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Acta Cryst. (2007). E63, m2968-m2969    [ doi:10.1107/S1600536807053755 ]

Chloridobis[2-(4-fluoroanilino)troponato-[kappa]2N,O](triphenylphosphine-[kappa]P)rhodium(III)

G. Steyl

Abstract top

In the title complex, [Rh(C13H9NOF)2Cl(C18H15P)], the two 2-(4-fluorophenylamino)troponate groups chelate the RhIII atom and the four coordinating atoms are disposed around it as a square in a trans manner. The Cl and P atoms occupy axial positions of the octahedral coordination geometry. The crystal structure shows weak intra- and intermolecular interactions.

Comment top

Rhodium(III) complexes play a vital role in catalytic processes applied in industry today (Crous et al., 2005; Otto & Roodt, 2004), with rhodium systems being investigated for a wide variety of catalytic activities (Roodt et al., 2003; Otto & Roodt, 2002). The title complex, (I), is a possible by-product in these systems where diketonato or acetato ligands might be in use. A similar system have been reported for O,O-diketonato Rh(III) complexes (Das et al., 2002), however the coordination mode differs with one of the diketonato oxygen atoms coordinated via an apical position. The title complex is the first example of a N,O-bidentate Rh(III) complex with a triphenylphosphane and halogen moiety, see Fig. 1.

The distortion of the octahedral geometry about the Rh(III) metal centre can be observed from the slight deviation from linearity of the O—Rh—O and N—Rh—N bond angles of the complex, see Table 1. A significant distortion of the cycloheptatriene moeities is observed as these units are twisted away from the apical triphenylphosphane ligand. The distortion of the seven membered rings are also evidant in the torsion angles of the bidentate ligand, Table 1, which differ by 7 ° for the respective units. The free ligand had a similar but smaller torsional change for the O—C—C—N unit (Steyl, 2007).

The effect of weak intra- and intermolecular interactions play a significant role in determining the packing mode of the title complex. Weak intra- and intermolecular hydrogen bonds are formed in the system with the halogen atoms contributing to the solid state ordering, see Table 2. Intercalation is observed between symmetry associated cycloheptatriene rings; C11···C17 and C11···C17 [−x, 1 − y, −z] and C21···C27 and C21···C27 [−x, 1 − y, 1 − z], in the order of 3.282 (2) and 3.534 (6) Å respectively.

Related literature top

For general background, see: Crous et al. (2005); Otto & Roodt (2004); Roodt et al. (2003); Otto & Roodt (2002). For related diketonato complexes, see: Janse van Rensburg & Roodt (2006); Janse van Rensburg et al. (2006); Das et al. (2002). For the free substituted tropolone ligand, see: Steyl (2007).

Experimental top

The title complex was obtained during the attempted synthesis of the [Rh((N-4-FPh)Trop)CO(PPh3)] derivative, due to the excess of ligands oxidation of the Rh(I) centre occurred. On evaporation of the acetone; crystals suitable for X-Ray crystallography was obtained.

Refinement top

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å and with Uiso(H) = 1.2 times Ueq(C aromatic).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg Putz, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. : Representation of the title compound (I), showing the numbering scheme and displacement ellipsoids (50% probability).
Chloridobis[2-(4-fluoroanilino)troponato- κ2N,O](triphenylphosphine-κP)rhodium(III) top
Crystal data top
[Rh(C13H9NOF)2Cl(C18H15P)]Z = 2
Mr = 829.05F000 = 844
Triclinic, P1Dx = 1.510 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 9.4681 (4) ÅCell parameters from 9643 reflections
b = 10.5333 (5) Åθ = 2.4–28.3º
c = 19.5749 (9) ŵ = 0.64 mm−1
α = 100.552 (2)ºT = 100 (2) K
β = 91.904 (2)ºPlate, red
γ = 107.430 (2)º0.35 × 0.35 × 0.06 mm
V = 1822.98 (14) Å3
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		7924 independent reflections
Radiation source: fine-focus sealed tube7289 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.039
Detector resolution: 512 pixels mm-1θmax = 27.0º
T = 100(2) Kθmin = 2.1º
phi and ω scansh = −11→12
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		k = −13→13
Tmin = 0.808, Tmax = 0.963l = −24→24
50714 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.064  w = 1/[σ2(Fo2) + (0.0253P)2 + 1.3992P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
7924 reflectionsΔρmax = 0.62 e Å−3
478 parametersΔρmin = −0.63 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Rh(C13H9NOF)2Cl(C18H15P)]γ = 107.430 (2)º
Mr = 829.05V = 1822.98 (14) Å3
Triclinic, P1Z = 2
a = 9.4681 (4) ÅMo Kα
b = 10.5333 (5) ŵ = 0.64 mm−1
c = 19.5749 (9) ÅT = 100 (2) K
α = 100.552 (2)º0.35 × 0.35 × 0.06 mm
β = 91.904 (2)º
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer		7924 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		7289 reflections with I > 2σ(I)
Tmin = 0.808, Tmax = 0.963Rint = 0.039
50714 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.025478 parameters
wR(F2) = 0.064H-atom parameters constrained
S = 1.05Δρmax = 0.62 e Å−3
7924 reflectionsΔρmin = −0.63 e Å−3
Special details top

