Carbon-yl[4-(2,3-dimethyl-phenyl-amino)pent-3-en-2-onato-κN,O](triphenyl-phosphine-κP)rhodium(I).

In the title compound, [Rh(C(13)H(16)NO)(C(18)H(15)P)(CO)], the coordination geometry of the Rh(I) atom is square-planar, formed by the coordinating N and O atoms of the bidentate enaminoketonate ligand, one C atom from the carbonyl group and a P atom from triphenyl-phosphine. The complex displays a 0.591 (3):0.409 (3) ratio disorder of the phenyl unit of the monoanionic N,O-bidentate ligand. Intra-molecular hydrogen bonding is observed between a C-H group of the triphenyl-phosphine unit and the O atom of the enamino-ketonate ligand.

Related literature

For related derclass="Chemical">ivatclass="Chemical">pan class="Chemical">ives of the 4-phenyl­amino­pent-3-en-2-onate ligand, see: Da Silva et al. (1993 ▶); Gordon et al. (2002 ▶); Shaheen et al. (2006 ▶). For related dicarbonyl rhodium(I) complexes with a bidentate ligand, see: Cornils & Herrmann (1996 ▶); Trzeciak & Ziółkowski (1994 ▶); van Rooy et al. (1995 ▶). For related carbonyl rhodium(I) complexes with a phosphine and a bidentate ligand, see: Bonati & Wilkinson (1964 ▶); Damoense et al. (1994 ▶); Lamprecht et al. (1997 ▶); Leipoldt et al. (1978 ▶); Purcell et al. (1995 ▶); Varshavsky et al. (2001 ▶). For background information, see: Tolman (1977 ▶).

Experimental

Crystal data

[class="Chemical">Rh(C13H16NO)(class="Chemical">pan class="Chemical">C18H15P)(CO)]

M = 595.46

Monoclpan class="Chemical">inclass="Chemical">pan class="Chemical">ic,

a = 14.9077 (3) Å

b = 11.6202 (3) Å

c = 16.0256 (4) Å

β = 93.521 (1)°

V = 2770.88 (11) Å3

Z = 4

Mo Kα radpan class="Chemical">iatclass="Chemical">pan class="Chemical">ion

μ = 0.70 mm−1

T = 100 K

0.25 × 0.15 × 0.13 mm

Data collection

Bruker X8 APEXclass="Chemical">Iclass="Chemical">pan class="Chemical">I 4K Kappa CCD diffractometer

Absorptclass="Chemical">ion correctclass="Chemical">pan class="Chemical">ion: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.844, T max = 0.914

30367 measured reflectpan class="Chemical">ions

6985 pan class="Chemical">indeclass="Chemical">pendent reflectclass="Chemical">pan class="Chemical">ions

5783 reflectclass="Chemical">ions wclass="Chemical">pan class="Chemical">ith I > 2σ(I)

R pan class="Chemical">int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.076

S = 1.04

6985 reflectpan class="Chemical">ions

305 parameters

H-atom parameters constrapan class="Chemical">ined

Δρmax = 0.60 e Å−3

Δρmpan class="Chemical">in = −0.69 e Å−3

Data collectclass="Chemical">ion: APEX2 (Bruker, 2007 ▶); cell refclass="Chemical">pan class="Chemical">inement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystclass="Chemical">al structure: contaclass="Chemical">pan class="Chemical">ins datablocks global, I. DOI: 10.1107/S1600536809039816/hy2218sup1.cif

Structure factors: contaclass="Chemical">ins datablocks class="Chemical">pan class="Chemical">I. DOI: 10.1107/S1600536809039816/hy2218Isup2.hkl

Addclass="Chemical">itclass="Chemical">pan class="Chemical">ional supplementary materials: crystallographic information; 3D view; checkCIF report

[Rh(C13H16NO)(C18H15P)(CO)]	F(000) = 1224
Mr = 595.46	Dx = 1.427 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8984 reflections
a = 14.9077 (3) Å	θ = 2.2–28.4°
b = 11.6202 (3) Å	µ = 0.70 mm−1
c = 16.0256 (4) Å	T = 100 K
β = 93.521 (1)°	Cuboid, yellow
V = 2770.88 (11) Å3	0.25 × 0.15 × 0.13 mm
Z = 4

Bruker X8 APEXII 4K Kappa CCD diffractometer	6985 independent reflections
Radiation source: fine-focus sealed tube	5783 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω and φ scans	θmax = 28.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→19
Tmin = 0.844, Tmax = 0.914	k = −15→14
30367 measured reflections	l = −21→18

