Synthesis of Re^I tricarbonyl complexes with various sulfur- and oxygen-donating ligands: crystal structures of two Re^I dinuclear structures bridged by S atoms

The synthesis and characterization of two dinuclear complexes, namely fac-hexa­carbonyl-1κ³C,2κ³C-(pyridine-1κN)[μ-2,2′-sulfanediyldi(ethanethiol­ato)-1κ²S¹,S³:2κ³S¹,S²,S³]dirhenium(I), [Re₂(C₄H₈S₃)(C₅H₅N)(CO)₆], (1), and tetra­ethyl­ammonium fac-tris­(μ-2-meth­oxy­benzene­thiol­ato-κ²S:S)bis­[tri­carbonyl­rhenium(I)], (C₈H₂₀N)[Re₂(C₇H₇OS)₃(CO)₆], (2), together with two mononuclear complexes, namely (2,2′-bi­thio­phene-5-carb­oxy­lic acid-κ²S,S′)bromido­tri­carbonyl­rhenium(I), (3), and bromido­tricarbon­yl(methyl benzo[b]thio­phene-2-carboxyl­ate-κ²O,S)rhenium(I), (4), are reported. Crystals of (1) and (2) were characterized by X-ray diffraction. The crystal structure of (1) revealed two Re—S—Re bridges. The thio­ether S atom only bonds to one of the Re^I metal centres, while the geometry of the second Re^I metal centre is completed by a pyridine ligand. The structure of (2) is characterized by three S-atom bridges and an Re...Re nonbonding distance of 3.4879 (5) Å, which is shorter than the distance found for (1) [3.7996 (6)/3.7963 (6) Å], but still clearly a nonbonding distance. Complex (1) is stabilized by six inter­molecular hydrogen-bond inter­actions and an O...O inter­action, while (2) is stabilized by two inter­molecular hydrogen-bond inter­actions and two O...π inter­actions.

Computing details

For both structures, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) and WinGX (Farrugia, 2012); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and WinGX (Farrugia, 2012).

fac-Hexacarbonyl-1κ³C,2κ³C-(pyridine-1κN)[µ-2,2'-sulfanediyldi(ethanethiolato)-κ⁵1κ²S¹,S³:2κ³S¹,S²,S³]dirhenium(I) (shelx)

Crystal data

[Re2(C4H8S3)(C5H5N)(CO)6]	Z = 4
Mr = 771.86	F(000) = 1424
Triclinic, P1	Dx = 2.635 Mg m^−3
a = 9.4460 (19) Å	Mo Kα radiation, λ = 0.71069 Å
b = 14.885 (3) Å	Cell parameters from 9367 reflections
c = 15.910 (3) Å	θ = 4.1–28.3°
α = 104.676 (5)°	µ = 12.79 mm^−1
β = 106.554 (5)°	T = 100 K
γ = 104.430 (6)°	Plate, yellow
V = 1945.8 (7) Å^3	0.38 × 0.27 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer	8040 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.050
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 28.0°, θmin = 3.0°
Tmin = 0.023, Tmax = 0.258	h = −12→12
38894 measured reflections	k = −19→19
9417 independent reflections	l = −16→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0556P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.002
9360 reflections	Δρmax = 2.97 e Å^−3
487 parameters	Δρmin = −2.39 e Å^−3

Special details

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.

Refinement. A Bruker X8 APEXII 4K diffractometer equipped with graphite monochromated Mo Kα radiation with a wavelength of λ = 0.71073 Å and ω- and φ-scans at 100 K was used to collect the reflection data of all the structures reported here. The SIR97 (Altomare et al., 1999) package was used to solve all structures while it was refined with WinGX (Farrugia, 1999) and SHELXL97 (Sheldrick, 2008). The cell refinement was done with SAINT-Plus and the data reduction with SAINT-plus and XPREP (Bruker, 2008). The SADABS (Bruker, 2008) software package with the multi-scan technique was used to obtain absorption corrections, while the molecular graphics and presentation was done with Diamond (Brandenburg & Putz, 2005). All structures are drawn with thermal ellipsoids at a 50 % probability level. All non-hydrogen atoms were anisotropically refined.

