[(1,2,5,6-η)-Cyclo­octa-1,5-diene]bis­(1-isopropyl-3-methyl­imidazolin-2-yl­idene)rhodium(I) tetra­fluorido­borate

Nichol, G.S.; Rajaseelan, J.; Walton, D.P.; Rajaseelan, E.

doi:10.1107/S1600536811049890

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1860-m1861

https://doi.org/10.1107/S1600536811049890

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[(1,2,5,6-η)-Cycloocta-1,5-diene]bis(1-isopropyl-3-methylimidazolin-2-ylidene)rhodium(I) tetrafluoridoborate

Gary S. Nichol,^a ^* Jonathan Rajaseelan,^b David P. Walton ^c and Edward Rajaseelan ^c

^aDepartment of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ 85716, USA, ^bLancaster Country Day School, Lancaster, PA 17603, USA, and ^cDepartment of Chemistry, Millersville University, Millersville, PA 17551, USA
^*Correspondence e-mail: gsnichol@email.arizona.edu

(Received 10 November 2011; accepted 21 November 2011; online 30 November 2011)

In the title compound, [Rh(C₈H₁₂)(C₇H₁₂N₂)₂]BF₄, the square-planar Rh complex cation and the BF₄⁻ anion are both bisected by a crystallographic twofold rotation axis. The Rh and B atoms lie on this axis and all others are in general positions. In the crystal, two unique C—H⋯F hydrogen-bonding interactions are present, which involve both imidazolin-2-ylidene H atoms. They form two separate C(5) motifs, the combination of which is a rippled hydrogen-bonded sheet structure in the ab plane.

Related literature

For the structure and dynamics of related N-heterocyclic carbene rhodium and iridium complexes, see: Chianese et al. (2003 ); Köcher & Herrmann (1997 ); Leung et al. (2006 ); Nichol et al. (2009 , 2010 ); Herrmann et al. (2006 ). For the catalytic properties of these complexes, see: Albrecht et al. (2002 ); Frey et al. (2006 ); Gnanamgari et al. (2007 ); Voutchkova et al. (2008 ).

Experimental

Crystal data

[Rh(C₈H₁₂)(C₇H₁₂N₂)₂]BF₄
M_r = 546.27
Orthorhombic, P c c n
a = 11.7508 (6) Å
b = 11.9283 (6) Å
c = 17.3129 (9) Å
V = 2426.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.75 mm⁻¹
T = 100 K
0.38 × 0.37 × 0.37 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.763, T_max = 0.771
234794 measured reflections
14018 independent reflections
10241 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.059
S = 1.13
14018 reflections
218 parameters
All H-atom parameters refined
Δρ_max = 1.55 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯F1ⁱ	0.909 (11)	2.496 (11)	3.3975 (8)	171.4 (10)
C3—H3⋯F2ⁱⁱ	0.877 (12)	2.478 (12)	3.2415 (8)	145.9 (11)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+1, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049890/fj2478sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049890/fj2478Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049890/fj2478Isup3.cdx

checkCIF report

Comment top

We are interested in rhodium and iridium complexes with N-heterocyclic carbene ligands, in particular ligands derived from 1,2,4-triazole-derived compounds (Nichol et al., 2009, 2010). The title compound, (I), was prepared as part of this study (Figure 1). The Rh center has an expected square planar geometry and bond distances are unexceptional. Both the Rh and B atoms lie on a crystallographic twofold rotation axis, which bisects the complex and BF₄^- counterion. C–H···F hydrogen bonding interactions, which involve both imidazolin-2-ylidene H atoms and all four F atoms, form a thick two-dimensional sheet structure in the ab plane (Figure 2).

Related literature top

For the structure and dynamics of related N-heterocyclic carbene rhodium and iridium complexes, see: Chianese et al. (2003); Köcher & Herrmann (1997); Leung et al. (2006); Nichol et al. (2009, 2010); Herrmann et al. (2006). For the catalytic properties of these complexes, see: Albrecht et al. (2002); Frey et al. (2006); Gnanamgari et al. (2007); Voutchkova et al. (2008).

