Tris(N-butyl-N-ethyl­di­thio­carbamato)­bismuth(III)

The Bi atom in the title compound, [Bi(C₇H₁₄NS₂)₃], is coordinated by six S atoms from three bidentate N-butyl-N-ethyl­di­thio­carbamate ligands; it is also engaged in an additional Bi...S interaction which links two tris(N-butyl-N-ethyl­di­thio­carbamato)­bismuth fragments into centrosymmetric binuclear dimers. Thus, each of the Bi atoms in the dimer has a distorted pentagonal–bipyramidal environment, with one short axial Bi—S distance of 2.608 (2) Å, one long axial Bi...S interaction of 3.334 (2) Å, and five `regular' equatorial bonds in the range 2.819 (2)-2.867 (2) Å.

Key indicators

• Single-crystal X-ray study
• T = 183 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.059
• wR factor = 0.162
• Data-to-parameter ratio = 25.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
          Tmin and Tmax reported:      0.254     0.433
          Tmin and Tmax expected:      0.167     0.366
          RR =      1.288
          Please check that your absorption correction is appropriate.

PLAT_213  Alert C Atom C6      has ADP max/min Ratio ...........       3.50 prolate

PLAT_702  Alert C Angle   Calc   136.16(5), Rep  136.10(10), Dev.      1.20 Sigma
                     S2   -BI1  -S6      1.555   1.555   1.555

PLAT_702  Alert C Angle   Calc   124.56(5), Rep  124.50(10), Dev.      1.20 Sigma
                     S1   -BI1  -S5      1.555   1.555   2.666

PLAT_731  Alert C Bond    Calc     1.51(3), Rep    1.509(9) ....       3.33 su-Ratio
                     C6   -C7      1.555   1.555

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.846
          Tmax scaled      0.366 Tmin scaled      0.215


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 5 Alert Level C = Please check

---

S1. Comment

The tris(dithiocarbamato)bismuth(III) and tris(dithiocarbamato)antimony(III) complexes generally have the chelated metal atom with a capped octahedral geometry as the lone pair of electrons is stereochemically active (Raston & White, 1976; Venkatachalam et al., 1997). Our recent study of the tris(2-hydroxyethylisopropyl)bismuth complex has documented this geometry for the metal atom (Low et al., 2001).

The nature of the substituents in the dithiocarbamate group appears to affect the stereochemical activity; the Bi atom in the title compound, (I) (Fig. 1), is seven-coordinated and has a distorted pentagonal–bipyramidal environment with one short axial distance [Bi1—S4 2.608 (2) Å], one long axial interaction [Bi1···S5ⁱ 3.334 (2) Å; symmetry code: (i) 1 − x, 1 − y, 1 − z], and five `regular' equatorial bonds [2.819 (2)–2.867 (2) Å]; the angle formed by two axial bonds, S4—Bi1···S5ⁱ, is 141.0 (1) Å. The long axial Bi1···S5ⁱ interaction links two adjacent tris(N-butyl-N-ethyldithiocarbamato)bismuth fragments into a centrosymmetric dinuclear entity (Fig. 2).

S2. Experimental

Bismuth trichloride (3.15 g, 10 mmol) was dissolved in a small volume of ethanol. The solution was cooled in an ice bath, then ethylbutylamine (3.03 g, 30 mmol) and an excess of carbon disulfide (2 ml) were added; the mixture was stirred for several hours. The solid which separated had a melting point of 396–397 K. Elemental analysis, found: C 33.94, H,4.93, N 5.69, S 26.94%; calculated for C₂₁H₄₂BiN₃S₆: C 31.48, H 5.74, N 5.70 S 26.07%.

