Tris(O-isobutyl dithio­carbonato-κ²S,S′)(1,10-phenanthroline)bis­muth(III)

The title compound, [Bi(C₅H₉OS₂)₂(C₁₂H₈N₂)], is monomeric, with the Bi atom chelated by the S atoms of three anionic O-isobutyl dithio­carbonate ligands and the N atoms of 1,10-phenanthroline. The central Bi atom is eight-coordinate in a capped distorted penta­gonal bipyramidal geometry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.015 Å
• Disorder in main residue
• R factor = 0.045
• wR factor = 0.119
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.74
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Bi1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C8
PLAT301_ALERT_3_C Main Residue  Disorder .........................      13.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         15
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H5A    ..  H4B     ..       1.84 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H5C    ..  H4C     ..       1.86 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      33.00 A   3 
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

Alert level G
ABSTM02_ALERT_3_G  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      0.742
            Tmax scaled      0.251 Tmin scaled      0.243

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

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

Tris(O-isobutyl dithiocarbonato-κ²S,S')(1,10-phenanthroline)bismuth(III)

Crystal data

[Bi(C5H9OS2)2(C12H8N2)]	F(000) = 3312
Mr = 836.91	Dx = 1.617 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4023 reflections
a = 17.366 (3) Å	θ = 2.2–22.4°
b = 13.130 (3) Å	µ = 5.52 mm^−1
c = 30.986 (7) Å	T = 298 K
β = 103.367 (6)°	Block, orange–red
V = 6874 (3) Å^3	0.26 × 0.26 × 0.25 mm
Z = 8

Data collection

Siemens SMART CCD area-detector diffractometer	6050 independent reflections
Radiation source: fine-focus sealed tube	4260 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→20
Tmin = 0.328, Tmax = 0.339	k = −15→15
17747 measured reflections	l = −36→36

