Crystal structures of (η⁴-cyclo­octa-1,5-diene)bis(1,3-di­methyl­imidazol-2-yl­idene)iridium(I) iodide and (η⁴-cyclo­octa-1,5-diene)bis­(1,3-di­ethyl­imidazol-2-yl­idene)iridium(I) iodide

(η⁴-Cyclo­octa-1,5-diene)bis­(1,3-di­methyl­imidazol-2-yl­idene)iridium(I) iodide and (η⁴-cyclo­octa-1,5-diene)bis­(1,3-di­ethyl­imidazol-2-yl­idene)iridium(I) iodide were prepared using a modified literature method and crystallized from water in the monoclinic space group C2/m and the ortho­rhom­bic space group Pccn, respectively.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.024
• wR factor = 0.059
• Data-to-parameter ratio = 43.3

Structure: 2

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.030
• wR factor = 0.060
• Data-to-parameter ratio = 48.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         77 Ang   3
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          5 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          7 Report
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.78A   From Ir1             2.29 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.63A   From Ir1             2.21 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.60A   From I1              2.14 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.60A   From Ir1             1.96 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.73A   From Ir1             1.73 eA-3
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.68A   From Ir1             1.56 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          6 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          4 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        17% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       0.50 Check
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4 Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         12 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        300 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          9 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      9.961 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.125 Check
PLAT971_ALERT_2_C Check Calcd Resid. Dens.  0.68A   From Ir1             1.80 eA-3

Alert level G
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       0.50 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        214 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   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
   4 ALERT level G = General information/check it is not something unexpected

   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
   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

---

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (1); ShelXT (Sheldrick, 2015a) for (2). For both structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(η⁴-Cycloocta-1,5-diene)bis(1,3-dimethylimidazol-2-ylidene)iridium(I) iodide (1)

Crystal data

[Ir(C5H8N2)2(C8H12)]I	F(000) = 1176
Mr = 619.54	Dx = 1.930 Mg m^−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
a = 26.6519 (4) Å	Cell parameters from 17811 reflections
b = 8.3070 (2) Å	θ = 2.6–38.3°
c = 9.7852 (2) Å	µ = 7.72 mm^−1
β = 100.241 (2)°	T = 100 K
V = 2131.90 (8) Å^3	Prism, orange
Z = 4	0.54 × 0.22 × 0.11 mm

Data collection

XtaLAB Synergy, Dualflex, HyPix diffractometer	5884 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	5415 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
ω scans	θmax = 38.2°, θmin = 3.1°
Absorption correction: gaussian (CrysAlisPro;Rigaku OD, 2018)	h = −45→44
Tmin = 0.179, Tmax = 0.960	k = −14→13
27006 measured reflections	l = −16→16

