metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 3| March 2011| Pages m353-m354

catena-Poly[[[(2,2′-bi­pyridine-κ2N,N′)(di­methyl sulfoxide-κO)(nitrato-κ2O,O′)bis­­muth(III)]-μ-5-carb­­oxy­benzene-1,3-di­carboxyl­ato-κ4O1,O1′:O3,O3′] di­methyl sulfoxide monosolvate]

aDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
*Correspondence e-mail: marjinamegh@yahoo.com

(Received 29 December 2010; accepted 16 February 2011; online 19 February 2011)

The polymeric title compound, {[Bi(C9H4O6)(NO3)(C10H8N2)(C2H6OS)]·C2H6OS}n, was obtained by the reaction of bis­muth(III) nitrate, bipyridine (bpy) and 1,3,5-benzene­tricarb­oxy­lic acid (H3BTC). The BiIII ion is coordinated in a distorted tricapped trigonal-prismatic geometry, defined by two N atoms of the bipy ligand, four O atoms of two HBTC2− anions, two O atoms of a nitrate anion and one O atom of a dimethyl sulfoxide ligand. The crystal packing is stabilized by O—H⋯O and C—H⋯O hydrogen bonds. The S atom of the non-coordinating dimethyl sulfoxide mol­ecule is disordered over two sets of sites with refined site-occupancies of 0.430 (19) and 0.570 (19).

Related literature

For coordination polymers derived from H3BTC, see: Skakle et al. (2001[Skakle, J. M. S., Foreman, M. R. St J., Plater, M. J. & Griffin, C. (2001). Acta Cryst. E57, m85-m87.]); Cheng et al. (2009[Cheng, L., Zhang, Y.-W., Sun, Y.-Y. & Wang, J.-Q. (2009). Acta Cryst. E65, m14.]). For related structures, see: Barbour et al. (1998[Barbour, L. J., Belfield, S. J., Junk, P. C. & Smith, M. K. (1998). Aust. J. Chem. 51, 337-342.]); Bowmaker et al. (1998[Bowmaker, G. A., Junk, P. C., Lee, A. M., Skelton, B. W. & White, A. H. (1998). Aust. J. Chem. 51, 317-324.]).

[Scheme 1]

Experimental

Crystal data
  • [Bi(C9H4O6)(NO3)(C10H8N2)(C2H6OS)]·C2H6OS

  • Mr = 791.57

  • Triclinic, [P \overline 1]

  • a = 8.9562 (18) Å

  • b = 9.882 (2) Å

  • c = 16.111 (3) Å

  • α = 89.78 (3)°

  • β = 76.22 (3)°

  • γ = 84.80 (3)°

  • V = 1378.9 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 6.61 mm−1

  • T = 298 K

  • 0.15 × 0.10 × 0.1 mm

Data collection
  • STOE IPDS II diffractometer

  • Absorption correction: numerical [shape of crystal determined optically (X-SHAPE and X-RED32; Stoe & Cie (2005[Stoe & Cie (2005). X-AREA, X-SHAPE and X-RED32. Stoe & Cie, Darmstadt, Germany.])] Tmin = 0.455, Tmax = 0.515

  • 15461 measured reflections

  • 7396 independent reflections

  • 6043 reflections with I > 2σ(I)

  • Rint = 0.124

Refinement
  • R[F2 > 2σ(F2)] = 0.072

  • wR(F2) = 0.195

  • S = 1.13

  • 7396 reflections

  • 373 parameters

  • H-atom parameters constrained

  • Δρmax = 2.25 e Å−3

  • Δρmin = −2.57 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O11i 0.82 1.79 2.60 (2) 167
C10—H10⋯O8 0.93 2.53 3.16 (2) 125
C12—H12⋯O10ii 0.93 2.58 3.51 (2) 179
C13—H13⋯O6iii 0.93 2.57 3.350 (19) 142
C17—H17⋯O2iii 0.93 2.48 3.260 (19) 142
C18—H18⋯O3iv 0.93 2.58 3.391 (17) 146
C21—H21B⋯O9v 0.96 2.56 3.49 (3) 161
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z; (iii) x+1, y-1, z; (iv) -x+1, -y, -z; (v) x, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2005[Stoe & Cie (2005). X-AREA, X-SHAPE and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

Coordination polymers are currently of great interest due to structural versatility, unique properties and their applications in different area of science. 1,3,5-benzenetricarboxylic acid (H3BTC) has three carboxylate groups and it can form coordination polymers with wide range of dimensionality from one-dimensional to three-dimensional.

