cis-(2-Acetyl­cyclo­penta­nonato-κ²O,O′)bis­(2-pyridylphen­yl-κN)iridium(III) dichloro­methane solvate

The title compound, [Ir(C₁₁H₈N)₂(C₇H₉O₂)]·CH₂Cl₂ or [Ir(ppy)₂(2-acetyl­cyclo­penta­none)] (ppy = 2-phenyl­pyridine), is a neutral mononuclear iridium(III) complex. The complex and solvent mol­ecules both lie on twofold rotation axes. The iridium centre is coordinated by two N atoms and two C atoms from two ppy ligands [Ir—N = 2.044 (3) Å and Ir—C = 1.992 (4) Å], and two O atoms from the β-diketonate ligand [Ir—O= 2.11 (2) and 2.21 (2) Å], forming a distorted octa­hedral environment. The structure is stabilized by aromatic π–π stacking and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.028
• wR factor = 0.067
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?

Author Response: Omitted 2 reflections because of OFF Center.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C14

Author Response: Explained in _publ_section_exptl_refinement

PLAT301_ALERT_3_C Main Residue  Disorder .........................      21.00 Perc.

Author Response: Explained in _publ_section_exptl_refinement

Alert level G
ABSTM02_ALERT_3_G  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.431     0.533
            Tmin and Tmax expected:      0.229     0.360
            RR =      1.271
            Please check that your absorption correction is appropriate.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: STADI4 (Stoe & Cie, 1996); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97-2 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97-2 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97-2.

cis-(2-Acetylcyclopentanonato-κ²O,O')bis(2-pyridyl-κN-phenyl)iridium(III) dichloromethane solvate

Crystal data

[Ir(C11H8N)2(C7H9O2)]·CH2Cl2	F(000) = 1392
Mr = 710.64	Dx = 1.727 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -c_2yc	Cell parameters from 32 reflections
a = 12.094 (1) Å	θ = 9.5–10.4°
b = 14.889 (2) Å	µ = 5.11 mm^−1
c = 15.287 (2) Å	T = 298 K
β = 96.743 (9)°	Block, yellow
V = 2733.7 (6) Å^3	0.50 × 0.25 × 0.20 mm
Z = 4

Data collection

Stoe Stadi-4 diffractometer	2873 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 2.2°
ω–2θ scans	h = −15→15
Absorption correction: numerical (X-SHAPE; Stoe & Cie, 1996)	k = 0→19
Tmin = 0.431, Tmax = 0.533	l = 0→19
3137 measured reflections	3 standard reflections every 60 min
3137 independent reflections	intensity decay: 3.2%

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.067	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0313P)^2 + 8.9226P] where P = (Fo^2 + 2Fc^2)/3
3137 reflections	(Δ/σ)max < 0.001
192 parameters	Δρmax = 0.70 e Å^−3
52 restraints	Δρmin = −0.53 e Å^−3

Special details

Experimental. Spectroscopic analysis: ¹H NMR (300 MHz, CDCl₃): δ 8.51 (d, 2H, J = 5.1), 7.85 (d, 2H, J = 7.8), 7.51 (t, 2H, J = 7.2), 7.54 (d, 2H, J = 7.5), 7.13 (t, 2H, J = 7.2), 6.80 (t, 2H, J = 7.2), 6.68 (t, 2H, J = 7.5), 6.26 (d, 2H, J = 7.8), 2.17(s, 3H), 1.78 (s, 6H). HRMS (EI, m/z): Calcd for C₂₉H₂₅IrN₂O₂: 625.74. Found: 626.26.

