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Acta Cryst. (2008). E64, m1580-m1581    [ doi:10.1107/S160053680803780X ]

Dicarbonyl[2-hydroxy-3,5,7-tris(morpholinomethyl)cyclohepta-2,4,6-trienonato(1-)-[kappa]2O1,O2]rhodium(I)

T. N. Hill and G. Steyl

Abstract top

In the title compound, [Rh(C22H32N3O5)(CO)2], the RhI atom is coordinated by two carbonyl ligands and two tropolonate O atoms in a distorted square-planar geometry. It is an example of a new type of tropolone derivative that has not been characterized via solid-state methods. Weak intramolecular C-H...N and intermolecular C-H...O hydrogen bonds, and [pi]-[pi] stacking interactions between the tropolone rings [centroid-centroid distance = 3.590 (8) Å] are observed in the crystal structure.

Comment top

Tropolone type compounds have been of interest since its first discovery in the early 1940's (Dewar, 1945), with applications in pharmacology (Banwell et al., 1992; Kierst et al., 1982) and catalysis (Burgstein et al., 1998; Crous et al., 2005). A recent report on the anti-viral activity of morpholine derivatives of tropolone (Doering Knox) indicated moderate to strong activity against the hepatitis C virus strain (Boguszewska-Chachulska et al., 2006). The addition of morpholine groups to a compound increases its water solubilty properties and thus simplifying the method of dosage, i.e., pallative. Although this compound has been extensively studied, the preferred orientation of the morpholine groups are unknown, as well as the geometrical properties of the tropolone ring system. In this regard, we present a dicarbonyl rhodium(I) complex of a 3,5,7-tris(methylmorpholine)tropolonate ligand (Fig. 1; Table 1).

The molecular packing of the title compound is strongly influenced by the morpholine moieties as these form extensive hydrogen bonding networks (Table 2). A close Rh1···Rh1i contact [3.2826 (3)Å; symmetry code: (i) 1-x, y, 0.5-z] exists between associated metal centres. This short contact is stabilized by π–π stacking between the corresponding cycloheptatriene rings, with a centroid–centroid distance of 3.590 (8)Å and an interplanar angle of 3.99 (5)°. The slight twist of the two cycloheptatriene ring systems can be attributed to the methylmorpholine functional groups creating a sterically crowded environment.

The crystal packing of diketonate dicarbonyl rhodium(I) complexes tends to favour a head-to-tail packing mode. The [Rh(tropolonate)(CO)2] complex (Steyl et al., 2004) was deemed to be a singular occurance of the head-to-head packing mode of these molecular systems. The title compound exhibits a slightly distorted orientation as defined by the O1—Rh1—Rh1i—O2i torsion angle of 37.09 (3)°. This observation is surprising since the addition of bulky groups on the 3,7-positions was expected to force the molecular system in the head-to-tail packing mode. The π–π stacking and hydrogen bonding interactions stabilize the crystal structure.

Related literature top

For general background, see: Banwell et al. (1992); Boguszewska-Chachulska et al. (2006); Burgstein et al. (1998); Crous et al. (2005); Dewar (1945); Kierst et al. (1982). For a related structure, see: Steyl et al. (2004).

Experimental top

The title compound was synthesized by the addition of 3,5,7-tris(methylmorpholine)tropolone (0.083 g, 0.32 mmol) to an acetone solution of [Rh(µ-Cl)(CO)2]2 (0.100 g, 0.29 mmol). On slow evaporation of the solvent, crystals suitable for X-ray analysis was obtained (yield 30%, 0.045 g).