The asymmetric unit of the title compound is presented in Fig. 1. In the the title compound, BiIII ion is 9-coordinated in a N2O7 environment and its geometry is distorted tricapped trigonal prismatic. In the title compound, there is one H3BTC in which two carboxylic groups are deprotonate. There are also one bipyridine, one nitrate and one dimethylsulfoxide molecule. Also there is one uncoordinated DMSO molecule in the packing of the compound. Bond lengths are within normal ranges. The crystal structure of title compound shows that the compound is extended by HBTC2- moieties and it is a one-dimensional coordination polymer. The polymeric structure of title compound is presented in Fig. 2. There are several O—H···O and C—H···O hydrogen bonds in the structure of the title compound which stabilize crystal packing (Table 1).

Related literature top

For coordination polymers containing H3BTC, see: Skakle et al. (2001); Cheng et al. (2009). For related structures, see: Barbour et al. (1998); Bowmaker et al. (1998).

Experimental top

A solution of Bi(NO3)3.5H2O (0.5 mmol, 0.2425 g) in DMSO (5 ml) was added to a mixture of bipyridine (1 mmol, 0.1569 g) and 1,3,5-benzenetricarboxylic acid (1 mmol,0.2101 g) in absolute ethanol (10 ml) and stirred for 2 hrs at room temperature. After 5 months, colorless crystals of the title compound appeared (m.p: 270°C decompose).