Refinement

Refinement on F^2	12 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.059	w = 1/[σ^2(Fo^2) + (0.0317P)^2 + 1.4859P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
5884 reflections	Δρmax = 2.40 e Å^−3
136 parameters	Δρmin = −1.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ir1	0.35715 (2)	0.500000	0.71082 (2)	0.01615 (3)
N1	0.36047 (6)	0.6287 (2)	0.41903 (16)	0.0216 (3)
N2	0.46647 (6)	0.3712 (2)	0.79484 (18)	0.0242 (3)
C1	0.36077 (9)	0.500000	0.5047 (2)	0.0184 (4)
C2	0.36009 (8)	0.5804 (3)	0.28291 (19)	0.0254 (4)
H2	0.359874	0.648608	0.204874	0.031*
C3	0.36109 (11)	0.7956 (3)	0.4619 (2)	0.0346 (5)
H3A	0.394582	0.842411	0.458346	0.052*
H3B	0.354380	0.802066	0.557045	0.052*
H3C	0.334734	0.855247	0.399422	0.052*
C4	0.43494 (9)	0.500000	0.7697 (3)	0.0189 (4)
C5	0.51693 (8)	0.4201 (3)	0.8329 (2)	0.0336 (5)
H5	0.545889	0.352001	0.854780	0.040*
C6	0.45066 (10)	0.2032 (3)	0.7875 (3)	0.0353 (5)
H6A	0.463915	0.149514	0.712161	0.053*
H6B	0.413344	0.197190	0.769749	0.053*
H6C	0.464082	0.149835	0.875787	0.053*
C7	0.27918 (8)	0.4158 (4)	0.6632 (2)	0.0436 (7)
H7A	0.268531	0.362122	0.571156	0.052*	0.485 (19)
H7B	0.270988	0.372499	0.566457	0.052*	0.515 (19)
C8	0.2597 (3)	0.3445 (15)	0.7821 (6)	0.0346 (18)	0.485 (19)
H8A	0.237419	0.251494	0.749983	0.041*	0.485 (19)
H8B	0.239134	0.425165	0.822295	0.041*	0.485 (19)
C9	0.2980 (3)	0.3377 (15)	0.9218 (8)	0.0330 (18)	0.485 (19)
H9A	0.274812	0.415708	0.955269	0.040*	0.485 (19)
H9B	0.303203	0.246025	0.987461	0.040*	0.485 (19)
C10	0.34831 (8)	0.4171 (3)	0.9159 (2)	0.0329 (5)
H10	0.380731	0.371865	0.969269	0.040*	0.485 (19)
H10A	0.378957	0.364754	0.972248	0.040*	0.515 (19)
I1	0.59789 (2)	0.000000	0.87332 (2)	0.03089 (5)
C9A	0.3044 (3)	0.2893 (16)	0.8926 (10)	0.0404 (19)	0.515 (19)
H9AA	0.317748	0.186061	0.863449	0.049*	0.515 (19)
H9AB	0.292215	0.270733	0.981216	0.049*	0.515 (19)
C8A	0.2740 (4)	0.2775 (14)	0.7760 (6)	0.0386 (18)	0.515 (19)
H8AA	0.237614	0.251443	0.773250	0.046*	0.515 (19)
H8AB	0.291638	0.178533	0.753713	0.046*	0.515 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.01272 (4)	0.02483 (5)	0.01113 (4)	0.000	0.00271 (2)	0.000
N1	0.0225 (7)	0.0278 (8)	0.0148 (6)	0.0037 (6)	0.0047 (5)	0.0019 (5)
N2	0.0164 (6)	0.0314 (9)	0.0245 (7)	0.0044 (6)	0.0025 (5)	0.0026 (6)
C1	0.0153 (9)	0.0264 (12)	0.0142 (9)	0.000	0.0044 (7)	0.000
C2	0.0251 (8)	0.0384 (11)	0.0139 (6)	0.0012 (7)	0.0064 (6)	0.0023 (7)
C3	0.0534 (14)	0.0269 (10)	0.0228 (9)	0.0045 (10)	0.0050 (9)	0.0032 (8)
C4	0.0154 (9)	0.0261 (12)	0.0155 (9)	0.000	0.0036 (7)	0.000
C5	0.0168 (7)	0.0498 (14)	0.0334 (11)	0.0050 (8)	0.0019 (7)	0.0024 (9)
C6	0.0324 (11)	0.0291 (11)	0.0430 (13)	0.0065 (9)	0.0032 (9)	0.0033 (9)
C7	0.0195 (8)	0.092 (2)	0.0185 (8)	−0.0201 (11)	0.0007 (6)	0.0036 (10)
C8	0.022 (2)	0.057 (5)	0.024 (2)	−0.012 (3)	0.0043 (17)	0.005 (3)
C9	0.022 (3)	0.063 (5)	0.014 (2)	−0.014 (3)	0.0043 (16)	0.009 (2)
C10	0.0205 (8)	0.0624 (15)	0.0154 (7)	−0.0086 (9)	0.0018 (6)	0.0091 (8)
I1	0.03408 (10)	0.03389 (10)	0.02760 (9)	0.000	0.01334 (7)	0.000
C9A	0.029 (3)	0.069 (6)	0.025 (3)	−0.011 (3)	0.009 (2)	0.012 (3)
C8A	0.034 (3)	0.055 (5)	0.027 (2)	−0.019 (3)	0.006 (2)	0.004 (2)

Geometric parameters (Å, º)

