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In the title compound, [Rh(C9H7ClNO)(C18H12Cl3P)(CO)], the phosphine ligand is trans to the N atom of the quinolinolate ligand. This indicates that changes in the electronic properties of the quinolinolate backbone have a negligible influence on the phosphine substitution. Important geometrical parameters are the quinolinolate bite angle of 80.15 (9)° and the Rh—P bond distance of 2.2478 (9) Å, the effective cone angle (ΘE) for the phosphine ligand being 165°. Quinoline ligand-to-ligand π-stacking is in a tail-to-tail fashion with an inter­molecular distance of 3.26 Å. The molecule also exhibits intramolecular C—H...Cl and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056152/sj2393sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056152/sj2393Isup2.hkl
Contains datablock I

CCDC reference: 672659

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.036
  • wR factor = 0.068
  • Data-to-parameter ratio = 20.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 500 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.52 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Rh - C10 .. 6.68 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Bonding of bidentate ligands to transition metals is a well known concept. One of the most common bidentate examples are probably the β-diketones, e.g. acetylacetone, with 42 entries in the CSD for Rh(I) complexes alone [Cambridge Structural Database, Version 5.28, May 2007 (Allen, 2002)]. Bidentate ligands with different donor atoms such as 8-hydroxyquinoline and its derivatives also form chelating ring systems with transition metals, via the N, O donor atoms. To date there are six 8-hydroxylquinolinatorhodium(I) complexes deposited in the CSD.

In the title compound [Rh(C9H7ClNO)(CO){P(C6H4Cl)3}], the fused ring system of the bidentate ligand is almost planar, with an r.m.s. deviation from planarity of 0.0423 Å and a dihedral angle of 4.87 (16) Å between the benzene and pyridine rings. The 5'-chloro substituent, the O-donor atom and the metal centre are essentially in the plane of the quinoline system, displaced by 0.124 (3) Å, 0.081 (3) Å and 0.065 (3) Å respectively. The rhodium metal centre is slightly displaced from the coordination plane by 0.014 (1) Å (r.m.s of fitted atoms = 0.0007 Å). The N···O bite distance is 2.659 (9) Å and the N—Rh—O bite angle is 80.15 (9)°. The Rh—P bond distance is 2.2478 (9) Å, while the C8—O1 bond distance is 1.326 (3) Å and the endocyclic angle at C7—C8—C9 = 117.8 (3)°. These are comparable to the average distances for rhodium(I)quinolinato complexes reported previously (Janse van Rensburg et al., 2005a,b, 2006, a,b, Janse van Rensburg & Roodt, 2006).

The metal-carbonyl is slightly bent with a Rh—C10—O2 bond angle of 177.4 (3)°, and a C10—O2 bond distance of 1.154 (4) Å, also comparable with previous reported rhodium(I)quinolinol complexes. Phosphine ligand substitution occurred trans to the N-donor atom which is the stronger σ-donor. Phosphine substituent arrangement is in such a way that one of the phenyl rings is cis to the carbonyl, reflected by the C10—Rh—P—C11 torsion angle of 1.86 (14)°. The steric behavior of the ligand at the metal centre was determined by calculating the effective cone angle as described previously (Tolman, 1977; Otto et al., 2000). A value of 165° was obtained.

Short intramolecular contacts are present between C3···Cl with C3—H···Cl = 104° and C3···Cl = 3.132 (4) Å and beween C22···O1 with C22—H···O1 = 149.3° and C22···O1 = 3.111 (4) Å. The familiar quinoline ligand to ligand stacking fashion for these type of compounds is also present, stabilized with a π-stacking distance of 3.26 Å between the palnes defined by the C1···C9, N atoms of adjacent quinoline ligands; in addition, there are two Rh···H contacts (3.388 Å) and two Cl···O contacts (3.489 Å).

