A cationic rhodium(I) N-heterocyclic carbene complex isolated as an aqua adduct.

The title complex, aqua-[1,3-bis-(2,6-diiso-propyl-phen-yl)imid-az-ol-2-yl-idene](η(4)-cyclo-octa-1,5-diene)rhodium(I) tetra-fluor-ido-borate, [Rh(C(8)H(12))(C(27)H(36)N(2))(H(2)O)]BF(4), exihibits a square-planar geometry around the Rh(I) atom, formed by a bidentate cyclo-octa-1,5-diene (cod) ligand, an N-heterocylcic carbene and an aqua ligand. The complex is cationic and a BF(4) (-) anion balances the charge. The structure exists as a hydrogen-bonded dimer in the solid state, formed via inter-actions between the aqua ligand H atoms and the BF(4) (-) F atoms.

Related literature

For the use of N-heterocyclic carbenes (NHCs) in transfer hydrogenation reactions, see: Gnanamgari et al. (2006 ▶); Nichol et al. (2009 ▶); Hillier et al. (2001 ▶). For aqua adducts, see: Feng et al. (2010 ▶). For an example of intra­molecular H—F bonding, see: Hobbs et al. (2010 ▶). For other NHCs, see: Bappert & Helmchen (2004 ▶); Herrmann et al. (2006 ▶); Nichol et al. (2010 ▶). For the synthesis, see: Yu et al. (2006 ▶). For discussion of complexes with four-coordinate metal atoms, see: Yang et al. (2007 ▶).

Experimental

Crystal data

[Rh(C8H12)(C27H36N2)(H2O)]BF4

M = 704.49

Triclinic,

a = 11.4351 (4) Å

b = 12.2267 (4) Å

c = 12.6198 (4) Å

α = 94.103 (2)°

β = 94.081 (2)°

γ = 97.591 (2)°

V = 1738.66 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.54 mm−1

T = 150 K

0.28 × 0.25 × 0.18 mm

Data collection

Bruker X8 APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.859, T max = 0.907

26258 measured reflections

7097 independent reflections

5888 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.067

S = 1.01

7097 reflections

413 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.61 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalMaker (Palmer, 2009 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033125/om2457sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033125/om2457Isup2.hkl

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

[Rh(C8H12)(C27H36N2)(H2O)]BF4	Z = 2
Mr = 704.49	F(000) = 736
Triclinic, P1	Dx = 1.346 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.4351 (4) Å	Cell parameters from 8324 reflections
b = 12.2267 (4) Å	θ = 2.2–25.1°
c = 12.6198 (4) Å	µ = 0.54 mm−1
α = 94.103 (2)°	T = 150 K
β = 94.081 (2)°	Plate, yellow
γ = 97.591 (2)°	0.28 × 0.25 × 0.18 mm
V = 1738.66 (10) Å3

Bruker X8 APEXII CCD diffractometer	7097 independent reflections
Radiation source: fine-focus sealed tube	5888 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 8.33 pixels mm-1	θmax = 26.4°, θmin = 1.6°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −15→15
Tmin = 0.859, Tmax = 0.907	l = −14→15
26258 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0108P)2 + 1.7615P] where P = (Fo2 + 2Fc2)/3
7097 reflections	(Δ/σ)max = 0.001
413 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.61 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.The hydrogen atoms on the water ligand were located from the difference map and their positions were allowed to refine freely.

