Carbonyl[4-(2,6-dimethyl-phenyl-amino)pent-3-en-2-onato-κN,O](triphenyl-phosphine-κP)rhodium(I) acetone hemi-solvate.

In the title compound, [Rh(C(13)H(16)NO)(C(18)H(15)P)(CO)]·0.5C(3)H(6)O, the Rh atom exhibits a square-planar coordination geometry, being coordinated by the N and O atoms of the bidentate β-diketonato ligand, a P atom from the triphenyl-phosphine unit and a C atom from the carbonyl group. The asymmetric unit also contains a disordered half-mol-ecule, lying about an inversion center, of the acetone solvate. Inter-molecular C-H⋯O hydrogen bonds are observed between a C-H group of the triphenyl-phosphine unit and a carbonyl O atom and between the methyl group of the enamino-ketonato backbone and the solvent O atom. In addition, an intra-molecular inter-action is observed between a C-H group of the triphenyl-phosphine unit and the O atom of the enamino-ketonato ligand.

Related literature

For synthetic background, see: Shaheen et al. (2006 ▶); Cornils & Hermann (1996); Bonati & Wilkinson (1964 ▶). For appplications of rhodium(I) dicarbonyl complexes, see: Cornils & Herrmann (1996 ▶); Trzeciak & Ziolkowski (1994 ▶); Van Rooy et al. (1995 ▶). For related structures, see: Damoense et al. (1994 ▶); Varshavsky et al. (2001 ▶); Venter et al. (2009 ▶).

Experimental

Crystal data

[n class="Chemical">Rh(C13H16n class="Chemical">NO)(C18H15P)(n class="Chemical">CO)]·0.5C3H6O

M = 624.5

Monoclinic,

a = 16.8558 (8) Å

b = 11.4028 (5) Å

c = 16.4059 (8) Å

β = 108.733 (1)°

V = 2986.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.66 mm−1

T = 100 K

0.31 × 0.15 × 0.11 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.822, T max = 0.931

23158 measured reflections

7425 independent reflections

6081 reflections with > 2σI)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.112

S = 1.09

7425 reflections

354 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.54 e Å−3

Δρmin = −1.32 e Å−3

Data collection: n class="Gene">APEX2 (Bruker, 2005 ▶); cell refinpan>emenclass="Chemical">pan>t: SAIn class="Chemical">NT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680904817X/pv2227sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904817X/pv2227Isup2.hkl

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

[Rh(C13H16NO)(C18H15P)(CO)]·0.5C3H6O	F(000) = 1288
Mr = 624.5	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6670 reflections
a = 16.8558 (8) Å	θ = 2.5–28.2°
b = 11.4028 (5) Å	µ = 0.66 mm−1
c = 16.4059 (8) Å	T = 100 K
β = 108.733 (1)°	Cuboid, yellow
V = 2986.2 (2) Å3	0.31 × 0.15 × 0.11 mm
Z = 4

Bruker X8 APEXII 4K Kappa CCD diffractometer	7425 independent reflections
Radiation source: fine-focus sealed tube	6081 reflections with > 2σI)
graphite	Rint = 0.042
ω and φ scans	θmax = 28.3°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −21→22
Tmin = 0.822, Tmax = 0.931	k = −15→11
23158 measured reflections	l = −21→21

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0577P)2 + 1.4787P] where P = (Fo2 + 2Fc2)/3
7425 reflections	(Δ/σ)max = 0.002
354 parameters	Δρmax = 1.54 e Å−3
1 restraint	Δρmin = −1.32 e Å−3

Experimental. The intensity data was collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 60 s/frame. A total of 688 frames were collected with a frame width of 0.5° covering up to θ = 28.24° with 99.8% completeness accomplished.

