Aqua­bis­(4-methyl­benzene­sulfonato-κO)(η5-penta­methyl­cyclo­penta­dien­yl)rhodium(III) monohydrate

Roy, C.P.; Boyer, P.M.; Merola, J.S.

doi:10.1107/S160053681300860X

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Pages m259-m260

https://doi.org/10.1107/S160053681300860X

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Aquabis(4-methylbenzenesulfonato-κO)(η⁵-pentamethylcyclopentadienyl)rhodium(III) monohydrate

Christopher P. Roy,^a Pauline M. Boyer ^a and Joseph S. Merola ^a ^*

^aDepartment of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA
^*Correspondence e-mail: jmerola@vt.edu

(Received 18 March 2013; accepted 28 March 2013; online 13 April 2013)

The title half-sandwich rhodium(III) complex, [Rh(C₁₀H₁₅)(C₇H₇O₃S)₂(H₂O)]·H₂O, consists of a π-bonded pentamethylcyclopentadienyl group, two σ-bonded tosylate groups and an aqua ligand. The structure displays both inter- and intramolecular O—H⋯O hydrogen bonding. The intermolecular hydrogen bonding results in an extended helical chain along a 2₁ screw axis parallel to c, due to hydrogen bonding from the coordinating water ligand to the lattice water molecule and then to a sulfonate O atom of a different asymmetric unit.

Related literature

Synthesis details are given in Boyer et al. (1996 ). For the structure of another pentamethylcyclopentadienylmetal bis-tosylate (CCDC: 821138), see: Zaitsev et al. (2008 ). For the characterization of other aquo compounds, see: Bergmeister et al. (1990 ; CCDC: 601561) and Luo et al. (1990 ; CCDC: 595047). A survey of the geometry and environment of water molecules in crystalline hydrates studied by neutron diffraction can be found in in Ferraris & Franchini-Angela (1972 ).

Experimental

Crystal data

[Rh(C₁₀H₁₅)(C₇H₇O₃S)₂(H₂O)]·H₂O
M_r = 616.53
Orthorhombic, P b c n
a = 23.550 (8) Å
b = 18.814 (7) Å
c = 12.114 (5) Å
V = 5367 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.84 mm⁻¹
T = 295 K
0.4 × 0.4 × 0.4 mm

Data collection

Siemens P4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.00, T_max = 0.881
4738 measured reflections
4738 independent reflections
3297 reflections with I > 2σ(I)
3 standard reflections every 200 reflections intensity decay: 0(1)

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.086
S = 1.03
4738 reflections
340 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7A⋯O8	0.85 (5)	1.99 (6)	2.608 (6)	128 (5)
O7—H7B⋯O3	1.11 (8)	1.64 (8)	2.647 (5)	147 (7)
O8—H8D⋯O2ⁱ	0.77 (8)	2.06 (8)	2.807 (6)	162 (8)
O8—H8E⋯O5	0.88 (6)	1.91 (6)	2.766 (7)	162 (6)
Symmetry code: (i) $[-x+{\script{3\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: XSCANS (Siemens, 1994 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681300860X/pk2474sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681300860X/pk2474Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681300860X/pk2474Isup3.cdx

checkCIF report

Comment top

The title compound adds to the body of organometallic compounds with water as a ligand. The empirically discovered requirement that water attached to metals must also be hydrogen-bonded either intermolecularly or intramolecularly still holds with this complex where the bonded water is H-bonded both intramolecularly to a sulfate oxygen and intermolecularly to a lattice water molecule. The hydrogen bonding creates a helical motif that runs parallel to the c-axis.

Related literature top

Synthesis details are given in Boyer et al. (1996). For the structure of another pentamethylcyclopentadienylmetal bis-tosylate (CCDC: 821138), see: Zaitsev et al. (2008). For the characterization of other aquo compounds, see: Bergmeister et al. (1990; CCDC: 601561) and Luo et al. (1990; CCDC: 595047). A detailed analysis of the neutron diffaction of various mineral water structures can be found in Ferraris & Franchini-Angela (1972).

