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In the title compound, C9H10N4O4·H2O, the triazole ring is nearly planar. The 1,3-dioxane-4,6-dione ring exhibits a half-chair conformation. Two intra­molecular N—H...·O hydrogen bonds, with O...H distances of 2.23 (2) and 1.99 (2) Å, and two inter­molecular O—H...·N hydrogen bonds, with N...H distances of 1.92 (3) and 1.94 (4) Å, are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022750/nc6036sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022750/nc6036Isup2.hkl
Contains datablock I

CCDC reference: 282543

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.103
  • Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 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 0 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

Computing details top

Data collection: CAD-4-PC Software (Enraf–Nonius, 1993); cell refinement: CAD-4-PC Software; data reduction: XCAD (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2004); software used to prepare material for publication: SHELXL97.

(I) top
Crystal data top
C9H10N4O4·H2OF(000) = 536
Mr = 256.23Dx = 1.440 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 18.012 (5) Åθ = 5.1–20.4°
b = 5.356 (5) ŵ = 0.12 mm1
c = 12.937 (5) ÅT = 193 K
β = 108.786 (5)°Prismatic, colorless
V = 1181.6 (12) Å30.50 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.028
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 1.2°
Graphite monochromatorh = 210
ω/2θ scansk = 06
2126 measured reflectionsl = 1415
2058 independent reflections3 standard reflections every 200 reflections
1504 reflections with I > 2σ(I) intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0425P)2 + 0.3902P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2058 reflectionsΔρmax = 0.25 e Å3
176 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.031 (2)
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
C10.35489 (12)0.5497 (4)0.97169 (16)0.0427 (5)
H10.31830.67840.95750.051*
N20.40545 (11)0.5005 (4)1.06606 (14)0.0490 (5)
N30.44961 (11)0.2979 (4)1.05313 (13)0.0509 (5)
C40.42304 (13)0.2357 (4)0.95069 (16)0.0465 (5)
H40.44250.10610.91910.056*
N50.36322 (9)0.3861 (3)0.89694 (12)0.0368 (4)
N60.32277 (10)0.3864 (4)0.78542 (13)0.0400 (4)
C70.26956 (11)0.2132 (4)0.74386 (15)0.0361 (5)
H70.25970.10090.79270.043*
C80.22740 (11)0.1824 (4)0.63604 (14)0.0339 (4)
C90.17387 (13)0.0279 (4)0.60775 (17)0.0444 (5)
O90.16466 (11)0.1838 (3)0.66980 (13)0.0709 (6)
O100.13246 (8)0.0530 (3)0.49951 (11)0.0483 (4)
C110.12131 (11)0.1637 (4)0.43119 (15)0.0397 (5)
O120.19482 (8)0.2884 (3)0.44785 (10)0.0428 (4)
C130.23999 (11)0.3376 (4)0.55254 (15)0.0357 (5)
O130.28936 (8)0.4991 (3)0.56709 (11)0.0479 (4)
C1110.06421 (13)0.3383 (5)0.45610 (19)0.0543 (6)
H11A0.01520.25400.44450.082*
H11B0.05620.48120.40890.082*
H11C0.08470.39160.53080.082*
C1120.09524 (15)0.0712 (5)0.31547 (17)0.0624 (7)
H11D0.04600.01380.30020.094*
H11E0.13380.04190.30560.094*
H11F0.08930.21020.26660.094*
O1W0.40935 (10)0.7898 (3)0.76790 (13)0.0551 (5)
H60.3378 (13)0.499 (5)0.7489 (18)0.052 (7)*
H1WA0.4116 (15)0.856 (5)0.704 (2)0.073 (8)*
H1WB0.462 (2)0.769 (7)0.815 (3)0.110 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0491 (12)0.0426 (12)0.0371 (11)0.0010 (10)0.0147 (10)0.0049 (10)
N20.0562 (11)0.0553 (12)0.0344 (10)0.0028 (10)0.0131 (9)0.0081 (9)
N30.0536 (11)0.0585 (12)0.0338 (10)0.0038 (10)0.0045 (8)0.0010 (9)
