Supramolecular association via Sb...S and C—H...S interactions in dimeric tris(N,N-dimethyldithiocarbamato-S,S′)antimony(III): an approach to overcome the concept of steric bulk on such interactions

Tris(N,N-dimethyldithiocarbamato-S,S′)antimony(III) has been isolated as a dimer in acetonitrile. Single-crystal X-ray analysis shows that the molecule possesses both Sb...S and C—H...S interactions, which results in a supramolecular association in the absence of hydrogen-bonding functionality on the R group. The co-existence in the title compound of such interactions is a unique character of known dimeric antimony(III) alkyl and/or aryl dithiocarbamate complexes. The literature reveals that the species where the alkyl and/or aryl dithiocarbamates carry the following groups: R = methyl (chloroform solvated), ethyl, n-propyl, pyrrolidine, morpholine, piperidine, azepane, benzyl, methylphenyl, are not capable of forming significant hydrogen-bonding interactions. However, either Sb...S or C—H...S intermolecular interactions dominate between two centrosymmetrically related molecules leading to a supramolecular aggregation. In the species where the R group carries hydrogen-bonding functionality, i.e. 2-hydroxylethyl, the C—H...S interactions are subverted by O—H...O hydrogen bonding. In addition, the title compound does not have steric hindrance or any hydrogen-bonding group but is stabilized with the co-existence of Sb...S and C—H...S interactions. Analysis of the secondary interactions of a series of analogues previously reported reveals that steric bulk is unnecessary for the mitigation of Sb...S interactions and for the establishment of C—H...S secondary bonding.

S1. Experimental

S1.1. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

S2. Results and discussion

Computing details

Data collection: CrysAlis CCD, Oxford Diffraction Ltd.,; cell refinement: CrysAlis RED, Oxford Diffraction Ltd.,; data reduction: CrysAlis RED, Oxford Diffraction Ltd.,; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3; software used to prepare material for publication: SHELX97.

Figures

(I)

Crystal data

C18H36N6S12Sb2	Z = 2
Mr = 964.75	F(000) = 960
Triclinic, P1	Dx = 1.787 Mg m^−3
a = 10.8746 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2843 (7) Å	Cell parameters from 7299 reflections
c = 15.0197 (7) Å	θ = 3.0–32.8°
α = 99.886 (5)°	µ = 2.23 mm^−1
β = 96.852 (5)°	T = 150 K
γ = 94.714 (5)°	Block, yellow
V = 1792.81 (19) Å^3	0.23 × 0.18 × 0.14 mm

Data collection

OXFORD DIFFRACTION SUPER NOVA diffractometer	6292 independent reflections
Radiation source: Micro-Focus (Mo) X-ray Source	4452 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.137
Detector resolution: 15.9948 pixels mm^-1	θmax = 25.0°, θmin = 3.1°
ω/q–scan	h = −12→12
Absorption correction: multi-scan CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET) (compiled Oct 18 2006,16:28:17) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −13→8
Tmin = 0.628, Tmax = 0.746	l = −17→17
13538 measured reflections

