Ethyl­tri­phenyl­phospho­nium perrhenate and (iodo­methyl)­tri­phenyl­phospho­nium perrhenate

Ethyl­tri­phenyl­phospho­nium perrhenate, (C₂₀H₂₀P)[ReO₄], and (iodo­methyl)­tri­phenyl­phospho­nium perrhenate, (C₁₉H₁₇IP)[ReO₄], have been crystallized from 2-propanol. Both crystal structures consist of phospho­nium cations and perrhenate anions. The cations show the typical propeller-like geometry. In both crystals, the positions of the nearly tetrahedral anions are stabilized by weak C—H...O hydrogen bonds, and for the latter compound, I...π interactions also occur.

S1. Comment

In studies of the interaction of gaseous HCl with [ReO₄]⁻ ions, Yatirajam & Harjinder (1975) and Lis & Jeżowska-Trzebiatowska (1977) used tetraphenylphosphonium and tetraphenylarsonium perrhenates suspended in various solvents. The highly symmetric cations possessing 4 symmetry present in these perrhenates seem to be one of the reasons for the disorder observed in the oxochlororhenate(VI).

Our current focus on perrhenates uses less-symmetrical cations containing the triphenylphosphonium moiety as starting materials for the synthesis of rhenium(VI) compounds. We report here the preparation and crystallization of two such salts, (I) and (II), with ethyltriphenylphosphonium and (iodomethyl)triphenylphosphonium cations, respectively. \sch

Both crystal structures consist of phosphonium cations and nearly tetrahedral perrhenate anions (Fig. 1). Apart from the three planar phenyl rings, the P atoms are bonded to methylene groups, which are further bonded to a methyl group in the case of (I) and to an I atom in case of (II). The triphenylphosphonium moieties show similar propeller-like geometries. However, the positions of the methyl group in (I) and the I atom in (II) relative to the phenyl rings are different.

The crystal structure of (I) contains ethyltriphenylphosphonium cations and perrhenate anions, both lying in general positions. The P atom is bonded to one ethyl group and three phenyl groups to form the cation, with the usual propeller-like symmetry (Table 1). The methyl group is in a trans position with respect to one of the phenyl groups. As expected (Broder et al., 2002), the environment of the P atom is nearly tetrahedral. The P atom deviates from the planes of the phenyl rings, with a maximum distance of 0.138 (3) Å from the plane of the C11—C61 ring.

In published structures containing ethyltriphenylphosphonium cations (Broder et al., 2002; Caira et al., 1978; Bélanger & Beauchamp, 1993; Fedin et al., 1990; Janickis et al., 2002; Ansari et al., 1990; Lamb & Mason, 2002), two possible cation geometries have been observed. The criterion is the deviation of the ethyl group from the plane defined by the phenyl ring trans to the methyl group. In (I), this deviation is significant, at −0.879 (6) and −0.551 (5) Å for the methyl and the methylene groups, respectively.

In the crystal structure of (I), the cations form tapes along [001]. This pattern is stabilized by weak C—H···O hydrogen bonds involving H atoms from the phenyl rings and the methylene moiety (Table 2). The positions of the interacting perrhenate anions are stabilized in channels between the tapes. For each perrhenate anion, atoms O1 and O2 participate in one hydrogen bond, and atom O4 in two hydrogen bonds. In each cation tape, there are no stacking interactions between the phenyl rings.

The crystal structure of (II) consists of (iodomethyl)triphenylphosphonium cations and perrhenate anions lying in general positions. The P atom is bonded to one iodomethyl group and to three phenyl groups, forming a cation with the usual (Scherfize et al., 1985; Vogt et al., 1993; Jin et al., 1995) propeller-like symmetry (Table 3). The I atom is in a trans position with respect to one of the phenyl rings and nearly gauche with respect to the other two.

It is interesting to note that the I atom in (II) is not involved in any hydrogen bonds. However, it participates in I···π interactions with the C41—C51 edge of the C11—C61 phenyl ring of the molecule at (x − 1/2, 1/2 − y, z − 1/2), with I···C51 and I···C41 distances of 3.509 (4) and 3.553 (4) Å, respectively. Thus chains of interacting cations are formed, running parallel to the [101] direction (Fig. 3). Similar interactions were observed in one of the previously reported structures with (iodomethyl)triphenylphosphonium cations (Scherfize et al., 1985; Vogt et al., 1993; Jin et al., 1995 Which one of these references applies here?), the relevant I···C distances being approximately 3.7 and 3.4 Å.