S3. Refinement

Although the cell dimensions define almost exactly a C-centered monoclinic lattice (β = 89.87°), the structure does not have true monoclinic symmetry (R_int = 0.468) and was solved and refined as triclinic. The C—C distances in the ethyl and butyl groups were restrained to 1.54±0.01 Å; in the butyl chain, an additional restriction of C···C = 2.51±0.01 Å was used. The N—C_alkyl distances in each dithiocarbamate unit were restrained to be equal to each other by a SADI 0.01 instruction in SHELXL97. The H atoms were positioned geometrically and allowed to ride on their parent C atoms, with U_iso(H) = 1.2U_eq(C) for the methylene H atoms and 1.5U_eq(C) for the methyl H atoms. The final difference Fourier map had a large peak/hole near the Bi atom.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. ORTEPII (Johnson, 1976) plot of the molecule of the title compound; displacement ellipsoids are drawn at 50% probability level. The long Bi···S interaction is shown as a dashed line. H atoms are drawn as spheres of arbitrary radii.
	Fig. 2. The centrosymmetric binuclear aggregates in the structure of the title compound. Only Bi and S atoms are shown; displacement ellipsoids are at the 50% probability level.

Tris(N-butyl-N-ethyldithiocarbamato)bismuth(III)

Crystal data

[Bi(C7H14NS2)3]	Z = 2
Mr = 737.92	F(000) = 736
Triclinic, P1	Dx = 1.627 Mg m^−3
a = 10.5120 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.5128 (1) Å	Cell parameters from 8192 reflections
c = 14.5755 (1) Å	θ = 1.5–28.3°
α = 99.713 (1)°	µ = 6.28 mm^−1
β = 99.927 (1)°	T = 183 K
γ = 103.383 (1)°	Block, yellow
V = 1506.52 (2) Å^3	0.30 × 0.26 × 0.16 mm

Data collection

Siemens SMART CCD area-detector diffractometer	7197 independent reflections
Radiation source: fine-focus sealed tube	6368 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 1.5°
ω scans	h = −13→13
Absorption correction: empirical (SADABS; Sheldrick, 1996)	k = −13→12
Tmin = 0.254, Tmax = 0.433	l = −17→19
11016 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.162	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0686P)^2] where P = (Fo^2 + 2Fc^2)/3
7197 reflections	(Δ/σ)max < 0.001
280 parameters	Δρmax = 4.01 e Å^−3
21 restraints	Δρmin = −5.77 e Å^−3