Experimental top

The title compound was synthesized by transmetallation. 1-Isopropyl-3-methylimidazolium bromide (268 mg, 1.31 mmol) was mixed with Ag₂O (152 mg, 0.654 mmol), and was stirred under dark at room temperature for 90 minutes in 10 ml of CH₂Cl₂. The resulting mixture was filtered through Celite into a new flask containing the neutral compound [(cod)Rh(NHC)Cl](585 mg, 1.31 mmol), and AgBF₄(254 mg, 1.31 mmol)and stirred for an additional 90 minutes under dark. The mixture was filtered once more through Celite to remove silver bromide and silver chloride, and the solvent was removed under pressure to give a yellow solid (93%). Crystals of the resulting solid of the title compound, (I), were obtained by slow diffusion of pentane into dichloromethane solution of the compound. ¹H NMR (400 MHz, CDCl₃): δ (p.p.m.) = 7.15 (s, 2 H, NCH), 6.93 (s, 2 H, NCH), 5.03 (m, ³J_H—H = 6.8 Hz, 2 H, CH of ⁱPr), 4.63 (br, 2 H, CH of COD), 4.21 (s, 6 H, N—CH₃), 3.92 (m, 2 H, CH of COD), 2.63 (m, 2 H, CH₂ of COD), 2.42 – 1.92 (m, 6 H, CH₂ of COD), 1.46 (d, ³J_H—H = 6.8 Hz, 6 H, CH₃ of ⁱPr), 1.00 (d, ³J_H—H = 6.8 Hz, 6 H, CH₃ of ⁱPr). ¹³C NMR: δ = 178.76, 178.22 (Ir—C), 124, 117 (N—CH—N), 91.34, 91.25 (N-CHMe₃), 86.36, 86.28 (N—CH₃), 52.60 (CH of COD), 38.10, 33.75, 27.99, (CH₂ of COD), 23.5, 22.90 (CH₃ of ⁱPr).

Structure description top

For the structure and dynamics of related N-heterocyclic carbene rhodium and iridium complexes, see: Chianese et al. (2003); Köcher & Herrmann (1997); Leung et al. (2006); Nichol et al. (2009, 2010); Herrmann et al. (2006). For the catalytic properties of these complexes, see: Albrecht et al. (2002); Frey et al. (2006); Gnanamgari et al. (2007); Voutchkova et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Twice the asymmetric unit of (I), with H atoms omitted. Displacement ellipsoids are at the 50% probability level. Unlabeled atoms are related to labeled atoms by twofold rotation symmetry.
	Fig. 2. A c-axis projection showing C–H···F interactions (blue dotted lines) in (I). Red dotted lines indicate H bond continuation.

[(1,2,5,6-η)-Cycloocta-1,5-diene]bis(1-isopropyl-3- methylimidazolin-2-ylidene)rhodium(I) tetrafluoridoborate top

Crystal data top

[Rh(C₈H₁₂)(C₇H₁₂N₂)₂]BF₄	F(000) = 1128
M_r = 546.27	D_x = 1.495 Mg m⁻³
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 9624 reflections
a = 11.7508 (6) Å	θ = 4.2–51.7°
b = 11.9283 (6) Å	µ = 0.75 mm⁻¹
c = 17.3129 (9) Å	T = 100 K
V = 2426.7 (2) Å³	Block, yellow
Z = 4	0.38 × 0.37 × 0.37 mm

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	14018 independent reflections
Radiation source: fine-focus sealed tube with Miracol optics	10241 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
φ and ω scans	θ_max = 52.3°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→25
T_min = 0.763, T_max = 0.771	k = −26→26
234794 measured reflections	l = −37→38

Refinement top

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)] = 0.020	Hydrogen site location: difference Fourier map
wR(F²) = 0.059	All H-atom parameters refined
S = 1.13	w = 1/[σ²(F_o²) + (0.0182P)² + 0.6772P] where P = (F_o² + 2F_c²)/3
14018 reflections	(Δ/σ)_max = 0.002
218 parameters	Δρ_max = 1.55 e Å⁻³
0 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

[Rh(C₈H₁₂)(C₇H₁₂N₂)₂]BF₄	V = 2426.7 (2) Å³
M_r = 546.27	Z = 4
Orthorhombic, Pccn	Mo Kα radiation
a = 11.7508 (6) Å	µ = 0.75 mm⁻¹
b = 11.9283 (6) Å	T = 100 K
c = 17.3129 (9) Å	0.38 × 0.37 × 0.37 mm

