Serendipitous preparation of fac-(aceto­nitrile-κN)tri­chlorido­[(1,2,5,6-η)-cyclo­octa-1,5-diene]iridium(III)

An octa­hedral complex of iridium(III) with a chelating cyclo­octa-1,5-diene ligand, a facial arrangement of three chloride ligands and one aceto­nitrile ligand was isolated serendipitously from an attempted reaction between indene, the chlorido­cyclo­octa­dieneiridium dimer and HCl. Work-up that included use of aceto­nitrile solvent led to the formation of a few crystals of the title compound.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.019
• wR factor = 0.038
• Data-to-parameter ratio = 31.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Th(Min) ...          5 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT033_ALERT_4_G Flack x Value Deviates > 2*sigma from Zero .....     -0.011 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         85 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

fac-(Acetonitrile-κN)trichlorido[(1,2,5,6-η)-cycloocta-1,5-diene]iridium(III)

Crystal data

[IrCl3(C2H3N)(C8H12)]	Dx = 2.349 Mg m^−3
Mr = 447.78	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 12030 reflections
a = 8.25131 (10) Å	θ = 4.0–32.2°
b = 11.85605 (14) Å	µ = 11.15 mm^−1
c = 12.94150 (15) Å	T = 100 K
V = 1266.04 (3) Å^3	Prism, clear light orange
Z = 4	0.22 × 0.15 × 0.11 mm
F(000) = 840

Data collection

Agilent Xcalibur Eos Gemini ultra diffractometer	4333 independent reflections
Radiation source: Enhance (Mo) X-ray Source, Agilent Gemini System	4173 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 16.0122 pixels mm^-1	θmax = 32.4°, θmin = 3.4°
ω scans	h = −11→12
Absorption correction: analytical (SCALE3 ABSPACK; Clark & Reid, 1995)	k = −17→17
Tmin = 0.204, Tmax = 0.396	l = −19→19
27207 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.019	w = 1/[σ^2(Fo^2) + (0.0124P)^2 + 1.2315P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.038	(Δ/σ)max = 0.002
S = 1.08	Δρmax = 1.07 e Å^−3
4333 reflections	Δρmin = −0.74 e Å^−3
137 parameters	Absolute structure: Flack x determined using 1715 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.011 (4)
Primary atom site location: structure-invariant direct methods

Special details

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.