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

	x	y	z	Uiso*/Ueq
C1'	0.4528 (6)	0.9546 (4)	0.3476 (3)	0.0180 (11)
C1	−0.0285 (6)	0.4698 (4)	0.3151 (3)	0.0190 (11)
C2'	0.4087 (6)	0.8187 (4)	0.4263 (3)	0.0193 (11)
C2	−0.0421 (6)	0.3541 (4)	0.4186 (4)	0.0218 (12)
C3	0.2318 (6)	0.4603 (4)	0.4184 (4)	0.0197 (11)
C3'	0.7044 (6)	0.9265 (4)	0.4519 (4)	0.0195 (11)
C4'	0.4205 (6)	0.6103 (4)	0.0949 (3)	0.0152 (10)
C4	−0.0626 (6)	0.1116 (4)	0.0920 (4)	0.0185 (11)
C5	0.1762 (6)	0.1597 (3)	0.0402 (4)	0.0164 (11)
C5'	0.6770 (5)	0.6659 (3)	0.0647 (3)	0.0153 (10)
C6	0.1891 (6)	0.0598 (4)	0.1590 (3)	0.0164 (10)
C6'	0.6483 (5)	0.5424 (4)	0.1594 (3)	0.0144 (10)
C11'	0.2465 (6)	0.7752 (4)	0.1504 (4)	0.0196 (11)
H11'	0.3078	0.8367	0.1511	0.024*
C11	−0.2587 (6)	0.2654 (4)	0.1386 (3)	0.0179 (11)
H11	−0.2117	0.3239	0.1283	0.021*
C12'	0.1081 (6)	0.7202 (4)	0.0752 (4)	0.0237 (12)
H12'	0.0738	0.7445	0.0261	0.028*
C12	−0.4023 (6)	0.1991 (4)	0.0734 (4)	0.0240 (12)
H12	−0.4514	0.2117	0.0188	0.029*
C13'	0.0187 (6)	0.6285 (4)	0.0717 (4)	0.0255 (12)
H13'	−0.0746	0.5875	0.0191	0.031*
C13	−0.4747 (7)	0.1146 (4)	0.0875 (4)	0.0297 (14)
H13	−0.5736	0.0681	0.0433	0.036*
C14'	0.0699 (6)	0.5988 (4)	0.1472 (4)	0.0235 (12)
H14'	0.0096	0.5379	0.1482	0.028*
C14	−0.3980 (6)	0.0996 (4)	0.1687 (4)	0.0267 (13)
H14	−0.4453	0.0431	0.1815	0.032*
C15	−0.2528 (6)	0.1673 (4)	0.2304 (4)	0.0189 (11)
H15	−0.2005	0.1551	0.2846	0.023*
C15'	0.2085 (6)	0.6581 (4)	0.2206 (4)	0.0181 (11)
H15'	0.2420	0.6365	0.2717	0.022*
C16	0.3284 (5)	0.4319 (3)	0.2222 (3)	0.0149 (10)
H16A	0.3565	0.4277	0.1663	0.018*
H16B	0.3334	0.5007	0.2500	0.018*
C16'	0.8409 (5)	0.9289 (4)	0.2719 (4)	0.0199 (11)
H6A'	0.8543	0.9820	0.2449	0.024*
H6B'	0.8672	0.9605	0.3397	0.024*
C17	0.4506 (5)	0.4109 (3)	0.2927 (3)	0.0139 (10)
H17A	0.4338	0.4253	0.3527	0.017*
H17B	0.5570	0.4551	0.3044	0.017*
C17'	0.9563 (6)	0.8766 (4)	0.2589 (3)	0.0201 (12)
H7A'	1.0635	0.9211	0.3028	0.024*
H7B'	0.9550	0.8655	0.1946	0.024*
C18	0.4685 (5)	0.2523 (4)	0.3576 (3)	0.0131 (10)
H18A	0.4674	0.1834	0.3430	0.016*
H18B	0.5743	0.2960	0.4040	0.016*
C18'	0.9241 (6)	0.7923 (4)	0.3980 (3)	0.0161 (10)
H8A'	1.0278	0.7980	0.4408	0.019*
H8B'	0.9118	0.8578	0.4164	0.019*
C19'	0.7958 (5)	0.7170 (4)	0.4081 (3)	0.0167 (10)
H9A'	0.7998	0.7410	0.4730	0.020*
H9B'	0.8186	0.6545	0.3987	0.020*
C19	0.3496 (6)	0.2622 (4)	0.4018 (3)	0.0187 (11)
H19A	0.3783	0.3330	0.4383	0.022*
H19B	0.3574	0.2261	0.4464	0.022*
O1'	0.4119 (5)	1.0212 (3)	0.3533 (3)	0.0336 (10)
O1	−0.0646 (5)	0.5377 (3)	0.3143 (3)	0.0341 (10)
O2	−0.0943 (5)	0.3505 (3)	0.4749 (3)	0.0353 (11)
O2'	0.3386 (4)	0.8048 (3)	0.4728 (3)	0.0274 (9)
O3	0.3406 (4)	0.5227 (3)	0.4781 (3)	0.0314 (10)
O3'	0.8138 (4)	0.9786 (3)	0.5170 (3)	0.0296 (9)
O4	−0.1925 (4)	0.0664 (3)	0.0461 (3)	0.0292 (9)
O4'	0.2952 (4)	0.5696 (3)	0.0393 (3)	0.0244 (9)
O5'	0.6941 (5)	0.6544 (3)	−0.0059 (2)	0.0247 (9)
O5	0.1829 (5)	0.1385 (3)	−0.0326 (2)	0.0237 (8)
O6'	0.6524 (4)	0.4637 (3)	0.1469 (3)	0.0258 (9)
O6	0.2074 (5)	−0.0145 (3)	0.1570 (3)	0.0272 (9)
S1'	0.63285 (14)	0.84711 (9)	0.21773 (8)	0.0148 (3)
S1	0.12634 (14)	0.34905 (8)	0.18476 (8)	0.0120 (2)
S2'	0.91872 (14)	0.75825 (9)	0.27740 (8)	0.0156 (3)
S2	0.43932 (14)	0.28216 (9)	0.25112 (8)	0.0125 (2)
S3'	0.59507 (14)	0.68946 (9)	0.32766 (8)	0.0126 (2)
S3	0.14171 (14)	0.21607 (9)	0.32023 (8)	0.0132 (2)
Re1	0.04390 (2)	0.36181 (2)	0.32351 (2)	0.01148 (6)
Re1'	0.51906 (2)	0.84208 (2)	0.34481 (2)	0.01152 (6)
Re2	0.15856 (2)	0.18366 (2)	0.16109 (2)	0.01003 (6)
Re2'	0.63840 (2)	0.67300 (2)	0.17761 (2)	0.01135 (6)
N1'	0.2993 (5)	0.7456 (3)	0.2235 (3)	0.0144 (9)
N1	−0.1823 (5)	0.2502 (3)	0.2168 (3)	0.0145 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1'	0.022 (3)	0.011 (2)	0.017 (3)	0.006 (2)	0.003 (2)	0.0029 (19)