Data collection top

Bruker Kappa APEXII DUO CCD diffractometer	14018 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	10241 reflections with I > 2σ(I)
T_min = 0.763, T_max = 0.771	R_int = 0.033
234794 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	0 restraints
wR(F²) = 0.059	All H-atom parameters refined
S = 1.13	Δρ_max = 1.55 e Å⁻³
14018 reflections	Δρ_min = −0.92 e Å⁻³
218 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Rh1	0.7500	0.2500	0.507678 (3)	0.01052 (1)
N1	0.56243 (4)	0.20105 (4)	0.38873 (3)	0.01399 (6)
N2	0.66738 (4)	0.05648 (4)	0.40496 (3)	0.01512 (6)
C1	0.65651 (4)	0.16534 (4)	0.42664 (3)	0.01295 (6)
C2	0.51512 (5)	0.11598 (5)	0.34425 (4)	0.01757 (8)
H2	0.4526 (10)	0.1269 (10)	0.3143 (7)	0.022 (3)*
C3	0.58158 (5)	0.02502 (5)	0.35458 (4)	0.01811 (8)
H3	0.5769 (10)	−0.0434 (10)	0.3364 (7)	0.028 (3)*
C4	0.51719 (5)	0.31568 (5)	0.39338 (3)	0.01602 (7)
H4	0.5633 (9)	0.3517 (9)	0.4313 (6)	0.019 (3)*
C5	0.53212 (7)	0.37474 (6)	0.31623 (4)	0.02376 (11)
H5A	0.4910 (11)	0.3362 (11)	0.2772 (7)	0.030 (3)*
H5B	0.6089 (11)	0.3778 (11)	0.3028 (8)	0.031 (3)*
H5C	0.5034 (11)	0.4517 (11)	0.3183 (8)	0.035 (3)*
C6	0.39373 (6)	0.31435 (7)	0.41936 (5)	0.02579 (12)
H6A	0.3478 (11)	0.2754 (11)	0.3834 (8)	0.028 (3)*
H6B	0.3635 (11)	0.3876 (11)	0.4230 (8)	0.035 (3)*
H6C	0.3844 (12)	0.2775 (12)	0.4678 (9)	0.033 (3)*
C7	0.75478 (6)	−0.02030 (5)	0.43195 (4)	0.02033 (9)
H7A	0.8005 (10)	0.0166 (10)	0.4689 (7)	0.024 (3)*
H7B	0.7196 (11)	−0.0845 (12)	0.4540 (8)	0.031 (3)*
H7C	0.8014 (11)	−0.0430 (11)	0.3906 (8)	0.032 (3)*
C8	0.61291 (5)	0.22486 (5)	0.59096 (3)	0.01603 (7)
H8	0.5433 (10)	0.2098 (10)	0.5610 (7)	0.021 (3)*
C9	0.68830 (5)	0.13645 (5)	0.60051 (3)	0.01646 (8)
H9	0.6691 (10)	0.0669 (10)	0.5751 (7)	0.025 (3)*
C10	0.77717 (6)	0.12488 (6)	0.66365 (4)	0.01943 (9)
H10A	0.7517 (9)	0.1609 (11)	0.7107 (8)	0.023 (3)*
H10B	0.7852 (10)	0.0442 (11)	0.6775 (7)	0.026 (3)*
C11	0.89369 (5)	0.16926 (6)	0.63829 (4)	0.01888 (9)
H11A	0.9440 (9)	0.1813 (9)	0.6833 (7)	0.020 (2)*
H11B	0.9335 (10)	0.1111 (10)	0.6049 (7)	0.023 (3)*
B1	0.7500	0.7500	0.29593 (6)	0.01705 (12)
F1	0.76439 (5)	0.84479 (5)	0.24966 (3)	0.03003 (10)
F2	0.65419 (4)	0.76347 (4)	0.34218 (3)	0.02659 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Rh1	0.01063 (2)	0.00980 (2)	0.01114 (2)	−0.00124 (1)	0.000	0.000
N1	0.01412 (14)	0.01361 (14)	0.01424 (15)	0.00070 (11)	−0.00193 (11)	−0.00109 (12)
N2	0.01684 (16)	0.01164 (14)	0.01689 (16)	0.00010 (12)	−0.00365 (13)	−0.00144 (12)
C1	0.01345 (15)	0.01194 (15)	0.01347 (16)	−0.00035 (12)	−0.00093 (12)	−0.00044 (12)
C2	0.01794 (19)	0.01713 (19)	0.0176 (2)	−0.00031 (15)	−0.00510 (16)	−0.00262 (15)
C3	0.0211 (2)	0.01475 (18)	0.0185 (2)	−0.00131 (16)	−0.00536 (17)	−0.00293 (15)
C4	0.01615 (18)	0.01608 (18)	0.01583 (18)	0.00398 (14)	−0.00011 (14)	−0.00123 (14)
C5	0.0321 (3)	0.0195 (2)	0.0197 (2)	0.0075 (2)	0.0032 (2)	0.00306 (19)
C6	0.0185 (2)	0.0318 (3)	0.0270 (3)	0.0065 (2)	0.0043 (2)	−0.0023 (2)
C7	0.0218 (2)	0.01268 (16)	0.0265 (3)	0.00234 (17)	−0.0073 (2)	−0.00142 (16)
C8	0.01421 (17)	0.01788 (18)	0.01599 (18)	−0.00244 (14)	0.00177 (14)	−0.00026 (15)
C9	0.01790 (19)	0.01465 (17)	0.01685 (19)	−0.00334 (15)	0.00120 (15)	0.00176 (14)
C10	0.0215 (2)	0.0200 (2)	0.0168 (2)	−0.00095 (18)	−0.00002 (17)	0.00507 (17)
C11	0.0179 (2)	0.0210 (2)	0.0178 (2)	0.00064 (17)	−0.00287 (16)	0.00310 (17)
B1	0.0149 (3)	0.0145 (3)	0.0218 (3)	0.0006 (2)	0.000	0.000
F1	0.0346 (3)	0.0235 (2)	0.0320 (2)	0.00074 (18)	0.00329 (18)	0.01073 (17)
F2	0.01926 (17)	0.02301 (19)	0.0375 (3)	0.00023 (13)	0.00938 (16)	−0.00171 (16)