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)] = 0.143	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.401	H-atom parameters constrained
S = 1.42	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
6292 reflections	(Δ/σ)max < 0.001
355 parameters	Δρmax = 8.48 e Å^−3
0 restraints	Δρmin = −4.81 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Sb1	0.52891 (9)	0.13781 (8)	0.77543 (6)	0.0306 (4)
Sb2	0.85932 (9)	0.46572 (9)	0.73030 (7)	0.0304 (4)
S1	0.7209 (4)	0.3019 (3)	0.8806 (3)	0.0406 (10)
S2	0.7377 (4)	0.0431 (4)	0.8153 (3)	0.0437 (10)
S3	0.4773 (4)	−0.0992 (4)	0.7226 (3)	0.0390 (10)
S4	0.2716 (4)	0.0527 (4)	0.6965 (3)	0.0423 (10)
S5	0.4578 (4)	0.1107 (3)	0.9211 (2)	0.0318 (8)
S6	0.4041 (5)	0.3392 (3)	0.8568 (3)	0.0454 (11)
S7	0.6858 (4)	0.2840 (4)	0.6242 (3)	0.0364 (9)
S8	0.9497 (4)	0.2592 (3)	0.6775 (3)	0.0381 (10)
S9	1.1019 (4)	0.5091 (4)	0.7771 (3)	0.0372 (9)
S10	0.9531 (4)	0.7176 (4)	0.8100 (3)	0.0418 (10)
S11	0.8887 (3)	0.5330 (3)	0.5852 (2)	0.0305 (8)
S12	0.6553 (4)	0.5924 (4)	0.6596 (3)	0.0450 (11)
N1	0.9298 (15)	0.2010 (15)	0.8974 (10)	0.055 (4)
N2	0.2542 (13)	−0.1899 (12)	0.6392 (9)	0.039 (3)
N3	0.3557 (13)	0.2864 (11)	1.0152 (9)	0.038 (3)
N4	0.7849 (14)	0.0788 (12)	0.5878 (10)	0.044 (3)
N5	1.1946 (12)	0.7277 (12)	0.8621 (8)	0.035 (3)
N6	0.7150 (14)	0.6390 (11)	0.5015 (8)	0.041 (3)
C1	0.8122 (15)	0.1848 (13)	0.8675 (10)	0.035 (4)
C2	0.3245 (14)	−0.0864 (12)	0.6792 (9)	0.029 (3)
C3	0.4006 (13)	0.2540 (11)	0.9371 (10)	0.028 (3)
C4	0.9976 (16)	0.3163 (18)	0.9422 (13)	0.060 (6)
H4A	0.9683	0.3807	0.9114	0.089*
H4B	1.0868	0.3130	0.9393	0.089*
H4C	0.9832	0.3330	1.0062	0.089*
C5	1.0086 (19)	0.100 (2)	0.8841 (15)	0.067 (6)
H5A	0.9620	0.0255	0.8922	0.101*
H5B	1.0839	0.1185	0.9290	0.101*
H5C	1.0320	0.0898	0.8225	0.101*
C6	0.2965 (19)	−0.3066 (14)	0.6260 (11)	0.045 (4)
H6A	0.3871	−0.2986	0.6268	0.068*
H6B	0.2567	−0.3532	0.5670	0.068*
H6C	0.2750	−0.3484	0.6749	0.068*
C7	0.1188 (14)	−0.1875 (18)	0.6030 (14)	0.053 (5)
H7A	0.0662	−0.2342	0.6361	0.079*