Ir1—C1	2.037 (2)	C6—H6C	0.9800
Ir1—C4	2.051 (2)	C7—C7^i	1.399 (7)
Ir1—C7^i	2.163 (2)	C7—H7A	1.0000
Ir1—C7	2.163 (2)	C7—H7B	1.0000
Ir1—C10^i	2.174 (2)	C7—C8	1.480 (6)
Ir1—C10	2.174 (2)	C7—C8A	1.616 (8)
N1—C1	1.357 (2)	C8—H8A	0.9900
N1—C2	1.389 (2)	C8—H8B	0.9900
N1—C3	1.448 (3)	C8—C9A	1.530 (12)
N2—C4	1.356 (2)	C9—H9A	0.9900
N2—C5	1.391 (3)	C9—H9B	0.9900
N2—C6	1.456 (3)	C9—C10	1.505 (8)
C2—C2^i	1.336 (5)	C9—C8A	1.540 (10)
C2—H2	0.9500	C10—C10^i	1.378 (6)
C3—H3A	0.9800	C10—H10	1.0000
C3—H3B	0.9800	C10—H10A	1.0000
C3—H3C	0.9800	C10—C9A	1.567 (10)
C5—C5^i	1.328 (5)	C9A—H9AA	0.9900
C5—H5	0.9500	C9A—H9AB	0.9900
C6—H6A	0.9800	C8A—H8AA	0.9900
C6—H6B	0.9800	C8A—H8AB	0.9900
C1—Ir1—C4	93.14 (10)	Ir1—C7—H7B	111.1
C1—Ir1—C7	89.97 (9)	C7^i—C7—Ir1	71.14 (10)
C1—Ir1—C7^i	89.97 (9)	C7^i—C7—H7A	116.5
C1—Ir1—C10	161.15 (8)	C7^i—C7—H7B	111.1
C1—Ir1—C10^i	161.16 (8)	C7^i—C7—C8	113.6 (5)
C4—Ir1—C7^i	160.90 (9)	C7^i—C7—C8A	135.3 (4)
C4—Ir1—C7	160.90 (9)	C8—C7—Ir1	114.8 (3)
C4—Ir1—C10	90.61 (8)	C8—C7—H7A	116.5
C4—Ir1—C10^i	90.61 (8)	C8A—C7—Ir1	106.1 (3)
C7^i—Ir1—C7	37.71 (19)	C8A—C7—H7B	111.1
C7—Ir1—C10^i	92.50 (9)	C7—C8—H8A	109.7
C7^i—Ir1—C10	92.49 (9)	C7—C8—H8B	109.7
C7^i—Ir1—C10^i	80.72 (8)	C7—C8—C9A	109.7 (5)
C7—Ir1—C10	80.72 (8)	H8A—C8—H8B	108.2
C10^i—Ir1—C10	36.95 (15)	C9A—C8—H8A	109.7
C1—N1—C2	111.26 (18)	C9A—C8—H8B	109.7
C1—N1—C3	125.22 (17)	H9A—C9—H9B	108.2
C2—N1—C3	123.51 (18)	C10—C9—H9A	109.8
C4—N2—C5	110.93 (19)	C10—C9—H9B	109.8
C4—N2—C6	125.66 (17)	C10—C9—C8A	109.4 (5)
