Literature DB >> 21580551

4,4'-Bipyridinium bis-(μ-4-oxo-1,4-dihydropyridine-2,6-dicarboxyl-ato)bis-[aqua-hydroxido-anti-monate(III)] dihydrate.

Janet Soleimannejad, Jafar Attar Gharamaleki, Hossein Aghabozorg, Yaghoub Mohammadzadeh Azar Golenji.   

Abstract

The title compound, (C(10)H(10)N(2))[Sb(2)(C(7)H(2)NO(5))(2)(OH)(2)(H(2)O)(2)]·2H(2)O, consists of a binuclear anion, a diprotonated 4,4'-bipyridinium cation and two uncoordinated water mol-ecules. Each Sb(III) atom is six-coordinated by one chelating 4-oxidopyridine-2,6-dicarboxyl-ate ligand, one water mol-ecule, one OH group and one bridging O atom from a neighboring carboxyl-ate group in a distorted penta-gonal-pyramidal geometry, with the OH group at the apical position. The two pyridine rings in the bipyridinium cation are twisted with respect to each other, making a dihedral angle of 22.7 (1)°. The cations are connected to the anions by N-H⋯O hydrogen bonds, forming a chain. The coordinated water mol-ecules form hydrogen bonds with the oxido O atoms of the anion, building a two-dimensional sheet, which is further connected into a three-dimensional structure by O-H⋯O and C-H⋯O hydrogen bonds and C=O⋯π inter-actions [O⋯centroid distances = 3.1785 (17), 3.4737 (19) and 3.5685 (19) Å].

Entities:  

Year:  2010        PMID: 21580551      PMCID: PMC2983914          DOI: 10.1107/S1600536810010743

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


Related literature

For the use of 4,4′-bipyridine in the construction of supra­molecular architectures, see: Jia et al. (2009 ▶); Meng et al. (2009 ▶); Zhang et al. (2009 ▶). For binuclear complexes of SbIII/SbV with pyridine-2,6-dicarboxylic acid, see: Aghabozorg et al. (2005 ▶); Soleimannejad et al. (2008 ▶). For proton transfer compounds and their metal complexes, see: Aghabozorg et al. (2008 ▶). For environmental studies of anti­mony, see: Filella et al. (2002 ▶).

Experimental

Crystal data

(C10H10N2)[Sb2(C7H2NO5)2(OH)2(H2O)2]·2H2O M = 867.97 Triclinic, a = 7.7774 (9) Å b = 10.2465 (12) Å c = 17.773 (2) Å α = 80.255 (5)° β = 81.760 (5)° γ = 82.547 (5)° V = 1373.4 (3) Å3 Z = 2 Mo Kα radiation μ = 2.06 mm−1 T = 150 K 0.32 × 0.32 × 0.13 mm