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.95 (CH) and 0.99 (CH2) Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
Dicarbonyl[2-hydroxy-3,5,7-tris(morpholinomethyl)cyclohepta-2,4,6- trienonato(1-)-κ2O1,O2]rhodium(I) top
Crystal data top
[Rh(C22H32N3O5)(CO)2]F(000) = 2384
Mr = 577.44Dx = 1.522 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7078 reflections
a = 17.7889 (6) Åθ = 2.4–26.3°
b = 16.6106 (5) ŵ = 0.73 mm−1
c = 17.7279 (4) ÅT = 100 K
β = 105.772 (1)°Needle, yellow
V = 5041.1 (3) Å30.15 × 0.06 × 0.05 mm
Z = 8
Data collection top
Bruker X8 APEXII Kappa CCD
diffractometer		5450 independent reflections
Radiation source: sealed tube4616 reflections with I > 2σ(I)
graphiteRint = 0.06
ω and φ scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −23→22
Tmin = 0.901, Tmax = 0.966k = −22→22
36747 measured reflectionsl = −23→21
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0228P)2 + 6.7535P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.070(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.57 e Å−3
5450 reflectionsΔρmin = −0.55 e Å−3
316 parameters
Crystal data top
[Rh(C22H32N3O5)(CO)2]V = 5041.1 (3) Å3
Mr = 577.44Z = 8
Monoclinic, C2/cMo Kα radiation
a = 17.7889 (6) ŵ = 0.73 mm−1
b = 16.6106 (5) ÅT = 100 K
c = 17.7279 (4) Å0.15 × 0.06 × 0.05 mm
β = 105.772 (1)°
Data collection top
Bruker X8 APEXII Kappa CCD
diffractometer		5450 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		4616 reflections with I > 2σ(I)
Tmin = 0.901, Tmax = 0.966Rint = 0.06
36747 measured reflectionsθmax = 27.0°
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.070Δρmax = 0.57 e Å−3
S = 1.01Δρmin = −0.55 e Å−3
5450 reflectionsAbsolute structure: ?
316 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Rh10.005201 (12)0.212518 (10)0.158973 (11)0.01523 (6)
N32−0.29013 (12)0.40449 (12)0.14152 (12)0.0184 (4)
N52−0.09972 (13)0.68641 (11)0.11782 (12)0.0193 (5)
N720.12652 (12)0.55064 (11)0.12939 (11)0.0161 (4)
O1−0.09251 (10)0.27724 (9)0.15271 (9)0.0164 (4)
O20.04571 (10)0.32572 (9)0.15522 (9)0.0168 (4)
O35−0.44856 (11)0.45215 (11)0.09597 (11)0.0291 (4)
O55−0.14421 (12)0.81072 (10)0.00353 (12)0.0338 (5)
O750.19657 (11)0.67733 (10)0.06510 (10)0.0272 (4)
C010.10082 (16)0.16569 (13)0.16882 (14)0.0186 (5)
C02−0.04121 (15)0.11321 (14)0.15654 (14)0.0191 (5)
O010.16289 (11)0.14149 (10)0.17892 (10)0.0266 (4)
O02−0.07249 (11)0.05334 (10)0.15587 (11)0.0271 (4)
C1−0.00561 (14)0.38233 (13)0.15364 (13)0.0139 (5)
C2−0.08253 (15)0.35538 (13)0.15345 (13)0.0153 (5)
C3−0.14821 (14)0.40295 (13)0.15290 (13)0.0148 (5)
