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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o162.
Published online 2007 December 6. doi:  10.1107/S1600536807064112
PMCID: PMC2915230

3,3′-Diazenediyldiphthalic acid dihydrate

Abstract

In the crystal structure of the title compound, C16H10N2O8·2H2O, the organic mol­ecule is located on a centre of symmetry. The two benzene rings are parallel, but not coplanar, as indicated by N=N—C—C torsion angles involving the azo group of 12.1 (5) and −168.2 (3)°. The organic mol­ecule and the water mol­ecule are linked by O—H(...)O hydrogen bonds, forming a three-dimensional network.

Related literature

For related literature, see: Carlucci et al. (2000 [triangle]).

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Object name is e-64-0o162-scheme1.jpg

Experimental

Crystal data

  • C16H10N2O8·2H2O
  • M r = 394.29
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o162-efi1.jpg
  • a = 6.6914 (14) Å
  • b = 7.8566 (17) Å
  • c = 8.7665 (19) Å
  • α = 95.658 (3)°
  • β = 100.628 (3)°
  • γ = 105.601 (3)°
  • V = 430.90 (16) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.13 mm−1
  • T = 298 (2) K
  • 0.27 × 0.19 × 0.15 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.966, T max = 0.981
  • 2297 measured reflections
  • 1530 independent reflections
  • 1248 reflections with I > 2σ(I)
  • R int = 0.009

Refinement

  • R[F 2 > 2σ(F 2)] = 0.084
  • wR(F 2) = 0.260
  • S = 1.11
  • 1530 reflections
  • 135 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.04 e Å−3
  • Δρmin = −0.19 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, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [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/S1600536807064112/is2247sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064112/is2247Isup2.hkl

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

Acknowledgments

The authors are grateful to SiChuan University for financial support.

supplementary crystallographic information

Comment

In an attempt to prepare a Cd-containing coordination polmyer (Carlucci et al., 2000), the title compound was obtained as an unexpected product.

The complete organic molecule (Fig. 1) is generated by inversion at the midpoint of the central N—N bond and a water molecule of crystallization completes the crystal structure. The components interact through O—H···O hydrogen bonds (Table 1) to generate a three-dimensional architecture.

Experimental

CdSO4 (0.033 g, 0.012 mmol), 2,2',3,3'-diazenediyldiphthalic acid (0.026 g, 0.014 mmol) and NaOH (0.048 mmol, 0.12 mmol), were added in a mixed solvent of acetonitrile and the mixture was heated for ten hours under reflux. During the process stirring and influx were required. The resultant was then filtered to give a pure solution which was infiltrated by diethyl ether freely in a closed vessel. Single crystals suitable for X-ray diffraction were obtained for a week.

Refinement

C-bound H atoms were placed at calculated positions (C—H = 0.93 Å) and were treated as riding, with Uiso(H) = 1.2Ueq(C). Carboxy H atoms were constrained with O—H = 0.82 Å and Uiso(H) = 1.2Ueq(O), but each O—H group was allowed to rotate freely about its C—O bond. Water H atoms were tentatively located in a difference Fourier map and were refined, with distance restraints of O–H = 0.85 (1) Å and H···H = 1.39 (1) Å, and with Uiso(H) = 1.2Ueq(O). The maximum residual peak is located 1.34 Å from Br1.

Figures

Fig. 1.
The molecular structure of (I), showing the atomic numbering scheme. Non-H atoms are shown as 30% probability displacement ellipsoids. [symmetry code: (i) 1 - x, 1 - y, 1 - z]

Crystal data

C16H10N2O8·2H2OZ = 1
Mr = 394.29F000 = 204
Triclinic, P1Dx = 1.519 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 6.6914 (14) ÅCell parameters from 1248 reflections
b = 7.8566 (17) Åθ = 2.4–25.2º
c = 8.7665 (19) ŵ = 0.13 mm1
α = 95.658 (3)ºT = 298 (2) K
β = 100.628 (3)ºBlock, colourless
γ = 105.601 (3)º0.27 × 0.19 × 0.15 mm
V = 430.90 (16) Å3

