Literature DB >> 22065819

2-(2-Pyrid-yl)pyridinium (2,2'-bipyridine-κN,N')tetra-kis-(nitrato-κO,O')bis-muthate(III).

Zhao-Hui Meng1, Shu-Shen Zhang.   

Abstract

The structure of the title compound, (C(10)H(9)N(2))[Bi(NO(3))(4)(C(10)H(8)N(2))], consists of 2-(2-pyrid-yl)pyridinium cations and anions [Bi(NO(3))(4)(C(10)H(8)N(2))](-). The Bi(3+) ion lies on the twofold axis. It is coordinated by two nitro-gen atoms from one 2,2'-bipyridine ligand and eight oxygen atoms from four NO(3) (-) anions. The disordered cation is positioned at the inversion centre. The [Bi(NO(3))(4)(C(10)H(8)N(2))](-) anions and 2-(2-pyrid-yl)pyridinium cations are connected via N-H⋯O hydrogen bonds into chains. Moreover, these chains are further linked into a two-dimensional layered structure through π-π stacking inter-actions between bipyridine ligands along the c axis [centroid-centroid distance = 2.868 (4) Å].

Entities:  

Year:  2011        PMID： 22065819      PMCID： PMC3201447          DOI： 10.1107/S160053681103769X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For potential applications of bis­muth(III) coordination compounds in medical chemistry, see: Sun & Szeto (2003 ▶); Sun et al. (2004 ▶). For reported bis­muth(III) coordination compounds, see: Andrews et al. (2006 ▶); Boitrel et al. (2003 ▶); Marsh (2002 ▶); Wullens et al. (1998 ▶); Yang et al. (2006 ▶, 2007 ▶). For the structure of disordered protonated 2,2′-bipyridine, see: Bowmaker et al. (1998 ▶). For the bond-strength calculations, see: Brown & Altermatt (1985 ▶); Brese & O’Keeffe (1991 ▶).