H7B	0.1041	−0.2231	0.5379	0.079*
H7C	0.0984	−0.1037	0.6115	0.079*
C8	0.3439 (16)	0.2094 (16)	1.0842 (11)	0.045 (4)
H8A	0.3815	0.1344	1.0664	0.067*
H8B	0.2556	0.1900	1.0888	0.067*
H8C	0.3867	0.2525	1.1435	0.067*
C9	0.3157 (16)	0.4058 (15)	1.0407 (15)	0.051 (5)
H9A	0.3642	0.4468	1.0986	0.077*
H9B	0.2271	0.3980	1.0476	0.077*
H9C	0.3289	0.4532	0.9931	0.077*
C10	0.8016 (16)	0.1947 (12)	0.6249 (11)	0.035 (4)
C11	1.0898 (18)	0.6633 (15)	0.8223 (9)	0.041 (4)
C12	0.7453 (14)	0.5953 (13)	0.5764 (12)	0.039 (4)
C13	0.660 (2)	0.0216 (18)	0.5465 (14)	0.065 (7)
H13A	0.6631	−0.0650	0.5253	0.098*
H13B	0.6305	0.0590	0.4947	0.098*
H13C	0.6021	0.0327	0.5920	0.098*
C14	0.883 (2)	−0.0053 (15)	0.5963 (15)	0.061 (6)
H14A	0.9650	0.0379	0.5958	0.092*
H14B	0.8668	−0.0736	0.5449	0.092*
H14C	0.8823	−0.0355	0.6536	0.092*
C15	1.3148 (16)	0.6833 (18)	0.8711 (12)	0.049 (5)
H15A	1.3062	0.5965	0.8461	0.073*
H15B	1.3497	0.6972	0.9357	0.073*
H15C	1.3705	0.7260	0.8376	0.073*
C16	1.1969 (18)	0.8601 (14)	0.9008 (12)	0.047 (4)
H16A	1.2284	0.9081	0.8582	0.070*
H16B	1.2515	0.8797	0.9593	0.070*
H16C	1.1124	0.8788	0.9100	0.070*
C17	0.795 (2)	0.6489 (18)	0.4337 (12)	0.058 (5)
H17A	0.8669	0.6036	0.4447	0.088*
H17B	0.8244	0.7342	0.4367	0.088*
H17C	0.7493	0.6157	0.3731	0.088*
C18	0.5916 (17)	0.6803 (16)	0.4847 (13)	0.051 (5)
H18A	0.5275	0.6131	0.4821	0.077*
H18B	0.5831	0.7092	0.4266	0.077*
H18C	0.5817	0.7463	0.5341	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sb1	0.0364 (7)	0.0278 (6)	0.0270 (6)	0.0085 (4)	0.0022 (5)	0.0023 (5)
Sb2	0.0274 (7)	0.0346 (7)	0.0276 (7)	0.0068 (4)	−0.0012 (5)	0.0031 (5)
S1	0.055 (3)	0.0295 (19)	0.033 (2)	−0.0038 (18)	0.003 (2)	−0.0019 (17)
S2	0.040 (2)	0.039 (2)	0.055 (3)	0.0187 (17)	0.010 (2)	0.008 (2)
S3	0.048 (2)	0.0300 (19)	0.035 (2)	0.0077 (17)	0.0009 (19)	−0.0017 (17)
S4	0.049 (3)	0.044 (2)	0.035 (2)	0.0171 (18)	0.003 (2)	0.0059 (18)
S5	0.039 (2)	0.0268 (17)	0.0303 (19)	0.0113 (14)	0.0020 (17)	0.0041 (15)
S6	0.065 (3)	0.0290 (19)	0.048 (2)	0.0225 (18)	0.011 (2)	0.0132 (18)
