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In the crystal structure of the title compound, C16H10N2O8·2H2O, the centrosymmetric organic mol­ecules and water mol­ecules inter­act by way of O—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705163X/hb2593sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680705163X/hb2593Isup2.hkl
Contains datablock I

CCDC reference: 632690

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.061
  • wR factor = 0.194
  • Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level B DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00 _refine_diff_density_max given = 1.065 Test value = 0.800 PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.65 PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 1.07 e/A   
Alert level C DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.38 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 5
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In an attempt to prepare a Zn-containing coordination polymer (Carlucci et al., 2000), the title compound, (I), arose as an unexpected product.

The complete organic molecule (Fig. 1) is generated by inversion at the mid-point of the central N=N bond and a water molecule of crystallization completes the structure. The components interact by way of O—H···O hydrogen bonds to generate a two-dimesnional supramolecular architecture (Table 2).

Related literature top

For background, see: Carlucci et al. (2000).

Experimental top

4,4'-Azo-diphthalic acid (0.035 g, 0.16 mmol), NaOH (0.048 g, 0.12 mmol) and ZnSO4 (0.0028 g, 0.014 mmol) were added to a mixed solvent of ethanol and acetonitrile. The mixture was heated for five hours under reflux with stirring. The resulting liquid was then filtered to give a solution which was infiltrated by diethyl ether in a closed vessel. After a week, colourless blocks of (I) were recovered.

Refinement top

The C-bound and carboxylic acid H atoms were placed in calculated positions [C—H = 0.93 Å, O—H = 0.89 Å] and refined using a riding model, with Uiso(H) = 1.2Ueq(carrier). The water H atoms were found in a dffierent map and refined with O—H = 0.84 (2) Å and Uiso(H) = 1.5Ueq(O). The maximum difference peak is located on the N=N bond, 1.07 Å from N1.

Structure description top

In an attempt to prepare a Zn-containing coordination polymer (Carlucci et al., 2000), the title compound, (I), arose as an unexpected product.

The complete organic molecule (Fig. 1) is generated by inversion at the mid-point of the central N=N bond and a water molecule of crystallization completes the structure. The components interact by way of O—H···O hydrogen bonds to generate a two-dimesnional supramolecular architecture (Table 2).