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ir1	0.5000	0.041705 (14)	0.7500	0.03459 (8)
Cl1	0.0917 (2)	0.1471 (2)	0.8175 (2)	0.1550 (11)
N1	0.3730 (3)	0.0338 (2)	0.6496 (2)	0.0399 (7)
C1	0.2776 (4)	0.0809 (3)	0.6458 (3)	0.0517 (11)
H1	0.2687	0.1219	0.6904	0.062*
C2	0.1925 (5)	0.0704 (4)	0.5781 (4)	0.0620 (13)
H2	0.1272	0.1035	0.5772	0.074*
C3	0.2061 (5)	0.0103 (4)	0.5123 (4)	0.0606 (13)
H3	0.1500	0.0024	0.4658	0.073*
C4	0.3033 (4)	−0.0385 (3)	0.5153 (3)	0.0517 (11)
H4	0.3132	−0.0793	0.4708	0.062*
C5	0.3866 (4)	−0.0264 (3)	0.5852 (3)	0.0400 (9)
C6	0.4932 (4)	−0.0747 (3)	0.5984 (3)	0.0388 (9)
C7	0.5259 (4)	−0.1374 (3)	0.5388 (3)	0.0498 (11)
H7	0.4801	−0.1494	0.4869	0.060*
C8	0.6266 (5)	−0.1816 (3)	0.5568 (3)	0.0561 (12)
H8	0.6478	−0.2245	0.5178	0.067*
C9	0.6958 (4)	−0.1618 (3)	0.6332 (3)	0.0542 (12)
H9	0.7636	−0.1914	0.6454	0.065*
C10	0.6639 (4)	−0.0977 (3)	0.6916 (3)	0.0468 (10)
H10	0.7119	−0.0844	0.7421	0.056*
C11	0.5619 (4)	−0.0524 (3)	0.6769 (3)	0.0374 (8)
O1	0.5641 (19)	0.1484 (6)	0.6800 (15)	0.040 (3)	0.50
O2	0.4112 (19)	0.1432 (7)	0.8213 (15)	0.040 (3)	0.50
C12	0.5497 (12)	0.2314 (5)	0.6892 (9)	0.0456 (18)	0.50
C13	0.6028 (11)	0.3035 (7)	0.6398 (8)	0.058 (2)	0.50
H13A	0.6812	0.3098	0.6613	0.069*	0.50
H13B	0.5955	0.2904	0.5772	0.069*	0.50
C14	0.5404 (11)	0.3856 (6)	0.6576 (8)	0.088 (4)	0.50
H14A	0.4778	0.3941	0.6125	0.106*	0.50
H14B	0.5883	0.4379	0.6585	0.106*	0.50
C15	0.5011 (18)	0.3721 (4)	0.7447 (11)	0.079 (3)	0.50
H15A	0.4313	0.4034	0.7476	0.095*	0.50
H15B	0.5555	0.3947	0.7911	0.095*	0.50
C16	0.4856 (9)	0.2723 (4)	0.7546 (8)	0.053 (3)	0.50
C17	0.4264 (10)	0.2266 (6)	0.8103 (8)	0.0456 (18)	0.50
C18	0.3663 (10)	0.2824 (8)	0.8734 (8)	0.058 (2)	0.50
H18A	0.2928	0.2966	0.8461	0.087*	0.50
H18B	0.4069	0.3369	0.8874	0.087*	0.50