Data collection

Bruker SMART 1000 CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.559, T max = 0.776 29846 measured reflections 6323 independent reflections 5762 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.021 wR(F 2) = 0.054 S = 1.05 6323 reflections 415 parameters H-atom parameters constrained Δρmax = 1.03 e Å−3 Δρmin = −0.61 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010743/hy2287sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010743/hy2287Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
(C10H10N2)[Sb2(C7H2NO5)2(OH)2(H2O)2]·2H2OZ = 2
Mr = 867.97F(000) = 852
Triclinic, P1Dx = 2.099 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.7774 (9) ÅCell parameters from 16661 reflections
b = 10.2465 (12) Åθ = 2.5–27.5°
c = 17.773 (2) ŵ = 2.06 mm1
α = 80.255 (5)°T = 150 K
β = 81.760 (5)°Block, colourless
γ = 82.547 (5)°0.32 × 0.32 × 0.13 mm
V = 1373.4 (3) Å3
Bruker SMART 1000 CCD diffractometer6323 independent reflections
Radiation source: fine-focus sealed tube5762 reflections with I > 2σ(I)
graphiteRint = 0.027
φ and ω scansθmax = 27.6°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −10→10
Tmin = 0.559, Tmax = 0.776k = −13→13
29846 measured reflectionsl = −23→23
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.054H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0291P)2 + 1.1343P] where P = (Fo2 + 2Fc2)/3
6323 reflections(Δ/σ)max = 0.002
415 parametersΔρmax = 1.02 e Å3
0 restraintsΔρmin = −0.61 e Å3
xyzUiso*/Ueq
Sb10.580591 (16)0.703688 (13)0.358013 (7)0.01090 (4)
Sb20.438680 (16)0.752017 (12)0.129483 (7)0.01011 (4)
O1W0.11728 (19)0.69329 (15)0.33900 (9)0.0163 (3)
H1A0.14200.62430.37120.020*
H1B0.01150.69490.33140.020*
O10.72456 (19)0.67130 (15)0.45745 (8)0.0150 (3)
O2W0.9042 (2)0.8814 (2)0.17638 (12)0.0439 (6)
H2A0.88780.94600.13960.053*
H2B1.01230.85200.17100.053*
O20.8151 (2)0.52864 (15)0.55669 (9)0.0170 (3)
O30.7165 (2)0.08698 (15)0.46954 (9)0.0189 (3)
O40.4341 (2)0.39130 (15)0.24797 (9)0.0172 (3)
O50.49471 (19)0.58946 (14)0.26877 (8)0.0141 (3)
O60.30385 (19)0.77857 (14)0.02920 (8)0.0145 (3)
O70.1851 (2)0.91893 (15)−0.06395 (9)0.0186 (3)
O80.23816 (19)1.36547 (14)0.03077 (8)0.0144 (3)
O90.5309 (2)1.06860 (15)0.25055 (9)0.0221 (4)
O100.49467 (19)0.86694 (14)0.22539 (8)0.0137 (3)
O110.80104 (18)0.69280 (15)0.29264 (8)0.0155 (3)
H11A0.79850.75790.25600.019*
O130.6824 (3)0.92019 (17)0.36682 (10)0.0296 (4)
H13B0.68560.96890.40070.035*
H13A0.63560.97340.33150.035*
O150.4245 (2)0.51911 (15)0.10194 (9)0.0172 (3)
H15B0.36150.48040.07920.021*
H15A0.41270.47290.14650.021*
O160.21023 (18)0.73191 (15)0.18620 (8)0.0146 (3)
H16A0.21200.70880.23460.018*
N10.6307 (2)0.48763 (17)0.39380 (10)0.0111 (3)
