(N-Benzoyl-N-phenyl­hydroxy­laminato)carbon­yl(tri­phenyl­arsine)rhodium(I)

Motente, M.A.; Venter, J.; Brink, A.

doi:10.1107/S2414314623003553

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 8| Part 4| April 2023| x230355

https://doi.org/10.1107/S2414314623003553

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(N-Benzoyl-N-phenylhydroxylaminato)carbonyl(triphenylarsine)rhodium(I)

Mokete A. Motente,^a ^* Johan Venter ^a and Alice Brink ^a

^aDepartment of Chemistry, University of the Free State, Bloemfontein, 9301, South Africa
^*Correspondence e-mail: mokete.motente@gmail.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 28 March 2023; accepted 18 April 2023; online 25 April 2023)

This article is part of a collection of articles to commemorate the founding of the African Crystallographic Association and the 75th anniversary of the IUCr.

The molecule of the title compound, [Rh(C₁₃H₁₀NO₂){As(C₆H₅)₃}(CO)] or [Rh(BPHA)(AsPh₃)(CO)] (BPHA is the N-benzoyl-N-phenylhydroxylaminate anion), comprises a bidentate N-benzoyl-N-phenylhydroxylaminate anion coordinating through the O atoms to the soft Lewis acid, rhodium(I), and two monodentate ligands, viz. triphenylarsine and carbonyl. The resulting CO₂As coordination environment around the central Rh^I atom is distorted square planar.=

Keywords: crystal structure; rhodium; N-benzoyl-N-phenylhydroxamic acid; triphenylarsine.

CCDC reference: 2257230

Structure description

The title complex, [Rh(BPHA)(AsPh₃)(CO)], is composed of an O,O-bidentate N-benzoyl-N-phenylhydroxylaminate anion, a carbonyl ligand and a monodentate triphenylarsine ligand, all coordinating to the soft rhodium(I) metal atom (Fig. 1 and Table 1). The crystal structure is isotypic with that of [Rh(BPHA)(PPh₃)(CO)] and shows similar Rh—O and Rh—C bond lengths (2.037/2.089 and 1.809 Å, respectively; Leipoldt & Grobler, 1982 ). The coordination environment in the molecule of [Rh(BPHA)(AsPh₃)(CO)] is distorted square planar, as shown by the small O1—Rh—O2 bite angle of 79.53 (7)°, which is similar to the bite angles of related structures with O,O-binding five-membered chelate rings reported in the literature (Elmakki et al., 2017 ). The C02—Rh—O2 and C02—Rh—O1 angles involving the C02≡O02 carbonyl ligand were also found to deviate from ideal values, at 99.31 (9) and 178.39 (10)°, respectively, similar to those of related structures (Elmakki et al., 2016 ).

Table 1
Selected bond lengths (Å)

Rh1—As	2.3337 (4)	Rh1—O1	2.0338 (18)
Rh1—O2	2.0682 (17)	Rh1—C02	1.813 (3)

Figure 1
The molecular structure of the title compound, showing atoms with displacement ellipsoids at the 50% probability level.

The crystal packing is dominated by van der Waals interactions (Fig. 2).

Figure 2
An illustration of the molecular packing in the unit cell of [Rh(BPHA)(CO)(AsPh₃)], viewed approximately along the a axis; atom labels have been omitted for clarity.

Synthesis and crystallization

A stepwise process was pursued in the complexation of the rhodium metal atom by the bidentate N-phenyl-N-benzoylhydroxylaminate anion. First, [RhCl(CO)₂]₂ was prepared in situ by heating RhCl₃·3H₂O in 5 ml of dimethylformamide under reflux for 30 min, followed by addition of the bidentate ligand to the reaction mixture, which then resulted in the formation of a dicarbonylrhodium species, [Rh(BPHA)(CO)₂] (Leipoldt & Grobler, 1982). Rh(BPHA)(CO)₂] (65 mg) was then dissolved in 5 ml of acetone. Triphenylarsine (AsPh₃; 70 mg) was added to the reaction mixture under stirring, resulting in the immediate evolution of CO gas. The reaction mixture was then left to crystallize, resulting in the formation of yellow crystals suitable for X-ray analysis.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Rh(C₁₃H₁₀NO₂)(C₁₈H₁₅As)(CO)]
M_r	649.36
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	9.5178 (17), 10.1995 (19), 14.589 (2)
α, β, γ (°)	81.516 (6), 83.142 (6), 72.351 (7)
V (Å³)	1330.7 (4)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.91
Crystal size (mm)	0.21 × 0.13 × 0.03

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.634, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	38485, 6425, 5747
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.074, 1.07
No. of reflections	6425
No. of parameters	343
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.14, −0.61
Computer programs: APEX2 and SAINT (Bruker, 2012 ), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ) and DIAMOND (Brandenburg & Putz, 2005 ).