C4−0.15152 (15)0.48618 (13)0.15770 (13)0.0164 (5)
H4−0.20130.50660.1580.02*
C5−0.09482 (14)0.54493 (13)0.16221 (13)0.0153 (5)
C6−0.01989 (14)0.53233 (14)0.15582 (13)0.0154 (5)
H60.00940.58030.15650.018*
C70.02014 (14)0.46255 (13)0.14867 (13)0.0144 (5)
C31−0.22148 (14)0.35437 (14)0.15082 (15)0.0201 (5)
H31A−0.2310.31550.10690.024*
H31B−0.21270.32320.20010.024*
C33−0.34489 (15)0.37470 (14)0.18290 (15)0.0212 (6)
H33A−0.31750.36570.23880.025*
H33B−0.36750.32280.160.025*
C34−0.40884 (16)0.43614 (16)0.17571 (16)0.0263 (6)
H34A−0.44680.41610.20310.032*
H34B−0.3860.48680.20150.032*
C36−0.39560 (15)0.47768 (15)0.05269 (15)0.0236 (6)
H36A−0.37270.53030.0730.028*
H36B−0.42450.4848−0.00310.028*
C37−0.33140 (15)0.41744 (15)0.05905 (14)0.0222 (6)
H37A−0.35370.36590.0350.027*
H37B−0.29440.43740.03050.027*
C51−0.11655 (15)0.63133 (13)0.17494 (14)0.0184 (5)
H51A−0.1730.63390.17160.022*
H51B−0.08730.64860.22830.022*
C53−0.15194 (17)0.67127 (14)0.04011 (14)0.0239 (6)
H53A−0.20690.67740.04160.029*
H53B−0.14470.61550.02380.029*
C54−0.1347 (2)0.72976 (16)−0.01803 (17)0.0348 (7)
H54A−0.08040.7217−0.0210.042*
H54B−0.17030.719−0.07060.042*
C56−0.09308 (18)0.82638 (16)0.07909 (17)0.0344 (7)
H56A−0.10010.88270.09430.041*
H56B−0.03830.81980.07730.041*
C57−0.10926 (17)0.76990 (14)0.13928 (16)0.0267 (6)
H57A−0.07290.78150.19120.032*
H57B−0.16320.77830.1430.032*
C710.10184 (14)0.46875 (13)0.13924 (14)0.0159 (5)
H71A0.13880.44490.1860.019*
H71B0.10470.43650.09310.019*
C730.09197 (15)0.58095 (14)0.04982 (14)0.0186 (5)
H73A0.03440.57560.03610.022*
H73B0.11150.54930.01170.022*
C740.11413 (16)0.66843 (14)0.04648 (15)0.0226 (6)
H74A0.09020.6898−0.00680.027*
H74B0.09370.69990.0840.027*
C760.23202 (16)0.64617 (15)0.14098 (15)0.0254 (6)
H76A0.21480.67820.18040.031*
H76B0.28950.65140.15240.031*
C770.21100 (15)0.55855 (14)0.14762 (15)0.0214 (6)
H77A0.2310.52560.11070.026*
H77B0.23530.53890.20150.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rh10.01874 (11)0.01015 (9)0.01714 (10)0.00082 (8)0.00544 (7)0.00046 (8)
N320.0151 (12)0.0180 (10)0.0232 (11)0.0017 (8)0.0071 (9)0.0042 (8)
N520.0243 (13)0.0108 (9)0.0241 (12)0.0005 (8)0.0087 (9)0.0007 (8)
N720.0160 (12)0.0147 (10)0.0173 (11)−0.0031 (8)0.0044 (9)0.0002 (8)
O10.0176 (9)0.0104 (8)0.0215 (9)−0.0011 (7)0.0059 (7)0.0009 (6)
O20.0169 (10)0.0116 (8)0.0234 (9)0.0009 (7)0.0082 (7)0.0007 (7)
O350.0178 (11)0.0348 (11)0.0350 (11)0.0033 (8)0.0075 (9)0.0029 (8)
O550.0412 (14)0.0205 (10)0.0409 (12)0.0053 (9)0.0134 (10)0.0108 (8)
O750.0316 (12)0.0229 (9)0.0280 (11)−0.0096 (8)0.0094 (9)0.0049 (8)
