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In the title compound, C5H4N2O4·H2O, the 3,5-pyrazoledicarboxylic acid (H3pdc) molecules are joined into one-dimensional chains by O—H...O and N—H...O hydrogen bonds, with distances of 2.671 (2) and 2.776 (2) Å, respectively. The one-dimensional chains form a three-dimensional structure via O—H...OW and OW—HW...N hydrogen bonds, with distances of 2.597 (3) and 2.780 (3) Å, respectively. In addition to the potential for forming open-channel frameworks, access to the six coordination atoms of H3pdc can be directly controlled by varying the pH of the reaction environment, allowing further control over the design and synthesis of novel coordination polymers using various metal centers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007484/bk1520sup1.cif
Contains datablocks global, H3pdc

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007484/bk1520H3pdcsup2.hkl
Contains datablock H3pdc

CCDC reference: 150844

Computing details top

Data collection: CAD-4-PC (Enraf-Nonius, 1992); cell refinement: CAD-4-PC; data reduction: XCAD4/PC (Harms, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SCHAKAL92; software used to prepare material for publication: CIF.

3,5-pyrazoledicarboxylic acid monohydrate top
Crystal data top
C5H4N2O4·H2OF(000) = 360
Mr = 174.12Dx = 1.641 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.386 (3) ÅCell parameters from 20 reflections
b = 3.750 (1) Åθ = 7.1–12.1°
c = 14.350 (3) ŵ = 0.15 mm1
β = 101.88 (3)°T = 293 K
V = 704.9 (3) Å3Columnar, colorless
Z = 40.30 × 0.10 × 0.08 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
856 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
Graphite monochromatorθmax = 26.0°, θmin = 2.3°
ω scansh = 016
Absorption correction: ψ scan
(Kopfman & Hubber, 1968)
k = 44
Tmin = 0.959, Tmax = 1.000l = 1717
2883 measured reflections3 standard reflections every 250 min
1388 independent reflections intensity decay: 2.8%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079Calculated w = 1/[σ2(Fo2) + 0.250P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max < 0.001
1388 reflectionsΔρmax = 0.17 e Å3
128 parametersΔρmin = 0.23 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0109 (12)
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
O10.04455 (12)0.2049 (6)0.41802 (10)0.0640 (6)
O20.10649 (12)0.0709 (6)0.39626 (11)0.0613 (6)
H10.0840 (17)0.114 (8)0.4625 (18)0.074*
O30.11526 (11)0.2663 (5)0.05303 (10)0.0558 (6)
O40.24032 (12)0.0402 (6)0.00896 (11)0.0553 (5)
H20.2596 (17)0.077 (8)0.0766 (17)0.066*
O50.29513 (15)0.1326 (7)0.19175 (14)0.0753 (7)
H30.360 (2)0.065 (9)0.212 (2)0.090*
H40.284 (2)0.318 (8)0.218 (2)0.090*
