Chlorido[1-(2-oxidophen-yl)ethyl-idene][tris-(3,5-dimethyl-pyrazol-1-yl)hydro-borato]iridium(III) chloro-form monosolvate.

In the title compound, [Ir(C15H22BN6)(C8H7O)Cl]·CHCl3, the Ir atom is formally trivalent and is coordinated in a slightly distorted octa-hedral geometry by three facial N atoms, one C atom, one O atom and one Cl atom. The Ir=Ccarbene bond is strong and short and exerts a notable effect on the trans-Ir-N bond, which is about 0.10 Å longer than the two other Ir-N bonds. The chloro-form solvent mol-ecule is anchored via a weak C-H⋯Cl hydrogen bond to the Cl atom of the Ir complex mol-ecule. In the crystal, the constituents adopt a layer-like arrangement parallel to (010) and are held together by weak inter-molecular C-H⋯Cl hydrogen bonds, as well as weak Cl⋯Cl [3.498 (2) Å] and Cl⋯π [3.360 (4) Å] inter-actions. A weak intra-molecular C-H⋯O hydrogen bond is also observed.

Related literature

The title compound represents a well crystallizing air-stable chloro­form solvate of a mononuclear iridium complex based on the (hydrogen tris­(3,5-dimethyl­pyrazol­yl)borate-N,N′,N′′)-iridium moiety Ir[TpMe2]. Its formation from [(TpMe2)Ir(C6H5)2(k 1-N2)] (C6H5 = phenyl, N2 = dinitro­gen) and eth­oxy­benzene involved multiple C—C,H,O,Cl bond transformations by the outstanding activity of the Ir[TpMe2] moiety. For general information on C—H and C—C activation, see: Lin & Yamamoto (1999 ▶); Dyker (1999 ▶); Labinger & Bercaw (2002 ▶). For C—H bond activation reactions of ethers by Ir[TpMe2] complexes, see: Lara et al. (2009 ▶); Conejero et al. (2010 ▶); Santos et al. (2013 ▶). For the synthesis of the complex and related crystal structures, see: Gutiérrez-Puebla et al. (1998 ▶); Lara et al. (2009 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

[Ir(C15H22BN6)(C8H7O)Cl]·CHCl3

M = 763.35

Monoclinic,

a = 10.1271 (4) Å

b = 19.1711 (8) Å

c = 14.3154 (6) Å

β = 91.956 (2)°

V = 2777.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 5.22 mm−1

T = 173 K

0.32 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.343, T max = 0.593

52411 measured reflections

8053 independent reflections

6999 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.071

S = 1.02

8053 reflections

341 parameters

H-atom parameters constrained

Δρmax = 1.29 e Å−3

Δρmin = −1.43 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813007344/lh5594sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007344/lh5594Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ir(C15H22BN6)(C8H7O)Cl]·CHCl3	F(000) = 1496
Mr = 763.35	Dx = 1.825 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8986 reflections
a = 10.1271 (4) Å	θ = 2.3–30.0°
b = 19.1711 (8) Å	µ = 5.22 mm−1
c = 14.3154 (6) Å	T = 173 K
β = 91.956 (2)°	Irregular, dark green
V = 2777.7 (2) Å3	0.32 × 0.15 × 0.10 mm
Z = 4

