Iodo­(1,10-phenanthroline)bis­(pyrrolidine-1-dithio­carboxyl­ato-κ²S,S′)bis­muth(III)

The title compound, [Bi(C₄H₈NS₂)₂I(C₁₂H₈N₂)], is monomeric, with the Bi atom chelated by the S atoms of two pyrrolidine-1-dithio­carboxyl­ate ligands and both N atoms of one 1,10-phenanthroline ligand. An iodide ligand completes the coordination, with the seven-coordinate Bi atom adopting a highly distorted capped octa­hedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.014 Å
• Disorder in main residue
• R factor = 0.037
• wR factor = 0.108
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.74
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Bi1
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         14
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

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      0.737
            Tmax scaled      0.247 Tmin scaled      0.204

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 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
   3 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 (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); 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.

Iodo(1,10-phenanthroline)bis(pyrrolidine-1-dithiocarboxylato- κ²S,S')bismuth(III)

Crystal data

[Bi(C4H8NS2)2I(C12H8N2)]	Z = 2
Mr = 808.57	F(000) = 768
Triclinic, P1	Dx = 2.043 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.284 (12) Å	Cell parameters from 2400 reflections
b = 10.560 (13) Å	θ = 2.5–24.0°
c = 13.545 (16) Å	µ = 8.22 mm^−1
α = 79.155 (17)°	T = 298 K
β = 84.521 (17)°	Block, yellow
γ = 65.523 (14)°	0.21 × 0.18 × 0.17 mm
V = 1315 (3) Å^3

Data collection

Siemens SMART CCD diffractometer	4560 independent reflections
Radiation source: fine-focus sealed tube	3642 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
Tmin = 0.277, Tmax = 0.336	k = −12→12
6845 measured reflections	l = −14→16

