(3-Methyl­benzo­nitrile-1κN)-cis-tetra­kis(μ-N-phenyl­acetamidato)-1:2κ4N:O;1:2κ4O:N-dirhodium(II)(Rh—Rh)

Eagle, C.T.; Quarshie, F.; Cook, K.M.

doi:10.1107/S1600536814016031

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 8| August 2014| Page m304

doi:10.1107/S1600536814016031

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(3-Methylbenzonitrile-1κN)-cis-tetrakis(μ-N-phenylacetamidato)-1:2κ⁴N:O;1:2κ⁴O:N-dirhodium(II)(Rh—Rh)

Cassandra T. Eagle,^a ^* Fredricka Quarshie ^a and Kevin M. Cook ^a

^aDepartment of Chemistry, East Tennessee State University, PO Box 70695, Johnson City, TN 37614, USA
^*Correspondence e-mail: eaglec@etsu.edu

Edited by J. T. Mague, Tulane University, USA (Received 13 June 2014; accepted 9 July 2014; online 23 July 2014)

The complex molecule of the title compound, [Rh₂{N(C₆H₅)COCH₃}₄(NCC₇H₇)], has crystallographically-imposed mirror symmetry. The four acetamide ligands bridging the dirhodium core are arranged in a 2,2-cis manner with two N atoms and two O atoms coordinating to the unique Rh^II atom cis to one another. The N_eq—Rh—Rh—O_eq torsion angles on the acetamide bridge are 0.75 (7) and 1.99 (9)°. The axial nitrile ligand completes the distorted octahedral coordination sphere of one Rh^II atom and shows a nonlinear coordination, with an Rh—N—C bond angle of 162.8 (5)°; the N—C bond length is 1.154 (7) Å.

Keywords: crystal structure.

CCDC reference: 1013071

Related literature

For the synthesis and structure of four related compounds, see: Lifsey et al. (1987 ); Eagle et al. (2000 , 2012 , 2013a ,b ).

Experimental

Crystal data

[Rh₂(C₈H₈NO)₄(C₈H₇N)]
M_r = 859.59
Orthorhombic, P n m a
a = 15.3319 (14) Å
b = 18.3248 (16) Å
c = 12.9564 (12) Å
V = 3640.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 223 K
0.17 × 0.15 × 0.14 mm

Data collection

Rigaku XtaLAB mini diffractometer
Absorption correction: multi-scan (REQAB; Rigaku, 1998 ) T_min = 0.664, T_max = 0.873
36328 measured reflections
4292 independent reflections
3154 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.089
S = 1.05
4292 reflections
250 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 2010 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure.

Supporting information

CCDC reference: 1013071

Crystal structure: contains datablocks General, I. DOI: 10.1107/S1600536814016031/mw2125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016031/mw2125Isup2.hkl

checkCIF report

Experimental top

Synthesis and crystallization top

Approximately 10mg of cis-tetrakis[µ-N-(phenyl)acetamidato]-κ⁴N:O;κ⁴O:N dirhodium(II)] was dissolved in 18 mL of dichloromethane. 4µL of neat 3-methyl benzonitrile and 2µL of acetone were then added to this solution via a gas-tight syringe turning the solution from forest green to dark blue. Crystals grew over a two week period via vapor diffusion. From the structure determination compound 1 is an adduct of cis-tetrakis[µ-N-(phenyl)acetamidato]-κ⁴N:O;κ⁴O:N rhodium(II)] with 3-methyl benzonitrile in one axial site.

Refinement top

H-atoms were included in calculated positions with C—H = 0.93 - 0.96 and included as riding contributions with isotropic displacement parameters 1.2-1.5 times those of the attached atom. H-atoms attached to C24 are disordered across the mirror plane.

The second parameter on the SHELXL weighting line has a large value (7.37) which may arise from inadequacies in the absorption correction.

Results and discussion top

Previous papers report the structures of the related complexes 2,2-trans-Rh₂[N(C₆H₅)COCH₃]₄·2NCC₆H₅ (2) (Eagle et al., 2000), 2,2-trans-Rh₂[N(C₉H₁₁)COCH₃]₄·2NCC₆H₅ (3) (Eagle et al., 2012), 2,2-cis-[Rh₂(N(C₆H₅)COCH₃)₄]·2NCC₆H₅ (4) (Eagle et al., 2013b) and 2,2-trans-Rh₂[N(C₆H₅)COCH₃]₄·NCC₇H₇ (5) (Eagle et al., 2013a). The numbering scheme of the title compound is adopted from that of compound 2.

