(Diethyl­enetriamine-κ³N)(η⁵-penta­methyl­cyclo­penta­dien­yl)iridium(III) bis­(trifluoro­methane­sulfonate)

The title compound, [Ir(η⁵-C₅Me₅)(dien-κ³N)](CF₃SO₃)₂ (dien is diethyl­enetriamine) or [Ir(C₁₀H₁₅)(C₄H₁₃N₃)](CF₃SO₃)₂, contains a half-sandwich (η⁵-C₅Me₅)Ir^III fragment coordinated in a facial manner by the N atoms of a dien ligand. N—H...O hydrogen bonds to the trifluoro­methane­sulfonate counter-anions link the organometallic cations into a chiral polymeric network.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.015 Å
• R factor = 0.027
• wR factor = 0.064
• Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.56 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        S10
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C10
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        S20
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C20
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.06
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.11
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         15
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety       C131
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety       C141

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               2511
           Count of symmetry unique reflns         2520
           Completeness (_total/calc)             99.64%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  13 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
   4 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: R3m/V (Siemens, 1989); cell refinement: R3m/V; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELXL97.

(Diethylenetriamine-κ³N)(η⁵-pentamethylcyclopentadienyl)iridium(III) bis(trifluoromethanesulfonate)

Crystal data

[Ir(C10H15)(C4H13N3)](CF3SO3)2	F(000) = 1424
Mr = 728.73	Dx = 1.926 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 24 reflections
a = 10.244 (2) Å	θ = 7.2–20.3°
b = 13.733 (3) Å	µ = 5.56 mm^−1
c = 17.869 (4) Å	T = 292 K
V = 2513.8 (9) Å^3	Block, colourless
Z = 4	0.55 × 0.47 × 0.37 mm

Data collection

Siemens P4 4-circle diffractometer	2335 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 25.0°, θmin = 2.3°
ω scans	h = 0→12
Absorption correction: ψ scan (North et al. (1968)	k = 0→16
Tmin = 0.057, Tmax = 0.130	l = 0→21
2511 measured reflections	3 standard reflections every 100 reflections
2511 independent reflections	intensity decay: 0.01%

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)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0389P)^2 + 0.5443P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.064	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.65 e Å^−3
2511 reflections	Δρmin = −0.84 e Å^−3
314 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.0028 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.006 (13)

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.

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
Ir1	0.11588 (2)	0.50957 (2)	0.900041 (16)	0.03172 (12)
C11	−0.0852 (7)	0.4589 (7)	0.9052 (6)	0.048 (2)
C111	−0.1784 (11)	0.4501 (11)	0.8411 (6)	0.079 (4)
H111	−0.2525	0.4119	0.8561	0.119*
H112	−0.1356	0.4188	0.7997	0.119*
H113	−0.2070	0.5137	0.8261	0.119*
C12	−0.0025 (10)	0.3852 (7)	0.9308 (6)	0.054 (3)
C121	0.0057 (14)	0.2832 (8)	0.9033 (10)	0.105 (5)
H121	0.0696	0.2483	0.9320	0.157*
H122	0.0306	0.2833	0.8515	0.157*
H123	−0.0779	0.2523	0.9087	0.157*
C13	0.0632 (9)	0.4229 (8)	0.9964 (6)	0.054 (3)
C131	0.1604 (13)	0.3726 (11)	1.0457 (8)	0.103 (5)
H131	0.2100	0.3270	1.0165	0.154*
H132	0.1154	0.3386	1.0848	0.154*
H133	0.2182	0.4200	1.0672	0.154*
C14	0.0228 (8)	0.5233 (9)	1.0061 (5)	0.054 (3)
C141	0.0583 (11)	0.5906 (12)	1.0688 (6)	0.083 (4)
H141	−0.0010	0.5812	1.1097	0.125*
H142	0.0529	0.6568	1.0517	0.125*
H143	0.1457	0.5771	1.0850	0.125*
C15	−0.0714 (8)	0.5450 (7)	0.9505 (5)	0.042 (2)
C151	−0.1452 (10)	0.6373 (8)	0.9390 (7)	0.071 (3)
H151	−0.0921	0.6915	0.9541	0.106*
H152	−0.2235	0.6361	0.9685	0.106*
H153	−0.1675	0.6438	0.8871	0.106*
N1	0.3214 (6)	0.5063 (7)	0.9212 (4)	0.0410 (17)
H11	0.3354	0.5085	0.9709	0.049*
H12	0.3547	0.4500	0.9039	0.049*
C4	0.3903 (9)	0.5893 (7)	0.8848 (5)	0.050 (2)
H41	0.4109	0.5731	0.8334	0.060*
H42	0.4712	0.6028	0.9110	0.060*
C5	0.3041 (10)	0.6768 (7)	0.8871 (6)	0.053 (3)
H51	0.3398	0.7271	0.8549	0.064*
H52	0.3008	0.7021	0.9377	0.064*
N2	0.1693 (7)	0.6515 (5)	0.8617 (4)	0.0407 (17)
H2	0.1142	0.6943	0.8844	0.049*
C6	0.1437 (10)	0.6582 (7)	0.7807 (5)	0.051 (2)
H61	0.1848	0.7162	0.7606	0.061*
H62	0.0505	0.6629	0.7720	0.061*
C7	0.1972 (10)	0.5692 (8)	0.7422 (5)	0.053 (3)
H71	0.1616	0.5648	0.6920	0.064*
H72	0.2914	0.5743	0.7382	0.064*
N3	0.1621 (7)	0.4796 (6)	0.7856 (3)	0.0406 (18)
H31	0.2294	0.4375	0.7839	0.049*
H32	0.0930	0.4507	0.7637	0.049*
S10	0.5335 (2)	0.8069 (2)	0.69572 (17)	0.0582 (7)
C10	0.6380 (10)	0.7140 (8)	0.7355 (7)	0.085 (4)
F11	0.7622 (7)	0.7340 (7)	0.7250 (6)	0.136 (4)
F12	0.6111 (11)	0.6281 (6)	0.7070 (9)	0.176 (5)
F13	0.6206 (10)	0.7089 (7)	0.8088 (6)	0.133 (4)
O11	0.5663 (12)	0.8064 (9)	0.6189 (5)	0.118 (4)
O12	0.5777 (8)	0.8917 (6)	0.7324 (5)	0.078 (2)
O13	0.4084 (8)	0.7702 (6)	0.7120 (6)	0.091 (3)
S20	0.5156 (2)	0.60147 (15)	0.10090 (14)	0.0412 (5)
C20	0.6366 (8)	0.5041 (6)	0.1044 (4)	0.057 (3)
F21	0.7508 (6)	0.5413 (7)	0.1257 (7)	0.138 (4)
F22	0.6544 (11)	0.4668 (6)	0.0384 (6)	0.147 (4)
F23	0.6039 (8)	0.4382 (5)	0.1536 (4)	0.104 (3)
O21	0.5068 (7)	0.6347 (6)	0.1771 (4)	0.0627 (19)
O22	0.4021 (7)	0.5507 (6)	0.0757 (4)	0.067 (2)
O23	0.5692 (7)	0.6714 (5)	0.0495 (4)	0.0588 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ir1	0.02902 (15)	0.03376 (16)	0.03238 (16)	−0.00514 (13)	0.00313 (13)	−0.00386 (14)
C11	0.026 (4)	0.060 (6)	0.059 (6)	−0.022 (4)	0.008 (5)	0.001 (6)
C111	0.055 (6)	0.121 (11)	0.062 (7)	−0.023 (7)	−0.006 (5)	−0.024 (7)
C12	0.045 (5)	0.043 (5)	0.075 (7)	−0.024 (5)	0.024 (5)	−0.010 (5)
C121	0.095 (10)	0.050 (6)	0.169 (15)	−0.025 (7)	0.047 (12)	−0.017 (10)
C13	0.042 (5)	0.066 (7)	0.054 (6)	−0.015 (5)	0.000 (5)	0.024 (5)
C131	0.072 (8)	0.117 (12)	0.120 (11)	−0.012 (8)	−0.003 (8)	0.078 (10)
C14	0.038 (4)	0.089 (8)	0.034 (4)	−0.027 (5)	0.015 (4)	−0.018 (5)
C141	0.062 (7)	0.137 (12)	0.051 (6)	−0.026 (8)	0.015 (6)	−0.044 (7)
C15	0.032 (4)	0.055 (6)	0.037 (5)	−0.011 (4)	0.011 (4)	−0.010 (4)
C151	0.043 (6)	0.072 (7)	0.097 (9)	0.002 (5)	0.016 (6)	−0.014 (7)
N1	0.028 (3)	0.057 (5)	0.038 (3)	−0.002 (4)	−0.001 (3)	0.006 (4)
C4	0.030 (4)	0.069 (6)	0.052 (6)	−0.023 (5)	0.005 (4)	−0.006 (5)
C5	0.060 (6)	0.050 (5)	0.049 (6)	−0.028 (5)	0.004 (5)	−0.011 (5)