C1	0.016 (3)	0.023 (3)	0.011 (2)	0.009 (2)	0.0002 (19)	−0.001 (2)
C2'	0.014 (2)	0.020 (3)	0.014 (2)	0.005 (2)	−0.007 (2)	0.004 (2)
C2	0.017 (3)	0.024 (3)	0.016 (3)	0.005 (2)	−0.001 (2)	0.004 (2)
C3	0.014 (3)	0.022 (3)	0.019 (3)	0.009 (2)	0.001 (2)	0.003 (2)
C3'	0.018 (3)	0.017 (3)	0.021 (3)	0.004 (2)	0.006 (2)	0.006 (2)
C4'	0.017 (3)	0.014 (2)	0.016 (2)	0.005 (2)	0.010 (2)	0.0017 (19)
C4	0.019 (3)	0.012 (2)	0.020 (3)	0.003 (2)	0.007 (2)	0.001 (2)
C5	0.012 (2)	0.009 (2)	0.020 (3)	0.0008 (18)	−0.0014 (19)	0.0036 (19)
C5'	0.011 (2)	0.012 (2)	0.016 (3)	−0.0005 (18)	0.0008 (19)	0.0039 (19)
C6	0.019 (3)	0.016 (2)	0.016 (2)	0.004 (2)	0.010 (2)	0.005 (2)
C6'	0.011 (2)	0.020 (3)	0.013 (2)	0.0065 (19)	0.0078 (19)	0.003 (2)
C11'	0.023 (3)	0.014 (2)	0.020 (3)	0.008 (2)	0.004 (2)	0.005 (2)
C11	0.016 (3)	0.016 (2)	0.020 (3)	0.009 (2)	0.005 (2)	0.003 (2)
C12'	0.023 (3)	0.021 (3)	0.020 (3)	0.011 (2)	−0.002 (2)	0.004 (2)
C12	0.016 (3)	0.025 (3)	0.020 (3)	0.008 (2)	−0.002 (2)	−0.002 (2)
C13'	0.010 (2)	0.022 (3)	0.029 (3)	0.004 (2)	0.000 (2)	−0.006 (2)
C13	0.018 (3)	0.015 (3)	0.037 (3)	0.001 (2)	0.004 (2)	−0.010 (2)
C14'	0.014 (3)	0.019 (3)	0.034 (3)	0.004 (2)	0.011 (2)	0.002 (2)
C14	0.014 (3)	0.018 (3)	0.044 (4)	0.004 (2)	0.012 (2)	0.005 (2)
C15	0.018 (3)	0.017 (3)	0.025 (3)	0.009 (2)	0.011 (2)	0.006 (2)
C15'	0.018 (3)	0.016 (2)	0.024 (3)	0.007 (2)	0.012 (2)	0.006 (2)
C16	0.016 (2)	0.008 (2)	0.015 (2)	−0.0020 (18)	0.0035 (19)	0.0032 (18)
C16'	0.016 (3)	0.014 (2)	0.024 (3)	−0.001 (2)	0.004 (2)	0.007 (2)
C17	0.014 (2)	0.009 (2)	0.014 (2)	0.0013 (18)	0.0045 (18)	0.0002 (18)
C17'	0.018 (3)	0.022 (3)	0.013 (2)	−0.004 (2)	0.005 (2)	0.006 (2)
C18	0.011 (2)	0.017 (2)	0.014 (2)	0.0084 (19)	0.0042 (18)	0.0071 (19)
C18'	0.014 (2)	0.022 (3)	0.010 (2)	0.006 (2)	0.0043 (18)	0.0032 (19)
C19'	0.016 (2)	0.020 (3)	0.017 (2)	0.009 (2)	0.0066 (19)	0.008 (2)
C19	0.018 (3)	0.022 (3)	0.020 (3)	0.009 (2)	0.007 (2)	0.012 (2)
O1'	0.048 (3)	0.020 (2)	0.033 (2)	0.0196 (19)	0.008 (2)	0.0088 (17)
O1	0.044 (3)	0.026 (2)	0.026 (2)	0.024 (2)	0.0017 (19)	0.0011 (17)
O2	0.032 (2)	0.058 (3)	0.022 (2)	0.018 (2)	0.0146 (18)	0.016 (2)
O2'	0.026 (2)	0.038 (2)	0.021 (2)	0.0091 (18)	0.0114 (17)	0.0136 (18)
O3	0.017 (2)	0.028 (2)	0.028 (2)	0.0050 (17)	−0.0029 (16)	−0.0085 (17)
O3'	0.021 (2)	0.031 (2)	0.020 (2)	0.0024 (17)	0.0007 (16)	−0.0019 (17)
O4	0.0126 (19)	0.022 (2)	0.033 (2)	0.0007 (16)	0.0038 (16)	−0.0114 (17)
O4'	0.0115 (18)	0.026 (2)	0.024 (2)	0.0043 (16)	0.0015 (15)	−0.0024 (16)
O5'	0.031 (2)	0.027 (2)	0.0165 (19)	0.0071 (17)	0.0121 (16)	0.0076 (16)
O5	0.037 (2)	0.026 (2)	0.0109 (18)	0.0133 (17)	0.0120 (16)	0.0067 (15)
O6'	0.030 (2)	0.0153 (19)	0.028 (2)	0.0097 (16)	0.0056 (17)	0.0053 (16)
O6	0.034 (2)	0.0144 (19)	0.032 (2)	0.0128 (17)	0.0073 (18)	0.0077 (16)
S1'	0.0158 (6)	0.0112 (6)	0.0137 (6)	0.0012 (5)	0.0023 (5)	0.0055 (5)
S1	0.0132 (6)	0.0091 (5)	0.0111 (5)	0.0025 (4)	0.0023 (4)	0.0034 (4)
S2'	0.0122 (6)	0.0187 (6)	0.0136 (6)	0.0041 (5)	0.0035 (5)	0.0046 (5)
S2	0.0111 (6)	0.0109 (6)	0.0137 (6)	0.0029 (4)	0.0040 (4)	0.0033 (4)
S3'	0.0138 (6)	0.0103 (5)	0.0126 (6)	0.0032 (4)	0.0037 (4)	0.0044 (4)
S3	0.0119 (6)	0.0137 (6)	0.0135 (6)	0.0038 (5)	0.0034 (4)	0.0061 (5)
Re1	0.00995 (11)	0.01149 (10)	0.00995 (11)	0.00367 (8)	0.00160 (8)	0.00123 (8)
Re1'	0.01199 (11)	0.00891 (10)	0.01091 (11)	0.00270 (8)	0.00212 (8)	0.00237 (8)
Re2	0.01013 (10)	0.00711 (10)	0.01020 (10)	0.00176 (7)	0.00220 (8)	0.00176 (7)
Re2'	0.01091 (11)	0.01032 (10)	0.01037 (11)	0.00218 (8)	0.00275 (8)	0.00249 (8)
N1'	0.013 (2)	0.0100 (19)	0.014 (2)	0.0038 (16)	0.0010 (16)	−0.0005 (16)
N1	0.0081 (19)	0.014 (2)	0.014 (2)	0.0005 (16)	0.0008 (16)	−0.0009 (16)