H18C	0.3612	0.2488	0.9264	0.087*	0.50
C19	0.0000	0.2116 (7)	0.7500	0.098 (3)
H19A	−0.0414	0.2499	0.7858	0.118*	0.50
H19B	0.0414	0.2499	0.7142	0.118*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.04410 (13)	0.03187 (11)	0.02759 (11)	0.000	0.00327 (8)	0.000
Cl1	0.130 (2)	0.174 (3)	0.165 (3)	0.044 (2)	0.0382 (19)	0.045 (2)
N1	0.0456 (18)	0.0395 (18)	0.0336 (16)	0.0014 (15)	0.0006 (14)	0.0038 (14)
C1	0.053 (3)	0.052 (3)	0.049 (3)	0.009 (2)	0.004 (2)	−0.002 (2)
C2	0.052 (3)	0.067 (3)	0.065 (3)	0.011 (2)	−0.003 (2)	0.001 (3)
C3	0.059 (3)	0.065 (3)	0.052 (3)	0.003 (3)	−0.015 (2)	0.001 (2)
C4	0.064 (3)	0.049 (2)	0.039 (2)	−0.001 (2)	−0.005 (2)	−0.0028 (19)
C5	0.053 (2)	0.035 (2)	0.0309 (19)	−0.0063 (17)	0.0011 (17)	0.0025 (15)
C6	0.050 (2)	0.0325 (18)	0.034 (2)	−0.0034 (17)	0.0070 (17)	0.0007 (16)
C7	0.067 (3)	0.047 (2)	0.036 (2)	−0.003 (2)	0.011 (2)	−0.0063 (19)
C8	0.072 (3)	0.047 (3)	0.054 (3)	0.006 (2)	0.023 (2)	−0.009 (2)
C9	0.055 (3)	0.054 (3)	0.056 (3)	0.014 (2)	0.014 (2)	0.001 (2)
C10	0.050 (2)	0.047 (2)	0.043 (2)	0.009 (2)	0.0042 (19)	0.0034 (19)
C11	0.048 (2)	0.034 (2)	0.0307 (18)	0.0020 (17)	0.0089 (16)	0.0043 (15)
O1	0.044 (8)	0.0399 (18)	0.0377 (16)	−0.001 (3)	0.006 (4)	0.002 (3)
O2	0.044 (8)	0.0399 (18)	0.0377 (16)	−0.001 (3)	0.006 (4)	0.002 (3)
C12	0.043 (5)	0.041 (2)	0.046 (2)	0.004 (3)	−0.020 (3)	−0.003 (5)
C13	0.065 (6)	0.036 (4)	0.072 (4)	0.008 (3)	0.006 (4)	0.003 (3)
C14	0.089 (7)	0.061 (6)	0.113 (8)	−0.005 (6)	0.007 (6)	0.027 (6)
C15	0.075 (5)	0.045 (4)	0.115 (7)	−0.003 (10)	−0.001 (5)	0.004 (9)
C16	0.047 (6)	0.043 (4)	0.065 (5)	−0.024 (4)	−0.006 (4)	−0.027 (5)
C17	0.043 (5)	0.041 (2)	0.046 (2)	0.004 (3)	−0.020 (3)	−0.003 (5)
C18	0.065 (6)	0.036 (4)	0.072 (4)	0.008 (3)	0.006 (4)	0.003 (3)
C19	0.123 (9)	0.066 (6)	0.119 (9)	0.000	0.065 (7)	0.000