For background, see: Carlucci et al. (2000).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (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: SHELXTL (Bruker, 2004); software used to prepare material for publication: SHELXTL (Bruker, 2004).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids (arbitaray spheres for the H atoms). Symmetry code: (i) 1 - x, 1 - y, 1 - z.
4,4'-Diazenediyldiphthalic acid dihydrate top
Crystal data top
C16H10N2O8·2H2OZ = 1
Mr = 394.29F(000) = 204
Triclinic, P1Dx = 1.521 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.484 (2) ÅCell parameters from 1533 reflections
b = 6.491 (3) Åθ = 1.6–25.2°
c = 12.820 (5) ŵ = 0.13 mm1
α = 86.779 (6)°T = 298 K
β = 82.921 (5)°Block, colourless
γ = 71.956 (6)°0.28 × 0.24 × 0.19 mm
V = 430.5 (3) Å3
Data collection top
Bruker APEXII CCD
diffractometer
1533 independent reflections
Radiation source: fine-focus sealed tube1378 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.012
Detector resolution: 0 pixels mm-1θmax = 25.2°, θmin = 1.6°
ω scansh = 66
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
k = 47
Tmin = 0.965, Tmax = 0.976l = 1515
2278 measured reflections
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.1258P)2 + 0.1677P]
where P = (Fo2 + 2Fc2)/3
1533 reflections(Δ/σ)max < 0.001
135 parametersΔρmax = 1.07 e Å3
5 restraintsΔρmin = 0.23 e Å3
Crystal data top
C16H10N2O8·2H2Oγ = 71.956 (6)°
Mr = 394.29V = 430.5 (3) Å3
Triclinic, P1Z = 1
a = 5.484 (2) ÅMo Kα radiation
b = 6.491 (3) ŵ = 0.13 mm1
c = 12.820 (5) ÅT = 298 K
α = 86.779 (6)°0.28 × 0.24 × 0.19 mm
β = 82.921 (5)°
Data collection top
Bruker APEXII CCD
diffractometer
1533 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
1378 reflections with I > 2σ(I)
Tmin = 0.965, Tmax = 0.976Rint = 0.012
2278 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0615 restraints
wR(F2) = 0.194H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 1.07 e Å3
1533 reflectionsΔρmin = 0.23 e Å3
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
O20.2911 (4)0.1176 (3)0.13083 (13)0.0536 (6)
O1W0.8546 (4)0.6214 (3)0.15345 (14)0.0490 (5)
O40.7036 (3)0.1458 (4)0.07814 (13)0.0557 (6)
H4A0.71940.14190.01380.084*
O10.0028 (4)0.1294 (3)0.26625 (14)0.0546 (6)
H10.04480.20310.22610.082*
O30.2965 (4)0.3246 (4)0.05734 (13)0.0579 (6)
C50.4209 (5)0.3623 (4)0.39868 (19)0.0476 (7)
C20.2568 (5)0.0939 (4)0.27905 (18)0.0426 (6)
N10.5149 (5)0.5055 (4)0.45109 (17)0.0566 (7)
C80.4608 (5)0.2336 (4)0.11278 (17)0.0391 (6)
C70.4044 (4)0.2211 (4)0.23069 (17)0.0390 (6)
C60.4860 (5)0.3540 (4)0.29044 (19)0.0450 (6)
H40.58470.43780.25780.054*
C10.1826 (5)0.0600 (4)0.21811 (18)0.0417 (6)
C40.2685 (7)0.2389 (5)0.4474 (2)0.0604 (8)
H30.22050.24640.51960.072*
C30.1906 (6)0.1070 (5)0.3879 (2)0.0577 (8)
H20.09110.02410.42080.069*
H1WA0.748 (5)0.683 (5)0.111 (2)0.087*
H1WB0.981 (5)0.525 (5)0.124 (2)0.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0578 (11)0.0728 (13)0.0361 (10)0.0289 (10)0.0053 (8)0.0230 (9)
O1W0.0522 (11)0.0558 (11)0.0423 (10)0.0195 (8)0.0075 (8)0.0064 (8)
O40.0476 (11)0.0861 (14)0.0287 (9)0.0145 (9)0.0008 (8)0.0083 (9)
O10.0639 (12)0.0696 (13)0.0405 (10)0.0368 (10)0.0040 (8)0.0129 (9)
O30.0552 (11)0.0787 (14)0.0293 (9)0.0048 (10)0.0052 (8)0.0039 (9)
C50.0587 (15)0.0555 (15)0.0333 (13)0.0220 (12)0.0058 (11)0.0109 (11)
C20.0483 (13)0.0531 (14)0.0279 (12)0.0178 (11)0.0012 (10)0.0073 (10)
N10.0789 (16)0.0662 (15)0.0329 (10)0.0319 (13)0.0078 (10)0.0109 (10)
C80.0463 (13)0.0451 (12)0.0276 (11)0.0167 (10)0.0006 (9)0.0075 (9)
C70.0422 (12)0.0474 (13)0.0266 (11)0.0117 (10)0.0031 (9)0.0063 (9)
C60.0544 (14)0.0510 (14)0.0340 (13)0.0222 (11)0.0040 (10)0.0060 (10)
C10.0438 (13)0.0501 (13)0.0322 (12)0.0154 (10)0.0028 (9)0.0068 (10)
C40.087 (2)0.0779 (19)0.0247 (12)0.0397 (17)0.0024 (12)0.0093 (12)
C30.0796 (19)0.0784 (19)0.0286 (13)0.0466 (16)0.0051 (12)0.0093 (12)
Geometric parameters (Å, º) top
O2—C11.221 (3)C2—C71.398 (3)
O1W—H1WA0.84 (3)C2—C31.399 (3)
O1W—H1WB0.84 (3)C2—C11.481 (3)
O4—C81.307 (3)N1—N1i1.245 (4)
O4—H4A0.8200C8—C71.508 (3)
O1—C11.310 (3)C7—C61.389 (3)
O1—H10.8200C6—H40.9300
O3—C81.203 (3)C4—C31.370 (4)
C5—C61.389 (4)C4—H30.9300
C5—C41.400 (4)C3—H20.9300
C5—N11.426 (4)
H1WA—O1W—H1WB111.0 (17)C6—C7—C8117.9 (2)
C8—O4—H4A109.5C2—C7—C8121.7 (2)
C1—O1—H1109.5C7—C6—C5120.3 (2)
C6—C5—C4119.8 (2)C7—C6—H4119.8
C6—C5—N1115.0 (2)C5—C6—H4119.8
C4—C5—N1125.2 (2)O2—C1—O1123.9 (2)
C7—C2—C3118.5 (2)O2—C1—C2121.5 (2)
C7—C2—C1121.2 (2)O1—C1—C2114.5 (2)
C3—C2—C1120.2 (2)C3—C4—C5119.5 (2)
N1i—N1—C5115.4 (3)C3—C4—H3120.3
O3—C8—O4123.9 (2)C5—C4—H3120.3
O3—C8—C7122.2 (2)C4—C3—C2121.7 (3)
O4—C8—C7113.8 (2)C4—C3—H2119.1
C6—C7—C2120.2 (2)C2—C3—H2119.1
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WB···O3ii0.84 (3)1.95 (3)2.782 (3)173 (4)
O1W—H1WA···O2iii0.84 (3)2.43 (2)3.070 (3)134 (3)
O1W—H1WA···O3iv0.84 (3)2.20 (2)2.895 (3)139 (3)
O1—H1···O1Wv0.821.762.577 (2)173
O4—H4A···O2vi0.821.882.692 (2)171
Symmetry codes: (ii) x+1, y, z; (iii) x, y+1, z; (iv) x+1, y+1, z; (v) x1, y1, z; (vi) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC16H10N2O8·2H2O
Mr394.29
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)5.484 (2), 6.491 (3), 12.820 (5)
α, β, γ (°)86.779 (6), 82.921 (5), 71.956 (6)
V3)430.5 (3)
Z1
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.28 × 0.24 × 0.19
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.965, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
2278, 1533, 1378
Rint0.012
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.194, 1.10
No. of reflections1533
No. of parameters135
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.07, 0.23

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2004).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WB···O3i0.84 (3)1.95 (3)2.782 (3)173 (4)
O1W—H1WA···O2ii0.84 (3)2.43 (2)3.070 (3)134 (3)
O1W—H1WA···O3iii0.84 (3)2.20 (2)2.895 (3)139 (3)
O1—H1···O1Wiv0.821.762.577 (2)173.0
O4—H4A···O2v0.821.882.692 (2)170.8
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) x1, y1, z; (v) x+1, y, z.
 

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