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 31.3228P] where P = (Fo^2 + 2Fc^2)/3
6050 reflections	(Δ/σ)max = 0.001
396 parameters	Δρmax = 0.87 e Å^−3
749 restraints	Δρmin = −1.38 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	Occ. (<1)
Bi1	0.20608 (2)	0.48617 (2)	0.167583 (11)	0.04082 (14)
N1	0.0820 (4)	0.6071 (5)	0.1836 (2)	0.0468 (19)
N2	0.0723 (4)	0.3988 (6)	0.1856 (2)	0.0487 (19)
O1	0.3663 (5)	0.6688 (6)	0.1005 (3)	0.094 (2)
O2	0.3408 (4)	0.4506 (5)	0.3118 (2)	0.0598 (16)
O3	0.1502 (5)	0.2843 (6)	0.0464 (2)	0.098 (2)
S1	0.34334 (17)	0.50719 (19)	0.14035 (10)	0.0654 (8)
S2	0.23612 (19)	0.6865 (2)	0.12893 (11)	0.0729 (8)
S3	0.28013 (16)	0.36485 (17)	0.23861 (8)	0.0529 (6)
S4	0.29707 (16)	0.59039 (17)	0.24895 (8)	0.0542 (7)
S5	0.21376 (18)	0.29648 (19)	0.12809 (9)	0.0607 (7)
S6	0.1236 (2)	0.4658 (3)	0.07649 (10)	0.0953 (11)
C1	0.3163 (8)	0.6260 (8)	0.1215 (4)	0.083 (3)
C2	0.3487 (9)	0.7728 (9)	0.0829 (4)	0.105 (3)
H2A	0.3602	0.8220	0.1069	0.126*
H2B	0.2932	0.7786	0.0681	0.126*
C3	0.3990 (9)	0.7922 (10)	0.0512 (5)	0.113 (2)	0.21 (3)
H3	0.4552	0.7758	0.0622	0.135*	0.21 (3)
C4	0.365 (3)	0.765 (2)	0.0033 (7)	0.115 (6)	0.21 (3)
H4A	0.3723	0.6941	−0.0011	0.173*	0.21 (3)
H4B	0.3907	0.8044	−0.0153	0.173*	0.21 (3)
H4C	0.3091	0.7806	−0.0040	0.173*	0.21 (3)
C3'	0.3990 (9)	0.7922 (10)	0.0512 (5)	0.113 (2)	0.79 (3)
H3'	0.4540	0.7902	0.0684	0.135*	0.79 (3)
C4'	0.3923 (13)	0.7138 (14)	0.0156 (6)	0.124 (5)	0.79 (3)
H4'1	0.3404	0.6839	0.0096	0.186*	0.79 (3)
H4'2	0.4313	0.6618	0.0251	0.186*	0.79 (3)
H4'3	0.4007	0.7453	−0.0109	0.186*	0.79 (3)
C5	0.3817 (9)	0.9009 (10)	0.0378 (5)	0.127 (3)
H5A	0.4138	0.9211	0.0179	0.191*
H5B	0.3934	0.9435	0.0637	0.191*
H5C	0.3268	0.9077	0.0232	0.191*
C6	0.3079 (6)	0.4716 (7)	0.2692 (3)	0.049 (2)
C7	0.3747 (7)	0.5298 (8)	0.3422 (3)	0.067 (2)
H7A	0.3378	0.5861	0.3401	0.081*
H7B	0.4229	0.5550	0.3352	0.081*
C8	0.3929 (7)	0.4857 (8)	0.3888 (3)	0.072 (2)
H8	0.4167	0.4182	0.3883	0.087*
C9	0.3159 (9)	0.4747 (10)	0.4027 (4)	0.103 (4)
H9A	0.2813	0.4306	0.3823	0.154*
H9B	0.2917	0.5403	0.4027	0.154*
H9C	0.3257	0.4460	0.4320	0.154*
C10	0.4482 (8)	0.5511 (10)	0.4195 (4)	0.106 (4)
H10A	0.4602	0.5209	0.4485	0.159*
H10B	0.4247	0.6168	0.4209	0.159*
H10C	0.4961	0.5585	0.4093	0.159*
C11	0.1600 (8)	0.3479 (10)	0.0808 (4)	0.091 (3)
C12	0.1127 (9)	0.3196 (10)	0.0031 (4)	0.107 (2)	0.442 (14)
H12A	0.1279	0.3898	−0.0002	0.128*	0.442 (14)
H12B	0.0557	0.3177	−0.0005	0.128*	0.442 (14)
C13	0.1355 (19)	0.2547 (17)	−0.0328 (7)	0.104 (3)	0.442 (14)