Geometric parameters (Å, º) top

Rh1—C1	2.0482 (5)	C6—H6A	0.946 (13)
Rh1—C1ⁱ	2.0482 (5)	C6—H6B	0.946 (14)
Rh1—C8	2.1826 (6)	C6—H6C	0.952 (15)
Rh1—C8ⁱ	2.1826 (6)	C7—H7A	0.944 (12)
Rh1—C9	2.2233 (6)	C7—H7B	0.950 (14)
Rh1—C9ⁱ	2.2233 (6)	C7—H7C	0.941 (13)
N1—C1	1.3544 (7)	C8—H8	0.985 (12)
N1—C2	1.3899 (7)	C8—C9	1.3872 (9)
N1—C4	1.4692 (7)	C8—C11ⁱ	1.5074 (9)
N2—C1	1.3577 (7)	C9—H9	0.965 (12)
N2—C3	1.3850 (7)	C9—C10	1.5181 (9)
N2—C7	1.4532 (8)	C10—H10A	0.968 (13)
C2—H2	0.909 (11)	C10—H10B	0.997 (13)
C2—C3	1.3487 (9)	C10—C11	1.5322 (9)
C3—H3	0.877 (12)	C11—C8ⁱ	1.5075 (9)
C4—H4	0.954 (11)	C11—H11A	0.989 (11)
C4—C5	1.5202 (9)	C11—H11B	1.017 (12)
C4—C6	1.5190 (9)	B1—F1	1.3960 (8)
C5—H5A	0.950 (13)	B1—F1ⁱⁱ	1.3960 (8)
C5—H5B	0.933 (13)	B1—F2	1.3908 (8)
C5—H5C	0.979 (14)	B1—F2ⁱⁱ	1.3909 (8)

