Tris(ethylxanthato-κ2S,S′)(1,10-phen­anthroline)bis­muth(III)

Li, F.; Yin, H.-D.; Zhai, J.; Wang, D.-Q.

doi:10.1107/S1600536807020338

Tris(ethylxanthato-κ²S,S′)(1,10-phenanthroline)bismuth(III)

F. Li, H.-D. Yin, J. Zhai and D.-Q. Wang

The title compound, [Bi(C₃H₅OS₂)₃(C₁₂H₈N₂)] [systematic name: tris(ethoxymethanedithioato-κ²S,S′)(1,10-phenanthroline)bismuth(III)], is monomeric, with the Bi atom chelated by the S atoms of three ethylxanthate ligands and the N atoms of 1,10-phenanthroline. The central Bi^III atom is eight-coordinate and adopts a distorted capped-pentagonal–bipyramidal geometry. In the crystal structure, weak C—H

S interactions and a close S

S contact stabilize the structure [S

S = 3.509 (3) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020338/sj2303sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020338/sj2303Isup2.hkl Contains datablock I

CCDC reference: 284314

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.028 Å
R factor = 0.068
wR factor = 0.191
Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT342_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         28

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.77
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         200 Deg.
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Bi1    -   S3      ..       6.09 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Bi1    -   S6      ..       8.29 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
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
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B    ..  S3      ..       2.90 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20    ..  S2      ..       2.99 Ang.

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      0.774
            Tmax scaled      0.282 Tmin scaled      0.269

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

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

Comment top

There has recently been increasing interest in bismuth(III) coordination chemistry, particularly in the light of the role of bismuth compounds in ²¹²Bi isotope therapy in cancer research (Sun et al., 1997) and the use of bismuth complexes in the treatment of peptic ulcers (Baxter et al., 1992). In particular, the interaction of bismuth(III) salts with chelating nitrogen-base ligands has been actively studied. In view of above and persuance of our interest in sulfur-containing ligands (Li et al., 2005), we report here the synthesis and structure of the title compound, (I).

In this complex the bismuth atom is eight-coordinated by sulfur atoms belonging to three bidenate ethylxanthate ligands and by the nitrogen atoms of the bidentate 1,10-phenanthroline. The central Bi atom is eight-coordinate with atoms S4 and N1 in axial positions, and atoms S1, S2, S3, S5 and S6 in the equatorial plane. The remaining N atom (N2) of the 1,10-phenanthroline ligand caps the S2/S5/N1 face, giving a highly distorted capped pentagonal bipyramidal coordination geometry. Three Bi—S bonds [to S2, S3 and S5; mean = 2.897 Å] are significantly longer than the others [to S1, S4 and S6; mean = 2.805 Å], suggesting some delocalization in the system. In addition, the chelating phenanthroline ligands are bonded to the Bi atom through two N atoms. The Bi1—N1 and Bi1—N2 distances fall in the same range as in other Bi/N complexes (Li et al., 2005).

The structure is stabilized by weak C—H···S interactions, Table 1, and a close S2···S2ⁱ contact 3.496 Å, i = 1 - x, 1 - y, 1 - z.

Related literature top

For uses of Bi^III complexes, see: Sun et al. (1997) and Baxter (1992). For related Bi^III compounds with xanthate ligands, see, for example, Snow & Tiekink (1987) and Hoskins et al. (1985), and with phenanthroline ligands, see, for example, Li et al. (2005).

Experimental top

To a stirred solution of BiI₃ (0.2 mmol) in acetonitrile (20 ml), C₂H₅OCS₂Na (0.6 mmol) was added. The reaction mixture was stirred for 2.5 h at 298 K. An orange solution was obtained and then filtered. The solvent was gradually removed by evaporation under vacuum to give a solid product which was recrystallized from ethanol yielding orange-red crystals of (I).