Bruker SMART APEX CCD diffractometer	8053 independent reflections
Radiation source: fine-focus sealed tube	6999 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω and φ scans	θmax = 30.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −14→14
Tmin = 0.343, Tmax = 0.593	k = −26→26
52411 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.038P)2 + 4.5744P] where P = (Fo2 + 2Fc2)/3
8053 reflections	(Δ/σ)max = 0.001
341 parameters	Δρmax = 1.29 e Å−3
0 restraints	Δρmin = −1.43 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ir1	0.436291 (10)	0.157920 (6)	0.682819 (7)	0.01911 (4)
Cl1	0.23334 (8)	0.20336 (4)	0.62640 (6)	0.02847 (15)
B1	0.6944 (4)	0.16488 (19)	0.5669 (3)	0.0262 (7)
H0B	0.7782	0.1680	0.5322	0.031*
N1	0.6159 (3)	0.11309 (14)	0.71808 (18)	0.0227 (5)
N2	0.7168 (3)	0.12094 (14)	0.65687 (19)	0.0247 (5)
N3	0.5334 (3)	0.24641 (14)	0.64204 (18)	0.0234 (5)
N4	0.6481 (3)	0.23785 (15)	0.59388 (19)	0.0257 (5)
N5	0.4663 (3)	0.11764 (14)	0.54460 (18)	0.0225 (5)
N6	0.5867 (3)	0.12870 (14)	0.50605 (18)	0.0236 (5)
O1	0.3316 (2)	0.07061 (11)	0.72065 (14)	0.0216 (4)
C1	0.5825 (4)	0.0473 (2)	0.8677 (3)	0.0357 (8)
H1A	0.5529	0.0884	0.9018	0.054*
H1B	0.6378	0.0181	0.9095	0.054*
H1C	0.5055	0.0205	0.8451	0.054*
C2	0.6607 (3)	0.06994 (17)	0.7866 (2)	0.0267 (6)
C3	0.7896 (3)	0.05026 (19)	0.7680 (3)	0.0323 (7)
H3	0.8448	0.0201	0.8048	0.039*
C4	0.8217 (3)	0.08277 (18)	0.6863 (2)	0.0281 (7)
C5	0.9489 (3)	0.0795 (2)	0.6354 (3)	0.0380 (8)
H5A	0.9295	0.0740	0.5683	0.057*
H5B	1.0014	0.0397	0.6583	0.057*
H5C	0.9989	0.1227	0.6464	0.057*
C6	0.3925 (4)	0.34615 (18)	0.6934 (3)	0.0340 (7)
H6A	0.3425	0.3095	0.7241	0.051*
H6B	0.3359	0.3689	0.6456	0.051*
H6C	0.4224	0.3807	0.7399	0.051*
C7	0.5096 (4)	0.31472 (17)	0.6486 (2)	0.0277 (6)
C8	0.6101 (4)	0.35093 (18)	0.6050 (3)	0.0337 (8)
H8	0.6178	0.4001	0.5992	0.040*
C9	0.6957 (4)	0.30165 (18)	0.5719 (2)	0.0308 (7)
C10	0.8185 (4)	0.3117 (2)	0.5176 (3)	0.0454 (10)
H10A	0.8053	0.2917	0.4550	0.068*
H10B	0.8929	0.2884	0.5501	0.068*
H10C	0.8374	0.3617	0.5124	0.068*
C11	0.2581 (3)	0.05407 (19)	0.5004 (3)	0.0308 (7)
H11A	0.2475	0.0463	0.5674	0.046*
H11B	0.2415	0.0104	0.4664	0.046*
H11C	0.1952	0.0897	0.4781	0.046*
C12	0.3956 (3)	0.07824 (16)	0.4843 (2)	0.0232 (6)
C13	0.4714 (4)	0.06377 (17)	0.4063 (2)	0.0280 (6)
H13	0.4455	0.0369	0.3530	0.034*
C14	0.5906 (3)	0.09640 (17)	0.4225 (2)	0.0263 (6)
C15	0.7068 (4)	0.1003 (2)	0.3615 (3)	0.0387 (9)
H15A	0.7034	0.0615	0.3169	0.058*
H15B	0.7884	0.0973	0.4001	0.058*
H15C	0.7049	0.1446	0.3274	0.058*
C16	0.2741 (3)	0.08151 (19)	0.7994 (2)	0.0280 (6)
C17	0.1875 (4)	0.0306 (2)	0.8350 (3)	0.0377 (8)
H17	0.1654	−0.0100	0.7999	0.045*
C18	0.1364 (4)	0.0413 (3)	0.9210 (3)	0.0500 (11)
H18	0.0767	0.0077	0.9443	0.060*
C19	0.1686 (4)	0.1001 (3)	0.9767 (3)	0.0493 (11)
H19	0.1324	0.1054	1.0366	0.059*
C20	0.2535 (4)	0.1500 (2)	0.9430 (3)	0.0384 (8)
H20	0.2762	0.1896	0.9799	0.046*
C21	0.3070 (3)	0.14175 (19)	0.8528 (2)	0.0282 (7)
C22	0.4044 (3)	0.18475 (18)	0.8105 (2)	0.0263 (6)
C23	0.4790 (4)	0.2367 (2)	0.8696 (3)	0.0356 (8)
H23A	0.4192	0.2741	0.8877	0.053*
H23B	0.5510	0.2563	0.8340	0.053*
H23C	0.5156	0.2136	0.9258	0.053*
C24	0.0420 (5)	0.2910 (2)	0.7869 (4)	0.0508 (11)
H24	0.1171	0.2666	0.7573	0.061*
Cl2	−0.10099 (13)	0.24331 (7)	0.76482 (9)	0.0592 (3)
Cl3	0.07774 (17)	0.29868 (9)	0.90450 (11)	0.0756 (4)
Cl4	0.02838 (17)	0.37582 (8)	0.73962 (13)	0.0804 (5)