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0235P)2 + 2.8578P] where P = (Fo2 + 2Fc2)/3
6985 reflections	(Δ/σ)max = 0.005
305 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.69 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 1033 frames were collected with a frame width of 0.5° covering up to θ = 28.41° with 99.4% completeness accomplished.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Rh1	0.258727 (11)	0.605541 (15)	1.062396 (10)	0.01882 (6)
N11	0.26580 (15)	0.43296 (18)	1.03172 (15)	0.0361 (5)
O12	0.36554 (10)	0.63702 (14)	0.99328 (9)	0.0221 (3)
O14	0.09801 (11)	0.57318 (15)	1.15945 (10)	0.0285 (4)
P13	0.26175 (4)	0.79721 (5)	1.08760 (3)	0.01818 (12)
C1	0.3204 (2)	0.2591 (2)	0.9641 (2)	0.0576 (10)
H1A	0.3099	0.218	1.0161	0.086*
H1B	0.3782	0.2352	0.9439	0.086*
H1C	0.2722	0.2409	0.9219	0.086*
C2	0.32179 (18)	0.3869 (2)	0.98045 (17)	0.0325 (6)
C3	0.38454 (16)	0.4508 (2)	0.93713 (15)	0.0267 (5)
H3	0.4176	0.4093	0.8982	0.032*
C4	0.40317 (14)	0.5655 (2)	0.94473 (14)	0.0222 (5)
C5	0.47221 (16)	0.6203 (2)	0.89254 (16)	0.0318 (6)
H5A	0.4419	0.6684	0.8492	0.048*
H5B	0.5068	0.5601	0.8662	0.048*
H5C	0.5129	0.668	0.9283	0.048*
C11A	0.22412 (17)	0.3512 (2)	1.08695 (16)	0.0249 (5)	0.591 (3)
C12A	0.13769 (16)	0.3169 (2)	1.06046 (13)	0.0249 (5)	0.591 (3)
C13A	0.09120 (13)	0.2400 (2)	1.10833 (15)	0.0249 (5)	0.591 (3)
C14A	0.13113 (16)	0.1974 (2)	1.18269 (14)	0.0249 (5)	0.591 (3)
H14A	0.0994	0.1449	1.2154	0.03*	0.591 (3)
C15A	0.21756 (17)	0.2318 (2)	1.20919 (14)	0.0249 (5)	0.591 (3)
H15A	0.2449	0.2027	1.26	0.03*	0.591 (3)
C16A	0.26405 (14)	0.3086 (3)	1.16132 (17)	0.0249 (5)	0.591 (3)
H16A	0.3231	0.3321	1.1794	0.03*	0.591 (3)
C18A	−0.0011 (3)	0.1950 (4)	1.0797 (2)	0.0249 (5)	0.591 (3)
H18A	0.0043	0.1423	1.0325	0.037*	0.591 (3)
H18B	−0.0401	0.2596	1.0622	0.037*	0.591 (3)
H18C	−0.0271	0.1539	1.1258	0.037*	0.591 (3)
C17A	0.0953 (3)	0.3664 (4)	0.9799 (3)	0.0249 (5)	0.591 (3)
H17A	0.0902	0.4501	0.9853	0.037*	0.591 (3)
H17B	0.0354	0.333	0.9688	0.037*	0.591 (3)
H17C	0.1329	0.348	0.9337	0.037*	0.591 (3)
C11B	0.1803 (2)	0.3671 (3)	1.0474 (2)	0.0243 (7)	0.409 (3)
C12B	0.18861 (19)	0.3040 (3)	1.1212 (2)	0.0243 (7)	0.409 (3)
C13B	0.1158 (2)	0.2418 (3)	1.14741 (19)	0.0243 (7)	0.409 (3)