Geometric parameters (Å, º)

Ir1—C11	1.992 (4)	C9—C10	1.394 (6)
Ir1—C11^i	1.992 (4)	C9—H9	0.9300
Ir1—N1	2.044 (3)	C10—C11	1.400 (6)
Ir1—N1^i	2.044 (3)	C10—H10	0.9300
Ir1—O1	2.11 (2)	O1—C12	1.258 (7)
Ir1—O1^i	2.11 (2)	O2—C17	1.269 (8)
Ir1—O2	2.21 (2)	C12—C16	1.468 (8)
Ir1—O2^i	2.21 (2)	C12—C13	1.500 (9)
Cl1—C19	1.717 (6)	C13—C14	1.478 (8)
N1—C1	1.345 (6)	C13—H13A	0.9700
N1—C5	1.355 (5)	C13—H13B	0.9700
C1—C2	1.380 (7)	C14—C15	1.479 (9)
C1—H1	0.9300	C14—H14A	0.9700
C2—C3	1.371 (8)	C14—H14B	0.9700
C2—H2	0.9300	C15—C16	1.507 (7)
C3—C4	1.377 (7)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.392 (6)	C16—C17	1.358 (8)
C4—H4	0.9300	C17—C18	1.521 (9)
C5—C6	1.470 (6)	C18—H18A	0.9600
C6—C7	1.393 (6)	C18—H18B	0.9600
C6—C11	1.417 (6)	C18—H18C	0.9600
C7—C8	1.384 (7)	C19—Cl1^ii	1.717 (6)
C7—H7	0.9300	C19—H19A	0.9700
C8—C9	1.386 (7)	C19—H19B	0.9700
C8—H8	0.9300
C11—Ir1—C11^i	90.6 (2)	C8—C7—H7	120.0
C11—Ir1—N1	80.64 (16)	C6—C7—H7	120.0
C11^i—Ir1—N1	94.70 (15)	C7—C8—C9	119.8 (4)
C11—Ir1—N1^i	94.70 (15)	C7—C8—H8	120.1
C11^i—Ir1—N1^i	80.64 (16)	C9—C8—H8	120.1
N1—Ir1—N1^i	173.42 (19)	C8—C9—C10	120.0 (4)
C11—Ir1—O1	93.5 (5)	C8—C9—H9	120.0
C11^i—Ir1—O1	175.8 (5)	C10—C9—H9	120.0
N1—Ir1—O1	87.2 (6)	C9—C10—C11	122.2 (4)
N1^i—Ir1—O1	97.8 (6)	C9—C10—H10	118.9
C11—Ir1—O1^i	175.8 (5)	C11—C10—H10	118.9
C11^i—Ir1—O1^i	93.5 (5)	C10—C11—C6	116.2 (4)
N1—Ir1—O1^i	97.8 (6)	C10—C11—Ir1	129.1 (3)
N1^i—Ir1—O1^i	87.2 (6)	C6—C11—Ir1	114.7 (3)
O1—Ir1—O1^i	82.5 (9)	C12—O1—Ir1	128.2 (17)
C11—Ir1—O2	172.9 (5)	C17—O2—Ir1	121.0 (16)
C11^i—Ir1—O2	88.2 (4)	O1—C12—C16	125.1 (15)
N1—Ir1—O2	92.5 (6)	O1—C12—C13	125.0 (15)
N1^i—Ir1—O2	92.0 (6)	C16—C12—C13	109.7 (5)
O1—Ir1—O2	88.0 (2)	C14—C13—C12	103.9 (6)
O1^i—Ir1—O2	7.8 (9)	C14—C13—H13A	111.0
C11—Ir1—O2^i	88.2 (4)	C12—C13—H13A	111.0
C11^i—Ir1—O2^i	172.9 (5)	C14—C13—H13B	111.0
N1—Ir1—O2^i	92.0 (6)	C12—C13—H13B	111.0
N1^i—Ir1—O2^i	92.5 (6)	H13A—C13—H13B	109.0
O1—Ir1—O2^i	7.8 (9)	C13—C14—C15	106.2 (6)
O1^i—Ir1—O2^i	88.0 (2)	C13—C14—H14A	110.5
O2—Ir1—O2^i	93.9 (7)	C15—C14—H14A	110.5
C1—N1—C5	119.4 (4)	C13—C14—H14B	110.5
C1—N1—Ir1	124.6 (3)	C15—C14—H14B	110.5
C5—N1—Ir1	116.0 (3)	H14A—C14—H14B	108.7
N1—C1—C2	122.2 (5)	C14—C15—C16	106.4 (6)
N1—C1—H1	118.9	C14—C15—H15A	110.5
C2—C1—H1	118.9	C16—C15—H15A	110.5
C3—C2—C1	118.8 (5)	C14—C15—H15B	110.5
C3—C2—H2	120.6	C16—C15—H15B	110.5
C1—C2—H2	120.6	H15A—C15—H15B	108.6
C2—C3—C4	119.7 (5)	C17—C16—C12	125.3 (6)
