Chemistry of transition-metal com­plexes containing functionalized phosphines: synthesis and structural analysis of rhodium(I) com­plexes containing allyl and cyano­alkylphosphines

A series of related acetyl­acetonate–carbon­yl–rhodium com­pounds substituted by functionalized phosphines has been prepared in good to excellent yields by the reaction of [Rh(acac)(CO)₂] (acac is acetyl­acetonate) with the corresponding allyl-, cyano­methyl- or cyano­ethyl-substituted phosphines. All com­pounds were fully characterized by ³¹P, ¹H, ¹³C NMR and IR spectroscopy. The X-ray structures of (acetyl­acetonato-κ²O,O′)(tert-butyl­phosphanedicarbo­nitrile-κP)carbonyl­rhodium(I), [Rh(C₅H₇O₂)(CO)(C₈H₁₃N₂)] or [Rh(acac)(CO)(^tBuP(CH₂CN)₂}] (2b), (acetyl­acetonato-κ²O,O′)carbon­yl[3-(di­phenyl­phosphan­yl)propane­nitrile-κP]rhodium(I), [Rh(C₅H₇O₂)(C₁₅H₁₄N)(CO)] or [Rh(acac)(CO){Ph₂P(CH₂CH₂CN)}] (2h), and (acetyl­acetonato-κ²O,O′)carbonyl[3-(di-tert-butyl­phosphan­yl)propane­nitrile-κP]rhodium(I), [Rh(C₅H₇O₂)(C₁₁H₂₂N)(CO)] or [Rh(acac)(CO){^tBu₂P(CH₂CH₂CN)}] (2i), showed a square-planar geometry around the Rh atom with a significant trans influence over the acetyl­acetonate moiety, evidenced by long Rh—O bond lengths as expected for poor π-acceptor phosphines. The Rh—P distances displayed an inverse linear dependence with the coupling constants J_P-Rh and the IR ν(C[triple bond]O) bands, which accounts for the Rh—P electronic bonding feature (poor π-acceptors) of these com­plexes. A combined study from density functional theory (DFT) calculations and an evaluation of the intra­molecular H...Rh contacts from X-ray diffraction data allowed a com­parison of the conformational preferences of these com­plexes in the solid state versus the isolated com­pounds in the gas phase. For 2b, 2h and 2i, an energy-framework study evidenced that the crystal structures are mainly governed by dispersive energy. In fact, strong pairwise mol­ecular dispersive inter­actions are responsible for the columnar arrangement observed in these com­plexes. A Hirshfeld surface analysis employing three-dimensional mol­ecular surface contours and two-dimensional fingerprint plots indicated that the structures are stabilized by H...H, C...H, H...O, H...N and H...Rh inter­molecular inter­actions.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991) for (2b); CrystalClear (Rigaku/MSC, 2005) for (2h), (2i). Cell refinement: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991) for (2b); CrystalClear (Rigaku/MSC, 2005) for (2h), (2i). Data reduction: TEXSAN (Molecular Structure Corporation, 1999) for (2b); CrystalClear (Rigaku/MSC, 2005) for (2h), (2i). For all structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).

(Acetylacetonato-κ²O,O')(tert-butylphosphanedicarbonitrile-κP)carbonylrhodium(I) (2b)

Crystal data

[Rh(C5H7O2)(CO)(C8H13N2)]	Dx = 1.519 Mg m^−3
Mr = 398.20	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 11.972 (4) Å	θ = 28–36°
b = 12.032 (5) Å	µ = 1.08 mm^−1
c = 12.085 (5) Å	T = 298 K
V = 1740.8 (11) Å^3	Prism
Z = 4	0.36 × 0.34 × 0.30 mm
F(000) = 808

Data collection

Rigaku AFC7S diffractometer	2724 reflections with I > 2σ(I)
Radiation source: Normal-focus sealed tube	Rint = 0.050
ω–2θ scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: ψ scan (North et al., 1968)	h = −3→14
Tmin = 0.655, Tmax = 0.714	k = −4→14
4245 measured reflections	l = −4→14
2835 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.026	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 0.6003P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.074	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.61 e Å^−3
2835 reflections	Δρmin = −0.78 e Å^−3
190 parameters	Absolute structure: Flack x determined using 1013 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004).
0 restraints	Absolute structure parameter: −0.03 (4)