The positions of the perrhenate anions between the cation chains in (II) are stabilized by weak C—H···O hydrogen bonds with parameters within the range proposed by Desiraju & Steiner (1999). There are more such stabilizing interactions than in the structure of (I). The environment of each cation consists of the anions at (1/2 + x, 1/2 − y, z − 1/2), (1/2 − x, 1/2 − y, z + 1/2) and (1 − x, −y, 1 − z).

S2. Experimental

The title compounds were prepared by reaction of the relevant phosphonium chlorides with ammonium perrhenate in stoichiometric molar ratio in aqueous solution at room temperature. In each case, a fine white precipitate was obtained immediately, which was then filtered on a medium-density filter and washed with small portions of distilled water until no chloride anions were detected in the filtrate. Crystals of (I) and (II) were obtained by recrystallization of the crude product from solution in 2-propanol at room temperature.

S3. Refinement

H atoms wre treated as riding atoms, with C—H distances in the range 0.95–0.99 Å, and with U_iso(H) = 1.2U_eq(C), or 1.5U_eq(C) for the methyl group.

Computing details

For both compounds, data collection: Please provide missing details; cell refinement: Please provide missing details; data reduction: Please provide missing details; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Please provide missing details; software used to prepare material for publication: Please provide missing details.

Figures

	Fig. 1. A perspective view of the asymmetric unit of (a) (I) and (b) (II), showing the atom-labelling schemes. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of the cation tapes formed along [001] in the structure of (I). [Symmetry codes: (i) 3/2 − x, 1 − y, z − 1/2; (iii) 3/2 − x, 1 − y, 1/2 + z; (iv) 1 + x, y, z; (v) 1/2 − x, 1 − y, 1/2 + z.] Symmetry codes have been renumbered - please check carefully.
	Fig. 3. A view of one of the cation chains formed in the crystal structure of (II). H atoms have been omitted for clarity. Cg denotes the centroid of the C41—C51 bond. [Symmetry codes: (vi) x − 1/2, 1/2 − y, z − 1/2; (vii) x − 1, y, z − 1.] Symmetry codes have been renumbered - please check carefully.

(I)

Crystal data

(C20H20)[ReO4]	F(000) = 1048
Mr = 541.53	Dx = 1.877 Mg m^−3 Dm = 1.85 Mg m^−3 Dm measured by flotation at 298 K in what solvent
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 20452 reflections
a = 9.924 (2) Å	θ = 3.5–35.0°
b = 13.345 (3) Å	µ = 6.45 mm^−1
c = 14.467 (3) Å	T = 100 K
V = 1915.9 (7) Å^3	Block, colourless
Z = 4	0.30 × 0.12 × 0.12 mm

Data collection

Kuma KM4 CCD area-detector diffractometer	8115 independent reflections
Radiation source: fine-focus sealed tube	7569 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
ω scans	θmax = 35.0°, θmin = 3.5°
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2003)	h = −15→9
Tmin = 0.274, Tmax = 0.512	k = −21→21
31016 measured reflections	l = −23→23

