Carbon-yl(N-nitroso-N-oxido-1-naphtylamine-κO,O')(triphenyl-phosphine-κP)rhodium(I) acetone solvate.

The title compound, [Rh(C(10)H(7)N(2)O(2))(C(18)H(15)P)(CO)]·(CH(3))(2)CO, is the second structural report of a metal complex formed with the O,O'-C(10)H(7)N(2)O(2) (neocupferrate) ligand. In the crystal structure, the metal centre is surrounded by one carbonyl ligand, one triphenyl-phosphine ligand and the bidentate neocupferrate ligand, forming a distorted square-planar RhCO(2)P coordination set which is best illustrated by the small O-Rh-O bite angle of 77.74 (10)°. There are no classical hydrogen-bond inter-actions observed for this complex.

Related literature

For synthesis of similar Rh complexes and information on oxidative addition products, see: Basson et al. (1984 ▶, 1986 ▶); Steyn et al. (1992 ▶); Smit et al. (1994 ▶); Roodt & Steyn (2000 ▶). For another structural report of a complex with the bidentate neocupferrate ligand, see: Tamaki & Okabe (1998 ▶).

Experimental

Crystal data

[Rh(C10H7N2O2)(C18H15P)(CO)]·C3H6O

M = 638.44

Triclinic,

a = 9.709 (5) Å

b = 10.186 (5) Å

c = 15.393 (5) Å

α = 77.499 (5)°

β = 85.045 (5)°

γ = 70.279 (5)°

V = 1398.9 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.71 mm−1

T = 100 K

0.21 × 0.21 × 0.08 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan SADABS (Bruker, 2004 ▶) T min = 0.763, T max = 0.847

23989 measured reflections

6710 independent reflections

5377 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.157

S = 1.16

6710 reflections

363 parameters

H-atom parameters constrained

Δρmax = 1.75 e Å−3

Δρmin = −1.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); 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/S1600536809047321/wm2279sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047321/wm2279Isup2.hkl

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

[Rh(C10H7N2O2)(C18H15P)(CO)]·C3H6O	Z = 2
Mr = 638.44	F(000) = 652
Triclinic, P1	Dx = 1.516 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 9.709 (5) Å	Cell parameters from 5578 reflections
b = 10.186 (5) Å	θ = 2.1–28.1°
c = 15.393 (5) Å	µ = 0.71 mm−1
α = 77.499 (5)°	T = 100 K
β = 85.045 (5)°	Plate, yellow
γ = 70.279 (5)°	0.21 × 0.21 × 0.08 mm
V = 1398.9 (11) Å3

Bruker X8 APEXII 4K Kappa CCD diffractometer	6710 independent reflections
Radiation source: sealed tube	5377 reflections with I > 2σ(I)
graphite	Rint = 0.053
φ and ω scans	θmax = 28°, θmin = 1.4°
Absorption correction: multi-scan SADABS (Bruker, 2004)	h = −11→12
Tmin = 0.763, Tmax = 0.847	k = −13→13
23989 measured reflections	l = −19→20

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047	w = 1/[σ2(Fo2) + (0.0853P)2 + 0.0168P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.157	(Δ/σ)max = 0.001
S = 1.16	Δρmax = 1.75 e Å−3
6710 reflections	Δρmin = −1.18 e Å−3
363 parameters