C010.0276 (16)0.0111 (11)0.0180 (13)−0.0013 (11)0.0075 (11)−0.0012 (9)
C020.0227 (15)0.0181 (13)0.0178 (13)0.0044 (11)0.0074 (11)0.0012 (10)
O010.0241 (12)0.0217 (9)0.0331 (11)0.0048 (8)0.0065 (9)0.0003 (8)
O020.0307 (12)0.0167 (9)0.0368 (11)−0.0040 (8)0.0141 (9)−0.0027 (8)
C10.0171 (14)0.0143 (11)0.0112 (11)−0.0002 (10)0.0055 (10)−0.0017 (9)
C20.0229 (14)0.0124 (11)0.0102 (11)−0.0016 (10)0.0036 (10)0.0013 (9)
C30.0163 (13)0.0152 (11)0.0136 (12)−0.0015 (10)0.0053 (10)0.0029 (9)
C40.0174 (14)0.0169 (12)0.0150 (12)0.0032 (10)0.0047 (10)0.0014 (9)
C50.0191 (14)0.0134 (11)0.0134 (12)0.0003 (10)0.0042 (10)0.0002 (9)
C60.0195 (14)0.0147 (11)0.0124 (12)−0.0032 (10)0.0052 (10)−0.0004 (9)
C70.0150 (14)0.0167 (11)0.0112 (12)−0.0031 (9)0.0028 (9)−0.0020 (9)
C310.0186 (14)0.0156 (12)0.0266 (14)−0.0001 (10)0.0069 (11)0.0029 (10)
C330.0209 (15)0.0174 (12)0.0274 (14)−0.0023 (10)0.0102 (11)0.0027 (10)
C340.0248 (16)0.0270 (14)0.0319 (16)0.0018 (12)0.0160 (13)0.0032 (11)
C360.0230 (16)0.0245 (14)0.0227 (14)0.0035 (11)0.0051 (11)0.0013 (11)
C370.0216 (15)0.0230 (13)0.0224 (14)0.0026 (11)0.0068 (11)−0.0003 (10)
C510.0223 (15)0.0149 (11)0.0196 (13)0.0022 (10)0.0083 (11)−0.0022 (10)
C530.0314 (17)0.0162 (12)0.0242 (14)0.0038 (11)0.0075 (12)0.0005 (10)
C540.049 (2)0.0275 (15)0.0313 (16)0.0108 (13)0.0167 (14)0.0063 (12)
C560.0318 (18)0.0175 (13)0.052 (2)−0.0038 (12)0.0075 (15)0.0067 (12)
C570.0326 (17)0.0140 (12)0.0319 (15)0.0007 (11)0.0060 (12)−0.0026 (10)
C710.0185 (14)0.0131 (11)0.0163 (12)−0.0027 (10)0.0054 (10)−0.0018 (9)
C730.0207 (15)0.0176 (12)0.0172 (13)−0.0026 (10)0.0045 (10)−0.0004 (9)
C740.0294 (17)0.0188 (13)0.0188 (13)−0.0043 (11)0.0050 (11)0.0003 (10)
C760.0214 (15)0.0232 (13)0.0309 (15)−0.0067 (11)0.0057 (12)0.0027 (11)
C770.0193 (15)0.0186 (12)0.0261 (14)−0.0026 (10)0.0060 (11)0.0000 (10)
Geometric parameters (Å, °) top
Rh1—C011.835 (3)C31—H31B0.99
Rh1—C021.840 (2)C33—C341.508 (3)
Rh1—O12.0209 (16)C33—H33A0.99
Rh1—O22.0212 (15)C33—H33B0.99
N32—C311.450 (3)C34—H34A0.99
N32—C331.456 (3)C34—H34B0.99
N32—C371.463 (3)C36—C371.499 (3)
N52—C511.455 (3)C36—H36A0.99
N52—C531.459 (3)C36—H36B0.99
N52—C571.460 (3)C37—H37A0.99
N72—C711.454 (3)C37—H37B0.99
N72—C771.455 (3)C51—H51A0.99
N72—C731.466 (3)C51—H51B0.99
O1—C21.310 (3)C53—C541.507 (4)
O2—C11.306 (3)C53—H53A0.99
O35—C341.423 (3)C53—H53B0.99
O35—C361.431 (3)C54—H54A0.99
O55—C541.421 (3)C54—H54B0.99
O55—C561.424 (3)C56—C571.506 (4)
O75—C761.419 (3)C56—H56A0.99
O75—C741.421 (3)C56—H56B0.99
C01—O011.143 (3)C57—H57A0.99
C02—O021.138 (3)C57—H57B0.99
C1—C71.419 (3)C71—H71A0.99