	x	y	z	Uiso*/Ueq
Rh1	0.094766 (17)	0.240311 (16)	0.259517 (18)	0.02419 (6)
O1	0.0889 (2)	0.36762 (17)	0.38104 (17)	0.0377 (5)
H1W	0.144 (3)	0.410 (2)	0.409 (2)	0.046 (10)*
H2W	0.028 (3)	0.378 (2)	0.403 (3)	0.050 (10)*
N1	0.32568 (17)	0.37772 (15)	0.20142 (16)	0.0219 (4)
N2	0.36092 (16)	0.26230 (15)	0.31609 (15)	0.0203 (4)
C1	0.2713 (2)	0.29274 (18)	0.25265 (19)	0.0206 (5)
C2	0.4452 (2)	0.4000 (2)	0.2356 (2)	0.0270 (6)
H2	0.5011	0.4559	0.2123	0.032*
C3	0.4672 (2)	0.3287 (2)	0.3071 (2)	0.0265 (6)
H3	0.5412	0.3243	0.3446	0.032*
C4	0.3527 (2)	0.16232 (19)	0.3723 (2)	0.0236 (6)
C5	0.3193 (2)	0.1656 (2)	0.4764 (2)	0.0281 (6)
C6	0.3118 (2)	0.0674 (2)	0.5261 (2)	0.0377 (7)
H6	0.2891	0.0670	0.5971	0.045*
C7	0.3364 (3)	−0.0296 (2)	0.4750 (2)	0.0418 (7)
H7	0.3283	−0.0963	0.5097	0.050*
C8	0.3729 (2)	−0.0288 (2)	0.3732 (2)	0.0374 (7)
H8	0.3918	−0.0953	0.3390	0.045*
C9	0.3827 (2)	0.0663 (2)	0.3193 (2)	0.0281 (6)
C10	0.4301 (2)	0.0665 (2)	0.2099 (2)	0.0353 (7)
H10	0.4051	0.1316	0.1752	0.042*
C11	0.3826 (3)	−0.0376 (2)	0.1365 (3)	0.0497 (8)
H11A	0.4133	−0.1018	0.1645	0.075*
H11B	0.4081	−0.0283	0.0648	0.075*
H11C	0.2959	−0.0492	0.1333	0.075*
C12	0.5661 (3)	0.0812 (3)	0.2204 (3)	0.0476 (8)
H12A	0.5963	0.1492	0.2654	0.071*
H12B	0.5955	0.0863	0.1496	0.071*
H12C	0.5932	0.0176	0.2529	0.071*
C13	0.3004 (2)	0.2726 (2)	0.5371 (2)	0.0333 (6)
H13	0.2906	0.3282	0.4838	0.040*
C14	0.1891 (3)	0.2607 (2)	0.5982 (2)	0.0452 (8)
H14A	0.1207	0.2284	0.5496	0.068*
H14B	0.1760	0.3337	0.6285	0.068*
H14C	0.1995	0.2123	0.6558	0.068*
C15	0.4102 (3)	0.3169 (3)	0.6117 (2)	0.0516 (8)
H15A	0.4221	0.2641	0.6649	0.077*
H15B	0.3993	0.3882	0.6477	0.077*
H15C	0.4796	0.3270	0.5702	0.077*
C16	0.2762 (2)	0.4252 (2)	0.1093 (2)	0.0293 (6)
C17	0.2158 (2)	0.5163 (2)	0.1235 (2)	0.0371 (7)
C18	0.1762 (3)	0.5617 (3)	0.0312 (3)	0.0586 (10)
H18	0.1337	0.6232	0.0374	0.070*
C19	0.1975 (4)	0.5196 (3)	−0.0684 (3)	0.0682 (11)
H19	0.1708	0.5529	−0.1297	0.082*