S7	0.032 (2)	0.044 (2)	0.0285 (19)	0.0000 (17)	−0.0069 (17)	0.0048 (17)
S8	0.033 (2)	0.0330 (19)	0.048 (2)	0.0095 (15)	0.0035 (19)	0.0048 (18)
S9	0.033 (2)	0.040 (2)	0.038 (2)	0.0069 (16)	−0.0018 (18)	0.0054 (18)
S10	0.046 (2)	0.042 (2)	0.036 (2)	0.0162 (18)	0.001 (2)	0.0017 (18)
S11	0.0263 (18)	0.0353 (18)	0.0305 (18)	0.0128 (14)	0.0014 (16)	0.0046 (16)
S12	0.038 (2)	0.060 (3)	0.043 (2)	0.0246 (19)	0.010 (2)	0.015 (2)
N1	0.052 (10)	0.068 (10)	0.045 (9)	−0.010 (8)	0.012 (8)	0.015 (8)
N2	0.039 (8)	0.041 (7)	0.037 (7)	0.015 (6)	0.001 (6)	0.004 (6)
N3	0.041 (8)	0.026 (6)	0.043 (8)	−0.001 (5)	0.005 (7)	0.001 (6)
N4	0.046 (9)	0.039 (8)	0.045 (8)	−0.003 (6)	0.005 (7)	0.000 (6)
N5	0.031 (7)	0.043 (7)	0.028 (6)	0.011 (5)	−0.013 (6)	0.005 (6)
N6	0.065 (10)	0.041 (7)	0.027 (6)	0.016 (7)	0.025 (7)	0.012 (6)
C1	0.037 (9)	0.031 (8)	0.031 (8)	−0.012 (6)	−0.020 (7)	0.013 (7)
C2	0.040 (8)	0.027 (7)	0.018 (6)	0.013 (6)	−0.001 (6)	0.000 (6)
C3	0.025 (7)	0.017 (6)	0.037 (8)	0.008 (5)	−0.006 (6)	−0.004 (6)
C4	0.033 (9)	0.075 (13)	0.055 (11)	−0.024 (9)	−0.037 (9)	0.012 (10)
C5	0.048 (12)	0.105 (17)	0.074 (14)	0.024 (11)	0.036 (11)	0.061 (13)
C6	0.073 (13)	0.028 (8)	0.027 (8)	0.002 (8)	−0.013 (9)	−0.001 (7)
C7	0.019 (8)	0.070 (12)	0.069 (13)	0.000 (7)	−0.008 (8)	0.026 (10)
C8	0.044 (10)	0.059 (10)	0.034 (8)	0.011 (8)	0.013 (8)	0.009 (8)
C9	0.035 (9)	0.041 (9)	0.077 (13)	0.012 (7)	0.020 (10)	−0.004 (9)
C10	0.047 (10)	0.020 (7)	0.037 (8)	−0.005 (6)	0.006 (8)	0.003 (6)
C11	0.065 (12)	0.050 (9)	0.011 (6)	0.007 (8)	0.004 (7)	0.016 (7)
C12	0.027 (8)	0.031 (7)	0.051 (9)	0.016 (6)	−0.008 (8)	−0.008 (7)
C13	0.078 (15)	0.055 (12)	0.050 (11)	−0.033 (11)	0.017 (11)	−0.013 (10)
C14	0.080 (15)	0.031 (8)	0.069 (13)	0.000 (9)	0.031 (12)	−0.014 (9)
C15	0.036 (10)	0.075 (13)	0.030 (8)	−0.002 (8)	0.000 (8)	0.003 (9)
C16	0.059 (12)	0.031 (8)	0.045 (10)	−0.012 (8)	0.000 (9)	0.007 (8)
C17	0.078 (15)	0.062 (12)	0.040 (9)	0.030 (10)	0.012 (10)	0.009 (9)
C18	0.054 (11)	0.047 (10)	0.051 (11)	−0.001 (8)	−0.008 (9)	0.017 (9)