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

	x	y	z	Uiso*/Ueq
Bi1	0.42854 (2)	0.51202 (2)	0.64238 (2)	0.0187 (1)
S1	0.3720 (2)	0.6719 (2)	0.7991 (1)	0.0330 (5)
S2	0.5886 (2)	0.5357 (2)	0.8272 (1)	0.0301 (4)
S3	0.5129 (2)	0.2752 (2)	0.6059 (1)	0.0253 (4)
S4	0.2706 (2)	0.3040 (2)	0.6779 (1)	0.0246 (4)
S5	0.2989 (2)	0.4029 (2)	0.4456 (1)	0.0215 (3)
S6	0.2158 (2)	0.6122 (2)	0.5672 (1)	0.024 (1)
N1	0.5341 (7)	0.6973 (9)	0.9674 (5)	0.041 (2)
N2	0.3461 (5)	0.0791 (6)	0.6542 (4)	0.022 (1)
N3	0.1371 (6)	0.5432 (6)	0.3792 (4)	0.023 (1)
C1	0.5041 (8)	0.6395 (9)	0.8746 (6)	0.030 (2)
C2	0.474 (1)	0.801 (1)	1.0091 (7)	0.057 (3)
C3	0.344 (1)	0.746 (1)	1.0418 (9)	0.064 (3)
C4	0.6362 (7)	0.668 (1)	1.0355 (7)	0.052 (3)
C5	0.7721 (8)	0.763 (1)	1.0386 (7)	0.067 (4)
C6	0.8907 (9)	0.740 (2)	1.1018 (9)	0.13 (1)
C7	0.891 (2)	0.594 (2)	1.081 (1)	0.115 (7)
C8	0.3746 (7)	0.2055 (7)	0.6458 (5)	0.020 (1)
C9	0.2333 (8)	0.0179 (8)	0.6918 (6)	0.036 (2)
C10	0.1024 (8)	−0.040 (1)	0.6145 (7)	0.045 (2)
C11	0.4285 (7)	−0.0092 (8)	0.6279 (5)	0.028 (2)
C12	0.5438 (7)	−0.0030 (8)	0.7111 (5)	0.030 (2)
C13	0.6284 (7)	−0.0939 (9)	0.6798 (6)	0.038 (2)
C14	0.739 (1)	−0.092 (1)	0.7636 (9)	0.063 (3)
C15	0.2080 (6)	0.5220 (7)	0.4543 (5)	0.018 (1)
C16	0.0573 (7)	0.6412 (7)	0.3824 (6)	0.028 (2)
C17	0.142 (1)	0.7762 (8)	0.3715 (8)	0.049 (3)
C18	0.1290 (6)	0.4684 (7)	0.2826 (5)	0.026 (2)
C19	0.0127 (7)	0.3400 (8)	0.2510 (5)	0.033 (2)
C20	0.0021 (8)	0.2760 (8)	0.1466 (5)	0.038 (2)
C21	−0.098 (1)	0.1375 (9)	0.1174 (7)	0.055 (3)
H2a	0.4547	0.8541	0.9613	0.068*
H2b	0.5406	0.8616	1.0646	0.068*
H3a	0.3100	0.8215	1.0672	0.097*
H3b	0.3621	0.6969	1.0915	0.097*
H3c	0.2762	0.6866	0.9873	0.097*
H4a	0.6384	0.5736	1.0158	0.062*
H4b	0.6153	0.6804	1.0996	0.062*
H5a	0.7870	0.7542	0.9728	0.081*
H5b	0.7685	0.8559	1.0609	0.081*
H6a	0.9748	0.7948	1.0913	0.156*
H6b	0.8877	0.7677	1.1695	0.156*
H7a	0.9683	0.5816	1.1226	0.172*
H7b	0.8948	0.5662	1.0141	0.172*
H7c	0.8081	0.5392	1.0923	0.172*
H9a	0.2195	0.0858	0.7423	0.043*
H9b	0.2548	−0.0549	0.7214	0.043*
H10a	0.0296	−0.0794	0.6436	0.067*
H10b	0.1146	−0.1089	0.5652	0.067*
H10c	0.0797	0.0320	0.5857	0.067*
H11a	0.4666	0.0161	0.5739	0.034*
H11b	0.3712	−0.1024	0.6062	0.034*
H12a	0.6007	0.0903	0.7339	0.035*
H12b	0.5063	−0.0308	0.7646	0.035*
H13a	0.6688	−0.0639	0.6279	0.046*
H13b	0.5709	−0.1866	0.6547	0.046*
H14a	0.7942	−0.1492	0.7418	0.094*
H14b	0.6992	−0.1242	0.8139	0.094*
H14c	0.7959	0.0004	0.7886	0.094*
H16a	0.0288	0.6531	0.4438	0.034*
