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The title compound, [Bi(C5H10NS2)2I(C12H8N2)], is monomeric, with the Bi atom chelated by the S atoms of two N,N-diethyl­dithio­carbamate ligands and the N atoms of 1,10-phenanthroline. An iodo ligand completes the coordination, with the seven-coordinate Bi atom adopting a highly distorted capped octa­hedral geometry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805035580/sj6144sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805035580/sj6144Isup2.hkl
Contains datablock I

CCDC reference: 293985

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.020 Å
  • R factor = 0.058
  • wR factor = 0.140
  • Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.110 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S4 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.12 PLAT335_ALERT_2_C Large Benzene C-C Range C14 -C21 0.16 Ang. PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 20
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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.

Bis(N,N-diethyldithiocarbamato-κ2S,S')iodo(1,10-phenanthroline)bismuth(III) top
Crystal data top
[Bi(C5H10NS2)2I(C12H8N2)]F(000) = 1552
Mr = 812.60Dx = 1.961 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2669 reflections
a = 13.174 (6) Åθ = 2.5–22.5°
b = 10.506 (5) ŵ = 7.85 mm1
c = 20.259 (8) ÅT = 298 K
β = 100.993 (7)°Block, orange
V = 2753 (2) Å30.41 × 0.38 × 0.34 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
4740 independent reflections
Radiation source: fine-focus sealed tube2671 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.110
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1515
Tmin = 0.056, Tmax = 0.069k = 1212
13358 measured reflectionsl = 2418
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0498P)2]
where P = (Fo2 + 2Fc2)/3
4740 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 2.28 e Å3
258 restraintsΔρmin = 1.44 e Å3
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
xyzUiso*/Ueq
Bi10.22758 (4)0.74212 (5)0.08389 (3)0.03567 (18)
I10.12379 (8)0.88655 (10)0.19236 (5)0.0576 (3)
N10.5350 (10)0.5701 (11)0.1719 (6)0.049 (3)
N20.3316 (8)1.0649 (10)0.0339 (6)0.041 (3)
N30.1480 (8)0.5190 (10)0.1234 (6)0.047 (3)
N40.1460 (7)0.5479 (10)0.0119 (6)0.035 (3)
S10.3933 (3)0.6115 (3)0.06030 (18)0.0449 (9)
S20.3731 (3)0.6979 (4)0.1953 (2)0.0491 (10)