N20.3608 (2)0.96575 (17)0.09960 (9)0.0109 (3)
N3−0.1645 (2)0.95121 (18)−0.40617 (10)0.0148 (4)
H3A−0.20431.0024−0.44400.018*
N40.1423 (2)0.50965 (18)−0.09767 (10)0.0141 (3)
H4A0.18020.4608−0.05860.017*
C10.7559 (3)0.5527 (2)0.49466 (12)0.0128 (4)
C20.7105 (3)0.4426 (2)0.45717 (11)0.0111 (4)
C30.7429 (3)0.3094 (2)0.48443 (12)0.0128 (4)
H30.79970.28210.52790.015*
C40.6890 (3)0.2126 (2)0.44593 (11)0.0131 (4)
C50.6039 (3)0.2645 (2)0.37913 (12)0.0132 (4)
H50.56540.20680.35160.016*
C60.5793 (3)0.3989 (2)0.35577 (11)0.0113 (4)
C70.4945 (3)0.4624 (2)0.28500 (11)0.0117 (4)
C80.2517 (3)0.8969 (2)−0.00416 (12)0.0128 (4)
C90.2806 (3)1.0087 (2)0.03616 (11)0.0116 (4)
C100.2339 (3)1.1418 (2)0.01168 (11)0.0117 (4)
H100.17681.1676−0.03190.014*
C110.2727 (3)1.2403 (2)0.05286 (11)0.0114 (4)
C120.3553 (3)1.1902 (2)0.12072 (12)0.0129 (4)
H120.38181.24910.15080.016*
C130.3953 (3)1.0562 (2)0.14123 (11)0.0117 (4)
C140.4814 (3)0.9955 (2)0.21167 (12)0.0133 (4)
C150.1954 (3)0.6317 (2)−0.11368 (12)0.0146 (4)
H150.26850.6569−0.08290.017*
C160.1420 (3)0.7203 (2)−0.17571 (12)0.0142 (4)
H160.18060.8044−0.18730.017*
C170.0292 (3)0.6824 (2)−0.22106 (11)0.0118 (4)
C18−0.0372 (3)0.7772 (2)−0.28624 (11)0.0118 (4)
C19−0.0412 (3)0.9149 (2)−0.28961 (12)0.0155 (4)
H19−0.00040.9490−0.25100.019*
C20−0.1056 (3)1.0000 (2)−0.35033 (12)0.0170 (4)
H20−0.10821.0916−0.35260.020*
C21−0.1612 (3)0.8204 (2)−0.40566 (12)0.0153 (4)
H21−0.20140.7896−0.44550.018*
C22−0.0982 (3)0.7308 (2)−0.34594 (12)0.0139 (4)
H22−0.09640.6397−0.34550.017*
C23−0.0233 (3)0.5547 (2)−0.20217 (12)0.0148 (4)
H23−0.09770.5270−0.23140.018*
C240.0355 (3)0.4695 (2)−0.14003 (12)0.0154 (4)
H240.00100.3841−0.12750.019*
U11U22U33U12U13U23
Sb10.01408 (7)0.00955 (7)0.00914 (7)−0.00086 (5)−0.00371 (5)−0.00003 (5)
Sb20.01203 (7)0.00898 (7)0.00915 (7)−0.00093 (5)−0.00270 (5)0.00010 (5)
O1W0.0153 (7)0.0179 (8)0.0148 (7)−0.0018 (6)−0.0057 (6)0.0032 (6)
O10.0225 (8)0.0107 (7)0.0125 (7)−0.0030 (6)−0.0072 (6)0.0011 (6)
O2W0.0242 (9)0.0498 (13)0.0392 (12)0.0090 (9)0.0027 (8)0.0303 (10)
O20.0273 (8)0.0135 (7)0.0117 (7)−0.0020 (6)−0.0095 (6)−0.0005 (6)
O30.0331 (9)0.0092 (7)0.0156 (7)−0.0017 (6)−0.0117 (6)0.0016 (6)
O40.0273 (8)0.0122 (7)0.0145 (7)−0.0043 (6)−0.0110 (6)0.0000 (6)
O50.0191 (7)0.0102 (7)0.0139 (7)−0.0020 (6)−0.0069 (6)0.0003 (6)
O60.0214 (7)0.0097 (7)0.0134 (7)−0.0017 (6)−0.0070 (6)−0.0001 (6)
O70.0302 (8)0.0138 (7)0.0139 (7)−0.0005 (6)−0.0122 (6)−0.0013 (6)
O80.0220 (7)0.0084 (7)0.0128 (7)−0.0002 (6)−0.0066 (6)0.0011 (5)
O90.0396 (10)0.0115 (7)0.0190 (8)−0.0024 (7)−0.0175 (7)−0.0012 (6)
O100.0197 (7)0.0086 (7)0.0135 (7)−0.0017 (6)−0.0063 (6)0.0001 (6)
O110.0145 (7)0.0172 (8)0.0131 (7)−0.0020 (6)−0.0030 (6)0.0035 (6)