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0604P)^2] where P = (Fo^2 + 2Fc^2)/3
4560 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 1.17 e Å^−3
170 restraints	Δρmin = −1.11 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	0.80538 (3)	0.83432 (3)	0.72823 (2)	0.04285 (13)
I1	1.05252 (6)	0.61803 (6)	0.61083 (5)	0.06093 (19)
N1	0.6529 (7)	0.6406 (7)	1.0106 (5)	0.0498 (17)
N2	1.0349 (7)	1.0762 (7)	0.8292 (6)	0.0495 (17)
N3	0.5404 (7)	1.0240 (7)	0.6470 (5)	0.0413 (15)
N4	0.6326 (7)	0.7393 (7)	0.6498 (5)	0.0431 (16)
S1	0.8498 (2)	0.5975 (2)	0.86559 (17)	0.0507 (5)
S2	0.6070 (3)	0.8732 (2)	0.88093 (17)	0.0572 (6)
S3	1.0055 (3)	0.8381 (2)	0.8418 (2)	0.0671 (7)
S4	0.8235 (3)	1.1060 (3)	0.7191 (2)	0.0760 (9)
C1	0.6971 (8)	0.6994 (8)	0.9283 (6)	0.045 (2)
C2	0.7245 (11)	0.4941 (11)	1.0572 (7)	0.068 (2)	0.48 (4)
H2A	0.8248	0.4692	1.0673	0.082*	0.48 (4)
H2B	0.7161	0.4311	1.0169	0.082*	0.48 (4)
C3	0.644 (3)	0.489 (4)	1.1572 (18)	0.076 (5)	0.48 (4)
H3A	0.6423	0.3970	1.1789	0.091*	0.48 (4)
H3B	0.6884	0.5097	1.2086	0.091*	0.48 (4)
C4	0.493 (4)	0.601 (3)	1.139 (2)	0.075 (5)	0.48 (4)
H4A	0.4459	0.6332	1.2004	0.091*	0.48 (4)
H4B	0.4352	0.5672	1.1074	0.091*	0.48 (4)
C5	0.5208 (11)	0.7179 (11)	1.0673 (8)	0.072 (2)	0.48 (4)
H5A	0.4416	0.7724	1.0222	0.087*	0.48 (4)
H5B	0.5356	0.7808	1.1043	0.087*	0.48 (4)
C2'	0.7245 (11)	0.4941 (11)	1.0572 (7)	0.068 (2)	0.52 (4)
H2'1	0.8081	0.4796	1.0929	0.082*	0.52 (4)
H2'2	0.7533	0.4321	1.0073	0.082*	0.52 (4)
C3'	0.611 (3)	0.468 (3)	1.130 (2)	0.072 (5)	0.52 (4)
H3'1	0.5415	0.4514	1.0964	0.086*	0.52 (4)
H3'2	0.6530	0.3899	1.1847	0.086*	0.52 (4)
C4'	0.547 (4)	0.607 (3)	1.166 (2)	0.078 (5)	0.52 (4)
H4'1	0.6130	0.6146	1.2091	0.093*	0.52 (4)
H4'2	0.4585	0.6193	1.2030	0.093*	0.52 (4)
C5'	0.5208 (11)	0.7179 (11)	1.0673 (8)	0.072 (2)	0.52 (4)
H5'1	0.4349	0.7332	1.0339	0.087*	0.52 (4)
H5'2	0.5166	0.8072	1.0793	0.087*	0.52 (4)
C6	0.9605 (9)	1.0140 (9)	0.7992 (7)	0.050 (2)
C7	1.0032 (9)	1.2261 (9)	0.8014 (8)	0.058 (2)
H7A	0.9053	1.2832	0.8192	0.070*
H7B	1.0185	1.2505	0.7298	0.070*
C8	1.1083 (10)	1.2456 (10)	0.8623 (9)	0.067 (3)
H8A	1.1395	1.3167	0.8256	0.080*
H8B	1.0656	1.2734	0.9260	0.080*
C9	1.2266 (11)	1.1084 (11)	0.8775 (9)	0.067 (3)
H9A	1.2791	1.0969	0.9367	0.081*
H9B	1.2914	1.0970	0.8198	0.081*
C10	1.1607 (10)	1.0021 (10)	0.8912 (8)	0.063 (3)
H10A	1.2250	0.9158	0.8674	0.076*
H10B	1.1349	0.9799	0.9610	0.076*
C11	0.4956 (9)	1.1607 (9)	0.6443 (6)	0.050 (2)
H11	0.5591	1.1947	0.6616	0.060*
C12	0.3565 (9)	1.2586 (9)	0.6165 (7)	0.053 (2)
H12	0.3298	1.3545	0.6151	0.063*
C13	0.2613 (9)	1.2103 (10)	0.5917 (6)	0.053 (2)
H13	0.1688	1.2725	0.5733	0.064*
C14	0.3067 (8)	1.0642 (9)	0.5947 (6)	0.0448 (19)
C15	0.4478 (8)	0.9736 (8)	0.6230 (5)	0.0379 (17)
C16	0.4970 (8)	0.8252 (8)	0.6234 (6)	0.0388 (18)
C17	0.4034 (9)	0.7711 (9)	0.5975 (6)	0.049 (2)
C18	0.4533 (10)	0.6299 (10)	0.5945 (7)	0.058 (2)
