4)
H4A—C4—H4C	109.5	N4—C11—N3	110.2 (4)
H4B—C4—H4C	109.5	N4—C11—H11A	124.9
C1—N2—C2	107.4 (3)	N3—C11—H11A	124.9
C1—N2—Ir1	126.2 (3)	C2—C3—N1	106.4 (4)
C2—N2—Ir1	126.3 (3)	C2—C3—H3A	126.8
N2—C1—N1	109.5 (4)	N1—C3—H3A	126.8
N2—C1—H1A	125.3	C13—C12—N4	108.8 (4)
N1—C1—H1A	125.3	C13—C12—H12A	125.6
N3—C14—H14A	109.5	N4—C12—H12A	125.6
N3—C14—H14B	109.5	C3—C2—N2	107.8 (4)
H14A—C14—H14B	109.5	C3—C2—H2A	126.1
N3—C14—H14C	109.5	N2—C2—H2A	126.1
H14A—C14—H14C	109.5	O1—S1—C21	107.8 (2)
H14B—C14—H14C	109.5	O1—S1—C20	108.5 (2)
N2—Ir1—N4	88.59 (13)	C21—S1—C20	99.6 (2)
N2—Ir1—S1	92.33 (9)	O1—S1—Ir1	117.40 (14)
N4—Ir1—S1	178.18 (10)	C21—S1—Ir1	111.21 (15)
N2—Ir1—Cl1	88.57 (9)	C20—S1—Ir1	110.80 (15)
N4—Ir1—Cl1	88.83 (9)	S1—C20—H20A	109.5
N2—Ir1—Cl2	177.05 (9)	S1—C20—H20B	109.5
N4—Ir1—Cl2	89.10 (10)	H20A—C20—H20B	109.5
N2—Ir1—Cl3	90.54 (9)	S1—C20—H20C	109.5
N4—Ir1—Cl3	87.60 (10)	H20A—C20—H20C	109.5
S1—Ir1—Cl3	90.81 (4)	H20B—C20—H20C	109.5
S1—Ir1—Cl1	92.77 (3)	C12—C13—N3	106.7 (4)
S1—Ir1—Cl2	90.03 (3)	C12—C13—H13A	126.6
Cl3—Ir1—Cl1	176.34 (3)	N3—C13—H13A	126.6
Cl1—Ir1—Cl2	89.54 (3)	S1—C21—H21A	109.5
Cl3—Ir1—Cl2	91.20 (4)	S1—C21—H21B	109.5
C11—N4—C12	106.7 (4)	H21A—C21—H21B	109.5
C11—N4—Ir1	124.2 (3)	S1—C21—H21C	109.5
C12—N4—Ir1	129.0 (3)	H21A—C21—H21C	109.5
C11—N3—C13	107.5 (4)	H21B—C21—H21C	109.5
C11—N3—C14	125.4 (4)
C2—N2—C1—N1	−0.2 (4)	C1—N1—C3—C2	−0.6 (5)
Ir1—N2—C1—N1	176.6 (2)	C4—N1—C3—C2	177.3 (4)
C1—N2—Ir1—N4	−110.4 (3)	C11—N4—C12—C13	−0.2 (5)
C2—N2—Ir1—N4	65.9 (3)	Ir1—N4—C12—C13	178.2 (3)
C1—N2—Ir1—S1	71.2 (3)	N1—C3—C2—N2	0.5 (5)
C2—N2—Ir1—S1	−112.5 (3)	C1—N2—C2—C3	−0.2 (5)
C1—N2—Ir1—Cl3	162.1 (3)	Ir1—N2—C2—C3	−177.0 (3)
C2—N2—Ir1—Cl3	−21.7 (3)	N2—Ir1—S1—O1	1.11 (19)
C1—N2—Ir1—Cl1	−21.5 (3)	Cl3—Ir1—S1—O1	−89.46 (17)
N2—Ir1—N4—C11	−150.0 (4)	Cl1—Ir1—S1—O1	89.80 (16)
Cl3—Ir1—N4—C11	−59.4 (3)	Cl2—Ir1—S1—O1	179.34 (17)
Cl1—Ir1—N4—C11	121.4 (3)	N2—Ir1—S1—C21	−123.70 (19)
Cl2—Ir1—N4—C11	31.8 (3)	Cl3—Ir1—S1—C21	145.72 (17)
N2—Ir1—N4—C12	31.9 (4)	Cl1—Ir1—S1—C21	−35.02 (17)
Cl3—Ir1—N4—C12	122.5 (4)	Cl2—Ir1—S1—C21	54.52 (17)
Cl1—Ir1—N4—C12	−56.7 (4)	N2—Ir1—S1—C20	126.5 (2)
Cl2—Ir1—N4—C12	−146.3 (4)	Cl3—Ir1—S1—C20	35.97 (19)
N2—C1—N1—C3	0.5 (5)	Cl1—Ir1—S1—C20	−144.77 (19)
N2—C1—N1—C4	−177.5 (4)	Cl2—Ir1—S1—C20	−55.23 (19)
C12—N4—C11—N3	0.7 (5)	N4—C12—C13—N3	−0.4 (6)
Ir1—N4—C11—N3	−177.7 (3)	C11—N3—C13—C12	0.8 (6)
C13—N3—C11—N4	−1.0 (5)	C14—N3—C13—C12	−176.0 (5)
C14—N3—C11—N4	175.9 (4)