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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): m467–m468.
Published online 2010 March 31. doi:  10.1107/S1600536810010743
PMCID: PMC2983914

4,4′-Bipyridinium bis­(μ-4-oxo-1,4-dihydropyridine-2,6-dicarboxyl­ato)bis­[aqua­hydroxido­anti­monate(III)] dihydrate

Abstract

The title compound, (C10H10N2)[Sb2(C7H2NO5)2(OH)2(H2O)2]·2H2O, consists of a binuclear anion, a diprotonated 4,4′-bipyridinium cation and two uncoordinated water mol­ecules. Each SbIII atom is six-coordinated by one chelating 4-oxidopyridine-2,6-dicarboxyl­ate ligand, one water mol­ecule, one OH group and one bridging O atom from a neighboring carboxyl­ate group in a distorted penta­gonal-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 mol­ecules 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 inter­actions [O(...)centroid distances = 3.1785 (17), 3.4737 (19) and 3.5685 (19) Å].

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-66-0m467-scheme1.jpg

Experimental

Crystal data

  • (C10H10N2)[Sb2(C7H2NO5)2(OH)2(H2O)2]·2H2O
  • M r = 867.97
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m467-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

Financial support from Ilam University is gratefully acknowledged.

supplementary crystallographic information

Comment

It is well known that 4,4'-bipyridine is an excellent candidate for the construction of three-dimensional network motifs. It can act as coordinating or bridging ligand or as proton acceptor agent (Jia et al., 2009; Meng et al., 2009; Zhang et al., 2009). The binuclear mixed ligand SbIII/SbV compounds have been recently reported, in which pyridinedicarboxylic acid has been used as chelating ligand (Soleimannejad et al., 2008). For more details regarding proton transfer compounds and their metal complexes see our review article (Aghabozorg et al., 2008).

The title compound is composed of a binuclear [Sb(hypydc)(OH)(H2O)]22- (H3hypydc = 4-hydroxypyridine-2,6-dicarboxylic acid) anion, a diprotonated 4,4'-bipyridinium cation and two uncoordinated water molecules (Fig. 1). In the binuclear complex anion, each SbIII atom is six-coordinated by one chelating (hypydc)3- ligand through its one N and two O atoms, one O atom from a terminal OH group, one O atom from a water molecule and one O atom from a neighboring carboxylate group as bridging ligand in a distorted pentagonal pyramidal geometry (Fig. 2). The relatively weaker Sb1—O10 [2.7617 (14) Å] and Sb2—O5 [2.7959 (14) Å] interactions connect the two anionic units into a binuclear complex through sharing O atoms of the carboxylate groups. The OH group is located at the apical position [Sb1—O11 = 1.9300 (15) and Sb2—O16 = 1.9304 (14) Å] and the rest O4N set forms the basal plane. It is supposed that this OH group is formed during the partial hydrolysis of SbCl3 to SbOCl, which is further hydrolyzed to Sb(OH)3, because free SbIII ion is stable in solution only at very high acidities (Filella et al., 2002). The Sb1—N1 and Sb2—N2 bond distances are 2.197 (3) and 2.191 (3) Å, respectively, which are comparable with the bond distances of SbIII binuclear complex with pyridine-2,6-dicarboxylic acid (Aghabozorg et al., 2005). The SbIII atoms deviate by 0.272 (5) and 0.249 (2) Å from the mean basal planes. The bond angles indicate that the lone-pairs on SbIII atoms are stereochemically active and stand at the trans positions to the OH groups. In the 4,4'-bipyridinium cation, the two pyridine rings are twisted with respect to each other, making a dihedral angle of 22.7 (1)°, which indicates the flexibility of the central C—C bond.

The intramolecular hydrogen bonds O13—H13A···O9 and O15—H15A···O4 are present in the anionic complex (Table 1). The 4,4'-bipyridinium cations are hydrogen bonded to these anions by two distinct N3—H3A···O3vii and N4—H4A···O8vi hydrogen bonds [symmetry codes: (vi) x, y-1, z; (vii) x-1, y+1, z-1], forming one-dimensional chains. The coordinated water molecules act as donors with respect to oxido O atoms of the (hypydc)3- ligands from neighboring chains, building a two-dimensional sheet (Fig. 3). These sheets are further connected into a three-dimensional structure by O—H···O and C—H···O hydrogen-bonding interactions involving coordinated terminal OH group as well as uncoordinated water molecules. A noticeable feature of the title compound is the presence of C═O···π interactions between C═O groups and pyridyl rings of 4,4'-bipyridinium cations. The O···π distances are 3.4737 (19) Å for C4═O3···Cg1 (1-x, 1-y, -z), 3.1785 (17) Å for C11═O8···Cg2 (-x, 2-y, -z) and 3.5685 (19) Å for C14═O9···Cg1 (-x, 2-y,-z) [Cg1 and Cg2 are the centroids of N3, C18—C22 ring and N4, C15, C16, C17, C23, C24 ring]. The crystal packing diagram of the title compound is shown in Fig. 4.

Experimental

The title compound was prepared by the refluxing of 4,4'-bipyridine (312 mg, 2 mmol), 4-hydroxypyridine-2,6-dicarboxylic acid (183 mg, 1 mmol) and SbCl3 (228 mg, 1 mmol) in water (50 ml) in a 2:1:1 molar ratio for several hours. Colorless crystals were obtained by slow evaporation of the solvent at room temperature. The highest residual electron density was found 0.92 Å from O13 and the deepest hole 0.79 Å from Sb2.

Refinement

C- and N-bound H atoms were positioned geometrically and treated as riding atoms, with C—H = 0.93 and N—H = 0.85 Å and with Uiso(H) = 1.2Ueq(C, N). H atoms on water molecules and hydroxy groups were observed on a difference Fourier map and refined as riding, with O—H = 0.85 Å and Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
Molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level. Two uncoordinated water molecules are omitted for clarity.
Fig. 2.
Distorted pentagonal pyramidal geometries around the SbIII atoms in the anionic complex.
Fig. 3.
Hydrogen bonding (dashed lines) between 4,4'-bipyridinium cations, [Sb(hypydc)(OH)(H2O)]22- anions and uncoordinated water molecules.
Fig. 4.
Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

(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

Data collection

Bruker SMART 1000 CCD diffractometer6323 independent reflections
Radiation source: fine-focus sealed tube5762 reflections with I > 2σ(I)
graphiteRint = 0.027
[var phi] 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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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*

Atomic displacement parameters (Å2)

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)

Geometric parameters (Å, °)

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)

Hydrogen-bond geometry (Å, °)

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

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, −y+2, −z; (iv) x+1, y, z; (v) x, y+1, z; (vi) x, y−1, z; (vii) x−1, y+1, z−1; (viii) −x, −y+2, −z; (ix) x−1, y, z−1; (x) −x, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2287).

References

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