Refinement top

All hydrogen atoms were positioned geometrically and refined as riding atoms with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C) for aromatic C—H groups, C—H = 0.96 Å and Uiso(H) = 1.5 Ueq(C) for methyl groups and O—H = 0.82 Å with Uiso(H) = 1.5 Ueq(O). The sulfur atom of uncoordinated DMSO is disordered over two positions with refined site-occupancies of 0.430 (19) and 0.570 (19).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of title compound with displacement ellipsoids drawn at 30% probability level.
[Figure 2] Fig. 2. A view of the one-dimensional coordination polymer of the title compound. Uncoordinated DMSO molecules have been omitted for clarity.
catena-Poly[[[(2,2'-bipyridine-κ2N,N')(dimethyl sulfoxide-κO)(nitrato-κ2O,O')bismuth(III)]- µ-5-carboxybenzene-1,3-dicarboxylato-κ4O1,O1': O3,O3'] dimethyl sulfoxide monosolvate] top
Crystal data top
[Bi(C9H4O6)(NO3)(C10H8N2)(C2H6OS)]·C2H6OSZ = 2
Mr = 791.57F(000) = 772.0
Triclinic, P1Dx = 1.906 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9562 (18) ÅCell parameters from 7396 reflections
b = 9.882 (2) Åθ = 2.4–29.3°
c = 16.111 (3) ŵ = 6.61 mm1
α = 89.78 (3)°T = 298 K
β = 76.22 (3)°Plate, colorless
γ = 84.80 (3)°0.15 × 0.1 × 0.1 mm
V = 1378.9 (5) Å3
Data collection top
STOE IPDS II
diffractometer
7396 independent reflections
Radiation source: fine-focus sealed tube6043 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.124
Detector resolution: 0.15 mm pixels mm-1θmax = 29.3°, θmin = 2.4°
rotation method scansh = 1212
Absorption correction: numerical
[shape of crystal determined optically (X-SHAPE and X-RED32; Stoe & Cie (2005)]
k = 1313
Tmin = 0.455, Tmax = 0.515l = 2222
15461 measured reflections
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)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0865P)2 + 12.3704P]
where P = (Fo2 + 2Fc2)/3
7396 reflections(Δ/σ)max < 0.001
373 parametersΔρmax = 2.25 e Å3
0 restraintsΔρmin = 2.57 e Å3
Crystal data top
[Bi(C9H4O6)(NO3)(C10H8N2)(C2H6OS)]·C2H6OSγ = 84.80 (3)°
Mr = 791.57V = 1378.9 (5) Å3
Triclinic, P1Z = 2
a = 8.9562 (18) ÅMo Kα radiation
b = 9.882 (2) ŵ = 6.61 mm1
c = 16.111 (3) ÅT = 298 K
α = 89.78 (3)°0.15 × 0.1 × 0.1 mm
β = 76.22 (3)°
Data collection top
STOE IPDS II
diffractometer
7396 independent reflections
Absorption correction: numerical
[shape of crystal determined optically (X-SHAPE and X-RED32; Stoe & Cie (2005)]
6043 reflections with I > 2σ(I)
Tmin = 0.455, Tmax = 0.515Rint = 0.124
15461 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0720 restraints
wR(F2) = 0.195H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0865P)2 + 12.3704P]
where P = (Fo2 + 2Fc2)/3
7396 reflectionsΔρmax = 2.25 e Å3
373 parametersΔρmin = 2.57 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*/UeqOcc. (<1)
S2B0.8840 (10)0.4785 (8)0.2723 (6)0.061 (3)0.570 (19)
S2A0.9839 (16)0.4592 (14)0.2253 (8)0.072 (4)0.430 (19)