C14B	0.0346 (2)	0.2428 (3)	1.0998 (2)	0.0243 (7)	0.409 (3)
H14B	−0.0152	0.2003	1.1178	0.029*	0.409 (3)
C15B	0.0263 (2)	0.3059 (3)	1.0261 (2)	0.0243 (7)	0.409 (3)
H15B	−0.0292	0.3065	0.9936	0.029*	0.409 (3)
C16B	0.0991 (3)	0.3680 (3)	0.99988 (19)	0.0243 (7)	0.409 (3)
H16B	0.0934	0.4111	0.9495	0.029*	0.409 (3)
C17B	0.2760 (4)	0.3064 (6)	1.1737 (4)	0.0243 (7)	0.409 (3)
H17D	0.3093	0.2351	1.165	0.036*	0.409 (3)
H17E	0.2636	0.3132	1.2328	0.036*	0.409 (3)
H17F	0.3119	0.3724	1.1574	0.036*	0.409 (3)
C18B	0.1219 (4)	0.1738 (5)	1.2287 (3)	0.0243 (7)	0.409 (3)
H18D	0.0624	0.144	1.2399	0.036*	0.409 (3)
H18E	0.1436	0.2241	1.2747	0.036*	0.409 (3)
H18F	0.1638	0.1094	1.2238	0.036*	0.409 (3)
C14	0.16135 (15)	0.58652 (19)	1.12283 (14)	0.0215 (5)
C311	0.19823 (15)	0.8522 (2)	1.17253 (14)	0.0212 (5)
C312	0.23991 (16)	0.8923 (2)	1.24725 (15)	0.0261 (5)
H312	0.3036	0.898	1.2531	0.031*
C313	0.18891 (18)	0.9239 (2)	1.31310 (16)	0.0336 (6)
H313	0.2177	0.9501	1.3642	0.04*
C314	0.09599 (18)	0.9173 (2)	1.30437 (17)	0.0372 (6)
H314	0.0611	0.9395	1.3493	0.045*
C315	0.05421 (17)	0.8787 (2)	1.23056 (18)	0.0364 (6)
H315	−0.0095	0.8745	1.2248	0.044*
C316	0.10419 (16)	0.8460 (2)	1.16490 (16)	0.0289 (5)
H316	0.0748	0.8192	1.1143	0.035*
C321	0.22426 (16)	0.8831 (2)	0.99645 (14)	0.0239 (5)
C322	0.17703 (18)	0.9858 (2)	1.00150 (15)	0.0329 (6)
H322	0.1615	1.014	1.0544	0.04*
C323	0.1525 (2)	1.0472 (2)	0.92915 (17)	0.0409 (7)
H323	0.1194	1.1167	0.9329	0.049*
C324	0.1756 (2)	1.0084 (2)	0.85193 (16)	0.0383 (6)
H324	0.1591	1.0511	0.8028	0.046*
C325	0.22301 (19)	0.9068 (2)	0.84678 (16)	0.0362 (6)
H325	0.2393	0.8796	0.7939	0.043*
C326	0.24695 (16)	0.8442 (2)	0.91864 (14)	0.0280 (5)
H326	0.2791	0.7741	0.9144	0.034*
C331	0.37540 (15)	0.8504 (2)	1.11391 (13)	0.0224 (5)
C332	0.40227 (19)	0.9603 (2)	1.09345 (18)	0.0389 (7)
H332	0.3623	1.0096	1.0618	0.047*
C333	0.4886 (2)	0.9988 (3)	1.1196 (2)	0.0510 (8)
H333	0.5073	1.074	1.1053	0.061*
C334	0.54615 (18)	0.9282 (3)	1.16566 (18)	0.0431 (8)
H334	0.6043	0.955	1.1839	0.052*
C335	0.52026 (16)	0.8193 (3)	1.18548 (16)	0.0353 (6)
H335	0.5605	0.7705	1.2172	0.042*
C336	0.43533 (15)	0.7797 (2)	1.15942 (14)	0.0264 (5)
H336	0.4181	0.7035	1.1729	0.032*