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Rh0.077509 (14)0.273280 (12)0.269392 (6)0.01352 (5)
Cl−0.10642 (5)0.39378 (4)0.28114 (2)0.01912 (9)
P0.23870 (5)0.15092 (4)0.25259 (2)0.01517 (9)
F240.63836 (13)0.86999 (12)0.37281 (7)0.0363 (3)
O2−0.02742 (14)0.16654 (12)0.33902 (6)0.0188 (2)
O10.18050 (13)0.39257 (11)0.20541 (6)0.0155 (2)
F14−0.48903 (18)−0.31325 (15)0.15354 (9)0.0599 (4)
N1−0.03774 (16)0.17037 (14)0.17478 (7)0.0163 (3)
N20.18529 (16)0.39043 (14)0.36101 (7)0.0155 (3)
C410.36683 (19)0.16472 (17)0.32757 (9)0.0172 (3)
C210.00897 (19)0.22668 (18)0.40479 (9)0.0178 (3)
C2260.2743 (2)0.61971 (18)0.33940 (9)0.0194 (4)
H2260.17700.60910.32020.023*
C240.1255 (2)0.4292 (2)0.54940 (9)0.0227 (4)
H240.16660.50600.58610.027*
C116−0.2632 (2)0.0362 (2)0.21465 (10)0.0245 (4)
H116−0.25820.11180.25070.029*
C12−0.00746 (19)0.23929 (17)0.12344 (9)0.0166 (3)
C250.0302 (2)0.3155 (2)0.56990 (9)0.0258 (4)
H250.02070.32230.61850.031*
C460.3023 (2)0.12251 (18)0.38602 (9)0.0201 (4)
H460.19710.09200.38570.024*
C27−0.0616 (2)0.1570 (2)0.45422 (10)0.0234 (4)
H27−0.12800.06880.43560.028*
C220.12562 (19)0.35789 (17)0.41819 (9)0.0163 (3)
C560.2348 (2)−0.11511 (19)0.20036 (10)0.0261 (4)
H560.3302−0.07480.18630.031*
C230.1691 (2)0.44731 (18)0.48484 (9)0.0190 (3)
H230.23940.53310.48430.023*
C420.5211 (2)0.20584 (18)0.32832 (9)0.0203 (4)
H420.56660.23330.28860.024*
C2240.5275 (2)0.75131 (19)0.36894 (10)0.0243 (4)
C520.0157 (2)−0.09324 (19)0.25376 (10)0.0249 (4)
H52−0.0397−0.03840.27600.030*
C510.1532 (2)−0.03287 (17)0.23153 (9)0.0202 (4)
C2210.30347 (19)0.51321 (16)0.36373 (8)0.0157 (3)
C310.3499 (2)0.19638 (18)0.18167 (9)0.0194 (4)
C13−0.1042 (2)0.20736 (18)0.06111 (9)0.0221 (4)
H13−0.19850.14250.06160.027*
C110.12681 (19)0.35670 (17)0.14058 (9)0.0167 (3)
C450.3905 (2)0.12466 (19)0.44454 (10)0.0239 (4)
H450.34560.09700.48430.029*
C2230.5605 (2)0.64715 (19)0.39194 (10)0.0260 (4)
H2230.65920.65710.40900.031*
C320.4651 (2)0.31947 (19)0.19284 (10)0.0245 (4)
H320.48510.37840.23740.029*
C550.1765 (3)−0.2557 (2)0.18998 (10)0.0334 (5)
H550.2318−0.31110.16830.040*
C150.0404 (3)0.3479 (2)−0.01873 (10)0.0322 (5)
H150.03580.3604−0.06550.039*
C360.3158 (2)0.1156 (2)0.11458 (10)0.0261 (4)
H360.23400.03430.10560.031*
C26−0.0507 (2)0.1957 (2)0.52714 (10)0.0271 (4)
H26−0.10800.12870.55030.032*