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.022	w = 1/[σ^2(Fo^2) + (0.017P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.040	(Δ/σ)max = 0.004
S = 1.02	Δρmax = 1.88 e Å^−3
8115 reflections	Δρmin = −1.44 e Å^−3
236 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00407 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with how many Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.019 (5)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Re	0.636008 (8)	0.466790 (6)	0.796752 (6)	0.01340 (2)
P	0.35449 (5)	0.52808 (4)	0.48396 (3)	0.00973 (8)
C1	0.5587 (3)	0.66537 (19)	0.5334 (2)	0.0218 (5)
H1A	0.6416	0.6744	0.5693	0.033*
H1B	0.4883	0.7096	0.5578	0.033*
H1C	0.5760	0.6819	0.4685	0.033*
C2	0.5122 (2)	0.55630 (17)	0.54072 (17)	0.0150 (4)
H2A	0.5036	0.5388	0.6070	0.018*
H2B	0.5831	0.5128	0.5141	0.018*
C11	0.3420 (2)	0.39426 (16)	0.47197 (14)	0.0117 (4)
C21	0.4090 (2)	0.33093 (17)	0.53491 (15)	0.0147 (4)
H21	0.4663	0.3585	0.5810	0.018*
C31	0.3908 (2)	0.22784 (16)	0.52923 (16)	0.0169 (4)
H31	0.4357	0.1847	0.5714	0.020*
C41	0.3065 (2)	0.18774 (17)	0.46162 (17)	0.0174 (4)
H41	0.2931	0.1173	0.4585	0.021*
C51	0.2420 (2)	0.25023 (17)	0.39881 (17)	0.0152 (4)
H51	0.1856	0.2223	0.3525	0.018*
C61	0.2597 (2)	0.35379 (17)	0.40344 (15)	0.0130 (4)
H61	0.2160	0.3964	0.3602	0.016*
C12	0.2134 (2)	0.57146 (17)	0.54988 (15)	0.0117 (4)
C22	0.2296 (2)	0.63209 (18)	0.62825 (16)	0.0162 (4)
H22	0.3173	0.6497	0.6489	0.019*
C32	0.1167 (3)	0.66630 (17)	0.67558 (15)	0.0188 (5)
H32	0.1274	0.7080	0.7283	0.023*
C42	−0.0121 (3)	0.63968 (18)	0.64591 (17)	0.0180 (5)
H42	−0.0889	0.6628	0.6788	0.022*
C52	−0.0286 (2)	0.57950 (18)	0.56856 (17)	0.0162 (4)
H52	−0.1166	0.5622	0.5483	0.019*
C62	0.0833 (2)	0.54447 (17)	0.52068 (14)	0.0139 (4)
H62	0.0719	0.5024	0.4683	0.017*
C13	0.3504 (2)	0.58309 (15)	0.37073 (14)	0.0117 (4)
C23	0.4608 (2)	0.56700 (17)	0.31235 (15)	0.0139 (4)
H23	0.5347	0.5273	0.3326	0.017*
C33	0.4616 (2)	0.60952 (17)	0.22447 (15)	0.0153 (4)
H33	0.5361	0.5986	0.1845	0.018*
C43	0.3536 (2)	0.66797 (16)	0.19504 (15)	0.0166 (4)
H43	0.3554	0.6976	0.1353	0.020*
C53	0.2437 (2)	0.68322 (18)	0.25237 (17)	0.0162 (4)
H53	0.1696	0.7222	0.2314	0.019*
C63	0.2415 (2)	0.64147 (17)	0.34068 (16)	0.0132 (4)