C20	0.2565 (3)	0.4303 (3)	−0.0798 (3)	0.0579 (10)
H20	0.2693	0.4015	−0.1493	0.069*
C21	0.2983 (3)	0.3804 (2)	0.0081 (2)	0.0386 (7)
C22	0.3690 (3)	0.2848 (2)	−0.0069 (2)	0.0430 (8)
H22	0.3738	0.2491	0.0619	0.052*
C23	0.3121 (3)	0.1959 (3)	−0.0944 (3)	0.0652 (11)
H23A	0.3187	0.2251	−0.1643	0.098*
H23B	0.2284	0.1754	−0.0831	0.098*
H23C	0.3529	0.1304	−0.0914	0.098*
C24	0.4954 (3)	0.3263 (3)	−0.0321 (3)	0.0631 (10)
H24A	0.4933	0.3607	−0.0999	0.095*
H24B	0.5409	0.2638	−0.0375	0.095*
H24C	0.5331	0.3809	0.0249	0.095*
C25	0.1974 (2)	0.5689 (2)	0.2322 (3)	0.0399 (7)
H25	0.2237	0.5199	0.2867	0.048*
C26	0.2731 (3)	0.6816 (2)	0.2541 (3)	0.0612 (10)
H26A	0.3565	0.6733	0.2480	0.092*
H26B	0.2630	0.7124	0.3262	0.092*
H26C	0.2484	0.7317	0.2022	0.092*
C27	0.0672 (3)	0.5797 (3)	0.2451 (3)	0.0773 (12)
H27A	0.0403	0.6305	0.1950	0.116*
H27B	0.0587	0.6087	0.3182	0.116*
H27C	0.0193	0.5069	0.2305	0.116*
C28	−0.1002 (2)	0.2137 (3)	0.2326 (3)	0.0448 (8)
H28	−0.1389	0.2796	0.2545	0.054*
C29	−0.0664 (2)	0.1555 (2)	0.3150 (3)	0.0468 (9)
H29	−0.0857	0.1860	0.3864	0.056*
C30	−0.0549 (3)	0.0337 (3)	0.3089 (3)	0.0744 (13)
H30A	−0.1350	−0.0092	0.3053	0.089*
H30B	−0.0110	0.0175	0.3751	0.089*
C31	0.0080 (3)	−0.0051 (2)	0.2139 (3)	0.0581 (10)
H31A	0.0458	−0.0706	0.2313	0.070*
H31B	−0.0510	−0.0279	0.1523	0.070*
C32	0.1017 (2)	0.0846 (2)	0.1830 (2)	0.0362 (7)
H32	0.1830	0.0629	0.1846	0.043*
C33	0.0804 (2)	0.1599 (2)	0.1078 (2)	0.0343 (7)
H33	0.1499	0.1814	0.0662	0.041*
C34	−0.0368 (3)	0.1690 (3)	0.0490 (3)	0.0586 (10)
H34A	−0.0544	0.1083	−0.0085	0.070*
H34B	−0.0307	0.2399	0.0152	0.070*
C35	−0.1388 (3)	0.1635 (3)	0.1203 (3)	0.0598 (10)
H35A	−0.2012	0.2033	0.0892	0.072*
H35B	−0.1732	0.0852	0.1231	0.072*
B1	0.2301 (3)	0.5986 (3)	0.5597 (3)	0.0379 (8)
F1	0.29175 (14)	0.70097 (12)	0.55244 (14)	0.0479 (4)
F2	0.10977 (14)	0.60203 (19)	0.53299 (17)	0.0860 (8)
F3	0.24800 (18)	0.56624 (15)	0.66043 (15)	0.0629 (5)
F4	0.26616 (13)	0.52218 (12)	0.48522 (13)	0.0409 (4)