N10.01692 (13)0.3323 (6)0.22830 (11)0.0443 (5)
N20.01893 (13)0.3347 (6)0.13467 (12)0.0424 (5)
H50.0195 (16)0.434 (7)0.0970 (15)0.051*
C10.03493 (18)0.1021 (7)0.36728 (15)0.0459 (6)
C20.05516 (16)0.1631 (7)0.26339 (14)0.0395 (6)
C30.13674 (17)0.0613 (7)0.19199 (15)0.0405 (6)
H60.1937 (15)0.071 (7)0.1979 (15)0.049*
C40.11019 (15)0.1748 (7)0.10941 (14)0.0383 (6)
C50.15587 (16)0.1420 (7)0.00769 (14)0.0409 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0621 (11)0.0937 (16)0.0326 (9)0.0169 (12)0.0016 (8)0.0089 (10)
O20.0631 (11)0.0884 (15)0.0329 (8)0.0157 (12)0.0108 (8)0.0113 (10)
O30.0559 (9)0.0819 (15)0.0302 (8)0.0125 (10)0.0101 (8)0.0047 (9)
O40.0504 (9)0.0793 (14)0.0339 (8)0.0134 (10)0.0035 (7)0.0004 (10)
O50.0548 (11)0.1051 (19)0.0570 (12)0.0109 (14)0.0096 (9)0.0227 (13)
N10.0481 (10)0.0581 (14)0.0258 (9)0.0007 (11)0.0055 (8)0.0033 (10)
N20.0453 (11)0.0573 (14)0.0256 (9)0.0000 (11)0.0092 (8)0.0058 (10)
C10.0504 (13)0.0543 (17)0.0333 (12)0.0009 (14)0.0096 (11)0.0032 (13)
C20.0463 (12)0.0433 (14)0.0299 (10)0.0035 (12)0.0102 (10)0.0045 (11)
C30.0430 (12)0.0458 (16)0.0331 (11)0.0014 (12)0.0087 (10)0.0028 (11)
C40.0400 (11)0.0413 (14)0.0330 (11)0.0034 (12)0.0062 (9)0.0008 (11)
C50.0414 (12)0.0482 (15)0.0322 (11)0.0055 (13)0.0052 (10)0.0024 (12)
Geometric parameters (Å, º) top
O1—C11.221 (3)N1—C21.337 (3)
O2—C11.294 (3)N2—C41.342 (3)
O2—H10.95 (3)N2—H50.90 (2)
O3—C51.211 (2)C1—C21.477 (3)
O4—C51.300 (3)C2—C31.388 (3)
O4—H20.96 (2)C3—C41.373 (3)
O5—H30.90 (3)C3—H60.93 (2)
O5—H40.82 (3)C4—C51.467 (3)
N1—N21.330 (2)
C1—O2—H1107.7 (15)N1—C2—C1117.2 (2)
C5—O4—H2107.7 (14)C3—C2—C1130.9 (2)
H3—O5—H4111 (3)C4—C3—C2104.3 (2)
N2—N1—C2104.20 (18)C4—C3—H6127.5 (13)
N1—N2—C4112.88 (18)C2—C3—H6128.0 (13)
N1—N2—H5118.6 (14)N2—C4—C3106.77 (19)
C4—N2—H5128.5 (14)N2—C4—C5118.43 (18)
O1—C1—O2125.3 (2)C3—C4—C5134.7 (2)
O1—C1—C2120.6 (2)O3—C5—O4124.9 (2)
O2—C1—C2114.1 (2)O3—C5—C4121.8 (2)
N1—C2—C3111.82 (18)O4—C5—C4113.30 (19)
C2—N1—N2—C40.0 (3)N1—N2—C4—C30.4 (3)
N2—N1—C2—C30.5 (3)N1—N2—C4—C5176.8 (2)
N2—N1—C2—C1177.2 (2)C2—C3—C4—N20.7 (3)
O1—C1—C2—N10.3 (4)C2—C3—C4—C5175.9 (3)
O2—C1—C2—N1178.3 (2)N2—C4—C5—O32.8 (4)
O1—C1—C2—C3177.4 (3)C3—C4—C5—O3179.0 (3)
O2—C1—C2—C31.2 (4)N2—C4—C5—O4175.1 (2)
N1—C2—C3—C40.7 (3)C3—C4—C5—O41.1 (4)
C1—C2—C3—C4176.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O1i0.95 (3)1.72 (3)2.671 (2)178 (3)
O4—H2···O50.96 (2)1.64 (2)2.597 (3)178 (2)
O5—H3···N1ii0.90 (3)1.90 (3)2.780 (3)165 (3)
O5—H4···O5iii0.82 (3)2.18 (3)2.933 (3)153 (3)
N2—H5···O3iv0.90 (2)1.91 (2)2.776 (2)162 (2)
Symmetry codes: (i) x, y, z+1; (ii) x1/2, y+1/2, z1/2; (iii) x1/2, y1/2, z1/2; (iv) x, y+1, z.
 

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