Experimental top

The title compound was prepared in a manner analogous to our previously reported carboxylate compounds using [(C₅Me₅)RhCl₂]₂ and silver tosylate. (Boyer et al., 1996).

Structure description top

Synthesis details are given in Boyer et al. (1996). For the structure of another pentamethylcyclopentadienylmetal bis-tosylate (CCDC: 821138), see: Zaitsev et al. (2008). For the characterization of other aquo compounds, see: Bergmeister et al. (1990; CCDC: 601561) and Luo et al. (1990; CCDC: 595047). A detailed analysis of the neutron diffaction of various mineral water structures can be found in Ferraris & Franchini-Angela (1972).

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: XSCANS (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. An ellipsoid plot (30% probability) view of the title compound.
	Fig. 2. A view of the hydrogen-bonded helical chain that propagates parallel to the c-axis.

Aquabis(4-methylbenzenesulfonato-κO)(η⁵-pentamethylcyclopentadienyl)rhodium(III) monohydrate top

Crystal data top

[Rh(C₁₀H₁₅)(C₇H₇O₃S)₂(H₂O)]·H₂O	D_x = 1.526 Mg m⁻³
M_r = 616.53	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 50 reflections
a = 23.550 (8) Å	θ = 2–25°
b = 18.814 (7) Å	µ = 0.84 mm⁻¹
c = 12.114 (5) Å	T = 295 K
V = 5367 (3) Å³	Prism, clear orange
Z = 8	0.4 × 0.4 × 0.4 mm
F(000) = 2544

Data collection top

Siemens P4 diffractometer	3297 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.0°, θ_min = 2.2°
profile data from θ/2θ scans	h = 0→28
Absorption correction: ψ scan (North et al., 1968)	k = −22→0
T_min = 0.00, T_max = 0.881	l = 0→14
4738 measured reflections	3 standard reflections every 200 reflections
4738 independent reflections	intensity decay: 0(1)

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0322P)² + 3.4175P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4738 reflections	Δρ_max = 0.38 e Å⁻³
340 parameters	Δρ_min = −0.29 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00052 (6)

Crystal data top

[Rh(C₁₀H₁₅)(C₇H₇O₃S)₂(H₂O)]·H₂O	V = 5367 (3) Å³
M_r = 616.53	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 23.550 (8) Å	µ = 0.84 mm⁻¹
b = 18.814 (7) Å	T = 295 K
c = 12.114 (5) Å	0.4 × 0.4 × 0.4 mm

Data collection top

Siemens P4 diffractometer	3297 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.00, T_max = 0.881	3 standard reflections every 200 reflections
4738 measured reflections	intensity decay: 0(1)
4738 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.38 e Å⁻³
4738 reflections	Δρ_min = −0.29 e Å⁻³
340 parameters