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
C1	0.6328 (4)	0.0332 (4)	0.3430 (2)	0.0177 (8)
C2	1.0765 (4)	0.7216 (5)	0.1312 (3)	0.0239 (9)
C3	1.1293 (5)	0.8324 (5)	0.1536 (3)	0.0319 (10)
H3A	1.0737	0.9245	0.1213	0.048*
H3B	1.2309	0.8127	0.1374	0.048*
H3C	1.117	0.8308	0.2163	0.048*
C4	1.1869 (5)	0.5745 (5)	0.1384 (3)	0.0377 (12)
H4A	1.1384	0.509	0.1324	0.057*
H4B	1.2329	0.5453	0.1954	0.057*
H4C	1.2597	0.5754	0.0922	0.057*
C11	0.6713 (4)	0.2154 (4)	0.1495 (2)	0.0142 (7)
C12	0.7244 (4)	0.0790 (4)	0.1287 (2)	0.0181 (8)
H12	0.7963	0.0068	0.1637	0.022*
C13	0.6713 (4)	0.0515 (4)	0.0572 (3)	0.0203 (8)
H13	0.7079	−0.039	0.0439	0.024*
C14	0.5630 (4)	0.1580 (4)	0.0043 (2)	0.0203 (8)
H14	0.5281	0.1394	−0.0445	0.024*
C15	0.5083 (4)	0.2912 (4)	0.0251 (2)	0.0206 (8)
H15	0.4347	0.3622	−0.0093	0.025*
C16	0.5624 (4)	0.3204 (4)	0.0974 (2)	0.0170 (8)
H16	0.525	0.4109	0.1106	0.02*
C21	0.9422 (4)	0.2162 (4)	0.2069 (2)	0.0165 (8)
C22	1.0527 (4)	0.1445 (4)	0.2703 (2)	0.0162 (8)
H22	1.0277	0.1147	0.3292	0.019*
C23	1.2001 (4)	0.1179 (4)	0.2450 (3)	0.0198 (8)
H23	1.2726	0.0712	0.2873	0.024*
C24	1.2381 (4)	0.1601 (4)	0.1585 (3)	0.0205 (8)
H24	1.3362	0.1417	0.1422	0.025*
C25	1.1307 (5)	0.2304 (4)	0.0950 (3)	0.0221 (9)
H25	1.1571	0.2592	0.0363	0.027*
C26	0.9827 (4)	0.2581 (4)	0.1189 (3)	0.0204 (8)
H26	0.9112	0.3047	0.076	0.024*
C31	0.6668 (4)	0.4369 (4)	0.2389 (2)	0.0158 (8)
C32	0.7292 (4)	0.5387 (4)	0.1976 (2)	0.0171 (8)
H32	0.8199	0.5111	0.1692	0.021*
C33	0.6579 (4)	0.6807 (4)	0.1984 (3)	0.0198 (8)
H33	0.7011	0.7482	0.171	0.024*
C34	0.5219 (5)	0.7233 (4)	0.2398 (3)	0.0215 (9)
H34	0.4733	0.8193	0.2395	0.026*
C35	0.4598 (4)	0.6231 (4)	0.2813 (2)	0.0198 (8)
H35	0.3687	0.6511	0.3091	0.024*
C36	0.5321 (4)	0.4806 (4)	0.2818 (2)	0.0186 (8)
H36	0.4901	0.4131	0.3111	0.022*
C41	0.8788 (4)	0.3118 (4)	0.5592 (2)	0.0150 (8)
C42	1.0024 (4)	0.2448 (4)	0.6094 (2)	0.0184 (8)
H42	1.047	0.1468	0.6171	0.022*
C43	1.0612 (4)	0.3262 (4)	0.6493 (2)	0.0215 (9)
H43	1.1461	0.2824	0.6825	0.026*
C44	0.9926 (4)	0.4700 (4)	0.6387 (2)	0.0206 (8)
H44	1.0319	0.5229	0.6652	0.025*
C45	0.8626 (4)	0.5407 (4)	0.5882 (2)	0.0172 (8)
C46	0.8031 (4)	0.4598 (4)	0.5459 (2)	0.0143 (7)
C47	0.6743 (4)	0.5309 (4)	0.4946 (2)	0.0165 (8)
H47	0.6355	0.4796	0.4664	0.02*
C48	0.6073 (4)	0.6744 (4)	0.4867 (3)	0.0202 (8)
H48	0.5224	0.7197	0.4537	0.024*
C49	0.6656 (4)	0.7544 (4)	0.5281 (3)	0.0211 (9)
H49	0.6189	0.852	0.5221	0.025*
C50	0.7902 (4)	0.6894 (4)	0.5769 (2)	0.0192 (8)
H50	0.8281	0.7437	0.6032	0.023*
N1	0.8228 (3)	0.2270 (3)	0.51666 (19)	0.0141 (6)
N7	0.7762 (3)	0.1307 (3)	0.5647 (2)	0.0165 (7)
O1	0.5680 (3)	−0.0262 (3)	0.31778 (19)	0.0293 (7)
O2	0.8240 (3)	0.2552 (3)	0.42710 (16)	0.0162 (6)
O3	0.7281 (3)	0.0595 (3)	0.51892 (16)	0.0172 (6)
O4	0.9494 (3)	0.7466 (3)	0.1110 (2)	0.0331 (7)
P1	0.75192 (10)	0.24553 (10)	0.24302 (6)	0.0132 (2)
Rh1	0.72947 (3)	0.13381 (3)	0.381902 (17)	0.01389 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0155 (19)	0.015 (2)	0.0185 (19)	−0.0022 (16)	0.0009 (15)	0.0012 (15)
C2	0.019 (2)	0.031 (2)	0.019 (2)	−0.0048 (18)	0.0013 (16)	−0.0045 (17)
C3	0.028 (2)	0.032 (3)	0.034 (2)	−0.010 (2)	0.0047 (19)	−0.004 (2)
C4	0.028 (3)	0.029 (3)	0.056 (3)	−0.001 (2)	−0.007 (2)	−0.018 (2)
C11	0.0118 (17)	0.017 (2)	0.0139 (17)	−0.0053 (15)	0.0017 (14)	−0.0026 (14)
C12	0.0152 (19)	0.016 (2)	0.0204 (19)	−0.0018 (16)	−0.0023 (15)	−0.0032 (15)
C13	0.024 (2)	0.017 (2)	0.021 (2)	−0.0059 (17)	0.0032 (16)	−0.0079 (16)
C14	0.022 (2)	0.027 (2)	0.0160 (18)	−0.0123 (18)	−0.0006 (15)	−0.0065 (16)
C15	0.019 (2)	0.025 (2)	0.0168 (19)	−0.0090 (17)	−0.0019 (15)	0.0012 (16)
C16	0.0164 (19)	0.015 (2)	0.0202 (19)	−0.0058 (16)	−0.0027 (15)	−0.0035 (15)
C21	0.0148 (18)	0.0135 (19)	0.0211 (19)	−0.0032 (15)	−0.0008 (15)	−0.0055 (15)
C22	0.0146 (19)	0.015 (2)	0.0178 (18)	−0.0037 (15)	0.0039 (14)	−0.0038 (15)
C23	0.018 (2)	0.021 (2)	0.022 (2)	−0.0057 (16)	0.0004 (16)	−0.0064 (16)
C24	0.0154 (19)	0.017 (2)	0.030 (2)	−0.0062 (16)	0.0063 (16)	−0.0098 (17)
C25	0.026 (2)	0.024 (2)	0.018 (2)	−0.0099 (18)	0.0074 (16)	−0.0076 (17)
C26	0.022 (2)	0.020 (2)	0.021 (2)	−0.0073 (17)	−0.0044 (16)	−0.0044 (16)
C31	0.0189 (19)	0.0141 (19)	0.0121 (17)	−0.0022 (15)	−0.0062 (14)	−0.0010 (14)
C32	0.019 (2)	0.018 (2)	0.0162 (18)	−0.0081 (16)	−0.0061 (15)	−0.0025 (15)
C33	0.025 (2)	0.015 (2)	0.022 (2)	−0.0097 (17)	−0.0054 (16)	−0.0024 (16)
C34	0.027 (2)	0.012 (2)	0.024 (2)	−0.0001 (16)	−0.0081 (17)	−0.0067 (16)
C35	0.017 (2)	0.017 (2)	0.0195 (19)	0.0021 (16)	−0.0019 (15)	−0.0037 (16)
C36	0.022 (2)	0.018 (2)	0.0151 (18)	−0.0068 (17)	0.0020 (15)	−0.0020 (15)
C41	0.0142 (18)	0.019 (2)	0.0144 (18)	−0.0070 (16)	0.0014 (14)	−0.0077 (15)
C42	0.018 (2)	0.017 (2)	0.0162 (18)	−0.0006 (16)	0.0003 (15)	−0.0040 (15)
C43	0.019 (2)	0.027 (2)	0.0180 (19)	−0.0052 (17)	−0.0008 (15)	−0.0054 (16)
C44	0.022 (2)	0.026 (2)	0.0190 (19)	−0.0122 (18)	−0.0008 (16)	−0.0068 (16)
C45	0.0175 (19)	0.020 (2)	0.0180 (19)	−0.0092 (16)	0.0047 (15)	−0.0090 (16)
C46	0.0123 (18)	0.0146 (19)	0.0169 (18)	−0.0047 (15)	0.0023 (14)	−0.0057 (15)
C47	0.0158 (19)	0.016 (2)	0.0189 (19)	−0.0059 (16)	−0.0003 (15)	−0.0041 (15)
C48	0.0142 (19)	0.019 (2)	0.023 (2)	−0.0009 (16)	0.0011 (15)	−0.0044 (16)
C49	0.019 (2)	0.016 (2)	0.026 (2)	−0.0036 (16)	0.0058 (16)	−0.0044 (16)
C50	0.027 (2)	0.020 (2)	0.0180 (19)	−0.0153 (18)	0.0090 (16)	−0.0086 (16)
N1	0.0145 (16)	0.0126 (16)	0.0143 (15)	−0.0028 (13)	0.0005 (12)	−0.0036 (12)
N7	0.0158 (16)	0.0121 (16)	0.0190 (16)	−0.0019 (13)	−0.0038 (13)	−0.0009 (13)
O1	0.0324 (18)	0.0344 (19)	0.0309 (16)	−0.0209 (15)	−0.0054 (13)	−0.0089 (14)
O2	0.0209 (14)	0.0182 (14)	0.0101 (12)	−0.0076 (12)	0.0009 (10)	−0.0023 (10)
O3	0.0206 (14)	0.0158 (14)	0.0130 (13)	−0.0035 (11)	−0.0021 (10)	−0.0015 (10)
O4	0.0233 (17)	0.040 (2)	0.0330 (17)	−0.0042 (14)	−0.0052 (13)	−0.0079 (14)
P1	0.0131 (5)	0.0114 (5)	0.0141 (5)	−0.0018 (4)	−0.0013 (4)	−0.0035 (4)
Rh1	0.01397 (18)	0.01172 (19)	0.01518 (18)	−0.00255 (13)	−0.00048 (12)	−0.00361 (12)