Geometric parameters (Å, º)

Sb1—S5	2.465 (4)	N6—C12	1.32 (2)
Sb1—S2	2.636 (4)	N6—C17	1.43 (2)
Sb1—S3	2.649 (4)	N6—C18	1.46 (2)
Sb1—S1	2.803 (4)	C4—H4A	0.9800
Sb1—S6	2.907 (4)	C4—H4B	0.9800
Sb1—S4	2.921 (5)	C4—H4C	0.9800
Sb2—S11	2.475 (4)	C5—H5A	0.9800
Sb2—S9	2.631 (4)	C5—H5B	0.9800
Sb2—S8	2.638 (4)	C5—H5C	0.9800
Sb2—S7	2.798 (4)	C6—H6A	0.9800
Sb2—S12	2.928 (4)	C6—H6B	0.9800
Sb2—S10	2.936 (4)	C6—H6C	0.9800
S1—C1	1.716 (18)	C7—H7A	0.9800
S2—C1	1.741 (14)	C7—H7B	0.9800
S3—C2	1.738 (16)	C7—H7C	0.9800
S4—C2	1.705 (14)	C8—H8A	0.9800
S5—C3	1.768 (13)	C8—H8B	0.9800
S6—C3	1.669 (14)	C8—H8C	0.9800
S7—C10	1.676 (17)	C9—H9A	0.9800
S8—C10	1.748 (17)	C9—H9B	0.9800
S9—C11	1.778 (17)	C9—H9C	0.9800
S10—C11	1.66 (2)	C13—H13A	0.9800
S11—C12	1.762 (15)	C13—H13B	0.9800
S12—C12	1.678 (17)	C13—H13C	0.9800
N1—C1	1.29 (2)	C14—H14A	0.9800
N1—C4	1.45 (2)	C14—H14B	0.9800
N1—C5	1.48 (3)	C14—H14C	0.9800
N2—C2	1.346 (19)	C15—H15A	0.9800
N2—C6	1.42 (2)	C15—H15B	0.9800
N2—C7	1.51 (2)	C15—H15C	0.9800
N3—C3	1.328 (19)	C16—H16A	0.9800
N3—C9	1.45 (2)	C16—H16B	0.9800
N3—C8	1.47 (2)	C16—H16C	0.9800
N4—C10	1.32 (2)	C17—H17A	0.9800
N4—C13	1.47 (2)	C17—H17B	0.9800
N4—C14	1.50 (3)	C17—H17C	0.9800
N5—C11	1.32 (2)	C18—H18A	0.9800
N5—C15	1.44 (2)	C18—H18B	0.9800
N5—C16	1.50 (2)	C18—H18C	0.9800
S5—Sb1—S2	92.07 (14)	N1—C5—H5A	109.5
S5—Sb1—S3	86.77 (12)	N1—C5—H5B	109.5
S2—Sb1—S3	73.84 (14)	H5A—C5—H5B	109.5
S5—Sb1—S1	86.39 (13)	N1—C5—H5C	109.5
S2—Sb1—S1	65.47 (14)	H5A—C5—H5C	109.5
S3—Sb1—S1	138.39 (14)	H5B—C5—H5C	109.5
S5—Sb1—S6	66.86 (12)	N2—C6—H6A	109.5
S2—Sb1—S6	136.58 (14)	N2—C6—H6B	109.5
S3—Sb1—S6	137.28 (14)	H6A—C6—H6B	109.5
S1—Sb1—S6	75.30 (14)	N2—C6—H6C	109.5
S5—Sb1—S4	84.83 (12)	H6A—C6—H6C	109.5
S2—Sb1—S4	137.76 (13)	H6B—C6—H6C	109.5
S3—Sb1—S4	63.94 (13)	N2—C7—H7A	109.5
S1—Sb1—S4	155.36 (13)	N2—C7—H7B	109.5
S6—Sb1—S4	80.09 (13)	H7A—C7—H7B	109.5
S11—Sb2—S9	87.74 (13)	N2—C7—H7C	109.5
S11—Sb2—S8	91.85 (12)	H7A—C7—H7C	109.5
S9—Sb2—S8	74.31 (13)	H7B—C7—H7C	109.5
S11—Sb2—S7	85.92 (12)	N3—C8—H8A	109.5
S9—Sb2—S7	138.82 (13)	N3—C8—H8B	109.5
S8—Sb2—S7	65.30 (13)	H8A—C8—H8B	109.5
S11—Sb2—S12	66.14 (12)	N3—C8—H8C	109.5
S9—Sb2—S12	137.54 (13)	H8A—C8—H8C	109.5
S8—Sb2—S12	135.68 (13)	H8B—C8—H8C	109.5
S7—Sb2—S12	74.77 (13)	N3—C9—H9A	109.5