S30.3387 (3)0.9551 (3)0.08097 (18)0.0416 (9)
S40.1988 (3)0.8754 (4)0.0424 (2)0.0600 (11)
C10.4463 (10)0.6218 (14)0.1458 (7)0.045 (3)
C20.5775 (11)0.5743 (16)0.2412 (8)0.058 (3)
H2A0.61760.49760.25350.070*
H2B0.52170.57550.26620.070*
C30.6447 (14)0.6864 (18)0.2607 (9)0.088 (5)
H3A0.70370.68180.23940.132*
H3B0.66740.68730.30870.132*
H3C0.60660.76280.24680.132*
C40.6014 (12)0.5064 (14)0.1285 (8)0.055 (3)
H4A0.57200.52280.08160.066*
H4B0.66990.54400.13790.066*
C50.6106 (14)0.3712 (16)0.1388 (9)0.080 (5)
H5A0.64110.35420.18480.120*
H5B0.65360.33620.11000.120*
H5C0.54330.33290.12830.120*
C60.2912 (11)0.9725 (12)0.0041 (7)0.043 (3)
C70.4090 (11)1.1515 (13)0.0040 (8)0.052 (3)
H7A0.45191.17320.03630.063*
H7B0.45281.11050.03400.063*
C80.3659 (13)1.2701 (13)0.0193 (9)0.066 (4)
H8A0.32291.31140.01810.099*
H8B0.42141.32580.03860.099*
H8C0.32551.24960.05260.099*
C90.2951 (11)1.0856 (14)0.1074 (7)0.053 (3)
H9A0.30021.17550.11730.064*
H9B0.22281.06150.11940.064*
C100.3563 (14)1.0105 (16)0.1495 (8)0.077 (5)
H10A0.42861.01590.13000.116*
H10B0.34461.04460.19430.116*
H10C0.33480.92310.15100.116*
C110.1450 (10)0.5072 (14)0.1873 (8)0.050 (3)
H110.16340.57750.21490.060*
C120.1170 (11)0.3998 (15)0.2161 (8)0.056 (3)
H120.11590.39680.26180.067*
C130.0901 (10)0.2940 (14)0.1752 (8)0.053 (2)
H130.06900.21920.19310.063*
C140.0949 (11)0.3015 (14)0.1071 (8)0.051 (2)
C150.1221 (10)0.4199 (14)0.0814 (8)0.047 (2)
C160.1220 (10)0.4357 (14)0.0125 (8)0.046 (2)
C170.0925 (10)0.3315 (14)0.0324 (8)0.047 (2)
C180.0930 (10)0.3494 (15)0.0985 (8)0.053 (2)
H180.07610.28130.12790.063*
C190.1172 (10)0.4628 (14)0.1235 (8)0.052 (3)
H190.11490.47640.16910.062*
C200.1457 (10)0.5576 (14)0.0751 (8)0.048 (3)
H200.16650.63530.09010.057*
C210.0678 (10)0.1981 (14)0.0590 (8)0.053 (2)
H210.04870.12000.07440.064*
C220.0692 (10)0.2106 (14)0.0044 (8)0.051 (2)
H220.05510.14030.03250.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Bi10.0341 (3)0.0277 (3)0.0462 (3)0.0009 (3)0.0104 (2)0.0003 (3)
I10.0541 (7)0.0555 (7)0.0677 (8)0.0020 (6)0.0229 (5)0.0177 (6)
N10.056 (8)0.042 (8)0.052 (9)0.017 (7)0.015 (7)0.018 (6)
N20.043 (7)0.023 (6)0.054 (8)0.002 (6)0.004 (6)0.004 (5)
N30.041 (7)0.034 (7)0.075 (10)0.010 (6)0.033 (7)0.007 (6)
N40.017 (6)0.032 (6)0.055 (8)0.006 (5)0.007 (5)0.000 (6)
S10.047 (2)0.038 (2)0.051 (3)0.0080 (19)0.0133 (18)0.0027 (18)