O130.0574 (12)0.0132 (8)0.0231 (9)−0.0055 (8)−0.0228 (8)−0.0006 (7)
O150.0258 (8)0.0110 (7)0.0162 (7)−0.0043 (6)−0.0087 (6)0.0006 (6)
O160.0139 (7)0.0180 (8)0.0112 (7)−0.0031 (6)−0.0021 (5)0.0012 (6)
N10.0140 (8)0.0104 (8)0.0089 (8)−0.0012 (6)−0.0033 (6)0.0001 (6)
N20.0131 (8)0.0098 (8)0.0096 (8)−0.0008 (6)−0.0028 (6)0.0000 (6)
N30.0184 (8)0.0148 (9)0.0105 (8)−0.0016 (7)−0.0050 (7)0.0030 (7)
N40.0177 (8)0.0129 (8)0.0106 (8)0.0020 (7)−0.0042 (7)0.0003 (7)
C10.0151 (9)0.0120 (9)0.0110 (9)−0.0006 (7)−0.0016 (7)−0.0018 (8)
C20.0124 (9)0.0135 (10)0.0079 (9)−0.0028 (7)−0.0020 (7)−0.0012 (7)
C30.0160 (9)0.0126 (10)0.0094 (9)−0.0013 (7)−0.0041 (7)0.0015 (7)
C40.0170 (9)0.0115 (9)0.0103 (9)−0.0012 (8)−0.0024 (7)0.0000 (7)
C50.0161 (9)0.0129 (10)0.0113 (9)−0.0022 (7)−0.0034 (7)−0.0014 (8)
C60.0122 (9)0.0127 (9)0.0090 (9)−0.0013 (7)−0.0025 (7)−0.0011 (7)
C70.0129 (9)0.0110 (9)0.0100 (9)0.0005 (7)−0.0022 (7)0.0010 (7)
C80.0155 (9)0.0111 (9)0.0114 (9)−0.0024 (7)−0.0016 (7)−0.0003 (8)
C90.0127 (9)0.0123 (10)0.0097 (9)−0.0014 (7)−0.0012 (7)−0.0012 (7)
C100.0130 (9)0.0130 (10)0.0090 (9)−0.0018 (7)−0.0038 (7)0.0005 (7)
C110.0132 (9)0.0104 (9)0.0095 (9)−0.0004 (7)−0.0002 (7)0.0002 (7)
C120.0161 (9)0.0112 (10)0.0113 (9)−0.0014 (7)−0.0032 (7)−0.0003 (8)
C130.0137 (9)0.0114 (9)0.0099 (9)−0.0011 (7)−0.0023 (7)−0.0010 (7)
C140.0167 (9)0.0117 (10)0.0111 (9)−0.0010 (7)−0.0041 (7)0.0005 (8)
C150.0153 (9)0.0144 (10)0.0157 (10)−0.0015 (8)−0.0054 (8)−0.0045 (8)
C160.0166 (9)0.0115 (10)0.0153 (10)−0.0033 (8)−0.0035 (8)−0.0012 (8)
C170.0121 (9)0.0118 (9)0.0105 (9)0.0002 (7)0.0001 (7)−0.0016 (8)
C180.0121 (9)0.0115 (9)0.0112 (9)−0.0021 (7)−0.0017 (7)0.0007 (8)
C190.0215 (10)0.0133 (10)0.0129 (10)−0.0029 (8)−0.0054 (8)−0.0019 (8)
C200.0224 (10)0.0133 (10)0.0158 (10)−0.0026 (8)−0.0053 (8)−0.0007 (8)
C210.0179 (10)0.0169 (10)0.0120 (10)−0.0035 (8)−0.0051 (8)−0.0010 (8)
C220.0177 (10)0.0118 (10)0.0128 (10)−0.0031 (8)−0.0040 (8)−0.0011 (8)
C230.0171 (10)0.0147 (10)0.0140 (10)−0.0035 (8)−0.0061 (8)−0.0012 (8)
C240.0195 (10)0.0120 (10)0.0152 (10)−0.0032 (8)−0.0048 (8)0.0004 (8)
Sb1—O111.9300 (15)N3—H3A0.8500
Sb1—O12.1816 (14)N4—C151.340 (3)
Sb1—N12.1972 (17)N4—C241.341 (3)
Sb1—O52.3381 (15)N4—H4A0.8500
Sb1—O132.4861 (17)C1—C21.505 (3)
Sb1—O102.7617 (14)C2—C31.372 (3)
Sb2—O161.9304 (14)C3—C41.431 (3)
Sb2—O62.1559 (14)C3—H30.9300
Sb2—N22.1908 (17)C4—C51.432 (3)
Sb2—O102.3468 (15)C5—C61.366 (3)
Sb2—O152.5350 (15)C5—H50.9300
Sb2—O52.7959 (14)C6—C71.513 (3)
O1W—H1A0.8500C8—C91.506 (3)
O1W—H1B0.8500C9—C101.378 (3)
O1—C11.293 (2)C10—C111.428 (3)
O2W—H2A0.8589C10—H100.9300
O2W—H2B0.8529C11—C121.435 (3)
O2—C11.230 (2)C12—C131.366 (3)
O3—C41.284 (3)C12—H120.9300
O4—C71.235 (3)C13—C141.507 (3)