Bi10.45530 (5)0.03366 (4)0.26887 (3)0.02732 (13)
S10.3345 (4)0.2775 (3)0.3990 (2)0.0452 (7)
O10.2022 (16)0.4330 (11)0.0595 (8)0.065 (3)
H10.16250.44350.10030.097*
O20.1908 (14)0.6580 (10)0.0621 (6)0.054 (3)
O30.3771 (11)0.1788 (7)0.1652 (6)0.0390 (19)
O40.5178 (12)0.2701 (8)0.2386 (6)0.0407 (19)
O50.5247 (11)0.7833 (8)0.2306 (5)0.0374 (18)
O60.3481 (9)0.8965 (7)0.1763 (6)0.0351 (17)
O70.2078 (14)0.1922 (12)0.3655 (8)0.061 (3)
O80.4030 (14)0.1866 (12)0.4194 (7)0.059 (3)
O90.215 (2)0.3348 (16)0.4667 (10)0.100 (6)
O100.3402 (14)0.1262 (10)0.4050 (6)0.053 (2)
O110.898 (3)0.5681 (15)0.1982 (11)0.116 (7)
N10.7024 (12)0.0147 (9)0.3099 (6)0.0336 (19)
N20.6774 (11)0.0000 (9)0.1469 (6)0.0308 (18)
N30.2718 (18)0.2378 (12)0.4173 (8)0.054 (3)
C10.2933 (12)0.5408 (10)0.0437 (6)0.0268 (19)
C20.3340 (13)0.4186 (10)0.0780 (7)0.030 (2)
H20.31380.33820.05480.036*
C30.4043 (13)0.4129 (10)0.1462 (7)0.030 (2)
C40.4407 (14)0.5316 (10)0.1788 (7)0.032 (2)
H40.49450.52790.22170.039*
C50.3958 (14)0.6593 (10)0.1468 (6)0.030 (2)
C60.3241 (14)0.6622 (10)0.0792 (7)0.032 (2)
H60.29630.74520.05700.038*
C70.2216 (14)0.5520 (12)0.0301 (8)0.036 (2)
C80.4372 (15)0.2817 (10)0.1852 (7)0.033 (2)
C90.4271 (13)0.7856 (10)0.1874 (7)0.030 (2)
C100.7121 (18)0.0062 (15)0.3920 (8)0.047 (3)
H100.62330.01730.43460.057*
C110.852 (2)0.0318 (16)0.4135 (11)0.056 (4)
H110.85680.02440.47030.068*
C120.982 (2)0.0681 (18)0.3517 (12)0.062 (4)
H121.07790.08240.36510.074*
C130.9688 (18)0.0835 (17)0.2665 (10)0.054 (4)
H131.05470.11360.22360.065*
C140.8294 (14)0.0539 (12)0.2481 (8)0.037 (2)
C150.8066 (15)0.0620 (11)0.1590 (8)0.038 (2)
C160.9191 (15)0.1297 (15)0.0941 (9)0.045 (3)
H161.00950.17290.10430.054*
C170.8889 (18)0.1293 (15)0.0133 (9)0.048 (3)
H170.95980.17510.03170.058*
C180.7567 (19)0.0627 (13)0.0014 (8)0.046 (3)
H180.73850.05980.05590.055*
C190.6523 (14)0.0003 (13)0.0673 (8)0.037 (2)
H190.56080.04330.05880.045*
C200.512 (2)0.359 (2)0.4063 (13)0.071 (5)
H20A0.59290.32820.36150.107*
H20B0.51080.45540.40050.107*
H20C0.53150.33780.46070.107*
C210.223 (3)0.319 (2)0.5040 (13)0.091 (7)
H21A0.26910.28600.54700.137*
H21B0.22190.41630.50810.137*
H21C0.11920.27810.51230.137*
C221.032 (3)0.514 (2)0.3181 (14)0.078 (6)
H22A1.09190.44150.33870.118*0.57
H22B0.93950.53940.36110.118*0.57
H22C1.09150.59070.30530.118*0.57
H22D0.99010.60620.33140.118*0.43
H22E1.14250.50840.30900.118*0.43
H22F0.99050.45700.36470.118*0.43
C230.906 (6)0.315 (3)0.251 (2)0.17 (2)
H23A0.89520.26590.30310.254*0.57
H23B1.00720.29160.21480.254*0.57
H23C0.82940.29230.22200.254*0.57
H23D0.92600.30060.19010.254*0.43
H23E0.81400.27500.27850.254*0.43
H23F0.99180.27420.27120.254*0.43
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S2B0.053 (5)0.069 (5)0.060 (5)0.007 (3)0.018 (4)0.008 (3)
S2A0.066 (8)0.085 (8)0.061 (7)0.009 (6)0.009 (6)0.021 (6)
Bi10.0362 (2)0.01789 (17)0.0299 (2)0.00129 (12)0.01221 (14)0.00062 (12)