Structure description top

The structure is stabilized by weak C—H···S interactions, Table 1, and a close S2···S2ⁱ contact 3.496 Å, i = 1 - x, 1 - y, 1 - z.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of the title complex, showing 30% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity.
	Fig. 2. Crystal packing of the title complex. The S···S interaction is shown as a dashed line.

tris(ethoxymethanedithioato-κ²S,S')(1,10-phenanthroline)bismuth(III), top

Crystal data top

[Bi(C₃H₅OS₂)₃(C₁₂H₈N₂)]	Z = 2
M_r = 752.75	F(000) = 732
Triclinic, P1	D_x = 1.857 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.7569 (16) Å	Cell parameters from 2951 reflections
b = 11.1985 (17) Å	θ = 2.4–24.6°
c = 11.2494 (17) Å	µ = 7.04 mm⁻¹
α = 96.306 (2)°	T = 298 K
β = 91.127 (2)°	Block, orange-red
γ = 91.737 (2)°	0.19 × 0.18 × 0.18 mm
V = 1345.9 (4) Å³

Data collection top

Siemens SMART CCD area-detector diffractometer	4698 independent reflections
Radiation source: fine-focus sealed tube	3872 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.348, T_max = 0.364	k = −11→13
7132 measured reflections	l = −13→13

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.191	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1041P)² + 18.5625P] where P = (F_o² + 2F_c²)/3
4698 reflections	(Δ/σ)_max = 0.001
298 parameters	Δρ_max = 2.99 e Å⁻³
551 restraints	Δρ_min = −3.37 e Å⁻³

Crystal data top

[Bi(C₃H₅OS₂)₃(C₁₂H₈N₂)]	γ = 91.737 (2)°
M_r = 752.75	V = 1345.9 (4) Å³
Triclinic, P1	Z = 2
a = 10.7569 (16) Å	Mo Kα radiation
b = 11.1985 (17) Å	µ = 7.04 mm⁻¹
c = 11.2494 (17) Å	T = 298 K
α = 96.306 (2)°	0.19 × 0.18 × 0.18 mm
β = 91.127 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	4698 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3872 reflections with I > 2σ(I)
T_min = 0.348, T_max = 0.364	R_int = 0.020
7132 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	551 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1041P)² + 18.5625P] where P = (F_o² + 2F_c²)/3
4698 reflections	Δρ_max = 2.99 e Å⁻³
298 parameters	Δρ_min = −3.37 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Bi1	0.68014 (5)	0.26489 (5)	0.68287 (5)	0.0469 (2)
N1	0.9283 (13)	0.2752 (14)	0.6203 (14)	0.065 (4)
N2	0.8064 (13)	0.4878 (13)	0.6736 (13)	0.058 (3)
O1	0.5261 (14)	0.2467 (13)	0.2990 (10)	0.0870 (17)
O2	0.3121 (9)	0.3057 (9)	0.8709 (10)	0.059 (3)
O3	0.8331 (13)	0.0829 (12)	1.0024 (12)	0.0844 (17)
S1	0.6586 (6)	0.1155 (5)	0.4631 (5)	0.0859 (10)
S2	0.5384 (5)	0.3490 (5)	0.4953 (5)	0.0749 (9)
S3	0.5113 (4)	0.4325 (4)	0.8153 (4)	0.0614 (9)
S4	0.4617 (4)	0.1707 (4)	0.7510 (4)	0.0576 (9)
S5	0.7886 (5)	0.2739 (5)	0.9215 (5)	0.0744 (10)
S6	0.7602 (5)	0.0435 (5)	0.7627 (5)	0.0768 (10)
C1	0.5798 (19)	0.226 (2)	0.4120 (14)	0.0798 (13)
C2	0.556 (2)	0.1502 (16)	0.2132 (14)	0.0860 (18)
H2A	0.5239	0.0751	0.2376	0.103*
H2B	0.6459	0.1456	0.2079	0.103*
C3	0.500 (2)	0.170 (2)	0.0914 (12)	0.091 (4)
H3A	0.5227	0.1053	0.0330	0.137*
H3B	0.5310	0.2447	0.0683	0.137*
H3C	0.4111	0.1708	0.0962	0.137*
C4	0.4271 (12)	0.3071 (15)	0.8151 (15)	0.0565 (17)
C5	0.2697 (13)	0.4150 (12)	0.9345 (16)	0.062 (2)
H5A	0.2696	0.4785	0.8824	0.075*
H5B	0.3246	0.4402	1.0027	0.075*
C6	0.1380 (13)	0.3907 (17)	0.9765 (17)	0.073 (4)
H6A	0.1078	0.4627	1.0190	0.110*
H6B	0.1392	0.3282	1.0284	0.110*
H6C	0.0844	0.3661	0.9084	0.110*
C7	0.7962 (18)	0.1240 (18)	0.8926 (15)	0.0732 (16)
C8	0.834 (2)	−0.0378 (13)	1.0278 (15)	0.084 (2)
H8A	0.8944	−0.0816	0.9786	0.101*
H8B	0.7528	−0.0762	1.0105	0.101*
C9	0.869 (2)	−0.0387 (18)	1.1604 (15)	0.085 (3)
H9A	0.8659	−0.1200	1.1803	0.127*
H9B	0.8108	0.0078	1.2084	0.127*
H9C	0.9512	−0.0046	1.1758	0.127*
C10	0.9895 (19)	0.176 (2)	0.5929 (19)	0.077 (4)
H10	0.9457	0.1026	0.5832	0.093*
C11	1.1189 (19)	0.178 (2)	0.5778 (19)	0.080 (4)
H11	1.1592	0.1066	0.5582	0.096*
C12	1.183 (2)	0.279 (2)	0.5911 (19)	0.079 (4)
H12	1.2682	0.2788	0.5803	0.095*
C13	1.1268 (18)	0.386 (2)	0.6206 (17)	0.071 (3)
C14	0.9958 (16)	0.3812 (18)	0.6365 (16)	0.065 (3)
C15	0.9313 (17)	0.4899 (18)	0.6645 (16)	0.066 (3)
C16	1.0006 (19)	0.6024 (19)	0.6805 (17)	0.071 (4)