The axial rhodium-nitrogen-carbon bond angle for 1, 162.8 (5)° (Fig.1) is distinctly non-linear which is different from those found in compound 2 (178.5 (5)° and 169.3 (5)°), and compound 3 (180°; imposed by space group symmetry), but similar to those found in compound 4 (167.14 (15)°) and compound 5 (166.4 (4)°). The axial carbon–nitrogen bond length in 1 is 1.154 (7) Å which is comparable to corresponding distances found in 2 (1.135 (8) Å and 1.145 (8) Å) as well as 4 (1.135 (3) Å) and 5 (1.135 (3) Å) and slightly longer than 3 (1.106 (6) Å). The [Rh₂[N(C₆H₅)COCH₃)₄] portion of compound 1 has approximate -4 symmetry with non-eclipsed N_eq–Rh–Rh–O_eq torsion angles around each acetamide bridge of 0.75 (7)° or 1.99 (9)°. These can be compared to the range of 9.03° and 11.89° in 2 , 1.12 (9)° in 3, the range between 1.62 (4)° and 1.78 (4)° in 4 and 12.55 (11)° or 14.04 (8)° in 5. There are no unusually short intermolecular distances.

The infrared absorption spectum of compound 1 showed bands at 2338 cm^-1 and 2359 cm^-1 attributable to carbon–nitrogen bond stretching modes. The corresponding band for uncomplexed 3-methylbenzonitrile appears at 2228 cm^-1. This indicates that there is a shortening of the carbon–nitrogen bond and a stronger σ-interaction with the rhodium metal compared to the π-back bonding which occurs upon complexation with trans-tetrakis[µ-N-(phenyl)acetamidato]-κ⁴N:O;κ⁴O:N rhodium(II)].

Related literature top

For the synthesis and structure of four related compounds, see: Lifsey et al. (1987); Eagle et al. (2000, 2012, 2013a,b).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 2010); cell refinement: PROCESS-AUTO (Rigaku, 2010); data reduction: PROCESS-AUTO (Rigaku, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures top

Fig. 1. ORTEP of the title compound with 30% probability ellipsoids. Hydrogen atoms are drawn as small spheres.

(3-Methylbenzonitrile-1κN)-cis-tetrakis(µ-N-phenylacetamidato)-1:2κ⁴N:O;1:2κ⁴O:N-dirhodium(II)(Rh—Rh) top

Crystal data top

[Rh₂(C₈H₈NO)₄(C₈H₇N)]	F(000) = 1744.00
M_r = 859.59	D_x = 1.568 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ac 2n	Cell parameters from 27167 reflections
a = 15.3319 (14) Å	θ = 3.0–27.6°
b = 18.3248 (16) Å	µ = 0.95 mm⁻¹
c = 12.9564 (12) Å	T = 223 K
V = 3640.2 (6) Å³	Chunk, green
Z = 4	0.17 × 0.15 × 0.14 mm

Data collection top

Rigaku XtaLAB mini diffractometer	3154 reflections with I > 2σ(I)
Detector resolution: 6.849 pixels mm^-1	R_int = 0.086
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −19→19
T_min = 0.664, T_max = 0.873	k = −23→23
36328 measured reflections	l = −16→16
4292 independent reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0277P)² + 7.3733P] where P = (F_o² + 2F_c²)/3
4292 reflections	(Δ/σ)_max = 0.005
250 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Rh₂(C₈H₈NO)₄(C₈H₇N)]	V = 3640.2 (6) Å³
M_r = 859.59	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 15.3319 (14) Å	µ = 0.95 mm⁻¹
b = 18.3248 (16) Å	T = 223 K
c = 12.9564 (12) Å	0.17 × 0.15 × 0.14 mm

