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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2051.
Published online 2008 October 4. doi:  10.1107/S1600536808031620
PMCID: PMC2959743

2,2′-Dinitro-5,5′-dithio­dibenzoic acid

Abstract

In the title compound, C14H8N2O8S2, the asymmetric unit contains two independent 2,2′-dinitro-5,5′-dithio­dibenzoic acid (Dina) mol­ecules with roughly the same conformation. In the crystal structure, strong inter­molecular O—H(...)O hydrogen bonds link the organic mol­ecules into a one-dimensional zigzag chain along the a axis. The dihedral angles between the two aromatic rings [109.3 (2) and 103.1 (3)°] are larger than that (88.95°) observed in a structure of the compound with a solvent water mol­ecule [Shefter & Kalman (1969), J. Chem. Soc. D, p. 1027]. Such a difference may be explained by the occurrence of O—H(...)O hydrogen bonds involving the water mol­ecule in the previously reported structure.

Related literature

For general background, see: Gudbjarlson et al. (1991 [triangle]); Li et al. (2006 [triangle]); Luo et al. (2007 [triangle]); Ye et al. (2005 [triangle]). For a related structure, see: Shefter & Kalman (1969 [triangle])

An external file that holds a picture, illustration, etc.
Object name is e-64-o2051-scheme1.jpg

Experimental

Crystal data

  • C14H8N2O8S2
  • M r = 396.34
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2051-efi1.jpg
  • a = 7.875 (2) Å
  • b = 14.695 (4) Å
  • c = 15.116 (5) Å
  • α = 111.480 (5)°
  • β = 101.182 (5)°
  • γ = 90.572 (5)°
  • V = 1590.6 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.39 mm−1
  • T = 298 (2) K
  • 0.21 × 0.17 × 0.15 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.921, T max = 0.942
  • 8041 measured reflections
  • 5555 independent reflections
  • 3077 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.051
  • wR(F 2) = 0.171
  • S = 0.92
  • 5555 reflections
  • 473 parameters
  • H-atom parameters constrained
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 [triangle]), ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031620/dn2385sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031620/dn2385Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The author is grateful to Lishui University for financial support.

supplementary crystallographic information

Comment

Until now, various flexible carboxylate ligands can often be employed due to their versatile coordination modes and high structural stability. In particular, multi-benzenecarboxylate ligands have been shown to be good building blocks in the design of metal-organic materials (Li et al., 2006; Luo et al., 2007; Gudbjarlson et al., 1991). On the other hand, relative strong hydrogen bondings play an important role in the formation of the ultimate netwrok (Ye et al., 2005). Originally, we attempted to synthesize a complex in the presence of metal salt. However, we only obtain the starting organic material (I).

In the title compound, [C14H8N2O8S]2, the asymmetric unit is built up by two independent 5,5'-dithiobis(2-nitrobenzcic-acid) (Dina) molecules having roughly the same conformation (Fig. 1). The geometric parameters for (I) are in the usual range. The dihedral angles between the two aromatic rings in the molecules are 109.3 (2)° and 103.1 (3)°, respectively, which indicate a twisted conformation between phenyl rings. A similar [C14H8N2O8S, H2O] compound, has been previously published (Shefter & Kalman, 1969). In this previous structure, the occurrence of the water molecule which acts as donor and acceptor, links the organic molecules to build up a sheet whereas in the title compound, the O—H···O hydrogen bonds form chains which develop parallel to the a axis (Table 1, Fig.2). In the previously reported compound, [C14H8N2O8S, H2O], the dihedral angles between the two aromatic rings is slightly smaller (88.95°) than in the title compound. Such difference might result from the occurrence of the water molecule which interconnects the oragnic molecule.

Experimental

5,5'-dithiobis(2-nitrobenzcic-acid) (21 mg,0.05 mmol), CoSo4 (13 mg, 0.06 mmol). were added in methanol. The mixture was refluxed under stirring for six hours. After cooling the resulting mixture to room temperature, some single crystals appeared within two weeks.