	U11	U22	U33	U12	U13	U23
Rh1	0.01932 (10)	0.02176 (11)	0.03008 (12)	−0.00013 (7)	0.00395 (8)	−0.00407 (8)
O1	0.0241 (11)	0.0397 (12)	0.0453 (14)	−0.0032 (10)	0.0089 (11)	−0.0168 (10)
N1	0.0236 (11)	0.0196 (10)	0.0206 (12)	−0.0024 (8)	0.0002 (9)	0.0000 (9)
N2	0.0212 (11)	0.0198 (10)	0.0192 (11)	0.0003 (8)	0.0028 (9)	0.0002 (9)
C1	0.0249 (13)	0.0181 (12)	0.0176 (13)	0.0019 (10)	0.0029 (11)	−0.0049 (10)
C2	0.0212 (13)	0.0268 (14)	0.0305 (16)	−0.0052 (10)	0.0015 (11)	0.0010 (12)
C3	0.0170 (12)	0.0297 (14)	0.0303 (16)	−0.0005 (10)	−0.0022 (11)	−0.0030 (12)
C4	0.0215 (13)	0.0210 (13)	0.0274 (15)	−0.0002 (10)	0.0000 (11)	0.0032 (11)
C5	0.0291 (14)	0.0274 (14)	0.0284 (15)	0.0044 (11)	0.0036 (12)	0.0040 (12)
C6	0.0458 (18)	0.0356 (16)	0.0339 (17)	0.0057 (13)	0.0107 (14)	0.0107 (13)
C7	0.0523 (19)	0.0295 (16)	0.046 (2)	0.0060 (13)	0.0052 (16)	0.0166 (14)
C8	0.0490 (18)	0.0240 (14)	0.0400 (18)	0.0105 (13)	0.0004 (15)	0.0021 (13)
C9	0.0290 (14)	0.0273 (14)	0.0279 (15)	0.0070 (11)	−0.0024 (12)	0.0003 (12)
C10	0.0455 (17)	0.0315 (15)	0.0319 (17)	0.0167 (13)	0.0055 (14)	−0.0009 (13)
C11	0.054 (2)	0.0503 (19)	0.045 (2)	0.0160 (16)	0.0049 (16)	−0.0147 (16)
C12	0.0497 (19)	0.0509 (19)	0.044 (2)	0.0089 (15)	0.0156 (16)	−0.0019 (16)
C13	0.0436 (17)	0.0305 (15)	0.0265 (16)	0.0059 (12)	0.0086 (13)	0.0006 (12)
C14	0.057 (2)	0.0440 (18)	0.0396 (19)	0.0152 (15)	0.0203 (16)	0.0031 (15)
C15	0.063 (2)	0.051 (2)	0.0370 (19)	0.0000 (16)	0.0013 (17)	−0.0064 (16)
C16	0.0331 (15)	0.0273 (14)	0.0246 (15)	−0.0054 (11)	−0.0042 (12)	0.0059 (12)
C17	0.0358 (16)	0.0350 (16)	0.0386 (18)	0.0009 (13)	−0.0069 (14)	0.0082 (14)
C18	0.065 (2)	0.052 (2)	0.059 (3)	0.0150 (17)	−0.0154 (19)	0.0191 (19)
C19	0.093 (3)	0.061 (2)	0.044 (2)	−0.001 (2)	−0.030 (2)	0.0195 (19)
C20	0.095 (3)	0.046 (2)	0.0240 (18)	−0.0153 (19)	−0.0097 (18)	0.0072 (15)
C21	0.0554 (19)	0.0322 (15)	0.0228 (16)	−0.0124 (14)	−0.0009 (14)	0.0038 (13)
C22	0.070 (2)	0.0312 (16)	0.0246 (16)	−0.0068 (15)	0.0121 (15)	−0.0036 (13)
C23	0.093 (3)	0.051 (2)	0.043 (2)	−0.0213 (19)	0.026 (2)	−0.0171 (17)
C24	0.074 (3)	0.047 (2)	0.066 (3)	−0.0060 (18)	0.026 (2)	−0.0096 (18)
C25	0.0368 (16)	0.0337 (16)	0.052 (2)	0.0106 (13)	0.0035 (15)	0.0082 (14)
C26	0.084 (3)	0.0408 (19)	0.057 (2)	0.0006 (18)	0.017 (2)	−0.0047 (17)
C27	0.049 (2)	0.099 (3)	0.094 (3)	0.036 (2)	0.013 (2)	0.031 (3)
C28	0.0180 (14)	0.0496 (18)	0.063 (2)	0.0022 (13)	0.0040 (15)	−0.0201 (18)
C29	0.0329 (17)	0.0409 (18)	0.062 (2)	−0.0142 (14)	0.0287 (16)	−0.0129 (17)
C30	0.083 (3)	0.0376 (19)	0.101 (3)	−0.0153 (18)	0.052 (2)	0.000 (2)
C31	0.055 (2)	0.0267 (16)	0.089 (3)	−0.0075 (14)	0.024 (2)	−0.0086 (17)
C32	0.0294 (15)	0.0243 (14)	0.052 (2)	−0.0008 (11)	0.0074 (14)	−0.0128 (14)
C33	0.0266 (15)	0.0386 (16)	0.0344 (17)	0.0037 (12)	−0.0007 (13)	−0.0145 (14)
C34	0.0424 (19)	0.078 (2)	0.050 (2)	0.0167 (17)	−0.0137 (17)	−0.0255 (19)
C35	0.0266 (16)	0.072 (2)	0.073 (3)	0.0072 (16)	−0.0125 (17)	−0.031 (2)
B1	0.0228 (17)	0.0384 (19)	0.049 (2)	−0.0002 (14)	0.0056 (16)	−0.0154 (17)
F1	0.0514 (10)	0.0286 (9)	0.0596 (12)	0.0034 (8)	−0.0121 (9)	−0.0051 (8)
F2	0.0222 (9)	0.1312 (19)	0.0927 (17)	0.0082 (11)	0.0017 (10)	−0.0643 (15)
F3	0.0855 (15)	0.0551 (12)	0.0446 (12)	−0.0064 (10)	0.0205 (11)	−0.0041 (10)
F4	0.0400 (9)	0.0331 (9)	0.0479 (11)	0.0040 (7)	0.0088 (8)	−0.0118 (8)