H16b	−0.0240	0.6081	0.3301	0.034*
H17a	0.0887	0.8413	0.3735	0.074*
H17b	0.1693	0.7641	0.3103	0.074*
H17c	0.2218	0.8090	0.4237	0.074*
H18a	0.2143	0.4445	0.2807	0.031*
H18b	0.1177	0.5269	0.2370	0.031*
H19a	0.0284	0.2762	0.2917	0.039*
H19b	−0.0722	0.3617	0.2584	0.039*
H20a	−0.0271	0.3342	0.1052	0.045*
H20b	0.0913	0.2680	0.1375	0.045*
H21a	−0.1026	0.0986	0.0504	0.082*
H21b	−0.1864	0.1456	0.1253	0.082*
H21c	−0.0681	0.0795	0.1577	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Bi1	0.0199 (2)	0.0187 (2)	0.0212 (2)	0.0110 (1)	0.0050 (1)	0.0059 (1)
S1	0.035 (1)	0.044 (1)	0.024 (1)	0.0248 (9)	0.0030 (8)	−0.0005 (8)
S2	0.0271 (9)	0.043 (1)	0.0260 (9)	0.0204 (9)	0.0056 (8)	0.0079 (8)
S3	0.0230 (8)	0.0263 (9)	0.037 (1)	0.0156 (7)	0.0151 (8)	0.0133 (8)
S4	0.0245 (8)	0.0249 (9)	0.034 (1)	0.0154 (7)	0.0147 (8)	0.0117 (7)
S5	0.0235 (8)	0.0199 (8)	0.0251 (9)	0.0137 (7)	0.0047 (7)	0.0054 (7)
S6	0.0278 (9)	0.0244 (9)	0.0239 (9)	0.0177 (7)	0.0051 (7)	0.0026 (7)
N1	0.036 (4)	0.067 (6)	0.020 (3)	0.025 (4)	0.001 (3)	−0.001 (3)
N2	0.021 (3)	0.023 (3)	0.027 (3)	0.013 (2)	0.008 (2)	0.008 (2)
N3	0.020 (3)	0.028 (3)	0.027 (3)	0.015 (3)	0.004 (2)	0.010 (3)
C1	0.033 (4)	0.039 (5)	0.025 (4)	0.019 (4)	0.008 (3)	0.010 (3)
C2	0.063 (6)	0.084 (9)	0.027 (5)	0.044 (6)	0.002 (5)	−0.005 (5)
C3	0.068 (7)	0.084 (9)	0.056 (7)	0.046 (7)	0.022 (6)	0.012 (6)
C4	0.023 (4)	0.11 (1)	0.029 (5)	0.019 (5)	0.003 (4)	0.020 (5)
C5	0.032 (5)	0.12 (1)	0.038 (6)	0.022 (6)	0.005 (4)	−0.005 (6)
C6	0.063 (9)	0.31 (3)	0.049 (8)	0.11 (1)	0.023 (7)	0.05 (1)
C7	0.10 (1)	0.19 (2)	0.10 (1)	0.10 (2)	0.02 (1)	0.06 (1)
C8	0.026 (3)	0.024 (3)	0.019 (3)	0.017 (3)	0.010 (3)	0.004 (3)
C9	0.057 (5)	0.019 (4)	0.042 (5)	0.014 (4)	0.027 (4)	0.013 (3)
C10	0.032 (5)	0.034 (5)	0.067 (7)	0.006 (4)	0.016 (5)	0.008 (4)
C11	0.036 (4)	0.022 (4)	0.035 (4)	0.018 (3)	0.013 (4)	0.008 (3)
C12	0.038 (4)	0.022 (4)	0.033 (4)	0.017 (3)	0.007 (3)	0.007 (3)
C13	0.029 (4)	0.034 (5)	0.060 (6)	0.022 (4)	0.008 (4)	0.016 (4)
C14	0.040 (5)	0.057 (7)	0.090 (9)	0.027 (5)	−0.009 (6)	0.018 (6)
C15	0.012 (3)	0.017 (3)	0.030 (4)	0.009 (2)	0.007 (3)	0.006 (3)
C16	0.023 (3)	0.035 (4)	0.035 (4)	0.020 (3)	0.007 (3)	0.013 (3)
C17	0.072 (7)	0.035 (5)	0.063 (7)	0.038 (5)	0.026 (6)	0.026 (5)
C18	0.023 (3)	0.039 (4)	0.024 (4)	0.016 (3)	0.008 (3)	0.014 (3)
C19	0.025 (4)	0.042 (5)	0.032 (4)	0.011 (4)	0.009 (3)	0.008 (4)
C20	0.039 (5)	0.046 (5)	0.027 (4)	0.015 (4)	0.006 (4)	0.005 (4)
C21	0.078 (8)	0.048 (6)	0.039 (6)	0.021 (6)	0.016 (5)	0.004 (5)