Refinement

All H atoms attached to C and O atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) and O—H = 0.82 Å with Uiso(H) = 1.2Ueq(C, O).

Figures

Fig. 1.
Molecular view of (I) with the atom-labeling scheme. scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii..
Fig. 2.
Partial packing view showing the formation of the chain though O—H···O hydrogen bonds. H bonds are shown as dashed line. H atoms not involved in H bonds have been omitted for clarity. [Symmetry codes: (i) x, y + 1, z; (ii) ...

Crystal data

C14H8N2O8S2Z = 4
Mr = 396.34F(000) = 808
Triclinic, P1Dx = 1.655 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.875 (2) ÅCell parameters from 5555 reflections
b = 14.695 (4) Åθ = 1.5–25.1°
c = 15.116 (5) ŵ = 0.39 mm1
α = 111.480 (5)°T = 298 K
β = 101.182 (5)°Block, colourless
γ = 90.572 (5)°0.21 × 0.17 × 0.15 mm
V = 1590.6 (8) Å3

Data collection

Bruker APEXII area-detector diffractometer5555 independent reflections
Radiation source: fine-focus sealed tube3077 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 25.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.921, Tmax = 0.942k = −17→16
8041 measured reflectionsl = −18→15

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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H-atom parameters constrained
S = 0.92w = 1/[σ2(Fo2) + (0.1043P)2] where P = (Fo2 + 2Fc2)/3
5555 reflections(Δ/σ)max < 0.001
473 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = −0.46 e Å3

Special details

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)