C1—O1	1.146 (5)	C31—C36	1.389 (5)
C1—Rh1	1.817 (4)	C31—P1	1.832 (4)
C2—O4	1.226 (5)	C32—C33	1.379 (5)
C2—C3	1.497 (6)	C32—H32	0.93
C2—C4	1.507 (6)	C33—C34	1.388 (6)
C3—H3A	0.96	C33—H33	0.93
C3—H3B	0.96	C34—C35	1.371 (6)
C3—H3C	0.96	C34—H34	0.93
C4—H4A	0.96	C35—C36	1.381 (5)
C4—H4B	0.96	C35—H35	0.93
C4—H4C	0.96	C36—H36	0.93
C11—C16	1.385 (5)	C41—C42	1.372 (5)
C11—C12	1.407 (5)	C41—C46	1.414 (5)
C11—P1	1.823 (4)	C41—N1	1.448 (5)
C12—C13	1.373 (5)	C42—C43	1.410 (6)
C12—H12	0.93	C42—H42	0.93
C13—C14	1.393 (5)	C43—C44	1.368 (6)
C13—H13	0.93	C43—H43	0.93
C14—C15	1.377 (6)	C44—C45	1.424 (5)
C14—H14	0.93	C44—H44	0.93
C15—C16	1.398 (5)	C45—C50	1.416 (5)
C15—H15	0.93	C45—C46	1.433 (5)
C16—H16	0.93	C46—C47	1.423 (5)
C21—C26	1.394 (5)	C47—C48	1.367 (5)
C21—C22	1.407 (5)	C47—H47	0.93
C21—P1	1.825 (4)	C48—C49	1.410 (6)
C22—C23	1.401 (5)	C48—H48	0.93
C22—H22	0.93	C49—C50	1.367 (6)
C23—C24	1.367 (5)	C49—H49	0.93
C23—H23	0.93	C50—H50	0.93
C24—C25	1.387 (6)	N1—N7	1.281 (4)
C24—H24	0.93	N1—O2	1.346 (4)
C25—C26	1.400 (6)	N7—O3	1.323 (4)
C25—H25	0.93	O2—Rh1	2.026 (3)
C26—H26	0.93	O3—Rh1	2.082 (2)
C31—C32	1.385 (5)	P1—Rh1	2.2240 (11)
O1—C1—Rh1	177.7 (4)	C32—C33—H33	119.8
O4—C2—C3	122.5 (4)	C34—C33—H33	119.8
O4—C2—C4	121.1 (4)	C35—C34—C33	119.6 (4)
C3—C2—C4	116.3 (4)	C35—C34—H34	120.2
C2—C3—H3A	109.5	C33—C34—H34	120.2
C2—C3—H3B	109.5	C34—C35—C36	120.2 (4)
H3A—C3—H3B	109.5	C34—C35—H35	119.9
C2—C3—H3C	109.5	C36—C35—H35	119.9
H3A—C3—H3C	109.5	C35—C36—C31	120.7 (4)
H3B—C3—H3C	109.5	C35—C36—H36	119.6
C2—C4—H4A	109.5	C31—C36—H36	119.6
C2—C4—H4B	109.5	C42—C41—C46	123.7 (3)
H4A—C4—H4B	109.5	C42—C41—N1	118.5 (3)
C2—C4—H4C	109.5	C46—C41—N1	117.8 (3)
H4A—C4—H4C	109.5	C41—C42—C43	119.3 (4)
H4B—C4—H4C	109.5	C41—C42—H42	120.3
C16—C11—C12	118.5 (3)	C43—C42—H42	120.3
C16—C11—P1	123.3 (3)	C44—C43—C42	119.5 (4)
C12—C11—P1	118.1 (3)	C44—C43—H43	120.2