	U11	U22	U33	U12	U13	U23
Ir1	0.01915 (6)	0.01930 (6)	0.01887 (6)	−0.00133 (4)	0.00052 (4)	−0.00196 (4)
Cl1	0.0237 (3)	0.0308 (4)	0.0307 (4)	0.0028 (3)	−0.0012 (3)	−0.0030 (3)
B1	0.0226 (16)	0.0281 (18)	0.0280 (17)	−0.0040 (13)	0.0031 (13)	0.0005 (14)
N1	0.0205 (12)	0.0230 (12)	0.0247 (12)	−0.0017 (10)	0.0005 (9)	0.0001 (10)
N2	0.0187 (12)	0.0266 (13)	0.0285 (13)	−0.0012 (10)	−0.0002 (10)	0.0004 (10)
N3	0.0240 (12)	0.0219 (12)	0.0245 (12)	−0.0032 (10)	0.0014 (10)	0.0012 (10)
N4	0.0244 (13)	0.0256 (13)	0.0273 (13)	−0.0041 (10)	0.0022 (10)	0.0008 (10)
N5	0.0227 (12)	0.0223 (12)	0.0225 (12)	−0.0025 (10)	0.0020 (9)	−0.0005 (10)
N6	0.0229 (12)	0.0247 (13)	0.0234 (12)	0.0006 (10)	0.0048 (10)	−0.0001 (10)
O1	0.0229 (10)	0.0216 (10)	0.0207 (10)	−0.0041 (8)	0.0053 (8)	−0.0022 (8)
C1	0.0391 (19)	0.0357 (19)	0.0325 (18)	0.0050 (15)	0.0022 (14)	0.0104 (15)
C2	0.0289 (16)	0.0243 (15)	0.0264 (15)	0.0011 (12)	−0.0046 (12)	0.0003 (12)
C3	0.0267 (16)	0.0341 (18)	0.0355 (18)	0.0043 (13)	−0.0072 (13)	0.0021 (14)
C4	0.0199 (14)	0.0273 (16)	0.0370 (17)	−0.0013 (12)	−0.0032 (12)	−0.0029 (13)
C5	0.0191 (15)	0.046 (2)	0.049 (2)	0.0000 (14)	−0.0007 (14)	−0.0016 (17)
C6	0.046 (2)	0.0254 (17)	0.0305 (17)	0.0046 (14)	−0.0010 (15)	−0.0034 (13)
C7	0.0384 (18)	0.0210 (14)	0.0234 (15)	−0.0032 (13)	−0.0034 (12)	−0.0021 (12)
C8	0.048 (2)	0.0218 (16)	0.0310 (17)	−0.0099 (14)	−0.0032 (15)	0.0013 (13)
C9	0.0359 (18)	0.0272 (16)	0.0291 (16)	−0.0121 (14)	−0.0015 (13)	0.0022 (13)
C10	0.044 (2)	0.042 (2)	0.051 (2)	−0.0161 (18)	0.0114 (19)	0.0053 (19)
C11	0.0297 (16)	0.0307 (17)	0.0316 (17)	−0.0065 (13)	−0.0040 (13)	−0.0030 (13)
C12	0.0288 (15)	0.0188 (13)	0.0217 (14)	−0.0005 (11)	−0.0032 (11)	0.0002 (11)
C13	0.0404 (18)	0.0228 (15)	0.0208 (14)	0.0020 (13)	0.0007 (12)	−0.0010 (11)
C14	0.0353 (17)	0.0212 (14)	0.0226 (14)	0.0042 (12)	0.0051 (12)	0.0015 (11)
C15	0.050 (2)	0.037 (2)	0.0302 (17)	0.0049 (17)	0.0179 (16)	0.0016 (15)
C16	0.0252 (15)	0.0328 (17)	0.0261 (15)	−0.0011 (13)	0.0027 (12)	0.0016 (13)
C17	0.0366 (19)	0.042 (2)	0.0348 (19)	−0.0111 (16)	0.0075 (15)	0.0016 (16)
C18	0.042 (2)	0.069 (3)	0.041 (2)	−0.014 (2)	0.0164 (18)	0.005 (2)
C19	0.042 (2)	0.065 (3)	0.042 (2)	−0.001 (2)	0.0193 (18)	0.004 (2)
C20	0.039 (2)	0.049 (2)	0.0279 (17)	0.0034 (17)	0.0046 (14)	−0.0053 (16)
C21	0.0296 (16)	0.0322 (17)	0.0227 (15)	0.0043 (13)	0.0003 (12)	−0.0021 (12)
C22	0.0260 (15)	0.0267 (15)	0.0261 (15)	0.0035 (12)	−0.0019 (12)	−0.0018 (12)
C23	0.047 (2)	0.0311 (18)	0.0280 (17)	−0.0063 (15)	−0.0033 (15)	−0.0064 (14)
C24	0.044 (2)	0.038 (2)	0.070 (3)	0.0005 (18)	0.014 (2)	−0.014 (2)
Cl2	0.0559 (7)	0.0624 (7)	0.0594 (7)	−0.0145 (6)	0.0056 (5)	−0.0200 (6)
Cl3	0.0868 (10)	0.0707 (9)	0.0678 (9)	−0.0084 (8)	−0.0188 (8)	−0.0070 (7)
Cl4	0.0887 (11)	0.0508 (8)	0.1044 (12)	0.0061 (7)	0.0424 (9)	0.0156 (7)