S10.062 (2)0.0341 (14)0.0411 (16)0.0055 (13)0.0141 (15)0.0042 (12)
O10.107 (10)0.044 (5)0.059 (6)0.011 (6)0.050 (7)0.007 (5)
O20.085 (8)0.037 (5)0.045 (5)0.012 (5)0.031 (5)0.001 (4)
O30.064 (6)0.018 (3)0.044 (5)0.012 (3)0.027 (4)0.005 (3)
O40.063 (6)0.023 (3)0.041 (4)0.002 (3)0.022 (4)0.005 (3)
O50.052 (5)0.026 (4)0.037 (4)0.008 (3)0.015 (4)0.001 (3)
O60.034 (4)0.022 (3)0.047 (5)0.004 (3)0.005 (3)0.003 (3)
O70.055 (6)0.063 (7)0.070 (7)0.005 (5)0.029 (6)0.008 (6)
O80.069 (7)0.062 (6)0.049 (6)0.021 (5)0.029 (5)0.017 (5)
O90.126 (13)0.084 (10)0.087 (10)0.046 (9)0.038 (9)0.053 (8)
O100.076 (7)0.037 (5)0.041 (5)0.005 (5)0.007 (5)0.002 (4)
O110.23 (2)0.062 (8)0.100 (11)0.031 (11)0.122 (14)0.028 (8)
N10.039 (5)0.028 (4)0.038 (5)0.006 (4)0.016 (4)0.006 (4)
N20.041 (5)0.022 (4)0.031 (4)0.000 (3)0.012 (4)0.001 (3)
N30.078 (9)0.040 (6)0.042 (6)0.004 (6)0.014 (6)0.003 (5)
C10.025 (5)0.026 (4)0.027 (5)0.006 (3)0.001 (4)0.003 (4)
C20.038 (6)0.025 (4)0.025 (5)0.004 (4)0.003 (4)0.006 (4)
C30.035 (5)0.024 (4)0.029 (5)0.003 (4)0.003 (4)0.004 (4)
C40.049 (6)0.020 (4)0.026 (5)0.003 (4)0.010 (4)0.001 (4)
C50.044 (6)0.019 (4)0.023 (4)0.004 (4)0.003 (4)0.003 (3)
C60.040 (6)0.023 (4)0.035 (5)0.004 (4)0.016 (5)0.001 (4)
C70.038 (6)0.034 (5)0.034 (5)0.006 (4)0.007 (5)0.004 (4)
C80.051 (7)0.018 (4)0.027 (5)0.004 (4)0.006 (5)0.002 (4)
C90.038 (6)0.024 (4)0.028 (5)0.011 (4)0.005 (4)0.001 (4)
C100.056 (8)0.060 (8)0.027 (6)0.001 (6)0.014 (5)0.000 (5)
C110.076 (11)0.051 (8)0.051 (8)0.003 (7)0.034 (8)0.000 (6)
C120.058 (9)0.069 (10)0.066 (10)0.012 (8)0.035 (8)0.009 (8)
C130.043 (7)0.069 (10)0.054 (8)0.000 (7)0.019 (6)0.004 (7)
C140.038 (6)0.034 (5)0.041 (6)0.002 (4)0.014 (5)0.004 (5)
C150.046 (7)0.021 (4)0.047 (7)0.002 (4)0.013 (5)0.005 (4)
C160.033 (6)0.053 (7)0.042 (7)0.006 (5)0.004 (5)0.001 (6)
C170.051 (8)0.048 (7)0.043 (7)0.004 (6)0.008 (6)0.012 (6)
C180.074 (10)0.034 (6)0.032 (6)0.016 (6)0.011 (6)0.005 (5)
C190.036 (6)0.046 (6)0.035 (6)0.010 (5)0.016 (5)0.002 (5)
C200.086 (13)0.067 (11)0.071 (11)0.004 (9)0.042 (10)0.010 (9)
C210.14 (2)0.066 (12)0.061 (11)0.025 (13)0.003 (12)0.016 (9)
C220.080 (13)0.095 (14)0.078 (13)0.028 (11)0.047 (11)0.026 (11)
C230.35 (6)0.085 (18)0.14 (3)0.06 (3)0.17 (4)0.039 (18)
Geometric parameters (Å, º) top
S2B—O111.471 (16)C4—H40.9300
S2B—C231.64 (3)C5—C61.390 (15)
S2A—O111.395 (19)C5—C91.490 (14)
S2A—C221.75 (2)C6—H60.9300
Bi1—O32.386 (8)C9—Bi1ii2.844 (10)
Bi1—O6i2.432 (9)C10—C111.38 (2)
Bi1—N22.440 (10)C10—H100.9300
Bi1—N12.463 (10)C11—C121.37 (3)
Bi1—O42.472 (8)C11—H110.9300
Bi1—O5i2.537 (8)C12—C131.42 (2)
Bi1—O72.745 (12)C12—H120.9300
Bi1—O102.750 (10)C13—C141.357 (18)
Bi1—C9i2.844 (10)C13—H130.9300
S1—O101.505 (10)C14—C151.501 (18)
S1—C201.749 (19)C15—C161.391 (18)
S1—C211.82 (2)C16—C171.39 (2)
O1—C71.311 (16)C16—H160.9300
O1—H10.8200C17—C181.37 (2)
O2—C71.204 (14)C17—H170.9300
O3—C81.268 (14)C18—C191.374 (19)