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

	x	y	z	U_iso*/U_eq
Rh1	0.666388 (12)	0.645607 (15)	0.50870 (2)	0.03433 (11)
S1	0.65268 (5)	0.82532 (6)	0.52292 (9)	0.0465 (3)
S2	0.62414 (6)	0.60927 (6)	0.25074 (9)	0.0538 (3)
O1	0.62955 (11)	0.75207 (14)	0.5237 (2)	0.0451 (7)
O2	0.63499 (15)	0.86471 (18)	0.6196 (3)	0.0677 (10)
O3	0.71402 (13)	0.82661 (17)	0.5072 (3)	0.0635 (9)
O4	0.63324 (16)	0.65843 (16)	0.3441 (2)	0.0660 (10)
O5	0.67723 (16)	0.57892 (19)	0.2134 (3)	0.0802 (11)
O6	0.58036 (17)	0.55830 (19)	0.2723 (3)	0.0822 (11)
O7	0.74332 (15)	0.6962 (2)	0.4484 (3)	0.0604 (9)
H7A	0.736 (2)	0.681 (3)	0.384 (5)	0.09 (2)*
H7B	0.730 (3)	0.753 (4)	0.442 (6)	0.17 (3)*
O8	0.7836 (2)	0.6195 (3)	0.2870 (4)	0.0896 (15)
H8D	0.802 (3)	0.632 (4)	0.238 (6)	0.13 (3)*
H8E	0.754 (3)	0.602 (3)	0.252 (5)	0.09 (2)*
C1	0.6733 (2)	0.5351 (2)	0.5370 (3)	0.0510 (12)
C2	0.71567 (19)	0.5703 (2)	0.5983 (4)	0.0505 (11)
C3	0.68878 (19)	0.6193 (2)	0.6720 (3)	0.0470 (11)
C4	0.62904 (18)	0.6102 (2)	0.6596 (3)	0.0482 (11)
C5	0.6187 (2)	0.5592 (2)	0.5754 (4)	0.0512 (12)
C6	0.6836 (3)	0.4784 (3)	0.4526 (4)	0.097 (2)
H6A	0.7128	0.4937	0.4027	0.146*
H6B	0.6493	0.4697	0.4122	0.146*
H6C	0.6954	0.4355	0.4889	0.146*
C7	0.7786 (2)	0.5599 (4)	0.5867 (5)	0.097 (2)
H7C	0.7981	0.6007	0.6154	0.145*
H7D	0.7879	0.5539	0.5101	0.145*
H7E	0.7899	0.5183	0.6271	0.145*
C8	0.7184 (3)	0.6679 (3)	0.7509 (4)	0.0870 (19)
H8A	0.7038	0.7153	0.7424	0.130*
H8B	0.7584	0.6677	0.7358	0.130*
H8C	0.7119	0.6520	0.8251	0.130*
C9	0.5840 (3)	0.6498 (3)	0.7230 (5)	0.098 (2)
H9A	0.5486	0.6468	0.6841	0.147*
H9B	0.5950	0.6987	0.7303	0.147*
H9C	0.5799	0.6290	0.7949	0.147*
C10	0.5612 (2)	0.5339 (3)	0.5388 (5)	0.091 (2)
H10A	0.5641	0.5131	0.4666	0.136*
H10B	0.5354	0.5733	0.5366	0.136*
H10C	0.5474	0.4989	0.5899	0.136*
C11	0.62207 (17)	0.8673 (2)	0.4062 (3)	0.0427 (10)
C12	0.6297 (2)	0.9397 (2)	0.3923 (4)	0.0576 (12)
H12	0.6498	0.9656	0.4446	0.069*
C13	0.6074 (2)	0.9732 (3)	0.3013 (4)	0.0639 (14)
H13	0.6128	1.0219	0.2931	0.077*
C14	0.5773 (2)	0.9366 (3)	0.2217 (4)	0.0554 (12)
C15	0.5711 (2)	0.8643 (2)	0.2361 (4)	0.0571 (12)
H15	0.5512	0.8383	0.1834	0.068*
C16	0.59347 (19)	0.8292 (2)	0.3267 (4)	0.0510 (11)
H16	0.5892	0.7802	0.3338	0.061*
C17	0.5522 (2)	0.9735 (3)	0.1226 (4)	0.0834 (18)
H17A	0.5754	0.9641	0.0589	0.125*
H17B	0.5509	1.0238	0.1358	0.125*
H17C	0.5145	0.9561	0.1098	0.125*
C18	0.59902 (19)	0.6660 (2)	0.1437 (3)	0.0475 (11)
C19	0.63637 (19)	0.7094 (3)	0.0871 (4)	0.0543 (12)
H19	0.6749	0.7080	0.1035	0.065*
C20	0.6164 (2)	0.7548 (3)	0.0061 (4)	0.0591 (12)
H20	0.6419	0.7834	−0.0323	0.071*
C21	0.5590 (2)	0.7586 (3)	−0.0189 (4)	0.0584 (12)
C22	0.5227 (2)	0.7139 (3)	0.0370 (4)	0.0575 (13)