C40.0496 (12)0.0494 (13)0.0368 (11)0.0088 (11)0.0090 (10)0.0023 (10)
N50.0413 (9)0.0403 (9)0.0253 (8)0.0010 (8)0.0061 (7)0.0004 (7)
N60.0471 (10)0.0428 (10)0.0260 (9)0.0055 (9)0.0059 (8)0.0035 (8)
C70.0405 (11)0.0340 (11)0.0350 (10)0.0004 (9)0.0137 (9)0.0020 (9)
C80.0356 (10)0.0350 (11)0.0310 (10)0.0004 (9)0.0107 (8)0.0008 (8)
C90.0505 (12)0.0417 (13)0.0405 (11)0.0058 (10)0.0140 (10)0.0016 (10)
O90.0929 (14)0.0588 (11)0.0573 (10)0.0318 (10)0.0189 (9)0.0086 (9)
O100.0555 (9)0.0397 (9)0.0434 (8)0.0083 (7)0.0071 (7)0.0080 (7)
C110.0382 (11)0.0422 (12)0.0351 (11)0.0038 (9)0.0070 (8)0.0047 (9)
O120.0384 (8)0.0607 (10)0.0279 (7)0.0072 (7)0.0086 (6)0.0010 (7)
C130.0334 (10)0.0404 (12)0.0323 (10)0.0018 (10)0.0093 (8)0.0017 (9)
O130.0451 (8)0.0541 (10)0.0410 (8)0.0144 (8)0.0091 (6)0.0065 (7)
C1110.0405 (12)0.0584 (15)0.0609 (14)0.0034 (12)0.0119 (10)0.0076 (12)
C1120.0614 (15)0.0806 (19)0.0378 (12)0.0085 (14)0.0057 (11)0.0160 (12)
O1W0.0593 (11)0.0631 (11)0.0353 (8)0.0123 (9)0.0044 (8)0.0098 (8)
Geometric parameters (Å, º) top
C1—N21.293 (3)C9—O101.365 (2)
C1—N51.348 (3)O10—C111.433 (3)
C1—H10.9300C11—O121.436 (2)
N2—N31.387 (3)C11—C1111.500 (3)
N3—C41.299 (3)C11—C1121.502 (3)
C4—N51.346 (3)O12—C131.362 (2)
C4—H40.9300C13—O131.211 (2)
N5—N61.391 (2)C111—H11A0.9600
N6—C71.317 (3)C111—H11B0.9600
N6—H60.86 (2)C111—H11C0.9600
C7—C81.367 (3)C112—H11D0.9600
C7—H70.9300C112—H11E0.9600
C8—C131.437 (3)C112—H11F0.9600
C8—C91.451 (3)O1W—H1WA0.91 (3)
C9—O91.207 (3)O1W—H1WB0.96 (4)
N2—C1—N5109.7 (2)O10—C11—O12110.17 (16)
N2—C1—H1125.1O10—C11—C111110.00 (17)
N5—C1—H1125.1O12—C11—C111109.92 (18)
C1—N2—N3107.60 (17)O10—C11—C112106.52 (19)
C4—N3—N2106.64 (17)O12—C11—C112106.28 (17)
N3—C4—N5110.1 (2)C111—C11—C112113.83 (19)
N3—C4—H4124.9C13—O12—C11117.76 (14)
N5—C4—H4124.9O13—C13—O12117.78 (17)
C4—N5—C1105.89 (17)O13—C13—C8125.57 (18)
C4—N5—N6126.95 (17)O12—C13—C8116.56 (17)
C1—N5—N6126.95 (18)C11—C111—H11A109.5
C7—N6—N5119.46 (18)C11—C111—H11B109.5
C7—N6—H6125.8 (15)H11A—C111—H11B109.5
N5—N6—H6114.7 (15)C11—C111—H11C109.5
N6—C7—C8126.42 (19)H11A—C111—H11C109.5
N6—C7—H7116.8H11B—C111—H11C109.5
C8—C7—H7116.8C11—C112—H11D109.5
C7—C8—C13121.80 (18)C11—C112—H11E109.5
C7—C8—C9117.19 (18)H11D—C112—H11E109.5
C13—C8—C9120.80 (17)C11—C112—H11F109.5
O9—C9—O10117.9 (2)H11D—C112—H11F109.5
O9—C9—C8126.3 (2)H11E—C112—H11F109.5
O10—C9—C8115.77 (18)H1WA—O1W—H1WB107 (3)
C9—O10—C11118.32 (16)
N5—C1—N2—N30.6 (2)C13—C8—C9—O105.4 (3)
C1—N2—N3—C40.1 (2)O9—C9—O10—C11159.2 (2)
N2—N3—C4—N50.8 (2)C8—C9—O10—C1123.0 (3)
N3—C4—N5—C11.1 (2)C9—O10—C11—O1249.5 (2)
N3—C4—N5—N6176.18 (19)C9—O10—C11—C11171.8 (2)
N2—C1—N5—C41.1 (2)C9—O10—C11—C112164.38 (18)
N2—C1—N5—N6176.12 (19)O10—C11—O12—C1349.7 (2)
C4—N5—N6—C777.5 (3)C111—C11—O12—C1371.7 (2)
C1—N5—N6—C7108.4 (2)C112—C11—O12—C13164.71 (18)
N5—N6—C7—C8177.18 (19)C11—O12—C13—O13159.60 (18)
N6—C7—C8—C132.8 (3)C11—O12—C13—C823.6 (3)
N6—C7—C8—C9177.56 (19)C7—C8—C13—O133.1 (3)
C7—C8—C9—O92.6 (3)C9—C8—C13—O13171.5 (2)
C13—C8—C9—O9172.2 (2)C7—C8—C13—O12179.60 (18)
C7—C8—C9—O10179.79 (18)C9—C8—C13—O125.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6···O130.86 (2)2.23 (2)2.759 (2)119.6 (19)
N6—H6···O1W0.86 (2)1.99 (2)2.717 (3)142 (2)
O1W—H1WA···N2i0.91 (3)1.92 (3)2.822 (3)174 (2)
O1W—H1WB···N3ii0.96 (4)1.95 (4)2.872 (3)160 (3)
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+1, y+1, z+2.
 

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