	U11	U22	U33	U12	U13	U23
Rh1	0.01877 (9)	0.01664 (9)	0.02180 (9)	−0.00199 (7)	0.00727 (6)	−0.00079 (7)
N11	0.0465 (13)	0.0177 (10)	0.0478 (13)	−0.0072 (9)	0.0327 (11)	−0.0047 (9)
O12	0.0197 (8)	0.0216 (8)	0.0256 (8)	0.0005 (6)	0.0075 (6)	0.0035 (6)
O14	0.0241 (9)	0.0315 (10)	0.0309 (9)	−0.0077 (7)	0.0108 (7)	−0.0045 (7)
P13	0.0172 (3)	0.0182 (3)	0.0191 (3)	−0.0007 (2)	0.0002 (2)	−0.0006 (2)
C1	0.083 (2)	0.0238 (15)	0.073 (2)	−0.0050 (15)	0.055 (2)	−0.0111 (15)
C2	0.0384 (14)	0.0220 (13)	0.0393 (14)	−0.0005 (11)	0.0201 (12)	−0.0043 (11)
C3	0.0271 (12)	0.0248 (13)	0.0297 (12)	0.0038 (10)	0.0134 (10)	−0.0004 (10)
C4	0.0169 (10)	0.0277 (12)	0.0223 (11)	0.0033 (9)	0.0038 (9)	0.0054 (9)
C5	0.0247 (12)	0.0372 (15)	0.0349 (13)	−0.0004 (11)	0.0128 (10)	0.0068 (11)
C11A	0.0258 (8)	0.0232 (8)	0.0259 (8)	−0.0024 (6)	0.0018 (6)	0.0011 (6)
C12A	0.0258 (8)	0.0232 (8)	0.0259 (8)	−0.0024 (6)	0.0018 (6)	0.0011 (6)
C13A	0.0258 (8)	0.0232 (8)	0.0259 (8)	−0.0024 (6)	0.0018 (6)	0.0011 (6)
C14A	0.0258 (8)	0.0232 (8)	0.0259 (8)	−0.0024 (6)	0.0018 (6)	0.0011 (6)
C15A	0.0258 (8)	0.0232 (8)	0.0259 (8)	−0.0024 (6)	0.0018 (6)	0.0011 (6)
C16A	0.0258 (8)	0.0232 (8)	0.0259 (8)	−0.0024 (6)	0.0018 (6)	0.0011 (6)
C18A	0.0258 (8)	0.0232 (8)	0.0259 (8)	−0.0024 (6)	0.0018 (6)	0.0011 (6)
C17A	0.0258 (8)	0.0232 (8)	0.0259 (8)	−0.0024 (6)	0.0018 (6)	0.0011 (6)
C11B	0.0281 (12)	0.0204 (11)	0.0246 (11)	0.0016 (9)	0.0036 (9)	0.0003 (8)
C12B	0.0281 (12)	0.0204 (11)	0.0246 (11)	0.0016 (9)	0.0036 (9)	0.0003 (8)
C13B	0.0281 (12)	0.0204 (11)	0.0246 (11)	0.0016 (9)	0.0036 (9)	0.0003 (8)
C14B	0.0281 (12)	0.0204 (11)	0.0246 (11)	0.0016 (9)	0.0036 (9)	0.0003 (8)
C15B	0.0281 (12)	0.0204 (11)	0.0246 (11)	0.0016 (9)	0.0036 (9)	0.0003 (8)
C16B	0.0281 (12)	0.0204 (11)	0.0246 (11)	0.0016 (9)	0.0036 (9)	0.0003 (8)
C17B	0.0281 (12)	0.0204 (11)	0.0246 (11)	0.0016 (9)	0.0036 (9)	0.0003 (8)
C18B	0.0281 (12)	0.0204 (11)	0.0246 (11)	0.0016 (9)	0.0036 (9)	0.0003 (8)
C14	0.0238 (11)	0.0192 (12)	0.0216 (11)	−0.0045 (9)	0.0027 (9)	−0.0031 (9)
C311	0.0201 (11)	0.0193 (11)	0.0242 (11)	0.0002 (9)	0.0009 (9)	−0.0020 (9)
C312	0.0232 (12)	0.0279 (13)	0.0267 (12)	0.0035 (10)	−0.0017 (9)	−0.0048 (10)
C313	0.0363 (14)	0.0400 (16)	0.0242 (12)	0.0017 (12)	−0.0009 (11)	−0.0116 (11)
C314	0.0320 (14)	0.0462 (17)	0.0345 (14)	0.0044 (12)	0.0106 (11)	−0.0135 (12)
C315	0.0201 (12)	0.0439 (17)	0.0459 (16)	−0.0004 (11)	0.0072 (11)	−0.0112 (13)
C316	0.0235 (12)	0.0312 (14)	0.0319 (13)	−0.0013 (10)	0.0007 (10)	−0.0085 (11)
C321	0.0280 (12)	0.0199 (12)	0.0231 (11)	−0.0001 (10)	−0.0034 (9)	−0.0003 (9)
C322	0.0483 (16)	0.0230 (13)	0.0267 (12)	0.0066 (12)	−0.0043 (11)	−0.0046 (10)
C323	0.0585 (19)	0.0243 (14)	0.0386 (15)	0.0148 (13)	−0.0064 (14)	0.0002 (11)
C324	0.0529 (18)	0.0312 (15)	0.0298 (13)	0.0095 (13)	−0.0065 (12)	0.0074 (11)
C325	0.0469 (16)	0.0383 (16)	0.0230 (12)	0.0103 (13)	−0.0008 (11)	0.0022 (11)
C326	0.0340 (14)	0.0248 (13)	0.0246 (12)	0.0081 (10)	−0.0023 (10)	0.0009 (10)
C331	0.0200 (11)	0.0286 (12)	0.0190 (10)	−0.0059 (9)	0.0035 (9)	−0.0027 (9)
C332	0.0405 (16)	0.0334 (16)	0.0423 (15)	−0.0137 (12)	−0.0020 (13)	0.0053 (12)
C333	0.0503 (19)	0.0486 (19)	0.0550 (19)	−0.0328 (16)	0.0110 (15)	−0.0046 (16)
C334	0.0240 (13)	0.067 (2)	0.0387 (15)	−0.0154 (14)	0.0085 (12)	−0.0198 (15)
C335	0.0194 (12)	0.0592 (19)	0.0276 (12)	0.0007 (12)	0.0031 (10)	−0.0165 (12)
C336	0.0212 (11)	0.0368 (14)	0.0215 (11)	−0.0014 (10)	0.0050 (9)	−0.0095 (10)