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.7144 (2)	0.7625 (3)	0.4744 (2)	0.0257 (7)
H1A	0.7697	0.7807	0.5152	0.039*
H1B	0.6712	0.7804	0.5007	0.039*
H1C	0.7048	0.8097	0.4222	0.039*
C2	0.71032 (17)	0.6337 (2)	0.45128 (18)	0.0168 (5)
C3	0.65757 (17)	0.5637 (2)	0.48382 (18)	0.0183 (6)
H3	0.6324	0.6017	0.5209	0.022*
C4	0.63880 (17)	0.4461 (2)	0.46740 (19)	0.0180 (6)
C5	0.57863 (19)	0.3856 (3)	0.5045 (2)	0.0265 (7)
H5A	0.5288	0.3609	0.4577	0.04*
H5B	0.5621	0.4399	0.5425	0.04*
H5C	0.6058	0.3167	0.5375	0.04*
C14	0.84522 (17)	0.4446 (2)	0.32802 (17)	0.0166 (5)
C111	0.80357 (17)	0.6734 (2)	0.37352 (18)	0.0164 (5)
C112	0.76869 (19)	0.7250 (2)	0.2919 (2)	0.0223 (6)
C113	0.8183 (2)	0.8000 (3)	0.2624 (2)	0.0271 (7)
H113	0.7952	0.8365	0.2078	0.033*
C114	0.9008 (2)	0.8226 (2)	0.3109 (2)	0.0292 (7)
H114	0.9338	0.8746	0.2897	0.035*
C115	0.93503 (19)	0.7690 (2)	0.3902 (2)	0.0242 (6)
H115	0.9919	0.7836	0.4228	0.029*
C116	0.88743 (18)	0.6938 (2)	0.42310 (19)	0.0194 (6)
C117	0.6798 (2)	0.6980 (3)	0.2380 (2)	0.0318 (7)
H11A	0.6667	0.7385	0.1826	0.048*
H11B	0.6414	0.7247	0.2682	0.048*
H11C	0.6734	0.6132	0.2283	0.048*
C118	0.92484 (19)	0.6332 (3)	0.5082 (2)	0.0257 (7)
H11D	0.9859	0.6413	0.5269	0.039*
H11E	0.9099	0.5499	0.5021	0.039*
H11F	0.9031	0.6689	0.551	0.039*
C311	0.82259 (17)	0.1691 (2)	0.27715 (17)	0.0149 (5)
C312	0.90839 (17)	0.1910 (2)	0.30147 (18)	0.0168 (5)
H312	0.9352	0.2308	0.354	0.02*
C313	0.95533 (17)	0.1553 (2)	0.24967 (19)	0.0193 (6)
H313	1.0138	0.1707	0.267	0.023*
C314	0.91660 (18)	0.0976 (2)	0.17315 (19)	0.0212 (6)
H314	0.9483	0.0736	0.1375	0.025*
C315	0.83113 (18)	0.0749 (2)	0.14845 (19)	0.0190 (6)
H315	0.8045	0.035	0.0959	0.023*
C316	0.78449 (17)	0.1103 (2)	0.20019 (18)	0.0168 (5)
H316	0.7261	0.0943	0.1829	0.02*
C321	0.66208 (17)	0.1553 (2)	0.30122 (17)	0.0153 (5)
C322	0.59944 (17)	0.2176 (2)	0.24164 (19)	0.0202 (6)
H322	0.6093	0.296	0.2279	0.024*
C323	0.52197 (18)	0.1657 (3)	0.2017 (2)	0.0243 (6)
H323	0.4799	0.208	0.1594	0.029*
C324	0.50573 (19)	0.0534 (3)	0.2231 (2)	0.0260 (7)
H324	0.4523	0.019	0.1966	0.031*
C325	0.5676 (2)	−0.0085 (3)	0.2829 (2)	0.0386 (9)
H325	0.557	−0.086	0.2979	0.046*
C326	0.6459 (2)	0.0424 (3)	0.3217 (2)	0.0335 (8)
H326	0.6884	−0.001	0.3627	0.04*
C331	0.81170 (17)	0.1399 (2)	0.44688 (17)	0.0156 (5)
C332	0.7927 (2)	0.1752 (3)	0.51929 (19)	0.0266 (7)
H332	0.7579	0.2416	0.5163	0.032*
C333	0.8240 (2)	0.1144 (3)	0.5959 (2)	0.0334 (8)
H333	0.8091	0.1378	0.6447	0.04*
C334	0.8770 (2)	0.0196 (3)	0.60188 (19)	0.0263 (7)
H334	0.8999	−0.0205	0.655	0.032*
C335	0.89635 (18)	−0.0163 (2)	0.53013 (19)	0.0222 (6)
H335	0.932	−0.082	0.5339	0.027*
C336	0.86407 (18)	0.0429 (2)	0.45242 (19)	0.0196 (6)
H336	0.8775	0.0176	0.4032	0.024*
N11	0.75420 (14)	0.59212 (18)	0.40401 (15)	0.0148 (5)
O12	0.66821 (11)	0.37910 (16)	0.42069 (13)	0.0174 (4)
O14	0.90058 (13)	0.46375 (18)	0.30306 (13)	0.0225 (4)
P13	0.76530 (4)	0.22182 (6)	0.34722 (4)	0.01315 (15)
Rh1	0.761010 (12)	0.417429 (17)	0.371227 (13)	0.01263 (8)
O01	0.4759 (6)	0.3631 (7)	0.0331 (6)	0.0963 (16)	0.5
C01	0.4182 (4)	0.5252 (5)	−0.0389 (4)	0.0963 (16)
H01A	0.366	0.4813	−0.0482	0.144*
H01B	0.4236	0.5472	−0.0946	0.144*
H01C	0.4173	0.5961	−0.0055	0.144*
C02	0.4899 (9)	0.4513 (10)	0.0086 (9)	0.0963 (16)	0.5