Data collection top

Rigaku XtaLAB mini diffractometer	4292 independent reflections
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	3154 reflections with I > 2σ(I)
T_min = 0.664, T_max = 0.873	R_int = 0.086
36328 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.05	Δρ_max = 0.75 e Å⁻³
4292 reflections	Δρ_min = −0.50 e Å⁻³
250 parameters

Special details top

Geometry. Compound 1 is coordinated by 3-methyl benzonitrile to only one axial site. In compounds 2 through 4 there are no methyl groups on the benzonitrile ligand and each of them has a benzonitrile ligand attached in each axial site. Like compound 1, compound 5 is coordinated by 3-methyl benzonitrile to only one axial site, however compound 5 exists as the trans-acetamide isomer, whereas compound 1 is the cis-acetamide isomer. The predominance of σ-bonding in the rhodium-nitrogen-carbon bond system (and lower affect of π-back bonding) is the likely cause of this deviation from linearity for compound 1, which has a similar rhodium-nitrogen-carbon angle as compound 5. The packing diagram shows that two acetamide phenyl rings on the same rhodium are stacked upon each other.

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Rh1	0.47995 (2)	0.2500	0.52236 (3)	0.02157 (11)
Rh2	0.32933 (2)	0.2500	0.46954 (3)	0.02139 (11)
O1	0.35639 (16)	0.32962 (14)	0.36333 (19)	0.0294 (6)
O2	0.44972 (15)	0.16995 (14)	0.62786 (18)	0.0254 (6)
N1	0.49816 (19)	0.33240 (17)	0.4172 (2)	0.0262 (7)
N2	0.30842 (19)	0.17003 (16)	0.5753 (2)	0.0237 (6)
N3	0.6160 (3)	0.2500	0.5704 (4)	0.0336 (11)
C1	0.4333 (2)	0.3578 (2)	0.3624 (3)	0.0273 (8)
C2	0.4427 (3)	0.4243 (2)	0.2942 (3)	0.0401 (10)
H2A	0.4958	0.4501	0.3121	0.048*
H2B	0.3930	0.4562	0.3043	0.048*
H2C	0.4453	0.4092	0.2226	0.048*
C3	0.3715 (2)	0.1440 (2)	0.6319 (3)	0.0252 (8)
C4	0.3608 (3)	0.0811 (2)	0.7052 (3)	0.0342 (9)
H4A	0.4090	0.0473	0.6966	0.041*
H4B	0.3064	0.0562	0.6908	0.041*
H4C	0.3602	0.0991	0.7756	0.041*
C5	0.5811 (2)	0.3681 (2)	0.4141 (3)	0.0283 (8)
C6	0.6393 (3)	0.3544 (2)	0.3362 (3)	0.0342 (9)
H6	0.6232	0.3231	0.2819	0.041*
C7	0.7218 (3)	0.3860 (2)	0.3363 (3)	0.0386 (10)
H7	0.7611	0.3766	0.2822	0.046*
C8	0.7452 (3)	0.4311 (2)	0.4159 (4)	0.0428 (11)
H8	0.8008	0.4527	0.4163	0.051*
C9	0.6879 (3)	0.4451 (3)	0.4957 (4)	0.0457 (11)
H9	0.7047	0.4755	0.5506	0.055*
C10	0.6056 (3)	0.4140 (2)	0.4942 (3)	0.0373 (10)
H10	0.5661	0.4240	0.5478	0.045*
C11	0.2218 (2)	0.1406 (2)	0.5787 (3)	0.0270 (8)
C12	0.1718 (3)	0.1409 (2)	0.6679 (3)	0.0344 (9)
H12	0.1944	0.1608	0.7291	0.041*
C13	0.0885 (3)	0.1117 (2)	0.6669 (4)	0.0423 (11)
H13	0.0555	0.1112	0.7280	0.051*
C14	0.0535 (3)	0.0835 (2)	0.5780 (4)	0.0464 (12)
H14	−0.0028	0.0633	0.5784	0.056*
C15	0.1015 (3)	0.0850 (2)	0.4881 (4)	0.0424 (11)
H15	0.0773	0.0668	0.4266	0.051*