Geometric parameters (Å, º)

Bi1—S1	2.834 (2)	C3—H3c	0.9800
Bi1—S2	2.858 (2)	C4—H4a	0.9900
Bi1—S3	2.830 (2)	C4—H4b	0.9900
Bi1—S4	2.608 (2)	C5—H5a	0.9900
Bi1—S5	2.867 (2)	C5—H5b	0.9900
Bi1—S6	2.819 (2)	C6—H6a	0.9900
Bi1—S5^i	3.334 (2)	C6—H6b	0.9900
S1—C1	1.753 (8)	C7—H7a	0.9800
S2—C1	1.692 (8)	C7—H7b	0.9800
S3—C8	1.712 (7)	C7—H7c	0.9800
S4—C8	1.739 (7)	C9—H9a	0.9900
S5—C15	1.744 (7)	C9—H9b	0.9900
S6—C15	1.734 (7)	C10—H10a	0.9800
N1—C1	1.34 (1)	C10—H10b	0.9800
N1—C4	1.458 (9)	C10—H10c	0.9800
N1—C2	1.476 (9)	C11—H11a	0.9900
N2—C8	1.32 (1)	C11—H11b	0.9900
N2—C9	1.453 (7)	C12—H12a	0.9900
N2—C11	1.458 (7)	C12—H12b	0.9900
N3—C15	1.296 (9)	C13—H13a	0.9900
N3—C16	1.471 (7)	C13—H13b	0.9900
N3—C18	1.470 (7)	C14—H14a	0.9800
C2—C3	1.543 (9)	C14—H14b	0.9800
C4—C5	1.531 (8)	C14—H14c	0.9800
C5—C6	1.512 (8)	C16—H16a	0.9900
C6—C7	1.509 (9)	C16—H16b	0.9900
C9—C10	1.543 (8)	C17—H17a	0.9800
C11—C12	1.540 (7)	C17—H17b	0.9800
C12—C13	1.516 (7)	C17—H17c	0.9800
C13—C14	1.529 (8)	C18—H18a	0.9900
C16—C17	1.540 (8)	C18—H18b	0.9900
C18—C19	1.536 (7)	C19—H19a	0.9900
C19—C20	1.531 (7)	C19—H19b	0.9900
C20—C21	1.527 (8)	C20—H20a	0.9900
C2—H2a	0.9900	C20—H20b	0.9900
C2—H2b	0.9900	C21—H21a	0.9800
C3—H3a	0.9800	C21—H21b	0.9800
C3—H3b	0.9800	C21—H21c	0.9800
S1—Bi1—S2	62.8 (1)	H5a—C5—H5b	107.5
S1—Bi1—S3	137.5 (1)	C7—C6—H6a	109.4
S1—Bi1—S4	88.1 (1)	C5—C6—H6a	109.4
S1—Bi1—S5	135.6 (1)	C7—C6—H6b	109.4
S1—Bi1—S6	73.4 (1)	C5—C6—H6b	109.4
S2—Bi1—S3	81.1 (1)	H6a—C6—H6b	108.0
S2—Bi1—S4	85.4 (1)	C6—C7—H7a	109.5
S2—Bi1—S5	159.5 (1)	C6—C7—H7b	109.5
S2—Bi1—S6	136.1 (1)	H7a—C7—H7b	109.5
S3—Bi1—S4	66.2 (1)	C6—C7—H7c	109.5
S3—Bi1—S5	78.4 (1)	H7a—C7—H7c	109.5
S3—Bi1—S6	138.0 (1)	H7b—C7—H7c	109.5
S4—Bi1—S5	86.2 (1)	N2—C9—H9a	109.0
S4—Bi1—S6	93.9 (1)	C10—C9—H9a	109.0
S5—Bi1—S6	63.1 (1)	N2—C9—H9b	109.0
S4—Bi1—S5^i	141.0 (1)	C10—C9—H9b	109.0
S6—Bi1—S5^i	114.2 (1)	H9a—C9—H9b	107.8
S3—Bi1—S5^i	74.9 (1)	C9—C10—H10a	109.5
S1—Bi1—S5^i	124.5 (1)	C9—C10—H10b	109.5
S2—Bi1—S5^i	91.4 (1)	H10a—C10—H10b	109.5
S5—Bi1—S5^i	83.5 (1)	C9—C10—H10c	109.5
C1—S1—Bi1	89.0 (3)	H10a—C10—H10c	109.5
C1—S2—Bi1	89.4 (3)	H10b—C10—H10c	109.5
C8—S3—Bi1	84.0 (2)	N2—C11—H11a	109.1
C8—S4—Bi1	90.6 (3)	C12—C11—H11a	109.1
C15—S5—Bi1	88.0 (2)	N2—C11—H11b	109.1
C15—S6—Bi1	89.8 (2)	C12—C11—H11b	109.1
C1—N1—C4	121.9 (7)	H11a—C11—H11b	107.8
C1—N1—C2	123.8 (7)	C13—C12—H12a	109.5
C4—N1—C2	114.2 (8)	C11—C12—H12a	109.5
C8—N2—C9	123.3 (6)	C13—C12—H12b	109.5
C8—N2—C11	122.1 (6)	C11—C12—H12b	109.5
C9—N2—C11	114.6 (6)	H12a—C12—H12b	108.1
C15—N3—C16	123.8 (6)	C12—C13—H13a	109.5
C15—N3—C18	121.9 (6)	C14—C13—H13a	109.5
C16—N3—C18	114.2 (6)	C12—C13—H13b	109.5
N1—C1—S2	122.4 (6)	C14—C13—H13b	109.5
N1—C1—S1	118.9 (6)	H13a—C13—H13b	108.1
S2—C1—S1	118.7 (5)	C13—C14—H14a	109.5
N1—C2—C3	115.1 (9)	C13—C14—H14b	109.5
N1—C4—C5	108.4 (8)	H14a—C14—H14b	109.5
C6—C5—C4	115.1 (7)	C13—C14—H14c	109.5
C7—C6—C5	111.2 (8)	H14a—C14—H14c	109.5
N2—C8—S3	121.6 (5)	H14b—C14—H14c	109.5
N2—C8—S4	119.3 (5)	N3—C16—H16a	109.8
S3—C8—S4	119.1 (4)	C17—C16—H16a	109.8
N2—C9—C10	112.7 (7)	N3—C16—H16b	109.8
N2—C11—C12	112.7 (6)	C17—C16—H16b	109.8
C13—C12—C11	110.7 (5)	H16a—C16—H16b	108.2
C12—C13—C14	110.5 (7)	C16—C17—H17a	109.5
N3—C15—S6	120.8 (5)	C16—C17—H17b	109.5
N3—C15—S5	121.5 (5)	H17a—C17—H17b	109.5
S6—C15—S5	117.7 (4)	C16—C17—H17c	109.5
N3—C16—C17	109.6 (6)	H17a—C17—H17c	109.5
N3—C18—C19	112.9 (5)	H17b—C17—H17c	109.5
C20—C19—C18	109.7 (5)	N3—C18—H18a	109.0
C21—C20—C19	111.0 (6)	C19—C18—H18a	109.0
N1—C2—H2a	108.5	N3—C18—H18b	109.0
C3—C2—H2a	108.5	C19—C18—H18b	109.0
N1—C2—H2b	108.5	H18a—C18—H18b	107.8
C3—C2—H2b	108.5	C20—C19—H19a	109.7
H2a—C2—H2b	107.5	C18—C19—H19a	109.7
C2—C3—H3a	109.5	C20—C19—H19b	109.7
C2—C3—H3b	109.5	C18—C19—H19b	109.7
H3a—C3—H3b	109.5	H19a—C19—H19b	108.2
C2—C3—H3c	109.5	C21—C20—H20a	109.4
H3a—C3—H3c	109.5	C19—C20—H20a	109.4
H3b—C3—H3c	109.5	C21—C20—H20b	109.4
N1—C4—H4a	110.0	C19—C20—H20b	109.4