	U11	U22	U33	U12	U13	U23
C1	0.0290 (16)	0.0158 (14)	0.0378 (18)	0.0010 (12)	0.0183 (14)	−0.0024 (13)
C2	0.0145 (13)	0.0149 (13)	0.0204 (14)	0.0019 (10)	0.0049 (11)	0.0014 (10)
C3	0.0165 (13)	0.0185 (13)	0.0215 (14)	0.0041 (11)	0.0082 (11)	0.0009 (11)
C4	0.0127 (13)	0.0192 (13)	0.0220 (14)	0.0039 (10)	0.0056 (11)	0.0037 (11)
C5	0.0233 (15)	0.0239 (15)	0.0378 (18)	−0.0002 (12)	0.0176 (14)	0.0045 (13)
C14	0.0190 (14)	0.0134 (12)	0.0157 (13)	−0.0017 (10)	0.0032 (11)	−0.0036 (10)
C111	0.0206 (14)	0.0097 (12)	0.0224 (14)	−0.0009 (10)	0.0118 (12)	−0.0016 (10)
C112	0.0273 (15)	0.0152 (13)	0.0279 (16)	0.0027 (11)	0.0137 (13)	0.0022 (11)
C113	0.0408 (19)	0.0149 (13)	0.0312 (17)	0.0020 (13)	0.0193 (15)	0.0041 (12)
C114	0.0410 (19)	0.0138 (14)	0.043 (2)	−0.0063 (13)	0.0286 (16)	−0.0043 (13)
C115	0.0243 (15)	0.0173 (14)	0.0375 (18)	−0.0055 (11)	0.0189 (14)	−0.0117 (12)
C116	0.0220 (14)	0.0136 (12)	0.0242 (15)	−0.0014 (11)	0.0099 (12)	−0.0038 (11)
C117	0.0293 (17)	0.0335 (17)	0.0289 (17)	0.0046 (14)	0.0043 (14)	0.0104 (14)
C118	0.0217 (15)	0.0267 (16)	0.0243 (16)	−0.0035 (12)	0.0013 (13)	−0.0047 (12)
C311	0.0186 (13)	0.0098 (12)	0.0171 (13)	0.0012 (10)	0.0066 (11)	0.0014 (10)
C312	0.0165 (13)	0.0147 (12)	0.0180 (13)	−0.0017 (10)	0.0037 (11)	−0.0003 (10)
C313	0.0138 (13)	0.0189 (13)	0.0249 (15)	0.0030 (11)	0.0059 (11)	0.0037 (11)
C314	0.0225 (15)	0.0196 (14)	0.0242 (15)	0.0043 (11)	0.0112 (13)	0.0025 (11)
C315	0.0211 (14)	0.0176 (13)	0.0180 (14)	−0.0002 (11)	0.0060 (12)	−0.0023 (10)
C316	0.0165 (13)	0.0143 (12)	0.0187 (14)	−0.0012 (10)	0.0041 (11)	−0.0001 (10)
C321	0.0159 (13)	0.0149 (12)	0.0163 (13)	−0.0011 (10)	0.0067 (11)	−0.0025 (10)
C322	0.0173 (14)	0.0168 (13)	0.0251 (15)	−0.0012 (11)	0.0049 (12)	−0.0008 (11)
C323	0.0155 (14)	0.0265 (16)	0.0261 (16)	0.0030 (12)	0.0001 (12)	0.0001 (12)
C324	0.0166 (14)	0.0312 (16)	0.0283 (16)	−0.0067 (12)	0.0045 (13)	−0.0052 (13)
C325	0.0317 (18)	0.0261 (17)	0.048 (2)	−0.0167 (14)	−0.0006 (16)	0.0098 (15)
C326	0.0249 (16)	0.0237 (16)	0.041 (2)	−0.0047 (13)	−0.0047 (15)	0.0129 (14)
C331	0.0162 (13)	0.0134 (12)	0.0147 (13)	−0.0016 (10)	0.0014 (11)	−0.0017 (10)
C332	0.0368 (18)	0.0224 (15)	0.0195 (15)	0.0132 (13)	0.0077 (13)	0.0011 (12)
C333	0.054 (2)	0.0313 (17)	0.0153 (15)	0.0234 (16)	0.0113 (15)	0.0034 (13)
C334	0.0340 (17)	0.0214 (15)	0.0188 (15)	0.0074 (13)	0.0022 (13)	0.0031 (12)
C335	0.0246 (15)	0.0168 (14)	0.0233 (15)	0.0049 (11)	0.0052 (12)	0.0005 (11)
C336	0.0220 (14)	0.0160 (13)	0.0213 (14)	0.0013 (11)	0.0075 (12)	−0.0017 (11)
N11	0.0142 (11)	0.0107 (10)	0.0191 (12)	−0.0009 (8)	0.0049 (9)	0.0012 (8)
O12	0.0152 (9)	0.0148 (9)	0.0242 (10)	−0.0008 (8)	0.0091 (8)	0.0014 (8)
O14	0.0261 (11)	0.0180 (10)	0.0280 (11)	−0.0059 (8)	0.0152 (9)	−0.0034 (8)
P13	0.0123 (3)	0.0117 (3)	0.0142 (3)	−0.0008 (2)	0.0027 (3)	−0.0002 (2)
Rh1	0.01250 (12)	0.01060 (11)	0.01490 (12)	−0.00047 (7)	0.00457 (8)	0.00021 (7)
O01	0.139 (5)	0.057 (3)	0.104 (4)	−0.010 (3)	0.054 (4)	0.007 (2)
C01	0.139 (5)	0.057 (3)	0.104 (4)	−0.010 (3)	0.054 (4)	0.007 (2)
C02	0.139 (5)	0.057 (3)	0.104 (4)	−0.010 (3)	0.054 (4)	0.007 (2)