Banerjee and Saha reported the effects on bond lengths and angles of the free 5'-chloro moiety versus that of the free 8-hydroxyquinoline ligand (Banarjee & Saha, 1986). In this article we compare these to the rhodium bonded 5-chloro-8-hydroxyquinoline title compound (Table 1). There is a ca 0.1 Å decrease in the N···O bite distance of the title compound, 2.659 (9) Å, when compared to that of the free ligand. Chelation of 5-chloro-8-hydroxyquinoline to the metal centre shortens the C8—O1 bond distance by ca 0.04 Å, compared to the neutral 8-hydroxyquinolines (Hughes & Truter, 1979).

A decrease is also noted in the C6—C7—C8 ring angle when comparing the title compound with the free 5-chloro-8-hydroxyquinoline and unsubstituted 8-hydroxyquinoline, (117.8 (3)°, 119.6 (5)° and 121.4 (4)°), respectively. Thus the smaller the endocyclic ring angle, the stronger conjugation is observed between the benzene and the oxygen (O1) (Banerjee & Saha, 1986; Domenicano et al., 1975).

Related literature top

For the neutral 5-chloro-8-hydroxyquinoline ligand structure. see: Banerjee & Saha (1986). For an example of a β-diketonatorhodium(I)phosphine complex, see: Brink et al. (2007). For related quinolinatorhodium(I)phosphite complexes, see: Janse van Rensburg et al. (2005a,b, 2006a). For quinolinatorhodium(I)phosphine complexes, see Janse van Rensburg & Roodt (2006); Janse van Rensburg et al. (2006b). For related literature, see: Allen (2002); Domenicano et al. (1975); Hughes & Truter (1979); McCleverty & Wilkinson (1990); Otto et al. (2000); Tolman (1977).

Experimental top

Chemicals and solvents were obtained from Sigma-Aldrich and used as received. [RhCl(CO)2]2 was prepared according to the literature method (McCleverty & Wilkinson, 1990). [Rh(5ClOX)(CO)2] was synthesized by mixing solutions of 5-chloro-8-hydroxyquinoline, (5ClOX), (61.4 mg, 0.344 mmol) in DMF (1 ml) and [RhCl(CO)2]2 (60.9 mg, 0.156 mmol) in DMF (1 ml). Upon addition of ice water (30 ml) the product precipitated and was filtered. Ligand substitution on the complex [Rh(5ClOX)(CO)2] was performed by dissolving (50 mg, 0.148 mmol) in acetone (40 ml) followed by slow addition of P(4-ClC6H4)3 (55 mg, 0.163 mmol) in acetone (10 ml). Upon evaporation, crystals suitable for single-crystal X-ray crystallography were obtained (yield: 72 mg, 76%).

Spectroscopic data: 31P{H} NMR (CDCl3, 121.447 MHz, p.p.m.): 40.47 p.p.m. [1J(Rh—P) = 166 Hz]; IR (KBr) ν(CO): 1965 cm-1.

Refinement top

The H atoms were positioned geometrically and refined using a riding model with fixed C—H distances of 0.93 Å (CH) [Uiso(H) = 1.2Ueq].

The highest density peak is 0.68 located 0.95 Å from C10 and the deepest hole is -0.74 located at 0.56 Å from Rh.

Computing details top

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, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of (I) showing the atom-numbering scheme with displacement ellipsoids at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. Part of the unit-cell contents viewed along the a axis, showing the quinoline ligand to ligand π-stacking.
Carbonyl(5-chloroquinolin-8-olato-κ2N,O)[tris(4-chlorophenyl)phosphine- κP]rhodium(I) top
Crystal data top
[Rh(C9H7ClNO)(C18H12Cl3P)(CO)]F(000) = 1344
Mr = 675.11Dx = 1.67 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5536 reflections
a = 9.558 (5) Åθ = 2.5–28.1°
b = 19.788 (5) ŵ = 1.12 mm1
c = 14.608 (5) ÅT = 100 K
β = 103.670 (5)°Cuboid, yellow
V = 2684.6 (18) Å30.12 × 0.08 × 0.06 mm
Z = 4
Data collection top
Bruker X8 APEXII 4K Kappa CCD
diffractometer
6708 independent reflections
Radiation source: fine-focus sealed tube4272 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.097
ω & ϕ scansθmax = 28.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 1212
Tmin = 0.877, Tmax = 0.946k = 2626
39703 measured reflectionsl = 1919
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0221P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.068(Δ/σ)max < 0.001
S = 0.88Δρmax = 0.68 e Å3
6708 reflectionsΔρmin = 0.74 e Å3
334 parameters
Crystal data top
[Rh(C9H7ClNO)(C18H12Cl3P)(CO)]V = 2684.6 (18) Å3
Mr = 675.11Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.558 (5) ŵ = 1.12 mm1
b = 19.788 (5) ÅT = 100 K
c = 14.608 (5) Å0.12 × 0.08 × 0.06 mm
β = 103.670 (5)°
Data collection top
Bruker X8 APEXII 4K Kappa CCD
diffractometer
6708 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
4272 reflections with I > 2σ(I)
Tmin = 0.877, Tmax = 0.946Rint = 0.097
39703 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.068H-atom parameters constrained
S = 0.88Δρmax = 0.68 e Å3
6708 reflectionsΔρmin = 0.74 e Å3
334 parameters
Special details top

Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 40 s/frame. A total of 1348 frames were collected with a frame width of 0.5° covering up to θ = 28.36° with 99.7% 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1624 (4)0.04276 (15)0.0917 (2)0.0211 (7)
H10.24560.0520.07130.025*
C20.1670 (4)0.00805 (15)0.1592 (2)0.0248 (8)
H20.25160.03190.18270.03*
C30.0468 (4)0.02217 (15)0.1899 (2)0.0240 (8)
H30.04980.05510.23580.029*
C40.0823 (4)0.01282 (14)0.15262 (19)0.0206 (7)
C50.2164 (4)0.00051 (15)0.1737 (2)0.0260 (8)
C60.3369 (4)0.03361 (16)0.1267 (2)0.0291 (8)
H60.42490.0230.13980.035*
C70.3318 (4)0.08330 (16)0.0591 (2)0.0262 (8)
H70.41620.10480.02780.031*
C80.2036 (4)0.10045 (14)0.03872 (19)0.0189 (7)
C90.0780 (4)0.06354 (15)0.08460 (19)0.0183 (7)
C100.1950 (4)0.16063 (16)0.05666 (19)0.0214 (7)
C110.0802 (3)0.27579 (14)0.20064 (19)0.0143 (6)
C120.1370 (3)0.23426 (15)0.2598 (2)0.0188 (7)
H120.09980.1910.27330.023*
C130.2469 (3)0.25576 (16)0.2985 (2)0.0215 (7)
H130.28250.2280.33910.026*
C140.3032 (3)0.31923 (16)0.27585 (19)0.0194 (7)
C150.2514 (3)0.36159 (15)0.21715 (19)0.0205 (7)
H150.29210.4040.20210.025*
C160.1378 (3)0.34030 (16)0.18070 (18)0.0189 (7)
H160.09960.36920.14270.023*
C210.2029 (3)0.22046 (14)0.24806 (19)0.0146 (6)
C220.3095 (3)0.17624 (14)0.2356 (2)0.0189 (7)
H220.30460.15750.17650.023*
C230.4229 (3)0.15985 (16)0.3101 (2)0.0235 (7)
H230.49410.13010.30160.028*
C240.4294 (3)0.18803 (15)0.3974 (2)0.0197 (7)
C250.3261 (3)0.23252 (15)0.4116 (2)0.0202 (7)
H250.33210.25140.47070.024*
C260.2132 (3)0.24863 (15)0.3365 (2)0.0183 (7)
H260.1430.27880.34540.022*
C310.1206 (3)0.31427 (14)0.09282 (19)0.0170 (7)
C320.0440 (4)0.33531 (16)0.0045 (2)0.0246 (7)
H320.03550.31060.02730.029*
C330.0851 (4)0.39297 (17)0.0367 (2)0.0340 (9)
H330.03240.40770.09520.041*
C340.2040 (4)0.42767 (16)0.0099 (2)0.0267 (8)
C350.2825 (4)0.40741 (17)0.0963 (2)0.0359 (9)
H350.36430.43120.12670.043*
C360.2384 (4)0.35094 (17)0.1379 (2)0.0313 (8)
H360.28960.33760.19750.038*
N0.0451 (3)0.07802 (12)0.05580 (16)0.0179 (6)
O10.1899 (2)0.14853 (10)0.02175 (13)0.0211 (5)
O20.3131 (2)0.16127 (12)0.06297 (15)0.0329 (6)
P0.05603 (9)0.24118 (4)0.14644 (5)0.01512 (18)
Cl10.44424 (8)0.34634 (4)0.32268 (5)0.02688 (18)
Cl0.22850 (11)0.05749 (4)0.26151 (6)0.0387 (2)
Cl20.57460 (9)0.16895 (4)0.49090 (6)0.0322 (2)
Cl30.25882 (13)0.49923 (5)0.04213 (7)0.0507 (3)
Rh0.01248 (3)0.156302 (12)0.043330 (15)0.01617 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0222 (19)0.0186 (17)0.0196 (16)0.0004 (15)0.0007 (14)0.0037 (13)
C20.032 (2)0.0150 (16)0.0213 (16)0.0053 (16)0.0052 (15)0.0011 (13)