O4—C81.248 (15)C18—H180.9300
O5—C91.239 (14)C19—H190.9300
O5—Bi1ii2.537 (8)C20—H20A0.9600
O6—C91.286 (13)C20—H20B0.9600
O6—Bi1ii2.432 (9)C20—H20C0.9600
O7—N31.226 (17)C21—H21A0.9600
O8—N31.245 (17)C21—H21B0.9600
O9—N31.241 (17)C21—H21C0.9600
N1—C141.348 (16)C22—H22A0.9600
N1—C101.349 (15)C22—H22B0.9600
N2—C151.316 (15)C22—H22C0.9600
N2—C191.354 (14)C22—H22D0.9600
C1—C21.380 (14)C22—H22E0.9600
C1—C61.407 (14)C22—H22F0.9600
C1—C71.479 (16)C23—H23A0.9600
C2—C31.390 (15)C23—H23B0.9600
C2—H20.9300C23—H23C0.9600
C3—C41.384 (15)C23—H23D0.9600
C3—C81.475 (13)C23—H23E0.9600
C4—C51.422 (13)C23—H23F0.9600
O11—S2B—C23115.9 (14)O6—C9—Bi1ii58.4 (5)
O11—S2A—C22106.9 (13)C5—C9—Bi1ii174.4 (8)
O3—Bi1—O6i71.8 (3)N1—C10—C11120.9 (14)
O3—Bi1—N277.9 (3)N1—C10—H10119.5
O6i—Bi1—N280.2 (3)C11—C10—H10119.5
O3—Bi1—N1133.0 (3)C12—C11—C10120.1 (14)
O6i—Bi1—N1127.3 (3)C12—C11—H11120.0
N2—Bi1—N166.6 (3)C10—C11—H11120.0
O3—Bi1—O453.1 (3)C11—C12—C13118.3 (14)
O6i—Bi1—O4123.8 (3)C11—C12—H12120.9
N2—Bi1—O478.6 (3)C13—C12—H12120.9
N1—Bi1—O489.2 (3)C14—C13—C12119.4 (15)
O3—Bi1—O5i118.1 (3)C14—C13—H13120.3
O6i—Bi1—O5i52.6 (3)C12—C13—H13120.3
N2—Bi1—O5i68.7 (3)N1—C14—C13121.3 (12)
N1—Bi1—O5i77.1 (3)N1—C14—C15116.1 (10)
O4—Bi1—O5i147.4 (3)C13—C14—C15122.7 (12)
O3—Bi1—O777.4 (3)N2—C15—C16123.3 (12)
O6i—Bi1—O7105.3 (3)N2—C15—C14116.0 (11)
N2—Bi1—O7151.4 (3)C16—C15—C14120.6 (12)
N1—Bi1—O7123.6 (3)C15—C16—C17116.4 (13)
O4—Bi1—O775.1 (4)C15—C16—H16121.8
O5i—Bi1—O7137.0 (3)C17—C16—H16121.8
O3—Bi1—O10142.1 (3)C18—C17—C16121.4 (13)
O6i—Bi1—O1090.1 (3)C18—C17—H17119.3
N2—Bi1—O10132.8 (3)C16—C17—H17119.3
N1—Bi1—O1084.6 (3)C17—C18—C19117.5 (12)
O4—Bi1—O10139.9 (3)C17—C18—H18121.2
O5i—Bi1—O1068.9 (3)C19—C18—H18121.2
O7—Bi1—O1075.7 (3)N2—C19—C18122.5 (12)
O3—Bi1—C9i95.9 (3)N2—C19—H19118.7
O6i—Bi1—C9i26.8 (3)C18—C19—H19118.7
N2—Bi1—C9i73.5 (3)S1—C20—H20A109.5
N1—Bi1—C9i102.1 (3)S1—C20—H20B109.5
O4—Bi1—C9i142.3 (3)H20A—C20—H20B109.5
O5i—Bi1—C9i25.8 (3)S1—C20—H20C109.5
O7—Bi1—C9i123.3 (3)H20A—C20—H20C109.5
O10—Bi1—C9i77.5 (3)H20B—C20—H20C109.5
O10—S1—C20109.1 (8)S1—C21—H21A109.5
O10—S1—C21103.5 (8)S1—C21—H21B109.5
C20—S1—C2197.9 (11)H21A—C21—H21B109.5
C7—O1—H1109.5S1—C21—H21C109.5
C8—O3—Bi195.3 (7)H21A—C21—H21C109.5
C8—O4—Bi191.8 (7)H21B—C21—H21C109.5
C9—O5—Bi1ii91.1 (6)S2A—C22—H22A109.5
C9—O6—Bi1ii94.8 (7)S2A—C22—H22B109.5
N3—O7—Bi198.6 (9)H22A—C22—H22B109.5
S1—O10—Bi1124.3 (5)S2A—C22—H22C109.5
S2A—O11—S2B42.0 (6)H22A—C22—H22C109.5
C14—N1—C10120.0 (11)H22B—C22—H22C109.5
C14—N1—Bi1118.2 (8)S2A—C22—H22D109.5
C10—N1—Bi1121.7 (9)H22A—C22—H22D141.1
C15—N2—C19118.8 (11)H22B—C22—H22D56.3
C15—N2—Bi1118.5 (8)H22C—C22—H22D56.3
C19—N2—Bi1118.6 (8)S2A—C22—H22E109.5
O7—N3—O9123.7 (16)H22A—C22—H22E56.3
O7—N3—O8118.7 (12)H22B—C22—H22E141.1
O9—N3—O8117.6 (15)H22C—C22—H22E56.3
C2—C1—C6118.9 (10)H22D—C22—H22E109.5
C2—C1—C7123.6 (9)S2A—C22—H22F109.5
C6—C1—C7117.5 (9)H22A—C22—H22F56.3
C1—C2—C3121.6 (9)H22B—C22—H22F56.3