C16	0.1855 (3)	0.1134 (2)	0.4879 (3)	0.0334 (9)
H16	0.2180	0.1142	0.4263	0.040*
C17	0.6913 (4)	0.2500	0.5696 (5)	0.0339 (13)
C18	0.7854 (3)	0.2500	0.5655 (5)	0.0295 (12)
C19	0.8285 (4)	0.2500	0.4693 (4)	0.0331 (13)
H19	0.7953	0.2500	0.4083	0.040*
C20	0.9168 (4)	0.2500	0.4626 (4)	0.0356 (14)
C21	0.9642 (4)	0.2500	0.5533 (4)	0.0315 (13)
H21	1.0255	0.2500	0.5501	0.038*
C22	0.9239 (4)	0.2500	0.6481 (4)	0.0354 (14)
H22	0.9578	0.2500	0.7085	0.042*
C23	0.8346 (4)	0.2500	0.6552 (4)	0.0317 (13)
H23	0.8072	0.2500	0.7200	0.038*
C24	0.9623 (5)	0.2500	0.3590 (5)	0.0500 (18)
H24A	0.9234	0.2697	0.3070	0.060*	0.5
H24B	0.9783	0.2004	0.3407	0.060*	0.5
H24C	1.0144	0.2799	0.3630	0.060*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Rh1	0.0146 (2)	0.0287 (2)	0.0214 (2)	0.000	0.00038 (16)	0.000
Rh2	0.0151 (2)	0.0283 (2)	0.0207 (2)	0.000	−0.00015 (16)	0.000
O1	0.0226 (14)	0.0381 (15)	0.0275 (13)	−0.0035 (12)	−0.0011 (11)	0.0101 (12)
O2	0.0185 (13)	0.0331 (15)	0.0245 (13)	−0.0011 (11)	0.0004 (10)	0.0033 (11)
N1	0.0205 (16)	0.0297 (17)	0.0284 (16)	−0.0020 (13)	0.0027 (13)	0.0021 (14)
N2	0.0173 (15)	0.0270 (16)	0.0267 (15)	−0.0019 (13)	−0.0004 (13)	0.0021 (14)
N3	0.018 (2)	0.040 (3)	0.043 (3)	0.000	−0.004 (2)	0.000
C1	0.025 (2)	0.034 (2)	0.0230 (18)	−0.0017 (17)	0.0019 (16)	0.0006 (16)
C2	0.031 (2)	0.044 (3)	0.045 (2)	−0.004 (2)	0.001 (2)	0.014 (2)
C3	0.0210 (19)	0.029 (2)	0.0253 (18)	−0.0006 (16)	0.0037 (15)	−0.0027 (16)
C4	0.029 (2)	0.033 (2)	0.041 (2)	−0.0041 (18)	−0.0036 (18)	0.0046 (19)
C5	0.025 (2)	0.029 (2)	0.031 (2)	−0.0025 (16)	0.0002 (16)	0.0043 (17)
C6	0.031 (2)	0.037 (2)	0.034 (2)	−0.0065 (19)	0.0060 (18)	−0.0054 (19)
C7	0.024 (2)	0.040 (2)	0.052 (3)	−0.0002 (18)	0.0121 (19)	0.000 (2)
C8	0.027 (2)	0.044 (3)	0.058 (3)	−0.008 (2)	−0.002 (2)	0.003 (2)
C9	0.044 (3)	0.048 (3)	0.046 (3)	−0.014 (2)	−0.004 (2)	−0.009 (2)
C10	0.033 (2)	0.042 (2)	0.037 (2)	−0.0073 (19)	0.0066 (18)	−0.004 (2)
C11	0.0205 (19)	0.026 (2)	0.034 (2)	0.0012 (15)	−0.0014 (16)	0.0012 (18)
C12	0.027 (2)	0.037 (2)	0.039 (2)	−0.0050 (18)	0.0002 (18)	−0.0017 (19)
C13	0.028 (2)	0.045 (3)	0.053 (3)	−0.003 (2)	0.010 (2)	0.008 (2)
C14	0.021 (2)	0.041 (3)	0.077 (3)	−0.0094 (19)	−0.001 (2)	0.007 (3)
C15	0.030 (2)	0.038 (2)	0.059 (3)	−0.0072 (19)	−0.011 (2)	−0.002 (2)
C16	0.029 (2)	0.037 (2)	0.034 (2)	−0.0027 (17)	−0.0006 (17)	−0.0021 (19)
C17	0.032 (3)	0.030 (3)	0.040 (3)	0.000	−0.006 (3)	0.000
C18	0.019 (3)	0.030 (3)	0.040 (3)	0.000	−0.004 (2)	0.000
C19	0.034 (3)	0.035 (3)	0.030 (3)	0.000	−0.007 (3)	0.000
C20	0.039 (3)	0.032 (3)	0.035 (3)	0.000	−0.001 (3)	0.000
C21	0.027 (3)	0.035 (3)	0.033 (3)	0.000	0.000 (2)	0.000
C22	0.024 (3)	0.048 (4)	0.034 (3)	0.000	−0.005 (2)	0.000
C23	0.032 (3)	0.040 (3)	0.024 (3)	0.000	0.002 (2)	0.000
C24	0.050 (4)	0.067 (5)	0.033 (3)	0.000	0.008 (3)	0.000