H18	0.3932	0.5926	0.5763	0.069*
C19	0.5938 (11)	0.5429 (10)	0.6188 (7)	0.057 (2)
H19	0.6297	0.4468	0.6170	0.068*
C20	0.6800 (10)	0.6025 (9)	0.6459 (6)	0.050 (2)
H20	0.7745	0.5445	0.6619	0.060*
C21	0.2139 (10)	1.0059 (12)	0.5701 (8)	0.065 (3)
H21	0.1200	1.0650	0.5530	0.078*
C22	0.2597 (10)	0.8687 (12)	0.5711 (7)	0.062 (3)
H22	0.1967	0.8340	0.5540	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Bi1	0.03717 (19)	0.03008 (18)	0.0540 (2)	−0.00539 (13)	−0.00870 (14)	−0.00552 (13)
I1	0.0395 (3)	0.0458 (4)	0.0908 (5)	−0.0077 (3)	0.0015 (3)	−0.0197 (3)
N1	0.044 (4)	0.043 (4)	0.045 (4)	−0.002 (3)	−0.003 (3)	−0.003 (3)
N2	0.035 (4)	0.034 (4)	0.071 (5)	−0.003 (3)	−0.010 (3)	−0.010 (3)
N3	0.036 (4)	0.034 (4)	0.047 (4)	−0.007 (3)	−0.014 (3)	0.000 (3)
N4	0.048 (4)	0.031 (4)	0.046 (4)	−0.013 (3)	−0.001 (3)	−0.005 (3)
S1	0.0440 (12)	0.0309 (11)	0.0599 (14)	0.0003 (9)	−0.0030 (10)	−0.0027 (9)
S2	0.0575 (14)	0.0363 (12)	0.0536 (14)	0.0038 (10)	−0.0046 (11)	−0.0029 (10)
S3	0.0694 (16)	0.0371 (13)	0.0896 (19)	−0.0146 (12)	−0.0425 (14)	0.0058 (12)
S4	0.0594 (15)	0.0421 (14)	0.124 (2)	−0.0165 (12)	−0.0509 (16)	0.0069 (14)
C1	0.039 (5)	0.037 (5)	0.050 (5)	−0.003 (4)	−0.007 (4)	−0.012 (4)
C2	0.072 (5)	0.059 (5)	0.063 (5)	−0.020 (4)	−0.004 (4)	0.003 (4)
C3	0.076 (8)	0.066 (8)	0.067 (8)	−0.015 (7)	0.000 (7)	0.003 (7)
C4	0.075 (8)	0.073 (7)	0.064 (8)	−0.021 (7)	−0.002 (7)	0.000 (7)
C5	0.072 (5)	0.066 (5)	0.065 (5)	−0.021 (4)	0.005 (4)	0.003 (4)
C2'	0.072 (5)	0.059 (5)	0.063 (5)	−0.020 (4)	−0.004 (4)	0.003 (4)
C3'	0.078 (8)	0.061 (7)	0.063 (8)	−0.018 (7)	0.000 (7)	−0.004 (7)
C4'	0.080 (8)	0.068 (7)	0.069 (8)	−0.021 (7)	0.005 (7)	0.004 (7)
C5'	0.072 (5)	0.066 (5)	0.065 (5)	−0.021 (4)	0.005 (4)	0.003 (4)
C6	0.044 (5)	0.036 (5)	0.061 (6)	−0.007 (4)	−0.016 (4)	−0.005 (4)
C7	0.046 (5)	0.038 (5)	0.085 (7)	−0.009 (4)	−0.016 (5)	−0.007 (4)
C8	0.052 (6)	0.050 (6)	0.097 (8)	−0.013 (5)	−0.009 (5)	−0.023 (5)
C9	0.056 (6)	0.067 (7)	0.084 (7)	−0.024 (5)	−0.008 (5)	−0.023 (5)
C10	0.057 (6)	0.057 (6)	0.073 (7)	−0.018 (5)	−0.032 (5)	0.001 (5)
C11	0.048 (5)	0.038 (5)	0.059 (6)	−0.010 (4)	−0.007 (4)	−0.008 (4)
C12	0.056 (5)	0.033 (5)	0.055 (5)	−0.003 (4)	−0.016 (4)	−0.001 (4)
C13	0.039 (5)	0.063 (6)	0.044 (5)	−0.009 (4)	−0.005 (4)	−0.004 (4)
C14	0.035 (4)	0.050 (5)	0.042 (5)	−0.013 (4)	−0.001 (4)	−0.002 (4)
C15	0.032 (4)	0.036 (4)	0.038 (4)	−0.009 (4)	−0.002 (3)	0.000 (3)
C16	0.031 (4)	0.042 (5)	0.041 (4)	−0.013 (4)	−0.003 (3)	−0.004 (3)
C17	0.046 (5)	0.056 (6)	0.046 (5)	−0.025 (4)	0.000 (4)	−0.004 (4)
C18	0.059 (6)	0.052 (6)	0.077 (7)	−0.039 (5)	0.005 (5)	−0.009 (5)
C19	0.078 (7)	0.047 (6)	0.053 (6)	−0.036 (5)	0.003 (5)	−0.005 (4)
C20	0.052 (5)	0.042 (5)	0.056 (5)	−0.021 (4)	−0.004 (4)	−0.001 (4)
C21	0.041 (5)	0.077 (8)	0.074 (7)	−0.023 (5)	−0.008 (5)	−0.004 (5)
C22	0.052 (6)	0.083 (8)	0.067 (6)	−0.044 (6)	−0.006 (5)	−0.006 (5)