H63	0.1666	0.6526	0.3803	0.016*
O1	0.72776 (17)	0.48202 (14)	0.69626 (13)	0.0220 (4)
O2	0.49474 (17)	0.54243 (14)	0.79202 (14)	0.0247 (3)
O3	0.58690 (18)	0.34278 (13)	0.80558 (15)	0.0265 (4)
O4	0.73284 (19)	0.49978 (16)	0.89147 (14)	0.0278 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re	0.01094 (3)	0.01778 (4)	0.01148 (3)	0.00277 (3)	0.00138 (3)	−0.00072 (4)
P	0.0100 (2)	0.00982 (19)	0.00933 (18)	0.0006 (2)	−0.00109 (17)	−0.00005 (19)
C1	0.0198 (12)	0.0187 (11)	0.0268 (13)	−0.0048 (9)	−0.0046 (10)	−0.0012 (10)
C2	0.0132 (10)	0.0170 (11)	0.0148 (9)	0.0003 (8)	−0.0036 (8)	−0.0001 (8)
C11	0.0118 (10)	0.0119 (8)	0.0115 (8)	0.0017 (7)	0.0015 (7)	0.0008 (7)
C21	0.0147 (9)	0.0164 (10)	0.0130 (9)	0.0000 (8)	−0.0002 (8)	0.0004 (8)
C31	0.0210 (12)	0.0134 (9)	0.0162 (9)	0.0033 (8)	0.0019 (8)	0.0037 (8)
C41	0.0196 (11)	0.0126 (10)	0.0200 (11)	−0.0004 (8)	0.0068 (9)	−0.0013 (9)
C51	0.0148 (10)	0.0154 (9)	0.0154 (10)	−0.0022 (8)	0.0029 (8)	−0.0038 (8)
C61	0.0131 (9)	0.0138 (9)	0.0120 (9)	0.0014 (7)	−0.0001 (7)	−0.0009 (8)
C12	0.0141 (10)	0.0110 (9)	0.0100 (9)	0.0016 (7)	0.0010 (7)	0.0010 (7)
C22	0.0173 (10)	0.0177 (10)	0.0135 (10)	0.0021 (8)	−0.0028 (8)	−0.0027 (8)
C32	0.0242 (12)	0.0188 (10)	0.0135 (8)	0.0060 (9)	−0.0008 (8)	−0.0034 (8)
C42	0.0209 (11)	0.0172 (10)	0.0157 (10)	0.0070 (9)	0.0043 (9)	0.0007 (9)
C52	0.0147 (10)	0.0179 (11)	0.0159 (10)	0.0023 (8)	0.0030 (8)	0.0013 (9)
C62	0.0157 (9)	0.0143 (10)	0.0116 (8)	−0.0002 (8)	0.0014 (7)	−0.0019 (8)
C13	0.0130 (10)	0.0110 (8)	0.0111 (8)	−0.0015 (8)	−0.0014 (7)	−0.0006 (7)
C23	0.0109 (9)	0.0167 (9)	0.0140 (10)	0.0016 (7)	0.0011 (7)	−0.0010 (8)
C33	0.0157 (10)	0.0178 (10)	0.0124 (9)	−0.0024 (8)	0.0022 (7)	−0.0021 (8)
C43	0.0204 (10)	0.0187 (9)	0.0107 (8)	−0.0028 (8)	−0.0021 (9)	0.0011 (8)
C53	0.0159 (10)	0.0168 (10)	0.0158 (10)	0.0002 (8)	−0.0026 (8)	0.0031 (9)
C63	0.0124 (10)	0.0140 (10)	0.0132 (9)	−0.0009 (8)	0.0005 (8)	−0.0013 (8)
O1	0.0193 (7)	0.0297 (9)	0.0171 (8)	0.0039 (7)	0.0057 (7)	0.0007 (8)
O2	0.0202 (8)	0.0295 (9)	0.0244 (8)	0.0108 (7)	0.0044 (7)	0.0010 (10)
O3	0.0220 (8)	0.0219 (8)	0.0356 (10)	0.0005 (7)	0.0062 (9)	0.0029 (9)
O4	0.0231 (9)	0.0427 (11)	0.0175 (8)	0.0030 (8)	−0.0039 (7)	−0.0104 (8)