S20.042 (2)0.048 (2)0.056 (3)0.0048 (19)0.0077 (19)0.0043 (19)
S30.047 (2)0.035 (2)0.042 (2)0.0135 (18)0.0071 (18)0.0024 (17)
S40.070 (3)0.042 (2)0.059 (3)0.019 (2)0.011 (2)0.008 (2)
C10.032 (6)0.054 (7)0.048 (7)0.003 (6)0.007 (5)0.001 (6)
C20.040 (6)0.063 (7)0.069 (8)0.001 (6)0.003 (6)0.003 (6)
C30.071 (11)0.083 (12)0.098 (12)0.021 (10)0.014 (9)0.008 (10)
C40.038 (6)0.064 (7)0.064 (7)0.001 (6)0.010 (5)0.001 (6)
C50.079 (11)0.065 (11)0.094 (12)0.029 (10)0.011 (9)0.004 (10)
C60.049 (7)0.021 (6)0.064 (7)0.010 (5)0.020 (6)0.010 (5)
C70.054 (7)0.032 (6)0.071 (7)0.009 (6)0.011 (6)0.008 (6)
C80.070 (10)0.033 (9)0.093 (11)0.003 (8)0.009 (9)0.018 (8)
C90.058 (7)0.033 (6)0.069 (7)0.007 (6)0.012 (6)0.008 (6)
C100.087 (11)0.066 (11)0.077 (11)0.027 (10)0.013 (9)0.003 (9)
C110.037 (5)0.050 (5)0.063 (6)0.004 (5)0.008 (5)0.011 (5)
C120.042 (5)0.054 (5)0.070 (6)0.002 (5)0.004 (5)0.014 (5)
C130.038 (5)0.049 (5)0.070 (5)0.005 (4)0.009 (4)0.021 (5)
C140.036 (4)0.047 (4)0.067 (5)0.005 (4)0.006 (4)0.012 (4)
C150.031 (4)0.042 (4)0.068 (5)0.004 (4)0.008 (4)0.009 (4)
C160.028 (4)0.044 (4)0.066 (5)0.003 (4)0.006 (4)0.004 (4)
C170.030 (4)0.044 (4)0.067 (5)0.003 (4)0.010 (4)0.005 (4)
C180.035 (4)0.050 (5)0.072 (5)0.001 (4)0.006 (4)0.003 (5)
C190.035 (5)0.053 (5)0.067 (6)0.001 (5)0.007 (5)0.001 (5)
C200.033 (5)0.044 (5)0.067 (6)0.003 (5)0.011 (5)0.002 (5)
C210.038 (4)0.045 (5)0.073 (5)0.007 (4)0.004 (4)0.012 (5)
C220.036 (4)0.043 (4)0.073 (5)0.005 (4)0.004 (4)0.005 (4)
Geometric parameters (Å, º) top
Bi1—S32.681 (3)C7—C81.483 (18)
Bi1—S12.697 (4)C7—H7A0.9700
Bi1—S22.708 (4)C7—H7B0.9700
Bi1—N32.748 (11)C8—H8A0.9600
Bi1—S42.878 (4)C8—H8B0.9600
Bi1—N42.879 (11)C8—H8C0.9600
Bi1—I13.1856 (13)C9—C101.504 (19)
N1—C11.304 (16)C9—H9A0.9700
N1—C21.410 (18)C9—H9B0.9700
N1—C41.510 (17)C10—H10A0.9600
N2—C61.309 (15)C10—H10B0.9600
N2—C71.415 (16)C10—H10C0.9600
N2—C91.490 (17)C11—C121.352 (19)
N3—C111.308 (16)C11—H110.9300
N3—C151.348 (17)C12—C131.39 (2)
N4—C201.283 (16)C12—H120.9300
N4—C161.339 (16)C13—C141.395 (19)
S1—C11.743 (14)C13—H130.9300
S2—C11.717 (13)C14—C151.421 (19)
S3—C61.727 (15)C14—C211.46 (2)
S4—C61.663 (15)C15—C161.404 (18)
C2—C31.48 (2)C16—C171.429 (19)
C2—H2A0.9700C17—C181.353 (18)
C2—H2B0.9700C17—C221.448 (19)
C3—H3A0.9600C18—C191.356 (19)
C3—H3B0.9600C18—H180.9300
C3—H3C0.9600C19—C201.398 (19)
C4—C51.44 (2)C19—H190.9300
C4—H4A0.9700C20—H200.9300
C4—H4B0.9700C21—C221.294 (18)