Special details

Experimental. 3 standard reflection, every 150 reflection, decay: none

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Rh1	0.39711 (3)	0.27288 (3)	0.17779 (3)	0.04056 (14)
P1	0.40942 (10)	0.37160 (10)	0.33244 (10)	0.0375 (3)
O1	0.5060 (3)	0.3797 (3)	0.1045 (3)	0.0523 (9)
O2	0.3837 (4)	0.1863 (3)	0.0316 (3)	0.0549 (9)
O3	0.2458 (5)	0.1175 (5)	0.2916 (4)	0.0829 (15)
N1	0.4814 (6)	0.3748 (7)	0.6386 (5)	0.092 (2)
N2	0.7008 (5)	0.3071 (6)	0.3924 (6)	0.089 (2)
C1	0.5362 (5)	0.3781 (5)	0.0018 (4)	0.0486 (13)
C2	0.4984 (5)	0.3044 (5)	−0.0767 (4)	0.0540 (14)
H2	0.5235	0.3161	−0.1486	0.065*
C3	0.4272 (5)	0.2147 (5)	−0.0616 (4)	0.0521 (13)
C4	0.6169 (7)	0.4666 (6)	−0.0292 (5)	0.0712 (17)
H4A	0.6340	0.5109	0.0347	0.107*
H4B	0.5848	0.5130	−0.0854	0.107*
H4C	0.6842	0.4332	−0.0568	0.107*
C5	0.3956 (8)	0.1442 (6)	−0.1578 (5)	0.082 (2)
H5A	0.3457	0.0866	−0.1337	0.123*
H5B	0.4614	0.1114	−0.1892	0.123*
H5C	0.3591	0.1892	−0.2125	0.123*
C6	0.3034 (5)	0.1782 (5)	0.2471 (5)	0.0543 (13)
C7	0.3031 (5)	0.4820 (5)	0.3522 (5)	0.0576 (14)
C8	0.3136 (7)	0.5450 (8)	0.4614 (6)	0.092 (3)
H8A	0.2562	0.6006	0.4656	0.138*
H8B	0.3855	0.5801	0.4650	0.138*
H8C	0.3057	0.4942	0.5221	0.138*
C9	0.1889 (6)	0.4288 (8)	0.3372 (9)	0.102 (3)
H9A	0.1319	0.4841	0.3465	0.153*
H9B	0.1791	0.3713	0.3913	0.153*
H9C	0.1837	0.3975	0.2643	0.153*
C10	0.3211 (8)	0.5646 (6)	0.2567 (6)	0.089 (2)
H10A	0.2680	0.6241	0.2626	0.133*
H10B	0.3111	0.5270	0.1873	0.133*
H10C	0.3955	0.5942	0.2606	0.133*
C11	0.4086 (5)	0.2847 (5)	0.4581 (4)	0.0553 (14)
H11A	0.3327	0.2599	0.4709	0.066*
H11B	0.4536	0.2192	0.4439	0.066*
C12	0.4493 (6)	0.3365 (6)	0.5595 (5)	0.0652 (17)
C13	0.5445 (4)	0.4448 (5)	0.3435 (4)	0.0467 (12)
H13A	0.5609	0.4816	0.2739	0.056*
H13B	0.5397	0.5013	0.4005	0.056*
C14	0.6331 (5)	0.3689 (6)	0.3697 (5)	0.0570 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh1	0.0443 (2)	0.0422 (2)	0.03527 (19)	−0.00320 (18)	−0.00025 (17)	0.00016 (17)
P1	0.0373 (6)	0.0417 (6)	0.0336 (5)	0.0001 (5)	0.0005 (6)	0.0028 (5)
O1	0.061 (2)	0.055 (2)	0.0410 (18)	−0.0129 (19)	0.0063 (17)	−0.0039 (18)
O2	0.075 (2)	0.0479 (18)	0.0421 (18)	−0.012 (2)	−0.003 (2)	−0.0014 (16)
O3	0.082 (3)	0.082 (3)	0.085 (3)	−0.034 (3)	0.013 (3)	0.007 (3)
N1	0.113 (5)	0.118 (6)	0.045 (3)	−0.019 (5)	−0.016 (3)	0.011 (3)
N2	0.056 (3)	0.109 (5)	0.103 (5)	0.017 (4)	−0.021 (3)	−0.008 (4)
C1	0.053 (3)	0.052 (3)	0.041 (3)	0.000 (3)	0.010 (2)	0.003 (2)
C2	0.073 (4)	0.056 (3)	0.034 (2)	0.005 (3)	0.004 (2)	0.001 (2)
C3	0.069 (3)	0.050 (3)	0.038 (3)	0.004 (3)	−0.006 (2)	0.000 (2)
C4	0.090 (5)	0.068 (4)	0.055 (3)	−0.013 (4)	0.019 (4)	−0.002 (3)
C5	0.121 (6)	0.077 (4)	0.048 (3)	−0.004 (5)	−0.009 (4)	−0.015 (3)
C6	0.055 (3)	0.055 (3)	0.053 (3)	−0.013 (3)	−0.002 (3)	0.002 (3)
C7	0.051 (3)	0.062 (3)	0.059 (3)	0.016 (3)	−0.006 (3)	−0.008 (3)
C8	0.093 (5)	0.113 (7)	0.071 (4)	0.044 (5)	−0.005 (4)	−0.032 (5)
C9	0.046 (3)	0.106 (6)	0.154 (8)	0.022 (4)	0.002 (5)	−0.010 (7)
C10	0.112 (6)	0.072 (4)	0.083 (5)	0.038 (5)	−0.021 (5)	0.009 (4)
C11	0.059 (3)	0.064 (3)	0.042 (3)	−0.011 (3)	−0.001 (3)	0.011 (3)
C12	0.069 (4)	0.084 (5)	0.043 (3)	−0.010 (4)	0.000 (3)	0.020 (3)
C13	0.048 (3)	0.047 (3)	0.045 (3)	−0.009 (2)	0.001 (2)	0.001 (2)
C14	0.040 (3)	0.076 (4)	0.055 (3)	−0.005 (3)	−0.004 (2)	−0.006 (3)

Geometric parameters (Å, º)