C17	0.927 (2)	0.713 (2)	0.7052 (19)	0.082 (4)
H17	0.9666	0.7882	0.7168	0.098*
C18	0.810 (2)	0.7007 (19)	0.7100 (18)	0.078 (4)
H18	0.7633	0.7693	0.7238	0.093*
C19	0.748 (2)	0.5882 (17)	0.6955 (17)	0.070 (4)
H19	0.6617	0.5847	0.7016	0.084*
C20	1.1907 (19)	0.500 (2)	0.6358 (19)	0.079 (4)
H20	1.2761	0.5034	0.6250	0.094*
C21	1.132 (2)	0.602 (2)	0.6652 (19)	0.080 (4)
H21	1.1772	0.6744	0.6758	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Bi1	0.0363 (3)	0.0425 (3)	0.0620 (4)	0.0043 (2)	0.0022 (2)	0.0048 (2)
N1	0.044 (8)	0.066 (9)	0.084 (10)	0.011 (7)	0.008 (7)	0.009 (8)
N2	0.050 (8)	0.054 (8)	0.073 (9)	0.000 (6)	0.005 (7)	0.011 (7)
O1	0.082 (3)	0.093 (3)	0.084 (3)	−0.004 (3)	−0.006 (3)	0.001 (3)
O2	0.044 (6)	0.062 (7)	0.070 (7)	0.000 (5)	0.009 (5)	0.003 (6)
O3	0.075 (3)	0.079 (3)	0.101 (3)	0.006 (3)	−0.003 (3)	0.022 (3)
S1	0.083 (2)	0.083 (2)	0.0848 (16)	0.0011 (17)	−0.0008 (18)	−0.0202 (15)
S2	0.0680 (19)	0.0842 (19)	0.0747 (17)	0.0015 (16)	−0.0100 (14)	0.0212 (15)
S3	0.0544 (18)	0.0551 (18)	0.0737 (19)	0.0008 (15)	0.0079 (16)	0.0006 (16)
S4	0.0477 (17)	0.0510 (17)	0.0740 (19)	0.0001 (15)	0.0071 (16)	0.0064 (16)
S5	0.073 (2)	0.077 (2)	0.0748 (14)	0.0058 (18)	−0.0127 (16)	0.0148 (16)
S6	0.068 (2)	0.0621 (19)	0.102 (2)	0.0078 (17)	−0.0019 (18)	0.0134 (18)
C1	0.073 (3)	0.095 (3)	0.0685 (17)	−0.016 (2)	−0.010 (2)	0.0006 (19)
C2	0.080 (3)	0.093 (3)	0.082 (3)	−0.004 (3)	−0.005 (3)	−0.001 (3)
C3	0.086 (6)	0.101 (7)	0.084 (6)	−0.004 (6)	−0.008 (6)	−0.001 (6)
C4	0.047 (3)	0.053 (3)	0.069 (3)	0.003 (3)	0.006 (3)	0.003 (3)
C5	0.054 (4)	0.060 (4)	0.071 (4)	0.003 (4)	0.008 (4)	−0.001 (4)
C6	0.060 (7)	0.079 (7)	0.079 (7)	0.006 (6)	0.013 (6)	−0.001 (7)
C7	0.064 (3)	0.068 (3)	0.089 (3)	0.006 (3)	−0.004 (3)	0.017 (3)
C8	0.074 (4)	0.076 (4)	0.102 (4)	0.005 (4)	−0.003 (4)	0.016 (4)
C9	0.074 (6)	0.084 (6)	0.098 (6)	0.003 (6)	−0.004 (6)	0.022 (6)
C10	0.062 (8)	0.091 (9)	0.083 (8)	0.015 (8)	0.011 (7)	0.025 (8)
C11	0.063 (8)	0.103 (9)	0.080 (8)	0.025 (8)	0.011 (7)	0.028 (8)
C12	0.060 (7)	0.106 (9)	0.076 (7)	0.005 (7)	0.005 (7)	0.028 (7)
C13	0.057 (7)	0.096 (8)	0.066 (7)	0.000 (6)	0.001 (6)	0.031 (7)
C14	0.051 (6)	0.085 (7)	0.064 (7)	−0.003 (6)	0.002 (6)	0.029 (6)
C15	0.060 (7)	0.079 (7)	0.063 (6)	−0.018 (6)	0.002 (6)	0.023 (6)
C16	0.069 (7)	0.082 (7)	0.064 (7)	−0.017 (7)	−0.002 (6)	0.022 (6)
C17	0.089 (8)	0.076 (8)	0.078 (8)	−0.024 (8)	0.001 (8)	0.011 (7)
C18	0.088 (9)	0.069 (8)	0.077 (8)	−0.007 (8)	0.005 (8)	0.011 (7)
C19	0.073 (8)	0.065 (8)	0.074 (8)	−0.005 (7)	0.006 (7)	0.021 (7)
C20	0.060 (7)	0.102 (8)	0.076 (7)	−0.016 (7)	−0.005 (6)	0.026 (7)
C21	0.070 (7)	0.093 (8)	0.078 (7)	−0.027 (7)	−0.004 (7)	0.023 (7)