S11—Sb2—S10	83.16 (12)	N3—C9—H9B	109.5
S9—Sb2—S10	64.21 (13)	H9A—C9—H9B	109.5
S8—Sb2—S10	138.35 (13)	N3—C9—H9C	109.5
S7—Sb2—S10	154.05 (13)	H9A—C9—H9C	109.5
S12—Sb2—S10	79.29 (13)	H9B—C9—H9C	109.5
C1—S1—Sb1	86.1 (5)	N4—C10—S7	122.7 (13)
C1—S2—Sb1	91.1 (6)	N4—C10—S8	119.3 (14)
C2—S3—Sb1	92.8 (5)	S7—C10—S8	118.0 (8)
C2—S4—Sb1	84.5 (5)	N5—C11—S10	124.5 (13)
C3—S5—Sb1	92.5 (5)	N5—C11—S9	115.8 (14)
C3—S6—Sb1	80.2 (5)	S10—C11—S9	119.7 (10)
C10—S7—Sb2	86.3 (5)	N6—C12—S12	124.5 (13)
C10—S8—Sb2	90.2 (5)	N6—C12—S11	116.0 (13)
C11—S9—Sb2	91.7 (6)	S12—C12—S11	119.5 (10)
C11—S10—Sb2	84.1 (6)	N4—C13—H13A	109.5
C12—S11—Sb2	93.7 (6)	N4—C13—H13B	109.5
C12—S12—Sb2	80.6 (6)	H13A—C13—H13B	109.5
C1—N1—C4	124.8 (18)	N4—C13—H13C	109.5
C1—N1—C5	120.9 (17)	H13A—C13—H13C	109.5
C4—N1—C5	114.2 (17)	H13B—C13—H13C	109.5
C2—N2—C6	125.4 (15)	N4—C14—H14A	109.5
C2—N2—C7	120.1 (14)	N4—C14—H14B	109.5
C6—N2—C7	114.5 (14)	H14A—C14—H14B	109.5
C3—N3—C9	121.5 (14)	N4—C14—H14C	109.5
C3—N3—C8	124.9 (13)	H14A—C14—H14C	109.5
C9—N3—C8	113.6 (15)	H14B—C14—H14C	109.5
C10—N4—C13	120.1 (17)	N5—C15—H15A	109.5
C10—N4—C14	123.5 (16)	N5—C15—H15B	109.5
C13—N4—C14	115.8 (15)	H15A—C15—H15B	109.5
C11—N5—C15	125.5 (15)	N5—C15—H15C	109.5
C11—N5—C16	120.7 (14)	H15A—C15—H15C	109.5
C15—N5—C16	113.8 (13)	H15B—C15—H15C	109.5
C12—N6—C17	124.4 (17)	N5—C16—H16A	109.5
C12—N6—C18	119.2 (13)	N5—C16—H16B	109.5
C17—N6—C18	116.4 (14)	H16A—C16—H16B	109.5
N1—C1—S1	121.2 (13)	N5—C16—H16C	109.5
N1—C1—S2	122.0 (14)	H16A—C16—H16C	109.5
S1—C1—S2	116.8 (9)	H16B—C16—H16C	109.5
N2—C2—S4	124.8 (12)	N6—C17—H17A	109.5
N2—C2—S3	116.6 (11)	N6—C17—H17B	109.5
S4—C2—S3	118.5 (8)	H17A—C17—H17B	109.5
N3—C3—S6	123.9 (11)	N6—C17—H17C	109.5
N3—C3—S5	115.7 (11)	H17A—C17—H17C	109.5
S6—C3—S5	120.3 (9)	H17B—C17—H17C	109.5
N1—C4—H4A	109.5	N6—C18—H18A	109.5
N1—C4—H4B	109.5	N6—C18—H18B	109.5
H4A—C4—H4B	109.5	H18A—C18—H18B	109.5
N1—C4—H4C	109.5	N6—C18—H18C	109.5
H4A—C4—H4C	109.5	H18A—C18—H18C	109.5
H4B—C4—H4C	109.5	H18B—C18—H18C	109.5
S5—Sb1—S1—C1	98.6 (5)	S10—Sb2—S11—C12	−82.4 (5)
S2—Sb1—S1—C1	4.6 (5)	S11—Sb2—S12—C12	1.2 (5)
S3—Sb1—S1—C1	17.6 (6)	S9—Sb2—S12—C12	58.1 (6)
S6—Sb1—S1—C1	165.6 (5)	S8—Sb2—S12—C12	−65.0 (6)
S4—Sb1—S1—C1	167.8 (5)	S7—Sb2—S12—C12	−91.0 (5)
S5—Sb1—S2—C1	−89.6 (5)	S10—Sb2—S12—C12	88.4 (5)
