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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o162
https://doi.org/10.1107/S1600536807064112

3,3′-Diazenediyldiphthalic acid dihydrate

Bin Yang,a Jun Wang,a,b Yang Hou,a Bao-zhong Zhaoa* and Qiang Fua

aCollege of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China, and bDepartment of Chemistry, SiChuan University of Science and Engineering, Zigong 643000, People's Republic of China
*Correspondence e-mail: lulusczg@126.com

(Received 13 November 2007; accepted 28 November 2007; online 6 December 2007)

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[Carlucci, L., Ciani, G., Proserpion, G. M. & Rizzato, S. (2000). Angew. Chem. Int. Ed. 39, 1506-1510.]).

[Scheme 1]

Experimental

Crystal data

  • C16H10N2O8·2H2O

  • Mr = 394.29

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.966, Tmax = 0.981

  • 2297 measured reflections

  • 1530 independent reflections

  • 1248 reflections with I > 2σ(I)

  • Rint = 0.009
Refinement

  • R[F2 > 2σ(F2)] = 0.084

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1W—H1WA⋯O1 0.85 (3) 2.08 (2) 2.875 (4) 155 (4)
O4—H4⋯O1Wi 0.82 1.81 2.631 (4) 177
O1W—H1WB⋯O3ii 0.85 (4) 2.62 (4) 3.104 (5) 117 (4)
O2—H2⋯O3iii 0.82 2.00 2.657 (4) 137
Symmetry codes: (i) x-1, y-1, z; (ii) -x, -y+1, -z; (iii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 (Version 1.0-27) and SAINT (Version 6.36A). Bruker AXS Inc., Madison, Winconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004[Bruker (2004). APEX2 (Version 1.0-27) and SAINT (Version 6.36A). Bruker AXS Inc., Madison, Winconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807064112/is2247sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064112/is2247Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Structure description top

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.

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

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] 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]
3,3'-Diazenediyldiphthalic acid dihydrate top
Crystal data top
C16H10N2O8·2H2OZ = 1
Mr = 394.29F(000) = 204
Triclinic, P1Dx = 1.519 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.6914 (14) ÅCell parameters from 1248 reflections
b = 7.8566 (17) Åθ = 2.4–25.2°
c = 8.7665 (19) ŵ = 0.13 mm−1
α = 95.658 (3)°T = 298 K
β = 100.628 (3)°Block, colourless
γ = 105.601 (3)°0.27 × 0.19 × 0.15 mm
V = 430.90 (16) Å3
Data collection top
Bruker APEXII area-detector
diffractometer		1530 independent reflections
Radiation source: fine-focus sealed tube1248 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.009
φ and ω scanθmax = 25.2°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −7→8
Tmin = 0.966, Tmax = 0.981k = −6→9
2297 measured reflectionsl = −10→10
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.084Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.260H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.16P)2 + 0.1722P]
where P = (Fo2 + 2Fc2)/3
1530 reflections(Δ/σ)max < 0.001
135 parametersΔρmax = 1.04 e Å−3
3 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C16H10N2O8·2H2Oγ = 105.601 (3)°
Mr = 394.29V = 430.90 (16) Å3
Triclinic, P1Z = 1
a = 6.6914 (14) ÅMo Kα radiation
b = 7.8566 (17) ŵ = 0.13 mm−1
c = 8.7665 (19) ÅT = 298 K
α = 95.658 (3)°0.27 × 0.19 × 0.15 mm
β = 100.628 (3)°
Data collection top
Bruker APEXII area-detector
diffractometer		1530 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		1248 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.981Rint = 0.009
2297 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0843 restraints
wR(F2) = 0.260H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 1.04 e Å−3
1530 reflectionsΔρmin = −0.19 e Å−3
135 parameters
Special details top

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) top
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) top
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, º) top
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 code: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
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.

Experimental details

Crystal data
Chemical formulaC16H10N2O8·2H2O
Mr394.29
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)6.6914 (14), 7.8566 (17), 8.7665 (19)
α, β, γ (°)95.658 (3), 100.628 (3), 105.601 (3)
V (Å3)430.90 (16)
Z1
Radiation typeMo Kα
µ (mm−1)0.13
Crystal size (mm)0.27 × 0.19 × 0.15
Data collection
DiffractometerBruker APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.966, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections		2297, 1530, 1248
Rint0.009
(sin θ/λ)max (Å−1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.084, 0.260, 1.11
No. of reflections1530
No. of parameters135
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)1.04, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O10.85 (3)2.08 (2)2.875 (4)155 (4)
O4—H4···O1Wi0.821.812.631 (4)177
O1W—H1WB···O3ii0.85 (4)2.62 (4)3.104 (5)117 (4)
O2—H2···O3iii0.822.002.657 (4)137
Symmetry codes: (i) x−1, y−1, z; (ii) −x, −y+1, −z; (iii) −x, −y, −z.
 

Acknowledgements

The authors are grateful to SiChuan University for financial support.

References

First citationBruker (2004). APEX2 (Version 1.0-27) and SAINT (Version 6.36A). Bruker AXS Inc., Madison, Winconsin, USA.  Google Scholar
 First citationCarlucci, L., Ciani, G., Proserpion, G. M. & Rizzato, S. (2000). Angew. Chem. Int. Ed. 39, 1506–1510.  CrossRef CAS Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 1| January 2008| Page o162
https://doi.org/10.1107/S1600536807064112
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