Experimental

Crystal data

(C10H9N2)[Bi(NO3)4(C10H8N2)] M = 770.40 Monoclinic, a = 14.711 (5) Å b = 10.169 (3) Å c = 16.832 (5) Å β = 97.275 (6)° V = 2497.7 (13) Å3 Z = 4 Mo Kα radiation μ = 7.14 mm−1 T = 293 K 0.26 × 0.24 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.258, T max = 0.360 5998 measured reflections 2224 independent reflections 1895 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.084 S = 1.02 2224 reflections 194 parameters 11 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 1.13 e Å−3 Δρmin = −1.43 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Bruker, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) global. DOI: 10.1107/S160053681103769X/yk2019sup1.cif Additional supplementary materials: crystallographic information; 3D view; checkCIF report
(C10H9N2)[Bi(NO3)4(C10H8N2)]F(000) = 1488
Mr = 770.40Dx = 2.049 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2470 reflections
a = 14.711 (5) Åθ = 2.4–22.5°
b = 10.169 (3) ŵ = 7.14 mm−1
c = 16.832 (5) ÅT = 293 K
β = 97.275 (6)°Block, colorless
V = 2497.7 (13) Å30.26 × 0.24 × 0.18 mm
Z = 4
Bruker APEXII CCD diffractometer2224 independent reflections
Radiation source: fine-focus sealed tube1895 reflections with I > 2σ(I)
graphiteRint = 0.036
φ and ω scansθmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −13→17
Tmin = 0.258, Tmax = 0.360k = −12→12
5998 measured reflectionsl = −20→17
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0459P)2 + 9.2649P] where P = (Fo2 + 2Fc2)/3
2224 reflections(Δ/σ)max < 0.001
194 parametersΔρmax = 1.13 e Å−3
11 restraintsΔρmin = −1.43 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
xyzUiso*/UeqOcc. (<1)
Bi10.00000.43500 (3)0.25000.03845 (15)
C1−0.1200 (5)0.6312 (8)0.3579 (4)0.0481 (18)
H1−0.13380.55040.37940.058*
C2−0.1652 (5)0.7417 (7)0.3805 (4)0.0487 (18)
H2−0.20720.73580.41730.058*
C3−0.1466 (5)0.8595 (7)0.3475 (4)0.0508 (19)
H3−0.17850.93480.35890.061*
C4−0.0802 (5)0.8654 (7)0.2972 (4)0.0437 (17)
H4−0.06500.94620.27670.052*
C5−0.0351 (4)0.7518 (6)0.2764 (4)0.0335 (14)
C60.0361 (5)0.0371 (7)−0.0162 (4)0.0473 (18)
C70.0484 (6)0.1654 (8)0.0057 (4)0.063 (2)0.50
H4A0.01310.20450.04130.075*0.25
H70.01320.20450.04130.075*0.50
C80.1149 (10)0.2352 (12)−0.0267 (8)0.094 (4)
H80.100 (6)0.315 (5)−0.006 (5)0.07 (3)*
C90.1650 (8)0.179 (2)−0.0789 (8)0.111 (5)
H90.20860.2271−0.10170.134*
C100.1511 (9)0.0488 (18)−0.0982 (7)0.098 (4)
H100.162 (10)0.000 (13)−0.143 (6)0.15 (6)*
C110.0859 (6)−0.0230 (9)−0.0674 (5)0.067 (2)0.50
H50.0760−0.1109−0.08130.080*0.25
H110.0760−0.1109−0.08130.080*0.50
O1−0.1017 (5)0.2143 (8)0.2235 (4)0.095 (2)
O2−0.1374 (4)0.3450 (6)0.3126 (4)0.0784 (19)
O3−0.2044 (5)0.1589 (7)0.2956 (5)0.101 (2)
O4−0.0397 (5)0.3946 (7)0.0954 (4)0.0789 (18)
O5−0.1352 (4)0.5005 (6)0.1561 (3)0.0635 (15)
O6−0.1767 (5)0.4407 (7)0.0349 (4)0.094 (2)
N1−0.1488 (5)0.2376 (7)0.2795 (5)0.0631 (19)