H22	0.4842	0.7148	0.0200	0.069*
C23	0.54202 (19)	0.6675 (2)	0.1184 (3)	0.0519 (12)
H23	0.5167	0.6379	0.1553	0.062*
C24	0.5368 (3)	0.8104 (3)	−0.1051 (4)	0.0871 (19)
H24A	0.5559	0.8024	−0.1739	0.131*
H24B	0.5437	0.8583	−0.0809	0.131*
H24C	0.4967	0.8034	−0.1147	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Rh1	0.03743 (17)	0.03487 (17)	0.03068 (16)	0.00144 (14)	−0.00110 (14)	0.00030 (14)
S1	0.0509 (6)	0.0401 (5)	0.0485 (6)	0.0032 (5)	−0.0098 (5)	−0.0090 (5)
S2	0.0766 (8)	0.0486 (7)	0.0362 (6)	0.0044 (6)	−0.0117 (6)	−0.0066 (5)
O1	0.0436 (16)	0.0396 (16)	0.0522 (17)	0.0031 (12)	−0.0028 (13)	0.0010 (13)
O2	0.092 (3)	0.060 (2)	0.0503 (18)	0.0172 (19)	−0.0182 (18)	−0.0173 (16)
O3	0.0477 (17)	0.0533 (18)	0.090 (2)	−0.0023 (15)	−0.0137 (18)	−0.0075 (19)
O4	0.113 (3)	0.049 (2)	0.0358 (16)	0.0138 (19)	−0.0241 (17)	−0.0100 (14)
O5	0.097 (3)	0.080 (3)	0.064 (2)	0.035 (2)	−0.008 (2)	−0.0091 (19)
O6	0.118 (3)	0.070 (2)	0.059 (2)	−0.027 (2)	−0.018 (2)	0.0126 (18)
O7	0.054 (2)	0.055 (2)	0.072 (2)	−0.0047 (17)	0.0159 (19)	0.0070 (19)
O8	0.087 (3)	0.119 (4)	0.063 (3)	0.008 (3)	0.025 (3)	−0.002 (3)
C1	0.084 (4)	0.029 (2)	0.040 (2)	0.010 (2)	−0.006 (2)	0.0060 (17)
C2	0.051 (3)	0.054 (3)	0.047 (2)	0.009 (2)	−0.007 (2)	0.015 (2)
C3	0.058 (3)	0.049 (3)	0.034 (2)	−0.010 (2)	−0.007 (2)	0.0047 (19)
C4	0.051 (3)	0.053 (3)	0.040 (2)	0.004 (2)	0.014 (2)	0.014 (2)
C5	0.055 (3)	0.052 (3)	0.047 (3)	−0.015 (2)	−0.011 (2)	0.017 (2)
C6	0.184 (7)	0.049 (3)	0.058 (3)	0.022 (4)	−0.008 (4)	−0.006 (3)
C7	0.059 (4)	0.129 (6)	0.102 (5)	0.037 (4)	0.003 (3)	0.030 (4)
C8	0.126 (5)	0.081 (4)	0.054 (3)	−0.043 (4)	−0.034 (3)	0.008 (3)
C9	0.103 (5)	0.116 (5)	0.075 (4)	0.048 (4)	0.046 (4)	0.023 (4)
C10	0.080 (4)	0.096 (4)	0.097 (4)	−0.043 (3)	−0.039 (3)	0.044 (4)
C11	0.043 (2)	0.036 (2)	0.049 (2)	−0.0010 (19)	0.0031 (19)	−0.0045 (19)
C12	0.062 (3)	0.047 (3)	0.064 (3)	−0.008 (2)	−0.006 (2)	−0.010 (2)
C13	0.074 (4)	0.043 (3)	0.074 (3)	−0.002 (3)	0.007 (3)	0.014 (3)
C14	0.051 (3)	0.065 (3)	0.050 (3)	0.002 (3)	0.008 (2)	0.011 (2)
C15	0.066 (3)	0.057 (3)	0.049 (3)	0.001 (2)	−0.011 (2)	−0.003 (2)
C16	0.063 (3)	0.034 (2)	0.055 (3)	−0.003 (2)	−0.010 (2)	−0.008 (2)
C17	0.086 (4)	0.091 (4)	0.073 (4)	−0.006 (3)	0.000 (3)	0.034 (3)
C18	0.059 (3)	0.054 (3)	0.029 (2)	0.002 (2)	−0.006 (2)	−0.0066 (19)
C19	0.045 (3)	0.070 (3)	0.047 (3)	−0.002 (2)	−0.006 (2)	−0.004 (2)
C20	0.065 (3)	0.069 (3)	0.043 (3)	−0.008 (2)	−0.002 (2)	0.004 (2)
C21	0.077 (3)	0.060 (3)	0.038 (2)	0.008 (3)	−0.008 (2)	−0.003 (2)
C22	0.052 (3)	0.073 (3)	0.047 (3)	0.009 (3)	−0.014 (2)	−0.015 (2)
C23	0.055 (3)	0.061 (3)	0.040 (2)	−0.007 (2)	−0.001 (2)	−0.008 (2)
C24	0.112 (5)	0.091 (4)	0.059 (3)	0.018 (4)	−0.021 (3)	0.010 (3)