Structural data

CCDC reference: 2257230

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314623003553/wm4184sup1.cif

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009) and DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(N-Benzoyl-N-phenylhydroxylaminato)carbonyl(triphenylarsine)rhodium(I) top

Crystal data top

[Rh(C₁₃H₁₀NO₂)(C₁₈H₁₅As)(CO)]	Z = 2
M_r = 649.36	F(000) = 652
Triclinic, P1	D_x = 1.621 Mg m⁻³
a = 9.5178 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1995 (19) Å	Cell parameters from 9339 reflections
c = 14.589 (2) Å	θ = 2.3–28.3°
α = 81.516 (6)°	µ = 1.91 mm⁻¹
β = 83.142 (6)°	T = 100 K
γ = 72.351 (7)°	Plate, yellow
V = 1330.7 (4) Å³	0.21 × 0.13 × 0.03 mm

Data collection top

Bruker APEXII CCD diffractometer	5747 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.065
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 28.0°, θ_min = 2.1°
T_min = 0.634, T_max = 0.746	h = −12→12
38485 measured reflections	k = −13→13
6425 independent reflections	l = −19→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.074	w = 1/[σ²(F_o²) + (0.0141P)² + 1.8613P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.002
6425 reflections	Δρ_max = 1.14 e Å⁻³
343 parameters	Δρ_min = −0.61 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Rh1	0.25715 (2)	0.53736 (2)	0.27266 (2)	0.01779 (6)
As	0.12957 (3)	0.72691 (2)	0.35181 (2)	0.01699 (6)
O2	0.39711 (19)	0.38301 (18)	0.19949 (12)	0.0210 (4)
O1	0.42339 (19)	0.62308 (18)	0.22612 (13)	0.0217 (4)
O02	0.0140 (2)	0.4121 (2)	0.33366 (15)	0.0313 (4)
N1	0.5303 (2)	0.5365 (2)	0.17371 (15)	0.0207 (4)
C1	0.5119 (3)	0.4183 (2)	0.15914 (16)	0.0169 (4)
C26	−0.0798 (3)	0.7588 (2)	0.38511 (18)	0.0197 (5)
C8	0.6478 (3)	0.5925 (3)	0.13234 (17)	0.0198 (5)
C14	0.2129 (3)	0.7244 (3)	0.46672 (17)	0.0189 (5)
C20	0.1411 (3)	0.9043 (3)	0.28753 (17)	0.0207 (5)
C15	0.2025 (3)	0.8463 (3)	0.50321 (19)	0.0241 (5)
H15	0.1470	0.9331	0.4741	0.029*
C7	0.6819 (3)	0.3597 (3)	0.01447 (18)	0.0212 (5)
H7	0.6631	0.4551	−0.0082	0.025*
C27	−0.1418 (3)	0.7798 (3)	0.47479 (19)	0.0237 (5)
H27	−0.0816	0.7815	0.5218	0.028*
C13	0.6118 (3)	0.7151 (3)	0.07297 (19)	0.0241 (5)
H13	0.5113	0.7637	0.0637	0.029*
C2	0.6182 (3)	0.3193 (3)	0.10122 (17)	0.0190 (5)
C19	0.2907 (3)	0.5971 (3)	0.51116 (18)	0.0237 (5)
H19	0.2958	0.5138	0.4873	0.028*