Rh1—C14	1.807 (2)	C13B—C18B	1.522 (6)
Rh1—O12	2.0280 (15)	C14B—C15B	1.39
Rh1—N11	2.069 (2)	C14B—H14B	0.95
Rh1—P13	2.2635 (6)	C15B—C16B	1.39
N11—C2	1.320 (3)	C15B—H15B	0.95
N11—C11A	1.463 (3)	C16B—H16B	0.95
N11—C11B	1.522 (3)	C17B—H17D	0.98
O12—C4	1.290 (3)	C17B—H17E	0.98
O14—C14	1.152 (3)	C17B—H17F	0.98
P13—C311	1.821 (2)	C18B—H18D	0.98
P13—C331	1.828 (2)	C18B—H18E	0.98
P13—C321	1.828 (2)	C18B—H18F	0.98
C1—C2	1.508 (4)	C311—C312	1.395 (3)
C1—H1A	0.98	C311—C316	1.401 (3)
C1—H1B	0.98	C312—C313	1.388 (3)
C1—H1C	0.98	C312—H312	0.95
C2—C3	1.410 (3)	C313—C314	1.386 (4)
C3—C4	1.366 (3)	C313—H313	0.95
C3—H3	0.95	C314—C315	1.378 (4)
C4—C5	1.507 (3)	C314—H314	0.95
C5—H5A	0.98	C315—C316	1.379 (3)
C5—H5B	0.98	C315—H315	0.95
C5—H5C	0.98	C316—H316	0.95
C11A—C12A	1.39	C321—C326	1.388 (3)
C11A—C16A	1.39	C321—C322	1.390 (3)
C12A—C13A	1.39	C322—C323	1.391 (4)
C12A—C17A	1.515 (5)	C322—H322	0.95
C13A—C14A	1.39	C323—C324	1.381 (4)
C13A—C18A	1.516 (4)	C323—H323	0.95
C14A—C15A	1.39	C324—C325	1.380 (4)
C14A—H14A	0.95	C324—H324	0.95
C15A—C16A	1.39	C325—C326	1.390 (3)
C15A—H15A	0.95	C325—H325	0.95
C16A—H16A	0.95	C326—H326	0.95
C18A—H18A	0.98	C331—C332	1.384 (4)
C18A—H18B	0.98	C331—C336	1.388 (3)
C18A—H18C	0.98	C332—C333	1.403 (4)
C17A—H17A	0.98	C332—H332	0.95
C17A—H17B	0.98	C333—C334	1.369 (5)
C17A—H17C	0.98	C333—H333	0.95
C11B—C12B	1.39	C334—C335	1.366 (4)
C11B—C16B	1.39	C334—H334	0.95
C12B—C13B	1.39	C335—C336	1.387 (3)
C12B—C17B	1.506 (7)	C335—H335	0.95
C13B—C14B	1.39	C336—H336	0.95
C14—Rh1—O12	176.48 (9)	C14B—C15B—H15B	120
C14—Rh1—N11	93.62 (9)	C15B—C16B—C11B	120
O12—Rh1—N11	89.53 (7)	C15B—C16B—H16B	120
C14—Rh1—P13	91.86 (7)	C11B—C16B—H16B	120
O12—Rh1—P13	84.97 (5)	C12B—C17B—H17D	109.5
N11—Rh1—P13	174.49 (6)	C12B—C17B—H17E	109.5
C2—N11—C11A	114.9 (2)	H17D—C17B—H17E	109.5
C2—N11—C11B	117.8 (2)	C12B—C17B—H17F	109.5
C2—N11—Rh1	125.77 (17)	H17D—C17B—H17F	109.5
C11A—N11—Rh1	117.14 (17)	H17E—C17B—H17F	109.5
C11B—N11—Rh1	113.14 (19)	C13B—C18B—H18D	109.5
C4—O12—Rh1	126.75 (15)	C13B—C18B—H18E	109.5
C311—P13—C331	103.07 (10)	H18D—C18B—H18E	109.5
C311—P13—C321	104.96 (11)	C13B—C18B—H18F	109.5
C331—P13—C321	103.48 (11)	H18D—C18B—H18F	109.5
C311—P13—Rh1	118.23 (8)	H18E—C18B—H18F	109.5
C331—P13—Rh1	112.44 (8)	O14—C14—Rh1	178.1 (2)
C321—P13—Rh1	113.14 (8)	C312—C311—C316	118.8 (2)
C2—C1—H1A	109.5	C312—C311—P13	122.29 (17)
C2—C1—H1B	109.5	C316—C311—P13	118.70 (17)
H1A—C1—H1B	109.5	C313—C312—C311	120.4 (2)
C2—C1—H1C	109.5	C313—C312—H312	119.8
H1A—C1—H1C	109.5	C311—C312—H312	119.8
H1B—C1—H1C	109.5	C314—C313—C312	120.0 (2)