C1—C21.439 (3)C71—H71B0.99
C2—C31.408 (3)C73—C741.511 (3)
C3—C41.387 (3)C73—H73A0.99
C3—C311.525 (3)C73—H73B0.99
C4—C51.390 (3)C74—H74A0.99
C4—H40.95C74—H74B0.99
C5—C61.384 (3)C76—C771.515 (3)
C5—C511.519 (3)C76—H76A0.99
C6—C71.384 (3)C76—H76B0.99
C6—H60.95C77—H77A0.99
C7—C711.511 (3)C77—H77B0.99
C31—H31A0.99
C01—Rh1—C0291.18 (11)N32—C37—C36109.8 (2)
C01—Rh1—O1172.67 (8)N32—C37—H37A109.7
C02—Rh1—O195.85 (9)C36—C37—H37A109.7
C01—Rh1—O293.89 (9)N32—C37—H37B109.7
C02—Rh1—O2174.27 (9)C36—C37—H37B109.7
O1—Rh1—O279.18 (6)H37A—C37—H37B108.2
C31—N32—C33113.94 (19)N52—C51—C5112.45 (19)
C31—N32—C37112.11 (19)N52—C51—H51A109.1
C33—N32—C37109.3 (2)C5—C51—H51A109.1
C51—N52—C53110.49 (19)N52—C51—H51B109.1
C51—N52—C57110.82 (19)C5—C51—H51B109.1
C53—N52—C57108.7 (2)H51A—C51—H51B107.8
C71—N72—C77112.65 (19)N52—C53—C54109.8 (2)
C71—N72—C73112.05 (18)N52—C53—H53A109.7
C77—N72—C73108.68 (19)C54—C53—H53A109.7
C2—O1—Rh1114.49 (15)N52—C53—H53B109.7
C1—O2—Rh1114.66 (14)C54—C53—H53B109.7
C34—O35—C36111.5 (2)H53A—C53—H53B108.2
C54—O55—C56109.5 (2)O55—C54—C53111.4 (2)
C76—O75—C74110.30 (19)O55—C54—H54A109.3
O01—C01—Rh1174.5 (2)C53—C54—H54A109.3
O02—C02—Rh1177.1 (2)O55—C54—H54B109.3
O2—C1—C7116.2 (2)C53—C54—H54B109.3
O2—C1—C2115.77 (19)H54A—C54—H54B108
C7—C1—C2127.9 (2)O55—C56—C57110.9 (2)
O1—C2—C3116.5 (2)O55—C56—H56A109.5
O1—C2—C1115.8 (2)C57—C56—H56A109.5
C3—C2—C1127.7 (2)O55—C56—H56B109.5
C4—C3—C2127.4 (2)C57—C56—H56B109.5
C4—C3—C31118.6 (2)H56A—C56—H56B108
C2—C3—C31113.90 (19)N52—C57—C56110.4 (2)
C3—C4—C5131.4 (2)N52—C57—H57A109.6
C3—C4—H4114.3C56—C57—H57A109.6
C5—C4—H4114.3N52—C57—H57B109.6
C6—C5—C4126.1 (2)C56—C57—H57B109.6
C6—C5—C51116.4 (2)H57A—C57—H57B108.1
C4—C5—C51117.5 (2)N72—C71—C7114.07 (19)
C7—C6—C5131.7 (2)N72—C71—H71A108.7
C7—C6—H6114.2C7—C71—H71A108.7
C5—C6—H6114.2N72—C71—H71B108.7
C6—C7—C1126.7 (2)C7—C71—H71B108.7
C6—C7—C71119.2 (2)H71A—C71—H71B107.6
C1—C7—C71114.0 (2)N72—C73—C74108.80 (19)
N32—C31—C3112.75 (19)N72—C73—H73A109.9
N32—C31—H31A109C74—C73—H73A109.9
C3—C31—H31A109N72—C73—H73B109.9
N32—C31—H31B109C74—C73—H73B109.9
C3—C31—H31B109H73A—C73—H73B108.3
H31A—C31—H31B107.8O75—C74—C73110.8 (2)
N32—C33—C34108.66 (19)O75—C74—H74A109.5
N32—C33—H33A110C73—C74—H74A109.5
C34—C33—H33A110O75—C74—H74B109.5
N32—C33—H33B110C73—C74—H74B109.5
C34—C33—H33B110H74A—C74—H74B108.1
H33A—C33—H33B108.3O75—C76—C77111.6 (2)
O35—C34—C33111.7 (2)O75—C76—H76A109.3
O35—C34—H34A109.3C77—C76—H76A109.3
C33—C34—H34A109.3O75—C76—H76B109.3
O35—C34—H34B109.3C77—C76—H76B109.3
C33—C34—H34B109.3H76A—C76—H76B108
H34A—C34—H34B107.9N72—C77—C76109.4 (2)