C02	0.1092 (3)	0.4594 (3)	0.31095 (18)	0.0224 (5)
C6	0.7729 (3)	0.2591 (3)	−0.03845 (19)	0.0250 (5)
H6	0.8153	0.2862	−0.0978	0.030*
C28	−0.2931 (3)	0.7983 (3)	0.4956 (2)	0.0304 (6)
H28	−0.3356	0.8119	0.5570	0.036*
C9	0.7931 (3)	0.5246 (3)	0.15114 (19)	0.0232 (5)
H9	0.8160	0.4439	0.1950	0.028*
C3	0.6475 (3)	0.1796 (3)	0.13401 (19)	0.0247 (5)
H3	0.6039	0.1518	0.1928	0.030*
C18	0.3607 (3)	0.5920 (3)	0.59044 (19)	0.0280 (6)
H18	0.4137	0.5054	0.6211	0.034*
C11	0.8703 (3)	0.6955 (3)	0.0429 (2)	0.0296 (6)
H11	0.9472	0.7295	0.0106	0.036*
C31	−0.1692 (3)	0.7556 (3)	0.3171 (2)	0.0268 (6)
H31	−0.1268	0.7393	0.2559	0.032*
C12	0.7241 (3)	0.7658 (3)	0.0274 (2)	0.0290 (6)
H12	0.7011	0.8487	−0.0144	0.035*
C16	0.2733 (3)	0.8406 (3)	0.58217 (19)	0.0284 (6)
H16	0.2669	0.9234	0.6069	0.034*
C4	0.7403 (3)	0.0805 (3)	0.0812 (2)	0.0298 (6)
H4	0.7616	−0.0149	0.1044	0.036*
C10	0.9049 (3)	0.5768 (3)	0.1046 (2)	0.0275 (6)
H10	1.0053	0.5304	0.1155	0.033*
C17	0.3531 (3)	0.7141 (3)	0.6246 (2)	0.0301 (6)
H17	0.4033	0.7106	0.6779	0.036*
C5	0.8022 (3)	0.1204 (3)	−0.0057 (2)	0.0300 (6)
H5	0.8644	0.0523	−0.0423	0.036*
C29	−0.3810 (3)	0.7971 (3)	0.4275 (2)	0.0332 (6)
H29	−0.4841	0.8107	0.4420	0.040*
C25	0.2759 (3)	0.9299 (3)	0.2743 (2)	0.0390 (7)
H25	0.3614	0.8592	0.2938	0.047*
C24	0.2892 (4)	1.0577 (4)	0.2327 (2)	0.0417 (8)
H24	0.3829	1.0747	0.2256	0.050*
C21	0.0196 (3)	1.0048 (3)	0.2526 (2)	0.0324 (6)
H21	−0.0736	0.9871	0.2583	0.039*
C23	0.1672 (4)	1.1593 (3)	0.2019 (2)	0.0368 (7)
H23	0.1750	1.2480	0.1759	0.044*
C30	−0.3194 (3)	0.7760 (3)	0.3380 (2)	0.0340 (7)
H30	−0.3802	0.7755	0.2911	0.041*
C22	0.0335 (4)	1.1316 (3)	0.2091 (3)	0.0442 (8)
H22	−0.0499	1.1994	0.1841	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Rh1	0.01456 (9)	0.02186 (10)	0.01630 (10)	−0.00485 (7)	0.00038 (7)	−0.00246 (7)
As	0.01309 (12)	0.02045 (12)	0.01611 (13)	−0.00335 (9)	−0.00019 (9)	−0.00199 (9)
O2	0.0163 (8)	0.0257 (9)	0.0210 (9)	−0.0066 (7)	0.0018 (7)	−0.0040 (7)
O1	0.0176 (8)	0.0245 (9)	0.0235 (10)	−0.0066 (7)	0.0048 (7)	−0.0087 (7)
O02	0.0258 (10)	0.0340 (10)	0.0364 (12)	−0.0152 (8)	0.0031 (8)	−0.0022 (9)
N1	0.0172 (10)	0.0252 (10)	0.0200 (11)	−0.0067 (8)	0.0012 (8)	−0.0046 (8)
C1	0.0154 (11)	0.0209 (11)	0.0138 (11)	−0.0045 (9)	−0.0014 (8)	−0.0012 (8)
C26	0.0126 (10)	0.0187 (11)	0.0253 (13)	−0.0023 (8)	0.0003 (9)	−0.0014 (9)