Ir1—C22	1.937 (3)	C8—C9	1.377 (6)
Ir1—N3	2.056 (3)	C8—H8	0.9500
Ir1—N1	2.059 (3)	C9—C10	1.500 (5)
Ir1—O1	2.063 (2)	C10—H10A	0.9800
Ir1—N5	2.155 (3)	C10—H10B	0.9800
Ir1—Cl1	2.3500 (8)	C10—H10C	0.9800
B1—N4	1.529 (5)	C11—C12	1.492 (5)
B1—N6	1.538 (5)	C11—H11A	0.9800
B1—N2	1.549 (5)	C11—H11B	0.9800
B1—H0B	1.0000	C11—H11C	0.9800
N1—C2	1.350 (4)	C12—C13	1.405 (4)
N1—N2	1.376 (4)	C13—C14	1.373 (5)
N2—C4	1.346 (4)	C13—H13	0.9500
N3—C7	1.336 (4)	C14—C15	1.490 (5)
N3—N4	1.380 (4)	C15—H15A	0.9800
N4—C9	1.356 (4)	C15—H15B	0.9800
N5—C12	1.337 (4)	C15—H15C	0.9800
N5—N6	1.372 (3)	C16—C21	1.418 (5)
N6—C14	1.348 (4)	C16—C17	1.419 (5)
O1—C16	1.303 (4)	C17—C18	1.366 (5)
C1—C2	1.492 (5)	C17—H17	0.9500
C1—H1A	0.9800	C18—C19	1.414 (7)
C1—H1B	0.9800	C18—H18	0.9500
C1—H1C	0.9800	C19—C20	1.383 (6)
C2—C3	1.393 (5)	C19—H19	0.9500
C3—C4	1.374 (5)	C20—C21	1.425 (5)
C3—H3	0.9500	C20—H20	0.9500
C4—C5	1.503 (5)	C21—C22	1.435 (5)
C5—H5A	0.9800	C22—C23	1.494 (5)
C5—H5B	0.9800	C23—H23A	0.9800
C5—H5C	0.9800	C23—H23B	0.9800
C6—C7	1.494 (5)	C23—H23C	0.9800
C6—H6A	0.9800	C24—Cl3	1.716 (6)
C6—H6B	0.9800	C24—Cl2	1.732 (5)
C6—H6C	0.9800	C24—Cl4	1.765 (5)
C7—C8	1.397 (5)	C24—H24	1.0000
C22—Ir1—N3	98.38 (13)	N3—C7—C6	125.0 (3)
C22—Ir1—N1	93.09 (12)	C8—C7—C6	126.3 (3)
N3—Ir1—N1	89.24 (10)	C9—C8—C7	106.8 (3)
C22—Ir1—O1	82.18 (12)	C9—C8—H8	126.6
N3—Ir1—O1	177.55 (9)	C7—C8—H8	126.6
N1—Ir1—O1	93.12 (9)	N4—C9—C8	107.8 (3)
C22—Ir1—N5	174.27 (12)	N4—C9—C10	122.9 (3)
N3—Ir1—N5	87.20 (10)	C8—C9—C10	129.2 (3)
N1—Ir1—N5	85.68 (10)	C9—C10—H10A	109.5
O1—Ir1—N5	92.29 (9)	C9—C10—H10B	109.5
C22—Ir1—Cl1	93.09 (10)	H10A—C10—H10B	109.5
N3—Ir1—Cl1	91.03 (8)	C9—C10—H10C	109.5
N1—Ir1—Cl1	173.71 (8)	H10A—C10—H10C	109.5
O1—Ir1—Cl1	86.56 (6)	H10B—C10—H10C	109.5