C5—N2—C6	123.40 (19)	C8A—C9—H9A	109.8
N1^i—C1—Ir1	127.97 (11)	C8A—C9—H9B	109.8
N1—C1—Ir1	127.97 (11)	Ir1—C10—H10	112.1
N1—C1—N1^i	103.9 (2)	Ir1—C10—H10A	115.8
N1—C2—H2	126.6	C9—C10—Ir1	114.7 (3)
C2^i—C2—N1	106.78 (12)	C9—C10—H10A	115.8
C2^i—C2—H2	126.6	C10^i—C10—Ir1	71.53 (8)
N1—C3—H3A	109.5	C10^i—C10—C9	116.0 (5)
N1—C3—H3B	109.5	C10^i—C10—H10	112.1
N1—C3—H3C	109.5	C10^i—C10—H10A	115.8
H3A—C3—H3B	109.5	C10^i—C10—C9A	132.7 (5)
H3A—C3—H3C	109.5	C9A—C10—Ir1	106.3 (4)
H3B—C3—H3C	109.5	C9A—C10—H10	112.1
N2—C4—Ir1	127.89 (11)	C8—C9A—C10	111.6 (7)
N2^i—C4—Ir1	127.89 (11)	C8—C9A—H9AA	109.3
N2^i—C4—N2	104.2 (2)	C8—C9A—H9AB	109.3
N2—C5—H5	126.5	C10—C9A—H9AA	109.3
C5^i—C5—N2	106.96 (13)	C10—C9A—H9AB	109.3
C5^i—C5—H5	126.5	H9AA—C9A—H9AB	108.0
N2—C6—H6A	109.5	C7—C8A—H8AA	109.8
N2—C6—H6B	109.5	C7—C8A—H8AB	109.8
N2—C6—H6C	109.5	C9—C8A—C7	109.3 (6)
H6A—C6—H6B	109.5	C9—C8A—H8AA	109.8
H6A—C6—H6C	109.5	C9—C8A—H8AB	109.8
H6B—C6—H6C	109.5	H8AA—C8A—H8AB	108.3
Ir1—C7—H7A	116.5
Ir1—C7—C8—C9A	−21.8 (8)	C5—N2—C4—N2^i	−0.9 (3)
Ir1—C7—C8A—C9	46.8 (7)	C6—N2—C4—Ir1	−1.4 (3)
Ir1—C10—C9A—C8	−43.0 (7)	C6—N2—C4—N2^i	177.51 (16)
C1—N1—C2—C2^i	0.08 (17)	C6—N2—C5—C5^i	−177.88 (18)
C2—N1—C1—Ir1	−176.04 (16)	C7^i—C7—C8—C9A	−101.0 (6)
C2—N1—C1—N1^i	−0.1 (3)	C7^i—C7—C8A—C9	−32.5 (9)
C3—N1—C1—Ir1	4.7 (3)	C7—C8—C9A—C10	43.1 (7)
C3—N1—C1—N1^i	−179.40 (16)	C10—C9—C8A—C7	−44.8 (8)
C3—N1—C2—C2^i	179.37 (17)	C10^i—C10—C9A—C8	36.7 (8)
C4—N2—C5—C5^i	0.58 (19)	C8A—C9—C10—Ir1	21.6 (8)
C5—N2—C4—Ir1	−179.85 (17)	C8A—C9—C10—C10^i	102.2 (6)