C8	0.0196 (11)	0.0245 (12)	0.0178 (12)	−0.0091 (9)	0.0011 (9)	−0.0066 (9)
C14	0.0139 (11)	0.0261 (12)	0.0159 (12)	−0.0045 (9)	−0.0007 (9)	−0.0031 (9)
C20	0.0212 (12)	0.0222 (11)	0.0182 (12)	−0.0065 (9)	0.0007 (9)	−0.0019 (9)
C15	0.0234 (13)	0.0254 (12)	0.0220 (13)	−0.0053 (10)	−0.0005 (10)	−0.0033 (10)
C7	0.0176 (11)	0.0281 (12)	0.0190 (12)	−0.0074 (10)	−0.0039 (9)	−0.0023 (9)
C27	0.0212 (12)	0.0280 (13)	0.0215 (13)	−0.0086 (10)	0.0014 (10)	−0.0014 (10)
C13	0.0223 (12)	0.0258 (12)	0.0260 (14)	−0.0085 (10)	−0.0019 (10)	−0.0056 (10)
C2	0.0144 (11)	0.0244 (12)	0.0191 (12)	−0.0053 (9)	−0.0025 (9)	−0.0056 (9)
C19	0.0224 (12)	0.0245 (12)	0.0218 (13)	−0.0039 (10)	−0.0005 (10)	−0.0024 (10)
C02	0.0218 (12)	0.0228 (12)	0.0191 (13)	−0.0018 (10)	−0.0015 (10)	−0.0019 (9)
C6	0.0183 (12)	0.0381 (14)	0.0191 (13)	−0.0076 (11)	−0.0006 (10)	−0.0074 (10)
C28	0.0236 (13)	0.0376 (15)	0.0277 (15)	−0.0089 (11)	0.0093 (11)	−0.0058 (12)
C9	0.0202 (12)	0.0259 (12)	0.0235 (13)	−0.0059 (10)	−0.0029 (10)	−0.0042 (10)
C3	0.0257 (13)	0.0275 (13)	0.0218 (13)	−0.0086 (10)	−0.0020 (10)	−0.0038 (10)
C18	0.0286 (14)	0.0314 (13)	0.0204 (14)	−0.0045 (11)	−0.0044 (11)	0.0010 (10)
C11	0.0248 (13)	0.0402 (15)	0.0294 (15)	−0.0187 (12)	0.0039 (11)	−0.0069 (12)
C31	0.0197 (12)	0.0335 (14)	0.0267 (14)	−0.0051 (10)	−0.0008 (10)	−0.0087 (11)
C12	0.0314 (14)	0.0333 (14)	0.0258 (15)	−0.0154 (12)	−0.0009 (11)	−0.0023 (11)
C16	0.0336 (15)	0.0320 (14)	0.0210 (14)	−0.0097 (12)	−0.0012 (11)	−0.0083 (11)
C4	0.0307 (14)	0.0233 (12)	0.0339 (16)	−0.0036 (11)	−0.0030 (12)	−0.0074 (11)
C10	0.0185 (12)	0.0381 (15)	0.0286 (15)	−0.0095 (11)	0.0004 (10)	−0.0115 (11)
C17	0.0311 (15)	0.0407 (16)	0.0190 (14)	−0.0101 (12)	−0.0046 (11)	−0.0040 (11)
C5	0.0222 (13)	0.0328 (14)	0.0337 (16)	−0.0007 (11)	−0.0025 (11)	−0.0153 (12)
C29	0.0153 (12)	0.0405 (16)	0.0431 (18)	−0.0075 (11)	0.0029 (12)	−0.0081 (13)
C25	0.0228 (14)	0.0416 (17)	0.048 (2)	−0.0094 (12)	−0.0029 (13)	0.0112 (14)
C24	0.0386 (17)	0.0452 (18)	0.046 (2)	−0.0252 (15)	0.0003 (15)	0.0052 (15)
C21	0.0230 (13)	0.0269 (13)	0.0418 (18)	−0.0032 (11)	0.0029 (12)	0.0005 (12)
C23	0.0518 (19)	0.0258 (13)	0.0319 (17)	−0.0152 (13)	0.0118 (14)	−0.0041 (12)
C30	0.0199 (13)	0.0419 (16)	0.0415 (18)	−0.0075 (12)	−0.0050 (12)	−0.0101 (13)
C22	0.0405 (18)	0.0228 (14)	0.058 (2)	0.0006 (13)	0.0035 (16)	0.0053 (14)

