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The title compound, C4H4N2O4·H2O, is a triclinic polymorphic form of pyridazine-3,6-di­carboxyl­ic acid monohydrate. The dihedral angles between the planes of the carboxyl­ic acid groups and the planar pyrazine ring are 2.0 (2) and 5.6 (2)°. The acid and water mol­ecules form almost planar sheets connected by hydrogen bonds, with O...O distances ranging from 2.5143 (14) to 2.7330 (16) Å and an O...N distance of 2.8234 (18) Å. The shortest distance between two adjacent sheets is 3.2 (1) Å, indicating van der Waals-type interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804027527/lh6293sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804027527/lh6293Isup2.hkl
Contains datablock I

CCDC reference: 259111

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.046
  • wR factor = 0.131
  • Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.86
Author Response: See Experimental

Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 3.24 PLAT417_ALERT_2_C Short Inter D-H..H-D H3 .. H12 .. 2.12 Ang.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: KM-4 Software (Kuma, 1996); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1992); software used to prepare material for publication: SHELXL97.

pyridazine-3,6-dicarboxylic acid monohydrate top
Crystal data top
C6H4N2O4·H2OZ = 2
Mr = 186.13F(000) = 192
Triclinic, P1Dx = 1.655 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9630 (14) ÅCell parameters from 25 reflections
b = 7.2888 (15) Åθ = 6–15°
c = 8.0319 (16) ŵ = 0.15 mm1
α = 80.30 (3)°T = 293 K
β = 77.48 (3)°Rectangular plate, colourless
γ = 70.66 (3)°0.20 × 0.16 × 0.10 mm
V = 373.41 (15) Å3
Data collection top
Kuma KM-4 four-circle
diffractometer
Rint = 0.021
Radiation source: fine-focus sealed tubeθmax = 30.1°, θmin = 3.0°
Graphite monochromatorh = 09
ω/2θ scansk = 910
1854 measured reflectionsl = 1011
1725 independent reflections3 standard reflections every 200 reflections
1533 reflections with I > 2σ(I) intensity decay: 0.8%
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131All H-atom parameters refined
S = 1.05 w = 1/[σ2(Fo2) + (0.1105P)2 + 0.0069P]
where P = (Fo2 + 2Fc2)/3
1725 reflections(Δ/σ)max < 0.001
142 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.25 e Å3
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
O10.21624 (15)0.09472 (13)0.60875 (14)0.0388 (3)
C30.31478 (17)0.16714 (16)0.66251 (15)0.0273 (3)
C60.56819 (17)0.27818 (16)0.79289 (15)0.0286 (3)
O20.03230 (15)0.20904 (14)0.52671 (14)0.0403 (3)
O30.84671 (18)0.18169 (15)0.94120 (15)0.0473 (3)
C70.17517 (16)0.09303 (16)0.59240 (14)0.0277 (3)
N10.59494 (16)0.08834 (15)0.79435 (15)0.0327 (3)
N20.46767 (16)0.03110 (15)0.72830 (15)0.0322 (3)
O100.90041 (17)0.75577 (16)0.91162 (16)0.0499 (3)