C1—C2—H2119.2H22C—C22—H22F141.1
C3—C2—H2119.2H22D—C22—H22F109.5
C4—C3—C2119.6 (9)H22E—C22—H22F109.5
C4—C3—C8119.8 (10)S2B—C23—H23A109.5
C2—C3—C8120.5 (10)S2B—C23—H23B109.5
C3—C4—C5119.9 (10)H23A—C23—H23B109.5
C3—C4—H4120.0S2B—C23—H23C109.5
C5—C4—H4120.0H23A—C23—H23C109.5
C6—C5—C4119.1 (9)H23B—C23—H23C109.5
C6—C5—C9122.3 (9)S2B—C23—H23D109.5
C4—C5—C9118.6 (10)H23A—C23—H23D141.1
C5—C6—C1120.7 (9)H23B—C23—H23D56.3
C5—C6—H6119.7H23C—C23—H23D56.3
C1—C6—H6119.7S2B—C23—H23E109.5
O2—C7—O1123.5 (12)H23A—C23—H23E56.3
O2—C7—C1123.9 (11)H23B—C23—H23E141.1
O1—C7—C1112.4 (10)H23C—C23—H23E56.3
O4—C8—O3119.5 (9)H23D—C23—H23E109.5
O4—C8—C3122.1 (10)S2B—C23—H23F109.5
O3—C8—C3118.4 (10)H23A—C23—H23F56.3
O5—C9—O6121.4 (10)H23B—C23—H23F56.3
O5—C9—C5121.2 (10)H23C—C23—H23F141.1
O6—C9—C5117.4 (10)H23D—C23—H23F109.5
O5—C9—Bi1ii63.1 (6)H23E—C23—H23F109.5
O6i—Bi1—O3—C8171.6 (8)O5i—Bi1—N2—C1990.6 (8)
N2—Bi1—O3—C888.1 (8)O7—Bi1—N2—C1967.0 (11)
N1—Bi1—O3—C847.1 (9)O10—Bi1—N2—C19118.1 (8)
O4—Bi1—O3—C83.3 (7)C9i—Bi1—N2—C1963.8 (8)
O5i—Bi1—O3—C8145.8 (7)Bi1—O7—N3—O9166.9 (16)
O7—Bi1—O3—C877.4 (8)Bi1—O7—N3—O811.3 (15)
O10—Bi1—O3—C8123.1 (7)C6—C1—C2—C30.0 (16)
C9i—Bi1—O3—C8159.7 (7)C7—C1—C2—C3178.5 (10)
O3—Bi1—O4—C83.4 (7)C1—C2—C3—C42.7 (17)
O6i—Bi1—O4—C816.8 (8)C1—C2—C3—C8175.9 (10)
N2—Bi1—O4—C886.7 (7)C2—C3—C4—C54.7 (17)
N1—Bi1—O4—C8152.9 (7)C8—C3—C4—C5174.0 (10)
O5i—Bi1—O4—C888.7 (9)C3—C4—C5—C64.0 (17)
O7—Bi1—O4—C881.9 (7)C3—C4—C5—C9175.8 (10)
O10—Bi1—O4—C8126.4 (7)C4—C5—C6—C11.3 (17)
C9i—Bi1—O4—C843.9 (10)C9—C5—C6—C1178.5 (10)
O3—Bi1—O7—N3123.6 (9)C2—C1—C6—C50.7 (17)
O6i—Bi1—O7—N3169.5 (9)C7—C1—C6—C5178.0 (10)
N2—Bi1—O7—N392.8 (11)C2—C1—C7—O2177.3 (12)
N1—Bi1—O7—N310.0 (11)C6—C1—C7—O21.2 (18)
O4—Bi1—O7—N368.8 (9)C2—C1—C7—O10.5 (17)
O5i—Bi1—O7—N3118.6 (9)C6—C1—C7—O1178.1 (11)
O10—Bi1—O7—N383.4 (9)Bi1—O4—C8—O35.8 (12)
C9i—Bi1—O7—N3147.6 (8)Bi1—O4—C8—C3171.9 (10)
C20—S1—O10—Bi184.5 (10)Bi1—O3—C8—O46.0 (12)
C21—S1—O10—Bi1172.0 (11)Bi1—O3—C8—C3171.8 (9)
O3—Bi1—O10—S196.9 (8)C4—C3—C8—O411.0 (18)
O6i—Bi1—O10—S137.1 (8)C2—C3—C8—O4170.4 (11)
N2—Bi1—O10—S139.5 (10)C4—C3—C8—O3166.8 (11)
N1—Bi1—O10—S190.4 (8)C2—C3—C8—O311.8 (17)
O4—Bi1—O10—S1172.7 (6)Bi1ii—O5—C9—O63.6 (11)
O5i—Bi1—O10—S112.1 (7)Bi1ii—O5—C9—C5176.0 (9)
O7—Bi1—O10—S1142.9 (8)Bi1ii—O6—C9—O53.8 (11)
C9i—Bi1—O10—S113.4 (7)Bi1ii—O6—C9—C5175.8 (8)
C22—S2A—O11—S2B63.8 (12)C6—C5—C9—O5160.4 (11)
C23—S2B—O11—S2A53 (2)C4—C5—C9—O519.7 (16)
O3—Bi1—N1—C1453.6 (9)C6—C5—C9—O620.0 (16)
O6i—Bi1—N1—C1446.4 (9)C4—C5—C9—O6159.9 (10)
N2—Bi1—N1—C149.3 (8)C14—N1—C10—C113 (2)
O4—Bi1—N1—C1487.2 (8)Bi1—N1—C10—C11179.1 (11)
O5i—Bi1—N1—C1462.9 (8)N1—C10—C11—C121 (2)
O7—Bi1—N1—C14158.7 (8)C10—C11—C12—C132 (3)
O10—Bi1—N1—C14132.4 (8)C11—C12—C13—C144 (3)
C9i—Bi1—N1—C1456.5 (8)C10—N1—C14—C131.0 (19)
O3—Bi1—N1—C10128.1 (10)Bi1—N1—C14—C13179.3 (11)
O6i—Bi1—N1—C10131.9 (9)C10—N1—C14—C15179.2 (11)
N2—Bi1—N1—C10172.5 (10)Bi1—N1—C14—C150.9 (13)