O35—C36—C37111.1 (2)N72—C77—H77A109.8
O35—C36—H36A109.4C76—C77—H77A109.8
C37—C36—H36A109.4N72—C77—H77B109.8
O35—C36—H36B109.4C76—C77—H77B109.8
C37—C36—H36B109.4H77A—C77—H77B108.3
H36A—C36—H36B108
C02—Rh1—O1—C2179.63 (15)C31—N32—C33—C34174.1 (2)
O2—Rh1—O1—C2−3.26 (14)C37—N32—C33—C34−59.6 (3)
C01—Rh1—O2—C1−175.31 (16)C36—O35—C34—C33−56.2 (3)
O1—Rh1—O2—C12.28 (15)N32—C33—C34—O3558.3 (3)
Rh1—O2—C1—C7−178.22 (15)C34—O35—C36—C3755.3 (3)
Rh1—O2—C1—C2−1.0 (2)C31—N32—C37—C36−172.9 (2)
Rh1—O1—C2—C3−177.12 (15)C33—N32—C37—C3659.7 (3)
Rh1—O1—C2—C13.7 (2)O35—C36—C37—N32−57.1 (3)
O2—C1—C2—O1−1.8 (3)C53—N52—C51—C568.7 (3)
C7—C1—C2—O1175.0 (2)C57—N52—C51—C5−170.8 (2)
O2—C1—C2—C3179.1 (2)C6—C5—C51—N5251.4 (3)
C7—C1—C2—C3−4.1 (4)C4—C5—C51—N52−128.3 (2)
O1—C2—C3—C4176.3 (2)C51—N52—C53—C54179.0 (2)
C1—C2—C3—C4−4.7 (4)C57—N52—C53—C5457.2 (3)
O1—C2—C3—C31−0.5 (3)C56—O55—C54—C5359.1 (3)
C1—C2—C3—C31178.6 (2)N52—C53—C54—O55−59.1 (3)
C2—C3—C4—C51.8 (4)C54—O55—C56—C57−58.6 (3)
C31—C3—C4—C5178.4 (2)C51—N52—C57—C56−179.0 (2)
C3—C4—C5—C66.2 (4)C53—N52—C57—C56−57.4 (3)
C3—C4—C5—C51−174.1 (2)O55—C56—C57—N5258.8 (3)
C4—C5—C6—C7−4.5 (4)C77—N72—C71—C7159.88 (19)
C51—C5—C6—C7175.8 (2)C73—N72—C71—C7−77.2 (2)
C5—C6—C7—C1−6.5 (4)C6—C7—C71—N72−6.9 (3)
C5—C6—C7—C71177.4 (2)C1—C7—C71—N72176.48 (19)
O2—C1—C7—C6−171.5 (2)C71—N72—C73—C74174.7 (2)
C2—C1—C7—C611.7 (4)C77—N72—C73—C74−60.2 (2)
O2—C1—C7—C714.8 (3)C76—O75—C74—C73−58.6 (3)
C2—C1—C7—C71−172.0 (2)N72—C73—C74—O7560.3 (3)
C33—N32—C31—C3−145.6 (2)C74—O75—C76—C7757.3 (3)
C37—N32—C31—C389.6 (2)C71—N72—C77—C76−176.41 (19)
C4—C3—C31—N329.4 (3)C73—N72—C77—C7658.8 (2)
C2—C3—C31—N32−173.6 (2)O75—C76—C77—N72−57.9 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4···N320.952.282.760 (3)110
C6—H6···N720.952.312.785 (3)110
C36—H36A···O01i0.992.593.497 (3)153
C53—H53A···O55ii0.992.563.509 (4)161
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x−1/2, −y+3/2, −z.
Table 1
Selected geometric parameters (Å) top
Rh1—C011.835 (3)Rh1—O12.0209 (16)
Rh1—C021.840 (2)Rh1—O22.0212 (15)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4···N320.952.282.760 (3)110
C6—H6···N720.952.312.785 (3)110
C36—H36A···O01i0.992.593.497 (3)153
C53—H53A···O55ii0.992.563.509 (4)161
Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x−1/2, −y+3/2, −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 data collection. Part of this research is based on work supported by the South African National Research Foundation (NRF) (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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