H13	0.1934	0.2540	−0.0274	0.125*	0.442 (14)
C14	0.107 (2)	0.1444 (14)	−0.0290 (9)	0.115 (5)	0.442 (14)
H14A	0.0800	0.1204	−0.0577	0.173*	0.442 (14)
H14B	0.0720	0.1425	−0.0092	0.173*	0.442 (14)
H14C	0.1521	0.1015	−0.0176	0.173*	0.442 (14)
C15	0.103 (2)	0.299 (2)	−0.0786 (6)	0.114 (5)	0.442 (14)
H15A	0.1023	0.2469	−0.1005	0.171*	0.442 (14)
H15B	0.1354	0.3544	−0.0836	0.171*	0.442 (14)
H15C	0.0497	0.3225	−0.0807	0.171*	0.442 (14)
C12'	0.1127 (9)	0.3196 (10)	0.0031 (4)	0.107 (2)	0.558 (14)
H12C	0.1494	0.3615	−0.0084	0.128*	0.558 (14)
H12D	0.0674	0.3614	0.0048	0.128*	0.558 (14)
C13'	0.0851 (18)	0.229 (2)	−0.0289 (8)	0.106 (3)	0.558 (14)
H13'	0.0480	0.1883	−0.0164	0.127*	0.558 (14)
C14'	0.1598 (17)	0.163 (2)	−0.0264 (8)	0.116 (5)	0.558 (14)
H14D	0.1480	0.1093	−0.0482	0.173*	0.558 (14)
H14E	0.1760	0.1330	0.0026	0.173*	0.558 (14)
H14F	0.2017	0.2043	−0.0321	0.173*	0.558 (14)
C15'	0.0449 (17)	0.261 (2)	−0.0701 (8)	0.118 (5)	0.558 (14)
H15D	0.0496	0.3337	−0.0720	0.176*	0.558 (14)
H15E	−0.0100	0.2431	−0.0747	0.176*	0.558 (14)
H15F	0.0669	0.2293	−0.0924	0.176*	0.558 (14)
C16	0.0861 (6)	0.7077 (8)	0.1849 (3)	0.055 (2)
H16	0.1332	0.7381	0.1824	0.066*
C17	0.0253 (6)	0.7700 (8)	0.1897 (3)	0.059 (2)
H17	0.0317	0.8404	0.1908	0.071*
C18	−0.0438 (6)	0.7277 (8)	0.1929 (3)	0.0588 (19)
H18	−0.0859	0.7691	0.1956	0.071*
C19	−0.0524 (6)	0.6226 (8)	0.1922 (3)	0.0527 (17)
C20	0.0127 (6)	0.5644 (8)	0.1877 (3)	0.0512 (16)
C21	0.0080 (6)	0.4540 (8)	0.1888 (3)	0.0522 (16)
C22	−0.0626 (6)	0.4087 (8)	0.1940 (3)	0.0542 (18)
C23	−0.0641 (6)	0.3038 (8)	0.1966 (3)	0.0601 (19)
H23	−0.1100	0.2712	0.1997	0.072*
C24	−0.0010 (6)	0.2489 (8)	0.1946 (3)	0.063 (2)
H24	−0.0020	0.1784	0.1972	0.076*
C25	0.0671 (6)	0.2985 (8)	0.1887 (3)	0.059 (2)
H25	0.1107	0.2593	0.1867	0.071*
C26	−0.1232 (6)	0.5723 (8)	0.1958 (3)	0.0592 (18)
H26	−0.1672	0.6111	0.1975	0.071*
C27	−0.1280 (6)	0.4717 (8)	0.1968 (3)	0.0602 (18)
H27	−0.1752	0.4415	0.1993	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Bi1	0.0372 (2)	0.0447 (2)	0.0395 (2)	−0.00210 (16)	0.00663 (14)	−0.00030 (16)
N1	0.044 (5)	0.052 (5)	0.042 (5)	0.001 (4)	0.005 (4)	−0.003 (4)
N2	0.039 (5)	0.053 (5)	0.053 (5)	−0.007 (4)	0.009 (4)	0.006 (4)
O1	0.116 (5)	0.089 (4)	0.094 (4)	−0.012 (4)	0.061 (4)	0.017 (4)
O2	0.072 (4)	0.057 (3)	0.044 (3)	−0.001 (3)	0.001 (3)	−0.008 (3)
O3	0.127 (5)	0.116 (5)	0.047 (4)	−0.031 (4)	0.010 (4)	−0.017 (4)
S1	0.0583 (17)	0.0622 (17)	0.086 (2)	0.0000 (13)	0.0366 (16)	0.0007 (14)
S2	0.077 (2)	0.0610 (17)	0.088 (2)	0.0094 (15)	0.0338 (18)	0.0165 (15)