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

	x	y	z	Uiso*/Ueq
Ir1	0.70199 (2)	0.47821 (2)	0.68347 (2)	0.01178 (4)
Cl1	0.68059 (17)	0.64680 (9)	0.78048 (9)	0.0238 (2)
Cl2	0.85370 (14)	0.58778 (9)	0.56587 (9)	0.0202 (2)
Cl3	0.47576 (13)	0.52459 (13)	0.57940 (9)	0.0275 (2)
N1	0.5308 (5)	0.4220 (3)	0.7828 (3)	0.0153 (7)
C1	0.7775 (6)	0.3484 (4)	0.5677 (3)	0.0210 (9)
H1	0.7227	0.3540	0.5008	0.025*
C2	0.6888 (7)	0.2940 (4)	0.6442 (3)	0.0210 (9)
H2	0.5813	0.2686	0.6219	0.025*
C3	0.7669 (7)	0.2197 (4)	0.7247 (4)	0.0268 (12)
H3A	0.8639	0.1863	0.6953	0.032*
H3B	0.6930	0.1587	0.7413	0.032*
C4	0.8132 (6)	0.2806 (4)	0.8253 (4)	0.0245 (9)
H4A	0.7241	0.2736	0.8737	0.029*
H4B	0.9063	0.2430	0.8553	0.029*
C5	0.8528 (5)	0.4040 (4)	0.8121 (4)	0.0202 (9)
H5	0.8518	0.4477	0.8764	0.024*
C6	0.9554 (6)	0.4463 (4)	0.7360 (4)	0.0229 (10)
H6	1.0132	0.5148	0.7568	0.028*
C7	1.0494 (6)	0.3734 (5)	0.6606 (4)	0.0289 (12)
H7A	1.0816	0.3048	0.6959	0.035*
H7B	1.1476	0.4132	0.6414	0.035*
C8	0.9592 (6)	0.3407 (4)	0.5616 (4)	0.0254 (11)
H8A	0.9963	0.3892	0.5061	0.030*
H8B	0.9885	0.2640	0.5437	0.030*
C9	0.4307 (5)	0.3980 (4)	0.8376 (3)	0.0174 (9)
C10	0.3017 (7)	0.3700 (4)	0.9097 (3)	0.0246 (9)
H10A	0.2025	0.4047	0.8874	0.037*
H10B	0.3294	0.3972	0.9773	0.037*
H10C	0.2879	0.2896	0.9120	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.01257 (6)	0.01427 (6)	0.00849 (6)	0.00042 (6)	0.00024 (6)	0.00067 (6)
Cl1	0.0356 (7)	0.0166 (5)	0.0193 (5)	−0.0010 (5)	0.0073 (5)	−0.0029 (4)
Cl2	0.0229 (5)	0.0206 (5)	0.0170 (5)	−0.0021 (4)	0.0046 (4)	0.0034 (4)
Cl3	0.0177 (5)	0.0456 (7)	0.0191 (5)	0.0062 (5)	−0.0037 (4)	0.0099 (6)
N1	0.0216 (19)	0.0134 (17)	0.0110 (16)	−0.0012 (14)	−0.0036 (14)	0.0013 (13)
C1	0.027 (3)	0.022 (2)	0.014 (2)	−0.002 (2)	0.0019 (19)	−0.0038 (16)
C2	0.031 (2)	0.0162 (19)	0.0162 (19)	−0.006 (2)	0.002 (2)	−0.0054 (15)
C3	0.041 (3)	0.016 (2)	0.024 (2)	0.007 (2)	0.012 (2)	0.0051 (18)
C4	0.026 (2)	0.027 (2)	0.020 (2)	0.0060 (19)	−0.001 (2)	0.0097 (19)
C5	0.0196 (19)	0.028 (2)	0.0133 (19)	0.0018 (16)	−0.0060 (19)	0.006 (2)
C6	0.015 (2)	0.036 (3)	0.018 (2)	0.0004 (18)	−0.0079 (17)	0.0053 (19)
C7	0.016 (2)	0.040 (3)	0.030 (3)	0.010 (2)	0.0045 (19)	0.009 (2)
C8	0.030 (3)	0.024 (2)	0.022 (2)	0.008 (2)	0.011 (2)	−0.002 (2)
C9	0.0157 (19)	0.021 (2)	0.015 (2)	−0.0023 (16)	−0.0014 (15)	−0.0035 (16)
C10	0.020 (2)	0.037 (3)	0.017 (2)	−0.007 (2)	0.003 (2)	−0.0031 (18)

Geometric parameters (Å, º)