N11—C2—C3	123.8 (2)	C314—C313—H313	120
N11—C2—C1	120.3 (2)	C312—C313—H313	120
C3—C2—C1	115.8 (2)	C315—C314—C313	120.1 (2)
C4—C3—C2	127.4 (2)	C315—C314—H314	120
C4—C3—H3	116.3	C313—C314—H314	120
C2—C3—H3	116.3	C314—C315—C316	120.5 (2)
O12—C4—C3	126.1 (2)	C314—C315—H315	119.7
O12—C4—C5	113.6 (2)	C316—C315—H315	119.7
C3—C4—C5	120.3 (2)	C315—C316—C311	120.2 (2)
C4—C5—H5A	109.5	C315—C316—H316	119.9
C4—C5—H5B	109.5	C311—C316—H316	119.9
H5A—C5—H5B	109.5	C326—C321—C322	119.0 (2)
C4—C5—H5C	109.5	C326—C321—P13	117.40 (18)
H5A—C5—H5C	109.5	C322—C321—P13	123.59 (18)
H5B—C5—H5C	109.5	C321—C322—C323	120.0 (2)
C12A—C11A—C16A	120	C321—C322—H322	120
C12A—C11A—N11	114.94 (19)	C323—C322—H322	120
C16A—C11A—N11	125.06 (19)	C324—C323—C322	120.8 (2)
C11A—C12A—C13A	120	C324—C323—H323	119.6
C11A—C12A—C17A	118.8 (2)	C322—C323—H323	119.6
C13A—C12A—C17A	121.2 (2)	C325—C324—C323	119.3 (2)
C12A—C13A—C14A	120	C325—C324—H324	120.3
C12A—C13A—C18A	121.9 (2)	C323—C324—H324	120.3
C14A—C13A—C18A	118.0 (2)	C324—C325—C326	120.3 (2)
C15A—C14A—C13A	120	C324—C325—H325	119.9
C15A—C14A—H14A	120	C326—C325—H325	119.9
C13A—C14A—H14A	120	C321—C326—C325	120.6 (2)
C14A—C15A—C16A	120	C321—C326—H326	119.7
C14A—C15A—H15A	120	C325—C326—H326	119.7
C16A—C15A—H15A	120	C332—C331—C336	119.0 (2)
C15A—C16A—C11A	120	C332—C331—P13	122.3 (2)
C15A—C16A—H16A	120	C336—C331—P13	118.61 (18)
C11A—C16A—H16A	120	C331—C332—C333	119.8 (3)
C12B—C11B—C16B	120	C331—C332—H332	120.1
C12B—C11B—N11	112.0 (2)	C333—C332—H332	120.1
C16B—C11B—N11	128.0 (2)	C334—C333—C332	120.2 (3)
C11B—C12B—C13B	120	C334—C333—H333	119.9
C11B—C12B—C17B	119.6 (3)	C332—C333—H333	119.9
C13B—C12B—C17B	120.4 (3)	C335—C334—C333	120.3 (3)
C14B—C13B—C12B	120	C335—C334—H334	119.9
C14B—C13B—C18B	118.6 (3)	C333—C334—H334	119.9
C12B—C13B—C18B	121.4 (3)	C334—C335—C336	120.2 (3)
C13B—C14B—C15B	120	C334—C335—H335	119.9
C13B—C14B—H14B	120	C336—C335—H335	119.9
C15B—C14B—H14B	120	C335—C336—C331	120.5 (3)
C16B—C15B—C14B	120	C335—C336—H336	119.7
C16B—C15B—H15B	120	C331—C336—H336	119.7
C14—Rh1—N11—C2	174.7 (3)	C16B—C11B—C12B—C17B	−178.1 (4)
O12—Rh1—N11—C2	−3.8 (3)	N11—C11B—C12B—C17B	−0.6 (4)
C14—Rh1—N11—C11A	−23.0 (2)	C11B—C12B—C13B—C14B	0
O12—Rh1—N11—C11A	158.5 (2)	C17B—C12B—C13B—C14B	178.1 (4)
C14—Rh1—N11—C11B	15.6 (2)	C11B—C12B—C13B—C18B	−178.8 (4)
O12—Rh1—N11—C11B	−162.8 (2)	C17B—C12B—C13B—C18B	−0.7 (5)
N11—Rh1—O12—C4	8.13 (19)	C12B—C13B—C14B—C15B	0
P13—Rh1—O12—C4	−171.45 (18)	C18B—C13B—C14B—C15B	178.8 (4)
C14—Rh1—P13—C311	16.41 (11)	C13B—C14B—C15B—C16B	0
O12—Rh1—P13—C311	−165.13 (10)	C14B—C15B—C16B—C11B	0