S3	0.0597 (17)	0.0440 (13)	0.0493 (15)	0.0087 (12)	0.0010 (13)	−0.0042 (11)
S4	0.0663 (18)	0.0423 (13)	0.0498 (15)	−0.0067 (12)	0.0045 (13)	0.0000 (11)
S5	0.075 (2)	0.0567 (15)	0.0494 (16)	−0.0082 (14)	0.0132 (14)	−0.0101 (12)
S6	0.126 (3)	0.089 (2)	0.0528 (19)	0.000 (2)	−0.0182 (19)	0.0058 (16)
C1	0.105 (6)	0.078 (5)	0.081 (5)	−0.013 (5)	0.055 (5)	0.013 (4)
C2	0.127 (6)	0.097 (5)	0.103 (5)	−0.014 (5)	0.051 (5)	0.029 (5)
C3	0.131 (5)	0.105 (4)	0.111 (5)	−0.005 (4)	0.047 (4)	0.024 (4)
C4	0.136 (10)	0.112 (10)	0.107 (10)	−0.001 (9)	0.047 (9)	0.025 (9)
C3'	0.131 (5)	0.105 (4)	0.111 (5)	−0.005 (4)	0.047 (4)	0.024 (4)
C4'	0.143 (9)	0.135 (9)	0.098 (8)	0.009 (8)	0.037 (8)	0.023 (8)
C5	0.145 (6)	0.122 (6)	0.123 (6)	−0.005 (5)	0.047 (5)	0.035 (5)
C6	0.051 (5)	0.056 (4)	0.041 (4)	−0.002 (4)	0.010 (4)	−0.009 (4)
C7	0.078 (5)	0.070 (5)	0.046 (4)	−0.013 (4)	−0.001 (4)	−0.015 (4)
C8	0.083 (5)	0.076 (5)	0.051 (4)	−0.013 (5)	0.000 (4)	−0.013 (4)
C9	0.116 (8)	0.112 (8)	0.075 (7)	−0.026 (7)	0.013 (7)	−0.005 (6)
C10	0.111 (8)	0.119 (8)	0.076 (7)	−0.007 (7)	−0.003 (7)	−0.019 (7)
C11	0.113 (6)	0.109 (6)	0.049 (5)	−0.038 (5)	0.012 (5)	−0.018 (4)
C12	0.127 (5)	0.127 (5)	0.059 (4)	−0.036 (5)	0.005 (4)	−0.018 (4)
C13	0.124 (6)	0.125 (6)	0.058 (5)	−0.036 (6)	0.008 (6)	−0.017 (5)
C14	0.133 (9)	0.134 (9)	0.070 (8)	−0.039 (9)	0.006 (8)	−0.018 (8)
C15	0.131 (9)	0.140 (9)	0.064 (8)	−0.035 (8)	0.007 (8)	−0.016 (8)
C12'	0.127 (5)	0.127 (5)	0.059 (4)	−0.036 (5)	0.005 (4)	−0.018 (4)
C13'	0.125 (6)	0.124 (6)	0.060 (5)	−0.036 (6)	0.006 (5)	−0.018 (5)
C14'	0.129 (9)	0.138 (9)	0.071 (7)	−0.044 (8)	0.006 (8)	−0.026 (8)
C15'	0.140 (9)	0.141 (8)	0.063 (8)	−0.046 (8)	0.004 (8)	−0.017 (8)
C16	0.044 (4)	0.068 (4)	0.051 (4)	0.000 (4)	0.007 (4)	−0.008 (4)
C17	0.051 (4)	0.071 (4)	0.054 (4)	0.004 (4)	0.010 (4)	−0.003 (4)
C18	0.048 (4)	0.075 (4)	0.053 (4)	0.009 (3)	0.010 (3)	−0.002 (3)
C19	0.041 (3)	0.075 (4)	0.044 (3)	0.000 (3)	0.011 (3)	0.004 (3)
C20	0.040 (3)	0.070 (3)	0.044 (3)	0.000 (3)	0.010 (3)	0.005 (3)
C21	0.042 (3)	0.073 (3)	0.043 (3)	−0.002 (3)	0.012 (3)	0.006 (3)
C22	0.042 (3)	0.073 (4)	0.047 (3)	−0.005 (3)	0.009 (3)	0.007 (3)
C23	0.047 (4)	0.079 (4)	0.055 (4)	−0.010 (3)	0.014 (3)	0.008 (3)
C24	0.055 (4)	0.073 (4)	0.061 (4)	−0.012 (4)	0.015 (4)	0.008 (4)
C25	0.049 (4)	0.070 (4)	0.059 (4)	−0.002 (4)	0.014 (4)	0.007 (4)
C26	0.044 (3)	0.081 (4)	0.054 (4)	0.003 (3)	0.012 (3)	0.005 (3)
C27	0.044 (3)	0.082 (4)	0.054 (3)	−0.004 (3)	0.011 (3)	0.008 (3)