C160.1687 (2)0.4232 (2)0.02335 (10)0.0293 (4)
H160.24310.47980.00120.035*
C2250.3870 (2)0.74156 (19)0.34297 (10)0.0234 (4)
H2250.36750.81600.32790.028*
C170.2049 (2)0.42846 (18)0.09351 (9)0.0211 (4)
H170.29870.49160.11240.025*
C430.6089 (2)0.20682 (19)0.38693 (10)0.0246 (4)
H430.71410.23490.38710.029*
C14−0.0825 (2)0.2557 (2)0.00036 (10)0.0271 (4)
H14−0.16510.2202−0.03410.033*
C2220.4466 (2)0.52674 (18)0.38975 (9)0.0210 (4)
H2220.46660.45370.40600.025*
C540.0390 (3)−0.3149 (2)0.21096 (10)0.0347 (5)
H54−0.0008−0.41110.20320.042*
C340.5184 (3)0.2719 (3)0.07349 (11)0.0379 (5)
H340.57790.29610.03690.045*
C440.5440 (2)0.16710 (19)0.44505 (10)0.0251 (4)
H440.60440.16890.48520.030*
C114−0.3806 (2)−0.1929 (2)0.15728 (12)0.0373 (5)
C113−0.2799 (2)−0.1844 (2)0.10845 (11)0.0326 (5)
H113−0.2876−0.26010.07200.039*
C112−0.1662 (2)−0.06303 (18)0.11317 (10)0.0236 (4)
H112−0.0938−0.05560.08040.028*
C111−0.1585 (2)0.04800 (17)0.16608 (9)0.0193 (4)
C350.4009 (3)0.1537 (2)0.06111 (11)0.0346 (5)
H350.37790.09780.01570.041*
C115−0.3749 (2)−0.0861 (2)0.21045 (11)0.0334 (5)
H115−0.4462−0.09570.24380.040*
C330.5504 (2)0.3561 (2)0.13909 (11)0.0332 (5)
H330.63050.43860.14720.040*
C53−0.0411 (3)−0.2349 (2)0.24327 (10)0.0319 (5)
H53−0.1351−0.27610.25840.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rh0.01308 (7)0.01306 (7)0.01213 (7)0.00142 (5)−0.00088 (5)0.00165 (5)
Cl0.0173 (2)0.0206 (2)0.0185 (2)0.00600 (16)0.00075 (15)0.00159 (15)
P0.0166 (2)0.0136 (2)0.0138 (2)0.00334 (17)−0.00083 (16)0.00194 (16)
F240.0266 (6)0.0267 (6)0.0439 (7)−0.0104 (5)−0.0072 (5)0.0113 (5)
O20.0186 (6)0.0192 (6)0.0148 (6)0.0003 (5)−0.0003 (5)0.0035 (5)
O10.0177 (6)0.0139 (5)0.0137 (6)0.0032 (5)−0.0001 (4)0.0024 (4)
F140.0449 (9)0.0368 (8)0.0716 (11)−0.0232 (7)0.0016 (8)0.0066 (7)
N10.0155 (7)0.0150 (7)0.0155 (7)0.0021 (6)−0.0008 (5)0.0006 (5)
N20.0146 (7)0.0149 (7)0.0149 (7)0.0022 (6)−0.0023 (5)0.0020 (5)
C410.0185 (8)0.0137 (8)0.0184 (8)0.0056 (7)−0.0025 (7)0.0005 (6)
C210.0145 (8)0.0213 (9)0.0178 (8)0.0058 (7)−0.0005 (6)0.0046 (7)
C2260.0170 (8)0.0211 (9)0.0180 (8)0.0034 (7)−0.0024 (7)0.0040 (7)
C240.0233 (9)0.0288 (10)0.0169 (8)0.0124 (8)−0.0010 (7)0.0005 (7)
C1160.0175 (9)0.0286 (10)0.0222 (9)0.0010 (8)−0.0018 (7)0.0032 (7)
C120.0182 (8)0.0161 (8)0.0154 (8)0.0072 (7)0.0016 (6)−0.0001 (6)
C250.0234 (10)0.0415 (11)0.0145 (8)0.0116 (9)0.0030 (7)0.0078 (8)