C30.042 (2)0.0131 (16)0.0145 (15)0.0019 (16)0.0023 (15)0.0019 (12)
C40.038 (2)0.0090 (15)0.0145 (15)0.0037 (15)0.0057 (14)0.0019 (12)
C50.045 (2)0.0142 (16)0.0249 (17)0.0032 (16)0.0201 (16)0.0040 (13)
C60.038 (2)0.0186 (17)0.039 (2)0.0054 (17)0.0253 (18)0.0039 (15)
C70.030 (2)0.0229 (18)0.0283 (18)0.0086 (16)0.0128 (16)0.0053 (14)
C80.031 (2)0.0121 (15)0.0158 (15)0.0055 (14)0.0090 (14)0.0006 (12)
C90.029 (2)0.0122 (15)0.0140 (14)0.0037 (14)0.0066 (14)0.0027 (12)
C100.030 (2)0.0153 (16)0.0162 (15)0.0012 (17)0.0008 (14)0.0030 (13)
C110.0139 (16)0.0131 (15)0.0139 (14)0.0017 (13)0.0006 (12)0.0025 (11)
C120.0174 (18)0.0145 (16)0.0241 (16)0.0012 (14)0.0038 (14)0.0029 (13)
C130.0219 (19)0.0223 (17)0.0203 (16)0.0057 (15)0.0050 (14)0.0018 (13)
C140.0148 (17)0.0262 (17)0.0162 (15)0.0019 (14)0.0017 (13)0.0061 (13)
C150.0260 (19)0.0152 (16)0.0189 (16)0.0042 (14)0.0026 (14)0.0022 (12)
C160.0247 (17)0.0170 (15)0.0144 (14)0.0057 (16)0.0033 (12)0.0019 (13)
C210.0162 (17)0.0114 (15)0.0154 (15)0.0008 (13)0.0019 (12)0.0023 (11)
C220.0228 (18)0.0154 (16)0.0188 (15)0.0000 (14)0.0058 (13)0.0034 (12)
C230.0232 (18)0.0142 (15)0.0317 (17)0.0053 (16)0.0038 (14)0.0033 (14)
C240.0173 (18)0.0180 (16)0.0222 (16)0.0057 (14)0.0015 (14)0.0076 (13)
C250.0227 (19)0.0233 (18)0.0143 (15)0.0000 (15)0.0040 (13)0.0000 (13)
C260.0173 (17)0.0158 (16)0.0228 (16)0.0025 (14)0.0064 (13)0.0002 (13)
C310.0221 (18)0.0128 (15)0.0183 (15)0.0008 (14)0.0091 (13)0.0004 (12)
C320.0297 (19)0.0237 (18)0.0196 (15)0.0088 (16)0.0046 (14)0.0001 (14)
C330.046 (3)0.034 (2)0.0207 (18)0.0048 (19)0.0046 (17)0.0100 (15)
C340.036 (2)0.0156 (17)0.0323 (19)0.0041 (16)0.0157 (17)0.0097 (14)
C350.033 (2)0.028 (2)0.041 (2)0.0162 (18)0.0041 (17)0.0070 (16)
C360.032 (2)0.0269 (19)0.0283 (17)0.0092 (18)0.0065 (15)0.0109 (15)
N0.0257 (16)0.0123 (13)0.0137 (12)0.0017 (12)0.0003 (11)0.0014 (10)
O10.0287 (13)0.0174 (11)0.0198 (10)0.0066 (11)0.0111 (9)0.0057 (9)
O20.0242 (14)0.0392 (15)0.0337 (13)0.0024 (13)0.0037 (11)0.0060 (12)
P0.0190 (4)0.0113 (4)0.0148 (4)0.0008 (3)0.0034 (3)0.0005 (3)
Cl10.0214 (4)0.0336 (5)0.0269 (4)0.0015 (4)0.0080 (3)0.0069 (4)
Cl0.0581 (7)0.0247 (5)0.0409 (5)0.0090 (5)0.0271 (5)0.0160 (4)
Cl20.0282 (5)0.0343 (5)0.0284 (4)0.0036 (4)0.0046 (4)0.0078 (4)
Cl30.0676 (8)0.0303 (5)0.0560 (6)0.0130 (5)0.0181 (6)0.0206 (5)
Rh0.02153 (13)0.01224 (11)0.01413 (11)0.00259 (12)0.00298 (9)0.00139 (10)
Geometric parameters (Å, º) top
C1—N1.319 (4)C15—H150.93
C1—C21.401 (4)C16—H160.93
C1—H10.93C21—C221.387 (4)
C2—C31.357 (5)C21—C261.389 (4)
C2—H20.93C21—P1.833 (3)