Rh1—C1	2.046 (2)	O1—H2W	0.79 (3)
Rh1—C33	2.074 (3)	C2—H2	0.9500
Rh1—C32	2.086 (2)	C3—H3	0.9500
Rh1—O1	2.117 (2)	C6—H6	0.9500
Rh1—C29	2.178 (3)	C7—H7	0.9500
Rh1—C28	2.208 (3)	C8—H8	0.9500
N1—C1	1.366 (3)	C10—H10	1.0000
N1—C2	1.389 (3)	C11—H11A	0.9800
N1—C16	1.449 (3)	C11—H11B	0.9800
N2—C1	1.362 (3)	C11—H11C	0.9800
N2—C3	1.386 (3)	C12—H12A	0.9800
N2—C4	1.452 (3)	C12—H12B	0.9800
C2—C3	1.333 (3)	C12—H12C	0.9800
C4—C5	1.394 (3)	C13—H13	1.0000
C4—C9	1.403 (3)	C14—H14A	0.9800
C5—C6	1.390 (3)	C14—H14B	0.9800
C5—C13	1.516 (3)	C14—H14C	0.9800
C6—C7	1.381 (4)	C15—H15A	0.9800
C7—C8	1.380 (4)	C15—H15B	0.9800
C8—C9	1.384 (4)	C15—H15C	0.9800
C9—C10	1.519 (4)	C18—H18	0.9500
C10—C11	1.533 (4)	C19—H19	0.9500
C10—C12	1.536 (4)	C20—H20	0.9500
C13—C15	1.528 (4)	C22—H22	1.0000
C13—C14	1.530 (4)	C23—H23A	0.9800
C16—C17	1.394 (4)	C23—H23B	0.9800
C16—C21	1.406 (4)	C23—H23C	0.9800
C17—C18	1.398 (4)	C24—H24A	0.9800
C17—C25	1.513 (4)	C24—H24B	0.9800
C18—C19	1.374 (5)	C24—H24C	0.9800
C19—C20	1.362 (5)	C25—H25	1.0000
C20—C21	1.389 (4)	C26—H26A	0.9800
C21—C22	1.516 (4)	C26—H26B	0.9800
C22—C24	1.531 (4)	C26—H26C	0.9800
C22—C23	1.538 (4)	C27—H27A	0.9800
C25—C26	1.524 (4)	C27—H27B	0.9800
C25—C27	1.531 (4)	C27—H27C	0.9800
C28—C29	1.364 (4)	C28—H28	1.0000
C28—C35	1.514 (4)	C29—H29	1.0000
C29—C30	1.509 (4)	C30—H30A	0.9900
C30—C31	1.521 (4)	C30—H30B	0.9900
C31—C32	1.521 (4)	C31—H31A	0.9900
C32—C33	1.399 (4)	C31—H31B	0.9900
C33—C34	1.507 (4)	C32—H32	1.0000
C34—C35	1.520 (4)	C33—H33	1.0000
B1—F1	1.366 (4)	C34—H34A	0.9900
B1—F3	1.368 (4)	C34—H34B	0.9900
B1—F4	1.399 (3)	C35—H35A	0.9900
B1—F2	1.399 (4)	C35—H35B	0.9900
O1—H1W	0.80 (3)
C1—Rh1—C33	92.21 (10)	C12—C10—H10	107.7
C1—Rh1—C32	94.10 (9)	C10—C11—H11A	109.5
C33—Rh1—C32	39.31 (11)	C10—C11—H11B	109.5
C1—Rh1—O1	89.49 (9)	H11A—C11—H11B	109.5
C33—Rh1—O1	159.09 (10)	C10—C11—H11C	109.5
C32—Rh1—O1	161.19 (10)	H11A—C11—H11C	109.5
C1—Rh1—C29	159.12 (12)	H11B—C11—H11C	109.5
C33—Rh1—C29	97.84 (11)	C10—C12—H12A	109.5
C32—Rh1—C29	82.49 (11)	C10—C12—H12B	109.5
O1—Rh1—C29	87.60 (10)	H12A—C12—H12B	109.5
C1—Rh1—C28	164.61 (12)	C10—C12—H12C	109.5
C33—Rh1—C28	81.68 (11)	H12A—C12—H12C	109.5
C32—Rh1—C28	90.08 (11)	H12B—C12—H12C	109.5
O1—Rh1—C28	91.31 (10)	C5—C13—H13	107.6
C29—Rh1—C28	36.23 (12)	C15—C13—H13	107.6
C1—N1—C2	110.6 (2)	C14—C13—H13	107.6
C1—N1—C16	126.3 (2)	C13—C14—H14A	109.5
C2—N1—C16	122.0 (2)	C13—C14—H14B	109.5
C1—N2—C3	111.5 (2)	H14A—C14—H14B	109.5
C1—N2—C4	124.82 (19)	C13—C14—H14C	109.5
C3—N2—C4	122.9 (2)	H14A—C14—H14C	109.5
N2—C1—N1	103.77 (19)	H14B—C14—H14C	109.5
N2—C1—Rh1	125.66 (17)	C13—C15—H15A	109.5
N1—C1—Rh1	129.55 (17)	C13—C15—H15B	109.5
C3—C2—N1	107.5 (2)	H15A—C15—H15B	109.5
C2—C3—N2	106.6 (2)	C13—C15—H15C	109.5
C5—C4—C9	122.7 (2)	H15A—C15—H15C	109.5
C5—C4—N2	119.5 (2)	H15B—C15—H15C	109.5
C9—C4—N2	117.7 (2)	C19—C18—H18	119.2