Geometric parameters (Å, º) top

Rh1—O1	2.190 (3)	C8—H8B	0.9600
Rh1—O4	2.155 (3)	C8—H8C	0.9600
Rh1—O7	2.173 (3)	C9—H9A	0.9600
Rh1—C1	2.113 (4)	C9—H9B	0.9600
Rh1—C2	2.129 (4)	C9—H9C	0.9600
Rh1—C3	2.106 (4)	C10—H10A	0.9600
Rh1—C4	2.135 (4)	C10—H10B	0.9600
Rh1—C5	2.135 (4)	C10—H10C	0.9600
S1—O1	1.482 (3)	C11—C12	1.384 (6)
S1—O2	1.447 (3)	C11—C16	1.377 (6)
S1—O3	1.457 (3)	C12—H12	0.9300
S1—C11	1.773 (4)	C12—C13	1.373 (6)
S2—O4	1.476 (3)	C13—H13	0.9300
S2—O5	1.447 (4)	C13—C14	1.382 (6)
S2—O6	1.432 (4)	C14—C15	1.380 (6)
S2—C18	1.781 (4)	C14—C17	1.507 (6)
O7—H7A	0.85 (5)	C15—H15	0.9300
O7—H7B	1.11 (8)	C15—C16	1.386 (6)
O8—H8D	0.77 (8)	C16—H16	0.9300
O8—H8E	0.88 (6)	C17—H17A	0.9600
C1—C2	1.410 (6)	C17—H17B	0.9600
C1—C5	1.439 (6)	C17—H17C	0.9600
C1—C6	1.498 (6)	C18—C19	1.382 (6)
C2—C3	1.431 (6)	C18—C23	1.377 (6)
C2—C7	1.501 (6)	C19—H19	0.9300
C3—C4	1.425 (6)	C19—C20	1.384 (6)
C3—C8	1.495 (6)	C20—H20	0.9300
C4—C5	1.422 (6)	C20—C21	1.387 (7)
C4—C9	1.506 (6)	C21—C22	1.377 (7)
C5—C10	1.501 (6)	C21—C24	1.523 (6)
C6—H6A	0.9600	C22—H22	0.9300
C6—H6B	0.9600	C22—C23	1.394 (6)
C6—H6C	0.9600	C23—H23	0.9300
C7—H7C	0.9600	C24—H24A	0.9600
C7—H7D	0.9600	C24—H24B	0.9600
C7—H7E	0.9600	C24—H24C	0.9600
C8—H8A	0.9600