C1—C2	1.513 (4)	C313—H313	0.95
C1—H1A	0.98	C314—C315	1.390 (4)
C1—H1B	0.98	C314—H314	0.95
C1—H1C	0.98	C315—C316	1.389 (4)
C2—N11	1.320 (4)	C315—H315	0.95
C2—C3	1.420 (4)	C316—H316	0.95
C3—C4	1.384 (4)	C321—C326	1.380 (4)
C3—H3	0.95	C321—C322	1.383 (4)
C4—O12	1.289 (3)	C321—P13	1.824 (3)
C4—C5	1.507 (4)	C322—C323	1.391 (4)
C5—H5A	0.98	C322—H322	0.95
C5—H5B	0.98	C323—C324	1.378 (4)
C5—H5C	0.98	C323—H323	0.95
C14—O14	1.154 (3)	C324—C325	1.375 (4)
C14—Rh1	1.805 (3)	C324—H324	0.95
C111—C116	1.405 (4)	C325—C326	1.394 (4)
C111—C112	1.406 (4)	C325—H325	0.95
C111—N11	1.439 (3)	C326—H326	0.95
C112—C113	1.387 (4)	C331—C332	1.385 (4)
C112—C117	1.507 (4)	C331—C336	1.400 (4)
C113—C114	1.388 (5)	C331—P13	1.827 (3)
C113—H113	0.95	C332—C333	1.383 (4)
C114—C115	1.385 (5)	C332—H332	0.95
C114—H114	0.95	C333—C334	1.386 (4)
C115—C116	1.396 (4)	C333—H333	0.95
C115—H115	0.95	C334—C335	1.380 (4)
C116—C118	1.503 (4)	C334—H334	0.95
C117—H11A	0.98	C335—C336	1.390 (4)
C117—H11B	0.98	C335—H335	0.95
C117—H11C	0.98	C336—H336	0.95
C118—H11D	0.98	N11—Rh1	2.076 (2)
C118—H11E	0.98	O12—Rh1	2.0277 (19)
C118—H11F	0.98	P13—Rh1	2.2701 (7)
C311—C316	1.391 (4)	O01—C02	1.135 (12)
C311—C312	1.394 (4)	C01—C02	1.474 (13)
C311—P13	1.825 (3)	C01—H01A	0.98
C312—C313	1.395 (4)	C01—H01B	0.98
C312—H312	0.95	C01—H01C	0.98
C313—C314	1.382 (4)	C02—C01i	1.492 (16)
C2—C1—H1A	109.5	C314—C315—H315	119.8
C2—C1—H1B	109.5	C315—C316—C311	120.5 (3)
H1A—C1—H1B	109.5	C315—C316—H316	119.7
C2—C1—H1C	109.5	C311—C316—H316	119.7
H1A—C1—H1C	109.5	C326—C321—C322	119.0 (3)
H1B—C1—H1C	109.5	C326—C321—P13	121.6 (2)
N11—C2—C3	123.8 (2)	C322—C321—P13	119.3 (2)
N11—C2—C1	120.5 (2)	C321—C322—C323	120.2 (3)
C3—C2—C1	115.8 (2)	C321—C322—H322	119.9
C4—C3—C2	127.1 (3)	C323—C322—H322	119.9
C4—C3—H3	116.5	C324—C323—C322	120.6 (3)
C2—C3—H3	116.5	C324—C323—H323	119.7
O12—C4—C3	125.6 (3)	C322—C323—H323	119.7
O12—C4—C5	113.9 (2)	C325—C324—C323	119.4 (3)
C3—C4—C5	120.4 (3)	C325—C324—H324	120.3
C4—C5—H5A	109.5	C323—C324—H324	120.3
C4—C5—H5B	109.5	C324—C325—C326	120.1 (3)
H5A—C5—H5B	109.5	C324—C325—H325	119.9
C4—C5—H5C	109.5	C326—C325—H325	119.9
H5A—C5—H5C	109.5	C321—C326—C325	120.6 (3)
H5B—C5—H5C	109.5	C321—C326—H326	119.7
O14—C14—Rh1	177.7 (2)	C325—C326—H326	119.7
C116—C111—C112	121.1 (3)	C332—C331—C336	119.2 (3)
C116—C111—N11	119.5 (2)	C332—C331—P13	117.9 (2)
C112—C111—N11	119.3 (2)	C336—C331—P13	122.8 (2)
C113—C112—C111	118.4 (3)	C333—C332—C331	120.5 (3)
C113—C112—C117	121.2 (3)	C333—C332—H332	119.7
C111—C112—C117	120.4 (3)	C331—C332—H332	119.7
C112—C113—C114	121.3 (3)	C332—C333—C334	120.3 (3)
C112—C113—H113	119.3	C332—C333—H333	119.9
C114—C113—H113	119.3	C334—C333—H333	119.9
C115—C114—C113	119.6 (3)	C335—C334—C333	119.6 (3)
C115—C114—H114	120.2	C335—C334—H334	120.2
C113—C114—H114	120.2	C333—C334—H334	120.2
C114—C115—C116	121.2 (3)	C334—C335—C336	120.5 (3)
C114—C115—H115	119.4	C334—C335—H335	119.7
C116—C115—H115	119.4	C336—C335—H335	119.7
C115—C116—C111	118.3 (3)	C335—C336—C331	119.8 (3)
C115—C116—C118	121.3 (3)	C335—C336—H336	120.1
C111—C116—C118	120.4 (3)	C331—C336—H336	120.1
C112—C117—H11A	109.5	C2—N11—C111	118.0 (2)
C112—C117—H11B	109.5	C2—N11—Rh1	125.79 (18)
H11A—C117—H11B	109.5	C111—N11—Rh1	116.24 (17)
C112—C117—H11C	109.5	C4—O12—Rh1	127.13 (18)
H11A—C117—H11C	109.5	C311—P13—C321	103.27 (12)
H11B—C117—H11C	109.5	C311—P13—C331	103.55 (12)
C116—C118—H11D	109.5	C321—P13—C331	103.59 (12)
C116—C118—H11E	109.5	C311—P13—Rh1	119.08 (9)
H11D—C118—H11E	109.5	C321—P13—Rh1	113.64 (9)
C116—C118—H11F	109.5	C331—P13—Rh1	112.06 (9)
H11D—C118—H11F	109.5	C14—Rh1—O12	177.36 (10)
H11E—C118—H11F	109.5	C14—Rh1—N11	93.02 (11)
C316—C311—C312	118.7 (3)	O12—Rh1—N11	89.38 (8)
C316—C311—P13	123.2 (2)	C14—Rh1—P13	91.59 (9)
C312—C311—P13	118.1 (2)	O12—Rh1—P13	85.95 (6)
C311—C312—C313	120.8 (3)	N11—Rh1—P13	174.36 (7)
C311—C312—H312	119.6	C02—C01—H01A	109.5
C313—C312—H312	119.6	C02—C01—H01B	109.5
C314—C313—C312	119.8 (3)	H01A—C01—H01B	109.5
C314—C313—H313	120.1	C02—C01—H01C	109.5
C312—C313—H313	120.1	H01A—C01—H01C	109.5
C313—C314—C315	119.8 (3)	H01B—C01—H01C	109.5
C313—C314—H314	120.1	O01—C02—C01	117.7 (13)
C315—C314—H314	120.1	O01—C02—C01i	110.6 (12)
C316—C315—C314	120.3 (3)	C01—C02—C01i	131.4 (9)
C316—C315—H315	119.8
N11—C2—C3—C4	−4.8 (5)	P13—C331—C336—C335	−179.2 (2)
C1—C2—C3—C4	175.4 (3)	C3—C2—N11—C111	178.5 (3)
C2—C3—C4—O12	1.8 (5)	C1—C2—N11—C111	−1.7 (4)
C2—C3—C4—C5	−177.6 (3)	C3—C2—N11—Rh1	−3.0 (4)
C116—C111—C112—C113	−2.1 (4)	C1—C2—N11—Rh1	176.8 (2)