C14—Rh1—P13—C331	136.38 (11)	C12B—C11B—C16B—C15B	0
O12—Rh1—P13—C331	−45.16 (9)	N11—C11B—C16B—C15B	−177.0 (4)
C14—Rh1—P13—C321	−106.82 (11)	C331—P13—C311—C312	−16.6 (2)
O12—Rh1—P13—C321	71.63 (10)	C321—P13—C311—C312	−124.6 (2)
C11A—N11—C2—C3	−164.1 (3)	Rh1—P13—C311—C312	108.17 (19)
C11B—N11—C2—C3	156.7 (3)	C331—P13—C311—C316	168.3 (2)
Rh1—N11—C2—C3	−1.5 (4)	C321—P13—C311—C316	60.2 (2)
C11A—N11—C2—C1	16.8 (4)	Rh1—P13—C311—C316	−67.0 (2)
C11B—N11—C2—C1	−22.4 (4)	C316—C311—C312—C313	0.9 (4)
Rh1—N11—C2—C1	179.4 (2)	P13—C311—C312—C313	−174.3 (2)
N11—C2—C3—C4	5.4 (5)	C311—C312—C313—C314	−0.9 (4)
C1—C2—C3—C4	−175.5 (3)	C312—C313—C314—C315	0.4 (4)
Rh1—O12—C4—C3	−7.5 (3)	C313—C314—C315—C316	0.1 (5)
Rh1—O12—C4—C5	171.45 (15)	C314—C315—C316—C311	−0.2 (4)
C2—C3—C4—O12	−0.5 (4)	C312—C311—C316—C315	−0.3 (4)
C2—C3—C4—C5	−179.4 (3)	P13—C311—C316—C315	175.1 (2)
C2—N11—C11A—C12A	−98.8 (3)	C311—P13—C321—C326	−166.46 (19)
C11B—N11—C11A—C12A	4.8 (3)	C331—P13—C321—C326	85.8 (2)
Rh1—N11—C11A—C12A	97.0 (2)	Rh1—P13—C321—C326	−36.2 (2)
C2—N11—C11A—C16A	81.7 (3)	C311—P13—C321—C322	15.4 (2)
C11B—N11—C11A—C16A	−174.7 (4)	C331—P13—C321—C322	−92.3 (2)
Rh1—N11—C11A—C16A	−82.5 (2)	Rh1—P13—C321—C322	145.7 (2)
C16A—C11A—C12A—C13A	0	C326—C321—C322—C323	0.6 (4)
N11—C11A—C12A—C13A	−179.5 (3)	P13—C321—C322—C323	178.7 (2)
C16A—C11A—C12A—C17A	178.9 (3)	C321—C322—C323—C324	−1.0 (4)
N11—C11A—C12A—C17A	−0.6 (3)	C322—C323—C324—C325	0.6 (5)
C11A—C12A—C13A—C14A	0	C323—C324—C325—C326	0.2 (5)
C17A—C12A—C13A—C14A	−178.9 (3)	C322—C321—C326—C325	0.1 (4)
C11A—C12A—C13A—C18A	−176.5 (3)	P13—C321—C326—C325	−178.1 (2)
C17A—C12A—C13A—C18A	4.6 (4)	C324—C325—C326—C321	−0.5 (4)
C12A—C13A—C14A—C15A	0	C311—P13—C331—C332	−83.3 (2)
C18A—C13A—C14A—C15A	176.7 (3)	C321—P13—C331—C332	25.9 (2)
C13A—C14A—C15A—C16A	0	Rh1—P13—C331—C332	148.32 (19)
C14A—C15A—C16A—C11A	0	C311—P13—C331—C336	93.63 (19)
C12A—C11A—C16A—C15A	0	C321—P13—C331—C336	−157.22 (18)
N11—C11A—C16A—C15A	179.5 (3)	Rh1—P13—C331—C336	−34.78 (19)
C2—N11—C11B—C12B	98.0 (3)	C336—C331—C332—C333	−0.7 (4)
C11A—N11—C11B—C12B	3.6 (3)	P13—C331—C332—C333	176.2 (2)
Rh1—N11—C11B—C12B	−101.2 (2)	C331—C332—C333—C334	−0.4 (4)
C2—N11—C11B—C16B	−84.8 (3)	C332—C333—C334—C335	0.9 (4)
C11A—N11—C11B—C16B	−179.2 (5)	C333—C334—C335—C336	−0.3 (4)
Rh1—N11—C11B—C16B	76.1 (3)	C334—C335—C336—C331	−0.8 (3)
C16B—C11B—C12B—C13B	0	C332—C331—C336—C335	1.3 (3)
N11—C11B—C12B—C13B	177.5 (3)	P13—C331—C336—C335	−175.74 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C326—H326···O12	0.95	2.36	3.177 (3)	143