O4—Rh1—O1	80.25 (11)	C1—C6—H6B	109.5
O4—Rh1—O7	86.66 (15)	C1—C6—H6C	109.5
O7—Rh1—O1	87.57 (13)	H6A—C6—H6B	109.5
C1—Rh1—O1	156.42 (15)	H6A—C6—H6C	109.5
C1—Rh1—O4	106.75 (14)	H6B—C6—H6C	109.5
C1—Rh1—O7	114.93 (17)	C2—C7—H7C	109.5
C1—Rh1—C2	38.81 (17)	C2—C7—H7D	109.5
C1—Rh1—C4	65.50 (17)	C2—C7—H7E	109.5
C1—Rh1—C5	39.60 (17)	H7C—C7—H7D	109.5
C2—Rh1—O1	141.46 (15)	H7C—C7—H7E	109.5
C2—Rh1—O4	138.06 (15)	H7D—C7—H7E	109.5
C2—Rh1—O7	90.48 (16)	C3—C8—H8A	109.5
C2—Rh1—C4	65.18 (17)	C3—C8—H8B	109.5
C2—Rh1—C5	65.60 (17)	C3—C8—H8C	109.5
C3—Rh1—O1	103.66 (15)	H8A—C8—H8B	109.5
C3—Rh1—O4	170.43 (15)	H8A—C8—H8C	109.5
C3—Rh1—O7	102.12 (16)	H8B—C8—H8C	109.5
C3—Rh1—C1	66.24 (16)	C4—C9—H9A	109.5
C3—Rh1—C2	39.49 (16)	C4—C9—H9B	109.5
C3—Rh1—C4	39.27 (16)	C4—C9—H9C	109.5
C3—Rh1—C5	66.26 (16)	H9A—C9—H9B	109.5
C4—Rh1—O1	92.95 (14)	H9A—C9—H9C	109.5
C4—Rh1—O4	132.68 (17)	H9B—C9—H9C	109.5
C4—Rh1—O7	140.18 (17)	C5—C10—H10A	109.5
C4—Rh1—C5	38.89 (17)	C5—C10—H10B	109.5
C5—Rh1—O1	117.19 (16)	C5—C10—H10C	109.5
C5—Rh1—O4	104.17 (15)	H10A—C10—H10B	109.5
C5—Rh1—O7	154.07 (17)	H10A—C10—H10C	109.5
O1—S1—C11	105.65 (18)	H10B—C10—H10C	109.5
O2—S1—O1	111.4 (2)	C12—C11—S1	118.9 (3)
O2—S1—O3	112.5 (2)	C16—C11—S1	121.6 (3)
O2—S1—C11	107.48 (19)	C16—C11—C12	119.4 (4)
O3—S1—O1	112.37 (17)	C11—C12—H12	120.0
O3—S1—C11	107.0 (2)	C13—C12—C11	120.0 (4)
O4—S2—C18	103.32 (18)	C13—C12—H12	120.0
O5—S2—O4	111.2 (2)	C12—C13—H13	119.1
O5—S2—C18	107.2 (2)	C12—C13—C14	121.8 (4)
O6—S2—O4	112.6 (2)	C14—C13—H13	119.1
O6—S2—O5	114.5 (2)	C13—C14—C17	121.9 (5)
O6—S2—C18	107.1 (2)	C15—C14—C13	117.2 (4)
S1—O1—Rh1	134.78 (17)	C15—C14—C17	120.9 (5)
S2—O4—Rh1	133.72 (19)	C14—C15—H15	119.0
Rh1—O7—H7A	89 (4)	C14—C15—C16	122.0 (4)
Rh1—O7—H7B	102 (4)	C16—C15—H15	119.0
H7A—O7—H7B	102 (5)	C11—C16—C15	119.5 (4)
H8D—O8—H8E	101 (6)	C11—C16—H16	120.3
C2—C1—Rh1	71.2 (2)	C15—C16—H16	120.3
C2—C1—C5	108.4 (4)	C14—C17—H17A	109.5
C2—C1—C6	125.4 (5)	C14—C17—H17B	109.5
C5—C1—Rh1	71.0 (2)	C14—C17—H17C	109.5
C5—C1—C6	126.1 (5)	H17A—C17—H17B	109.5
C6—C1—Rh1	127.0 (3)	H17A—C17—H17C	109.5
C1—C2—Rh1	70.0 (2)	H17B—C17—H17C	109.5
C1—C2—C3	108.5 (4)	C19—C18—S2	120.2 (3)
C1—C2—C7	126.0 (5)	C23—C18—S2	119.9 (4)
C3—C2—Rh1	69.4 (2)	C23—C18—C19	119.9 (4)
C3—C2—C7	125.4 (5)	C18—C19—H19	120.0
C7—C2—Rh1	125.3 (3)	C18—C19—C20	120.0 (4)
C2—C3—Rh1	71.1 (2)	C20—C19—H19	120.0
C2—C3—C8	125.9 (5)	C19—C20—H20	119.4
C4—C3—Rh1	71.5 (2)	C19—C20—C21	121.1 (5)
C4—C3—C2	107.1 (4)	C21—C20—H20	119.4
C4—C3—C8	127.0 (5)	C20—C21—C24	121.2 (5)
C8—C3—Rh1	125.0 (3)	C22—C21—C20	117.9 (4)
C3—C4—Rh1	69.3 (2)	C22—C21—C24	120.9 (5)
C3—C4—C9	125.5 (5)	C21—C22—H22	119.1
C5—C4—Rh1	70.6 (2)	C21—C22—C23	121.8 (4)
C5—C4—C3	109.0 (4)	C23—C22—H22	119.1
C5—C4—C9	125.4 (5)	C18—C23—C22	119.2 (4)
C9—C4—Rh1	124.9 (3)	C18—C23—H23	120.4
C1—C5—Rh1	69.4 (2)	C22—C23—H23	120.4
C1—C5—C10	127.6 (5)	C21—C24—H24A	109.5
C4—C5—Rh1	70.6 (2)	C21—C24—H24B	109.5
C4—C5—C1	106.9 (4)	C21—C24—H24C	109.5
C4—C5—C10	125.5 (5)	H24A—C24—H24B	109.5
C10—C5—Rh1	127.2 (3)	H24A—C24—H24C	109.5
C1—C6—H6A	109.5	H24B—C24—H24C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O8	0.85 (5)	1.99 (6)	2.608 (6)	128 (5)
O7—H7B···O3	1.11 (8)	1.64 (8)	2.647 (5)	147 (7)
O8—H8D···O2ⁱ	0.77 (8)	2.06 (8)	2.807 (6)	162 (8)
O8—H8E···O5	0.88 (6)	1.91 (6)	2.766 (7)	162 (6)