N11—C111—C112—C113	−177.7 (3)	C116—C111—N11—C2	91.5 (3)
C116—C111—C112—C117	177.3 (3)	C112—C111—N11—C2	−92.9 (3)
N11—C111—C112—C117	1.7 (4)	C116—C111—N11—Rh1	−87.2 (3)
C111—C112—C113—C114	1.2 (4)	C112—C111—N11—Rh1	88.5 (3)
C117—C112—C113—C114	−178.3 (3)	C3—C4—O12—Rh1	9.0 (4)
C112—C113—C114—C115	0.4 (5)	C5—C4—O12—Rh1	−171.64 (18)
C113—C114—C115—C116	−1.1 (4)	C316—C311—P13—C321	9.9 (3)
C114—C115—C116—C111	0.1 (4)	C312—C311—P13—C321	−171.4 (2)
C114—C115—C116—C118	178.5 (3)	C316—C311—P13—C331	117.7 (2)
C112—C111—C116—C115	1.5 (4)	C312—C311—P13—C331	−63.6 (2)
N11—C111—C116—C115	177.1 (2)	C316—C311—P13—Rh1	−117.1 (2)
C112—C111—C116—C118	−176.9 (3)	C312—C311—P13—Rh1	61.6 (2)
N11—C111—C116—C118	−1.3 (4)	C326—C321—P13—C311	83.9 (3)
C316—C311—C312—C313	0.3 (4)	C322—C321—P13—C311	−93.4 (2)
P13—C311—C312—C313	−178.5 (2)	C326—C321—P13—C331	−23.8 (3)
C311—C312—C313—C314	0.1 (4)	C322—C321—P13—C331	158.9 (2)
C312—C313—C314—C315	−0.3 (4)	C326—C321—P13—Rh1	−145.7 (2)
C313—C314—C315—C316	0.2 (4)	C322—C321—P13—Rh1	37.0 (2)
C314—C315—C316—C311	0.1 (4)	C332—C331—P13—C311	168.3 (2)
C312—C311—C316—C315	−0.4 (4)	C336—C331—P13—C311	−12.7 (3)
P13—C311—C316—C315	178.3 (2)	C332—C331—P13—C321	−84.2 (2)
C326—C321—C322—C323	−1.5 (4)	C336—C331—P13—C321	94.8 (3)
P13—C321—C322—C323	175.9 (2)	C332—C331—P13—Rh1	38.7 (3)
C321—C322—C323—C324	2.2 (5)	C336—C331—P13—Rh1	−142.3 (2)
C322—C323—C324—C325	−1.5 (5)	C4—O12—Rh1—N11	−11.8 (2)
C323—C324—C325—C326	0.2 (6)	C4—O12—Rh1—P13	165.0 (2)
C322—C321—C326—C325	0.2 (5)	C2—N11—Rh1—C14	−170.1 (2)
P13—C321—C326—C325	−177.2 (3)	C111—N11—Rh1—C14	8.5 (2)
C324—C325—C326—C321	0.5 (6)	C2—N11—Rh1—O12	8.8 (2)
C336—C331—C332—C333	−0.9 (5)	C111—N11—Rh1—O12	−172.62 (19)
P13—C331—C332—C333	178.1 (3)	C311—P13—Rh1—C14	−14.40 (13)
C331—C332—C333—C334	2.0 (5)	C321—P13—Rh1—C14	−136.42 (13)
C332—C333—C334—C335	−2.0 (5)	C331—P13—Rh1—C14	106.57 (13)
C333—C334—C335—C336	0.9 (5)	C311—P13—Rh1—O12	166.55 (12)
C334—C335—C336—C331	0.2 (4)	C321—P13—Rh1—O12	44.53 (11)
C332—C331—C336—C335	−0.2 (4)	C331—P13—Rh1—O12	−72.48 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C332—H332···O12	0.95	2.38	3.201 (3)	144
C334—H334···O14ii	0.95	2.51	3.201 (4)	130
C1—H1B···O01iii	0.98	2.54	3.372 (9)	142