C13—C12—C11	120.7 (4)	C42—C43—H43	120.2
C13—C12—H12	119.7	C43—C44—C45	121.9 (4)
C11—C12—H12	119.7	C43—C44—H44	119.1
C12—C13—C14	120.5 (4)	C45—C44—H44	119.1
C12—C13—H13	119.7	C50—C45—C44	122.5 (3)
C14—C13—H13	119.7	C50—C45—C46	118.3 (3)
C15—C14—C13	119.3 (3)	C44—C45—C46	119.2 (3)
C15—C14—H14	120.3	C41—C46—C47	124.5 (3)
C13—C14—H14	120.3	C41—C46—C45	116.3 (3)
C14—C15—C16	120.5 (4)	C47—C46—C45	119.2 (3)
C14—C15—H15	119.7	C48—C47—C46	120.3 (4)
C16—C15—H15	119.7	C48—C47—H47	119.8
C11—C16—C15	120.4 (4)	C46—C47—H47	119.8
C11—C16—H16	119.8	C47—C48—C49	120.7 (4)
C15—C16—H16	119.8	C47—C48—H48	119.6
C26—C21—C22	118.7 (3)	C49—C48—H48	119.6
C26—C21—P1	122.8 (3)	C50—C49—C48	120.3 (4)
C22—C21—P1	118.4 (3)	C50—C49—H49	119.8
C23—C22—C21	120.2 (3)	C48—C49—H49	119.8
C23—C22—H22	119.9	C49—C50—C45	121.2 (4)
C21—C22—H22	119.9	C49—C50—H50	119.4
C24—C23—C22	120.4 (4)	C45—C50—H50	119.4
C24—C23—H23	119.8	N7—N1—O2	123.9 (3)
C22—C23—H23	119.8	N7—N1—C41	119.5 (3)
C23—C24—C25	120.2 (4)	O2—N1—C41	116.7 (3)
C23—C24—H24	119.9	N1—N7—O3	114.3 (3)
C25—C24—H24	119.9	N1—O2—Rh1	110.0 (2)
C24—C25—C26	120.3 (4)	N7—O3—Rh1	113.7 (2)
C24—C25—H25	119.8	C11—P1—C21	102.64 (17)
C26—C25—H25	119.8	C11—P1—C31	103.59 (16)
C21—C26—C25	120.2 (4)	C21—P1—C31	106.98 (17)
C21—C26—H26	119.9	C11—P1—Rh1	121.83 (13)
C25—C26—H26	119.9	C21—P1—Rh1	113.03 (12)
C32—C31—C36	118.7 (4)	C31—P1—Rh1	107.63 (12)
C32—C31—P1	124.3 (3)	C1—Rh1—O2	176.15 (13)
C36—C31—P1	117.0 (3)	C1—Rh1—O3	101.74 (14)
C33—C32—C31	120.4 (4)	O2—Rh1—O3	77.74 (10)
C33—C32—H32	119.8	C1—Rh1—P1	90.54 (12)
C31—C32—H32	119.8	O2—Rh1—P1	89.92 (8)
C32—C33—C34	120.3 (4)	O3—Rh1—P1	167.66 (8)

C1—Rh1	1.817 (4)
O2—Rh1	2.026 (3)
O3—Rh1	2.082 (2)
P1—Rh1	2.2240 (11)

C1—Rh1—O2	176.15 (13)
C1—Rh1—O3	101.74 (14)
O2—Rh1—O3	77.74 (10)
C1—Rh1—P1	90.54 (12)
O2—Rh1—P1	89.92 (8)
O3—Rh1—P1	167.66 (8)