Geometric parameters (Å, º) top

Rh1—As	2.3337 (4)	C6—C5	1.379 (4)
Rh1—O2	2.0682 (17)	C28—H28	0.9500
Rh1—O1	2.0338 (18)	C28—C29	1.376 (4)
Rh1—C02	1.813 (3)	C9—H9	0.9500
As—C26	1.933 (2)	C9—C10	1.395 (4)
As—C14	1.932 (2)	C3—H3	0.9500
As—C20	1.939 (2)	C3—C4	1.386 (4)
O2—C1	1.301 (3)	C18—H18	0.9500
O1—N1	1.367 (3)	C18—C17	1.387 (4)
O02—C02	1.144 (3)	C11—H11	0.9500
N1—C1	1.319 (3)	C11—C12	1.387 (4)
N1—C8	1.437 (3)	C11—C10	1.375 (4)
C1—C2	1.479 (3)	C31—H31	0.9500
C26—C27	1.388 (4)	C31—C30	1.384 (4)
C26—C31	1.392 (4)	C12—H12	0.9500
C8—C13	1.387 (4)	C16—H16	0.9500
C8—C9	1.385 (4)	C16—C17	1.381 (4)
C14—C15	1.395 (3)	C4—H4	0.9500
C14—C19	1.393 (3)	C4—C5	1.391 (4)
C20—C25	1.371 (4)	C10—H10	0.9500
C20—C21	1.384 (4)	C17—H17	0.9500
C15—H15	0.9500	C5—H5	0.9500
C15—C16	1.388 (4)	C29—H29	0.9500
C7—H7	0.9500	C29—C30	1.385 (4)
C7—C2	1.397 (4)	C25—H25	0.9500
C7—C6	1.391 (4)	C25—C24	1.390 (4)
C27—H27	0.9500	C24—H24	0.9500
C27—C28	1.395 (4)	C24—C23	1.371 (5)
C13—H13	0.9500	C21—H21	0.9500
C13—C12	1.385 (4)	C21—C22	1.391 (4)
C2—C3	1.389 (4)	C23—H23	0.9500
C19—H19	0.9500	C23—C22	1.374 (5)
C19—C18	1.390 (4)	C30—H30	0.9500
C6—H6	0.9500	C22—H22	0.9500

O2—Rh1—As	171.06 (5)	C29—C28—H28	119.8
O1—Rh1—As	91.66 (5)	C8—C9—H9	120.6
O1—Rh1—O2	79.53 (7)	C8—C9—C10	118.8 (2)
C02—Rh1—As	89.53 (8)	C10—C9—H9	120.6
C02—Rh1—O2	99.31 (9)	C2—C3—H3	119.9
C02—Rh1—O1	178.39 (10)	C4—C3—C2	120.2 (3)
C26—As—Rh1	118.78 (7)	C4—C3—H3	119.9
C26—As—C20	103.15 (10)	C19—C18—H18	120.1
C14—As—Rh1	112.68 (7)	C17—C18—C19	119.7 (3)
C14—As—C26	104.81 (11)	C17—C18—H18	120.1
C14—As—C20	100.97 (11)	C12—C11—H11	119.7
C20—As—Rh1	114.44 (8)	C10—C11—H11	119.7
C1—O2—Rh1	111.54 (15)	C10—C11—C12	120.6 (3)
N1—O1—Rh1	110.33 (13)	C26—C31—H31	119.9
O1—N1—C8	114.38 (19)	C30—C31—C26	120.3 (3)
C1—N1—O1	119.1 (2)	C30—C31—H31	119.9
C1—N1—C8	126.2 (2)	C13—C12—C11	119.9 (3)
O2—C1—N1	119.3 (2)	C13—C12—H12	120.0
O2—C1—C2	117.1 (2)	C11—C12—H12	120.0
N1—C1—C2	123.5 (2)	C15—C16—H16	120.1
C27—C26—As	122.12 (19)	C17—C16—C15	119.8 (3)
C27—C26—C31	119.6 (2)	C17—C16—H16	120.1
C31—C26—As	118.27 (19)	C3—C4—H4	119.9
C13—C8—N1	118.2 (2)	C3—C4—C5	120.2 (3)
C9—C8—N1	120.5 (2)	C5—C4—H4	119.9
C9—C8—C13	121.3 (2)	C9—C10—H10	119.9
C15—C14—As	121.74 (19)	C11—C10—C9	120.1 (3)
C19—C14—As	118.28 (19)	C11—C10—H10	119.9
C19—C14—C15	119.9 (2)	C18—C17—H17	119.6
C25—C20—As	118.6 (2)	C16—C17—C18	120.7 (3)
C25—C20—C21	118.7 (3)	C16—C17—H17	119.6
C21—C20—As	122.7 (2)	C6—C5—C4	119.7 (2)
C14—C15—H15	120.1	C6—C5—H5	120.1
C16—C15—C14	119.9 (2)	C4—C5—H5	120.1
C16—C15—H15	120.1	C28—C29—H29	120.0
C2—C7—H7	120.2	C28—C29—C30	120.1 (3)
C6—C7—H7	120.2	C30—C29—H29	120.0
C6—C7—C2	119.5 (2)	C20—C25—H25	119.5
C26—C27—H27	120.2	C20—C25—C24	121.0 (3)
C26—C27—C28	119.7 (3)	C24—C25—H25	119.5
C28—C27—H27	120.2	C25—C24—H24	120.0
C8—C13—H13	120.4	C23—C24—C25	120.0 (3)
C12—C13—C8	119.1 (3)	C23—C24—H24	120.0
C12—C13—H13	120.4	C20—C21—H21	119.9
C7—C2—C1	123.2 (2)	C20—C21—C22	120.3 (3)
C3—C2—C1	117.0 (2)	C22—C21—H21	119.9
C3—C2—C7	119.7 (2)	C24—C23—H23	120.3
C14—C19—H19	120.1	C24—C23—C22	119.5 (3)
C18—C19—C14	119.8 (2)	C22—C23—H23	120.3
C18—C19—H19	120.1	C31—C30—C29	120.0 (3)
O02—C02—Rh1	178.5 (2)	C31—C30—H30	120.0
C7—C6—H6	119.7	C29—C30—H30	120.0
C5—C6—C7	120.7 (3)	C21—C22—H22	119.8
C5—C6—H6	119.7	C23—C22—C21	120.3 (3)
C27—C28—H28	119.8	C23—C22—H22	119.8
C29—C28—C27	120.4 (3)