xyzUiso*/Ueq
S1−0.01726 (16)0.70300 (8)0.33908 (9)0.0468 (4)
S2−0.04932 (15)0.59689 (8)0.39126 (9)0.0433 (3)
N10.3900 (5)1.0562 (3)0.6593 (3)0.0487 (11)
N20.5648 (5)0.3610 (3)0.3567 (3)0.0430 (10)
O110.3554 (4)1.1261 (2)0.5124 (3)0.0592 (10)
H1A0.34281.17490.49840.089*
O120.1174 (4)1.0668 (2)0.3939 (3)0.0524 (9)
O130.5428 (5)1.0529 (3)0.6900 (3)0.0876 (15)
O140.3084 (5)1.1242 (3)0.6944 (3)0.0700 (12)
O210.1194 (4)0.2278 (2)0.3491 (3)0.0538 (10)
H2A0.13080.17710.35970.081*
O220.3681 (4)0.2775 (2)0.4591 (3)0.0584 (10)
O230.5385 (5)0.2744 (2)0.3064 (3)0.0657 (11)
O240.7108 (4)0.4035 (2)0.3973 (3)0.0579 (10)
C110.1118 (5)0.8035 (3)0.4363 (3)0.0316 (10)
C120.1199 (5)0.8905 (3)0.4200 (3)0.0332 (10)
H120.05910.89270.36170.040*
C130.2177 (5)0.9741 (3)0.4898 (3)0.0326 (10)
C140.2998 (5)0.9692 (3)0.5775 (3)0.0332 (10)
C150.2940 (5)0.8827 (3)0.5935 (3)0.0364 (11)
H150.35360.88070.65210.044*
C160.2006 (5)0.7996 (3)0.5234 (3)0.0330 (10)
H160.19690.74130.53420.040*
C210.1340 (5)0.5290 (3)0.3762 (3)0.0340 (11)
C220.1208 (6)0.4352 (3)0.3793 (3)0.0403 (12)
H220.01540.40940.38310.048*
C230.2633 (5)0.3803 (3)0.3768 (3)0.0339 (11)
C240.4171 (5)0.4200 (3)0.3685 (3)0.0345 (11)
C250.4336 (6)0.5117 (3)0.3644 (3)0.0380 (11)
H250.53880.53620.35890.046*
C260.2938 (5)0.5661 (3)0.3684 (3)0.0359 (11)
H260.30410.62820.36600.043*
C1310.2281 (5)1.0620 (3)0.4637 (3)0.0342 (10)
C2310.2520 (5)0.2874 (3)0.3953 (3)0.0377 (11)
S30.08887 (17)0.82074 (8)0.15577 (9)0.0454 (4)
S40.02988 (15)0.67435 (8)0.09932 (9)0.0406 (3)
N30.2790 (5)0.9447 (3)−0.1503 (3)0.0395 (9)
N40.6705 (5)0.4718 (3)0.1507 (3)0.0427 (10)
O310.2018 (4)1.1464 (2)0.1163 (2)0.0482 (9)
H3A0.20361.20300.11860.072*
O320.3339 (4)1.1224 (2)−0.0084 (2)0.0509 (9)
O330.1633 (5)0.9729 (3)−0.1961 (3)0.0640 (10)
O340.4258 (4)0.9351 (3)−0.1681 (2)0.0581 (10)
O410.3935 (5)0.3091 (2)0.0261 (3)0.0535 (9)
H4A0.39560.25350.02650.080*
O420.2379 (4)0.3353 (2)0.1412 (2)0.0441 (8)
O430.6680 (4)0.4104 (2)0.1883 (3)0.0530 (9)
O440.7995 (4)0.4923 (3)0.1241 (3)0.0688 (11)