Parameters	(I)a	(II)b	(III)c	(IV)d
Rh1—N11	2.077 (2)	2.069 (2)	2.045 (4)	2.045 (3)
Rh1—O12	2.027 (2)	2.028 (2)	2.044 (3)	2.045 (2)
Rh1—P13	2.2704 (7)	2.2635 (6)	2.275 (1)	2.281 (2)
Rh1—C14	1.812 (3)	1.807 (2)	1.784 (5)	1.804 (3)
C14—O14	1.147 (3)	1.152 (3)	1.142 (7)	1.148 (4)
N11···O12	2.885 (3)	2.885 (3)	2.826 (6)	2.841 (3)
N11—Rh1—O12	89.31 (9)	89.54 (8)	87.4 (1)	87.95 (8)
O12—Rh1—P13	85.95 (6)	84.97 (5)	89.7 (1)	89.91 (5)
P13—Rh1—C14	91.57 (9)	91.87 (7)	90.3 (2)	89.48 (9)
N11—Rh1—C14	93.1 (1)	93.6 (1)	92.6 (2)	92.6 (1)
N11—C2—C4—O12	-2.6 (2)	4.1 (2)	1.2 (4)	1.5 (2)
θEe	155.77 (2)	156.39 (3)	156.0 (2)	156.23 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C332—H332⋯O12	0.95	2.38	3.201 (3)	144
C334—H334⋯O14i	0.95	2.51	3.201 (4)	130
C1—H1B⋯O01ii	0.98	2.54	3.372 (9)	142