N2	0.044 (4)	0.033 (4)	0.045 (4)	0.001 (3)	0.016 (3)	−0.002 (3)
C6	0.049 (6)	0.046 (5)	0.057 (6)	−0.005 (4)	0.001 (5)	0.011 (5)
C7	0.049 (6)	0.075 (7)	0.034 (5)	−0.010 (5)	0.002 (4)	−0.001 (5)
N3	0.040 (3)	0.050 (5)	0.031 (3)	0.003 (4)	0.004 (3)	−0.006 (3)
S10	0.0524 (14)	0.0582 (15)	0.0641 (16)	−0.0136 (12)	0.0031 (13)	0.0105 (14)
C10	0.065 (9)	0.071 (8)	0.120 (12)	0.003 (7)	0.033 (8)	0.015 (8)
F11	0.060 (5)	0.129 (8)	0.218 (11)	0.023 (5)	0.038 (6)	0.042 (8)
F12	0.135 (8)	0.053 (4)	0.342 (16)	0.013 (6)	0.023 (11)	−0.022 (8)
F13	0.104 (7)	0.157 (9)	0.140 (8)	0.012 (7)	−0.008 (7)	0.077 (7)
O11	0.152 (10)	0.133 (9)	0.070 (6)	−0.060 (8)	0.015 (6)	−0.004 (6)
O12	0.083 (6)	0.058 (4)	0.093 (6)	−0.013 (4)	0.000 (5)	−0.006 (4)
O13	0.046 (5)	0.088 (6)	0.139 (8)	−0.018 (4)	0.002 (6)	0.040 (6)
S20	0.0395 (10)	0.0428 (11)	0.0412 (11)	−0.0059 (9)	0.0009 (11)	0.0015 (12)
C20	0.066 (6)	0.045 (5)	0.061 (6)	0.014 (5)	0.031 (5)	0.038 (6)
F21	0.050 (4)	0.126 (8)	0.236 (11)	0.009 (4)	−0.003 (5)	0.073 (8)
F22	0.180 (10)	0.089 (6)	0.172 (9)	0.031 (6)	0.109 (8)	−0.026 (6)
F23	0.100 (5)	0.065 (4)	0.146 (7)	0.022 (5)	0.027 (5)	0.062 (4)
O21	0.076 (5)	0.064 (5)	0.049 (4)	−0.014 (4)	0.007 (4)	−0.001 (4)
O22	0.057 (4)	0.086 (5)	0.057 (4)	−0.028 (4)	−0.010 (3)	0.004 (4)
O23	0.073 (5)	0.048 (4)	0.056 (4)	−0.009 (4)	0.008 (4)	0.008 (3)

Geometric parameters (Å, º)

Ir1—C14	2.129 (8)	N1—C4	1.489 (11)
Ir1—N2	2.137 (7)	N1—H11	0.9000
Ir1—N3	2.139 (6)	N1—H12	0.9000
Ir1—N1	2.140 (6)	C4—C5	1.491 (14)
Ir1—C13	2.162 (9)	C4—H41	0.9700
Ir1—C12	2.165 (9)	C4—H42	0.9700
Ir1—C15	2.175 (9)	C5—N2	1.495 (12)
Ir1—C11	2.176 (7)	C5—H51	0.9700
C11—C12	1.397 (14)	C5—H52	0.9700
C11—C15	1.440 (12)	N2—C6	1.472 (12)
C11—C111	1.497 (14)	N2—H2	0.9100
C111—H111	0.9600	C6—C7	1.507 (13)
C111—H112	0.9600	C6—H61	0.9700
C111—H113	0.9600	C6—H62	0.9700
C12—C13	1.448 (14)	C7—N3	1.499 (12)
C12—C121	1.486 (15)	C7—H71	0.9700
C121—H121	0.9600	C7—H72	0.9700
C121—H122	0.9600	N3—H31	0.9000
C121—H123	0.9600	N3—H32	0.9000
C13—C14	1.449 (16)	S10—O13	1.407 (8)
C13—C131	1.498 (15)	S10—O12	1.411 (8)
C131—H131	0.9600	S10—O11	1.413 (10)
C131—H132	0.9600	S10—C10	1.811 (13)