Rh1—C6	1.805 (6)	C5—H5B	0.9600
Rh1—O1	2.033 (4)	C5—H5C	0.9600
Rh1—O2	2.057 (4)	C7—C9	1.520 (10)
Rh1—P1	2.2194 (14)	C7—C8	1.528 (9)
P1—C11	1.843 (5)	C7—C10	1.539 (9)
P1—C13	1.846 (5)	C8—H8A	0.9600
P1—C7	1.855 (6)	C8—H8B	0.9600
O1—C1	1.294 (6)	C8—H8C	0.9599
O2—C3	1.287 (7)	C9—H9A	0.9600
O3—C6	1.140 (7)	C9—H9B	0.9600
N1—C12	1.129 (9)	C9—H9C	0.9600
N2—C14	1.133 (9)	C10—H10A	0.9599
C1—C2	1.375 (8)	C10—H10B	0.9600
C1—C4	1.486 (9)	C10—H10C	0.9601
C2—C3	1.388 (8)	C11—C12	1.458 (9)
C2—H2	0.9301	C11—H11A	0.9701
C3—C5	1.488 (8)	C11—H11B	0.9701
C4—H4A	0.9601	C13—C14	1.435 (8)
C4—H4B	0.9601	C13—H13A	0.9700
C4—H4C	0.9599	C13—H13B	0.9698
C5—H5A	0.9600
C6—Rh1—O1	178.0 (2)	C9—C7—C10	108.0 (6)
C6—Rh1—O2	91.7 (2)	C8—C7—C10	108.4 (6)
O1—Rh1—O2	89.78 (15)	C9—C7—P1	107.5 (5)
C6—Rh1—P1	89.33 (18)	C8—C7—P1	114.2 (4)
O1—Rh1—P1	89.18 (11)	C10—C7—P1	105.6 (4)
O2—Rh1—P1	177.97 (11)	C7—C8—H8A	109.5
C11—P1—C13	102.4 (3)	C7—C8—H8B	109.4
C11—P1—C7	107.2 (3)	H8A—C8—H8B	109.5
C13—P1—C7	104.5 (3)	C7—C8—H8C	109.6
C11—P1—Rh1	112.9 (2)	H8A—C8—H8C	109.5
C13—P1—Rh1	111.98 (18)	H8B—C8—H8C	109.5
C7—P1—Rh1	116.48 (18)	C7—C9—H9A	109.5
C1—O1—Rh1	126.0 (4)	C7—C9—H9B	109.4
C3—O2—Rh1	125.9 (3)	H9A—C9—H9B	109.5
O1—C1—C2	125.4 (5)	C7—C9—H9C	109.5
O1—C1—C4	114.4 (5)	H9A—C9—H9C	109.5
C2—C1—C4	120.2 (5)	H9B—C9—H9C	109.5
C1—C2—C3	127.8 (5)	C7—C10—H10A	109.5
C1—C2—H2	116.1	C7—C10—H10B	109.5
C3—C2—H2	116.1	H10A—C10—H10B	109.5
O2—C3—C2	124.8 (5)	C7—C10—H10C	109.5
O2—C3—C5	115.5 (6)	H10A—C10—H10C	109.5
C2—C3—C5	119.8 (5)	H10B—C10—H10C	109.5
C1—C4—H4A	109.5	C12—C11—P1	116.6 (4)
C1—C4—H4B	109.5	C12—C11—H11A	108.1
H4A—C4—H4B	109.5	P1—C11—H11A	108.1
C1—C4—H4C	109.4	C12—C11—H11B	108.1
H4A—C4—H4C	109.5	P1—C11—H11B	108.2
H4B—C4—H4C	109.5	H11A—C11—H11B	107.3
C3—C5—H5A	109.5	N1—C12—C11	178.8 (8)
C3—C5—H5B	109.5	C14—C13—P1	111.1 (4)
H5A—C5—H5B	109.5	C14—C13—H13A	109.4
C3—C5—H5C	109.5	P1—C13—H13A	109.4
H5A—C5—H5C	109.5	C14—C13—H13B	109.5
H5B—C5—H5C	109.5	P1—C13—H13B	109.5
O3—C6—Rh1	178.9 (6)	H13A—C13—H13B	108.0
C9—C7—C8	112.7 (6)	N2—C14—C13	177.9 (7)

(Acetylacetonato-κ²O,O')]carbonyl[3-(diphenylphosphanyl)propanenitrile-κPrhodium(I), (2h)

Crystal data

[Rh(C5H7O2)(C15H14NP)(CO)]	F(000) = 952
Mr = 469.27	Dx = 1.459 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.676 (4) Å	Cell parameters from 23386 reflections
b = 15.666 (4) Å	θ = 2–25°
c = 11.937 (4) Å	µ = 0.89 mm^−1
β = 101.927 (8)°	T = 298 K
V = 2136.4 (11) Å^3	Block, yellow
Z = 4	0.50 × 0.45 × 0.35 mm

Data collection

Rigaku AFC-7S Mercury diffractometer	4343 independent reflections
Radiation source: fine-focus seal tube	3661 reflections with I > 2σ(I)
Detector resolution: 14.6306 pixels mm^-1	Rint = 0.029
ω scans	θmax = 28.1°, θmin = 2.2°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −13→13
Tmin = 0.642, Tmax = 0.733	k = −16→19
23386 measured reflections	l = −14→14

Refinement

Refinement on F^2	104 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0421P)^2 + 1.0006P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.002
4343 reflections	Δρmax = 0.74 e Å^−3
301 parameters	Δρmin = −0.61 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Intensity data were recorded at room temperature on a Rigaku AFC-7S diffractometer using monochromated Mo Kα radiation (λ= 0.71073 Å). The apparatus was configured with a fine-focus sealed tube and a scintillator detector for data collection of 2b and a CCD mercury detector for 2h and 2i. Experimental details on unit cell and intensity measurements can be found in the CIF files deposited with the Cambridge Crystallographic Data Centre [CCDC 793226, 793227, 793228]. Crystal data, intensity data collection parameters, and final refinement results are summarized in Table 1. For 2h and 2i, an empirical absorption correction multi-scan was applied to data using the CrystalClear crystallographic software package ?(CrystalClear, 2005)?. For 2b, a semiempirical psi-scan absorption correction was applied ?(North et al., 1968). The structures were solved by Direct Methods and refined by full-matrix least-squares on F².