Geometric parameters (Å, º)

Bi1—S1	2.720 (3)	C9—H9B	0.9600
Bi1—N2	2.762 (7)	C9—H9C	0.9600
Bi1—S3	2.779 (2)	C10—H10A	0.9600
Bi1—S5	2.792 (3)	C10—H10B	0.9600
Bi1—N1	2.811 (7)	C10—H10C	0.9600
Bi1—S6	2.867 (3)	C12—C13	1.524 (19)
Bi1—S4	2.981 (2)	C12—H12A	0.9700
Bi1—S2	2.986 (3)	C12—H12B	0.9700
N1—C16	1.323 (11)	C13—C15	1.517 (19)
N1—C20	1.361 (11)	C13—C14	1.543 (19)
N2—C25	1.324 (11)	C13—H13	0.9800
N2—C21	1.354 (11)	C14—H14A	0.9600
O1—C1	1.325 (12)	C14—H14B	0.9600
O1—C2	1.476 (13)	C14—H14C	0.9600
O2—C6	1.341 (10)	C15—H15A	0.9600
O2—C7	1.435 (11)	C15—H15B	0.9600
O3—C11	1.335 (13)	C15—H15C	0.9600
O3—C12	1.427 (14)	C13'—C15'	1.37 (3)
S1—C1	1.693 (12)	C13'—C14'	1.55 (4)
S2—C1	1.664 (13)	C13'—H13'	0.9800
S3—C6	1.698 (9)	C14'—H14D	0.9600
S4—C6	1.675 (9)	C14'—H14E	0.9600
S5—C11	1.685 (13)	C14'—H14F	0.9600
S6—C11	1.666 (14)	C15'—H15D	0.9600
C2—C3	1.480 (13)	C15'—H15E	0.9600
C2—H2A	0.9700	C15'—H15F	0.9600
C2—H2B	0.9700	C16—C17	1.370 (12)
C3—C5	1.498 (17)	C16—H16	0.9300
C3—C4	1.51 (2)	C17—C18	1.346 (13)
C3—H3	0.9800	C17—H17	0.9300
C4—H4A	0.9600	C18—C19	1.388 (13)
C4—H4B	0.9600	C18—H18	0.9300
C4—H4C	0.9600	C19—C20	1.397 (13)
C4'—H4'1	0.9600	C19—C26	1.423 (13)
C4'—H4'2	0.9600	C20—C21	1.453 (14)
C4'—H4'3	0.9600	C21—C22	1.405 (12)
C5—H5A	0.9600	C22—C23	1.381 (13)
C5—H5B	0.9600	C22—C27	1.423 (13)
C5—H5C	0.9600	C23—C24	1.323 (13)
C7—C8	1.520 (12)	C23—H23	0.9300
C7—H7A	0.9700	C24—C25	1.400 (13)
C7—H7B	0.9700	C24—H24	0.9300
C8—C10	1.464 (15)	C25—H25	0.9300
C8—C9	1.502 (17)	C26—C27	1.324 (13)
C8—H8	0.9800	C26—H26	0.9300
C9—H9A	0.9600	C27—H27	0.9300
S1—Bi1—N2	160.63 (17)	C9—C8—H8	109.0
S1—Bi1—S3	91.46 (9)	C7—C8—H8	109.0
N2—Bi1—S3	81.85 (16)	C8—C9—H9A	109.5
S1—Bi1—S5	79.66 (8)	C8—C9—H9B	109.5
N2—Bi1—S5	81.12 (17)	H9A—C9—H9B	109.5
S3—Bi1—S5	77.03 (8)	C8—C9—H9C	109.5
S1—Bi1—N1	139.45 (16)	H9A—C9—H9C	109.5
N2—Bi1—N1	58.9 (2)	H9B—C9—H9C	109.5
S3—Bi1—N1	114.62 (15)	C8—C10—H10A	109.5
S5—Bi1—N1	134.24 (16)	C8—C10—H10B	109.5
S1—Bi1—S6	88.74 (11)	H10A—C10—H10B	109.5
N2—Bi1—S6	84.76 (17)	C8—C10—H10C	109.5
S3—Bi1—S6	139.50 (8)	H10A—C10—H10C	109.5
S5—Bi1—S6	63.18 (9)	H10B—C10—H10C	109.5
N1—Bi1—S6	89.91 (16)	O3—C11—S6	122.7 (10)
S1—Bi1—S4	83.37 (8)	O3—C11—S5	112.8 (10)
N2—Bi1—S4	109.01 (16)	S6—C11—S5	124.5 (7)
S3—Bi1—S4	62.33 (7)	O3—C12—C13	111.4 (14)
S5—Bi1—S4	135.29 (8)	O3—C12—H12A	109.4
N1—Bi1—S4	82.47 (15)	C13—C12—H12A	109.4