C5—C4—H4a	110.0	H20a—C20—H20b	108.0
N1—C4—H4b	110.0	C20—C21—H21a	109.5
C5—C4—H4b	110.0	C20—C21—H21b	109.5
H4a—C4—H4b	108.4	H21a—C21—H21b	109.5
C6—C5—H5a	108.5	C20—C21—H21c	109.5
C4—C5—H5a	108.5	H21a—C21—H21c	109.5
C6—C5—H5b	108.5	H21b—C21—H21c	109.5
C4—C5—H5b	108.5
S4—Bi1—S1—C1	87.3 (3)	Bi1—S1—C1—N1	177.5 (8)
S6—Bi1—S1—C1	−178.1 (3)	Bi1—S1—C1—S2	−2.7 (5)
S3—Bi1—S1—C1	36.6 (3)	C1—N1—C2—C3	90 (1)
S2—Bi1—S1—C1	1.6 (3)	C4—N1—C2—C3	−94 (1)
S5—Bi1—S1—C1	169.9 (3)	C1—N1—C4—C5	88 (1)
S4—Bi1—S2—C1	−91.9 (3)	C2—N1—C4—C5	−89 (1)
S6—Bi1—S2—C1	−1.1 (3)	N1—C4—C5—C6	−176.4 (9)
S3—Bi1—S2—C1	−158.5 (3)	C4—C5—C6—C7	50 (2)
S1—Bi1—S2—C1	−1.6 (3)	C9—N2—C8—S3	177.1 (6)
S5—Bi1—S2—C1	−157.9 (3)	C11—N2—C8—S3	−2 (1)
S4—Bi1—S3—C8	−1.3 (3)	C9—N2—C8—S4	−2 (1)
S6—Bi1—S3—C8	−68.9 (3)	C11—N2—C8—S4	179.6 (5)
S1—Bi1—S3—C8	56.5 (3)	Bi1—S3—C8—N2	−176.9 (6)
S2—Bi1—S3—C8	87.6 (3)	Bi1—S3—C8—S4	2.0 (4)
S5—Bi1—S3—C8	−92.2 (3)	Bi1—S4—C8—N2	176.7 (6)
S6—Bi1—S4—C8	143.0 (3)	Bi1—S4—C8—S3	−2.2 (4)
S3—Bi1—S4—C8	1.3 (2)	C8—N2—C9—C10	86.8 (9)
S1—Bi1—S4—C8	−143.8 (3)	C11—N2—C9—C10	−94.5 (8)
S2—Bi1—S4—C8	−81.0 (3)	C8—N2—C11—C12	88.8 (9)
S5—Bi1—S4—C8	80.2 (3)	C9—N2—C11—C12	−89.9 (8)
S4—Bi1—S5—C15	103.0 (2)	N2—C11—C12—C13	−178.7 (7)
S6—Bi1—S5—C15	6.7 (2)	C11—C12—C13—C14	−177.8 (8)
S3—Bi1—S5—C15	169.5 (2)	C18—N3—C15—S6	179.9 (5)
S1—Bi1—S5—C15	19.6 (2)	C16—N3—C15—S6	−1 (1)
S2—Bi1—S5—C15	168.9 (2)	C18—N3—C15—S5	0.0 (9)
S4—Bi1—S6—C15	−90.5 (2)	C16—N3—C15—S5	179.3 (5)
S3—Bi1—S6—C15	−32.5 (2)	Bi1—S6—C15—N3	−168.6 (6)
S1—Bi1—S6—C15	−177.4 (2)	Bi1—S6—C15—S5	11.2 (4)
S2—Bi1—S6—C15	−177.9 (2)	Bi1—S5—C15—N3	168.8 (6)
S5—Bi1—S6—C15	−6.8 (2)	Bi1—S5—C15—S6	−11.0 (4)
C4—N1—C1—S2	−4 (1)	C15—N3—C16—C17	92.5 (9)
C2—N1—C1—S2	172.3 (8)	C18—N3—C16—C17	−88.2 (8)
C4—N1—C1—S1	175.6 (7)	C15—N3—C18—C19	90.5 (8)
C2—N1—C1—S1	−8 (1)	C16—N3—C18—C19	−88.9 (8)
Bi1—S2—C1—N1	−177.5 (8)	N3—C18—C19—C20	174.1 (7)
Bi1—S2—C1—S1	2.6 (5)	C18—C19—C20—C21	171.2 (8)

Symmetry code: (i) −x+1, −y+1, −z+1.