Geometric parameters (Å, º) top

Bi1—S4	2.706 (4)	C5—H5A	0.9700
Bi1—N1	2.776 (14)	C5—H5B	0.9700
Bi1—N2	2.819 (14)	C6—H6A	0.9600
Bi1—S1	2.830 (5)	C6—H6B	0.9600
Bi1—S2	2.839 (5)	C6—H6C	0.9600
Bi1—S6	2.878 (5)	C8—C9	1.532 (11)
Bi1—S5	2.896 (5)	C8—H8A	0.9700
Bi1—S3	2.956 (5)	C8—H8B	0.9700
N1—C10	1.32 (2)	C9—H9A	0.9600
N1—C14	1.37 (2)	C9—H9B	0.9600
N2—C19	1.31 (2)	C9—H9C	0.9600
N2—C15	1.35 (2)	C10—C11	1.41 (3)
O1—C2	1.417 (11)	C10—H10	0.9300
O1—C1	1.432 (10)	C11—C12	1.30 (3)
O2—C4	1.399 (10)	C11—H11	0.9300
O2—C5	1.440 (10)	C12—C13	1.37 (3)
O3—C8	1.412 (10)	C12—H12	0.9300
O3—C7	1.418 (10)	C13—C20	1.42 (3)
S1—C1	1.67 (2)	C13—C14	1.42 (3)
S2—C1	1.66 (2)	C14—C15	1.43 (3)
S3—C4	1.648 (16)	C15—C16	1.44 (3)
S4—C4	1.671 (17)	C16—C21	1.42 (3)
S5—C7	1.68 (2)	C16—C17	1.49 (3)
S6—C7	1.66 (2)	C17—C18	1.27 (3)
C2—C3	1.527 (11)	C17—H17	0.9300
C2—H2A	0.9700	C18—C19	1.40 (3)
C2—H2B	0.9700	C18—H18	0.9300
C3—H3A	0.9600	C19—H19	0.9300
C3—H3B	0.9600	C20—C21	1.34 (3)
C3—H3C	0.9600	C20—H20	0.9300
C5—C6	1.528 (10)	C21—H21	0.9300