C5—H5A0.9600C21—H210.9300
C5—H5B0.9600C22—H220.9300
C5—H5C0.9600
S3—Bi1—S187.52 (11)N2—C6—S4124.4 (12)
S3—Bi1—S281.89 (12)N2—C6—S3115.9 (12)
S1—Bi1—S265.94 (11)S4—C6—S3119.6 (8)
S3—Bi1—N3163.4 (3)N2—C7—C8112.8 (12)
S1—Bi1—N389.1 (2)N2—C7—H7A109.0
S2—Bi1—N381.9 (3)C8—C7—H7A109.0
S3—Bi1—S463.51 (11)N2—C7—H7B109.0
S1—Bi1—S493.66 (12)C8—C7—H7B109.0
S2—Bi1—S4140.97 (12)H7A—C7—H7B107.8
N3—Bi1—S4133.0 (3)C7—C8—H8A109.5
S3—Bi1—N4135.4 (2)C7—C8—H8B109.5
S1—Bi1—N474.4 (2)H8A—C8—H8B109.5
S2—Bi1—N4123.6 (2)C7—C8—H8C109.5
N3—Bi1—N458.5 (3)H8A—C8—H8C109.5
S4—Bi1—N477.1 (2)H8B—C8—H8C109.5
S3—Bi1—I185.74 (8)N2—C9—C10112.6 (12)
S1—Bi1—I1146.40 (8)N2—C9—H9A109.1
S2—Bi1—I180.52 (8)C10—C9—H9A109.1
N3—Bi1—I188.1 (2)N2—C9—H9B109.1
S4—Bi1—I1112.36 (10)C10—C9—H9B109.1
N4—Bi1—I1130.43 (19)H9A—C9—H9B107.8
C1—N1—C2123.1 (12)C9—C10—H10A109.5
C1—N1—C4121.4 (12)C9—C10—H10B109.5
C2—N1—C4115.4 (12)H10A—C10—H10B109.5
C6—N2—C7127.0 (13)C9—C10—H10C109.5
C6—N2—C9119.2 (12)H10A—C10—H10C109.5
C7—N2—C9113.8 (11)H10B—C10—H10C109.5
C11—N3—C15120.0 (13)N3—C11—C12124.6 (16)
C11—N3—Bi1117.1 (9)N3—C11—H11117.7
C15—N3—Bi1122.6 (9)C12—C11—H11117.7
C20—N4—C16118.9 (13)C11—C12—C13118.1 (15)
C20—N4—Bi1123.1 (9)C11—C12—H12121.0
C16—N4—Bi1117.3 (9)C13—C12—H12121.0
C1—S1—Bi188.7 (5)C14—C13—C12119.2 (14)
C1—S2—Bi188.9 (5)C14—C13—H13120.4
C6—S3—Bi190.9 (5)C12—C13—H13120.4
C6—S4—Bi185.6 (5)C13—C14—C15118.3 (15)
N1—C1—S2121.1 (11)C13—C14—C21124.6 (14)
N1—C1—S1122.4 (10)C15—C14—C21117.0 (14)
S2—C1—S1116.5 (8)N3—C15—C16119.3 (13)
N1—C2—C3113.3 (14)N3—C15—C14119.7 (14)
N1—C2—H2A108.9C16—C15—C14121.0 (15)
C3—C2—H2A108.9N4—C16—C15121.0 (14)
N1—C2—H2B108.9N4—C16—C17119.6 (14)
C3—C2—H2B108.9C15—C16—C17119.4 (13)
H2A—C2—H2B107.7C18—C17—C16118.1 (14)
C2—C3—H3A109.5C18—C17—C22123.4 (15)
C2—C3—H3B109.5C16—C17—C22118.3 (14)
H3A—C3—H3B109.5C17—C18—C19122.5 (15)
C2—C3—H3C109.5C17—C18—H18118.8
H3A—C3—H3C109.5C19—C18—H18118.8
H3B—C3—H3C109.5C18—C19—C20114.5 (15)
C5—C4—N1113.3 (12)C18—C19—H19122.7
C5—C4—H4A108.9C20—C19—H19122.7
N1—C4—H4A108.9N4—C20—C19126.3 (14)
C5—C4—H4B108.9N4—C20—H20116.9
N1—C4—H4B108.9C19—C20—H20116.9
H4A—C4—H4B107.7C22—C21—C14122.6 (14)
C4—C5—H5A109.5C22—C21—H21118.7
C4—C5—H5B109.5C14—C21—H21118.7
H5A—C5—H5B109.5C21—C22—C17121.5 (15)
C4—C5—H5C109.5C21—C22—H22119.2
H5A—C5—H5C109.5C17—C22—H22119.2
H5B—C5—H5C109.5
 

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