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Rh1	0.74701 (2)	0.20421 (2)	0.10036 (2)	0.04352 (10)
P1	0.78345 (6)	0.17911 (4)	0.28775 (6)	0.03969 (16)
O2	0.7114 (2)	0.22219 (15)	−0.07578 (18)	0.0607 (6)
O1	0.80710 (19)	0.08437 (13)	0.07647 (17)	0.0578 (5)
O3	0.6495 (3)	0.37253 (17)	0.1389 (3)	0.1012 (10)
N1	1.1467 (3)	−0.0185 (3)	0.3857 (3)	0.1013 (13)
C7	0.8542 (2)	0.26134 (17)	0.3849 (2)	0.0442 (6)
C8	0.9039 (3)	0.33200 (19)	0.3434 (3)	0.0570 (8)
H8	0.8952	0.3397	0.2649	0.068*
C9	0.9663 (3)	0.3909 (2)	0.4180 (4)	0.0762 (11)
H9	1.0008	0.4376	0.3897	0.091*
C10	0.9773 (3)	0.3805 (2)	0.5336 (4)	0.0843 (13)
H10	1.0184	0.4206	0.5837	0.101*
C11	0.9281 (3)	0.3113 (2)	0.5761 (3)	0.0734 (11)
H11	0.9356	0.3050	0.6548	0.088*
C12	0.8674 (3)	0.2509 (2)	0.5025 (3)	0.0558 (7)
H12	0.8355	0.2035	0.5316	0.067*
C13	0.8808 (3)	0.08754 (17)	0.3320 (3)	0.0492 (7)
H13A	0.8488	0.0375	0.2761	0.074*
H13B	0.8860	0.0725	0.4170	0.074*
C14	1.0051 (3)	0.1070 (2)	0.3150 (3)	0.0583 (8)
H14B	1.0469	0.1621	0.3511	0.088*
H14A	1.0021	0.1126	0.2260	0.088*
C15	1.0855 (3)	0.0363 (2)	0.3546 (3)	0.0686 (9)
C3	0.7231 (3)	0.1658 (3)	−0.1494 (3)	0.0647 (9)
C2	0.7654 (3)	0.0836 (3)	−0.1261 (3)	0.0706 (10)
H2	0.7689	0.0494	−0.1890	0.085*
C1	0.8029 (3)	0.0471 (2)	−0.0195 (3)	0.0592 (8)
C6	0.6884 (3)	0.3077 (2)	0.1246 (3)	0.0613 (8)
C4	0.8444 (4)	−0.0439 (2)	−0.0091 (4)	0.0852 (12)
H4A	0.8500	−0.0650	−0.0833	0.128*
H4B	0.7897	−0.0781	0.0213	0.128*
H4C	0.9198	−0.0466	0.0413	0.128*
C5	0.6887 (4)	0.1951 (3)	−0.2720 (3)	0.0945 (14)
H5A	0.7354	0.2435	−0.2835	0.142*
H5B	0.6075	0.2109	−0.2886	0.142*
H5C	0.7013	0.1496	−0.3220	0.142*
C16A	0.6522 (12)	0.1593 (10)	0.3447 (16)	0.046 (3)	0.53 (3)
C17A	0.5929 (12)	0.2284 (10)	0.3791 (17)	0.051 (3)	0.53 (3)
H17A	0.6226	0.2833	0.3767	0.061*	0.53 (3)
C18A	0.4895 (10)	0.2156 (13)	0.4168 (11)	0.061 (3)	0.53 (3)
H18A	0.4524	0.2614	0.4438	0.073*	0.53 (3)
C19A	0.4421 (9)	0.1361 (15)	0.4142 (10)	0.066 (3)	0.53 (3)
H19A	0.3718	0.1286	0.4380	0.079*	0.53 (3)
C20A	0.4965 (12)	0.0654 (10)	0.3767 (13)	0.069 (3)	0.53 (3)
H20A	0.4636	0.0113	0.3755	0.083*	0.53 (3)
C21A	0.6016 (14)	0.0785 (10)	0.3413 (17)	0.055 (3)	0.53 (3)
H21A	0.6387	0.0324	0.3148	0.066*	0.53 (3)
C16B	0.6538 (12)	0.1456 (13)	0.3384 (16)	0.043 (3)	0.47 (3)
C17B	0.5876 (15)	0.2031 (13)	0.3849 (19)	0.054 (3)	0.47 (3)
H17B	0.6135	0.2592	0.3961	0.065*	0.47 (3)
C18B	0.4829 (11)	0.1800 (15)	0.4155 (12)	0.061 (3)	0.47 (3)
H18B	0.4381	0.2197	0.4455	0.074*	0.47 (3)
C19B	0.4486 (11)	0.0969 (17)	0.4000 (12)	0.064 (4)	0.47 (3)
H19B	0.3789	0.0799	0.4196	0.077*	0.47 (3)