C3—C41.408 (4)C22—C231.381 (4)
C3—H30.93C22—H220.93
C4—C51.409 (5)C23—C241.379 (4)
C4—C91.420 (4)C23—H230.93
C5—C61.361 (5)C24—C251.375 (4)
C5—Cl1.745 (3)C24—Cl21.744 (3)
C6—C71.403 (4)C25—C261.382 (4)
C6—H60.93C25—H250.93
C7—C81.370 (5)C26—H260.93
C7—H70.93C31—C361.371 (4)
C8—O11.326 (3)C31—C321.388 (4)
C8—C91.430 (4)C31—P1.820 (3)
C9—N1.370 (4)C32—C331.390 (4)
C10—O21.154 (4)C32—H320.93
C10—Rh1.803 (4)C33—C341.364 (5)
C11—C121.392 (4)C33—H330.93
C11—C161.393 (4)C34—C351.368 (4)
C11—P1.811 (3)C34—Cl31.746 (3)
C12—C131.372 (4)C35—C361.384 (4)
C12—H120.93C35—H350.93
C13—C141.376 (4)C36—H360.93
C13—H130.93N—Rh2.093 (2)
C14—C151.373 (4)O1—Rh2.038 (2)
C14—Cl11.734 (3)P—Rh2.2478 (9)
C15—C161.383 (4)
N—C1—C2122.8 (3)C23—C22—C21120.5 (3)
N—C1—H1118.6C23—C22—H22119.7
C2—C1—H1118.6C21—C22—H22119.7
C3—C2—C1119.5 (3)C24—C23—C22119.3 (3)
C3—C2—H2120.2C24—C23—H23120.4
C1—C2—H2120.2C22—C23—H23120.4
C2—C3—C4120.2 (3)C25—C24—C23121.4 (3)
C2—C3—H3119.9C25—C24—Cl2119.2 (2)
C4—C3—H3119.9C23—C24—Cl2119.4 (2)
C3—C4—C5126.2 (3)C24—C25—C26118.8 (3)
C3—C4—C9116.8 (3)C24—C25—H25120.6
C5—C4—C9117.0 (3)C26—C25—H25120.6
C6—C5—C4120.8 (3)C25—C26—C21121.1 (3)
C6—C5—Cl119.5 (3)C25—C26—H26119.5
C4—C5—Cl119.8 (3)C21—C26—H26119.5
C5—C6—C7121.8 (3)C36—C31—C32118.7 (3)
C5—C6—H6119.1C36—C31—P122.5 (2)
C7—C6—H6119.1C32—C31—P118.7 (2)
C8—C7—C6120.5 (3)C31—C32—C33120.6 (3)
C8—C7—H7119.7C31—C32—H32119.7
C6—C7—H7119.7C33—C32—H32119.7
O1—C8—C7123.8 (3)C34—C33—C32119.0 (3)
O1—C8—C9118.4 (3)C34—C33—H33120.5
C7—C8—C9117.8 (3)C32—C33—H33120.5
N—C9—C4122.1 (3)C33—C34—C35121.6 (3)
N—C9—C8115.9 (3)C33—C34—Cl3119.4 (3)
C4—C9—C8121.9 (3)C35—C34—Cl3118.9 (3)
O2—C10—Rh177.4 (3)C34—C35—C36118.9 (3)
C12—C11—C16118.5 (3)C34—C35—H35120.5
C12—C11—P118.3 (2)C36—C35—H35120.5
C16—C11—P123.0 (2)C31—C36—C35121.2 (3)
C13—C12—C11121.4 (3)C31—C36—H36119.4
C13—C12—H12119.3C35—C36—H36119.4
C11—C12—H12119.3C1—N—C9118.6 (3)
C12—C13—C14118.6 (3)C1—N—Rh129.8 (2)
C12—C13—H13120.7C9—N—Rh111.65 (19)
C14—C13—H13120.7C8—O1—Rh113.82 (19)
C15—C14—C13121.9 (3)C11—P—C31103.86 (14)
C15—C14—Cl1119.1 (2)C11—P—C21102.88 (13)
C13—C14—Cl1119.0 (2)C31—P—C21104.69 (14)
C14—C15—C16119.1 (3)C11—P—Rh116.73 (10)
C14—C15—H15120.4C31—P—Rh112.33 (10)
C16—C15—H15120.4C21—P—Rh114.94 (10)
C15—C16—C11120.4 (3)C10—Rh—O1176.92 (11)
C15—C16—H16119.8C10—Rh—N96.90 (12)
C11—C16—H16119.8O1—Rh—N80.15 (9)
C22—C21—C26118.9 (3)C10—Rh—P91.62 (10)
C22—C21—P118.7 (2)O1—Rh—P91.33 (6)
C26—C21—P122.4 (2)N—Rh—P171.45 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cl0.932.773.132 (4)104
C22—H22···O10.932.273.111 (4)149