C131—H133	0.9600	C10—F12	1.314 (9)
C14—C15	1.415 (13)	C10—F11	1.315 (9)
C14—C141	1.498 (14)	C10—F13	1.324 (9)
C141—H141	0.9600	S20—O22	1.429 (7)
C141—H142	0.9600	S20—O23	1.438 (7)
C141—H143	0.9600	S20—O21	1.438 (7)
C15—C151	1.491 (14)	S20—C20	1.825 (8)
C151—H151	0.9600	C20—F22	1.298 (8)
C151—H152	0.9600	C20—F23	1.305 (7)
C151—H153	0.9600	C20—F21	1.332 (8)
C14—Ir1—N2	108.6 (4)	C14—C15—C151	128.4 (9)
C14—Ir1—N3	165.2 (3)	C11—C15—C151	124.8 (8)
N2—Ir1—N3	79.2 (3)	C14—C15—Ir1	69.1 (5)
C14—Ir1—N1	106.6 (3)	C11—C15—Ir1	70.7 (5)
N2—Ir1—N1	79.8 (3)	C151—C15—Ir1	125.5 (7)
N3—Ir1—N1	87.0 (3)	C15—C151—H151	109.5
C14—Ir1—C13	39.5 (4)	C15—C151—H152	109.5
N2—Ir1—C13	145.2 (4)	H151—C151—H152	109.5
N3—Ir1—C13	135.3 (4)	C15—C151—H153	109.5
N1—Ir1—C13	95.4 (3)	H151—C151—H153	109.5
C14—Ir1—C12	66.0 (4)	H152—C151—H153	109.5
N2—Ir1—C12	160.7 (4)	C4—N1—Ir1	111.9 (5)
N3—Ir1—C12	102.4 (3)	C4—N1—H11	109.2
N1—Ir1—C12	119.3 (4)	Ir1—N1—H11	109.2
C13—Ir1—C12	39.1 (4)	C4—N1—H12	109.2
C14—Ir1—C15	38.4 (3)	Ir1—N1—H12	109.2
N2—Ir1—C15	98.9 (3)	H11—N1—H12	107.9
N3—Ir1—C15	129.4 (3)	N1—C4—C5	108.9 (7)
N1—Ir1—C15	143.1 (3)	N1—C4—H41	109.9
C13—Ir1—C15	64.7 (4)	C5—C4—H41	109.9
C12—Ir1—C15	65.0 (4)	N1—C4—H42	109.9
C14—Ir1—C11	64.3 (4)	C5—C4—H42	109.9
N2—Ir1—C11	123.2 (3)	H41—C4—H42	108.3
N3—Ir1—C11	100.9 (3)	C4—C5—N2	110.6 (7)
N1—Ir1—C11	156.5 (3)	C4—C5—H51	109.5
C13—Ir1—C11	63.5 (4)	N2—C5—H51	109.5
C12—Ir1—C11	37.5 (4)	C4—C5—H52	109.5
C15—Ir1—C11	38.6 (3)	N2—C5—H52	109.5
C12—C11—C15	110.5 (8)	H51—C5—H52	108.1
C12—C11—C111	125.4 (10)	C6—N2—C5	116.6 (7)
C15—C11—C111	124.1 (9)	C6—N2—Ir1	109.1 (6)
C12—C11—Ir1	70.8 (5)	C5—N2—Ir1	110.5 (6)
C15—C11—Ir1	70.6 (4)	C6—N2—H2	106.7
C111—C11—Ir1	126.6 (7)	C5—N2—H2	106.7
C11—C111—H111	109.5	Ir1—N2—H2	106.7
C11—C111—H112	109.5	N2—C6—C7	109.5 (8)
H111—C111—H112	109.5	N2—C6—H61	109.8
C11—C111—H113	109.5	C7—C6—H61	109.8
H111—C111—H113	109.5	N2—C6—H62	109.8
H112—C111—H113	109.5	C7—C6—H62	109.8
C11—C12—C13	106.7 (9)	H61—C6—H62	108.2
C11—C12—C121	127.5 (11)	N3—C7—C6	110.0 (7)
C13—C12—C121	125.3 (12)	N3—C7—H71	109.7
C11—C12—Ir1	71.7 (5)	C6—C7—H71	109.7
C13—C12—Ir1	70.3 (5)	N3—C7—H72	109.7
C121—C12—Ir1	128.9 (8)	C6—C7—H72	109.7