Rh1—O2—C1—N1	4.4 (3)	C8—C9—C10—C11	1.5 (4)
Rh1—O2—C1—C2	−177.62 (16)	C14—C15—C16—C17	−0.4 (4)
Rh1—O1—N1—C1	1.5 (3)	C14—C19—C18—C17	−0.2 (4)
Rh1—O1—N1—C8	175.94 (16)	C20—C25—C24—C23	−1.8 (6)
As—C26—C27—C28	−178.1 (2)	C20—C21—C22—C23	−1.2 (5)
As—C26—C31—C30	179.1 (2)	C15—C14—C19—C18	−1.6 (4)
As—C14—C15—C16	−175.2 (2)	C15—C16—C17—C18	−1.4 (4)
As—C14—C19—C18	175.6 (2)	C7—C2—C3—C4	0.4 (4)
As—C20—C25—C24	−176.8 (3)	C7—C6—C5—C4	−0.1 (4)
As—C20—C21—C22	178.4 (3)	C27—C26—C31—C30	1.4 (4)
O2—C1—C2—C7	137.2 (2)	C27—C28—C29—C30	0.6 (5)
O2—C1—C2—C3	−39.0 (3)	C13—C8—C9—C10	−4.1 (4)
O1—N1—C1—O2	−4.1 (3)	C2—C7—C6—C5	−0.8 (4)
O1—N1—C1—C2	178.1 (2)	C2—C3—C4—C5	−1.3 (4)
O1—N1—C8—C13	−58.9 (3)	C19—C14—C15—C16	1.9 (4)
O1—N1—C8—C9	121.5 (2)	C19—C18—C17—C16	1.7 (4)
N1—C1—C2—C7	−45.0 (4)	C6—C7—C2—C1	−175.5 (2)
N1—C1—C2—C3	138.8 (3)	C6—C7—C2—C3	0.6 (4)
N1—C8—C13—C12	−175.6 (2)	C28—C29—C30—C31	0.3 (5)
N1—C8—C9—C10	175.5 (2)	C9—C8—C13—C12	4.0 (4)
C1—N1—C8—C13	115.1 (3)	C3—C4—C5—C6	1.1 (4)
C1—N1—C8—C9	−64.5 (3)	C31—C26—C27—C28	−0.5 (4)
C1—C2—C3—C4	176.7 (2)	C12—C11—C10—C9	1.2 (4)
C26—C27—C28—C29	−0.5 (4)	C10—C11—C12—C13	−1.3 (4)
C26—C31—C30—C29	−1.3 (5)	C25—C20—C21—C22	−3.2 (5)
C8—N1—C1—O2	−177.9 (2)	C25—C24—C23—C22	−2.7 (5)
C8—N1—C1—C2	4.3 (4)	C24—C23—C22—C21	4.2 (5)
C8—C13—C12—C11	−1.3 (4)	C21—C20—C25—C24	4.7 (5)

Acknowledgements

The University of the Free State and the South African National Research Fund are acknowledged for funding.

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