C6—C5—C4	117.1 (2)	C17—C18—H18	119.2
C6—C5—C13	120.5 (2)	C20—C19—C18	120.4 (3)
C4—C5—C13	122.2 (2)	C20—C19—H19	119.8
C7—C6—C5	121.7 (3)	C18—C19—H19	119.8
C8—C7—C6	119.4 (3)	C19—C20—H20	119.3
C7—C8—C9	121.7 (3)	C21—C20—H20	119.3
C8—C9—C4	117.2 (2)	C21—C22—H22	107.8
C8—C9—C10	120.6 (2)	C24—C22—H22	107.8
C4—C9—C10	122.1 (2)	C23—C22—H22	107.8
C9—C10—C11	113.5 (2)	C22—C23—H23A	109.5
C9—C10—C12	110.4 (2)	C22—C23—H23B	109.5
C11—C10—C12	109.6 (2)	H23A—C23—H23B	109.5
C5—C13—C15	109.8 (2)	C22—C23—H23C	109.5
C5—C13—C14	113.0 (2)	H23A—C23—H23C	109.5
C15—C13—C14	111.0 (2)	H23B—C23—H23C	109.5
C17—C16—C21	122.6 (3)	C22—C24—H24A	109.5
C17—C16—N1	119.7 (2)	C22—C24—H24B	109.5
C21—C16—N1	117.5 (2)	H24A—C24—H24B	109.5
C16—C17—C18	116.6 (3)	C22—C24—H24C	109.5
C16—C17—C25	123.0 (3)	H24A—C24—H24C	109.5
C18—C17—C25	120.3 (3)	H24B—C24—H24C	109.5
C19—C18—C17	121.6 (3)	C17—C25—H25	107.8
C20—C19—C18	120.4 (3)	C26—C25—H25	107.8
C19—C20—C21	121.3 (3)	C27—C25—H25	107.8
C20—C21—C16	117.3 (3)	C25—C26—H26A	109.5
C20—C21—C22	120.1 (3)	C25—C26—H26B	109.5
C16—C21—C22	122.5 (3)	H26A—C26—H26B	109.5
C21—C22—C24	110.8 (2)	C25—C26—H26C	109.5
C21—C22—C23	113.2 (3)	H26A—C26—H26C	109.5
C24—C22—C23	109.2 (2)	H26B—C26—H26C	109.5
C17—C25—C26	110.9 (2)	C25—C27—H27A	109.5
C17—C25—C27	112.3 (3)	C25—C27—H27B	109.5
C26—C25—C27	110.2 (3)	H27A—C27—H27B	109.5
C29—C28—C35	124.6 (3)	C25—C27—H27C	109.5
C29—C28—Rh1	70.69 (16)	H27A—C27—H27C	109.5
C35—C28—Rh1	110.68 (19)	H27B—C27—H27C	109.5
C28—C29—C30	126.3 (3)	C29—C28—H28	114.3
C28—C29—Rh1	73.08 (16)	C35—C28—H28	114.3
C30—C29—Rh1	106.91 (19)	Rh1—C28—H28	114.3
C29—C30—C31	113.9 (3)	C28—C29—H29	114.1
C32—C31—C30	112.1 (2)	C30—C29—H29	114.1
C33—C32—C31	124.0 (3)	Rh1—C29—H29	114.1
C33—C32—Rh1	69.90 (15)	C29—C30—H30A	108.8
C31—C32—Rh1	113.64 (18)	C31—C30—H30A	108.8
C32—C33—C34	126.4 (3)	C29—C30—H30B	108.8
C32—C33—Rh1	70.79 (16)	C31—C30—H30B	108.8
C34—C33—Rh1	111.21 (18)	H30A—C30—H30B	107.7
C33—C34—C35	113.3 (3)	C32—C31—H31A	109.2
C28—C35—C34	112.3 (2)	C30—C31—H31A	109.2
F1—B1—F3	110.1 (3)	C32—C31—H31B	109.2
F1—B1—F4	109.7 (3)	C30—C31—H31B	109.2
F3—B1—F4	110.1 (3)	H31A—C31—H31B	107.9
F1—B1—F2	109.1 (3)	C33—C32—Rh1	69.90 (15)
F3—B1—F2	110.9 (3)	C31—C32—Rh1	113.64 (18)
F4—B1—F2	106.8 (2)	C33—C32—H32	113.9
Rh1—O1—H1W	126 (2)	C31—C32—H32	113.9
Rh1—O1—H2W	120 (2)	Rh1—C32—H32	113.9
H1W—O1—H2W	113 (3)	C32—C33—H33	113.5
C3—C2—H2	126.2	C34—C33—H33	113.5
N1—C2—H2	126.2	Rh1—C33—H33	113.5
C2—C3—N2	106.6 (2)	C33—C34—H34A	108.9
C2—C3—H3	126.7	C35—C34—H34A	108.9
N2—C3—H3	126.7	C33—C34—H34B	108.9
C7—C6—H6	119.1	C35—C34—H34B	108.9
C5—C6—H6	119.1	H34A—C34—H34B	107.7
C8—C7—H7	120.3	C28—C35—H35A	109.1
C6—C7—H7	120.3	C34—C35—H35A	109.1
C7—C8—H8	119.1	C28—C35—H35B	109.1
C9—C8—H8	119.1	C34—C35—H35B	109.1
C9—C10—H10	107.7	H35A—C35—H35B	107.9
C11—C10—H10	107.7