Symmetry code: (i) −x+3/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Rh(C₁₀H₁₅)(C₇H₇O₃S)₂(H₂O)]·H₂O
M_r	616.53
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	295
a, b, c (Å)	23.550 (8), 18.814 (7), 12.114 (5)
V (Å³)	5367 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.84
Crystal size (mm)	0.4 × 0.4 × 0.4

Data collection
Diffractometer	Siemens P4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.00, 0.881
No. of measured, independent and observed [I > 2σ(I)] reflections	4738, 4738, 3297
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.086, 1.03
No. of reflections	4738
No. of parameters	340
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.29

Computer programs: XSCANS (Siemens, 1994), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O8	0.85 (5)	1.99 (6)	2.608 (6)	128 (5)
O7—H7B···O3	1.11 (8)	1.64 (8)	2.647 (5)	147 (7)
O8—H8D···O2ⁱ	0.77 (8)	2.06 (8)	2.807 (6)	162 (8)
O8—H8E···O5	0.88 (6)	1.91 (6)	2.766 (7)	162 (6)

Symmetry code: (i) −x+3/2, −y+3/2, z−1/2.

Acknowledgements

We acknowledge the financial support of the NSF (CHE 9214027) and ACS–PRF (23961-ACl). PMB acknowledges an ACS–PRF undergraduate summer fellowship. Funds for the purchase of the diffractometer used in this work were provided by the Commonwealth of Virginia.

References

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