C20B	0.5146 (14)	0.0373 (14)	0.3559 (16)	0.073 (4)	0.47 (3)
H20B	0.4886	−0.0188	0.3456	0.087*	0.47 (3)
C21B	0.6188 (15)	0.0606 (12)	0.327 (2)	0.056 (3)	0.47 (3)
H21B	0.6649	0.0200	0.3006	0.067*	0.47 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh1	0.05160 (16)	0.04385 (15)	0.03655 (14)	−0.00244 (9)	0.01242 (10)	−0.00134 (8)
P1	0.0429 (4)	0.0402 (3)	0.0364 (4)	−0.0009 (3)	0.0093 (3)	−0.0016 (3)
O2	0.0707 (15)	0.0772 (14)	0.0360 (11)	−0.0047 (11)	0.0156 (10)	0.0020 (10)
O1	0.0692 (14)	0.0551 (12)	0.0505 (12)	0.0037 (10)	0.0156 (10)	−0.0105 (9)
O3	0.136 (3)	0.0571 (15)	0.104 (2)	0.0380 (16)	0.0112 (19)	−0.0034 (14)
N1	0.107 (3)	0.117 (3)	0.086 (2)	0.062 (2)	0.032 (2)	0.018 (2)
C7	0.0381 (14)	0.0458 (15)	0.0470 (16)	0.0028 (11)	0.0052 (12)	−0.0084 (12)
C8	0.0522 (18)	0.0448 (16)	0.070 (2)	−0.0017 (13)	0.0040 (15)	−0.0026 (14)
C9	0.067 (2)	0.0486 (19)	0.101 (3)	−0.0068 (15)	−0.010 (2)	−0.0077 (18)
C10	0.078 (3)	0.062 (2)	0.093 (3)	0.0078 (18)	−0.029 (2)	−0.029 (2)
C11	0.073 (2)	0.078 (2)	0.056 (2)	0.0130 (19)	−0.0163 (18)	−0.0198 (17)
C12	0.0550 (18)	0.064 (2)	0.0444 (17)	0.0053 (14)	0.0007 (13)	−0.0047 (13)
C13	0.0592 (18)	0.0413 (15)	0.0487 (16)	0.0041 (12)	0.0145 (13)	0.0026 (12)
C14	0.0506 (17)	0.0617 (19)	0.064 (2)	0.0124 (14)	0.0159 (15)	0.0083 (15)
C15	0.068 (2)	0.085 (2)	0.056 (2)	0.0253 (19)	0.0202 (17)	−0.0003 (17)
C3	0.058 (2)	0.095 (3)	0.0448 (18)	−0.0100 (18)	0.0192 (15)	−0.0072 (17)
C2	0.072 (2)	0.090 (3)	0.054 (2)	−0.0025 (19)	0.0221 (17)	−0.0250 (18)
C1	0.0506 (18)	0.067 (2)	0.063 (2)	−0.0069 (14)	0.0199 (15)	−0.0211 (16)
C6	0.076 (2)	0.0571 (19)	0.0480 (19)	0.0058 (16)	0.0059 (16)	0.0052 (14)
C4	0.091 (3)	0.064 (2)	0.104 (3)	0.0005 (19)	0.029 (2)	−0.031 (2)
C5	0.117 (4)	0.126 (4)	0.042 (2)	0.007 (3)	0.019 (2)	−0.006 (2)
C16A	0.046 (5)	0.056 (5)	0.035 (6)	−0.001 (3)	0.008 (4)	0.001 (4)
C17A	0.042 (4)	0.059 (6)	0.052 (5)	−0.002 (4)	0.013 (3)	−0.004 (5)
C18A	0.043 (4)	0.075 (7)	0.067 (5)	0.001 (4)	0.018 (3)	−0.003 (5)
C19A	0.053 (4)	0.077 (8)	0.070 (5)	−0.005 (5)	0.019 (4)	0.001 (5)
C20A	0.068 (6)	0.065 (7)	0.080 (7)	−0.005 (4)	0.030 (4)	0.008 (5)
C21A	0.062 (5)	0.053 (5)	0.054 (6)	0.002 (4)	0.020 (4)	0.004 (4)
C16B	0.039 (5)	0.059 (6)	0.028 (6)	−0.005 (4)	−0.001 (4)	0.002 (4)
C17B	0.049 (4)	0.060 (7)	0.055 (5)	−0.006 (4)	0.013 (4)	0.008 (6)
C18B	0.047 (5)	0.071 (9)	0.068 (5)	−0.005 (5)	0.017 (4)	0.008 (6)
C19B	0.052 (5)	0.077 (9)	0.065 (6)	−0.015 (5)	0.016 (4)	0.009 (6)
C20B	0.059 (5)	0.081 (8)	0.082 (7)	−0.019 (5)	0.024 (4)	0.004 (6)
C21B	0.051 (5)	0.056 (6)	0.063 (7)	−0.015 (4)	0.017 (4)	0.004 (5)