Data collection

Bruker APEXII area-detector diffractometer1530 independent reflections
Radiation source: fine-focus sealed tube1248 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.009
T = 298(2) Kθmax = 25.2º
[var phi] and ω scanθmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)h = −7→8
Tmin = 0.966, Tmax = 0.981k = −6→9
2297 measured reflectionsl = −10→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.084H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.260  w = 1/[σ2(Fo2) + (0.16P)2 + 0.1722P] where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
1530 reflectionsΔρmax = 1.04 e Å3
135 parametersΔρmin = −0.19 e Å3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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
C10.1413 (5)0.2366 (4)0.1954 (4)0.0537 (8)
C20.0818 (5)0.2502 (4)0.3535 (3)0.0505 (8)
C3−0.1122 (5)0.1482 (4)0.3774 (4)0.0541 (8)
C4−0.2663 (5)0.0169 (4)0.2462 (4)0.0558 (8)
C5−0.1571 (6)0.1709 (5)0.5259 (4)0.0688 (10)
H5−0.28670.10420.54250.083*
C6−0.0133 (7)0.2900 (6)0.6479 (4)0.0775 (11)
H6−0.04720.30460.74570.093*
C70.1814 (7)0.3884 (5)0.6264 (4)0.0741 (11)
H70.27920.46810.70950.089*
C80.2295 (5)0.3672 (4)0.4798 (4)0.0585 (9)
N10.4269 (5)0.4597 (4)0.4434 (3)0.0664 (9)
O10.1017 (4)0.3301 (3)0.1000 (3)0.0728 (8)
O20.2414 (5)0.1183 (4)0.1782 (3)0.0797 (9)
H20.29130.12850.09970.120*
O3−0.2418 (5)0.0128 (4)0.1130 (3)0.0933 (11)
O4−0.4243 (4)−0.0911 (4)0.2846 (3)0.0759 (8)
H4−0.4939−0.16580.20800.114*
O1W0.3401 (5)0.6712 (4)0.0411 (4)0.0934 (10)
H1WA0.306 (7)0.563 (3)0.057 (8)0.140*
H1WB0.228 (5)0.705 (6)0.025 (8)0.140*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0446 (15)0.0528 (17)0.0533 (17)0.0005 (13)0.0063 (12)0.0074 (14)
C20.0540 (16)0.0461 (15)0.0499 (16)0.0139 (13)0.0078 (13)0.0087 (12)
C30.0584 (18)0.0510 (17)0.0584 (18)0.0205 (14)0.0168 (14)0.0137 (13)
C40.0509 (17)0.0527 (17)0.0627 (19)0.0066 (14)0.0185 (14)0.0165 (14)
C50.078 (2)0.075 (2)0.070 (2)0.0326 (19)0.0336 (18)0.0233 (18)
C60.101 (3)0.085 (3)0.056 (2)0.038 (2)0.028 (2)0.0067 (18)
C70.096 (3)0.070 (2)0.0527 (19)0.031 (2)0.0049 (17)−0.0023 (16)
C80.0645 (19)0.0506 (17)0.0566 (18)0.0164 (15)0.0064 (14)0.0045 (13)
N10.0659 (18)0.0644 (17)0.0545 (16)0.0066 (14)0.0004 (12)0.0012 (12)
O10.0810 (17)0.0723 (16)0.0667 (15)0.0140 (13)0.0225 (12)0.0301 (13)
O20.100 (2)0.100 (2)0.0593 (15)0.0501 (17)0.0301 (13)0.0201 (13)
O30.0813 (18)0.093 (2)0.0686 (18)−0.0311 (15)0.0182 (13)−0.0046 (14)
O40.0589 (15)0.0733 (17)0.0910 (19)0.0041 (12)0.0260 (13)0.0159 (13)
O1W0.0775 (19)0.0712 (18)0.116 (2)0.0007 (14)0.0076 (17)0.0286 (17)

Geometric parameters (Å, °)

C1—O11.205 (4)C6—C71.381 (5)
C1—O21.296 (4)C6—H60.9300
C1—C21.513 (4)C7—C81.387 (5)
C2—C31.395 (4)C7—H70.9300
C2—C81.398 (4)C8—N11.435 (5)
C3—C51.394 (5)N1—N1i1.236 (5)
C3—C41.486 (5)O2—H20.8200
C4—O31.207 (4)O4—H40.8200
C4—O41.287 (4)O1W—H1WA0.85 (3)
C5—C61.373 (6)O1W—H1WB0.85 (4)
C5—H50.9300
O1—C1—O2125.3 (3)C3—C5—H5119.4
O1—C1—C2122.3 (3)C5—C6—C7120.4 (3)
O2—C1—C2112.4 (3)C5—C6—H6119.8
C3—C2—C8119.5 (3)C7—C6—H6119.8
C3—C2—C1122.3 (3)C6—C7—C8119.4 (3)
C8—C2—C1118.2 (3)C6—C7—H7120.3
C5—C3—C2118.9 (3)C8—C7—H7120.3
C5—C3—C4121.1 (3)C7—C8—C2120.7 (3)
C2—C3—C4120.0 (3)C7—C8—N1124.6 (3)
O3—C4—O4123.0 (3)C2—C8—N1114.7 (3)
O3—C4—C3121.4 (3)N1i—N1—C8116.2 (4)
O4—C4—C3115.6 (3)C1—O2—H2109.5
C6—C5—C3121.1 (3)C4—O4—H4109.5
C6—C5—H5119.4H1WA—O1W—H1WB109 (5)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O10.85 (3)2.08 (2)2.875 (4)155 (4)
O4—H4···O1Wii0.821.812.631 (4)177
O1W—H1WB···O3iii0.85 (4)2.62 (4)3.104 (5)117 (4)
O2—H2···O3iv0.822.002.657 (4)137

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2247).

References

  • Bruker (2004). APEX2 (Version 1.0-27) and SAINT (Version 6.36A). Bruker AXS Inc., Madison, Winconsin, USA.
  • Carlucci, L., Ciani, G., Proserpion, G. M. & Rizzato, S. (2000). Angew. Chem. Int. Ed.39, 1506–1510. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.
  • Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography