Tetrakis([mu]-benzothiazole-2-thiolato)-1:2[kappa]⁴N:S²;1:2[kappa]⁴S²:N-dichloro-1[kappa]Cl,2[kappa]Cl-dirhenium(III)(Re-Re) dichloromethane solvate: a bridged complex with a long Re-Re quadruple bond

The title compound, [Re₂(C₇H₄NS₂)₄Cl₂]·CH₂Cl₂, consists of dirhenium mol­ecules with bridging N,S-benzo­thia­zole-2-thiol­ate ligands, axial Cl^- ligands and intramolecular hydrogen bonding. These mol­ecules adopt somewhat staggered conformations, with a long Re-Re quadruple bond distance of 2.2716 (3) Å.

S1. Comment

In the major component, [Re₂(S₂NC₇H₄)₄Cl₂], of the title compound, (I), each one of the four benzothiazole-2-thiolate ligands bridges the dirhenium unit by binding through one S atom and the N atom, rather than through both S atoms. The preference of Re^III to form bonds to N rather than S has been previously documented by the discovery of N-bound thiocyanate ligands in the [Re₂(NCS)₈]^2- ion (Cotton et al., 1967). \sch

The four bridging ligands are arranged so that all N and S atoms are trans to each other. This leads to a cis arrangement of N and S atoms around each Re atom. Two axial Cl^- ligands and an Re—Re bond complete the coordination about the dirhenium unit, so that both metal atoms end up in essentially identical pseudo-octahedral environments.

Hydrogen bonding exists between the two Cl^- ligands and the H atoms at the 4-positions on two of the benzothiazole-2-thiolate ligands (Table 2). The Cl1—H24 and Cl2—H3 distances are 2.50 and 2.52 Å, respectively, and these are illustrated by dashed lines in Fig. 1. Apparently as a result of this hydrogen bonding, the Re—Re—Cl bond angles are bent away from linearity at 158.88 (3) and 159.85 (2)°.

As illustrated in Fig. 2, the molecule takes on a somewhat staggered conformation, with an average torsion angle about the dirhenium axis of 18 (1)°. This torsional twist is far greater than that in any of the compounds with bridging ligands listed in Cotton and Walton's compilation of structural data for compounds containing Re—Re quadruple bonds (Cotton & Walton, 1993). The Re—Re bond distance of 2.2716 (3) Å is also longer than that in any of the bridged compounds in Cotton and Walton's list. Twisting away from an eclipsed conformation is known to weaken the δ component of the quadruple bond (Campbell et al., 1985). However, another factor seems to be at work in (I).

A search of the Cambridge Structural Database (Version 5.22; Allen & Kennard, 1993) for structures published after Cotton and Walton's book went to press has yielded six molecules with Re—Re quadruple bonds longer than 2.25 Å. In each of these molecules, there is at least one bridging ligand. These bridging ligands are 2,6-bis(diphenylphosphino)pyridine (Cotton et al., 1998) and N,N'-diarylformamidinate, with aryl = p-tolyl (Cotton & Ren, 1992), and p-methoxyphenyl, 3,4-dichlorophenyl and 3,5-dichlorophenyl (Eglin et al., 1999). All torsion angles about the dirhenium units are less than 12°, but the Re—Re bond distances range from 2.270 to 2.304 Å. This elongation of the quadruple bonds has been attributed to the presence of axial Cl^- ligands (Cotton et al., 1998).

Molecules of (I) pack in a way that maximizes S—S interactions, as shown in Fig. 3. There are intermolecular contacts involving one Cl^- ligand (Cl2) and all S atoms, with the exception of S4. These nonbonding distances range from 3.467 to 3.626 Å.

S2. Experimental

All synthetic procedures were carried out under a nitrogen atmosphere. Hexachlorobis(methyldiphenylphosphino)dirhenium(III), Re₂Cl₆(PMePh₂)₂, (50.1 mg, 0.0508 mmol), 2,2'-dithiobis(benzothiazole) (33.8 mg, 0.102 mmol), and dichloromethane (15 ml) were combined in a 50 ml round-bottomed flask. The mixture was stirred at reflux for 3 h. The resulting deep-purple mixture was filtered through a medium glass frit. Slow evaporation of the filtrate yielded a dark solid. A small amount of this solid was dissolved in dichloromethane (5 ml) and layered with hexanes (20 ml). Thin purple crystals of (I) formed after one week NB red-brown given below. Analysis calculated for Re₂Cl₄S₈N₄C₂₉H₁₈: C 29.19, H 1.52, N 4.70%; found: C 28.54, H 1.66, N 4.79%. IR data (KBr, cm^-1): 1608 (w), 1465 (m), 1353 (m), 1322 (m), 1288 (w), 1253 (w), 1109 (m-s), 1100 (versus), 1047 (s), 1026 (w), 841 (m), 763 (s), 754 (versus). Visible maxima (nm) in CH₂Cl₂: 742, 620, 539, 427.

S3. Refinement

H atoms were treated as riding, with C—H = 0.94–0.98 Å and U_iso(H) = 1.2U_eq(C). Are these the correct constraints? The largest peak in the final difference map is located 0.97 Å from solvent atom Cl3.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii and the dichloromethane solvent molecule has been omitted.
	Fig. 2. The [Re2(NS2C7H4)4Cl2] molecule of (I) viewed directly down the Re—Re axis. All H atoms have been omitted for clarity.
	Fig. 3. A packing diagram for (I), showing some of the main S—S and S—Cl interactions.

Tetrakis(µ-benzothiazole-2-thiolato)-1:2κ⁴N:S²;1:2κ⁴S²:N- dichloro-1κCl,2κCl-dirhenium(III)(Re—Re) dichloromethane solvate

Crystal data

[Re2(S2NC7H4)4Cl2]·CH2Cl2	F(000) = 2264
Mr = 1193.15	Dx = 2.250 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.9408 (7) Å	Cell parameters from 9504 reflections
b = 15.5347 (8) Å	θ = 2.6–27.5°
c = 17.5303 (9) Å	µ = 7.68 mm^−1
β = 92.092 (1)°	T = 213 K
V = 3521.8 (3) Å^3	Plate, red-brown
Z = 4	0.38 × 0.16 × 0.02 mm

Data collection

Bruker SMART CCD area-detector diffractometer	8000 independent reflections
Radiation source: normal-focus sealed tube	6368 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: analytical face-indexed (XPREP in SHELXTL; Siemens, 1996)	h = −16→9
Tmin = 0.174, Tmax = 0.851	k = −20→18
21991 measured reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.051	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0185P)^2] where P = (Fo^2 + 2Fc^2)/3
8000 reflections	(Δ/σ)max = 0.002
424 parameters	Δρmax = 1.10 e Å^−3
0 restraints	Δρmin = −0.71 e Å^−3

Special details

Experimental. The first 50 frames were measured again at the end of the data collection procedure and used to evaluate any decay.

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 on 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 (Ų)

	x	y	z	Uiso*/Ueq
Re1	0.402035 (13)	0.233553 (9)	0.636027 (8)	0.02012 (5)
Re2	0.570330 (13)	0.275300 (9)	0.643519 (8)	0.01912 (4)
Cl1	0.24541 (9)	0.13696 (6)	0.61028 (6)	0.0319 (2)
Cl2	0.73142 (8)	0.36746 (6)	0.62748 (6)	0.0282 (2)
S1	0.43737 (9)	0.11491 (6)	0.71957 (6)	0.0258 (2)
S2	0.59375 (9)	0.08328 (6)	0.84479 (6)	0.0296 (2)
S3	0.44070 (9)	0.14991 (6)	0.52467 (6)	0.0290 (2)
S4	0.63252 (10)	0.07321 (7)	0.46228 (6)	0.0345 (3)
S5	0.53868 (9)	0.35918 (6)	0.53005 (6)	0.0278 (2)
S6	0.35311 (10)	0.42827 (7)	0.44396 (7)	0.0368 (3)
S7	0.53397 (9)	0.39333 (6)	0.72470 (6)	0.0249 (2)
S8	0.37442 (10)	0.42520 (7)	0.83724 (6)	0.0323 (3)
N1	0.6150 (3)	0.20433 (18)	0.74394 (17)	0.0213 (7)
N2	0.6347 (3)	0.17647 (19)	0.57844 (17)	0.0230 (7)
N3	0.3410 (3)	0.32880 (19)	0.56225 (18)	0.0241 (7)
N4	0.3526 (3)	0.30651 (19)	0.73294 (17)	0.0226 (7)
C1	0.5520 (3)	0.1392 (2)	0.7641 (2)	0.0220 (9)
C2	0.6958 (3)	0.2157 (2)	0.7992 (2)	0.0228 (9)
C3	0.7691 (3)	0.2815 (2)	0.8013 (2)	0.0281 (9)
H3	0.7705	0.3230	0.7624	0.034*
C4	0.8394 (4)	0.2838 (3)	0.8620 (2)	0.0309 (10)
H4	0.8896	0.3275	0.8638	0.037*
C5	0.8389 (4)	0.2239 (3)	0.9208 (2)	0.0333 (10)
H5	0.8877	0.2279	0.9617	0.040*
C6	0.7668 (3)	0.1585 (3)	0.9191 (2)	0.0292 (10)
H6	0.7660	0.1173	0.9584	0.035*
C7	0.6951 (3)	0.1550 (2)	0.8580 (2)	0.0257 (9)
C8	0.5709 (3)	0.1393 (2)	0.5259 (2)	0.0254 (9)
C9	0.7373 (4)	0.1496 (2)	0.5716 (2)	0.0265 (10)
C10	0.8222 (3)	0.1720 (2)	0.6190 (2)	0.0276 (9)
H10	0.8137	0.2078	0.6615	0.033*
C11	0.9184 (4)	0.1411 (3)	0.6024 (3)	0.0371 (11)
H11	0.9760	0.1556	0.6341	0.044*
C12	0.9313 (4)	0.0881 (3)	0.5386 (3)	0.0408 (12)
H12	0.9980	0.0694	0.5268	0.049*
C13	0.8478 (4)	0.0630 (3)	0.4930 (3)	0.0370 (11)
H13	0.8563	0.0261	0.4512	0.044*
C14	0.7503 (4)	0.0938 (2)	0.5103 (2)	0.0315 (10)
C15	0.4091 (3)	0.3668 (2)	0.5167 (2)	0.0263 (9)
C16	0.2380 (4)	0.3521 (2)	0.5418 (2)	0.0276 (10)
C17	0.1496 (4)	0.3292 (3)	0.5786 (2)	0.0299 (10)
H17	0.1536	0.2956	0.6233	0.036*
C18	0.0543 (4)	0.3569 (3)	0.5483 (3)	0.0363 (11)
H18	−0.0067	0.3411	0.5722	0.044*
C19	0.0486 (4)	0.4080 (3)	0.4825 (3)	0.0385 (12)
H19	−0.0164	0.4253	0.4623	0.046*
C20	0.1364 (4)	0.4333 (3)	0.4469 (3)	0.0358 (11)
H20	0.1322	0.4684	0.4033	0.043*
C21	0.2314 (4)	0.4058 (2)	0.4769 (2)	0.0300 (10)
C22	0.4167 (3)	0.3693 (2)	0.7587 (2)	0.0233 (9)
C23	0.2680 (3)	0.2982 (2)	0.7802 (2)	0.0231 (9)
C24	0.1899 (3)	0.2366 (2)	0.7754 (2)	0.0301 (10)
H24	0.1880	0.1956	0.7359	0.036*
C25	0.1154 (4)	0.2367 (3)	0.8297 (3)	0.0349 (11)
H25	0.0614	0.1963	0.8257	0.042*
C26	0.1175 (4)	0.2947 (3)	0.8899 (2)	0.0365 (11)
H26	0.0668	0.2918	0.9268	0.044*
C27	0.1936 (4)	0.3561 (3)	0.8958 (2)	0.0362 (11)
H27	0.1955	0.3960	0.9361	0.043*
C28	0.2680 (4)	0.3577 (2)	0.8400 (2)	0.0290 (10)
C29	0.9784 (7)	−0.0434 (4)	0.7540 (4)	0.108 (3)
H29A	0.9957	−0.0895	0.7905	0.130*
H29B	0.9433	−0.0700	0.7095	0.130*
Cl3	1.09014 (14)	0.00144 (9)	0.72557 (9)	0.0676 (4)
Cl4	0.89223 (15)	0.02667 (11)	0.79603 (9)	0.0812 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.02086 (10)	0.01914 (8)	0.02014 (8)	−0.00205 (7)	−0.00233 (6)	−0.00001 (6)
Re2	0.02018 (9)	0.01788 (7)	0.01915 (8)	−0.00070 (7)	−0.00144 (6)	0.00002 (6)
Cl1	0.0280 (6)	0.0331 (5)	0.0342 (6)	−0.0082 (5)	−0.0022 (5)	−0.0049 (4)
Cl2	0.0261 (6)	0.0293 (5)	0.0289 (5)	−0.0048 (4)	−0.0024 (4)	0.0049 (4)
S1	0.0285 (6)	0.0205 (5)	0.0279 (5)	−0.0049 (4)	−0.0047 (5)	0.0034 (4)
S2	0.0354 (7)	0.0283 (5)	0.0245 (5)	−0.0053 (5)	−0.0055 (5)	0.0070 (4)
S3	0.0300 (7)	0.0303 (5)	0.0264 (5)	−0.0040 (5)	−0.0011 (5)	−0.0074 (4)
S4	0.0402 (8)	0.0305 (5)	0.0331 (6)	0.0001 (5)	0.0050 (5)	−0.0130 (4)
S5	0.0262 (6)	0.0304 (5)	0.0266 (5)	−0.0038 (5)	−0.0031 (5)	0.0087 (4)
S6	0.0341 (7)	0.0362 (6)	0.0393 (6)	−0.0017 (5)	−0.0091 (5)	0.0166 (5)
S7	0.0244 (6)	0.0197 (4)	0.0306 (5)	−0.0026 (4)	0.0013 (5)	−0.0043 (4)
S8	0.0366 (7)	0.0319 (5)	0.0288 (6)	−0.0057 (5)	0.0065 (5)	−0.0091 (4)
N1	0.028 (2)	0.0186 (15)	0.0173 (16)	−0.0007 (14)	−0.0024 (14)	−0.0011 (12)
N2	0.027 (2)	0.0212 (16)	0.0207 (17)	0.0018 (15)	0.0004 (15)	0.0010 (13)
N3	0.023 (2)	0.0233 (16)	0.0255 (18)	−0.0031 (15)	−0.0052 (15)	−0.0016 (13)
N4	0.0210 (19)	0.0209 (15)	0.0257 (18)	0.0022 (14)	−0.0023 (15)	0.0025 (13)
C1	0.028 (2)	0.0202 (18)	0.0175 (19)	0.0016 (17)	−0.0027 (17)	−0.0005 (14)
C2	0.021 (2)	0.0275 (19)	0.0197 (19)	0.0017 (17)	0.0010 (17)	−0.0037 (15)
C3	0.026 (3)	0.030 (2)	0.028 (2)	−0.0002 (19)	0.0001 (19)	0.0021 (17)
C4	0.025 (3)	0.035 (2)	0.033 (2)	−0.005 (2)	−0.001 (2)	−0.0026 (18)
C5	0.028 (3)	0.044 (2)	0.027 (2)	0.002 (2)	−0.0113 (19)	−0.0024 (19)
C6	0.029 (3)	0.035 (2)	0.023 (2)	0.005 (2)	−0.0035 (19)	0.0023 (17)
C7	0.026 (2)	0.0252 (19)	0.026 (2)	−0.0009 (18)	0.0007 (18)	−0.0013 (16)
C8	0.034 (3)	0.0230 (19)	0.020 (2)	−0.0014 (18)	0.0047 (18)	−0.0018 (15)
C9	0.037 (3)	0.0205 (19)	0.023 (2)	0.0046 (19)	0.0066 (19)	0.0027 (15)
C10	0.030 (3)	0.028 (2)	0.025 (2)	0.0068 (19)	−0.0005 (19)	0.0025 (16)
C11	0.030 (3)	0.036 (2)	0.045 (3)	0.007 (2)	−0.002 (2)	0.002 (2)
C12	0.036 (3)	0.033 (2)	0.053 (3)	0.014 (2)	0.009 (2)	−0.001 (2)
C13	0.044 (3)	0.025 (2)	0.042 (3)	0.012 (2)	0.006 (2)	−0.0049 (18)
C14	0.041 (3)	0.0179 (19)	0.036 (2)	0.0042 (19)	0.004 (2)	−0.0011 (16)
C15	0.028 (3)	0.0234 (19)	0.026 (2)	−0.0006 (18)	−0.0074 (19)	0.0036 (16)
C16	0.028 (3)	0.0202 (19)	0.034 (2)	0.0033 (18)	−0.008 (2)	−0.0022 (16)
C17	0.029 (3)	0.033 (2)	0.027 (2)	0.005 (2)	−0.002 (2)	−0.0057 (17)
C18	0.029 (3)	0.038 (2)	0.042 (3)	0.002 (2)	0.000 (2)	−0.011 (2)
C19	0.033 (3)	0.028 (2)	0.053 (3)	0.009 (2)	−0.021 (2)	−0.008 (2)
C20	0.035 (3)	0.030 (2)	0.041 (3)	0.002 (2)	−0.013 (2)	0.0022 (19)
C21	0.036 (3)	0.0211 (19)	0.032 (2)	−0.0004 (19)	−0.007 (2)	−0.0004 (16)
C22	0.026 (2)	0.0219 (18)	0.022 (2)	0.0011 (18)	−0.0022 (18)	0.0015 (15)
C23	0.024 (2)	0.0231 (19)	0.022 (2)	0.0027 (17)	−0.0012 (17)	0.0027 (15)
C24	0.029 (3)	0.031 (2)	0.031 (2)	−0.003 (2)	0.0014 (19)	0.0039 (17)
C25	0.030 (3)	0.037 (2)	0.038 (3)	−0.003 (2)	0.003 (2)	0.0069 (19)
C26	0.031 (3)	0.049 (3)	0.030 (2)	0.002 (2)	0.011 (2)	0.002 (2)
C27	0.037 (3)	0.043 (3)	0.029 (2)	0.004 (2)	0.011 (2)	−0.0046 (19)
C28	0.032 (3)	0.031 (2)	0.024 (2)	−0.001 (2)	−0.0007 (19)	−0.0009 (17)
C29	0.168 (9)	0.057 (4)	0.105 (6)	−0.051 (5)	0.069 (6)	−0.042 (4)
Cl3	0.0685 (12)	0.0638 (9)	0.0700 (10)	0.0075 (8)	−0.0028 (8)	−0.0114 (7)
Cl4	0.0864 (14)	0.0901 (11)	0.0683 (11)	0.0118 (10)	0.0203 (10)	0.0025 (9)

Geometric parameters (Å, º)

Re1—N3	2.100 (3)	C5—H5	0.9400
Re1—N4	2.159 (3)	C6—C7	1.393 (6)
Re1—Re2	2.2716 (3)	C6—H6	0.9400
Re1—S1	2.3879 (9)	C9—C14	1.395 (5)
Re1—S3	2.4126 (10)	C9—C10	1.397 (6)
Re1—Cl1	2.5488 (11)	C10—C11	1.376 (6)
Re2—N2	2.103 (3)	C10—H10	0.9400
Re2—N1	2.139 (3)	C11—C12	1.405 (6)
Re2—S7	2.3786 (9)	C11—H11	0.9400
Re2—S5	2.4006 (10)	C12—C13	1.377 (7)
Re2—Cl2	2.5529 (10)	C12—H12	0.9400
S1—C1	1.694 (4)	C13—C14	1.392 (6)
S2—C1	1.729 (4)	C13—H13	0.9400
S2—C7	1.730 (4)	C16—C17	1.380 (6)
S3—C8	1.692 (5)	C16—C21	1.412 (5)
S4—C8	1.732 (4)	C17—C18	1.392 (6)
S4—C14	1.744 (5)	C17—H17	0.9400
S5—C15	1.689 (4)	C18—C19	1.401 (6)
S6—C15	1.731 (4)	C18—H18	0.9400
S6—C21	1.733 (5)	C19—C20	1.373 (6)
S7—C22	1.692 (4)	C19—H19	0.9400
S8—C22	1.733 (4)	C20—C21	1.387 (6)
S8—C28	1.733 (4)	C20—H20	0.9400
N1—C1	1.354 (5)	C23—C24	1.392 (6)
N1—C2	1.411 (5)	C23—C28	1.398 (5)
N2—C8	1.345 (5)	C24—C25	1.379 (6)
N2—C9	1.401 (5)	C24—H24	0.9400
N3—C15	1.346 (5)	C25—C26	1.387 (6)
N3—C16	1.415 (5)	C25—H25	0.9400
N4—C22	1.348 (5)	C26—C27	1.372 (6)
N4—C23	1.403 (5)	C26—H26	0.9400
C2—C3	1.394 (5)	C27—C28	1.397 (6)
C2—C7	1.398 (5)	C27—H27	0.9400
C3—C4	1.375 (6)	C29—Cl3	1.696 (7)
C3—H3	0.9400	C29—Cl4	1.742 (7)
C4—C5	1.388 (6)	C29—H29A	0.9800
C4—H4	0.9400	C29—H29B	0.9800
C5—C6	1.378 (6)
N3—Re1—N4	89.95 (12)	C2—C7—S2	111.2 (3)
N3—Re1—Re2	99.94 (9)	N2—C8—S3	123.6 (3)
N4—Re1—Re2	96.65 (9)	N2—C8—S4	114.2 (3)
N3—Re1—S1	168.74 (10)	S3—C8—S4	122.1 (2)
N4—Re1—S1	88.75 (8)	C14—C9—C10	119.9 (4)
Re2—Re1—S1	91.33 (3)	C14—C9—N2	113.2 (4)
N3—Re1—S3	88.03 (9)	C10—C9—N2	127.0 (4)
N4—Re1—S3	174.72 (9)	C11—C10—C9	119.1 (4)
Re2—Re1—S3	88.50 (3)	C11—C10—H10	120.5
S1—Re1—S3	92.28 (4)	C9—C10—H10	120.5
N3—Re1—Cl1	91.55 (9)	C10—C11—C12	120.5 (5)
N4—Re1—Cl1	101.05 (9)	C10—C11—H11	119.7
Re2—Re1—Cl1	158.88 (3)	C12—C11—H11	119.7
S1—Re1—Cl1	77.73 (4)	C13—C12—C11	120.9 (5)
S3—Re1—Cl1	74.14 (4)	C13—C12—H12	119.5
N2—Re2—N1	88.27 (11)	C11—C12—H12	119.5
N2—Re2—Re1	99.09 (9)	C12—C13—C14	118.4 (4)
N1—Re2—Re1	97.47 (9)	C12—C13—H13	120.8
N2—Re2—S7	168.07 (10)	C14—C13—H13	120.8
N1—Re2—S7	87.61 (8)	C13—C14—C9	121.2 (4)
Re1—Re2—S7	92.55 (3)	C13—C14—S4	127.9 (3)
N2—Re2—S5	90.33 (9)	C9—C14—S4	110.9 (3)
N1—Re2—S5	174.07 (10)	N3—C15—S5	123.7 (3)
Re1—Re2—S5	88.44 (3)	N3—C15—S6	114.4 (3)
S7—Re2—S5	92.63 (4)	S5—C15—S6	121.8 (2)
N2—Re2—Cl2	90.49 (9)	C17—C16—C21	120.2 (4)
N1—Re2—Cl2	100.53 (9)	C17—C16—N3	127.2 (4)
Re1—Re2—Cl2	159.85 (2)	C21—C16—N3	112.6 (4)
S7—Re2—Cl2	79.27 (3)	C16—C17—C18	118.6 (4)
S5—Re2—Cl2	73.72 (3)	C16—C17—H17	120.7
C1—S1—Re1	104.83 (13)	C18—C17—H17	120.7
C1—S2—C7	89.93 (19)	C17—C18—C19	120.6 (5)
C8—S3—Re1	106.14 (13)	C17—C18—H18	119.7
C8—S4—C14	89.7 (2)	C19—C18—H18	119.7
C15—S5—Re2	106.92 (14)	C20—C19—C18	121.1 (4)
C15—S6—C21	90.3 (2)	C20—C19—H19	119.4
C22—S7—Re2	103.92 (13)	C18—C19—H19	119.4
C22—S8—C28	89.63 (19)	C19—C20—C21	118.5 (4)
C1—N1—C2	110.6 (3)	C19—C20—H20	120.7
C1—N1—Re2	117.0 (3)	C21—C20—H20	120.7
C2—N1—Re2	132.2 (2)	C20—C21—C16	120.9 (4)
C8—N2—C9	111.9 (3)	C20—C21—S6	128.0 (3)
C8—N2—Re2	116.1 (3)	C16—C21—S6	111.0 (3)
C9—N2—Re2	131.3 (3)	N4—C22—S7	126.2 (3)
C15—N3—C16	111.6 (3)	N4—C22—S8	114.9 (3)
C15—N3—Re1	115.8 (3)	S7—C22—S8	118.9 (2)
C16—N3—Re1	131.7 (3)	C24—C23—C28	118.7 (4)
C22—N4—C23	110.7 (3)	C24—C23—N4	127.5 (4)
C22—N4—Re1	116.6 (3)	C28—C23—N4	113.8 (4)
C23—N4—Re1	132.6 (3)	C25—C24—C23	118.7 (4)
N1—C1—S1	124.8 (3)	C25—C24—H24	120.6
N1—C1—S2	114.6 (3)	C23—C24—H24	120.6
S1—C1—S2	120.5 (2)	C24—C25—C26	122.1 (4)
C3—C2—C7	119.9 (4)	C24—C25—H25	118.9
C3—C2—N1	126.7 (3)	C26—C25—H25	118.9
C7—C2—N1	113.4 (3)	C27—C26—C25	120.2 (4)
C4—C3—C2	118.0 (4)	C27—C26—H26	119.9
C4—C3—H3	121.0	C25—C26—H26	119.9
C2—C3—H3	121.0	C26—C27—C28	118.1 (4)
C3—C4—C5	122.4 (4)	C26—C27—H27	121.0
C3—C4—H4	118.8	C28—C27—H27	121.0
C5—C4—H4	118.8	C27—C28—C23	122.1 (4)
C6—C5—C4	120.0 (4)	C27—C28—S8	126.8 (3)
C6—C5—H5	120.0	C23—C28—S8	110.9 (3)
C4—C5—H5	120.0	Cl3—C29—Cl4	115.7 (3)
C5—C6—C7	118.5 (4)	Cl3—C29—H29A	108.4
C5—C6—H6	120.8	Cl4—C29—H29A	108.4
C7—C6—H6	120.8	Cl3—C29—H29B	108.4
C6—C7—C2	121.2 (4)	Cl4—C29—H29B	108.4
C6—C7—S2	127.5 (3)	H29A—C29—H29B	107.4
S1—Re1—Re2—N1	−17.44 (8)	N3—Re1—Re2—S5	−17.91 (9)
S3—Re1—Re2—N2	−20.26 (9)	N4—Re1—Re2—S7	−16.46 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl2	0.94	2.50	3.347 (4)	150
C24—H24···Cl1	0.94	2.52	3.382 (4)	153