Geometric parameters (Å, º)

Rh1—C6	1.807 (3)	C3—C5	1.507 (5)
Rh1—O1	2.045 (2)	C2—C1	1.381 (5)
Rh1—O2	2.076 (2)	C2—H2	0.9300
Rh1—P1	2.2240 (10)	C1—C4	1.502 (5)
Rh1—H14A	3.3668	C4—H4A	0.9600
Rh1—H13A	3.4068	C4—H4B	0.9600
P1—C7	1.814 (3)	C4—H4C	0.9600
P1—C16B	1.820 (9)	C5—H5A	0.9600
P1—C16A	1.828 (9)	C5—H5B	0.9600
P1—C13	1.839 (3)	C5—H5C	0.9600
O2—C3	1.273 (4)	C16A—C17A	1.392 (10)
O1—C1	1.278 (4)	C16A—C21A	1.394 (10)
O3—C6	1.139 (4)	C17A—C18A	1.388 (10)
N1—C15	1.130 (4)	C17A—H17A	0.9300
C7—C8	1.388 (4)	C18A—C19A	1.360 (11)
C7—C12	1.391 (4)	C18A—H18A	0.9300
C8—C9	1.381 (4)	C19A—C20A	1.394 (11)
C8—H8	0.9300	C19A—H19A	0.9300
C9—C10	1.369 (6)	C20A—C21A	1.394 (10)
C9—H9	0.9300	C20A—H20A	0.9300
C10—C11	1.373 (6)	C21A—H21A	0.9300
C10—H10	0.9300	C16B—C17B	1.376 (11)
C11—C12	1.382 (4)	C16B—C21B	1.392 (11)
C11—H11	0.9300	C17B—C18B	1.395 (11)
C12—H12	0.9300	C17B—H17B	0.9300
C13—C14	1.536 (4)	C18B—C19B	1.363 (12)
C13—H13A	1.0472	C18B—H18B	0.9300
C13—H13B	1.0318	C19B—C20B	1.382 (12)
C14—C15	1.465 (4)	C19B—H19B	0.9300
C14—H14B	1.0410	C20B—C21B	1.380 (11)
C14—H14A	1.0595	C20B—H20B	0.9300
C3—C2	1.387 (5)	C21B—H21B	0.9300
C6—Rh1—O1	177.17 (13)	O2—C3—C5	114.5 (4)
C6—Rh1—O2	92.15 (13)	C2—C3—C5	119.3 (3)
O1—Rh1—O2	89.19 (9)	C1—C2—C3	126.9 (3)
C6—Rh1—P1	89.85 (11)	C1—C2—H2	116.5
O1—Rh1—P1	88.74 (6)	C3—C2—H2	116.5
O2—Rh1—P1	177.57 (6)	O1—C1—C2	125.7 (3)
C6—Rh1—H14A	129.8	O1—C1—C4	114.0 (3)
O1—Rh1—H14A	51.2	C2—C1—C4	120.3 (3)
O2—Rh1—H14A	118.8	O3—C6—Rh1	178.8 (4)
P1—Rh1—H14A	60.6	C1—C4—H4A	109.5
C6—Rh1—H13A	133.2	C1—C4—H4B	109.5
O1—Rh1—H13A	45.2	H4A—C4—H4B	109.5
O2—Rh1—H13A	134.3	C1—C4—H4C	109.5
P1—Rh1—H13A	43.5	H4A—C4—H4C	109.5
H14A—Rh1—H13A	40.1	H4B—C4—H4C	109.5
C7—P1—C16B	107.0 (6)	C3—C5—H5A	109.5
C7—P1—C16A	100.9 (6)	C3—C5—H5B	109.5
C7—P1—C13	101.38 (13)	H5A—C5—H5B	109.5
C16B—P1—C13	100.8 (6)	C3—C5—H5C	109.5
C16A—P1—C13	106.1 (6)	H5A—C5—H5C	109.5
C7—P1—Rh1	118.97 (10)	H5B—C5—H5C	109.5
C16B—P1—Rh1	112.7 (6)	C17A—C16A—C21A	118.8 (8)
C16A—P1—Rh1	113.8 (6)	C17A—C16A—P1	118.9 (10)
C13—P1—Rh1	113.90 (10)	C21A—C16A—P1	121.7 (10)
C3—O2—Rh1	125.3 (2)	C18A—C17A—C16A	120.1 (9)
C1—O1—Rh1	126.4 (2)	C18A—C17A—H17A	119.9
C8—C7—C12	119.1 (3)	C16A—C17A—H17A	119.9
C8—C7—P1	120.5 (2)	C19A—C18A—C17A	120.1 (8)
C12—C7—P1	120.2 (2)	C19A—C18A—H18A	119.9
C9—C8—C7	120.5 (3)	C17A—C18A—H18A	119.9
C9—C8—H8	119.7	C18A—C19A—C20A	121.6 (8)
C7—C8—H8	119.7	C18A—C19A—H19A	119.2
C10—C9—C8	119.8 (4)	C20A—C19A—H19A	119.2
C10—C9—H9	120.1	C21A—C20A—C19A	117.9 (9)
C8—C9—H9	120.1	C21A—C20A—H20A	121.0
C9—C10—C11	120.5 (3)	C19A—C20A—H20A	121.0
C9—C10—H10	119.7	C16A—C21A—C20A	121.2 (8)
C11—C10—H10	119.7	C16A—C21A—H21A	119.4
C10—C11—C12	120.3 (4)	C20A—C21A—H21A	119.4
C10—C11—H11	119.9	C17B—C16B—C21B	119.2 (9)
C12—C11—H11	119.9	C17B—C16B—P1	121.3 (10)
C11—C12—C7	119.8 (3)	C21B—C16B—P1	119.5 (10)
C11—C12—H12	120.1	C16B—C17B—C18B	122.1 (10)
C7—C12—H12	120.1	C16B—C17B—H17B	118.9
C14—C13—P1	110.63 (19)	C18B—C17B—H17B	118.9
C14—C13—H13A	106.7	C19B—C18B—C17B	117.5 (10)
P1—C13—H13A	106.4	C19B—C18B—H18B	121.3
C14—C13—H13B	108.1	C17B—C18B—H18B	121.3
P1—C13—H13B	111.6	C18B—C19B—C20B	121.7 (9)
H13A—C13—H13B	113.3	C18B—C19B—H19B	119.2
C15—C14—C13	111.6 (3)	C20B—C19B—H19B	119.2
C15—C14—H14B	106.1	C21B—C20B—C19B	120.4 (10)
C13—C14—H14B	119.0	C21B—C20B—H20B	119.8
C15—C14—H14A	105.8	C19B—C20B—H20B	119.8
C13—C14—H14A	108.2	C20B—C21B—C16B	119.0 (10)
H14B—C14—H14A	105.1	C20B—C21B—H21B	120.5
N1—C15—C14	179.3 (4)	C16B—C21B—H21B	120.5
O2—C3—C2	126.2 (3)

(Acetylacetonato-κ²O,O')carbonyl[3-(di-tert-butylphosphanyl)propanenitrile-κP]rhodium(I) (2i)

Crystal data

[Rh(C5H7O2)(C11H22N)(CO)]	F(000) = 888
Mr = 429.29	Dx = 1.409 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.531 (3) Å	Cell parameters from 19824 reflections
b = 12.450 (3) Å	θ = 27–3°
c = 12.161 (2) Å	µ = 0.94 mm^−1
β = 98.92 (3)°	T = 298 K
V = 2024.0 (7) Å^3	Platelet, yellow
Z = 4	0.50 × 0.15 × 0.10 mm

Data collection

Rigaku AFC-7S Mercury diffractometer	3851 independent reflections
Radiation source: fine-focus seal tube	2307 reflections with I > 2σ(I)
Detector resolution: 14.6306 pixels mm^-1	Rint = 0.090
ω scans	θmax = 27.7°, θmin = 1.5°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −16→17
Tmin = 0.818, Tmax = 0.942	k = −14→14
19824 measured reflections	l = −15→15