C2—C3—H3	120.2	C17—C16—C15	129.7 (8)
C4—C3—H3	120.2	C12—C16—C15	105.0 (6)
C3—C4—C5	119.7 (5)	O2—C17—C16	132.0 (15)
C3—C4—H4	120.2	O2—C17—C18	111.2 (15)
C5—C4—H4	120.2	C16—C17—C18	116.7 (8)
N1—C5—C4	120.3 (4)	Cl1^ii—C19—Cl1	112.0 (6)
N1—C5—C6	113.8 (4)	Cl1^ii—C19—H19A	109.2
C4—C5—C6	125.9 (4)	Cl1—C19—H19A	109.2
C7—C6—C11	121.9 (4)	Cl1^ii—C19—H19B	109.2
C7—C6—C5	123.4 (4)	Cl1—C19—H19B	109.2
C11—C6—C5	114.8 (4)	H19A—C19—H19B	107.9
C8—C7—C6	120.0 (4)
C11—Ir1—N1—C1	177.5 (4)	N1—Ir1—C11—C10	179.3 (4)
C11^i—Ir1—N1—C1	87.7 (4)	N1^i—Ir1—C11—C10	−5.4 (4)
O1—Ir1—N1—C1	−88.5 (6)	O1—Ir1—C11—C10	92.7 (7)
O1^i—Ir1—N1—C1	−6.5 (6)	O2^i—Ir1—C11—C10	86.9 (7)
O2—Ir1—N1—C1	−0.6 (5)	C11^i—Ir1—C11—C6	95.3 (3)
O2^i—Ir1—N1—C1	−94.7 (5)	N1—Ir1—C11—C6	0.6 (3)
C11—Ir1—N1—C5	0.4 (3)	N1^i—Ir1—C11—C6	176.0 (3)
C11^i—Ir1—N1—C5	−89.5 (3)	O1—Ir1—C11—C6	−85.9 (6)
O1—Ir1—N1—C5	94.4 (5)	O2^i—Ir1—C11—C6	−91.7 (6)
O1^i—Ir1—N1—C5	176.4 (5)	C11—Ir1—O1—C12	175.5 (14)
O2—Ir1—N1—C5	−177.8 (5)	N1—Ir1—O1—C12	95.1 (15)
O2^i—Ir1—N1—C5	88.2 (5)	N1^i—Ir1—O1—C12	−89.3 (15)
C5—N1—C1—C2	−0.3 (7)	O1^i—Ir1—O1—C12	−3.2 (9)
Ir1—N1—C1—C2	−177.4 (4)	O2—Ir1—O1—C12	2.4 (19)
N1—C1—C2—C3	−0.4 (9)	O2^i—Ir1—O1—C12	−137 (9)
C1—C2—C3—C4	0.4 (9)	C11^i—Ir1—O2—C17	172.6 (11)
C2—C3—C4—C5	0.1 (8)	N1—Ir1—O2—C17	−92.8 (11)
C1—N1—C5—C4	0.8 (6)	N1^i—Ir1—O2—C17	92.0 (11)
Ir1—N1—C5—C4	178.2 (3)	O1—Ir1—O2—C17	−5.7 (16)
C1—N1—C5—C6	−178.6 (4)	O1^i—Ir1—O2—C17	40 (7)
Ir1—N1—C5—C6	−1.2 (4)	O2^i—Ir1—O2—C17	−0.7 (7)
C3—C4—C5—N1	−0.8 (7)	Ir1—O1—C12—C16	1.9 (17)
C3—C4—C5—C6	178.6 (5)	Ir1—O1—C12—C13	176.8 (14)
N1—C5—C6—C7	−177.8 (4)	O1—C12—C13—C14	167.0 (12)
C4—C5—C6—C7	2.9 (7)	C16—C12—C13—C14	−17.4 (12)
N1—C5—C6—C11	1.8 (5)	C12—C13—C14—C15	28.5 (16)
C4—C5—C6—C11	−177.6 (4)	C13—C14—C15—C16	−29.5 (16)
C11—C6—C7—C8	1.9 (7)	O1—C12—C16—C17	−4.9 (9)
C5—C6—C7—C8	−178.6 (4)	C13—C12—C16—C17	179.6 (8)
C6—C7—C8—C9	−1.6 (7)	O1—C12—C16—C15	175.3 (8)
C7—C8—C9—C10	0.1 (8)	C13—C12—C16—C15	−0.3 (9)
C8—C9—C10—C11	1.1 (7)	C14—C15—C16—C17	−161.8 (12)
C9—C10—C11—C6	−0.8 (6)	C14—C15—C16—C12	18.1 (12)
C9—C10—C11—Ir1	−179.4 (3)	Ir1—O2—C17—C16	5.5 (13)
C7—C6—C11—C10	−0.7 (6)	Ir1—O2—C17—C18	−173.9 (12)
C5—C6—C11—C10	179.7 (4)	C12—C16—C17—O2	0.4 (7)
C7—C6—C11—Ir1	178.1 (3)	C15—C16—C17—O2	−179.8 (4)
C5—C6—C11—Ir1	−1.5 (5)	C12—C16—C17—C18	179.8 (3)
C11^i—Ir1—C11—C10	−86.1 (4)	C15—C16—C17—C18	−0.4 (5)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x, y, −z+3/2.