O5—C71.285 (3)C15—C161.380 (3)
O6—C81.297 (2)C15—H150.9300
O7—C81.223 (2)C16—C171.402 (3)
O8—C111.281 (2)C16—H160.9300
O9—C141.230 (3)C17—C231.393 (3)
O10—C141.291 (3)C17—C181.487 (3)
O11—H11A0.8500C18—C221.397 (3)
O13—H13B0.8499C18—C191.399 (3)
O13—H13A0.8500C19—C201.378 (3)
O15—H15B0.8500C19—H190.9300
O15—H15A0.8501C20—H200.9300
O16—H16A0.8549C21—C221.383 (3)
N1—C21.348 (2)C21—H210.9300
N1—C61.350 (3)C22—H220.9300
N2—C91.347 (3)C23—C241.381 (3)
N2—C131.353 (3)C23—H230.9300
N3—C211.336 (3)C24—H240.9300
N3—C201.342 (3)
O11—Sb1—O188.73 (6)C2—C3—C4120.02 (18)
O11—Sb1—N187.40 (6)C2—C3—H3120.0
O1—Sb1—N172.28 (6)C4—C3—H3120.0
O11—Sb1—O582.88 (6)O3—C4—C3122.05 (18)
O1—Sb1—O5141.44 (5)O3—C4—C5122.18 (19)
N1—Sb1—O569.80 (6)C3—C4—C5115.77 (18)
O11—Sb1—O1379.47 (7)C6—C5—C4120.04 (19)
O1—Sb1—O1372.89 (5)C6—C5—H5120.0
N1—Sb1—O13142.91 (6)C4—C5—H5120.0
O5—Sb1—O13140.84 (5)N1—C6—C5122.63 (18)
O11—Sb1—O1078.80 (5)N1—C6—C7113.70 (17)
O1—Sb1—O10148.04 (5)C5—C6—C7123.67 (18)
N1—Sb1—O10135.33 (5)O4—C7—O5125.85 (18)
O5—Sb1—O1066.46 (5)O4—C7—C6119.32 (18)
O13—Sb1—O1075.93 (5)O5—C7—C6114.82 (17)
O16—Sb2—O684.67 (6)O7—C8—O6123.94 (19)
O16—Sb2—N289.44 (6)O7—C8—C9121.27 (18)
O6—Sb2—N272.66 (6)O6—C8—C9114.78 (17)
O16—Sb2—O1087.61 (6)N2—C9—C10122.26 (19)
O6—Sb2—O10141.57 (5)N2—C9—C8112.91 (17)
N2—Sb2—O1069.67 (6)C10—C9—C8124.82 (18)
O16—Sb2—O1584.54 (6)C9—C10—C11120.29 (18)
O6—Sb2—O1574.52 (5)C9—C10—H10119.9
N2—Sb2—O15147.04 (6)C11—C10—H10119.9
O10—Sb2—O15142.00 (5)O8—C11—C10122.67 (18)
O16—Sb2—O573.88 (5)O8—C11—C12121.74 (18)
O6—Sb2—O5145.16 (5)C10—C11—C12115.58 (18)
N2—Sb2—O5132.68 (5)C13—C12—C11120.15 (19)
O10—Sb2—O565.76 (5)C13—C12—H12119.9
O15—Sb2—O576.35 (5)C11—C12—H12119.9
H1A—O1W—H1B108.1N2—C13—C12122.65 (18)
C1—O1—Sb1120.34 (13)N2—C13—C14113.87 (17)
H2A—O2W—H2B107.6C12—C13—C14123.48 (18)
C7—O5—Sb1118.75 (12)O9—C14—O10125.98 (19)
C7—O5—Sb2127.75 (12)O9—C14—C13119.46 (18)
Sb1—O5—Sb2113.14 (6)O10—C14—C13114.56 (17)
C8—O6—Sb2120.80 (13)N4—C15—C16120.29 (19)
C14—O10—Sb2118.36 (12)N4—C15—H15119.9
C14—O10—Sb1127.57 (12)C16—C15—H15119.9
Sb2—O10—Sb1114.08 (5)C15—C16—C17119.5 (2)
Sb1—O11—H11A108.5C15—C16—H16120.2
Sb1—O13—H13B138.7C17—C16—H16120.2
Sb1—O13—H13A103.0C23—C17—C16118.27 (18)
H13B—O13—H13A103.5C23—C17—C18120.70 (19)
Sb2—O15—H15B137.7C16—C17—C18121.00 (19)
Sb2—O15—H15A103.5C22—C18—C19118.02 (18)
H15B—O15—H15A99.8C22—C18—C17120.69 (19)
Sb2—O16—H16A113.5C19—C18—C17121.29 (19)
C2—N1—C6119.08 (17)C20—C19—C18119.8 (2)
C2—N1—Sb1118.77 (13)C20—C19—H19120.1
C6—N1—Sb1122.11 (13)C18—C19—H19120.1
C9—N2—C13119.02 (17)N3—C20—C19120.3 (2)
C9—N2—Sb2118.66 (13)N3—C20—H20119.9
C13—N2—Sb2122.29 (13)C19—C20—H20119.9
C21—N3—C20121.90 (18)N3—C21—C22120.11 (19)
C21—N3—H3A116.7N3—C21—H21119.9