Symmetry codes: (i) ; (ii) .

Table 2

Comparative geometrical parameters (Å, °) for similar [Rh(N,O-bid)(CO)(PPh3)] complexes

Parameters	(I)a	(II)b	(III)c	(IV)d
Rh1—N11	2.077 (2)	2.069 (2)	2.045 (4)	2.045 (3)
Rh1—O12	2.027 (2)	2.028 (2)	2.044 (3)	2.045 (2)
Rh1—P13	2.2704 (7)	2.2635 (6)	2.275 (1)	2.281 (2)
Rh1—C14	1.812 (3)	1.807 (2)	1.784 (5)	1.804 (3)
C14—O14	1.147 (3)	1.152 (3)	1.142 (7)	1.148 (4)
N11⋯O12	2.885 (3)	2.885 (3)	2.826 (6)	2.841 (3)
N11—Rh1—O12	89.31 (9)	89.54 (8)	87.4 (1)	87.95 (8)
O12—Rh1—P13	85.95 (6)	84.97 (5)	89.7 (1)	89.91 (5)
P13—Rh1—C14	91.57 (9)	91.87 (7)	90.3 (2)	89.48 (9)
N11—Rh1—C14	93.1 (1)	93.6 (1)	92.6 (2)	92.6 (1)
N11—C2—C4—O12	−2.6 (2)	4.1 (2)	1.2 (4)	1.5 (2)
θE e	155.77 (2)	156.39 (3)	156.0 (2)	156.23 (4)

Notes: (a) This work; (b) N,O-bid = 4-(2,3-dimethyl phenylamino)pent-3-en-2-onato (Venter et al., 2009 ▶); (c) N,O-bid = 4-amino-pent-3-en-2-onato (Damoense et al., 1994 ▶); (d) N,O-bid = 4-amino-1,1,1-trifluoro-pent-3-en-2-onato (Varshavsky et al., 2001 ▶); (e) cone angle (Tolman, 1977 ▶).