Parameters	(I)	(II)	(III)
Rh1—N11	2.069 (2)	2.045 (4)	2.045 (3)
Rh1—O12	2.028 (2)	2.044 (3)	2.045 (2)
Rh1—P13	2.2635 (6)	2.275 (1)	2.281 (2)
Rh1—C14	1.807 (2)	1.784 (5)	1.804 (3)
C14—O14	1.152 (3)	1.142 (7)	1.148 (4)
N11···O12	2.885 (3)	2.826 (6)	2.841 (3)
N11—Rh1—O12	89.54 (8)	87.4 (1)	87.95 (8)
O12—Rh1—P13	84.97 (5)	89.7 (1)	89.91 (5)
P13—Rh1—C14	91.87 (7)	90.3 (2)	89.48 (9)
N11—Rh1—C14	93.6 (1)	92.6 (2)	92.6 (1)
N11—C2—C4—O12	4.1 (2)	1.2 (4)	1.5 (2)
θE (Tolman, 1977)	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
C326—H326⋯O12	0.95	2.36	3.177 (3)	143

Table 2

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

Parameters	(I)	(II)	(III)
Rh1—N11	2.069 (2)	2.045 (4)	2.045 (3)
Rh1—O12	2.028 (2)	2.044 (3)	2.045 (2)
Rh1—P13	2.2635 (6)	2.275 (1)	2.281 (2)
Rh1—C14	1.807 (2)	1.784 (5)	1.804 (3)
C14—O14	1.152 (3)	1.142 (7)	1.148 (4)
N11⋯O12	2.885 (3)	2.826 (6)	2.841 (3)
N11—Rh1—O12	89.54 (8)	87.4 (1)	87.95 (8)
O12—Rh1—P13	84.97 (5)	89.7 (1)	89.91 (5)
P13—Rh1—C14	91.87 (7)	90.3 (2)	89.48 (9)
N11—Rh1—C14	93.6 (1)	92.6 (2)	92.6 (1)
N11—C2—C4—O12	4.1 (2)	1.2 (4)	1.5 (2)
θEa	156.39 (3)	156.0 (2)	156.23 (4)

Notes: (I) This work. (II) N,O-bid = 4-aminopent-3-en-2-onato (Damoense et al., 1994 ▶). (III) N,O-bid = 4-amino-1,1,1-trifluoropent-3-en-2-onato (Varshavsky et al., 2001 ▶). (a) Tolman (1977 ▶)