C310.1522 (6)0.8507 (3)0.0627 (3)0.0363 (11)
C320.1794 (5)0.9510 (3)0.0841 (3)0.0377 (11)
H320.16710.99590.14410.045*
C330.2250 (5)0.9841 (3)0.0158 (3)0.0330 (10)
C340.2427 (5)0.9141 (3)−0.0736 (3)0.0331 (10)
C350.2196 (6)0.8161 (3)−0.0944 (4)0.0430 (12)
H350.23380.7712−0.15400.052*
C360.1747 (6)0.7836 (3)−0.0259 (3)0.0412 (12)
H360.15960.7166−0.03940.049*
C410.2267 (6)0.6214 (3)0.1214 (3)0.0360 (11)
C420.2104 (6)0.5236 (3)0.1103 (3)0.0355 (11)
H420.10020.49250.09810.043*
C430.3533 (5)0.4716 (3)0.1167 (3)0.0314 (10)
C440.5177 (6)0.5213 (3)0.1368 (3)0.0389 (11)
C450.5381 (6)0.6202 (3)0.1518 (3)0.0457 (13)
H450.64840.65210.16650.055*
C460.3911 (6)0.6708 (3)0.1446 (3)0.0422 (12)
H460.40230.73720.15520.051*
C3310.2575 (6)1.0908 (3)0.0403 (4)0.0390 (12)
C4310.3248 (6)0.3645 (3)0.0970 (3)0.0354 (11)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0637 (8)0.0279 (6)0.0414 (7)−0.0014 (6)−0.0062 (6)0.0134 (6)
S20.0457 (7)0.0277 (6)0.0567 (8)0.0010 (5)0.0101 (6)0.0167 (6)
N10.054 (3)0.035 (2)0.050 (3)−0.009 (2)0.002 (2)0.013 (2)
N20.047 (2)0.044 (3)0.045 (2)0.002 (2)0.007 (2)0.026 (2)
O110.067 (2)0.045 (2)0.071 (2)−0.0140 (18)0.0039 (19)0.0339 (19)
O120.053 (2)0.044 (2)0.069 (2)0.0025 (16)0.0034 (18)0.0375 (19)
O130.060 (3)0.074 (3)0.100 (3)−0.018 (2)−0.026 (2)0.021 (3)
O140.095 (3)0.037 (2)0.058 (3)−0.003 (2)0.005 (2)0.001 (2)
O210.058 (2)0.0334 (19)0.071 (2)−0.0089 (16)0.0007 (18)0.0273 (18)
O220.057 (2)0.051 (2)0.072 (2)−0.0115 (17)−0.0105 (19)0.040 (2)
O230.073 (2)0.033 (2)0.080 (3)0.0124 (18)0.014 (2)0.009 (2)
O240.0402 (19)0.066 (2)0.074 (3)0.0021 (17)0.0096 (18)0.035 (2)
C110.040 (2)0.022 (2)0.033 (2)0.0046 (19)0.009 (2)0.0091 (19)
C120.037 (2)0.032 (2)0.035 (2)0.0096 (19)0.012 (2)0.016 (2)
C130.031 (2)0.032 (2)0.038 (3)0.0060 (19)0.010 (2)0.016 (2)
C140.027 (2)0.030 (2)0.043 (3)0.0017 (18)0.012 (2)0.012 (2)
C150.044 (3)0.033 (3)0.034 (3)0.007 (2)0.008 (2)0.016 (2)
C160.037 (2)0.025 (2)0.041 (3)0.0098 (18)0.011 (2)0.015 (2)
C210.041 (2)0.025 (2)0.035 (3)−0.0025 (19)0.009 (2)0.009 (2)