Geometric parameters (Å, º) top

Rh1—N1	2.053 (3)	C8—C9	1.380 (6)
Rh1—N1ⁱ	2.053 (3)	C8—H8	0.9400
Rh1—O2ⁱ	2.058 (2)	C9—C10	1.385 (6)
Rh1—O2	2.058 (2)	C9—H9	0.9400
Rh1—N3	2.177 (4)	C10—H10	0.9400
Rh1—Rh2	2.4086 (6)	C11—C12	1.387 (5)
Rh2—N2ⁱ	2.032 (3)	C11—C16	1.394 (5)
Rh2—N2	2.032 (3)	C12—C13	1.384 (5)
Rh2—O1	2.048 (2)	C12—H12	0.9400
Rh2—O1ⁱ	2.048 (2)	C13—C14	1.371 (6)
O1—C1	1.288 (4)	C13—H13	0.9400
O2—C3	1.290 (4)	C14—C15	1.378 (6)
N1—C1	1.308 (5)	C14—H14	0.9400
N1—C5	1.431 (5)	C15—C16	1.389 (5)
N2—C3	1.304 (5)	C15—H15	0.9400
N2—C11	1.434 (4)	C16—H16	0.9400
N3—C17	1.154 (7)	C17—C18	1.444 (8)
C1—C2	1.511 (5)	C18—C23	1.385 (7)
C2—H2A	0.9700	C18—C19	1.411 (8)
C2—H2B	0.9700	C19—C20	1.356 (8)
C2—H2C	0.9700	C19—H19	0.9400
C3—C4	1.503 (5)	C20—C21	1.381 (8)
C4—H4A	0.9700	C20—C24	1.513 (8)
C4—H4B	0.9700	C21—C22	1.375 (8)
C4—H4C	0.9700	C21—H21	0.9400
C5—C6	1.370 (5)	C22—C23	1.372 (8)
C5—C10	1.387 (5)	C22—H22	0.9400
C6—C7	1.392 (5)	C23—H23	0.9400
C6—H6	0.9400	C24—H24A	0.9700
C7—C8	1.370 (6)	C24—H24B	0.9700
C7—H7	0.9400	C24—H24C	0.9700

N1—Rh1—N1ⁱ	94.72 (17)	C7—C6—H6	119.5
N1—Rh1—O2ⁱ	86.96 (11)	C8—C7—C6	119.3 (4)
N1ⁱ—Rh1—O2ⁱ	174.72 (11)	C8—C7—H7	120.3
N1—Rh1—O2	174.72 (11)	C6—C7—H7	120.3
N1ⁱ—Rh1—O2	86.96 (11)	C7—C8—C9	120.7 (4)
O2ⁱ—Rh1—O2	90.92 (14)	C7—C8—H8	119.7
N1—Rh1—N3	93.41 (12)	C9—C8—H8	119.7
N1ⁱ—Rh1—N3	93.41 (12)	C8—C9—C10	119.5 (4)
O2ⁱ—Rh1—N3	91.48 (11)	C8—C9—H9	120.2
O2—Rh1—N3	91.48 (11)	C10—C9—H9	120.2
N1—Rh1—Rh2	86.66 (8)	C9—C10—C5	120.4 (4)
N1ⁱ—Rh1—Rh2	86.66 (8)	C9—C10—H10	119.8
O2ⁱ—Rh1—Rh2	88.44 (7)	C5—C10—H10	119.8
O2—Rh1—Rh2	88.44 (7)	C12—C11—C16	118.9 (3)
N3—Rh1—Rh2	179.89 (13)	C12—C11—N2	122.5 (3)
N2ⁱ—Rh2—N2	92.30 (17)	C16—C11—N2	118.6 (3)
N2ⁱ—Rh2—O1	88.36 (11)	C13—C12—C11	120.1 (4)
N2—Rh2—O1	177.38 (11)	C13—C12—H12	120.0
N2ⁱ—Rh2—O1ⁱ	177.38 (11)	C11—C12—H12	120.0
N2—Rh2—O1ⁱ	88.36 (11)	C14—C13—C12	121.0 (4)
O1—Rh2—O1ⁱ	90.86 (15)	C14—C13—H13	119.5
N2ⁱ—Rh2—Rh1	87.68 (8)	C12—C13—H13	119.5
N2—Rh2—Rh1	87.68 (8)	C13—C14—C15	119.6 (4)
O1—Rh2—Rh1	89.81 (7)	C13—C14—H14	120.2
O1ⁱ—Rh2—Rh1	89.81 (7)	C15—C14—H14	120.2
C1—O1—Rh2	118.6 (2)	C14—C15—C16	120.3 (4)
C3—O2—Rh1	119.9 (2)	C14—C15—H15	119.9
C1—N1—C5	119.8 (3)	C16—C15—H15	119.9
C1—N1—Rh1	121.3 (2)	C15—C16—C11	120.1 (4)
C5—N1—Rh1	118.4 (2)	C15—C16—H16	119.9
C3—N2—C11	122.2 (3)	C11—C16—H16	119.9
C3—N2—Rh2	121.7 (2)	N3—C17—C18	178.5 (7)
C11—N2—Rh2	116.0 (2)	C23—C18—C19	119.0 (5)
C17—N3—Rh1	162.8 (5)	C23—C18—C17	120.9 (5)
O1—C1—N1	123.2 (3)	C19—C18—C17	120.0 (5)
O1—C1—C2	114.6 (3)	C20—C19—C18	121.6 (5)
N1—C1—C2	122.2 (3)	C20—C19—H19	119.2
C1—C2—H2A	109.5	C18—C19—H19	119.2
C1—C2—H2B	109.5	C19—C20—C21	118.1 (6)
H2A—C2—H2B	109.5	C19—C20—C24	121.1 (6)
C1—C2—H2C	109.5	C21—C20—C24	120.8 (5)
H2A—C2—H2C	109.5	C22—C21—C20	121.5 (5)
H2B—C2—H2C	109.5	C22—C21—H21	119.2
O2—C3—N2	122.1 (3)	C20—C21—H21	119.2
O2—C3—C4	114.2 (3)	C23—C22—C21	120.6 (5)
N2—C3—C4	123.7 (3)	C23—C22—H22	119.7
C3—C4—H4A	109.5	C21—C22—H22	119.7
C3—C4—H4B	109.5	C22—C23—C18	119.2 (5)
H4A—C4—H4B	109.5	C22—C23—H23	120.4
C3—C4—H4C	109.5	C18—C23—H23	120.4
H4A—C4—H4C	109.5	C20—C24—H24A	109.5
H4B—C4—H4C	109.5	C20—C24—H24B	109.5
C6—C5—C10	119.1 (4)	H24A—C24—H24B	109.5
C6—C5—N1	121.0 (4)	C20—C24—H24C	109.5
C10—C5—N1	119.8 (3)	H24A—C24—H24C	109.5
C5—C6—C7	121.0 (4)	H24B—C24—H24C	109.5
C5—C6—H6	119.5