C1—Rh1—C1ⁱ	93.53 (3)	C4—C6—H6A	110.8 (8)
C1—Rh1—C8	89.36 (2)	C4—C6—H6B	111.7 (8)
C1ⁱ—Rh1—C8ⁱ	89.36 (2)	C4—C6—H6C	112.0 (8)
C1—Rh1—C8ⁱ	156.36 (2)	H6A—C6—H6B	106.4 (11)
C1ⁱ—Rh1—C8	156.36 (2)	H6A—C6—H6C	106.7 (11)
C1—Rh1—C9	91.14 (2)	H6B—C6—H6C	108.9 (11)
C1ⁱ—Rh1—C9	166.03 (2)	N2—C7—H7A	109.0 (7)
C1ⁱ—Rh1—C9ⁱ	91.14 (2)	N2—C7—H7B	109.3 (8)
C1—Rh1—C9ⁱ	166.03 (2)	N2—C7—H7C	110.4 (8)
C8—Rh1—C8ⁱ	97.31 (3)	H7A—C7—H7B	110.6 (11)
C8—Rh1—C9	36.69 (2)	H7A—C7—H7C	108.6 (11)
C8ⁱ—Rh1—C9	81.19 (2)	H7B—C7—H7C	109.0 (11)
C8ⁱ—Rh1—C9ⁱ	36.69 (2)	Rh1—C8—H8	106.8 (7)
C8—Rh1—C9ⁱ	81.19 (2)	Rh1—C8—C9	73.25 (3)
C9—Rh1—C9ⁱ	87.42 (3)	Rh1—C8—C11ⁱ	106.38 (4)
C1—N1—C2	111.43 (5)	H8—C8—C9	117.0 (7)
C1—N1—C4	124.16 (5)	H8—C8—C11ⁱ	113.3 (7)
C2—N1—C4	124.41 (5)	C9—C8—C11ⁱ	127.23 (5)
C1—N2—C3	111.39 (5)	Rh1—C9—C8	70.06 (3)
C1—N2—C7	125.48 (5)	Rh1—C9—H9	105.7 (7)
C3—N2—C7	123.10 (5)	Rh1—C9—C10	110.59 (4)
Rh1—C1—N1	127.93 (4)	C8—C9—H9	116.7 (7)
Rh1—C1—N2	127.62 (4)	C8—C9—C10	126.46 (6)
N1—C1—N2	104.10 (4)	H9—C9—C10	114.2 (7)
N1—C2—H2	122.4 (7)	C9—C10—H10A	110.7 (7)
N1—C2—C3	106.40 (5)	C9—C10—H10B	109.0 (7)
H2—C2—C3	131.2 (7)	C9—C10—C11	112.14 (5)
N2—C3—C2	106.68 (5)	H10A—C10—H10B	104.8 (11)
N2—C3—H3	121.6 (8)	H10A—C10—C11	111.3 (7)
C2—C3—H3	131.7 (8)	H10B—C10—C11	108.6 (7)
N1—C4—H4	104.6 (7)	C8ⁱ—C11—C10	113.53 (5)
N1—C4—C5	109.96 (5)	C8ⁱ—C11—H11A	109.7 (7)
N1—C4—C6	110.61 (5)	C8ⁱ—C11—H11B	106.6 (7)
H4—C4—C5	109.3 (7)	C10—C11—H11A	111.0 (7)
H4—C4—C6	110.0 (7)	C10—C11—H11B	109.8 (7)
C5—C4—C6	112.04 (6)	H11A—C11—H11B	105.8 (9)
C4—C5—H5A	110.0 (8)	F1—B1—F1ⁱⁱ	109.97 (9)
C4—C5—H5B	110.4 (8)	F1—B1—F2	109.56 (3)
C4—C5—H5C	111.2 (8)	F1ⁱⁱ—B1—F2	109.02 (3)
H5A—C5—H5B	109.5 (11)	F1ⁱⁱ—B1—F2ⁱⁱ	109.56 (3)
H5A—C5—H5C	107.7 (11)	F1—B1—F2ⁱⁱ	109.02 (3)
H5B—C5—H5C	107.9 (11)	F2—B1—F2ⁱⁱ	109.70 (9)