Symmetry code: (i) x, −y+1, z.

(η⁴-Cycloocta-1,5-diene)bis(1,3-diethylimidazol-2-ylidene)iridium(I) iodide (2)

Crystal data

[Ir(C7H12N2)2(C8H12)]I	Dx = 1.884 Mg m^−3
Mr = 675.65	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 17338 reflections
a = 10.6041 (2) Å	θ = 2.7–37.9°
b = 12.3058 (2) Å	µ = 6.92 mm^−1
c = 18.2513 (3) Å	T = 100 K
V = 2381.65 (7) Å^3	Block, orange
Z = 4	0.38 × 0.17 × 0.12 mm
F(000) = 1304

Data collection

XtaLAB Synergy, Dualflex, HyPix diffractometer	6352 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	3839 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.062
Detector resolution: 10.0000 pixels mm^-1	θmax = 38.2°, θmin = 2.5°
ω scans	h = −16→17
Absorption correction: gaussian (CrysAlisPro;Rigaku OD, 2018)	k = −21→21
Tmin = 0.318, Tmax = 1.000	l = −30→31
59059 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.060	w = 1/[σ^2(Fo^2) + (0.022P)^2 + 1.4351P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.002
6352 reflections	Δρmax = 1.54 e Å^−3
130 parameters	Δρmin = −0.83 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ir1	0.750000	0.750000	0.50409 (2)	0.01428 (3)
N1	0.66768 (19)	0.56037 (15)	0.40954 (10)	0.0170 (4)
N2	0.5533 (2)	0.69802 (15)	0.38262 (10)	0.0160 (4)
C1	0.6489 (2)	0.66696 (18)	0.42698 (11)	0.0147 (4)
C2	0.5863 (2)	0.52747 (19)	0.35491 (12)	0.0197 (5)
H2	0.582250	0.458717	0.333882	0.024*
C3	0.5145 (2)	0.61300 (19)	0.33789 (13)	0.0193 (4)
H3	0.450781	0.615208	0.302881	0.023*
C4	0.7633 (2)	0.49015 (18)	0.44314 (14)	0.0217 (5)
H4A	0.812864	0.532569	0.477466	0.026*
H4B	0.819765	0.463618	0.405332	0.026*
C5	0.7056 (3)	0.3938 (2)	0.48314 (15)	0.0258 (5)
H5A	0.666738	0.345931	0.448297	0.039*
H5B	0.643277	0.419285	0.517187	0.039*
H5C	0.770442	0.355409	0.509178	0.039*
C6	0.5011 (2)	0.80817 (19)	0.37857 (13)	0.0197 (5)
H6A	0.521838	0.847322	0.423096	0.024*
H6B	0.409999	0.804105	0.374896	0.024*
C7	0.5529 (3)	0.86951 (19)	0.31300 (13)	0.0238 (5)
H7A	0.531961	0.831132	0.268855	0.036*
H7B	0.642915	0.875246	0.317200	0.036*
H7C	0.516639	0.940945	0.311475	0.036*
C8	0.8334 (2)	0.8517 (2)	0.59035 (13)	0.0218 (5)
H8	0.877875	0.916010	0.572020	0.026*
C9	0.9006 (2)	0.7551 (2)	0.58265 (13)	0.0232 (4)
H9	0.983639	0.765350	0.560128	0.028*
C10	0.8939 (3)	0.6559 (2)	0.63123 (15)	0.0317 (6)
H10A	0.940977	0.669868	0.675826	0.038*
H10B	0.933711	0.595331	0.606313	0.038*
C11	0.7595 (3)	0.6247 (2)	0.65118 (15)	0.0329 (6)
H11A	0.756815	0.547796	0.662661	0.039*
H11B	0.734462	0.664384	0.694739	0.039*
I1	0.250000	0.750000	0.71451 (2)	0.02175 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.01317 (5)	0.01477 (5)	0.01492 (5)	−0.00400 (6)	0.000	0.000
N1	0.0177 (10)	0.0156 (8)	0.0176 (9)	−0.0029 (7)	−0.0019 (7)	−0.0005 (7)
N2	0.0179 (10)	0.0145 (9)	0.0155 (8)	−0.0021 (7)	−0.0004 (8)	−0.0007 (7)
C1	0.0151 (10)	0.0148 (9)	0.0144 (9)	−0.0025 (7)	0.0000 (7)	−0.0004 (8)
C2	0.0237 (12)	0.0175 (10)	0.0178 (10)	−0.0052 (9)	−0.0024 (9)	−0.0011 (8)
C3	0.0213 (12)	0.0216 (11)	0.0149 (10)	−0.0029 (9)	−0.0039 (9)	−0.0012 (9)
C4	0.0212 (14)	0.0171 (9)	0.0267 (11)	−0.0022 (9)	−0.0066 (10)	0.0008 (8)
C5	0.0333 (14)	0.0170 (11)	0.0271 (13)	−0.0048 (10)	−0.0070 (11)	0.0032 (10)
C6	0.0194 (12)	0.0193 (11)	0.0205 (11)	0.0035 (9)	0.0006 (9)	−0.0013 (9)
C7	0.0325 (15)	0.0189 (11)	0.0200 (11)	−0.0005 (10)	−0.0016 (10)	0.0007 (9)
C8	0.0190 (12)	0.0247 (12)	0.0216 (11)	−0.0084 (9)	−0.0032 (9)	−0.0039 (10)
C9	0.0175 (9)	0.0292 (11)	0.0230 (10)	−0.0072 (12)	−0.0054 (8)	0.0031 (13)
C10	0.0270 (15)	0.0384 (15)	0.0297 (14)	−0.0029 (12)	−0.0084 (11)	0.0090 (12)
C11	0.0319 (16)	0.0418 (14)	0.0249 (11)	−0.0040 (14)	−0.0006 (13)	0.0124 (11)
I1	0.01710 (8)	0.02436 (9)	0.02378 (10)	−0.00028 (11)	0.000	0.000

Geometric parameters (Å, º)