Geometric parameters (Å, º)

Bi1—S3	2.702 (3)	C3'—H3'2	0.9700
Bi1—S1	2.719 (3)	C4'—H4'1	0.9700
Bi1—S2	2.725 (3)	C4'—H4'2	0.9700
Bi1—N4	2.745 (7)	C7—C8	1.520 (12)
Bi1—N3	2.806 (7)	C7—H7A	0.9700
Bi1—S4	2.930 (4)	C7—H7B	0.9700
Bi1—I1	3.161 (2)	C8—C9	1.448 (13)
N1—C1	1.308 (11)	C8—H8A	0.9700
N1—C2	1.453 (12)	C8—H8B	0.9700
N1—C5	1.490 (12)	C9—C10	1.511 (13)
N2—C6	1.327 (10)	C9—H9A	0.9700
N2—C10	1.453 (11)	C9—H9B	0.9700
N2—C7	1.458 (11)	C10—H10A	0.9700
N3—C11	1.316 (10)	C10—H10B	0.9700
N3—C15	1.357 (9)	C11—C12	1.410 (12)
N4—C20	1.329 (10)	C11—H11	0.9300
N4—C16	1.350 (10)	C12—C13	1.368 (12)
S1—C1	1.742 (8)	C12—H12	0.9300
S2—C1	1.703 (9)	C13—C14	1.408 (12)
S3—C6	1.713 (9)	C13—H13	0.9300
S4—C6	1.693 (9)	C14—C15	1.409 (11)
C2—C3	1.524 (17)	C14—C21	1.423 (12)
C2—H2A	0.9700	C15—C16	1.432 (11)
C2—H2B	0.9700	C16—C17	1.404 (11)
C3—C4	1.52 (5)	C17—C18	1.369 (12)
C3—H3A	0.9700	C17—C22	1.441 (13)
C3—H3B	0.9700	C18—C19	1.385 (13)
C4—C5	1.52 (3)	C18—H18	0.9300
C4—H4A	0.9700	C19—C20	1.388 (12)
C4—H4B	0.9700	C19—H19	0.9300
C5—H5A	0.9700	C20—H20	0.9300
C5—H5B	0.9700	C21—C22	1.323 (13)
C3'—C4'	1.49 (4)	C21—H21	0.9300
C3'—H3'1	0.9700	C22—H22	0.9300
S3—Bi1—S1	79.80 (9)	C3'—C4'—H4'1	110.9
S3—Bi1—S2	93.44 (13)	C3'—C4'—H4'2	110.9
S1—Bi1—S2	66.30 (8)	H4'1—C4'—H4'2	108.9
S3—Bi1—N4	160.37 (15)	N2—C6—S4	120.8 (7)
S1—Bi1—N4	81.05 (16)	N2—C6—S3	119.1 (6)
S2—Bi1—N4	82.74 (17)	S4—C6—S3	120.1 (5)
S3—Bi1—N3	137.67 (15)	N2—C7—C8	103.3 (7)
S1—Bi1—N3	125.34 (15)	N2—C7—H7A	111.1
S2—Bi1—N3	72.33 (16)	C8—C7—H7A	111.1
N4—Bi1—N3	59.3 (2)	N2—C7—H7B	111.1
S3—Bi1—S4	63.05 (7)	C8—C7—H7B	111.1
S1—Bi1—S4	137.59 (9)	H7A—C7—H7B	109.1
S2—Bi1—S4	94.90 (9)	C9—C8—C7	104.2 (7)
N4—Bi1—S4	136.32 (15)	C9—C8—H8A	110.9
N3—Bi1—S4	78.32 (15)	C7—C8—H8A	110.9
S3—Bi1—I1	88.82 (11)	C9—C8—H8B	110.9
S1—Bi1—I1	82.11 (9)	C7—C8—H8B	110.9
S2—Bi1—I1	147.31 (6)	H8A—C8—H8B	108.9