O4—Bi1—N1—C1094.5 (10)C12—C13—C14—N12 (2)
O5i—Bi1—N1—C10115.4 (10)C12—C13—C14—C15177.4 (14)
O7—Bi1—N1—C1023.1 (11)C19—N2—C15—C160.7 (17)
O10—Bi1—N1—C1045.8 (10)Bi1—N2—C15—C16156.1 (10)
C9i—Bi1—N1—C10121.7 (10)C19—N2—C15—C14178.1 (10)
O3—Bi1—N2—C15166.9 (9)Bi1—N2—C15—C1425.1 (13)
O6i—Bi1—N2—C15119.7 (8)N1—C14—C15—N215.8 (15)
N1—Bi1—N2—C1518.4 (8)C13—C14—C15—N2164.0 (13)
O4—Bi1—N2—C15112.6 (8)N1—C14—C15—C16165.3 (11)
O5i—Bi1—N2—C1566.2 (8)C13—C14—C15—C1614.9 (19)
O7—Bi1—N2—C15136.2 (8)N2—C15—C16—C170.1 (19)
O10—Bi1—N2—C1538.8 (10)C14—C15—C16—C17178.7 (12)
C9i—Bi1—N2—C1593.1 (8)C15—C16—C17—C181 (2)
O3—Bi1—N2—C1936.2 (8)C16—C17—C18—C192 (2)
O6i—Bi1—N2—C1937.1 (8)C15—N2—C19—C180.1 (17)
N1—Bi1—N2—C19175.3 (9)Bi1—N2—C19—C18157.0 (9)
O4—Bi1—N2—C1990.5 (8)C17—C18—C19—N21.6 (19)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O11iii0.821.792.60 (2)167
C10—H10···O80.932.533.16 (2)125
C12—H12···O10iv0.932.583.51 (2)179
C13—H13···O6v0.932.573.350 (19)142
C17—H17···O2v0.932.483.260 (19)142
C18—H18···O3vi0.932.583.391 (17)146
C21—H21B···O9i0.962.563.49 (3)161
Symmetry codes: (i) x, y1, z; (iii) x+1, y+1, z; (iv) x+1, y, z; (v) x+1, y1, z; (vi) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Bi(C9H4O6)(NO3)(C10H8N2)(C2H6OS)]·C2H6OS
Mr791.57
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)8.9562 (18), 9.882 (2), 16.111 (3)
α, β, γ (°)89.78 (3), 76.22 (3), 84.80 (3)
V3)1378.9 (5)
Z2
Radiation typeMo Kα
µ (mm1)6.61
Crystal size (mm)0.15 × 0.1 × 0.1
Data collection
DiffractometerSTOE IPDS II
diffractometer
Absorption correctionNumerical
[shape of crystal determined optically (X-SHAPE and X-RED32; Stoe & Cie (2005)]
Tmin, Tmax0.455, 0.515
No. of measured, independent and
observed [I > 2σ(I)] reflections
15461, 7396, 6043
Rint0.124
(sin θ/λ)max1)0.687
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.072, 0.195, 1.13
No. of reflections7396
No. of parameters373
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0865P)2 + 12.3704P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)2.25, 2.57

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O11i0.821.792.60 (2)167
C10—H10···O80.932.533.16 (2)125
C12—H12···O10ii0.932.583.51 (2)179
C13—H13···O6iii0.932.573.350 (19)142
C17—H17···O2iii0.932.483.260 (19)142
C18—H18···O3iv0.932.583.391 (17)146
C21—H21B···O9v0.962.563.49 (3)161
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x+1, y1, z; (iv) x+1, y, z; (v) x, y1, z.
 

Acknowledgements

The authors grateful acknowledge the Islamic Azad University, North Tehran Branch, for financial support.

References

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First citationStoe & Cie (2005). X-AREA, X-SHAPE and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar

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Volume 67| Part 3| March 2011| Pages m353-m354
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