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1W···F4	0.80 (3)	1.97 (3)	2.768 (3)	173 (3)
O1—H2W···F2i	0.79 (3)	1.86 (3)	2.644 (3)	175 (3)

Rh1—C1	2.046 (2)
Rh1—C33	2.074 (3)
Rh1—C32	2.086 (2)
Rh1—O1	2.117 (2)
Rh1—C29	2.178 (3)
Rh1—C28	2.208 (3)

C1—Rh1—C33	92.21 (10)
C1—Rh1—C32	94.10 (9)
C33—Rh1—C32	39.31 (11)
C1—Rh1—O1	89.49 (9)
C33—Rh1—O1	159.09 (10)
C32—Rh1—O1	161.19 (10)
C1—Rh1—C29	159.12 (12)
C33—Rh1—C29	97.84 (11)
C32—Rh1—C29	82.49 (11)
O1—Rh1—C29	87.60 (10)
C1—Rh1—C28	164.61 (12)
C33—Rh1—C28	81.68 (11)
C32—Rh1—C28	90.08 (11)
O1—Rh1—C28	91.31 (10)
C29—Rh1—C28	36.23 (12)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1W⋯F4	0.80 (3)	1.97 (3)	2.768 (3)	173 (3)
O1—H2W⋯F2i	0.79 (3)	1.86 (3)	2.644 (3)	175 (3)

Symmetry code: (i) .