N5—Ir1—Cl1	88.06 (7)	C12—C11—H11A	109.5
N4—B1—N6	109.7 (3)	C12—C11—H11B	109.5
N4—B1—N2	108.9 (3)	H11A—C11—H11B	109.5
N6—B1—N2	107.8 (3)	C12—C11—H11C	109.5
N4—B1—H0B	110.1	H11A—C11—H11C	109.5
N6—B1—H0B	110.1	H11B—C11—H11C	109.5
N2—B1—H0B	110.1	N5—C12—C13	109.3 (3)
C2—N1—N2	107.0 (3)	N5—C12—C11	123.9 (3)
C2—N1—Ir1	134.9 (2)	C13—C12—C11	126.9 (3)
N2—N1—Ir1	117.83 (19)	C14—C13—C12	106.1 (3)
C4—N2—N1	109.6 (3)	C14—C13—H13	127.0
C4—N2—B1	130.4 (3)	C12—C13—H13	127.0
N1—N2—B1	119.9 (3)	N6—C14—C13	107.9 (3)
C7—N3—N4	108.0 (3)	N6—C14—C15	123.0 (3)
C7—N3—Ir1	134.4 (2)	C13—C14—C15	129.1 (3)
N4—N3—Ir1	117.6 (2)	C14—C15—H15A	109.5
C9—N4—N3	108.7 (3)	C14—C15—H15B	109.5
C9—N4—B1	130.7 (3)	H15A—C15—H15B	109.5
N3—N4—B1	120.4 (3)	C14—C15—H15C	109.5
C12—N5—N6	106.9 (2)	H15A—C15—H15C	109.5
C12—N5—Ir1	135.0 (2)	H15B—C15—H15C	109.5
N6—N5—Ir1	117.95 (19)	O1—C16—C21	119.6 (3)
C14—N6—N5	109.8 (3)	O1—C16—C17	120.1 (3)
C14—N6—B1	131.9 (3)	C21—C16—C17	120.2 (3)
N5—N6—B1	117.7 (2)	C18—C17—C16	118.6 (4)
C16—O1—Ir1	110.2 (2)	C18—C17—H17	120.7
C2—C1—H1A	109.5	C16—C17—H17	120.7
C2—C1—H1B	109.5	C17—C18—C19	122.7 (4)
H1A—C1—H1B	109.5	C17—C18—H18	118.7
C2—C1—H1C	109.5	C19—C18—H18	118.7
H1A—C1—H1C	109.5	C20—C19—C18	119.3 (4)
H1B—C1—H1C	109.5	C20—C19—H19	120.4
N1—C2—C3	108.7 (3)	C18—C19—H19	120.4
N1—C2—C1	124.7 (3)	C19—C20—C21	120.0 (4)
C3—C2—C1	126.5 (3)	C19—C20—H20	120.0
C4—C3—C2	106.9 (3)	C21—C20—H20	120.0
C4—C3—H3	126.6	C16—C21—C20	119.3 (3)
C2—C3—H3	126.6	C16—C21—C22	113.1 (3)
N2—C4—C3	107.9 (3)	C20—C21—C22	127.3 (3)
N2—C4—C5	123.4 (3)	C21—C22—C23	119.1 (3)
C3—C4—C5	128.7 (3)	C21—C22—Ir1	112.6 (2)
C4—C5—H5A	109.5	C23—C22—Ir1	127.8 (3)
C4—C5—H5B	109.5	C22—C23—H23A	109.5
H5A—C5—H5B	109.5	C22—C23—H23B	109.5
C4—C5—H5C	109.5	H23A—C23—H23B	109.5