Ir1—C1^i	2.043 (2)	C5—H5B	0.9600
Ir1—C1	2.043 (2)	C5—H5C	0.9600
Ir1—C8	2.197 (2)	C6—H6A	0.9700
Ir1—C8^i	2.197 (2)	C6—H6B	0.9700
Ir1—C9^i	2.147 (2)	C6—C7	1.518 (3)
Ir1—C9	2.147 (2)	C7—H7A	0.9600
N1—C1	1.364 (3)	C7—H7B	0.9600
N1—C2	1.379 (3)	C7—H7C	0.9600
N1—C4	1.467 (3)	C8—H8	0.9800
N2—C1	1.353 (3)	C8—C9	1.393 (4)
N2—C3	1.389 (3)	C8—C11^i	1.513 (4)
N2—C6	1.466 (3)	C9—H9	0.9800
C2—H2	0.9300	C9—C10	1.510 (4)
C2—C3	1.336 (3)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C4—H4A	0.9700	C10—C11	1.520 (4)
C4—H4B	0.9700	C11—H11A	0.9700
C4—C5	1.521 (3)	C11—H11B	0.9700
C5—H5A	0.9600
C1^i—Ir1—C1	92.93 (12)	H5A—C5—H5B	109.5
C1—Ir1—C8^i	89.85 (9)	H5A—C5—H5C	109.5
C1^i—Ir1—C8^i	171.79 (9)	H5B—C5—H5C	109.5
C1—Ir1—C8	171.79 (9)	N2—C6—H6A	109.4
C1^i—Ir1—C8	89.85 (9)	N2—C6—H6B	109.4
C1^i—Ir1—C9^i	149.88 (10)	N2—C6—C7	111.30 (19)
C1^i—Ir1—C9	93.15 (9)	H6A—C6—H6B	108.0
C1—Ir1—C9	149.88 (10)	C7—C6—H6A	109.4
C1—Ir1—C9^i	93.15 (9)	C7—C6—H6B	109.4
C8^i—Ir1—C8	88.46 (13)	C6—C7—H7A	109.5
C9^i—Ir1—C8	80.66 (9)	C6—C7—H7B	109.5
C9—Ir1—C8	37.37 (10)	C6—C7—H7C	109.5
C9^i—Ir1—C8^i	37.37 (10)	H7A—C7—H7B	109.5
C9—Ir1—C8^i	80.66 (9)	H7A—C7—H7C	109.5
C9^i—Ir1—C9	96.21 (13)	H7B—C7—H7C	109.5
C1—N1—C2	111.1 (2)	Ir1—C8—H8	114.1
C1—N1—C4	124.74 (19)	C9—C8—Ir1	69.36 (13)
C2—N1—C4	124.18 (19)	C9—C8—H8	114.1
C1—N2—C3	111.16 (19)	C9—C8—C11^i	124.8 (2)
C1—N2—C6	125.05 (19)	C11^i—C8—Ir1	111.88 (17)
C3—N2—C6	123.70 (19)	C11^i—C8—H8	114.1
N1—C1—Ir1	124.39 (16)	Ir1—C9—H9	113.1
N2—C1—Ir1	131.63 (17)	C8—C9—Ir1	73.27 (14)
N2—C1—N1	103.98 (19)	C8—C9—H9	113.1
N1—C2—H2	126.5	C8—C9—C10	127.3 (2)
C3—C2—N1	107.1 (2)	C10—C9—Ir1	109.49 (17)
C3—C2—H2	126.5	C10—C9—H9	113.1
N2—C3—H3	126.6	C9—C10—H10A	109.0
C2—C3—N2	106.7 (2)	C9—C10—H10B	109.0
C2—C3—H3	126.6	C9—C10—C11	112.9 (2)
N1—C4—H4A	109.1	H10A—C10—H10B	107.8
N1—C4—H4B	109.1	C11—C10—H10A	109.0
N1—C4—C5	112.4 (2)	C11—C10—H10B	109.0
H4A—C4—H4B	107.8	C8^i—C11—C10	112.7 (2)
C5—C4—H4A	109.1	C8^i—C11—H11A	109.0
C5—C4—H4B	109.1	C8^i—C11—H11B	109.0
C4—C5—H5A	109.5	C10—C11—H11A	109.0
C4—C5—H5B	109.5	C10—C11—H11B	109.0
C4—C5—H5C	109.5	H11A—C11—H11B	107.8
Ir1—C8—C9—C10	−102.1 (2)	C3—N2—C6—C7	−76.3 (3)
Ir1—C9—C10—C11	−39.1 (3)	C4—N1—C1—Ir1	−0.3 (3)
N1—C2—C3—N2	0.1 (3)	C4—N1—C1—N2	179.6 (2)
C1—N1—C2—C3	−0.6 (3)	C4—N1—C2—C3	−179.4 (2)
C1—N1—C4—C5	118.4 (2)	C6—N2—C1—Ir1	2.5 (3)
C1—N2—C3—C2	0.4 (3)	C6—N2—C1—N1	−177.47 (19)
C1—N2—C6—C7	100.0 (3)	C6—N2—C3—C2	177.2 (2)
C2—N1—C1—Ir1	−179.19 (16)	C8—C9—C10—C11	44.4 (4)
C2—N1—C1—N2	0.8 (3)	C9—C10—C11—C8^i	33.9 (3)
C2—N1—C4—C5	−62.9 (3)	C11^i—C8—C9—Ir1	102.9 (2)
C3—N2—C1—Ir1	179.27 (17)	C11^i—C8—C9—C10	0.8 (4)
C3—N2—C1—N1	−0.7 (3)

Symmetry code: (i) −x+3/2, −y+3/2, z.