Ir1—Cl1	2.3670 (11)	C4—H4A	0.9700
Ir1—Cl2	2.3603 (11)	C4—H4B	0.9700
Ir1—Cl3	2.3666 (10)	C4—C5	1.509 (6)
Ir1—N1	2.023 (4)	C5—H5	0.9800
Ir1—C1	2.236 (4)	C5—C6	1.392 (7)
Ir1—C2	2.245 (4)	C6—H6	0.9800
Ir1—C5	2.257 (5)	C6—C7	1.517 (7)
Ir1—C6	2.231 (4)	C7—H7A	0.9700
N1—C9	1.125 (6)	C7—H7B	0.9700
C1—H1	0.9800	C7—C8	1.531 (8)
C1—C2	1.389 (6)	C8—H8A	0.9700
C1—C8	1.504 (7)	C8—H8B	0.9700
C2—H2	0.9800	C9—C10	1.454 (6)
C2—C3	1.510 (7)	C10—H10A	0.9600
C3—H3A	0.9700	C10—H10B	0.9600
C3—H3B	0.9700	C10—H10C	0.9600
C3—C4	1.537 (7)
Cl2—Ir1—Cl1	85.23 (4)	C2—C3—H3B	108.6
Cl2—Ir1—Cl3	85.61 (4)	C2—C3—C4	114.6 (4)
Cl3—Ir1—Cl1	92.68 (5)	H3A—C3—H3B	107.6
N1—Ir1—Cl1	83.63 (11)	C4—C3—H3A	108.6
N1—Ir1—Cl2	164.05 (11)	C4—C3—H3B	108.6
N1—Ir1—Cl3	83.55 (11)	C3—C4—H4A	108.6
N1—Ir1—C1	113.18 (16)	C3—C4—H4B	108.6
N1—Ir1—C2	77.86 (16)	H4A—C4—H4B	107.6
N1—Ir1—C5	77.73 (16)	C5—C4—C3	114.5 (4)
N1—Ir1—C6	113.88 (16)	C5—C4—H4A	108.6
C1—Ir1—Cl1	163.18 (12)	C5—C4—H4B	108.6
C1—Ir1—Cl2	78.41 (12)	Ir1—C5—H5	114.5
C1—Ir1—Cl3	89.92 (14)	C4—C5—Ir1	110.0 (3)
C1—Ir1—C2	36.12 (16)	C4—C5—H5	114.5
C1—Ir1—C5	94.14 (18)	C6—C5—Ir1	70.9 (3)
C2—Ir1—Cl1	159.73 (12)	C6—C5—C4	124.1 (5)
C2—Ir1—Cl2	114.52 (12)	C6—C5—H5	114.5
C2—Ir1—Cl3	93.37 (14)	Ir1—C6—H6	113.6
C2—Ir1—C5	79.33 (18)	C5—C6—Ir1	73.0 (3)
C5—Ir1—Cl1	88.79 (13)	C5—C6—H6	113.6
C5—Ir1—Cl2	113.44 (12)	C5—C6—C7	124.2 (5)
C5—Ir1—Cl3	160.95 (12)	C7—C6—Ir1	112.4 (3)
C6—Ir1—Cl1	92.97 (14)	C7—C6—H6	113.6
C6—Ir1—Cl2	78.03 (13)	C6—C7—H7A	108.4
C6—Ir1—Cl3	162.18 (12)	C6—C7—H7B	108.4
C6—Ir1—C1	79.97 (19)	C6—C7—C8	115.7 (4)
C6—Ir1—C2	87.1 (2)	H7A—C7—H7B	107.4
C6—Ir1—C5	36.15 (17)	C8—C7—H7A	108.4
C9—N1—Ir1	175.1 (4)	C8—C7—H7B	108.4
Ir1—C1—H1	114.7	C1—C8—C7	115.2 (4)
C2—C1—Ir1	72.3 (3)	C1—C8—H8A	108.5
C2—C1—H1	114.7	C1—C8—H8B	108.5
C2—C1—C8	122.3 (5)	C7—C8—H8A	108.5
C8—C1—Ir1	110.8 (3)	C7—C8—H8B	108.5
C8—C1—H1	114.7	H8A—C8—H8B	107.5
Ir1—C2—H2	114.2	N1—C9—C10	178.4 (5)
C1—C2—Ir1	71.6 (3)	C9—C10—H10A	109.5
C1—C2—H2	114.2	C9—C10—H10B	109.5
C1—C2—C3	122.5 (5)	C9—C10—H10C	109.5
C3—C2—Ir1	113.0 (3)	H10A—C10—H10B	109.5
C3—C2—H2	114.2	H10A—C10—H10C	109.5
C2—C3—H3A	108.6	H10B—C10—H10C	109.5
Ir1—C1—C2—C3	−106.1 (4)	C3—C4—C5—Ir1	32.7 (5)
Ir1—C1—C8—C7	27.6 (5)	C3—C4—C5—C6	−47.3 (6)
Ir1—C2—C3—C4	10.1 (6)	C4—C5—C6—Ir1	101.7 (4)
Ir1—C5—C6—C7	−105.8 (4)	C4—C5—C6—C7	−4.2 (7)
Ir1—C6—C7—C8	3.1 (6)	C5—C6—C7—C8	87.1 (6)
C1—C2—C3—C4	92.3 (5)	C6—C7—C8—C1	−20.8 (7)
C2—C1—C8—C7	−54.0 (6)	C8—C1—C2—Ir1	103.8 (4)
C2—C3—C4—C5	−29.0 (6)	C8—C1—C2—C3	−2.3 (7)