C220.051 (3)0.028 (2)0.039 (3)−0.006 (2)0.003 (2)0.014 (2)
C230.041 (2)0.026 (2)0.035 (3)−0.001 (2)0.005 (2)0.015 (2)
C240.037 (2)0.032 (2)0.038 (3)0.003 (2)0.008 (2)0.017 (2)
C250.045 (3)0.032 (3)0.038 (3)−0.005 (2)0.007 (2)0.016 (2)
C260.047 (3)0.021 (2)0.040 (3)0.002 (2)0.014 (2)0.010 (2)
C1310.037 (2)0.028 (2)0.042 (3)0.003 (2)0.018 (2)0.013 (2)
C2310.040 (2)0.028 (2)0.047 (3)−0.002 (2)0.013 (2)0.016 (2)
S30.0688 (8)0.0302 (6)0.0422 (7)0.0033 (6)0.0186 (6)0.0161 (6)
S40.0442 (7)0.0307 (6)0.0500 (7)−0.0005 (5)0.0062 (6)0.0207 (6)
N30.046 (2)0.038 (2)0.037 (2)0.0009 (19)0.010 (2)0.0160 (19)
N40.043 (2)0.032 (2)0.048 (2)−0.0015 (19)0.008 (2)0.011 (2)
O310.063 (2)0.0243 (17)0.057 (2)0.0022 (16)0.0247 (18)0.0081 (17)
O320.078 (2)0.0269 (17)0.053 (2)−0.0034 (16)0.0255 (19)0.0158 (16)
O330.068 (2)0.076 (3)0.064 (2)0.019 (2)0.014 (2)0.044 (2)
O340.058 (2)0.072 (3)0.051 (2)0.0025 (19)0.0209 (18)0.026 (2)
O410.080 (2)0.0263 (18)0.061 (2)−0.0009 (18)0.030 (2)0.0173 (18)
O420.0558 (19)0.0312 (17)0.055 (2)−0.0011 (15)0.0257 (17)0.0209 (16)
O430.054 (2)0.048 (2)0.067 (2)0.0120 (16)0.0143 (18)0.0325 (19)
O440.043 (2)0.074 (3)0.109 (3)0.0074 (19)0.035 (2)0.047 (2)
C310.047 (3)0.027 (2)0.035 (3)0.003 (2)0.004 (2)0.015 (2)
C320.042 (2)0.029 (2)0.040 (3)−0.002 (2)0.006 (2)0.012 (2)
C330.031 (2)0.027 (2)0.040 (3)−0.0004 (18)0.005 (2)0.013 (2)
C340.033 (2)0.031 (2)0.038 (3)−0.0006 (19)0.009 (2)0.015 (2)
C350.051 (3)0.034 (3)0.043 (3)0.001 (2)0.013 (2)0.012 (2)
C360.049 (3)0.027 (2)0.051 (3)−0.001 (2)0.010 (2)0.019 (2)
C410.048 (3)0.027 (2)0.032 (2)−0.005 (2)0.003 (2)0.014 (2)
C420.046 (3)0.023 (2)0.036 (3)−0.007 (2)0.004 (2)0.012 (2)
C430.036 (2)0.024 (2)0.035 (2)−0.0032 (19)0.0035 (19)0.015 (2)
C440.044 (3)0.035 (3)0.039 (3)−0.002 (2)0.003 (2)0.019 (2)
C450.049 (3)0.038 (3)0.049 (3)−0.014 (2)−0.001 (2)0.022 (2)
C460.047 (3)0.027 (2)0.054 (3)−0.004 (2)0.004 (2)0.021 (2)
C3310.048 (3)0.025 (2)0.041 (3)0.000 (2)0.002 (2)0.012 (2)
C4310.041 (3)0.028 (2)0.033 (3)−0.002 (2)0.002 (2)0.010 (2)