N4—Bi1—I1	84.32 (16)	C8—C9—C10	105.8 (8)
N3—Bi1—I1	124.67 (15)	C8—C9—H9A	110.6
S4—Bi1—I1	114.92 (9)	C10—C9—H9A	110.6
C1—N1—C2	124.8 (7)	C8—C9—H9B	110.6
C1—N1—C5	123.2 (7)	C10—C9—H9B	110.6
C2—N1—C5	112.0 (7)	H9A—C9—H9B	108.7
C6—N2—C10	124.0 (7)	N2—C10—C9	102.1 (8)
C6—N2—C7	124.1 (7)	N2—C10—H10A	111.3
C10—N2—C7	111.9 (7)	C9—C10—H10A	111.3
C11—N3—C15	118.6 (7)	N2—C10—H10B	111.3
C11—N3—Bi1	121.3 (5)	C9—C10—H10B	111.3
C15—N3—Bi1	119.4 (5)	H10A—C10—H10B	109.2
C20—N4—C16	119.2 (7)	N3—C11—C12	123.5 (8)
C20—N4—Bi1	118.8 (5)	N3—C11—H11	118.3
C16—N4—Bi1	121.7 (5)	C12—C11—H11	118.3
C1—S1—Bi1	86.8 (3)	C13—C12—C11	119.0 (8)
C1—S2—Bi1	87.3 (3)	C13—C12—H12	120.5
C6—S3—Bi1	92.0 (3)	C11—C12—H12	120.5
C6—S4—Bi1	84.8 (3)	C12—C13—C14	118.5 (8)
N1—C1—S2	121.1 (6)	C12—C13—H13	120.8
N1—C1—S1	119.3 (6)	C14—C13—H13	120.8
S2—C1—S1	119.6 (5)	C13—C14—C15	119.0 (7)
N1—C2—C3	102.6 (13)	C13—C14—C21	121.8 (8)
N1—C2—H2A	111.2	C15—C14—C21	119.3 (8)
C3—C2—H2A	111.2	N3—C15—C14	121.5 (7)
N1—C2—H2B	111.2	N3—C15—C16	118.8 (7)
C3—C2—H2B	111.2	C14—C15—C16	119.7 (7)
H2A—C2—H2B	109.2	N4—C16—C17	121.0 (7)
C4—C3—C2	106 (2)	N4—C16—C15	119.3 (7)
C4—C3—H3A	110.5	C17—C16—C15	119.7 (7)
C2—C3—H3A	110.5	C18—C17—C16	119.2 (8)
C4—C3—H3B	110.5	C18—C17—C22	122.8 (8)
C2—C3—H3B	110.5	C16—C17—C22	118.0 (8)
H3A—C3—H3B	108.7	C17—C18—C19	119.5 (8)
C3—C4—C5	102 (2)	C17—C18—H18	120.2
C3—C4—H4A	111.5	C19—C18—H18	120.2
C5—C4—H4A	111.5	C18—C19—C20	118.5 (8)
C3—C4—H4B	111.5	C18—C19—H19	120.7
C5—C4—H4B	111.5	C20—C19—H19	120.7
H4A—C4—H4B	109.3	N4—C20—C19	122.6 (8)
N1—C5—C4	104.0 (13)	N4—C20—H20	118.7
N1—C5—H5A	111.0	C19—C20—H20	118.7
C4—C5—H5A	111.0	C22—C21—C14	120.8 (9)
N1—C5—H5B	111.0	C22—C21—H21	119.6
C4—C5—H5B	111.0	C14—C21—H21	119.6
H5A—C5—H5B	109.0	C21—C22—C17	122.5 (8)
C4'—C3'—H3'1	112.1	C21—C22—H22	118.8
C4'—C3'—H3'2	112.1	C17—C22—H22	118.8
H3'1—C3'—H3'2	109.8