N2−0.1182 (5)0.4426 (7)0.0941 (4)0.0593 (18)
N3−0.0577 (4)0.6348 (5)0.3070 (3)0.0365 (12)
N40.0484 (6)0.1654 (8)0.0057 (4)0.063 (2)0.50
N50.0859 (6)−0.0230 (9)−0.0674 (5)0.067 (2)0.50
U11U22U33U12U13U23
Bi10.0478 (2)0.0270 (2)0.0448 (2)0.0000.02219 (16)0.000
C10.055 (5)0.047 (4)0.047 (4)−0.004 (4)0.023 (4)0.000 (4)
C20.052 (4)0.052 (5)0.046 (4)0.010 (3)0.022 (3)−0.005 (4)
C30.061 (5)0.042 (4)0.053 (5)0.017 (4)0.017 (4)−0.006 (4)
C40.063 (5)0.026 (4)0.040 (4)0.009 (3)0.002 (3)0.002 (3)
C50.041 (4)0.029 (3)0.032 (3)0.002 (3)0.012 (3)−0.005 (3)
C60.047 (4)0.053 (5)0.040 (4)0.011 (3)0.000 (3)−0.002 (3)
C70.076 (5)0.053 (5)0.059 (5)0.000 (4)0.006 (4)−0.004 (4)
C80.116 (10)0.066 (8)0.093 (8)−0.020 (7)−0.018 (8)0.003 (7)
C90.062 (7)0.181 (15)0.089 (9)−0.025 (9)−0.001 (6)0.065 (10)
C100.070 (7)0.164 (14)0.062 (7)0.047 (9)0.012 (6)0.023 (9)
C110.069 (5)0.080 (6)0.052 (4)0.026 (4)0.011 (4)−0.002 (4)
O10.096 (2)0.094 (2)0.097 (2)−0.0016 (10)0.0153 (10)−0.0016 (10)
O20.092 (5)0.055 (4)0.097 (5)−0.028 (3)0.048 (4)−0.016 (3)
O30.093 (5)0.064 (4)0.152 (7)−0.031 (4)0.039 (5)0.020 (4)
O40.085 (5)0.087 (5)0.071 (4)−0.001 (4)0.034 (4)−0.023 (3)
O50.064 (4)0.073 (4)0.054 (3)0.006 (3)0.008 (3)−0.015 (3)
O60.103 (5)0.121 (6)0.053 (4)−0.031 (4)−0.009 (4)−0.013 (4)
N10.062 (4)0.046 (4)0.087 (5)−0.007 (3)0.031 (4)0.017 (4)
N20.071 (5)0.058 (4)0.053 (4)−0.013 (4)0.021 (4)−0.010 (4)
N30.046 (3)0.027 (3)0.039 (3)0.004 (2)0.013 (3)0.001 (2)
N40.076 (5)0.053 (5)0.059 (5)0.000 (4)0.006 (4)−0.004 (4)
N50.069 (5)0.080 (6)0.052 (4)0.026 (4)0.011 (4)−0.002 (4)
Bi1—N32.444 (5)C6—C111.346 (10)
Bi1—N3i2.444 (5)C6—C71.362 (10)
Bi1—O5i2.470 (6)C6—C6ii1.463 (15)
Bi1—O52.470 (6)C7—C81.376 (15)
Bi1—O22.564 (6)C7—H4A0.9300
Bi1—O2i2.564 (6)C7—H70.9300
Bi1—O42.626 (6)C8—C91.345 (19)
Bi1—O4i2.626 (6)C8—H80.92 (2)
Bi1—O12.703 (8)C9—C101.368 (19)
Bi1—O1i2.703 (8)C9—H90.9300
C1—N31.333 (8)C10—C111.359 (17)
C1—C21.383 (10)C10—H100.93 (2)
C1—H10.9300C11—H50.9300
C2—C31.363 (10)C11—H110.9299
C2—H20.9300O1—N11.261 (9)
C3—C41.372 (10)O2—N11.228 (8)
C3—H30.9300O3—N11.200 (8)
C4—C51.399 (9)O4—N21.252 (9)
C4—H40.9300O5—N21.250 (8)
C5—N31.353 (8)O6—N21.232 (10)
C5—C5i1.445 (12)
N3—Bi1—N3i67.5 (2)C3—C2—H2120.8
N3—Bi1—O5i79.4 (2)C1—C2—H2120.8
N3i—Bi1—O5i74.64 (18)C2—C3—C4119.0 (6)
N3—Bi1—O574.64 (18)C2—C3—H3120.5
N3i—Bi1—O579.4 (2)C4—C3—H3120.5
O5i—Bi1—O5148.7 (3)C3—C4—C5121.1 (7)
N3—Bi1—O278.73 (19)C3—C4—H4119.5
N3i—Bi1—O2142.1 (2)C5—C4—H4119.5
O5i—Bi1—O2116.5 (2)N3—C5—C4118.9 (6)
O5—Bi1—O275.3 (2)N3—C5—C5i117.6 (3)
N3—Bi1—O2i142.1 (2)C4—C5—C5i123.5 (4)
N3i—Bi1—O2i78.73 (19)C11—C6—C7122.9 (8)
O5i—Bi1—O2i75.3 (2)C11—C6—C6ii119.0 (9)
O5—Bi1—O2i116.5 (2)C7—C6—C6ii118.1 (8)
O2—Bi1—O2i138.2 (3)C6—C7—C8117.7 (9)
N3—Bi1—O4118.3 (2)C6—C7—H4A121.2
N3i—Bi1—O477.65 (19)C8—C7—H4A121.2
O5i—Bi1—O4137.4 (2)C6—C7—H7121.2
O5—Bi1—O449.3 (2)C8—C7—H7121.2
O2—Bi1—O4105.3 (2)H4A—C7—H70.0