Geometric parameters (Å, °)

S1—C111.782 (4)S3—C311.773 (5)
S1—S22.0218 (16)S3—S42.0133 (16)
S2—C211.766 (5)S4—C411.770 (4)
N1—O141.204 (5)N3—O331.205 (4)
N1—O131.211 (5)N3—O341.235 (4)
N1—C141.467 (5)N3—C341.461 (5)
N2—O231.211 (4)N4—O431.231 (4)
N2—O241.233 (4)N4—O441.235 (5)
N2—C241.457 (5)N4—C441.433 (5)
O11—C1311.274 (5)O31—C3311.302 (5)
O11—H1A0.8200O31—H3A0.8200
O12—C1311.256 (5)O32—C3311.238 (5)
O21—C2311.263 (5)O41—C4311.303 (5)
O21—H2A0.8200O41—H4A0.8200
O22—C2311.245 (5)O42—C4311.216 (5)
C11—C161.387 (6)C31—C361.388 (6)
C11—C121.391 (5)C31—C321.393 (5)
C12—C131.390 (5)C32—C331.393 (6)
C12—H120.9300C32—H320.9300
C13—C141.386 (6)C33—C341.400 (6)
C13—C1311.489 (6)C33—C3311.480 (5)
C14—C151.379 (5)C34—C351.359 (5)
C15—C161.374 (5)C35—C361.388 (6)
C15—H150.9300C35—H350.9300
C16—H160.9300C36—H360.9300
C21—C221.400 (5)C41—C421.385 (5)
C21—C261.409 (6)C41—C461.394 (6)
C22—C231.386 (6)C42—C431.374 (6)
C22—H220.9300C42—H420.9300
C23—C241.386 (6)C43—C441.403 (5)
C23—C2311.496 (5)C43—C4311.498 (5)
C24—C251.378 (5)C44—C451.388 (6)
C25—C261.366 (6)C45—C461.390 (6)
C25—H250.9300C45—H450.9300
C26—H260.9300C46—H460.9300
C11—S1—S2106.97 (15)C31—S3—S4105.94 (15)
C21—S2—S1105.54 (15)C41—S4—S3106.38 (14)
O14—N1—O13123.9 (4)O33—N3—O34123.4 (4)
O14—N1—C14119.1 (4)O33—N3—C34119.0 (4)
O13—N1—C14116.9 (4)O34—N3—C34117.5 (4)
O23—N2—O24123.8 (4)O43—N4—O44122.6 (4)
O23—N2—C24118.8 (4)O43—N4—C44118.9 (4)
O24—N2—C24117.4 (4)O44—N4—C44118.5 (4)
C131—O11—H1A109.5C331—O31—H3A109.5
C231—O21—H2A109.5C431—O41—H4A109.5
C16—C11—C12120.1 (4)C36—C31—C32120.0 (4)
C16—C11—S1124.8 (3)C36—C31—S3125.5 (3)
C12—C11—S1115.1 (3)C32—C31—S3114.6 (4)
C13—C12—C11120.8 (4)C31—C32—C33120.1 (4)
C13—C12—H12119.6C31—C32—H32119.9
C11—C12—H12119.6C33—C32—H32119.9
C14—C13—C12117.9 (4)C32—C33—C34118.2 (4)
C14—C13—C131124.9 (4)C32—C33—C331119.6 (4)
C12—C13—C131117.1 (4)C34—C33—C331122.3 (4)
C15—C14—C13121.3 (4)C35—C34—C33122.1 (4)
C15—C14—N1116.8 (4)C35—C34—N3117.4 (4)
C13—C14—N1121.8 (4)C33—C34—N3120.4 (4)
C16—C15—C14120.5 (4)C34—C35—C36119.4 (4)
C16—C15—H15119.8C34—C35—H35120.3
C14—C15—H15119.8C36—C35—H35120.3
C15—C16—C11119.3 (4)C35—C36—C31120.2 (4)
C15—C16—H16120.4C35—C36—H36119.9
C11—C16—H16120.4C31—C36—H36119.9
C22—C21—C26118.9 (4)C42—C41—C46120.1 (4)
C22—C21—S2116.9 (3)C42—C41—S4115.9 (3)
C26—C21—S2124.1 (3)C46—C41—S4124.0 (3)
C23—C22—C21120.8 (4)C43—C42—C41121.5 (4)
C23—C22—H22119.6C43—C42—H42119.2
C21—C22—H22119.6C41—C42—H42119.2
C24—C23—C22118.0 (4)C42—C43—C44117.8 (4)
C24—C23—C231122.4 (4)C42—C43—C431118.4 (3)
C22—C23—C231119.1 (4)C44—C43—C431123.7 (4)
C25—C24—C23122.5 (4)C45—C44—C43121.9 (4)
C25—C24—N2117.7 (4)C45—C44—N4118.3 (4)
C23—C24—N2119.7 (4)C43—C44—N4119.6 (4)
C26—C25—C24119.2 (4)C44—C45—C46119.0 (4)
C26—C25—H25120.4C44—C45—H45120.5
C24—C25—H25120.4C46—C45—H45120.5
C25—C26—C21120.6 (4)C45—C46—C41119.7 (4)
C25—C26—H26119.7C45—C46—H46120.2
C21—C26—H26119.7C41—C46—H46120.2
O12—C131—O11124.3 (4)O32—C331—O31124.1 (4)
O12—C131—C13119.0 (3)O32—C331—C33121.2 (5)
O11—C131—C13116.6 (4)O31—C331—C33114.6 (4)
O22—C231—O21125.0 (4)O42—C431—O41125.6 (4)
O22—C231—C23117.6 (3)O42—C431—C43121.3 (4)
O21—C231—C23117.2 (4)O41—C431—C43113.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O11—H1A···O22i0.821.832.635 (4)166
O21—H2A···O12ii0.821.882.688 (4)169
O31—H3A···O42i0.821.852.666 (4)171
O41—H4A···O32ii0.821.832.618 (4)160

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2385).

References

  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Gudbjarlson, H., Poirier, K. M. & Zaworotko, M. J. (1991). J. Am. Chem. Soc.121, 2599–2600.
  • Li, H., Zhu, G. S., Guo, X. D., Sun, F. X., Ren, H. & Qiu, S. L. (2006). Eur. J. Inorg. Chem. pp. 4123–4128.
  • Luo, F., Zheng, J. M. & Batten, S. R. (2007). Chem. Commun pp. 3744–3746. [PubMed]
  • Shefter, E. & Kalman, T. I. (1969). J. Chem. Soc. D, p. 1027.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Ye, B. H., Tong, M. L. & Chen, X. M. (2005). Coord. Chem. Rev.249, 545–565.

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