C20—N3—H3A121.4C22—C21—H21119.9
C15—N4—C24121.93 (18)C21—C22—C18119.90 (19)
C15—N4—H4A115.0C21—C22—H22120.0
C24—N4—H4A123.1C18—C22—H22120.0
O2—C1—O1123.94 (19)C24—C23—C17119.90 (19)
O2—C1—C2121.16 (19)C24—C23—H23120.0
O1—C1—C2114.88 (17)C17—C23—H23120.0
N1—C2—C3122.44 (19)N4—C24—C23120.1 (2)
N1—C2—C1113.16 (17)N4—C24—H24120.0
C3—C2—C1124.39 (18)C23—C24—H24120.0
O11—Sb1—O1—C1−94.49 (15)Sb1—N1—C2—C1−0.4 (2)
N1—Sb1—O1—C1−6.82 (14)O2—C1—C2—N1173.49 (19)
O5—Sb1—O1—C1−17.6 (2)O1—C1—C2—N1−5.3 (3)
O13—Sb1—O1—C1−173.86 (16)O2—C1—C2—C3−5.3 (3)
O10—Sb1—O1—C1−160.75 (13)O1—C1—C2—C3175.91 (19)
O11—Sb1—O5—C798.21 (15)N1—C2—C3—C4−0.9 (3)
O1—Sb1—O5—C719.31 (19)C1—C2—C3—C4177.82 (19)
N1—Sb1—O5—C78.37 (14)C2—C3—C4—O3−179.9 (2)
O13—Sb1—O5—C7161.79 (14)C2—C3—C4—C50.5 (3)
O10—Sb1—O5—C7179.06 (16)O3—C4—C5—C6−179.3 (2)
O11—Sb1—O5—Sb2−75.41 (7)C3—C4—C5—C60.2 (3)
O1—Sb1—O5—Sb2−154.31 (7)C2—N1—C6—C50.4 (3)
N1—Sb1—O5—Sb2−165.25 (8)Sb1—N1—C6—C5−177.52 (15)
O13—Sb1—O5—Sb2−11.83 (12)C2—N1—C6—C7−178.94 (17)
O10—Sb1—O5—Sb25.44 (4)Sb1—N1—C6—C73.1 (2)
O16—Sb2—O5—C785.91 (16)C4—C5—C6—N1−0.7 (3)
O6—Sb2—O5—C731.7 (2)C4—C5—C6—C7178.54 (18)
N2—Sb2—O5—C7159.63 (15)Sb1—O5—C7—O4171.21 (16)
O10—Sb2—O5—C7−179.36 (17)Sb2—O5—C7—O4−16.2 (3)
O15—Sb2—O5—C7−2.28 (15)Sb1—O5—C7—C6−9.6 (2)
O16—Sb2—O5—Sb1−101.17 (7)Sb2—O5—C7—C6163.02 (12)
O6—Sb2—O5—Sb1−155.40 (7)N1—C6—C7—O4−176.23 (18)
N2—Sb2—O5—Sb1−27.44 (10)C5—C6—C7—O44.4 (3)
O10—Sb2—O5—Sb1−6.43 (5)N1—C6—C7—O54.5 (3)
O15—Sb2—O5—Sb1170.65 (7)C5—C6—C7—O5−174.85 (19)
O16—Sb2—O6—C895.22 (15)Sb2—O6—C8—O7174.97 (16)
N2—Sb2—O6—C84.14 (15)Sb2—O6—C8—C9−4.5 (2)
O10—Sb2—O6—C815.9 (2)C13—N2—C9—C100.6 (3)
O15—Sb2—O6—C8−178.98 (16)Sb2—N2—C9—C10−177.32 (15)
O5—Sb2—O6—C8146.75 (13)C13—N2—C9—C8179.79 (17)
O16—Sb2—O10—C14−100.59 (15)Sb2—N2—C9—C81.8 (2)
O6—Sb2—O10—C14−22.27 (19)O7—C8—C9—N2−177.86 (19)
N2—Sb2—O10—C14−10.30 (14)O6—C8—C9—N21.6 (3)
O15—Sb2—O10—C14−178.59 (13)O7—C8—C9—C101.3 (3)
O5—Sb2—O10—C14−173.98 (16)O6—C8—C9—C10−179.23 (19)
O16—Sb2—O10—Sb178.87 (7)N2—C9—C10—C111.2 (3)
O6—Sb2—O10—Sb1157.19 (7)C8—C9—C10—C11−177.87 (18)
N2—Sb2—O10—Sb1169.16 (8)C9—C10—C11—O8177.21 (19)
O15—Sb2—O10—Sb10.88 (11)C9—C10—C11—C12−2.1 (3)
O5—Sb2—O10—Sb15.48 (5)O8—C11—C12—C13−177.93 (19)
O11—Sb1—O10—C14−100.08 (17)C10—C11—C12—C131.4 (3)
O1—Sb1—O10—C14−31.2 (2)C9—N2—C13—C12−1.4 (3)
N1—Sb1—O10—C14−174.64 (15)Sb2—N2—C13—C12176.48 (15)
O5—Sb1—O10—C14172.88 (17)C9—N2—C13—C14178.68 (17)
O13—Sb1—O10—C14−18.26 (16)Sb2—N2—C13—C14−3.4 (2)
O11—Sb1—O10—Sb280.52 (7)C11—C12—C13—N20.3 (3)
O1—Sb1—O10—Sb2149.42 (8)C11—C12—C13—C14−179.77 (18)
N1—Sb1—O10—Sb25.96 (11)Sb2—O10—C14—O9−168.47 (18)
O5—Sb1—O10—Sb2−6.53 (5)Sb1—O10—C14—O912.2 (3)
O13—Sb1—O10—Sb2162.33 (8)Sb2—O10—C14—C1312.0 (2)
O11—Sb1—N1—C292.96 (15)Sb1—O10—C14—C13−167.43 (12)
O1—Sb1—N1—C23.46 (14)N2—C13—C14—O9174.43 (19)
O5—Sb1—N1—C2176.33 (16)C12—C13—C14—O9−5.5 (3)
O13—Sb1—N1—C224.3 (2)N2—C13—C14—O10−6.0 (3)
O10—Sb1—N1—C2164.14 (12)C12—C13—C14—O10174.13 (19)
O11—Sb1—N1—C6−89.12 (16)C24—N4—C15—C16−0.7 (3)
O1—Sb1—N1—C6−178.62 (17)N4—C15—C16—C171.2 (3)
O5—Sb1—N1—C6−5.75 (14)C15—C16—C17—C23−0.9 (3)
O13—Sb1—N1—C6−157.80 (14)C15—C16—C17—C18177.29 (19)
O10—Sb1—N1—C6−17.93 (19)C23—C17—C18—C22−23.5 (3)
O16—Sb2—N2—C9−87.61 (15)C16—C17—C18—C22158.33 (19)
O6—Sb2—N2—C9−3.03 (14)C23—C17—C18—C19156.3 (2)
O10—Sb2—N2—C9−175.27 (16)C16—C17—C18—C19−21.9 (3)
O15—Sb2—N2—C9−8.6 (2)C22—C18—C19—C200.6 (3)
O5—Sb2—N2—C9−154.87 (13)C17—C18—C19—C20−179.2 (2)
O16—Sb2—N2—C1394.50 (16)C21—N3—C20—C19−0.8 (3)
O6—Sb2—N2—C13179.08 (17)C18—C19—C20—N30.0 (3)
O10—Sb2—N2—C136.84 (14)C20—N3—C21—C220.9 (3)
O15—Sb2—N2—C13173.56 (13)N3—C21—C22—C18−0.2 (3)
O5—Sb2—N2—C1327.24 (18)C19—C18—C22—C21−0.5 (3)
Sb1—O1—C1—O2−169.95 (16)C17—C18—C22—C21179.29 (19)
Sb1—O1—C1—C28.8 (2)C16—C17—C23—C240.2 (3)
C6—N1—C2—C30.4 (3)C18—C17—C23—C24−178.03 (19)
Sb1—N1—C2—C3178.41 (15)C15—N4—C24—C23−0.1 (3)
C6—N1—C2—C1−178.42 (17)C17—C23—C24—N40.3 (3)
D—H···AD—HH···AD···AD—H···A
O1W—H1A···O2i0.851.882.725 (2)177
O1W—H1B···O11ii0.851.872.704 (2)167
O2W—H2A···O7iii0.861.852.703 (2)171
O2W—H2B···O16iv0.851.862.669 (2)157
O11—H11A···O2W0.851.902.688 (2)154
O16—H16A···O1W0.851.882.684 (2)155
O13—H13A···O90.851.832.672 (2)173
O13—H13B···O3v0.851.922.764 (2)173
O15—H15A···O40.851.882.709 (2)166
O15—H15B···O8vi0.851.982.823 (2)171
N3—H3A···O3vii0.851.782.624 (2)171
N4—H4A···O8vi0.851.802.648 (2)173
C3—H3···O1Wi0.932.603.460 (3)154
C5—H5···O9vi0.932.533.434 (3)164
C12—H12···O4v0.932.553.470 (3)172
C15—H15···O60.932.593.415 (3)149
C19—H19···O2Wiii0.932.603.484 (3)160
C20—H20···O1Wviii0.932.253.172 (3)172
C21—H21···O1ix0.932.443.358 (3)170
C22—H22···O2ix0.932.453.107 (3)128
C24—H24···O16x0.932.573.261 (3)131
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯ADAD—H⋯A
O1W—H1A⋯O2i0.851.882.725 (2)177
O1W—H1B⋯O11ii0.851.872.704 (2)167
O2W—H2A⋯O7iii0.861.852.703 (2)171
O2W—H2B⋯O16iv0.851.862.669 (2)157
O11—H11A⋯O2W0.851.902.688 (2)154
O16—H16A⋯O1W0.851.882.684 (2)155
O13—H13A⋯O90.851.832.672 (2)173
O13—H13B⋯O3v0.851.922.764 (2)173
O15—H15A⋯O40.851.882.709 (2)166
O15—H15B⋯O8vi0.851.982.823 (2)171
N3—H3A⋯O3vii0.851.782.624 (2)171
N4—H4A⋯O8vi0.851.802.648 (2)173
C3—H3⋯O1Wi0.932.603.460 (3)154
C5—H5⋯O9vi0.932.533.434 (3)164
C12—H12⋯O4v0.932.553.470 (3)172
C15—H15⋯O60.932.593.415 (3)149
C19—H19⋯O2Wiii0.932.603.484 (3)160
C20—H20⋯O1Wviii0.932.253.172 (3)172
C21—H21⋯O1ix0.932.443.358 (3)170
C22—H22⋯O2ix0.932.453.107 (3)128
C24—H24⋯O16x0.932.573.261 (3)131