S6—Bi1—S4	157.22 (8)	O3—C12—H12B	109.4
S1—Bi1—S2	62.57 (8)	C13—C12—H12B	109.4
N2—Bi1—S2	132.88 (17)	H12A—C12—H12B	108.0
S3—Bi1—S2	136.95 (9)	C15—C13—C12	111.4 (18)
S5—Bi1—S2	125.43 (8)	C15—C13—C14	111.8 (17)
N1—Bi1—S2	77.61 (16)	C12—C13—C14	109.2 (17)
S6—Bi1—S2	77.36 (10)	C15—C13—H13	108.1
S4—Bi1—S2	80.05 (8)	C12—C13—H13	108.1
C16—N1—C20	116.8 (8)	C14—C13—H13	108.1
C16—N1—Bi1	122.1 (6)	C15'—C13'—C14'	117 (2)
C20—N1—Bi1	121.0 (6)	C15'—C13'—H13'	107.3
C25—N2—C21	117.1 (8)	C14'—C13'—H13'	107.3
C25—N2—Bi1	120.1 (6)	C13'—C14'—H14D	109.5
C21—N2—Bi1	122.6 (6)	C13'—C14'—H14E	109.5
C1—O1—C2	118.1 (9)	H14D—C14'—H14E	109.5
C6—O2—C7	120.9 (7)	C13'—C14'—H14F	109.5
C11—O3—C12	119.7 (10)	H14D—C14'—H14F	109.5
C1—S1—Bi1	90.4 (4)	H14E—C14'—H14F	109.5
C1—S2—Bi1	82.2 (4)	C13'—C15'—H15D	109.5
C6—S3—Bi1	89.3 (3)	C13'—C15'—H15E	109.5
C6—S4—Bi1	83.2 (3)	H15D—C15'—H15E	109.5
C11—S5—Bi1	87.2 (4)	C13'—C15'—H15F	109.5
C11—S6—Bi1	85.0 (4)	H15D—C15'—H15F	109.5
O1—C1—S2	122.0 (9)	H15E—C15'—H15F	109.5
O1—C1—S1	113.5 (9)	N1—C16—C17	124.2 (10)
S2—C1—S1	124.5 (6)	N1—C16—H16	117.9
O1—C2—C3	107.5 (10)	C17—C16—H16	117.9
O1—C2—H2A	110.2	C18—C17—C16	118.9 (10)
C3—C2—H2A	110.2	C18—C17—H17	120.5
O1—C2—H2B	110.2	C16—C17—H17	120.5
C3—C2—H2B	110.2	C17—C18—C19	120.2 (10)
H2A—C2—H2B	108.5	C17—C18—H18	119.9
C2—C3—C5	103.7 (11)	C19—C18—H18	119.9
C2—C3—C4	117.0 (17)	C18—C19—C20	117.4 (9)
C5—C3—C4	86.6 (12)	C18—C19—C26	123.5 (9)
C2—C3—H3	115.2	C20—C19—C26	119.2 (9)
C5—C3—H3	115.2	N1—C20—C19	122.5 (9)
C4—C3—H3	115.2	N1—C20—C21	118.0 (8)
H4'1—C4'—H4'2	109.5	C19—C20—C21	119.5 (9)
H4'1—C4'—H4'3	109.5	N2—C21—C22	122.6 (9)
H4'2—C4'—H4'3	109.5	N2—C21—C20	118.7 (8)
C3—C5—H5A	109.5	C22—C21—C20	118.7 (9)
C3—C5—H5B	109.5	C23—C22—C21	117.2 (9)
H5A—C5—H5B	109.5	C23—C22—C27	123.4 (9)
C3—C5—H5C	109.5	C21—C22—C27	119.4 (9)
H5A—C5—H5C	109.5	C24—C23—C22	121.0 (10)
H5B—C5—H5C	109.5	C24—C23—H23	119.5
O2—C6—S4	123.1 (7)	C22—C23—H23	119.5
O2—C6—S3	112.4 (7)	C23—C24—C25	119.1 (10)
S4—C6—S3	124.5 (6)	C23—C24—H24	120.5
O2—C7—C8	108.1 (8)	C25—C24—H24	120.5
O2—C7—H7A	110.1	N2—C25—C24	123.1 (10)
C8—C7—H7A	110.1	N2—C25—H25	118.4
O2—C7—H7B	110.1	C24—C25—H25	118.4
C8—C7—H7B	110.1	C27—C26—C19	121.6 (10)
H7A—C7—H7B	108.4	C27—C26—H26	119.2
C10—C8—C9	111.4 (10)	C19—C26—H26	119.2
C10—C8—C7	110.7 (10)	C26—C27—C22	121.6 (10)
C9—C8—C7	107.8 (10)	C26—C27—H27	119.2
C10—C8—H8	109.0	C22—C27—H27	119.2