O2i—Bi1—O468.0 (2)C9—C8—C7120.8 (11)
N3—Bi1—O4i77.65 (19)C9—C8—H8143 (6)
N3i—Bi1—O4i118.3 (2)C7—C8—H895 (6)
O5i—Bi1—O4i49.3 (2)C8—C9—C10119.4 (11)
O5—Bi1—O4i137.4 (2)C8—C9—H9120.3
O2—Bi1—O4i68.0 (2)C10—C9—H9120.3
O2i—Bi1—O4i105.3 (2)C11—C10—C9121.3 (11)
O4—Bi1—O4i162.0 (3)C11—C10—H10103 (10)
N3—Bi1—O1122.9 (2)C9—C10—H10132 (10)
N3i—Bi1—O1147.0 (2)C6—C11—C10117.8 (10)
O5i—Bi1—O1135.5 (2)C6—C11—H5121.1
O5—Bi1—O174.6 (2)C10—C11—H5121.1
O2—Bi1—O147.4 (2)C6—C11—H11121.1
O2i—Bi1—O194.8 (2)C10—C11—H11121.1
O4—Bi1—O170.0 (2)H5—C11—H110.1
O4i—Bi1—O194.7 (2)N1—O1—Bi193.8 (5)
N3—Bi1—O1i147.0 (2)N1—O2—Bi1101.6 (5)
N3i—Bi1—O1i122.9 (2)N2—O4—Bi192.6 (4)
O5i—Bi1—O1i74.6 (2)N2—O5—Bi1100.2 (5)
O5—Bi1—O1i135.5 (2)O3—N1—O2123.3 (8)
O2—Bi1—O1i94.8 (2)O3—N1—O1119.9 (8)
O2i—Bi1—O1i47.4 (2)O2—N1—O1116.7 (7)
O4—Bi1—O1i94.7 (2)O6—N2—O5119.3 (8)
O4i—Bi1—O1i70.0 (2)O6—N2—O4123.8 (7)
O1—Bi1—O1i67.7 (3)O5—N2—O4116.8 (7)
N3—C1—C2123.2 (7)C1—N3—C5119.4 (6)
N3—C1—H1118.4C1—N3—Bi1122.0 (5)
C2—C1—H1118.4C5—N3—Bi1117.8 (4)
C3—C2—C1118.3 (6)
N3—C1—C2—C31.6 (12)N3i—Bi1—O5—N288.9 (5)
C1—C2—C3—C4−3.9 (11)O5i—Bi1—O5—N2123.2 (5)
C2—C3—C4—C53.3 (11)O2—Bi1—O5—N2−119.6 (5)
C3—C4—C5—N3−0.2 (10)O2i—Bi1—O5—N217.3 (5)
C3—C4—C5—C5i179.7 (8)O4—Bi1—O5—N26.1 (4)
C11—C6—C7—C80.1 (12)O4i—Bi1—O5—N2−150.5 (4)
C6ii—C6—C7—C8−178.4 (9)O1—Bi1—O5—N2−70.5 (5)
C6—C7—C8—C90.8 (15)O1i—Bi1—O5—N2−37.8 (6)
C7—C8—C9—C10−1.8 (18)Bi1—O2—N1—O3175.6 (7)
C8—C9—C10—C112.0 (17)Bi1—O2—N1—O1−7.8 (8)
C7—C6—C11—C100.0 (12)Bi1—O1—N1—O3−176.0 (7)
C6ii—C6—C11—C10178.5 (9)Bi1—O1—N1—O27.3 (8)
C9—C10—C11—C6−1.0 (15)Bi1—O5—N2—O6172.3 (6)
N3—Bi1—O1—N1−28.6 (6)Bi1—O5—N2—O4−11.0 (8)
N3i—Bi1—O1—N1−127.7 (5)Bi1—O4—N2—O6−173.2 (7)
O5i—Bi1—O1—N181.7 (6)Bi1—O4—N2—O510.2 (7)
O5—Bi1—O1—N1−88.2 (5)C2—C1—N3—C51.5 (11)
O2—Bi1—O1—N1−4.2 (5)C2—C1—N3—Bi1−168.7 (6)
O2i—Bi1—O1—N1155.6 (5)C4—C5—N3—C1−2.2 (10)
O4—Bi1—O1—N1−140.0 (5)C5i—C5—N3—C1177.9 (7)
O4i—Bi1—O1—N149.8 (5)C4—C5—N3—Bi1168.4 (5)
O1i—Bi1—O1—N1115.9 (6)C5i—C5—N3—Bi1−11.5 (9)
N3—Bi1—O2—N1163.7 (6)N3i—Bi1—N3—C1174.4 (7)
N3i—Bi1—O2—N1136.6 (5)O5i—Bi1—N3—C1−107.9 (5)
O5i—Bi1—O2—N1−124.2 (5)O5—Bi1—N3—C189.8 (6)
O5—Bi1—O2—N186.8 (5)O2—Bi1—N3—C112.1 (5)
O2i—Bi1—O2—N1−26.7 (5)O2i—Bi1—N3—C1−156.7 (5)
O4—Bi1—O2—N147.2 (6)O4—Bi1—N3—C1113.5 (5)
O4i—Bi1—O2—N1−115.2 (6)O4i—Bi1—N3—C1−57.6 (5)
O1—Bi1—O2—N14.4 (5)O1—Bi1—N3—C130.1 (6)
O1i—Bi1—O2—N1−49.0 (6)O1i—Bi1—N3—C1−69.4 (7)
N3—Bi1—O4—N2−36.8 (5)N3i—Bi1—N3—C54.1 (3)
N3i—Bi1—O4—N2−92.6 (5)O5i—Bi1—N3—C581.7 (5)
O5i—Bi1—O4—N2−142.9 (4)O5—Bi1—N3—C5−80.6 (5)
O5—Bi1—O4—N2−6.0 (4)O2—Bi1—N3—C5−158.3 (5)
O2—Bi1—O4—N248.4 (5)O2i—Bi1—N3—C533.0 (6)
O2i—Bi1—O4—N2−175.3 (5)O4—Bi1—N3—C5−56.9 (5)
O4i—Bi1—O4—N2113.7 (5)O4i—Bi1—N3—C5132.1 (5)
O1—Bi1—O4—N280.5 (5)O1—Bi1—N3—C5−140.3 (5)
O1i—Bi1—O4—N2144.7 (5)O1i—Bi1—N3—C5120.3 (5)
N3—Bi1—O5—N2158.3 (5)
D—H···AD—HH···AD···AD—H···A
N4—H7···O40.932.313.145 (10)149
Table 1