Rh2—O1—C1—N1	8.4 (5)	N1—C5—C10—C9	175.7 (4)
Rh2—O1—C1—C2	−170.2 (2)	C3—N2—C11—C12	61.3 (5)
C5—N1—C1—O1	−178.2 (3)	Rh2—N2—C11—C12	−122.9 (3)
Rh1—N1—C1—O1	−6.1 (5)	C3—N2—C11—C16	−121.2 (4)
C5—N1—C1—C2	0.3 (5)	Rh2—N2—C11—C16	54.6 (4)
Rh1—N1—C1—C2	172.4 (3)	C16—C11—C12—C13	2.6 (6)
Rh1—O2—C3—N2	−4.4 (5)	N2—C11—C12—C13	−179.9 (4)
Rh1—O2—C3—C4	174.4 (2)	C11—C12—C13—C14	−1.3 (7)
C11—N2—C3—O2	179.1 (3)	C12—C13—C14—C15	−0.8 (7)
Rh2—N2—C3—O2	3.6 (5)	C13—C14—C15—C16	1.4 (7)
C11—N2—C3—C4	0.4 (5)	C14—C15—C16—C11	−0.1 (6)
Rh2—N2—C3—C4	−175.1 (3)	C12—C11—C16—C15	−1.9 (6)
C1—N1—C5—C6	−82.5 (5)	N2—C11—C16—C15	−179.5 (4)
Rh1—N1—C5—C6	105.1 (4)	C23—C18—C19—C20	0.000 (1)
C1—N1—C5—C10	101.5 (4)	C17—C18—C19—C20	180.000 (1)
Rh1—N1—C5—C10	−70.9 (4)	C18—C19—C20—C21	0.000 (1)
C10—C5—C6—C7	−0.4 (6)	C18—C19—C20—C24	180.000 (1)
N1—C5—C6—C7	−176.4 (4)	C19—C20—C21—C22	0.000 (1)
C5—C6—C7—C8	0.5 (7)	C24—C20—C21—C22	180.000 (1)
C6—C7—C8—C9	0.1 (7)	C20—C21—C22—C23	0.000 (1)
C7—C8—C9—C10	−0.9 (7)	C21—C22—C23—C18	0.000 (1)
C8—C9—C10—C5	1.1 (7)	C19—C18—C23—C22	0.000 (1)
C6—C5—C10—C9	−0.4 (6)	C17—C18—C23—C22	180.000 (1)

Symmetry code: (i) x, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Rh₂(C₈H₈NO)₄(C₈H₇N)]
M_r	859.59
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	223
a, b, c (Å)	15.3319 (14), 18.3248 (16), 12.9564 (12)
V (Å³)	3640.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.17 × 0.15 × 0.14

Data collection
Diffractometer	Rigaku XtaLAB mini diffractometer
Absorption correction	Multi-scan (REQAB; Rigaku, 1998)
T_min, T_max	0.664, 0.873
No. of measured, independent and observed [I > 2σ(I)] reflections	36328, 4292, 3154
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.089, 1.05
No. of reflections	4292
No. of parameters	250
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.50

Computer programs: PROCESS-AUTO (Rigaku, 2010), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010).

Acknowledgements

We thank Dr Lee Daniels of Rigaku Americas for his training on the Rigaku XtaLAB diffractometer and his extended help in the completion of the structural determination. Support was provided by a Start Up Grant from ETSU. We thank Johnson Matthey for their generous loan of rhodium trichloride.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Eagle, C. T., Atem-Tambe, N., Kpogo, K. K., Tan, J. & Quarshie, F. (2013a). Acta Cryst. E69, m639. CSD CrossRef IUCr Journals Google Scholar
Eagle, C. T., Farrar, D. G., Holder, G. N., Pennington, W. T. & Bailey, R. D. (2000). J. Organomet. Chem. 596, 90–94. Web of Science CrossRef CAS Google Scholar
Eagle, C. T., Kpogo, K. K., Zink, L. C. & Smith, A. E. (2012). Acta Cryst. E68, m877. CSD CrossRef IUCr Journals Google Scholar
Eagle, C. T., Quarshie, F., Ketron, M. E. & Atem-Tambe, N. (2013b). Acta Cryst. E69, m329. CSD CrossRef IUCr Journals Google Scholar
Lifsey, R. S., Lin, X. Q., Chavan, M. Y., Ahsan, M. Q., Kadish, K. M. & Bear, J. L. (1987). Inorg. Chem. 26, 830–836. CSD CrossRef CAS Web of Science Google Scholar
Rigaku (1998). REQAB. Rigaku Americas, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2010). CrystalStructure and PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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