S3—Sb1—S2—C1	−175.7 (6)	C4—N1—C1—S1	−1 (2)
S1—Sb1—S2—C1	−4.6 (5)	C5—N1—C1—S1	−178.7 (12)
S6—Sb1—S2—C1	−31.9 (6)	C4—N1—C1—S2	−179.4 (13)
S4—Sb1—S2—C1	−174.2 (5)	C5—N1—C1—S2	3 (2)
S5—Sb1—S3—C2	89.3 (5)	Sb1—S1—C1—N1	174.7 (13)
S2—Sb1—S3—C2	−177.6 (5)	Sb1—S1—C1—S2	−7.2 (8)
S1—Sb1—S3—C2	170.1 (5)	Sb1—S2—C1—N1	−174.3 (13)
S6—Sb1—S3—C2	39.2 (5)	Sb1—S2—C1—S1	7.6 (9)
S4—Sb1—S3—C2	3.5 (5)	C6—N2—C2—S4	−178.8 (12)
S5—Sb1—S4—C2	−92.5 (5)	C7—N2—C2—S4	2 (2)
S2—Sb1—S4—C2	−5.1 (5)	C6—N2—C2—S3	−3 (2)
S3—Sb1—S4—C2	−3.5 (5)	C7—N2—C2—S3	177.6 (11)
S1—Sb1—S4—C2	−162.0 (5)	Sb1—S4—C2—N2	−179.1 (13)
S6—Sb1—S4—C2	−159.8 (5)	Sb1—S4—C2—S3	5.5 (8)
S2—Sb1—S5—C3	138.5 (5)	Sb1—S3—C2—N2	178.2 (11)
S3—Sb1—S5—C3	−147.8 (5)	Sb1—S3—C2—S4	−6.1 (8)
S1—Sb1—S5—C3	73.3 (5)	C9—N3—C3—S6	−6 (2)
S6—Sb1—S5—C3	−2.3 (5)	C8—N3—C3—S6	175.7 (12)
S4—Sb1—S5—C3	−83.7 (5)	C9—N3—C3—S5	174.6 (13)
S5—Sb1—S6—C3	2.4 (5)	C8—N3—C3—S5	−4 (2)
S2—Sb1—S6—C3	−64.3 (5)	Sb1—S6—C3—N3	176.9 (13)
S3—Sb1—S6—C3	58.9 (5)	Sb1—S6—C3—S5	−3.6 (7)
S1—Sb1—S6—C3	−89.9 (5)	Sb1—S5—C3—N3	−176.2 (11)
S4—Sb1—S6—C3	91.0 (5)	Sb1—S5—C3—S6	4.2 (8)
S11—Sb2—S7—C10	96.5 (5)	C13—N4—C10—S7	−2 (2)
S9—Sb2—S7—C10	14.7 (6)	C14—N4—C10—S7	−173.2 (13)
S8—Sb2—S7—C10	2.6 (5)	C13—N4—C10—S8	177.5 (12)
S12—Sb2—S7—C10	162.9 (5)	C14—N4—C10—S8	7 (2)
S10—Sb2—S7—C10	161.7 (6)	Sb2—S7—C10—N4	175.8 (14)
S11—Sb2—S8—C10	−87.1 (5)	Sb2—S7—C10—S8	−4.1 (8)
S9—Sb2—S8—C10	−174.3 (5)	Sb2—S8—C10—N4	−175.5 (13)
S7—Sb2—S8—C10	−2.5 (5)	Sb2—S8—C10—S7	4.3 (9)
S12—Sb2—S8—C10	−30.3 (6)	C15—N5—C11—S10	−178.0 (11)
S10—Sb2—S8—C10	−168.9 (5)	C16—N5—C11—S10	0 (2)
S11—Sb2—S9—C11	86.6 (4)	C15—N5—C11—S9	0 (2)
S8—Sb2—S9—C11	179.2 (5)	C16—N5—C11—S9	178.4 (10)
S7—Sb2—S9—C11	167.8 (4)	Sb2—S10—C11—N5	−176.6 (12)
S12—Sb2—S9—C11	36.6 (5)	Sb2—S10—C11—S9	5.1 (7)
S10—Sb2—S9—C11	3.1 (4)	Sb2—S9—C11—N5	175.9 (10)
S11—Sb2—S10—C11	−94.1 (5)	Sb2—S9—C11—S10	−5.7 (8)
S9—Sb2—S10—C11	−3.3 (5)	C17—N6—C12—S12	175.6 (13)
S8—Sb2—S10—C11	−9.1 (5)	C18—N6—C12—S12	−5 (2)
S7—Sb2—S10—C11	−159.9 (5)	C17—N6—C12—S11	−6 (2)
S12—Sb2—S10—C11	−161.1 (5)	C18—N6—C12—S11	173.5 (12)
S9—Sb2—S11—C12	−146.7 (5)	Sb2—S12—C12—N6	176.3 (14)
S8—Sb2—S11—C12	139.0 (5)	Sb2—S12—C12—S11	−1.8 (8)
S7—Sb2—S11—C12	74.0 (5)	Sb2—S11—C12—N6	−176.1 (11)
S12—Sb2—S11—C12	−1.2 (5)	Sb2—S11—C12—S12	2.2 (9)