Geometric parameters (Å, º)

Re—O1	1.728 (2)	C23—C33	1.392 (3)
Re—O2	1.729 (2)	C33—C43	1.392 (3)
Re—O3	1.730 (2)	C43—C53	1.386 (3)
Re—O4	1.731 (2)	C53—C63	1.394 (3)
P—C11	1.799 (3)	C1—H1A	0.9800
P—C12	1.791 (3)	C1—H1B	0.9800
P—C13	1.796 (3)	C1—H1C	0.9800
P—C2	1.807 (2)	C2—H2A	0.9900
C1—C2	1.531 (3)	C2—H2B	0.9900
C11—C61	1.393 (3)	C21—H21	0.9500
C11—C21	1.409 (3)	C41—H41	0.9500
C21—C31	1.390 (3)	C51—H51	0.9500
C31—C41	1.394 (3)	C61—H61	0.9500
C41—C51	1.389 (3)	C22—H22	0.9500
C51—C61	1.395 (3)	C32—H32	0.9500
C12—C22	1.402 (3)	C42—H42	0.9500
C12—C62	1.405 (3)	C52—H52	0.9500
C22—C32	1.390 (3)	C62—H62	0.9500
C32—C42	1.395 (4)	C23—H23	0.9500
C42—C52	1.387 (3)	C33—H33	0.9500
C52—C62	1.390 (3)	C43—H43	0.9500
C13—C23	1.400 (3)	C53—H53	0.9500
C13—C63	1.401 (3)	C63—H63	0.9500
O1—Re—O2	109.0 (1)	C51—C41—C31	120.3 (2)
O1—Re—O3	108.9 (1)	C41—C51—C61	120.4 (2)
O2—Re—O3	109.4 (1)	C11—C61—C51	119.5 (2)
O1—Re—O4	110.1 (1)	C22—C12—C62	119.8 (2)
O2—Re—O4	109.5 (1)	C22—C12—P	121.8 (2)
O3—Re—O4	110.0 (1)	C62—C12—P	118.4 (2)
C12—P—C13	109.6 (1)	C32—C22—C12	119.7 (2)
C12—P—C11	108.6 (1)	C22—C32—C42	120.2 (2)
C13—P—C11	108.4 (1)	C52—C42—C32	120.3 (2)
C12—P—C2	111.6 (1)	C42—C52—C62	120.2 (2)
C13—P—C2	110.4 (1)	C52—C62—C12	119.9 (2)
C11—P—C2	108.1 (1)	C23—C13—C63	120.1 (2)
C1—C2—P	115.3 (2)	C23—C13—P	118.0 (2)
C1—C2—H2A	108.4	C63—C13—P	121.9 (2)
P—C2—H2A	108.4	C33—C23—C13	119.5 (2)
C61—C11—C21	120.3 (2)	C23—C33—C43	120.2 (2)
C61—C11—P	119.6 (2)	C53—C43—C33	120.4 (2)
C21—C11—P	120.0 (2)	C43—C53—C63	120.1 (2)
C31—C21—C11	119.6 (2)	C53—C63—C13	119.7 (2)
C21—C31—C41	120.0 (2)
C11—P—C2—C1	163.9 (2)	C62—C12—C22—C32	−1.0 (3)
C12—P—C2—C1	−76.8 (2)	P—C12—C22—C32	178.1 (2)
C13—P—C2—C1	45.5 (2)	C12—C22—C32—C42	0.7 (3)
C12—P—C11—C61	82.2 (2)	C22—C32—C42—C52	−0.5 (4)
C13—P—C11—C61	−36.8 (2)	C32—C42—C52—C62	0.7 (4)
C2—P—C11—C61	−156.6 (2)	C42—C52—C62—C12	−1.0 (3)
C12—P—C11—C21	−94.1 (2)	C22—C12—C62—C52	1.2 (3)
C13—P—C11—C21	146.8 (2)	P—C12—C62—C52	−178.0 (2)
C2—P—C11—C21	27.1 (2)	C12—P—C13—C23	173.0 (2)
C61—C11—C21—C31	−1.1 (3)	C11—P—C13—C23	−68.6 (2)
P—C11—C21—C31	175.3 (2)	C2—P—C13—C23	49.6 (2)
C11—C21—C31—C41	−0.1 (3)	C12—P—C13—C63	−6.4 (2)
C21—C31—C41—C51	1.0 (3)	C11—P—C13—C63	112.0 (2)
C31—C41—C51—C61	−0.7 (3)	C2—P—C13—C63	−129.7 (2)
C21—C11—C61—C51	1.3 (3)	C63—C13—C23—C33	0.1 (3)
P—C11—C61—C51	−175.1 (2)	P—C13—C23—C33	−179.3 (2)
C41—C51—C61—C11	−0.4 (3)	C13—C23—C33—C43	0.3 (3)
C13—P—C12—C22	−114.1 (2)	C23—C33—C43—C53	−0.9 (3)
C11—P—C12—C22	127.6 (2)	C33—C43—C53—C63	1.1 (3)
C2—P—C12—C22	8.5 (2)	C43—C53—C63—C13	−0.8 (3)
C13—P—C12—C62	65.0 (2)	C23—C13—C63—C53	0.1 (3)
C11—P—C12—C62	−53.3 (2)	P—C13—C63—C53	179.5 (2)
C2—P—C12—C62	−172.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O4^i	0.99	2.55	3.409 (3)	145
C23—H23···O4^i	0.95	2.49	3.369 (3)	154
C33—H33···O1^i	0.95	2.58	3.341 (3)	137
C61—H61···O2^ii	0.95	2.45	3.301 (3)	149

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

(II)

Crystal data

(C19H17IP)[ReO4]	F(000) = 1224
Mr = 653.40	Dx = 2.189 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5124 reflections
a = 10.116 (3) Å	θ = 3.5–28.0°
b = 15.478 (3) Å	µ = 7.79 mm^−1
c = 12.748 (3) Å	T = 100 K
β = 96.62 (3)°	Prism, colourless
V = 1982.7 (9) Å^3	0.25 × 0.25 × 0.10 mm
Z = 4

Data collection

Kuma KM4 CCD area-detector diffractometer	4653 independent reflections
Radiation source: fine-focus sealed tube	3930 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
ω scans	θmax = 28.0°, θmin = 3.5°
Absorption correction: empirical (using intensity measurements) Walker & Stuart (1983)	h = −13→13
Tmin = 0.202, Tmax = 0.457	k = −20→20
11836 measured reflections	l = −16→9