S4—Bi1—N1	158.8 (3)	O2—C5—H5A	110.1
S4—Bi1—N2	141.0 (3)	C6—C5—H5A	110.1
N1—Bi1—N2	59.3 (4)	O2—C5—H5B	110.1
S4—Bi1—S1	89.76 (16)	C6—C5—H5B	110.1
N1—Bi1—S1	82.0 (4)	H5A—C5—H5B	108.4
N2—Bi1—S1	115.4 (3)	C5—C6—H6A	109.5
S4—Bi1—S2	85.59 (15)	C5—C6—H6B	109.5
N1—Bi1—S2	107.4 (3)	H6A—C6—H6B	109.5
N2—Bi1—S2	81.2 (3)	C5—C6—H6C	109.5
S1—Bi1—S2	62.52 (18)	H6A—C6—H6C	109.5
S4—Bi1—S6	79.10 (15)	H6B—C6—H6C	109.5
N1—Bi1—S6	80.3 (3)	O3—C7—S6	128.5 (15)
N2—Bi1—S6	131.5 (3)	O3—C7—S5	105.5 (13)
S1—Bi1—S6	80.86 (18)	S6—C7—S5	125.9 (9)
S2—Bi1—S6	140.30 (17)	O3—C8—C9	108.3 (10)
S4—Bi1—S5	92.46 (15)	O3—C8—H8A	110.0
N1—Bi1—S5	82.3 (4)	C9—C8—H8A	110.0
N2—Bi1—S5	85.4 (3)	O3—C8—H8B	110.0
S1—Bi1—S5	141.62 (18)	C9—C8—H8B	110.0
S2—Bi1—S5	155.84 (17)	H8A—C8—H8B	108.4
S6—Bi1—S5	62.06 (16)	C8—C9—H9A	109.5
S4—Bi1—S3	63.13 (13)	C8—C9—H9B	109.5
N1—Bi1—S3	135.0 (3)	H9A—C9—H9B	109.5
N2—Bi1—S3	78.2 (3)	C8—C9—H9C	109.5
S1—Bi1—S3	133.69 (16)	H9A—C9—H9C	109.5
S2—Bi1—S3	77.74 (15)	H9B—C9—H9C	109.5
S6—Bi1—S3	124.66 (15)	N1—C10—C11	122 (2)
S5—Bi1—S3	79.91 (15)	N1—C10—H10	119.0
C10—N1—C14	117.5 (17)	C11—C10—H10	119.0
C10—N1—Bi1	120.9 (13)	C12—C11—C10	121 (2)
C14—N1—Bi1	120.8 (12)	C12—C11—H11	119.7
C19—N2—C15	120.2 (16)	C10—C11—H11	119.7
C19—N2—Bi1	120.4 (12)	C11—C12—C13	121 (2)
C15—N2—Bi1	118.7 (12)	C11—C12—H12	119.3
C2—O1—C1	108.3 (14)	C13—C12—H12	119.3
C4—O2—C5	119.1 (11)	C12—C13—C20	124.3 (19)
C8—O3—C7	126.5 (15)	C12—C13—C14	117 (2)
C1—S1—Bi1	86.4 (7)	C20—C13—C14	119 (2)
C1—S2—Bi1	86.2 (6)	N1—C14—C13	121.8 (19)
C4—S3—Bi1	81.0 (5)	N1—C14—C15	118.4 (16)
C4—S4—Bi1	88.8 (4)	C13—C14—C15	119.7 (18)
C7—S5—Bi1	85.4 (5)	N2—C15—C14	120.7 (16)
C7—S6—Bi1	86.3 (6)	N2—C15—C16	120.1 (19)
O1—C1—S2	100.1 (13)	C14—C15—C16	119.2 (18)
O1—C1—S1	135.4 (16)	C21—C16—C15	119 (2)
S2—C1—S1	124.5 (9)	C21—C16—C17	124.7 (19)
O1—C2—C3	109.7 (10)	C15—C16—C17	116.5 (18)
O1—C2—H2A	109.7	C18—C17—C16	118 (2)
C3—C2—H2A	109.7	C18—C17—H17	120.8
O1—C2—H2B	109.7	C16—C17—H17	120.8
C3—C2—H2B	109.7	C17—C18—C19	122 (2)
H2A—C2—H2B	108.2	C17—C18—H18	118.8
C2—C3—H3A	109.5	C19—C18—H18	118.8
C2—C3—H3B	109.5	N2—C19—C18	122 (2)
H3A—C3—H3B	109.5	N2—C19—H19	118.8
C2—C3—H3C	109.5	C18—C19—H19	118.8
H3A—C3—H3C	109.5	C21—C20—C13	122 (2)
H3B—C3—H3C	109.5	C21—C20—H20	119.0
O2—C4—S3	121.3 (12)	C13—C20—H20	119.0
O2—C4—S4	111.7 (11)	C20—C21—C16	122 (2)
S3—C4—S4	127.0 (7)	C20—C21—H21	119.2
O2—C5—C6	108.0 (9)	C16—C21—H21	119.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···S4ⁱ	0.97	2.78	3.660 (19)	152
C5—H5B···S3ⁱⁱ	0.97	2.90	3.851 (17)	167
C20—H20···S2ⁱⁱⁱ	0.93	2.99	3.73 (2)	138

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

Experimental details

Crystal data
Chemical formula	[Bi(C₃H₅OS₂)₃(C₁₂H₈N₂)]
M_r	752.75
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.7569 (16), 11.1985 (17), 11.2494 (17)
α, β, γ (°)	96.306 (2), 91.127 (2), 91.737 (2)
V (Å³)	1345.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	7.04
Crystal size (mm)	0.19 × 0.18 × 0.18

Data collection
Diffractometer	Siemens SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.348, 0.364
No. of measured, independent and observed [I > 2σ(I)] reflections	7132, 4698, 3872
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.191, 1.04
No. of reflections	4698
No. of parameters	298
No. of restraints	551
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.1041P)² + 18.5625P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.99, −3.37

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.