Experimental details

Crystal data
Chemical formula[Rh(C9H7ClNO)(C18H12Cl3P)(CO)]
Mr675.11
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)9.558 (5), 19.788 (5), 14.608 (5)
β (°) 103.670 (5)
V3)2684.6 (18)
Z4
Radiation typeMo Kα
µ (mm1)1.12
Crystal size (mm)0.12 × 0.08 × 0.06
Data collection
DiffractometerBruker X8 APEXII 4K Kappa CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.877, 0.946
No. of measured, independent and
observed [I > 2σ(I)] reflections
39703, 6708, 4272
Rint0.097
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.068, 0.88
No. of reflections6708
No. of parameters334
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.68, 0.74

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg & Putz, 2005), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top
C10—O21.154 (4)O1—Rh2.038 (2)
C10—Rh1.803 (4)P—Rh2.2478 (9)
N—Rh2.093 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···Cl0.932.773.132 (4)104
C22—H22···O10.932.273.111 (4)149.3
Comparative geometrical data (Å, °) for selected quinoline ligands. top
SystemN···OC—O(hydroxyl)Endocyclic ring angle C7—C8—C9
Rh(OXCl)COP(4-ClPh)3(i)2.659 (9)1.326 (3)117.8 (3)
OXCl(ii)2.747 (7)1.346 (7)119.6 (5)
OX(ii)2.742 (4)1.367 (5)121.4 (4)
(i) This work; (OXCl) = 5-chloro-8-hydroxyquinoline and (4-ClC6H4) = p-chlorophenyl; (ii) Banerjee & Saha (1986); (OX) = 8-hydroxyquinoline.
 

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