Geometric parameters (Å, º)

C1'—O1'	1.142 (6)	C15—H15	0.9500
C1'—Re1'	1.924 (5)	C15'—N1'	1.351 (6)
C1—O1	1.146 (6)	C15'—H15'	0.9500
C1—Re1	1.917 (5)	C16—C17	1.519 (6)
C2'—O2'	1.147 (7)	C16—S1	1.823 (4)
C2'—Re1'	1.926 (6)	C16—H16A	0.9900
C2—O2	1.144 (7)	C16—H16B	0.9900
C2—Re1	1.925 (6)	C16'—C17'	1.518 (7)
C3—O3	1.159 (6)	C16'—S1'	1.843 (5)
C3—Re1	1.906 (5)	C16'—H6A'	0.9900
C3'—O3'	1.151 (6)	C16'—H6B'	0.9900
C3'—Re1'	1.914 (5)	C17—S2	1.827 (5)
C4'—O4'	1.151 (6)	C17—H17A	0.9900
C4'—Re2'	1.927 (5)	C17—H17B	0.9900
C4—O4	1.150 (6)	C17'—S2'	1.824 (5)
C4—Re2	1.923 (5)	C17'—H7A'	0.9900
C5—O5	1.145 (6)	C17'—H7B'	0.9900
C5—Re2	1.929 (5)	C18—C19	1.503 (7)
C5'—O5'	1.157 (6)	C18—S2	1.821 (5)
C5'—Re2'	1.915 (5)	C18—H18A	0.9900
C6—O6	1.156 (6)	C18—H18B	0.9900
C6—Re2	1.929 (5)	C18'—C19'	1.509 (7)
C6'—O6'	1.151 (6)	C18'—S2'	1.839 (5)
C6'—Re2'	1.921 (5)	C18'—H8A'	0.9900
C11'—N1'	1.355 (6)	C18'—H8B'	0.9900
C11'—C12'	1.374 (7)	C19'—S3'	1.834 (5)
C11'—H11'	0.9500	C19'—H9A'	0.9900
C11—N1	1.353 (6)	C19'—H9B'	0.9900
C11—C12	1.379 (7)	C19—S3	1.853 (5)
C11—H11	0.9500	C19—H19A	0.9900
C12'—C13'	1.393 (7)	C19—H19B	0.9900
C12'—H12'	0.9500	S1'—Re2'	2.5250 (13)
C12—C13	1.380 (8)	S1'—Re1'	2.5540 (13)
C12—H12	0.9500	S1—Re2	2.5028 (13)
C13'—C14'	1.383 (8)	S1—Re1	2.5212 (13)
C13'—H13'	0.9500	S2'—Re2'	2.4599 (13)
C13—C14	1.391 (8)	S2—Re2	2.4633 (12)
C13—H13	0.9500	S3'—Re2'	2.4975 (13)
C14'—C15'	1.374 (7)	S3'—Re1'	2.5222 (13)
C14'—H14'	0.9500	S3—Re2	2.5135 (13)
C14—C15	1.379 (7)	S3—Re1	2.5558 (13)
C14—H14	0.9500	Re1—N1	2.223 (4)
C15—N1	1.349 (6)	Re1'—N1'	2.219 (4)
O1'—C1'—Re1'	176.5 (5)	C18—C19—H19B	108.3
O1—C1—Re1	176.2 (4)	S3—C19—H19B	108.3
O2'—C2'—Re1'	177.7 (4)	H19A—C19—H19B	107.4
O2—C2—Re1	178.9 (5)	C16'—S1'—Re2'	105.45 (17)
O3—C3—Re1	176.0 (5)	C16'—S1'—Re1'	109.54 (18)
O3'—C3'—Re1'	178.3 (5)	Re2'—S1'—Re1'	96.74 (4)
O4'—C4'—Re2'	173.8 (5)	C16—S1—Re2	102.14 (16)
O4—C4—Re2	175.8 (5)	C16—S1—Re1	110.01 (16)
O5—C5—Re2	175.1 (4)	Re2—S1—Re1	98.27 (4)
O5'—C5'—Re2'	175.1 (4)	C17'—S2'—C18'	102.6 (2)
O6—C6—Re2	179.5 (5)	C17'—S2'—Re2'	101.33 (16)
O6'—C6'—Re2'	178.8 (4)	C18'—S2'—Re2'	105.16 (16)
N1'—C11'—C12'	123.0 (5)	C18—S2—C17	101.6 (2)
N1'—C11'—H11'	118.5	C18—S2—Re2	100.76 (15)
C12'—C11'—H11'	118.5	C17—S2—Re2	106.12 (15)
N1—C11—C12	122.4 (5)	C19'—S3'—Re2'	100.53 (17)
N1—C11—H11	118.8	C19'—S3'—Re1'	112.00 (17)
C12—C11—H11	118.8	Re2'—S3'—Re1'	98.27 (4)
C11'—C12'—C13'	119.3 (5)	C19—S3—Re2	104.14 (17)
C11'—C12'—H12'	120.4	C19—S3—Re1	109.36 (17)
C13'—C12'—H12'	120.4	Re2—S3—Re1	97.10 (4)
C11—C12—C13	120.1 (5)	C3—Re1—C1	85.7 (2)
C11—C12—H12	120.0	C3—Re1—C2	88.6 (2)
C13—C12—H12	120.0	C1—Re1—C2	88.2 (2)
C14'—C13'—C12'	118.0 (5)	C3—Re1—N1	177.1 (2)
C14'—C13'—H13'	121.0	C1—Re1—N1	92.51 (18)
C12'—C13'—H13'	121.0	C2—Re1—N1	89.00 (18)
C12—C13—C14	117.7 (5)	C3—Re1—S1	99.04 (17)
C12—C13—H13	121.1	C1—Re1—S1	94.68 (16)
C14—C13—H13	121.1	C2—Re1—S1	171.99 (15)
C15'—C14'—C13'	119.6 (5)	N1—Re1—S1	83.41 (11)
C15'—C14'—H14'	120.2	C3—Re1—S3	96.10 (16)
C13'—C14'—H14'	120.2	C1—Re1—S3	174.85 (16)
C15—C14—C13	119.7 (5)	C2—Re1—S3	96.70 (17)
C15—C14—H14	120.1	N1—Re1—S3	85.89 (11)
C13—C14—H14	120.1	S1—Re1—S3	80.28 (4)
N1—C15—C14	122.5 (5)	C3'—Re1'—C1'	88.5 (2)
N1—C15—H15	118.7	C3'—Re1'—C2'	89.7 (2)
C14—C15—H15	118.7	C1'—Re1'—C2'	86.8 (2)
N1'—C15'—C14'	123.1 (5)	C3'—Re1'—N1'	178.1 (2)
N1'—C15'—H15'	118.4	C1'—Re1'—N1'	90.45 (18)
C14'—C15'—H15'	118.4	C2'—Re1'—N1'	88.62 (18)
C17—C16—S1	115.0 (3)	C3'—Re1'—S3'	95.23 (16)
C17—C16—H16A	108.5	C1'—Re1'—S3'	175.59 (15)
S1—C16—H16A	108.5	C2'—Re1'—S3'	95.47 (16)
C17—C16—H16B	108.5	N1'—Re1'—S3'	85.84 (11)
S1—C16—H16B	108.5	C3'—Re1'—S1'	98.70 (17)
H16A—C16—H16B	107.5	C1'—Re1'—S1'	96.91 (16)
C17'—C16'—S1'	114.3 (3)	C2'—Re1'—S1'	170.91 (15)
C17'—C16'—H6A'	108.7	N1'—Re1'—S1'	83.08 (12)
S1'—C16'—H6A'	108.7	S3'—Re1'—S1'	80.29 (4)
C17'—C16'—H6B'	108.7	C4—Re2—C5	85.5 (2)
S1'—C16'—H6B'	108.7	C4—Re2—C6	88.8 (2)
H6A'—C16'—H6B'	107.6	C5—Re2—C6	88.0 (2)
C16—C17—S2	111.6 (3)	C4—Re2—S2	177.67 (16)
C16—C17—H17A	109.3	C5—Re2—S2	95.21 (14)
S2—C17—H17A	109.3	C6—Re2—S2	93.43 (15)
C16—C17—H17B	109.3	C4—Re2—S1	93.58 (16)
S2—C17—H17B	109.3	C5—Re2—S1	98.74 (14)
H17A—C17—H17B	108.0	C6—Re2—S1	173.02 (15)
C16'—C17'—S2'	115.4 (3)	S2—Re2—S1	84.11 (4)
C16'—C17'—H7A'	108.4	C4—Re2—S3	95.69 (16)
S2'—C17'—H7A'	108.4	C5—Re2—S3	178.80 (14)
C16'—C17'—H7B'	108.4	C6—Re2—S3	91.80 (15)
S2'—C17'—H7B'	108.4	S2—Re2—S3	83.63 (4)
H7A'—C17'—H7B'	107.5	S1—Re2—S3	81.45 (4)
C19—C18—S2	115.7 (3)	C5'—Re2'—C6'	88.0 (2)
C19—C18—H18A	108.4	C5'—Re2'—C4'	84.3 (2)
S2—C18—H18A	108.4	C6'—Re2'—C4'	87.3 (2)
C19—C18—H18B	108.4	C5'—Re2'—S2'	93.12 (14)
S2—C18—H18B	108.4	C6'—Re2'—S2'	94.54 (14)
H18A—C18—H18B	107.4	C4'—Re2'—S2'	176.83 (15)
C19'—C18'—S2'	111.8 (3)	C5'—Re2'—S3'	177.69 (14)
C19'—C18'—H8A'	109.3	C6'—Re2'—S3'	93.76 (15)
S2'—C18'—H8A'	109.3	C4'—Re2'—S3'	97.20 (15)
C19'—C18'—H8B'	109.3	S2'—Re2'—S3'	85.30 (4)
S2'—C18'—H8B'	109.3	C5'—Re2'—S1'	96.82 (15)
H8A'—C18'—H8B'	107.9	C6'—Re2'—S1'	174.62 (14)
C18'—C19'—S3'	115.6 (3)	C4'—Re2'—S1'	95.49 (15)
C18'—C19'—H9A'	108.4	S2'—Re2'—S1'	82.93 (4)
S3'—C19'—H9A'	108.4	S3'—Re2'—S1'	81.33 (4)
C18'—C19'—H9B'	108.4	C15'—N1'—C11'	116.9 (4)
S3'—C19'—H9B'	108.4	C15'—N1'—Re1'	122.5 (3)
H9A'—C19'—H9B'	107.4	C11'—N1'—Re1'	120.5 (3)
C18—C19—S3	116.0 (3)	C15—N1—C11	117.6 (4)
C18—C19—H19A	108.3	C15—N1—Re1	120.9 (3)
S3—C19—H19A	108.3	C11—N1—Re1	121.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13′—H13′···O4′^i	0.95	2.46	3.260 (6)	142
C18—H18A···O1′^ii	0.99	2.40	3.327 (6)	156
C13—H13···O4^iii	0.95	2.34	3.275 (6)	168
C16—H16A···O5′^iv	0.99	2.38	3.278 (6)	150
C17′—H7B′···O5^iv	0.99	2.51	3.390 (6)	148
C19′—H9B′···O1^v	0.99	2.58	3.456 (7)	147

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

Tetraethylammonium fac-tris(µ-2-methoxybenzenethiolato-κ²S:S)bis[tricarbonylrhenium(I)] (14cpn4_0ma)

Crystal data

(C8H20N)[Re2(C7H7OS)3(CO)6]	F(000) = 2112
Mr = 1088.27	Dx = 1.833 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 12.7120 (5) Å	Cell parameters from 9974 reflections
b = 17.1050 (6) Å	θ = 2.3–26.0°
c = 18.144 (1) Å	µ = 6.34 mm^−1
β = 91.470 (2)°	T = 100 K
V = 3943.9 (3) Å^3	Cuboid, colourless
Z = 4	0.30 × 0.17 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	8238 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.085
φ and ω scans	θmax = 28.3°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
Tmin = 0.294, Tmax = 0.455	k = −22→22
36944 measured reflections	l = −23→24
9829 independent reflections

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)] = 0.033	w = 1/[σ^2(Fo^2)] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.068	(Δ/σ)max = 0.002
S = 0.92	Δρmax = 0.87 e Å^−3
9551 reflections	Δρmin = −0.95 e Å^−3
491 parameters	Absolute structure: Flack x determined using 3336 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraints	Absolute structure parameter: 0.005 (7)

Special details

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.

Refinement. A Bruker X8 APEXII 4K diffractometer equipped with graphite monochromated Mo Kα radiation with a wavelength of λ = 0.71073 Å and ω- and φ-scans at 100 K was used to collect the reflection data of all the structures reported here. The SIR-97 (Altomare et al., 1999) package was used to solve all structures while it was refined with WinGX (Farrugia, 1999) and SHELXL-97 (Sheldrick, 2008). The cell refinement was done with SAINT-Plus and the data reduction with SAINT-plus and XPREP (Bruker, 2008). The SADABS (Bruker, 2008) software package with the multi-scan technique was used to obtain absorption corrections, while the molecular graphics and presentation was done with Diamond (Brandenburg & Putz, 2005). All structures are drawn with thermal ellipsoids at a 50 % probability level. All non-hydrogen atoms were anisotropically refined.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Re1	0.17980 (2)	0.18897 (2)	0.77563 (2)	0.03475 (9)
Re2	0.17445 (3)	0.28352 (2)	0.94581 (2)	0.03561 (9)
S1	0.25682 (17)	0.31485 (12)	0.82369 (13)	0.0359 (5)
S2	0.23673 (17)	0.15194 (13)	0.90423 (14)	0.0388 (5)
S3	0.03389 (17)	0.24277 (13)	0.85401 (13)	0.0343 (5)
C1	0.1138 (9)	0.0911 (6)	0.7538 (6)	0.054 (3)
C3	0.1141 (8)	0.2301 (6)	0.6874 (6)	0.048 (2)
C2	0.2954 (9)	0.1570 (6)	0.7194 (6)	0.051 (2)
C4	0.1054 (9)	0.3778 (6)	0.9712 (6)	0.056 (3)
C5	0.1298 (8)	0.2424 (6)	1.0381 (6)	0.052 (3)
C6	0.3011 (9)	0.3186 (6)	0.9936 (6)	0.056 (3)
C10	0.1984 (7)	0.3903 (4)	0.7687 (5)	0.035 (2)
C15	0.2449 (8)	0.4088 (6)	0.7023 (6)	0.049 (2)
C20	0.3744 (7)	0.1425 (5)	0.9249 (6)	0.042 (2)
C25	0.4034 (8)	0.1264 (6)	0.9977 (6)	0.053 (3)
C30	−0.0438 (6)	0.1595 (5)	0.8762 (5)	0.037 (2)
C35	−0.1232 (7)	0.1390 (5)	0.8228 (6)	0.044 (2)
O1	0.0755 (8)	0.0327 (5)	0.7403 (5)	0.077 (3)
O2	0.3639 (7)	0.1356 (6)	0.6832 (5)	0.090 (3)
O3	0.0749 (7)	0.2540 (5)	0.6352 (4)	0.075 (2)
O4	0.0593 (9)	0.4321 (5)	0.9890 (6)	0.096 (3)
O5	0.1064 (8)	0.2197 (6)	1.0945 (5)	0.083 (3)
O6	0.3781 (7)	0.3410 (6)	1.0210 (5)	0.089 (3)
O15	0.3344 (7)	0.3674 (5)	0.6878 (5)	0.086 (3)
O25	0.3249 (6)	0.1220 (5)	1.0468 (5)	0.071 (2)
O35	−0.1334 (6)	0.1889 (4)	0.7635 (5)	0.066 (2)
C34	−0.1824 (8)	0.0720 (6)	0.8320 (6)	0.050 (2)
H34	−0.2344	0.0578	0.7959	0.060*
C23	0.5824 (9)	0.1160 (6)	0.9637 (8)	0.064 (3)
H23	0.6540	0.1057	0.9765	0.077*
C31	−0.0290 (7)	0.1126 (5)	0.9357 (6)	0.045 (2)
H31	0.0242	0.1254	0.9715	0.054*
C22	0.5548 (9)	0.1326 (7)	0.8914 (8)	0.062 (3)
H22	0.6068	0.1346	0.8547	0.074*
C24	0.5095 (9)	0.1140 (6)	1.0173 (8)	0.065 (3)
H24	0.5301	0.1043	1.0672	0.079*
C32	−0.0900 (8)	0.0457 (5)	0.9458 (6)	0.051 (3)
H32	−0.0792	0.0142	0.9884	0.061*
C33	−0.1659 (8)	0.0256 (6)	0.8938 (6)	0.054 (3)
H33	−0.2071	−0.0202	0.9002	0.064*
C14	0.2028 (9)	0.4659 (6)	0.6575 (6)	0.054 (3)
H14	0.2356	0.4778	0.6124	0.065*
C13	0.1133 (9)	0.5066 (6)	0.6767 (6)	0.055 (3)
H13	0.0861	0.5469	0.6456	0.066*
C12	0.0640 (8)	0.4883 (6)	0.7413 (7)	0.052 (3)
H12	0.0014	0.5148	0.7542	0.062*
C11	0.1066 (7)	0.4306 (5)	0.7877 (6)	0.042 (2)
H11	0.0731	0.4185	0.8325	0.051*
C21	0.4496 (8)	0.1463 (6)	0.8733 (7)	0.056 (3)
H21	0.4299	0.1587	0.8238	0.068*
C26	0.3496 (13)	0.1048 (10)	1.1216 (8)	0.108 (6)
H26C	0.4058	0.1397	1.1396	0.162*
H26A	0.3731	0.0504	1.1259	0.162*
H26B	0.2869	0.1124	1.1512	0.162*
C16	0.4041 (11)	0.3961 (10)	0.6391 (10)	0.111 (6)
H16C	0.3707	0.3985	0.5899	0.167*
H16A	0.4658	0.3617	0.6379	0.167*
H16B	0.4262	0.4486	0.6544	0.167*
C36	−0.1978 (13)	0.1653 (8)	0.7022 (8)	0.091 (5)
H36A	−0.1714	0.1159	0.6825	0.137*
H36C	−0.1960	0.2056	0.6638	0.137*
H36B	−0.2703	0.1583	0.7179	0.137*
N1	−0.2877 (7)	0.3746 (5)	0.9303 (6)	0.055 (2)
C11A	−0.2660 (17)	0.4503 (11)	0.8931 (15)	0.070 (7)	0.571 (9)
H11A	−0.2400	0.4882	0.9305	0.084*	0.571 (9)
H11B	−0.3328	0.4710	0.8717	0.084*	0.571 (9)
C21A	−0.3763 (16)	0.3769 (14)	0.9777 (13)	0.070 (6)	0.571 (9)
H21A	−0.3892	0.3243	0.9983	0.084*	0.571 (9)
H21B	−0.4401	0.3935	0.9495	0.084*	0.571 (9)
C31B	−0.310 (3)	0.3090 (13)	0.8726 (17)	0.099 (10)	0.571 (9)
H31A	−0.3248	0.2588	0.8975	0.119*	0.571 (9)
H31B	−0.2488	0.3018	0.8406	0.119*	0.571 (9)
C41B	−0.1842 (14)	0.3478 (12)	0.9707 (14)	0.069 (6)	0.571 (9)
H41A	−0.1592	0.3896	1.0046	0.082*	0.571 (9)
H41B	−0.1291	0.3386	0.9341	0.082*	0.571 (9)
C01A	−0.1863 (12)	0.4448 (9)	0.8324 (10)	0.104 (6)	0.571 (9)
H01A	−0.1761	0.4966	0.8107	0.156*	0.571 (9)
H01B	−0.1191	0.4257	0.8532	0.156*	0.571 (9)
H01C	−0.2121	0.4085	0.7943	0.156*	0.571 (9)
C02A	−0.3503 (14)	0.4403 (11)	1.0461 (8)	0.119 (7)	0.571 (9)
H02A	−0.4102	0.4425	1.0790	0.179*	0.571 (9)
H02B	−0.2874	0.4233	1.0740	0.179*	0.571 (9)
H02C	−0.3380	0.4923	1.0253	0.179*	0.571 (9)
C03A	−0.4156 (19)	0.3389 (13)	0.8227 (12)	0.154 (10)	0.571 (9)
H03A	−0.4334	0.2996	0.7852	0.230*	0.571 (9)
H03B	−0.4752	0.3459	0.8553	0.230*	0.571 (9)
H03C	−0.3996	0.3887	0.7987	0.230*	0.571 (9)
C04A	−0.2028 (16)	0.2713 (9)	1.0153 (10)	0.109 (6)	0.571 (9)
H04A	−0.1369	0.2555	1.0403	0.164*	0.571 (9)
H04B	−0.2566	0.2807	1.0520	0.164*	0.571 (9)
H04C	−0.2265	0.2298	0.9816	0.164*	0.571 (9)
C11B	−0.205 (2)	0.3686 (19)	0.8773 (17)	0.072 (8)	0.429 (9)
H11C	−0.2220	0.3257	0.8425	0.086*	0.429 (9)
H11D	−0.1383	0.3545	0.9038	0.086*	0.429 (9)
C21B	−0.261 (2)	0.4411 (17)	0.9863 (17)	0.070 (8)	0.429 (9)
H21C	−0.2598	0.4923	0.9609	0.084*	0.429 (9)
H21D	−0.1913	0.4320	1.0102	0.084*	0.429 (9)
C31A	−0.396 (2)	0.399 (2)	0.8923 (18)	0.075 (9)	0.429 (9)
H31C	−0.3921	0.4540	0.8744	0.090*	0.429 (9)
H31D	−0.4535	0.3952	0.9276	0.090*	0.429 (9)
C41A	−0.309 (3)	0.3024 (17)	0.969 (2)	0.085 (11)	0.429 (9)
H41C	−0.3319	0.2618	0.9338	0.102*	0.429 (9)
H41D	−0.3660	0.3111	1.0043	0.102*	0.429 (9)
C01B	−0.1863 (12)	0.4448 (9)	0.8324 (10)	0.104 (6)	0.429 (9)
H01D	−0.1293	0.4363	0.7980	0.156*	0.429 (9)
H01E	−0.2509	0.4586	0.8048	0.156*	0.429 (9)
H01F	−0.1671	0.4874	0.8663	0.156*	0.429 (9)
C02B	−0.3503 (14)	0.4403 (11)	1.0461 (8)	0.119 (7)	0.429 (9)
H02D	−0.3362	0.4816	1.0825	0.179*	0.429 (9)
H02E	−0.4189	0.4495	1.0218	0.179*	0.429 (9)
H02F	−0.3507	0.3894	1.0709	0.179*	0.429 (9)
C03B	−0.4156 (19)	0.3389 (13)	0.8227 (12)	0.154 (10)	0.429 (9)
H03D	−0.4821	0.3520	0.7972	0.230*	0.429 (9)
H03E	−0.3577	0.3436	0.7884	0.230*	0.429 (9)
H03F	−0.4188	0.2852	0.8413	0.230*	0.429 (9)
C04B	−0.2028 (16)	0.2713 (9)	1.0153 (10)	0.109 (6)	0.429 (9)
H04D	−0.2192	0.2227	1.0411	0.164*	0.429 (9)
H04E	−0.1462	0.2618	0.9808	0.164*	0.429 (9)
H04F	−0.1802	0.3111	1.0513	0.164*	0.429 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.03871 (18)	0.03216 (17)	0.03318 (19)	0.00115 (15)	−0.00323 (14)	−0.00123 (15)
Re2	0.03879 (18)	0.03445 (18)	0.03342 (19)	−0.00915 (16)	−0.00252 (14)	−0.00210 (16)
S1	0.0352 (11)	0.0349 (11)	0.0376 (13)	−0.0053 (9)	−0.0012 (9)	0.0031 (9)
S2	0.0383 (11)	0.0362 (12)	0.0415 (13)	−0.0017 (9)	−0.0074 (10)	0.0040 (10)
S3	0.0337 (11)	0.0319 (11)	0.0370 (12)	−0.0049 (9)	−0.0044 (9)	−0.0022 (9)
C1	0.072 (7)	0.049 (6)	0.042 (6)	−0.002 (5)	−0.007 (5)	−0.001 (5)
C3	0.055 (6)	0.050 (6)	0.039 (6)	0.006 (5)	−0.006 (5)	−0.005 (4)
C2	0.060 (6)	0.060 (6)	0.032 (6)	0.008 (5)	−0.005 (5)	−0.004 (5)
C4	0.079 (8)	0.054 (6)	0.034 (6)	0.002 (6)	0.008 (5)	−0.008 (5)
C5	0.055 (6)	0.055 (6)	0.047 (7)	−0.016 (5)	−0.003 (5)	−0.005 (5)
C6	0.056 (6)	0.067 (7)	0.043 (6)	−0.022 (5)	−0.003 (5)	0.009 (5)
C10	0.043 (5)	0.026 (4)	0.036 (5)	−0.003 (4)	−0.006 (4)	−0.003 (4)
C15	0.063 (6)	0.040 (5)	0.043 (6)	−0.003 (5)	0.013 (5)	−0.004 (4)
C20	0.038 (5)	0.035 (5)	0.052 (6)	0.002 (4)	−0.008 (4)	−0.004 (4)
C25	0.056 (6)	0.045 (6)	0.056 (7)	0.006 (5)	−0.019 (5)	0.010 (5)
C30	0.032 (4)	0.033 (4)	0.047 (6)	−0.007 (4)	−0.001 (4)	−0.003 (4)
C35	0.036 (5)	0.045 (5)	0.050 (6)	−0.005 (4)	−0.003 (4)	−0.003 (4)
O1	0.109 (7)	0.045 (5)	0.078 (6)	−0.019 (4)	−0.014 (5)	−0.014 (4)
O2	0.077 (6)	0.133 (9)	0.059 (6)	0.043 (6)	0.014 (5)	−0.008 (5)
O3	0.097 (7)	0.081 (6)	0.045 (5)	0.023 (5)	−0.016 (5)	0.007 (4)
O4	0.145 (9)	0.062 (6)	0.083 (7)	0.020 (6)	0.025 (7)	−0.014 (5)
O5	0.099 (7)	0.099 (7)	0.050 (6)	−0.040 (6)	0.003 (5)	0.017 (5)
O6	0.071 (6)	0.128 (8)	0.065 (6)	−0.052 (5)	−0.022 (5)	0.000 (5)
O15	0.099 (6)	0.074 (6)	0.088 (7)	0.026 (5)	0.055 (6)	0.027 (5)
O25	0.065 (5)	0.098 (6)	0.050 (5)	0.008 (4)	−0.010 (4)	0.029 (4)
O35	0.070 (5)	0.064 (5)	0.061 (5)	−0.028 (4)	−0.025 (4)	0.008 (4)
C34	0.045 (5)	0.045 (5)	0.060 (7)	−0.013 (4)	−0.008 (5)	−0.007 (5)
C23	0.045 (6)	0.052 (7)	0.094 (10)	0.013 (5)	−0.027 (7)	−0.009 (6)
C31	0.041 (5)	0.042 (5)	0.052 (6)	−0.010 (4)	−0.003 (4)	−0.003 (4)
C22	0.043 (6)	0.056 (7)	0.086 (10)	0.000 (5)	−0.003 (6)	−0.014 (6)
C24	0.069 (8)	0.050 (6)	0.076 (9)	0.017 (5)	−0.034 (7)	−0.002 (6)
C32	0.055 (6)	0.039 (5)	0.058 (7)	−0.011 (4)	0.005 (5)	0.003 (5)
C33	0.051 (6)	0.051 (6)	0.059 (7)	−0.019 (5)	0.005 (5)	−0.003 (5)
C14	0.082 (8)	0.046 (6)	0.033 (6)	−0.012 (5)	0.006 (5)	−0.001 (4)
C13	0.061 (7)	0.046 (6)	0.056 (7)	−0.011 (5)	−0.017 (6)	0.010 (5)
C12	0.038 (5)	0.045 (6)	0.072 (8)	−0.005 (4)	−0.012 (5)	−0.002 (5)
C11	0.040 (5)	0.043 (5)	0.044 (6)	−0.003 (4)	−0.005 (4)	0.000 (4)
C21	0.045 (6)	0.065 (7)	0.059 (7)	0.001 (5)	−0.010 (5)	−0.006 (5)
C26	0.104 (11)	0.151 (16)	0.066 (10)	0.001 (11)	−0.031 (9)	0.032 (10)
C16	0.079 (10)	0.116 (13)	0.141 (17)	0.015 (9)	0.044 (10)	0.012 (11)
C36	0.128 (13)	0.080 (9)	0.064 (9)	−0.042 (9)	−0.047 (9)	0.016 (7)
N1	0.053 (5)	0.048 (5)	0.067 (6)	0.001 (4)	0.008 (5)	0.009 (4)
C11A	0.060 (12)	0.045 (11)	0.10 (2)	0.000 (9)	0.017 (13)	0.022 (11)
C21A	0.055 (12)	0.070 (14)	0.084 (17)	0.019 (10)	0.011 (11)	0.012 (12)
C31B	0.14 (3)	0.041 (12)	0.12 (3)	−0.027 (13)	0.00 (2)	−0.011 (13)
C41B	0.040 (10)	0.071 (14)	0.095 (18)	0.019 (9)	0.005 (10)	−0.001 (12)
C01A	0.092 (11)	0.113 (13)	0.109 (14)	−0.002 (9)	0.031 (10)	0.041 (10)
C02A	0.146 (16)	0.159 (17)	0.054 (9)	0.075 (13)	0.034 (10)	0.007 (9)
C03A	0.20 (2)	0.138 (17)	0.119 (17)	−0.077 (16)	−0.090 (17)	0.043 (13)
C04A	0.156 (17)	0.077 (10)	0.095 (13)	0.044 (10)	−0.006 (12)	0.015 (9)
C11B	0.062 (17)	0.09 (2)	0.06 (2)	0.004 (15)	−0.002 (14)	−0.007 (16)
C21B	0.08 (2)	0.066 (18)	0.06 (2)	−0.004 (15)	−0.013 (16)	0.005 (15)
C31A	0.050 (15)	0.10 (2)	0.07 (2)	0.005 (16)	0.009 (14)	0.029 (18)
C41A	0.11 (3)	0.056 (18)	0.08 (3)	−0.021 (18)	−0.03 (2)	0.001 (15)
C01B	0.092 (11)	0.113 (13)	0.109 (14)	−0.002 (9)	0.031 (10)	0.041 (10)
C02B	0.146 (16)	0.159 (17)	0.054 (9)	0.075 (13)	0.034 (10)	0.007 (9)
C03B	0.20 (2)	0.138 (17)	0.119 (17)	−0.077 (16)	−0.090 (17)	0.043 (13)
C04B	0.156 (17)	0.077 (10)	0.095 (13)	0.044 (10)	−0.006 (12)	0.015 (9)

Geometric parameters (Å, º)

Re1—C2	1.891 (11)	C16—H16A	0.9800
Re1—C1	1.910 (11)	C16—H16B	0.9800
Re1—C3	1.920 (10)	C36—H36A	0.9800
Re1—S2	2.507 (2)	C36—H36C	0.9800
Re1—S1	2.512 (2)	C36—H36B	0.9800
Re1—S3	2.539 (2)	N1—C21A	1.44 (2)
Re2—C4	1.897 (11)	N1—C11B	1.45 (3)
Re2—C6	1.906 (11)	N1—C41A	1.45 (3)
Re2—C5	1.916 (12)	N1—C11A	1.49 (2)
Re2—S2	2.508 (2)	N1—C31B	1.56 (3)
Re2—S3	2.510 (2)	N1—C21B	1.56 (3)
Re2—S1	2.532 (2)	N1—C41B	1.56 (2)
S1—C10	1.782 (9)	N1—C31A	1.58 (3)
S2—C20	1.787 (9)	C11A—C01A	1.52 (3)
S3—C30	1.785 (9)	C11A—H11A	0.9900
C1—O1	1.136 (12)	C11A—H11B	0.9900
C3—O3	1.135 (12)	C21A—C02A	1.67 (3)
C2—O2	1.163 (12)	C21A—H21A	0.9900
C4—O4	1.150 (13)	C21A—H21B	0.9900
C5—O5	1.141 (13)	C31B—C03A	1.68 (4)
C6—O6	1.151 (12)	C31B—H31A	0.9900
C10—C15	1.391 (13)	C31B—H31B	0.9900
C10—C11	1.407 (12)	C41B—C04A	1.56 (3)
C15—C14	1.371 (14)	C41B—H41A	0.9900
C15—O15	1.373 (13)	C41B—H41B	0.9900
C20—C21	1.356 (15)	C01A—H01A	0.9800
C20—C25	1.390 (13)	C01A—H01B	0.9800
C25—O25	1.357 (14)	C01A—H01C	0.9800
C25—C24	1.402 (14)	C02A—H02A	0.9800
C30—C31	1.356 (13)	C02A—H02B	0.9800
C30—C35	1.425 (12)	C02A—H02C	0.9800
C35—O35	1.376 (12)	C03A—H03A	0.9800
C35—C34	1.384 (13)	C03A—H03B	0.9800
O15—C16	1.359 (15)	C03A—H03C	0.9800
O25—C26	1.416 (14)	C04A—H04A	0.9800
O35—C36	1.423 (13)	C04A—H04B	0.9800
C34—C33	1.384 (14)	C04A—H04C	0.9800
C34—H34	0.9500	C11B—C01B	1.56 (3)
C23—C24	1.361 (18)	C11B—H11C	0.9900
C23—C22	1.378 (17)	C11B—H11D	0.9900
C23—H23	0.9500	C21B—C02B	1.59 (3)
C31—C32	1.396 (12)	C21B—H21C	0.9900
C31—H31	0.9500	C21B—H21D	0.9900
C22—C21	1.390 (14)	C31A—C03B	1.65 (4)
C22—H22	0.9500	C31A—H31C	0.9900
C24—H24	0.9500	C31A—H31D	0.9900
C32—C33	1.376 (14)	C41A—C04B	1.65 (4)
C32—H32	0.9500	C41A—H41C	0.9900
C33—H33	0.9500	C41A—H41D	0.9900
C14—C13	1.386 (15)	C01B—H01D	0.9800
C14—H14	0.9500	C01B—H01E	0.9800
C13—C12	1.379 (16)	C01B—H01F	0.9800
C13—H13	0.9500	C02B—H02D	0.9800
C12—C11	1.397 (13)	C02B—H02E	0.9800
C12—H12	0.9500	C02B—H02F	0.9800
C11—H11	0.9500	C03B—H03D	0.9800
C21—H21	0.9500	C03B—H03E	0.9800
C26—H26C	0.9800	C03B—H03F	0.9800
C26—H26A	0.9800	C04B—H04D	0.9800
C26—H26B	0.9800	C04B—H04E	0.9800
C16—H16C	0.9800	C04B—H04F	0.9800
C2—Re1—C1	88.7 (5)	O35—C36—H36A	109.5
C2—Re1—C3	89.0 (4)	O35—C36—H36C	109.5
C1—Re1—C3	88.2 (4)	H36A—C36—H36C	109.5
C2—Re1—S2	102.7 (3)	O35—C36—H36B	109.5
C1—Re1—S2	94.9 (3)	H36A—C36—H36B	109.5
C3—Re1—S2	167.9 (3)	H36C—C36—H36B	109.5
C2—Re1—S1	97.7 (3)	C11B—N1—C41A	114 (2)
C1—Re1—S1	171.3 (3)	C21A—N1—C11A	113.9 (14)
C3—Re1—S1	97.6 (3)	C21A—N1—C31B	106.9 (16)
S2—Re1—S1	78.04 (7)	C11A—N1—C31B	110.8 (16)
C2—Re1—S3	174.9 (3)	C11B—N1—C21B	109.6 (18)
C1—Re1—S3	96.3 (4)	C41A—N1—C21B	109.9 (19)
C3—Re1—S3	91.5 (3)	C21A—N1—C41B	113.1 (14)
S2—Re1—S3	76.57 (7)	C11A—N1—C41B	107.7 (14)
S1—Re1—S3	77.21 (7)	C31B—N1—C41B	104.0 (15)
C4—Re2—C6	90.7 (5)	C11B—N1—C31A	111.7 (18)
C4—Re2—C5	87.2 (5)	C41A—N1—C31A	106.0 (19)
C6—Re2—C5	89.1 (4)	C21B—N1—C31A	105.1 (18)
C4—Re2—S2	170.6 (4)	N1—C11A—C01A	114.2 (15)
C6—Re2—S2	98.6 (4)	N1—C11A—H11A	108.7
C5—Re2—S2	92.1 (3)	C01A—C11A—H11A	108.7
C4—Re2—S3	94.1 (3)	N1—C11A—H11B	108.7
C6—Re2—S3	165.5 (3)	C01A—C11A—H11B	108.7
C5—Re2—S3	104.8 (3)	H11A—C11A—H11B	107.6
S2—Re2—S3	77.06 (7)	N1—C21A—C02A	108.6 (15)
C4—Re2—S1	103.7 (3)	N1—C21A—H21A	110.0
C6—Re2—S1	88.2 (3)	C02A—C21A—H21A	110.0
C5—Re2—S1	168.8 (3)	N1—C21A—H21B	110.0
S2—Re2—S1	77.64 (8)	C02A—C21A—H21B	110.0
S3—Re2—S1	77.38 (7)	H21A—C21A—H21B	108.3
C10—S1—Re1	105.9 (3)	N1—C31B—C03A	105.8 (18)
C10—S1—Re2	117.9 (3)	N1—C31B—H31A	110.6
Re1—S1—Re2	87.48 (7)	C03A—C31B—H31A	110.6