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.075	H-atom parameters constrained
wR(F^2) = 0.178	w = 1/[σ^2(Fo^2) + (0.0407P)^2 + 8.7706P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max < 0.001
3851 reflections	Δρmax = 0.50 e Å^−3
209 parameters	Δρmin = −0.84 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Rh1	0.30329 (5)	0.25416 (6)	0.11383 (6)	0.0480 (2)
P1	0.26047 (17)	0.42905 (18)	0.13165 (19)	0.0447 (6)
O1	0.1572 (4)	0.2136 (5)	0.1180 (5)	0.0557 (16)
O2	0.3358 (5)	0.0914 (5)	0.1043 (5)	0.0588 (16)
O3	0.5129 (6)	0.3017 (7)	0.0906 (9)	0.104 (3)
N1	−0.0282 (8)	0.3013 (8)	0.3290 (9)	0.084 (3)
C1	0.1179 (7)	0.1187 (8)	0.1135 (7)	0.053 (2)
C2	0.1730 (7)	0.0241 (8)	0.1086 (7)	0.054 (2)
H2	0.1374	−0.0399	0.1075	0.065*
C3	0.2736 (8)	0.0151 (8)	0.1052 (8)	0.059 (3)
C5	0.3200 (9)	−0.0967 (7)	0.1058 (9)	0.081 (3)
H5A	0.3905	−0.0903	0.1044	0.121*
H5B	0.2893	−0.1358	0.0414	0.121*
H5C	0.3093	−0.1343	0.1719	0.121*
C4	0.0102 (7)	0.1157 (8)	0.1149 (8)	0.064 (3)
H4A	−0.0029	0.1320	0.1884	0.097*
H4B	−0.0149	0.0453	0.0938	0.097*
H4C	−0.0223	0.1677	0.0633	0.097*
C6	0.4299 (8)	0.2876 (7)	0.1024 (9)	0.064 (3)
C13	0.1426 (6)	0.4313 (7)	0.1894 (7)	0.051 (2)
H13A	0.1236	0.5055	0.1985	0.061*
H13B	0.0907	0.3984	0.1360	0.061*
C14	0.1466 (7)	0.3732 (8)	0.3019 (8)	0.060 (3)
H14A	0.1924	0.3130	0.3049	0.071*
H14B	0.1719	0.4222	0.3617	0.071*
C15	0.0474 (8)	0.3343 (8)	0.3181 (9)	0.060 (3)
C7	0.2243 (7)	0.4954 (7)	−0.0091 (8)	0.054 (2)
C8	0.1937 (10)	0.6139 (8)	−0.0037 (10)	0.090 (4)
H8A	0.1768	0.6417	−0.0778	0.136*
H8B	0.2484	0.6543	0.0358	0.136*
H8C	0.1368	0.6196	0.0343	0.136*
C9	0.3072 (8)	0.4826 (9)	−0.0780 (9)	0.077 (3)
H9A	0.2882	0.5165	−0.1490	0.116*
H9B	0.3192	0.4076	−0.0888	0.116*
H9C	0.3671	0.5155	−0.0401	0.116*
C10	0.1334 (7)	0.4328 (9)	−0.0702 (8)	0.069 (3)
H10A	0.1128	0.4640	−0.1423	0.103*
H10B	0.0794	0.4365	−0.0278	0.103*
H10C	0.1518	0.3591	−0.0785	0.103*
C11	0.3479 (7)	0.5177 (8)	0.2282 (8)	0.056 (2)
C12	0.3935 (8)	0.4479 (10)	0.3277 (9)	0.083 (3)
H12A	0.4386	0.4905	0.3787	0.125*
H12B	0.4293	0.3889	0.3016	0.125*
H12C	0.3410	0.4207	0.3648	0.125*
C16	0.2922 (8)	0.6120 (8)	0.2739 (9)	0.082 (3)
H16A	0.3391	0.6551	0.3223	0.123*
H16B	0.2425	0.5843	0.3148	0.123*
H16C	0.2605	0.6552	0.2132	0.123*
C17	0.4337 (8)	0.5603 (9)	0.1733 (10)	0.084 (4)
H17A	0.4761	0.6049	0.2250	0.127*
H17B	0.4073	0.6017	0.1088	0.127*
H17C	0.4718	0.5011	0.1514	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rh1	0.0480 (4)	0.0411 (4)	0.0564 (4)	−0.0046 (3)	0.0129 (3)	0.0005 (4)
P1	0.0470 (13)	0.0419 (13)	0.0453 (13)	−0.0047 (10)	0.0070 (10)	0.0013 (11)
O1	0.057 (4)	0.044 (4)	0.068 (4)	−0.014 (3)	0.016 (3)	−0.005 (3)
O2	0.065 (4)	0.041 (4)	0.072 (4)	0.001 (3)	0.015 (3)	−0.006 (3)
O3	0.060 (5)	0.081 (6)	0.182 (9)	0.002 (4)	0.048 (6)	0.026 (6)
N1	0.090 (7)	0.069 (6)	0.106 (8)	0.003 (5)	0.056 (6)	−0.010 (6)
C1	0.058 (6)	0.057 (6)	0.043 (5)	−0.018 (5)	0.007 (5)	−0.002 (4)
C2	0.068 (7)	0.049 (6)	0.043 (5)	−0.022 (5)	0.001 (5)	−0.002 (4)
C3	0.079 (7)	0.048 (6)	0.049 (6)	−0.005 (5)	0.004 (5)	−0.007 (4)
C5	0.107 (9)	0.035 (5)	0.097 (8)	0.012 (5)	0.005 (7)	−0.006 (5)
C4	0.067 (7)	0.055 (6)	0.071 (7)	−0.009 (5)	0.009 (5)	−0.014 (5)
C6	0.061 (7)	0.042 (5)	0.089 (8)	0.002 (5)	0.016 (6)	0.008 (5)
C13	0.058 (5)	0.045 (5)	0.052 (5)	−0.002 (4)	0.014 (5)	0.000 (4)
C14	0.060 (6)	0.063 (6)	0.058 (6)	0.007 (5)	0.013 (5)	0.013 (5)
C15	0.072 (7)	0.053 (6)	0.063 (7)	0.010 (5)	0.032 (6)	0.002 (5)
C7	0.063 (6)	0.047 (5)	0.052 (6)	0.001 (4)	0.011 (5)	0.009 (4)
C8	0.131 (11)	0.054 (7)	0.081 (8)	0.013 (7)	0.000 (7)	0.017 (6)
C9	0.088 (8)	0.081 (8)	0.066 (7)	−0.007 (6)	0.024 (6)	0.009 (6)
C10	0.070 (7)	0.083 (8)	0.049 (6)	−0.005 (6)	−0.006 (5)	0.000 (5)
C11	0.055 (6)	0.058 (6)	0.052 (6)	−0.009 (5)	−0.001 (5)	−0.014 (5)
C12	0.070 (7)	0.111 (10)	0.062 (7)	−0.014 (7)	−0.009 (6)	−0.001 (7)
C16	0.092 (8)	0.065 (7)	0.087 (8)	−0.015 (6)	0.010 (7)	−0.029 (6)
C17	0.076 (7)	0.086 (8)	0.090 (8)	−0.038 (6)	0.010 (6)	−0.015 (7)