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.056	w = 1/[σ^2(Fo^2) + (0.03P)^2 + 0.2481P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.002
4653 reflections	Δρmax = 1.28 e Å^−3
236 parameters	Δρmin = −1.28 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00069 (9)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Re	0.100932 (13)	0.078365 (9)	0.765284 (10)	0.01237 (5)
O1	0.0921 (3)	0.18336 (16)	0.8090 (2)	0.0203 (5)
O2	0.0427 (3)	0.01187 (17)	0.8581 (2)	0.0250 (6)
O3	0.0028 (3)	0.06763 (18)	0.6474 (2)	0.0286 (7)
O4	0.2635 (3)	0.05258 (19)	0.7505 (3)	0.0323 (7)
I	0.27703 (2)	0.266735 (17)	0.512317 (19)	0.02245 (7)
P	0.58407 (8)	0.28114 (6)	0.62572 (7)	0.01086 (17)
C1	0.4644 (3)	0.3320 (2)	0.5298 (3)	0.0147 (7)
H1A	0.5002	0.3332	0.4607	0.018*
H1B	0.4510	0.3925	0.5515	0.018*
C11	0.5273 (3)	0.2854 (2)	0.7535 (2)	0.0123 (7)
C21	0.4505 (3)	0.2197 (2)	0.7914 (3)	0.0166 (7)
H21	0.4264	0.1703	0.7493	0.020*
C31	0.4101 (3)	0.2277 (2)	0.8914 (3)	0.0190 (8)
H31	0.3606	0.1825	0.9188	0.023*
C41	0.4412 (3)	0.3007 (2)	0.9515 (3)	0.0179 (7)
H41	0.4134	0.3052	1.0200	0.021*
C51	0.5126 (3)	0.3677 (2)	0.9127 (3)	0.0163 (7)
H51	0.5313	0.4184	0.9535	0.020*
C61	0.5567 (3)	0.3602 (2)	0.8136 (3)	0.0141 (7)
H61	0.6065	0.4056	0.7868	0.017*
C12	0.7355 (3)	0.3435 (2)	0.6286 (3)	0.0119 (6)
C22	0.7361 (4)	0.4249 (2)	0.5821 (3)	0.0146 (7)
H22	0.6563	0.4487	0.5472	0.018*
C32	0.8546 (4)	0.4712 (2)	0.5869 (3)	0.0182 (7)
H32	0.8557	0.5268	0.5552	0.022*
C42	0.9717 (4)	0.4364 (2)	0.6381 (3)	0.0197 (8)
H42	1.0522	0.4684	0.6416	0.024*
C52	0.9707 (3)	0.3553 (2)	0.6838 (3)	0.0170 (7)
H52	1.0510	0.3314	0.7178	0.020*
C62	0.8529 (3)	0.3086 (2)	0.6801 (3)	0.0158 (7)
H62	0.8522	0.2533	0.7123	0.019*
C13	0.6148 (3)	0.1724 (2)	0.5878 (3)	0.0138 (7)
C23	0.6144 (4)	0.1539 (2)	0.4800 (3)	0.0176 (7)
H23	0.5930	0.1978	0.4287	0.021*
C33	0.6454 (4)	0.0714 (2)	0.4489 (3)	0.0194 (8)
H33	0.6453	0.0587	0.3759	0.023*
C43	0.6764 (4)	0.0077 (2)	0.5230 (3)	0.0233 (8)
H43	0.6976	−0.0488	0.5010	0.028*
C53	0.6767 (4)	0.0256 (2)	0.6292 (3)	0.0218 (8)
H53	0.6967	−0.0189	0.6799	0.026*
C63	0.6477 (4)	0.1085 (2)	0.6623 (3)	0.0196 (7)
H63	0.6504	0.1211	0.7354	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re	0.01645 (8)	0.00972 (8)	0.01136 (8)	−0.00080 (5)	0.00341 (5)	−0.00022 (5)
O1	0.0264 (14)	0.0133 (13)	0.0223 (13)	0.0001 (11)	0.0076 (11)	0.0007 (11)
O2	0.0411 (16)	0.0176 (14)	0.0171 (13)	−0.0082 (12)	0.0068 (12)	0.0033 (11)
O3	0.0411 (17)	0.0268 (16)	0.0160 (13)	−0.0042 (13)	−0.0052 (12)	0.0016 (11)
O4	0.0236 (14)	0.0242 (15)	0.0511 (19)	0.0007 (12)	0.0122 (14)	−0.0109 (14)
I	0.01767 (12)	0.02169 (14)	0.02689 (14)	−0.00249 (10)	−0.00217 (10)	0.00136 (10)
P	0.0128 (4)	0.0105 (4)	0.0098 (4)	0.0002 (3)	0.0030 (3)	0.0003 (3)
C1	0.0167 (16)	0.0134 (17)	0.0133 (16)	−0.0009 (14)	−0.0005 (13)	0.0015 (13)
C11	0.0103 (15)	0.0183 (17)	0.0093 (15)	0.0018 (13)	0.0045 (12)	0.0024 (13)
C21	0.0153 (16)	0.0183 (18)	0.0159 (17)	−0.0024 (14)	0.0014 (13)	−0.0003 (14)
C31	0.0160 (16)	0.0228 (19)	0.0193 (18)	−0.0046 (15)	0.0071 (14)	0.0052 (15)
C41	0.0153 (16)	0.026 (2)	0.0139 (17)	0.0052 (15)	0.0066 (13)	0.0016 (15)
C51	0.0177 (16)	0.0181 (18)	0.0133 (16)	0.0045 (14)	0.0031 (13)	−0.0010 (14)
C61	0.0151 (16)	0.0139 (16)	0.0135 (16)	0.0018 (13)	0.0029 (13)	0.0033 (13)
C12	0.0161 (16)	0.0107 (16)	0.0104 (15)	−0.0014 (13)	0.0080 (13)	−0.0023 (13)
C22	0.0174 (16)	0.0161 (17)	0.0110 (16)	0.0010 (14)	0.0043 (13)	−0.0003 (13)
C32	0.0224 (18)	0.0153 (18)	0.0183 (18)	−0.0035 (15)	0.0079 (14)	−0.0004 (14)
C42	0.0198 (17)	0.020 (2)	0.0208 (18)	−0.0077 (15)	0.0085 (15)	−0.0043 (15)
C52	0.0138 (16)	0.0203 (18)	0.0172 (18)	−0.0009 (14)	0.0026 (14)	−0.0025 (15)
C62	0.0195 (17)	0.0156 (17)	0.0131 (16)	−0.0020 (14)	0.0056 (14)	0.0001 (14)
C13	0.0151 (16)	0.0109 (16)	0.0161 (17)	−0.0013 (13)	0.0040 (13)	−0.0008 (13)
C23	0.0222 (18)	0.0134 (17)	0.0176 (18)	−0.0009 (14)	0.0042 (14)	0.0012 (14)
C33	0.0178 (17)	0.0170 (19)	0.0242 (19)	−0.0042 (15)	0.0057 (15)	−0.0079 (15)
C43	0.0169 (17)	0.0106 (17)	0.043 (2)	0.0019 (14)	0.0068 (17)	−0.0043 (16)
C53	0.0242 (19)	0.0116 (17)	0.030 (2)	0.0078 (15)	0.0062 (16)	0.0053 (15)
C63	0.0199 (17)	0.0175 (18)	0.0212 (18)	0.0027 (15)	0.0013 (15)	0.0028 (16)

Geometric parameters (Å, º)

Re—O3	1.711 (3)	C13—C23	1.403 (5)
Re—O2	1.722 (3)	C23—C33	1.384 (5)
Re—O1	1.723 (2)	C33—C43	1.377 (5)
Re—O4	1.724 (3)	C43—C53	1.382 (5)
I—C1	2.137 (3)	C53—C63	1.393 (5)
P—C11	1.790 (3)	C1—H1A	0.9900
P—C12	1.807 (4)	C1—H1B	0.9900
P—C13	1.788 (4)	C21—H21	0.9500
P—C1	1.800 (3)	C31—H31	0.9500
C11—C21	1.399 (5)	C41—H41	0.9500
C11—C61	1.401 (5)	C51—H51	0.9500
C21—C31	1.389 (5)	C61—H61	0.9500
C31—C41	1.381 (5)	C22—H22	0.9500
C41—C51	1.386 (5)	C32—H32	0.9500
C51—C61	1.392 (5)	C42—H42	0.9500
C12—C22	1.393 (5)	C52—H52	0.9500
C12—C62	1.398 (5)	C62—H62	0.9500
C22—C32	1.392 (5)	C23—H23	0.9500
C32—C42	1.393 (5)	C33—H33	0.9500
C42—C52	1.385 (5)	C43—H43	0.9500
C52—C62	1.390 (5)	C53—H53	0.9500
C13—C63	1.385 (5)	C63—H63	0.9500
O3—Re—O2	109.6 (1)	C41—C31—C21	120.6 (3)
O3—Re—O1	109.2 (1)	C31—C41—C51	120.6 (3)
O2—Re—O1	107.9 (1)	C41—C51—C61	119.8 (3)
O3—Re—O4	110.2 (2)	C51—C61—C11	119.6 (3)
O2—Re—O4	110.1 (2)	C22—C12—C62	120.3 (3)
O1—Re—O4	109.8 (1)	C22—C12—P	121.3 (3)
C13—P—C11	111.4 (2)	C62—C12—P	118.4 (3)
C13—P—C1	110.6 (2)	C32—C22—C12	119.6 (3)
C11—P—C1	110.0 (1)	C22—C32—C42	120.2 (3)
C13—P—C12	109.6 (2)	C52—C42—C32	120.1 (3)
C11—P—C12	108.8 (2)	C42—C52—C62	120.3 (3)
C1—P—C12	106.4 (2)	C52—C62—C12	119.6 (3)
P—C1—I	112.5 (2)	C63—C13—C23	119.9 (3)
P—C1—H1A	109.1	C63—C13—P	121.5 (3)
I—C1—H1A	109.1	C23—C13—P	118.4 (3)
P—C1—H1B	109.1	C33—C23—C13	119.6 (3)
I—C1—H1B	109.1	C43—C33—C23	120.4 (4)
C21—C11—C61	120.2 (3)	C33—C43—C53	120.2 (3)
C21—C11—P	122.5 (3)	C43—C53—C63	120.3 (3)
C61—C11—P	117.2 (2)	C13—C63—C53	119.6 (3)
C31—C21—C11	119.1 (3)
C11—P—C1—I	−63.1 (2)	C62—C12—C22—C32	0.1 (5)
C12—P—C1—I	179.2 (2)	P—C12—C22—C32	179.4 (3)
C13—P—C1—I	60.3 (2)	C12—C22—C32—C42	−0.1 (5)
C13—P—C11—C21	−32.1 (3)	C22—C32—C42—C52	0.4 (5)
C1—P—C11—C21	90.9 (3)	C32—C42—C52—C62	−0.8 (5)
C12—P—C11—C21	−152.9 (3)	C42—C52—C62—C12	0.9 (5)
C13—P—C11—C61	151.3 (3)	C22—C12—C62—C52	−0.6 (5)
C1—P—C11—C61	−85.7 (3)	P—C12—C62—C52	−179.8 (3)
C12—P—C11—C61	30.4 (3)	C11—P—C13—C63	−26.4 (3)
C61—C11—C21—C31	−3.4 (5)	C1—P—C13—C63	−149.0 (3)
P—C11—C21—C31	−179.9 (3)	C12—P—C13—C63	94.0 (3)
C11—C21—C31—C41	2.2 (5)	C11—P—C13—C23	158.2 (3)
C21—C31—C41—C51	0.4 (5)	C1—P—C13—C23	35.6 (3)
C31—C41—C51—C61	−1.9 (5)	C12—P—C13—C23	−81.4 (3)
C41—C51—C61—C11	0.7 (5)	C63—C13—C23—C33	0.8 (5)
C21—C11—C61—C51	2.0 (5)	P—C13—C23—C33	176.3 (3)
P—C11—C61—C51	178.7 (3)	C13—C23—C33—C43	0.1 (5)
C13—P—C12—C22	133.4 (3)	C23—C33—C43—C53	0.0 (5)
C11—P—C12—C22	−104.7 (3)	C33—C43—C53—C63	−1.0 (6)
C1—P—C12—C22	13.7 (3)	C23—C13—C63—C53	−1.7 (5)
C13—P—C12—C62	−47.4 (3)	P—C13—C63—C53	−177.1 (3)
C11—P—C12—C62	74.6 (3)	C43—C53—C63—C13	1.8 (5)
C1—P—C12—C62	−167.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O4	0.95	2.46	3.211 (5)	136
C51—H51···O3^i	0.95	2.53	3.169 (4)	125
C42—H42···O4^ii	0.95	2.54	3.398 (5)	150
C52—H52···O1^iii	0.95	2.58	3.269 (5)	130
C23—H23···O1^iv	0.95	2.39	3.322 (4)	167
C33—H33···O4^v	0.95	2.60	3.395 (5)	142

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+3/2, y+1/2, −z+3/2; (iii) x+1, y, z; (iv) x+1/2, −y+1/2, z−1/2; (v) −x+1, −y, −z+1.