C460.0189 (9)0.0197 (9)0.0208 (9)0.0056 (7)0.0000 (7)0.0030 (7)
C270.0187 (9)0.0264 (9)0.0222 (9)0.0015 (7)0.0003 (7)0.0074 (7)
C220.0144 (8)0.0190 (8)0.0167 (8)0.0069 (7)−0.0003 (6)0.0041 (6)
C560.0360 (11)0.0221 (9)0.0203 (9)0.0113 (8)−0.0059 (8)0.0021 (7)
C230.0190 (9)0.0189 (8)0.0183 (8)0.0062 (7)−0.0010 (7)0.0022 (7)
C420.0209 (9)0.0186 (8)0.0207 (9)0.0058 (7)0.0012 (7)0.0027 (7)
C2240.0226 (9)0.0197 (9)0.0229 (9)−0.0042 (7)−0.0017 (7)0.0039 (7)
C520.0294 (10)0.0190 (9)0.0222 (9)0.0023 (8)−0.0062 (8)0.0046 (7)
C510.0269 (10)0.0135 (8)0.0175 (8)0.0043 (7)−0.0074 (7)0.0016 (6)
C2210.0165 (8)0.0146 (8)0.0124 (8)0.0019 (6)0.0000 (6)−0.0010 (6)
C310.0197 (9)0.0235 (9)0.0177 (8)0.0093 (7)0.0036 (7)0.0068 (7)
C130.0230 (9)0.0199 (9)0.0206 (9)0.0049 (7)−0.0036 (7)0.0010 (7)
C110.0188 (8)0.0145 (8)0.0174 (8)0.0074 (7)0.0000 (6)0.0013 (6)
C450.0258 (10)0.0257 (9)0.0200 (9)0.0071 (8)0.0005 (7)0.0061 (7)
C2230.0161 (9)0.0258 (10)0.0316 (10)0.0029 (7)−0.0056 (7)0.0017 (8)
C320.0235 (10)0.0259 (10)0.0253 (9)0.0078 (8)0.0030 (7)0.0080 (8)
C550.0573 (15)0.0217 (10)0.0224 (10)0.0181 (10)−0.0103 (9)0.0000 (8)
C150.0453 (13)0.0347 (11)0.0169 (9)0.0114 (10)−0.0014 (8)0.0080 (8)
C360.0309 (11)0.0285 (10)0.0211 (9)0.0126 (8)0.0009 (8)0.0052 (8)
C260.0220 (10)0.0367 (11)0.0221 (9)0.0037 (8)0.0044 (7)0.0139 (8)
C160.0388 (12)0.0278 (10)0.0208 (9)0.0068 (9)0.0065 (8)0.0089 (8)
C2250.0254 (10)0.0195 (9)0.0239 (9)0.0030 (7)−0.0014 (7)0.0081 (7)
C170.0237 (9)0.0174 (8)0.0206 (9)0.0047 (7)0.0024 (7)0.0030 (7)
C430.0175 (9)0.0245 (9)0.0295 (10)0.0053 (7)−0.0023 (7)0.0027 (8)
C140.0347 (11)0.0263 (10)0.0192 (9)0.0106 (9)−0.0066 (8)0.0013 (7)
C2220.0191 (9)0.0177 (8)0.0246 (9)0.0055 (7)−0.0030 (7)0.0017 (7)
C540.0603 (15)0.0148 (9)0.0238 (10)0.0060 (9)−0.0147 (10)0.0038 (7)
C340.0384 (13)0.0561 (14)0.0294 (11)0.0215 (11)0.0171 (9)0.0204 (10)
C440.0251 (10)0.0265 (10)0.0231 (9)0.0085 (8)−0.0058 (7)0.0041 (7)
C1140.0273 (11)0.0273 (11)0.0439 (13)−0.0104 (9)−0.0058 (9)0.0073 (9)
C1130.0337 (12)0.0208 (10)0.0336 (11)−0.0009 (8)−0.0073 (9)−0.0011 (8)
C1120.0239 (10)0.0199 (9)0.0225 (9)0.0024 (7)−0.0027 (7)0.0008 (7)
C1110.0177 (9)0.0182 (8)0.0184 (8)0.0010 (7)−0.0035 (7)0.0031 (7)
C350.0460 (13)0.0426 (12)0.0201 (10)0.0208 (11)0.0070 (9)0.0065 (9)