Geometric parameters (Å, º)

Rh1—C6	1.790 (11)	C14—H14A	0.9700
Rh1—O1	2.048 (6)	C14—H14B	0.9700
Rh1—O2	2.081 (6)	C7—C9	1.510 (13)
Rh1—P1	2.272 (2)	C7—C8	1.535 (13)
P1—C13	1.840 (9)	C7—C10	1.545 (12)
P1—C11	1.888 (9)	C8—H8A	0.9600
P1—C7	1.896 (9)	C8—H8B	0.9600
O1—C1	1.294 (10)	C8—H8C	0.9600
O2—C3	1.271 (11)	C9—H9A	0.9600
O3—C6	1.167 (11)	C9—H9B	0.9600
N1—C15	1.129 (12)	C9—H9C	0.9600
C1—C2	1.400 (13)	C10—H10A	0.9600
C1—C4	1.460 (12)	C10—H10B	0.9600
C2—C3	1.373 (13)	C10—H10C	0.9600
C2—H2	0.9300	C11—C17	1.521 (13)
C3—C5	1.527 (13)	C11—C12	1.539 (13)
C5—H5A	0.9600	C11—C16	1.544 (13)
C5—H5B	0.9600	C12—H12A	0.9600
C5—H5C	0.9600	C12—H12B	0.9600
C4—H4A	0.9600	C12—H12C	0.9600
C4—H4B	0.9600	C16—H16A	0.9600
C4—H4C	0.9600	C16—H16B	0.9600
C13—C14	1.541 (12)	C16—H16C	0.9600
C13—H13A	0.9700	C17—H17A	0.9600
C13—H13B	0.9700	C17—H17B	0.9600
C14—C15	1.469 (14)	C17—H17C	0.9600
C6—Rh1—O1	176.9 (4)	C9—C7—C8	110.7 (9)
C6—Rh1—O2	90.5 (4)	C9—C7—C10	106.5 (8)
O1—Rh1—O2	88.6 (2)	C8—C7—C10	107.8 (8)
C6—Rh1—P1	92.6 (3)	C9—C7—P1	110.2 (7)
O1—Rh1—P1	88.41 (18)	C8—C7—P1	114.4 (7)
O2—Rh1—P1	176.28 (19)	C10—C7—P1	106.8 (6)
C13—P1—C11	104.5 (4)	C7—C8—H8A	109.5
C13—P1—C7	102.7 (4)	C7—C8—H8B	109.5
C11—P1—C7	110.8 (4)	H8A—C8—H8B	109.5
C13—P1—Rh1	107.5 (3)	C7—C8—H8C	109.5
C11—P1—Rh1	118.4 (3)	H8A—C8—H8C	109.5
C7—P1—Rh1	111.5 (3)	H8B—C8—H8C	109.5
C1—O1—Rh1	128.0 (6)	C7—C9—H9A	109.5
C3—O2—Rh1	125.5 (6)	C7—C9—H9B	109.5
O1—C1—C2	123.5 (8)	H9A—C9—H9B	109.5
O1—C1—C4	115.3 (9)	C7—C9—H9C	109.5
C2—C1—C4	121.2 (8)	H9A—C9—H9C	109.5
C3—C2—C1	127.3 (9)	H9B—C9—H9C	109.5
C3—C2—H2	116.3	C7—C10—H10A	109.5
C1—C2—H2	116.3	C7—C10—H10B	109.5
O2—C3—C2	127.0 (9)	H10A—C10—H10B	109.5
O2—C3—C5	114.1 (9)	C7—C10—H10C	109.5
C2—C3—C5	118.9 (9)	H10A—C10—H10C	109.5
C3—C5—H5A	109.5	H10B—C10—H10C	109.5
C3—C5—H5B	109.5	C17—C11—C12	107.5 (8)
H5A—C5—H5B	109.5	C17—C11—C16	110.0 (9)
C3—C5—H5C	109.5	C12—C11—C16	107.7 (8)
H5A—C5—H5C	109.5	C17—C11—P1	112.2 (7)
H5B—C5—H5C	109.5	C12—C11—P1	107.1 (7)
C1—C4—H4A	109.5	C16—C11—P1	112.0 (6)
C1—C4—H4B	109.5	C11—C12—H12A	109.5
H4A—C4—H4B	109.5	C11—C12—H12B	109.5
C1—C4—H4C	109.5	H12A—C12—H12B	109.5
H4A—C4—H4C	109.5	C11—C12—H12C	109.5
H4B—C4—H4C	109.5	H12A—C12—H12C	109.5
O3—C6—Rh1	174.6 (10)	H12B—C12—H12C	109.5
C14—C13—P1	114.7 (6)	C11—C16—H16A	109.5
C14—C13—H13A	108.6	C11—C16—H16B	109.5
P1—C13—H13A	108.6	H16A—C16—H16B	109.5
C14—C13—H13B	108.6	C11—C16—H16C	109.5
P1—C13—H13B	108.6	H16A—C16—H16C	109.5
H13A—C13—H13B	107.6	H16B—C16—H16C	109.5
C15—C14—C13	111.5 (8)	C11—C17—H17A	109.5
C15—C14—H14A	109.3	C11—C17—H17B	109.5
C13—C14—H14A	109.3	H17A—C17—H17B	109.5
C15—C14—H14B	109.3	C11—C17—H17C	109.5
C13—C14—H14B	109.3	H17A—C17—H17C	109.5
H14A—C14—H14B	108.0	H17B—C17—H17C	109.5
N1—C15—C14	177.8 (11)