C20—S2—Re1	118.4 (4)	N1—C31B—H31B	110.6
C20—S2—Re2	109.5 (3)	C03A—C31B—H31B	110.6
Re1—S2—Re2	88.14 (7)	H31A—C31B—H31B	108.7
C30—S3—Re2	117.4 (3)	N1—C41B—C04A	110.7 (15)
C30—S3—Re1	104.7 (3)	N1—C41B—H41A	109.5
Re2—S3—Re1	87.39 (7)	C04A—C41B—H41A	109.5
O1—C1—Re1	179.2 (11)	N1—C41B—H41B	109.5
O3—C3—Re1	179.5 (11)	C04A—C41B—H41B	109.5
O2—C2—Re1	177.5 (10)	H41A—C41B—H41B	108.1
O4—C4—Re2	175.7 (11)	C11A—C01A—H01A	109.5
O5—C5—Re2	177.1 (9)	C11A—C01A—H01B	109.5
O6—C6—Re2	178.3 (10)	H01A—C01A—H01B	109.5
C15—C10—C11	118.3 (9)	C11A—C01A—H01C	109.5
C15—C10—S1	118.0 (7)	H01A—C01A—H01C	109.5
C11—C10—S1	123.6 (7)	H01B—C01A—H01C	109.5
C14—C15—O15	124.6 (10)	C21A—C02A—H02A	109.5
C14—C15—C10	120.5 (9)	C21A—C02A—H02B	109.5
O15—C15—C10	114.9 (9)	H02A—C02A—H02B	109.5
C21—C20—C25	119.4 (9)	C21A—C02A—H02C	109.5
C21—C20—S2	123.6 (8)	H02A—C02A—H02C	109.5
C25—C20—S2	116.9 (8)	H02B—C02A—H02C	109.5
O25—C25—C20	116.9 (8)	C31B—C03A—H03A	109.5
O25—C25—C24	123.0 (11)	C31B—C03A—H03B	109.5
C20—C25—C24	120.1 (11)	H03A—C03A—H03B	109.5
C31—C30—C35	118.6 (8)	C31B—C03A—H03C	109.5
C31—C30—S3	125.9 (7)	H03A—C03A—H03C	109.5
C35—C30—S3	115.4 (7)	H03B—C03A—H03C	109.5
O35—C35—C34	124.6 (9)	C41B—C04A—H04A	109.5
O35—C35—C30	115.4 (8)	C41B—C04A—H04B	109.5
C34—C35—C30	119.9 (9)	H04A—C04A—H04B	109.5
C16—O15—C15	119.7 (10)	C41B—C04A—H04C	109.5
C25—O25—C26	119.5 (10)	H04A—C04A—H04C	109.5
C35—O35—C36	118.4 (8)	H04B—C04A—H04C	109.5
C35—C34—C33	120.1 (9)	N1—C11B—C01B	114 (2)
C35—C34—H34	119.9	N1—C11B—H11C	108.7
C33—C34—H34	119.9	C01B—C11B—H11C	108.7
C24—C23—C22	121.6 (10)	N1—C11B—H11D	108.7
C24—C23—H23	119.2	C01B—C11B—H11D	108.7
C22—C23—H23	119.2	H11C—C11B—H11D	107.6
C30—C31—C32	121.5 (9)	N1—C21B—C02B	107 (2)
C30—C31—H31	119.2	N1—C21B—H21C	110.3
C32—C31—H31	119.2	C02B—C21B—H21C	110.3
C23—C22—C21	118.7 (12)	N1—C21B—H21D	110.3
C23—C22—H22	120.7	C02B—C21B—H21D	110.3
C21—C22—H22	120.7	H21C—C21B—H21D	108.6
C23—C24—C25	118.9 (12)	N1—C31A—C03B	106 (2)
C23—C24—H24	120.5	N1—C31A—H31C	110.5
C25—C24—H24	120.5	C03B—C31A—H31C	110.5
C33—C32—C31	119.9 (10)	N1—C31A—H31D	110.5
C33—C32—H32	120.1	C03B—C31A—H31D	110.5
C31—C32—H32	120.1	H31C—C31A—H31D	108.7
C32—C33—C34	120.0 (9)	N1—C41A—C04B	111 (2)
C32—C33—H33	120.0	N1—C41A—H41C	109.4
C34—C33—H33	120.0	C04B—C41A—H41C	109.4
C15—C14—C13	121.2 (10)	N1—C41A—H41D	109.4
C15—C14—H14	119.4	C04B—C41A—H41D	109.4
C13—C14—H14	119.4	H41C—C41A—H41D	108.0
C12—C13—C14	119.6 (10)	C11B—C01B—H01D	109.5
C12—C13—H13	120.2	C11B—C01B—H01E	109.5
C14—C13—H13	120.2	H01D—C01B—H01E	109.5
C13—C12—C11	119.6 (10)	C11B—C01B—H01F	109.5
C13—C12—H12	120.2	H01D—C01B—H01F	109.5
C11—C12—H12	120.2	H01E—C01B—H01F	109.5
C12—C11—C10	120.7 (10)	C21B—C02B—H02D	109.5
C12—C11—H11	119.7	C21B—C02B—H02E	109.5
C10—C11—H11	119.7	H02D—C02B—H02E	109.5
C20—C21—C22	121.3 (11)	C21B—C02B—H02F	109.5
C20—C21—H21	119.3	H02D—C02B—H02F	109.5
C22—C21—H21	119.3	H02E—C02B—H02F	109.5
O25—C26—H26C	109.5	C31A—C03B—H03D	109.5
O25—C26—H26A	109.5	C31A—C03B—H03E	109.5
H26C—C26—H26A	109.5	H03D—C03B—H03E	109.5
O25—C26—H26B	109.5	C31A—C03B—H03F	109.5
H26C—C26—H26B	109.5	H03D—C03B—H03F	109.5
H26A—C26—H26B	109.5	H03E—C03B—H03F	109.5
O15—C16—H16C	109.5	C41A—C04B—H04D	109.5
O15—C16—H16A	109.5	C41A—C04B—H04E	109.5
H16C—C16—H16A	109.5	H04D—C04B—H04E	109.5
O15—C16—H16B	109.5	C41A—C04B—H04F	109.5
H16C—C16—H16B	109.5	H04D—C04B—H04F	109.5
H16A—C16—H16B	109.5	H04E—C04B—H04F	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11A—H11A···S2^i	0.99	2.86	3.45 (2)	120
C16—H16A···O5^ii	0.98	2.41	3.361 (17)	162

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