H5A—C5—H5C	109.5	C22—C23—H23C	109.5
H5B—C5—H5C	109.5	H23A—C23—H23C	109.5
C7—C6—H6A	109.5	H23B—C23—H23C	109.5
C7—C6—H6B	109.5	Cl3—C24—Cl2	111.8 (3)
H6A—C6—H6B	109.5	Cl3—C24—Cl4	108.0 (3)
C7—C6—H6C	109.5	Cl2—C24—Cl4	111.2 (3)
H6A—C6—H6C	109.5	Cl3—C24—H24	108.6
H6B—C6—H6C	109.5	Cl2—C24—H24	108.6
N3—C7—C8	108.6 (3)	Cl4—C24—H24	108.6
C22—Ir1—N1—C2	45.2 (3)	C1—C2—C3—C4	179.5 (3)
N3—Ir1—N1—C2	143.5 (3)	N1—N2—C4—C3	−0.6 (4)
O1—Ir1—N1—C2	−37.2 (3)	B1—N2—C4—C3	−176.4 (3)
N5—Ir1—N1—C2	−129.2 (3)	N1—N2—C4—C5	179.9 (3)
C22—Ir1—N1—N2	−142.2 (2)	B1—N2—C4—C5	4.2 (5)
N3—Ir1—N1—N2	−43.9 (2)	C2—C3—C4—N2	0.3 (4)
O1—Ir1—N1—N2	135.5 (2)	C2—C3—C4—C5	179.7 (3)
N5—Ir1—N1—N2	43.4 (2)	N4—N3—C7—C8	−0.4 (4)
C2—N1—N2—C4	0.6 (3)	Ir1—N3—C7—C8	−178.1 (2)
Ir1—N1—N2—C4	−173.9 (2)	N4—N3—C7—C6	178.2 (3)
C2—N1—N2—B1	176.9 (3)	Ir1—N3—C7—C6	0.5 (5)
Ir1—N1—N2—B1	2.4 (4)	N3—C7—C8—C9	−0.1 (4)
N4—B1—N2—C4	−129.0 (3)	C6—C7—C8—C9	−178.7 (3)
N6—B1—N2—C4	111.9 (4)	N3—N4—C9—C8	−0.8 (4)
N4—B1—N2—N1	55.6 (4)	B1—N4—C9—C8	173.4 (3)
N6—B1—N2—N1	−63.4 (4)	N3—N4—C9—C10	−178.9 (3)
C22—Ir1—N3—C7	−48.8 (3)	B1—N4—C9—C10	−4.6 (6)
N1—Ir1—N3—C7	−141.8 (3)	C7—C8—C9—N4	0.6 (4)
N5—Ir1—N3—C7	132.5 (3)	C7—C8—C9—C10	178.4 (4)
Cl1—Ir1—N3—C7	44.5 (3)	N6—N5—C12—C13	0.1 (3)
C22—Ir1—N3—N4	133.7 (2)	Ir1—N5—C12—C13	−175.2 (2)
N1—Ir1—N3—N4	40.7 (2)	N6—N5—C12—C11	179.6 (3)
N5—Ir1—N3—N4	−45.0 (2)	Ir1—N5—C12—C11	4.4 (5)
Cl1—Ir1—N3—N4	−133.0 (2)	N5—C12—C13—C14	−0.1 (4)
C7—N3—N4—C9	0.8 (4)	C11—C12—C13—C14	−179.6 (3)
Ir1—N3—N4—C9	178.9 (2)	N5—N6—C14—C13	−0.1 (4)
C7—N3—N4—B1	−174.2 (3)	B1—N6—C14—C13	170.8 (3)
Ir1—N3—N4—B1	4.0 (4)	N5—N6—C14—C15	178.1 (3)
N6—B1—N4—C9	−115.4 (4)	B1—N6—C14—C15	−11.1 (5)
N2—B1—N4—C9	126.7 (3)	C12—C13—C14—N6	0.1 (4)
N6—B1—N4—N3	58.3 (4)	C12—C13—C14—C15	−177.9 (3)