C12—C121—H121	109.5	H71—C7—H72	108.2
C12—C121—H122	109.5	C7—N3—Ir1	112.9 (5)
H121—C121—H122	109.5	C7—N3—H31	109.0
C12—C121—H123	109.5	Ir1—N3—H31	109.0
H121—C121—H123	109.5	C7—N3—H32	109.0
H122—C121—H123	109.5	Ir1—N3—H32	109.0
C12—C13—C14	107.7 (9)	H31—N3—H32	107.8
C12—C13—C131	128.3 (12)	O13—S10—O12	119.5 (6)
C14—C13—C131	124.0 (12)	O13—S10—O11	114.6 (7)
C12—C13—Ir1	70.6 (5)	O12—S10—O11	112.2 (6)
C14—C13—Ir1	69.1 (5)	O13—S10—C10	101.8 (5)
C131—C13—Ir1	123.8 (7)	O12—S10—C10	102.1 (5)
C13—C131—H131	109.5	O11—S10—C10	103.7 (7)
C13—C131—H132	109.5	F12—C10—F11	109.6 (11)
H131—C131—H132	109.5	F12—C10—F13	107.9 (12)
C13—C131—H133	109.5	F11—C10—F13	106.4 (11)
H131—C131—H133	109.5	F12—C10—S10	110.9 (9)
H132—C131—H133	109.5	F11—C10—S10	111.6 (9)
C15—C14—C13	108.1 (8)	F13—C10—S10	110.3 (8)
C15—C14—C141	124.0 (11)	O22—S20—O23	115.8 (4)
C13—C14—C141	127.4 (11)	O22—S20—O21	113.7 (4)
C15—C14—Ir1	72.6 (5)	O23—S20—O21	114.6 (4)
C13—C14—Ir1	71.5 (5)	O22—S20—C20	101.9 (4)
C141—C14—Ir1	127.7 (7)	O23—S20—C20	104.6 (4)
C14—C141—H141	109.5	O21—S20—C20	104.1 (4)
C14—C141—H142	109.5	F22—C20—F23	112.0 (8)
H141—C141—H142	109.5	F22—C20—F21	106.7 (9)
C14—C141—H143	109.5	F23—C20—F21	107.4 (8)
H141—C141—H143	109.5	F22—C20—S20	110.7 (7)
H142—C141—H143	109.5	F23—C20—S20	110.9 (6)
C14—C15—C11	106.8 (9)	F21—C20—S20	109.0 (6)
C14—Ir1—C11—C12	−83.4 (7)	N1—Ir1—C14—C141	45.4 (12)
N2—Ir1—C11—C12	−179.6 (5)	C13—Ir1—C14—C141	123.4 (13)
N3—Ir1—C11—C12	96.2 (6)	C12—Ir1—C14—C141	160.6 (12)
N1—Ir1—C11—C12	−11.6 (13)	C15—Ir1—C14—C141	−119.9 (14)
C13—Ir1—C11—C12	−39.2 (6)	C11—Ir1—C14—C141	−157.9 (13)
C15—Ir1—C11—C12	−121.1 (8)	C13—C14—C15—C11	−2.0 (9)
C14—Ir1—C11—C15	37.7 (6)	C141—C14—C15—C11	−174.8 (8)
N2—Ir1—C11—C15	−58.6 (6)	Ir1—C14—C15—C11	61.0 (6)
N3—Ir1—C11—C15	−142.7 (5)	C13—C14—C15—C151	177.7 (9)
N1—Ir1—C11—C15	109.5 (9)	C141—C14—C15—C151	4.8 (15)
C13—Ir1—C11—C15	81.9 (6)	Ir1—C14—C15—C151	−119.3 (10)
C12—Ir1—C11—C15	121.1 (8)	C13—C14—C15—Ir1	−63.0 (6)
C14—Ir1—C11—C111	156.3 (11)	C141—C14—C15—Ir1	124.1 (9)
N2—Ir1—C11—C111	60.0 (11)	C12—C11—C15—C14	−0.2 (10)
N3—Ir1—C11—C111	−24.1 (10)	C111—C11—C15—C14	178.3 (9)
N1—Ir1—C11—C111	−131.9 (11)	Ir1—C11—C15—C14	−60.0 (6)
C13—Ir1—C11—C111	−159.6 (11)	C12—C11—C15—C151	−179.9 (9)
C12—Ir1—C11—C111	−120.3 (12)	C111—C11—C15—C151	−1.4 (14)
C15—Ir1—C11—C111	118.6 (12)	Ir1—C11—C15—C151	120.4 (9)
C15—C11—C12—C13	2.3 (10)	C12—C11—C15—Ir1	59.7 (6)
C111—C11—C12—C13	−176.2 (9)	C111—C11—C15—Ir1	−121.7 (9)
Ir1—C11—C12—C13	61.9 (6)	N2—Ir1—C15—C14	−108.8 (6)
C15—C11—C12—C121	175.0 (10)	N3—Ir1—C15—C14	167.9 (6)
C111—C11—C12—C121	−3.5 (16)	N1—Ir1—C15—C14	−23.9 (9)
Ir1—C11—C12—C121	−125.4 (11)	C13—Ir1—C15—C14	38.9 (6)
C15—C11—C12—Ir1	−59.6 (6)	C12—Ir1—C15—C14	82.3 (7)
C111—C11—C12—Ir1	121.9 (9)	C11—Ir1—C15—C14	117.5 (9)
C14—Ir1—C12—C11	78.5 (6)	C14—Ir1—C15—C11	−117.5 (9)
N2—Ir1—C12—C11	0.9 (14)	N2—Ir1—C15—C11	133.7 (6)
N3—Ir1—C12—C11	−91.8 (6)	N3—Ir1—C15—C11	50.4 (7)
N1—Ir1—C12—C11	174.7 (6)	N1—Ir1—C15—C11	−141.3 (6)
C13—Ir1—C12—C11	116.1 (9)	C13—Ir1—C15—C11	−78.5 (6)
C15—Ir1—C12—C11	36.2 (5)	C12—Ir1—C15—C11	−35.2 (6)
C14—Ir1—C12—C13	−37.6 (6)	C14—Ir1—C15—C151	123.0 (11)
N2—Ir1—C12—C13	−115.3 (11)	N2—Ir1—C15—C151	14.2 (9)
N3—Ir1—C12—C13	152.1 (6)	N3—Ir1—C15—C151	−69.1 (9)
N1—Ir1—C12—C13	58.6 (7)	N1—Ir1—C15—C151	99.1 (9)
C15—Ir1—C12—C13	−80.0 (6)	C13—Ir1—C15—C151	161.9 (10)
C11—Ir1—C12—C13	−116.1 (9)	C12—Ir1—C15—C151	−154.7 (10)
C14—Ir1—C12—C121	−157.7 (14)	C11—Ir1—C15—C151	−119.6 (10)
N2—Ir1—C12—C121	124.7 (13)	C14—Ir1—N1—C4	−118.6 (6)
N3—Ir1—C12—C121	32.0 (13)	N2—Ir1—N1—C4	−12.0 (6)
N1—Ir1—C12—C121	−61.5 (14)	N3—Ir1—N1—C4	67.5 (6)
C13—Ir1—C12—C121	−120.0 (15)	C13—Ir1—N1—C4	−157.2 (6)
C15—Ir1—C12—C121	160.0 (14)	C12—Ir1—N1—C4	170.0 (6)
C11—Ir1—C12—C121	123.8 (15)	C15—Ir1—N1—C4	−103.4 (7)
C11—C12—C13—C14	−3.5 (10)	C11—Ir1—N1—C4	178.1 (8)
C121—C12—C13—C14	−176.4 (10)	Ir1—N1—C4—C5	35.4 (9)
Ir1—C12—C13—C14	59.3 (6)	N1—C4—C5—N2	−47.6 (10)
C11—C12—C13—C131	178.9 (10)	C4—C5—N2—C6	−88.1 (10)
C121—C12—C13—C131	6.1 (17)	C4—C5—N2—Ir1	37.3 (9)
Ir1—C12—C13—C131	−118.2 (11)	C14—Ir1—N2—C6	−139.8 (6)
C11—C12—C13—Ir1	−62.8 (6)	N3—Ir1—N2—C6	27.2 (6)
C121—C12—C13—Ir1	124.3 (10)	N1—Ir1—N2—C6	116.0 (6)
C14—Ir1—C13—C12	118.7 (8)	C13—Ir1—N2—C6	−159.3 (6)
N2—Ir1—C13—C12	148.4 (6)	C12—Ir1—N2—C6	−69.5 (12)
N3—Ir1—C13—C12	−40.5 (8)	C15—Ir1—N2—C6	−101.5 (6)
N1—Ir1—C13—C12	−131.6 (6)	C11—Ir1—N2—C6	−68.8 (7)
C15—Ir1—C13—C12	80.8 (6)	C14—Ir1—N2—C5	90.7 (6)
C11—Ir1—C13—C12	37.7 (6)	N3—Ir1—N2—C5	−102.3 (6)
N2—Ir1—C13—C14	29.8 (8)	N1—Ir1—N2—C5	−13.5 (6)
N3—Ir1—C13—C14	−159.2 (5)	C13—Ir1—N2—C5	71.2 (8)
N1—Ir1—C13—C14	109.7 (5)	C12—Ir1—N2—C5	161.0 (10)
C12—Ir1—C13—C14	−118.7 (8)	C15—Ir1—N2—C5	129.0 (6)
C15—Ir1—C13—C14	−37.8 (5)	C11—Ir1—N2—C5	161.7 (6)
C11—Ir1—C13—C14	−81.0 (6)	C5—N2—C6—C7	79.2 (10)
C14—Ir1—C13—C131	−117.6 (14)	Ir1—N2—C6—C7	−46.9 (9)
N2—Ir1—C13—C131	−87.9 (13)	N2—C6—C7—N3	44.6 (10)
N3—Ir1—C13—C131	83.2 (12)	C6—C7—N3—Ir1	−21.1 (9)
N1—Ir1—C13—C131	−7.9 (12)	C14—Ir1—N3—C7	120.3 (15)
C12—Ir1—C13—C131	123.7 (15)	N2—Ir1—N3—C7	−3.1 (6)
C15—Ir1—C13—C131	−155.5 (13)	N1—Ir1—N3—C7	−83.3 (6)
C11—Ir1—C13—C131	161.4 (13)	C13—Ir1—N3—C7	−177.9 (6)
C12—C13—C14—C15	3.4 (9)	C12—Ir1—N3—C7	157.3 (6)
C131—C13—C14—C15	−178.9 (9)	C15—Ir1—N3—C7	89.7 (7)
Ir1—C13—C14—C15	63.7 (6)	C11—Ir1—N3—C7	119.0 (7)
C12—C13—C14—C141	175.9 (9)	O13—S10—C10—F12	56.5 (11)
C131—C13—C14—C141	−6.4 (15)	O12—S10—C10—F12	−179.5 (9)
Ir1—C13—C14—C141	−123.7 (9)	O11—S10—C10—F12	−62.7 (10)
C12—C13—C14—Ir1	−60.3 (6)	O13—S10—C10—F11	178.9 (9)
C131—C13—C14—Ir1	117.4 (10)	O12—S10—C10—F11	−57.1 (10)
N2—Ir1—C14—C15	80.7 (6)	O11—S10—C10—F11	59.7 (10)
N3—Ir1—C14—C15	−39.3 (19)	O13—S10—C10—F13	−63.0 (10)
N1—Ir1—C14—C15	165.3 (6)	O12—S10—C10—F13	61.0 (9)
C13—Ir1—C14—C15	−116.7 (8)	O11—S10—C10—F13	177.8 (8)
C12—Ir1—C14—C15	−79.4 (6)	O22—S20—C20—F22	61.5 (7)
C11—Ir1—C14—C15	−37.9 (6)	O23—S20—C20—F22	−59.5 (7)
N2—Ir1—C14—C13	−162.6 (5)	O21—S20—C20—F22	179.9 (6)
N3—Ir1—C14—C13	77.4 (17)	O22—S20—C20—F23	−63.4 (8)
N1—Ir1—C14—C13	−78.0 (6)	O23—S20—C20—F23	175.6 (7)
C12—Ir1—C14—C13	37.3 (6)	O21—S20—C20—F23	55.0 (8)
C15—Ir1—C14—C13	116.7 (8)	O22—S20—C20—F21	178.6 (7)
C11—Ir1—C14—C13	78.8 (6)	O23—S20—C20—F21	57.6 (7)
N2—Ir1—C14—C141	−39.2 (12)	O21—S20—C20—F21	−63.0 (7)
N3—Ir1—C14—C141	−159.2 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H12···O11^i	0.90	2.17	3.062 (14)	171
N2—H2···O23^ii	0.91	2.24	3.080 (10)	154
N3—H31···O12^i	0.90	2.09	2.943 (11)	157
N3—H32···O21^iii	0.90	2.20	3.036 (10)	155
N1—H11···O22^iv	0.90	2.08	2.947 (9)	162

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