C1150.0196 (10)0.0410 (12)0.0318 (11)−0.0038 (9)0.0011 (8)0.0102 (9)
C330.0259 (11)0.0371 (12)0.0389 (12)0.0068 (9)0.0074 (9)0.0180 (9)
C530.0406 (12)0.0219 (10)0.0263 (10)−0.0013 (9)−0.0109 (9)0.0090 (8)
Geometric parameters (Å, °) top
Rh—O12.0054 (12)C52—C511.390 (3)
Rh—O22.0225 (12)C52—C531.399 (3)
Rh—N22.0233 (13)C52—H520.9500
Rh—N12.0536 (14)C221—C2221.389 (2)
Rh—P2.2704 (4)C31—C361.397 (3)
Rh—Cl2.4373 (4)C31—C321.397 (3)
P—C311.8175 (18)C13—C141.375 (3)
P—C511.8220 (18)C13—H130.9500
P—C411.8290 (17)C11—C171.390 (3)
F24—C2241.358 (2)C45—C441.385 (3)
O2—C211.311 (2)C45—H450.9500
O1—C111.295 (2)C223—C2221.390 (3)
F14—C1141.359 (2)C223—H2230.9500
N1—C121.334 (2)C32—C331.388 (3)
N1—C1111.422 (2)C32—H320.9500
N2—C221.325 (2)C55—C541.377 (3)
N2—C2211.425 (2)C55—H550.9500
C41—C421.392 (2)C15—C161.378 (3)
C41—C461.396 (3)C15—C141.387 (3)
C21—C271.389 (3)C15—H150.9500
C21—C221.460 (2)C36—C351.386 (3)
C226—C2251.390 (3)C36—H360.9500
C226—C2211.391 (2)C26—H260.9500
C226—H2260.9500C16—C171.392 (3)
C24—C231.371 (3)C16—H160.9500
C24—C251.401 (3)C225—H2250.9500
C24—H240.9500C17—H170.9500
C116—C1151.387 (3)C43—C441.383 (3)
C116—C1111.391 (3)C43—H430.9500
C116—H1160.9500C14—H140.9500
C12—C131.425 (2)C222—H2220.9500
C12—C111.461 (2)C54—C531.381 (3)
C25—C261.368 (3)C54—H540.9500
C25—H250.9500C34—C351.375 (3)
C46—C451.387 (2)C34—C331.387 (3)
C46—H460.9500C34—H340.9500
C27—C261.402 (3)C44—H440.9500
C27—H270.9500C114—C1131.368 (3)
C22—C231.429 (2)C114—C1151.373 (3)
C56—C551.389 (3)C113—C1121.389 (3)
C56—C511.399 (3)C113—H1130.9500
C56—H560.9500C112—C1111.395 (3)
C23—H230.9500C112—H1120.9500
C42—C431.391 (3)C35—H350.9500
C42—H420.9500C115—H1150.9500
C224—C2231.372 (3)C33—H330.9500
C224—C2251.376 (3)C53—H530.9500
O1—Rh—O2175.41 (5)C36—C31—P121.33 (15)
O1—Rh—N298.36 (5)C32—C31—P119.58 (14)
O2—Rh—N278.32 (5)C14—C13—C12130.19 (19)
O1—Rh—N178.62 (5)C14—C13—H13114.9
O2—Rh—N1104.41 (5)C12—C13—H13114.9
N2—Rh—N1174.43 (5)O1—C11—C17117.59 (16)
O1—Rh—P90.79 (3)O1—C11—C12116.25 (15)
O2—Rh—P92.63 (4)C17—C11—C12126.09 (15)
N2—Rh—P94.69 (4)C44—C45—C46120.07 (18)
N1—Rh—P90.06 (4)C44—C45—H45120.0
O1—Rh—Cl89.39 (3)C46—C45—H45120.0
O2—Rh—Cl87.39 (4)C224—C223—C222118.55 (17)
N2—Rh—Cl89.02 (4)C224—C223—H223120.7
N1—Rh—Cl86.27 (4)C222—C223—H223120.7
P—Rh—Cl176.222 (15)C33—C32—C31120.28 (18)
C31—P—C51106.84 (8)C33—C32—H32119.9