Selected bond lengths (Å)

Bi1—N32.444 (5)
Bi1—O52.470 (6)
Bi1—O22.564 (6)
Bi1—O42.626 (6)
Bi1—O12.703 (8)
Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N4—H7⋯O40.932.313.145 (10)149
  7 in total

1.  The space groups of point group C3: some corrections, some comments.

Authors:  Richard E Marsh
Journal:  Acta Crystallogr B       Date:  2002-09-24

Review 2.  Bismuth in medicine.

Authors:  Hongzhe Sun; Li Zhang; Ka-Yee Szeto
Journal:  Met Ions Biol Syst       Date:  2004

3.  Inhibition of SARS coronavirus helicase by bismuth complexes.

Authors:  Nan Yang; Julian A Tanner; Zai Wang; Jian-Dong Huang; Bo-Jian Zheng; Nianyong Zhu; Hongzhe Sun
Journal:  Chem Commun (Camb)       Date:  2007-08-16       Impact factor: 6.222

4.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

5.  Binding of bismuth to serum proteins: implication for targets of Bi(III) in blood plasma.

Authors:  Hongzhe Sun; Ka Yee Szeto
Journal:  J Inorg Biochem       Date:  2003-02-01       Impact factor: 4.155

6.  Synthetic and structural comparisons of bismuth(III) carboxylates synthesised under solvent-free and reflux conditions.

Authors:  Philip C Andrews; Glen B Deacon; Peter C Junk; Ish Kumar; Morry Silberstein
Journal:  Dalton Trans       Date:  2006-08-23       Impact factor: 4.390

7.  Structural characterisation of the first mononuclear bismuth porphyrin.

Authors:  Bernard Boitrel; Zakaria Halime; Lydie Michaudet; Mohamed Lachkar; Loïc Toupet
Journal:  Chem Commun (Camb)       Date:  2003-11-07       Impact factor: 6.222
  7 in total
  1 in total

1.  Bis[bis-(2,2'-bipyridine-κN,N')chloridocopper(II)] bis-(μ-2,6-pyridine-dicarboxyl-ato)-κO,N,O:O;κO:O,N,O-bis-[aqua-dichloridobismuthate(III)] penta-hydrate.

Authors:  Hong-Wei Wang; Wan-Lan Liu; Yu-Quan Feng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-11-02
  1 in total

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