C50.4124 (2)0.42484 (17)0.72338 (18)0.0347 (3)
C80.71887 (18)0.33019 (17)0.86972 (16)0.0327 (3)
C40.27941 (19)0.36685 (17)0.65580 (18)0.0343 (3)
O40.7148 (2)0.49816 (17)0.8601 (2)0.0633 (4)
H110.865 (3)0.665 (3)0.902 (3)0.053 (5)*
H30.930 (4)0.205 (4)0.986 (3)0.071 (7)*
H120.812 (3)0.867 (3)0.889 (3)0.053 (5)*
H10.115 (5)0.125 (6)0.567 (4)0.118 (10)*
H40.162 (3)0.453 (3)0.595 (2)0.051 (5)*
H50.408 (4)0.557 (4)0.724 (3)0.071 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0382 (5)0.0261 (4)0.0609 (6)0.0102 (3)0.0275 (4)0.0031 (4)
C30.0258 (5)0.0265 (5)0.0345 (6)0.0082 (4)0.0142 (4)0.0042 (4)
C60.0277 (5)0.0259 (5)0.0373 (6)0.0085 (4)0.0144 (4)0.0048 (4)
O20.0363 (5)0.0317 (5)0.0615 (6)0.0070 (3)0.0309 (4)0.0056 (4)
O30.0529 (6)0.0358 (5)0.0683 (7)0.0153 (4)0.0425 (6)0.0012 (4)
C70.0261 (5)0.0269 (5)0.0344 (6)0.0083 (4)0.0129 (4)0.0046 (4)
N10.0318 (5)0.0261 (5)0.0477 (6)0.0080 (3)0.0230 (4)0.0046 (4)
N20.0310 (5)0.0253 (4)0.0477 (6)0.0079 (4)0.0221 (4)0.0049 (4)
O100.0526 (6)0.0328 (5)0.0807 (8)0.0170 (4)0.0450 (6)0.0014 (5)
C50.0367 (6)0.0229 (5)0.0503 (7)0.0083 (4)0.0217 (5)0.0029 (4)
C80.0310 (6)0.0300 (5)0.0446 (7)0.0111 (4)0.0168 (5)0.0073 (5)
C40.0335 (6)0.0246 (5)0.0487 (7)0.0054 (4)0.0225 (5)0.0021 (4)
O40.0616 (7)0.0318 (5)0.1166 (11)0.0166 (5)0.0530 (7)0.0087 (6)
Geometric parameters (Å, º) top
O1—C71.2916 (14)O3—C81.2914 (16)
O1—H10.94 (4)O3—H30.82 (3)
C3—N21.3281 (15)N1—N21.3283 (14)
C3—C41.3872 (16)O10—H110.80 (2)
C3—C71.4972 (14)O10—H120.86 (2)
C6—N11.3319 (14)C5—C41.3731 (17)
C6—C51.3873 (17)C5—H50.96 (2)
C6—C81.4994 (15)C8—O41.2048 (16)
O2—C71.2260 (14)C4—H41.02 (2)
C7—O1—H1109 (2)C3—N2—N1118.38 (10)
N2—C3—C4124.44 (10)H11—O10—H12113 (2)
N2—C3—C7115.73 (10)C4—C5—C6116.89 (11)
C4—C3—C7119.83 (10)C4—C5—H5125.5 (16)
N1—C6—C5123.42 (10)C6—C5—H5117.6 (16)
N1—C6—C8116.62 (10)O4—C8—O3125.79 (11)
C5—C6—C8119.96 (10)O4—C8—C6120.22 (12)
C8—O3—H3116.4 (18)O3—C8—C6113.99 (10)
O2—C7—O1124.66 (10)C5—C4—C3116.82 (11)
O2—C7—C3119.85 (10)C5—C4—H4127.5 (11)
O1—C7—C3115.48 (10)C3—C4—H4115.6 (11)
N2—N1—C6120.04 (10)
N2—C3—C7—O2178.76 (11)N1—C6—C5—C41.0 (2)
C4—C3—C7—O21.24 (19)C8—C6—C5—C4179.76 (11)
N2—C3—C7—O11.97 (16)N1—C6—C8—O4173.80 (14)
C4—C3—C7—O1178.03 (11)C5—C6—C8—O45.5 (2)
C5—C6—N1—N20.6 (2)N1—C6—C8—O35.52 (17)
C8—C6—N1—N2179.89 (11)C5—C6—C8—O3175.18 (12)
C4—C3—N2—N10.8 (2)C6—C5—C4—C30.5 (2)
C7—C3—N2—N1179.18 (11)N2—C3—C4—C50.4 (2)
C6—N1—N2—C30.29 (19)C7—C3—C4—C5179.58 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O10—H11···O40.80 (2)1.95 (2)2.7330 (16)165 (2)
O3—H3···O10i0.82 (3)1.70 (3)2.5143 (14)177 (3)
O10—H12···N1ii0.86 (2)1.98 (2)2.8234 (18)166 (2)
O1—H1···O2iii0.94 (4)1.71 (4)2.6363 (13)170 (3)
Symmetry codes: (i) x+2, y+1, z+2; (ii) x, y+1, z; (iii) x, y, z+1.
 

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