C31—P—C41107.47 (8)C31—C32—H32119.9
C51—P—C4199.36 (8)C54—C55—C56120.3 (2)
C31—P—Rh110.08 (6)C54—C55—H55119.8
C51—P—Rh115.27 (6)C56—C55—H55119.8
C41—P—Rh116.88 (6)C16—C15—C14126.52 (19)
C21—O2—Rh115.43 (11)C16—C15—H15116.7
C11—O1—Rh116.17 (11)C14—C15—H15116.7
C12—N1—C111121.24 (14)C35—C36—C31120.2 (2)
C12—N1—Rh114.11 (11)C35—C36—H36119.9
C111—N1—Rh123.71 (11)C31—C36—H36119.9
C22—N2—C221121.41 (14)C25—C26—C27129.62 (18)
C22—N2—Rh116.04 (11)C25—C26—H26115.2
C221—N2—Rh121.79 (11)C27—C26—H26115.2
C42—C41—C46118.87 (16)C15—C16—C17129.42 (19)
C42—C41—P124.62 (14)C15—C16—H16115.3
C46—C41—P116.38 (13)C17—C16—H16115.3
O2—C21—C27117.17 (16)C224—C225—C226118.08 (17)
O2—C21—C22115.86 (15)C224—C225—H225121.0
C27—C21—C22126.89 (16)C226—C225—H225121.0
C225—C226—C221120.30 (16)C11—C17—C16130.78 (18)
C225—C226—H226119.9C11—C17—H17114.6
C221—C226—H226119.9C16—C17—H17114.6
C23—C24—C25130.34 (18)C44—C43—C42120.41 (18)
C23—C24—H24114.8C44—C43—H43119.8
C25—C24—H24114.8C42—C43—H43119.8
C115—C116—C111119.92 (18)C13—C14—C15130.39 (19)
C115—C116—H116120.0C13—C14—H14114.8
C111—C116—H116120.0C15—C14—H14114.8
N1—C12—C13122.74 (16)C221—C222—C223119.97 (17)
N1—C12—C11113.09 (14)C221—C222—H222120.0
C13—C12—C11123.96 (16)C223—C222—H222120.0
C26—C25—C24126.70 (17)C55—C54—C53120.14 (19)
C26—C25—H25116.6C55—C54—H54119.9
C24—C25—H25116.6C53—C54—H54119.9
C45—C46—C41120.61 (17)C35—C34—C33120.3 (2)
C45—C46—H46119.7C35—C34—H34119.8
C41—C46—H46119.7C33—C34—H34119.8
C21—C27—C26130.54 (18)C43—C44—C45119.78 (17)
C21—C27—H27114.7C43—C44—H44120.1
C26—C27—H27114.7C45—C44—H44120.1
N2—C22—C23122.05 (16)F14—C114—C113118.4 (2)
N2—C22—C21113.11 (15)F14—C114—C115118.8 (2)
C23—C22—C21124.78 (16)C113—C114—C115122.80 (19)
C55—C56—C51120.1 (2)C114—C113—C112118.70 (19)
C55—C56—H56119.9C114—C113—H113120.7
C51—C56—H56119.9C112—C113—H113120.7
C24—C23—C22130.33 (18)C113—C112—C111119.88 (19)
C24—C23—H23114.8C113—C112—H112120.1
C22—C23—H23114.8C111—C112—H112120.1
C43—C42—C41120.25 (17)C116—C111—C112119.95 (17)
C43—C42—H42119.9C116—C111—N1118.97 (16)
C41—C42—H42119.9C112—C111—N1120.87 (17)
F24—C224—C223118.36 (17)C34—C35—C36120.3 (2)
F24—C224—C225118.60 (17)C34—C35—H35119.9
C223—C224—C225123.04 (17)C36—C35—H35119.9
C51—C52—C53119.88 (19)C114—C115—C116118.7 (2)
C51—C52—H52120.1C114—C115—H115120.6
C53—C52—H52120.1C116—C115—H115120.6
C52—C51—C56119.27 (17)C34—C33—C32119.8 (2)
C52—C51—P120.79 (14)C34—C33—H33120.1
C56—C51—P119.46 (15)C32—C33—H33120.1
C222—C221—C226120.02 (16)C54—C53—C52120.2 (2)
C222—C221—N2120.75 (15)C54—C53—H53119.9
C226—C221—N2119.22 (15)C52—C53—H53119.9
C36—C31—C32118.92 (17)
O1—Rh—P—C31−10.46 (7)C41—P—C51—C5298.78 (15)
O2—Rh—P—C31172.59 (7)Rh—P—C51—C52−26.99 (16)
N2—Rh—P—C31−108.92 (8)C31—P—C51—C5638.42 (16)
N1—Rh—P—C3168.16 (8)C41—P—C51—C56−73.15 (15)
O1—Rh—P—C51−131.37 (7)Rh—P—C51—C56161.08 (12)
O2—Rh—P—C5151.68 (7)C225—C226—C221—C222−2.0 (3)
N2—Rh—P—C51130.17 (7)C225—C226—C221—N2178.53 (16)
N1—Rh—P—C51−52.75 (7)C22—N2—C221—C22274.0 (2)
O1—Rh—P—C41112.47 (7)Rh—N2—C221—C222−116.35 (15)
O2—Rh—P—C41−64.48 (7)C22—N2—C221—C226−106.50 (18)
N2—Rh—P—C4114.01 (8)Rh—N2—C221—C22663.10 (19)
N1—Rh—P—C41−168.91 (8)C51—P—C31—C3625.98 (17)
N2—Rh—O2—C217.17 (11)C41—P—C31—C36131.85 (15)
N1—Rh—O2—C21−167.84 (11)Rh—P—C31—C36−99.86 (14)
P—Rh—O2—C21101.42 (11)C51—P—C31—C32−158.86 (14)
Cl—Rh—O2—C21−82.36 (11)C41—P—C31—C32−53.00 (16)
N2—Rh—O1—C11−172.10 (11)Rh—P—C31—C3275.29 (15)
N1—Rh—O1—C113.14 (11)N1—C12—C13—C14−171.02 (18)
P—Rh—O1—C1193.05 (11)C11—C12—C13—C1414.7 (3)
Cl—Rh—O1—C11−83.18 (11)Rh—O1—C11—C17−173.25 (12)
O1—Rh—N1—C12−10.19 (11)Rh—O1—C11—C123.86 (18)
O2—Rh—N1—C12166.28 (11)N1—C12—C11—O1−12.5 (2)
P—Rh—N1—C12−100.98 (12)C13—C12—C11—O1162.26 (16)
Cl—Rh—N1—C1279.95 (12)N1—C12—C11—C17164.28 (16)
O1—Rh—N1—C111−179.21 (14)C13—C12—C11—C17−20.9 (3)
O2—Rh—N1—C111−2.74 (14)C41—C46—C45—C44−0.9 (3)
P—Rh—N1—C11190.00 (13)F24—C224—C223—C222178.37 (17)
Cl—Rh—N1—C111−89.08 (13)C225—C224—C223—C222−0.8 (3)
O1—Rh—N2—C22166.48 (12)C36—C31—C32—C33−4.3 (3)
O2—Rh—N2—C22−10.30 (12)P—C31—C32—C33−179.58 (15)
P—Rh—N2—C22−102.03 (12)C51—C56—C55—C54−0.7 (3)
Cl—Rh—N2—C2277.23 (12)C32—C31—C36—C353.7 (3)
O1—Rh—N2—C221−3.65 (13)P—C31—C36—C35178.93 (15)
O2—Rh—N2—C221179.57 (13)C24—C25—C26—C27−1.3 (4)
P—Rh—N2—C22187.84 (12)C21—C27—C26—C252.1 (4)
Cl—Rh—N2—C221−92.90 (12)C14—C15—C16—C17−1.7 (4)
C31—P—C41—C421.24 (17)F24—C224—C225—C226−179.86 (16)
C51—P—C41—C42112.31 (16)C223—C224—C225—C226−0.7 (3)
Rh—P—C41—C42−123.03 (14)C221—C226—C225—C2242.1 (3)
C31—P—C41—C46−174.68 (13)O1—C11—C17—C16−172.75 (18)
C51—P—C41—C46−63.60 (15)C12—C11—C17—C1610.5 (3)
Rh—P—C41—C4661.05 (14)C15—C16—C17—C112.9 (4)
Rh—O2—C21—C27179.52 (12)C41—C42—C43—C440.0 (3)
Rh—O2—C21—C22−3.39 (18)C12—C13—C14—C151.2 (4)
C111—N1—C12—C139.2 (3)C16—C15—C14—C13−6.3 (4)
Rh—N1—C12—C13−160.07 (13)C226—C221—C222—C2230.5 (3)
C111—N1—C12—C11−175.88 (15)N2—C221—C222—C223179.92 (16)
Rh—N1—C12—C1114.80 (18)C224—C223—C222—C2210.9 (3)
C23—C24—C25—C26−4.6 (3)C56—C55—C54—C53−0.8 (3)
C42—C41—C46—C451.6 (3)C42—C43—C44—C450.7 (3)
P—C41—C46—C45177.74 (14)C46—C45—C44—C43−0.2 (3)
O2—C21—C27—C26−177.45 (18)F14—C114—C113—C112−178.12 (19)
C22—C21—C27—C265.8 (3)C115—C114—C113—C1120.6 (3)
C221—N2—C22—C234.2 (2)C114—C113—C112—C111−1.4 (3)
Rh—N2—C22—C23−166.00 (12)C115—C116—C111—C1120.1 (3)
C221—N2—C22—C21−178.46 (14)C115—C116—C111—N1−174.69 (17)
Rh—N2—C22—C2111.38 (18)C113—C112—C111—C1161.1 (3)
O2—C21—C22—N2−5.2 (2)C113—C112—C111—N1175.79 (17)
C27—C21—C22—N2171.53 (17)C12—N1—C111—C116−126.67 (18)
O2—C21—C22—C23172.07 (15)Rh—N1—C111—C11641.6 (2)
C27—C21—C22—C23−11.2 (3)C12—N1—C111—C11258.6 (2)
C25—C24—C23—C223.1 (3)Rh—N1—C111—C112−133.17 (15)
N2—C22—C23—C24−176.69 (17)C33—C34—C35—C36−1.8 (3)
C21—C22—C23—C246.3 (3)C31—C36—C35—C34−0.7 (3)
C46—C41—C42—C43−1.1 (3)F14—C114—C115—C116179.30 (19)
P—C41—C42—C43−176.91 (13)C113—C114—C115—C1160.6 (3)
C53—C52—C51—C56−1.5 (3)C111—C116—C115—C114−0.9 (3)
C53—C52—C51—P−173.49 (14)C35—C34—C33—C321.2 (3)
C55—C56—C51—C521.9 (3)C31—C32—C33—C341.9 (3)
C55—C56—C51—P173.95 (14)C55—C54—C53—C521.1 (3)
C31—P—C51—C52−149.65 (14)C51—C52—C53—C540.0 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C116—H116···Cl0.952.833.579 (2)137
C17—H17···F14i0.952.393.325 (2)167
C27—H27···F24ii0.952.633.541 (2)162
Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C116—H116···Cl0.952.833.579 (2)137
C17—H17···F14i0.952.393.325 (2)167
C27—H27···F24ii0.952.633.541 (2)162
Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y−1, z.
Acknowledgements top

Financial assistance from the University of the Free State and Professor A. Roodt is gratefully acknowledged. Mr L. Kirsten is acknowledged for the the data collection. Part of this material is based on work supported by the South African National Research Foundation (NRF) under grant No. GUN 2068915. Opinions, findings, conclusions or recommendations expressed in this material are those of the authors and do not necessarily reflect the views of the NRF.

references
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