C2—N1—C1—Rh1	−173.45 (4)	C2—N1—C4—C6	56.65 (8)
C2—N1—C1—N2	0.13 (6)	C1—Rh1—C8—C9	92.76 (4)
C4—N1—C1—Rh1	7.28 (8)	C1ⁱ—Rh1—C8—C9	−169.87 (5)
C4—N1—C1—N2	−179.14 (5)	C1ⁱ—Rh1—C8—C11ⁱ	−45.11 (7)
C3—N2—C1—Rh1	173.54 (4)	C1—Rh1—C8—C11ⁱ	−142.49 (4)
C3—N2—C1—N1	−0.07 (6)	C8ⁱ—Rh1—C8—C9	−64.50 (3)
C7—N2—C1—Rh1	−4.70 (8)	C8ⁱ—Rh1—C8—C11ⁱ	60.26 (4)
C7—N2—C1—N1	−178.31 (6)	C9ⁱ—Rh1—C8—C9	−97.57 (4)
C1ⁱ—Rh1—C1—N1	−83.65 (5)	C9—Rh1—C8—C11ⁱ	124.75 (6)
C1ⁱ—Rh1—C1—N2	104.22 (5)	C9ⁱ—Rh1—C8—C11ⁱ	27.19 (4)
C8—Rh1—C1—N1	72.88 (5)	Rh1—C8—C9—C10	101.36 (6)
C8ⁱ—Rh1—C1—N1	179.85 (5)	C11ⁱ—C8—C9—Rh1	−98.12 (6)
C8—Rh1—C1—N2	−99.26 (5)	C11ⁱ—C8—C9—C10	3.25 (9)
C8ⁱ—Rh1—C1—N2	7.72 (8)	C1—Rh1—C9—C8	−87.40 (4)
C9—Rh1—C1—N1	109.52 (5)	C1ⁱ—Rh1—C9—C8	163.01 (8)
C9ⁱ—Rh1—C1—N1	25.66 (11)	C1—Rh1—C9—C10	149.98 (4)
C9—Rh1—C1—N2	−62.61 (5)	C1ⁱ—Rh1—C9—C10	40.40 (11)
C9ⁱ—Rh1—C1—N2	−146.48 (8)	C8ⁱ—Rh1—C9—C8	115.05 (4)
C1—N1—C2—C3	−0.15 (7)	C8—Rh1—C9—C10	−122.61 (6)
C4—N1—C2—C3	179.12 (5)	C8ⁱ—Rh1—C9—C10	−7.56 (4)
N1—C2—C3—N2	0.09 (7)	C9ⁱ—Rh1—C9—C8	78.69 (3)
C1—N2—C3—C2	−0.01 (7)	C9ⁱ—Rh1—C9—C10	−43.92 (4)
C7—N2—C3—C2	178.27 (6)	Rh1—C9—C10—C11	−13.94 (7)
C1—N1—C4—C5	111.55 (6)	C8—C9—C10—C11	−93.84 (7)
C1—N1—C4—C6	−124.17 (6)	C9—C10—C11—C8ⁱ	39.69 (8)
C2—N1—C4—C5	−67.63 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F1ⁱⁱⁱ	0.909 (11)	2.496 (11)	3.3975 (8)	171.4 (10)
C3—H3···F2^iv	0.877 (12)	2.478 (12)	3.2415 (8)	145.9 (11)

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

Experimental details

Crystal data
Chemical formula	[Rh(C₈H₁₂)(C₇H₁₂N₂)₂]BF₄
M_r	546.27
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	100
a, b, c (Å)	11.7508 (6), 11.9283 (6), 17.3129 (9)
V (Å³)	2426.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.38 × 0.37 × 0.37

Data collection
Diffractometer	Bruker Kappa APEXII DUO CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.763, 0.771
No. of measured, independent and observed [I > 2σ(I)] reflections	234794, 14018, 10241
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	1.113

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.059, 1.13
No. of reflections	14018
No. of parameters	218
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	1.55, −0.92

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F1ⁱ	0.909 (11)	2.496 (11)	3.3975 (8)	171.4 (10)
C3—H3···F2ⁱⁱ	0.877 (12)	2.478 (12)	3.2415 (8)	145.9 (11)

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

Acknowledgements

JR and DPW thank the Department of Chemistry, Millersville University, for project funding. The diffractometer was purchased with funding from NSF grant CHE-0741837.

References

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

[(1,2,5,6-η)-Cyclo­octa-1,5-diene]bis­­(1-iso­propyl-3-methyl­imidazolin-2-yl­­idene)rhodium(I) tetra­fluorido­borate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[(1,2,5,6-η)-Cycloocta-1,5-diene]bis(1-isopropyl-3-methylimidazolin-2-ylidene)rhodium(I) tetrafluoridoborate