N2—B1—N4—N3	−59.6 (4)	Ir1—O1—C16—C21	−10.4 (4)
N3—Ir1—N5—C12	−143.5 (3)	Ir1—O1—C16—C17	174.7 (3)
N1—Ir1—N5—C12	127.0 (3)	O1—C16—C17—C18	175.3 (4)
O1—Ir1—N5—C12	34.1 (3)	C21—C16—C17—C18	0.4 (6)
Cl1—Ir1—N5—C12	−52.4 (3)	C16—C17—C18—C19	−1.4 (7)
N3—Ir1—N5—N6	41.6 (2)	C17—C18—C19—C20	1.1 (7)
N1—Ir1—N5—N6	−47.8 (2)	C18—C19—C20—C21	0.3 (7)
O1—Ir1—N5—N6	−140.8 (2)	O1—C16—C21—C20	−174.0 (3)
Cl1—Ir1—N5—N6	132.8 (2)	C17—C16—C21—C20	0.9 (5)
C12—N5—N6—C14	0.0 (3)	O1—C16—C21—C22	0.0 (5)
Ir1—N5—N6—C14	176.2 (2)	C17—C16—C21—C22	174.8 (3)
C12—N5—N6—B1	−172.3 (3)	C19—C20—C21—C16	−1.2 (6)
Ir1—N5—N6—B1	3.9 (3)	C19—C20—C21—C22	−174.2 (4)
N4—B1—N6—C14	128.6 (3)	C16—C21—C22—C23	−161.3 (3)
N2—B1—N6—C14	−112.9 (4)	C20—C21—C22—C23	12.0 (5)
N4—B1—N6—N5	−61.1 (4)	C16—C21—C22—Ir1	11.4 (4)
N2—B1—N6—N5	57.4 (4)	C20—C21—C22—Ir1	−175.3 (3)
C22—Ir1—O1—C16	13.0 (2)	N3—Ir1—C22—C21	164.6 (2)
N1—Ir1—O1—C16	105.7 (2)	N1—Ir1—C22—C21	−105.8 (2)
N5—Ir1—O1—C16	−168.5 (2)	O1—Ir1—C22—C21	−13.0 (2)
Cl1—Ir1—O1—C16	−80.6 (2)	Cl1—Ir1—C22—C21	73.1 (2)
N2—N1—C2—C3	−0.4 (4)	N3—Ir1—C22—C23	−23.6 (3)
Ir1—N1—C2—C3	172.8 (2)	N1—Ir1—C22—C23	66.1 (3)
N2—N1—C2—C1	−179.9 (3)	O1—Ir1—C22—C23	158.9 (3)
Ir1—N1—C2—C1	−6.7 (5)	Cl1—Ir1—C22—C23	−115.1 (3)
N1—C2—C3—C4	0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···Cl1	1.00	2.55	3.488 (5)	156
C11—H11A···O1	0.98	2.37	3.230 (4)	146
C11—H11C···Cl3i	0.98	2.65	3.609 (4)	166

Table 1

Selected bond lengths (Å)

Ir1—C22	1.937 (3)
Ir1—N3	2.056 (3)
Ir1—N1	2.059 (3)
Ir1—O1	2.063 (2)
Ir1—N5	2.155 (3)
Ir1—Cl1	2.3500 (8)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24⋯Cl1	1.00	2.55	3.488 (5)	156
C11—H11A⋯O1	0.98	2.37	3.230 (4)	146
C11—H11C⋯Cl3i	0.98	2.65	3.609 (4)	166

Symmetry code: (i) .