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) .

  5 in total

1.  A short history of SHELX.

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

2.  4,4'-Bipyridinium bis(perchlorate)-4-aminobenzoic acid-4,4'-bipyridine-water (1/4/2/2).

Authors:  Qun-Hui Meng; Lu Han; Jian-Dong Hou; Yi-Fan Luo; Rong-Hua Zeng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-12-17

3.  Bis(4,4'-bipyridinium) di-μ-hydroxido-bis-[dihydroxido(pyridine-2,6-dicarboxyl-ato)anti-monate(III,V)] octa-hydrate.

Authors:  Janet Soleimannejad; Hossein Aghabozorg; Yaghoub Mohammadzadeh Azar Golenji; Jafar Attar Gharamaleki; Harry Adams
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-01-23

4.  Bis[4-(4-pyridyl)pyridinium] μ-4,4'-bipyridine-bis-[tetra-aqua-(4,4'-bipyridine)manganese(II)] bis-(5-sulfonatobenzene-1,3-dicarboxyl-ate) 4,4'-bipyridine solvate penta-deca-hydrate.

Authors:  Bing-Yu Zhang; Jing-Jing Nie; Duan-Jun Xu
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-22

5.  4,4'-Bipyridinium 1,4-phenyl-ene-diacetate.

Authors:  Maomao Jia; Xianlin Liu; Jing Miao; Wei Xiong; Zilu Chen
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-09-19
  5 in total

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