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The title compound, C7H8N6O·2H2O, contains a tetrazole ring fused to a substituted pyridone ring. Bond lengths correspond to delocalized π electrons in the tetrazole moiety and a push–pull effect in the pyridone ring. An extended network of hydrogen bonds connects the mol­ecules in planes parallel to the bc plane, while the water mol­ecules form chains parallel to the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021366/na6250sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021366/na6250Isup2.hkl
Contains datablock I

CCDC reference: 226930

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.124
  • Data-to-parameter ratio = 9.8

checkCIF/PLATON results

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Alert level B PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 93 PerFit
Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.00 Sigma PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.36 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 29.99 From the CIF: _reflns_number_total 1789 Count of symmetry unique reflns 1788 Completeness (_total/calc) 100.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; 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: PLATON (Spek, 1998).

5-Amino-8-(1-aminoethylidene)-8H-tetrazolo[1,5-a]pyridin-7-one dihydrate top
Crystal data top
C7H8N6O·2H2ODx = 1.434 Mg m3
Mr = 228.23Melting point: 568 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 42 reflections
a = 6.751 (1) Åθ = 4–38°
b = 11.990 (1) ŵ = 0.12 mm1
c = 13.061 (1) ÅT = 293 K
V = 1057.2 (2) Å3Plate, colourless
Z = 40.3 × 0.2 × 0.1 mm
F(000) = 480
Data collection top
Siemens P4
diffractometer
Rint = 0.032
Radiation source: sealed tubeθmax = 30.0°, θmin = 2.3°
Graphite monochromatorh = 99
ω scansk = 1616
3578 measured reflectionsl = 1818
1789 independent reflections3 standard reflections every 97 reflections
1049 reflections with I > 2σ(I) intensity decay: no decay
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.051 w = 1/[σ2(Fo2) + (0.0575P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.124(Δ/σ)max < 0.001
S = 0.99Δρmax = 0.21 e Å3
1789 reflectionsΔρmin = 0.25 e Å3
182 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
6 restraintsExtinction coefficient: 0.0036 (12)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Friedel pairs have been merged before the refinement
Secondary atom site location: difference Fourier map
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
C10.9686 (6)0.7686 (2)0.9601 (2)0.0333 (7)
C20.9689 (5)0.8591 (2)1.0304 (2)0.0341 (7)
C40.9663 (6)0.7339 (2)1.1788 (2)0.0348 (7)
C50.9694 (6)0.6456 (2)1.1142 (2)0.0360 (7)
C60.9711 (5)0.6571 (2)1.0053 (2)0.0346 (7)
C120.9676 (6)0.7846 (2)0.8528 (2)0.0366 (7)
C130.9647 (7)0.8968 (3)0.8031 (2)0.0483 (9)
H13A0.96100.88810.73000.098 (16)*
H13B1.08160.93740.82210.052 (11)*
H13C0.84950.93710.82520.104 (17)*
N30.9658 (5)0.83895 (17)1.13309 (16)0.0367 (6)
N70.9661 (5)0.93700 (19)1.18498 (18)0.0515 (8)
N80.9688 (6)1.01315 (18)1.11538 (19)0.0543 (8)
N90.9699 (5)0.97058 (18)1.01892 (18)0.0452 (7)
N100.9620 (7)0.7331 (2)1.28145 (19)0.0516 (9)
N140.9673 (6)0.6976 (2)0.7920 (2)0.0496 (7)
O10.9743 (7)0.36641 (19)1.0375 (2)0.0848 (12)
O21.0818 (5)0.1794 (2)0.92370 (19)0.0705 (10)
O110.9743 (4)0.57040 (15)0.94936 (14)0.0471 (6)
H20.992 (8)0.122 (4)0.950 (5)0.148 (12)*
H2'1.226 (5)0.168 (5)0.925 (5)0.148 (12)*
H10.987 (10)0.437 (3)1.000 (4)0.148 (12)*
H1'1.010 (11)0.308 (4)0.988 (4)0.148 (12)*
H100.974 (6)0.665 (3)1.312 (3)0.054 (10)*
H10'0.971 (6)0.797 (3)1.310 (2)0.044 (9)*
H140.960 (6)0.707 (3)0.723 (3)0.054 (10)*
H14'0.951 (7)0.631 (3)0.825 (3)0.077 (14)*
H50.974 (5)0.572 (2)1.137 (2)0.031 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0401 (18)0.0287 (12)0.0312 (13)0.0020 (15)0.0007 (15)0.0002 (10)
C20.0408 (18)0.0299 (12)0.0316 (13)0.0031 (15)0.0002 (15)0.0026 (10)
C40.0458 (19)0.0261 (12)0.0326 (14)0.0007 (16)0.0007 (17)0.0055 (10)
C50.0463 (19)0.0266 (13)0.0352 (14)0.0008 (16)0.0006 (16)0.0036 (10)
C60.0383 (17)0.0316 (13)0.0338 (13)0.0020 (17)0.0006 (14)0.0007 (11)
C120.0364 (16)0.0408 (14)0.0325 (13)0.0040 (17)0.0017 (15)0.0001 (12)
C130.061 (2)0.0478 (17)0.0361 (17)0.000 (2)0.0019 (19)0.0106 (14)
N30.0566 (17)0.0250 (9)0.0287 (10)0.0001 (15)0.0018 (13)0.0016 (9)
N70.088 (2)0.0283 (11)0.0383 (13)0.0040 (17)0.0006 (18)0.0032 (10)
N80.093 (2)0.0294 (11)0.0406 (13)0.0022 (17)0.0014 (19)0.0001 (10)
N90.0674 (19)0.0285 (11)0.0397 (13)0.0004 (16)0.0019 (16)0.0024 (10)
N100.092 (3)0.0289 (12)0.0339 (13)0.0006 (18)0.0004 (19)0.0035 (11)
N140.071 (2)0.0471 (14)0.0307 (13)0.0004 (18)0.0007 (17)0.0004 (12)
O10.170 (4)0.0402 (12)0.0445 (13)0.002 (2)0.011 (2)0.0062 (10)
O20.127 (3)0.0435 (13)0.0408 (12)0.0119 (18)0.0039 (16)0.0066 (11)
O110.0728 (15)0.0294 (9)0.0391 (11)0.0003 (13)0.0004 (13)0.0047 (8)
Geometric parameters (Å, º) top
C1—C121.415 (4)C13—H13B0.9600
C1—C21.421 (4)C13—H13C0.9600
C1—C61.461 (4)N3—N71.357 (3)
C2—N91.345 (3)N7—N81.289 (3)
C2—N31.363 (3)N8—N91.359 (3)
C4—N101.342 (4)N10—H100.92 (3)
C4—C51.353 (4)N10—H10'0.86 (3)
C4—N31.393 (3)N14—H140.91 (4)
C5—C61.430 (4)N14—H14'0.92 (4)
C5—H50.94 (3)O1—H10.98 (3)
C6—O111.270 (3)O1—H1'0.98 (3)
C12—N141.311 (4)O2—H20.98 (3)
C12—C131.494 (4)O2—H2'0.98 (3)
C13—H13A0.9600
C12—C1—C2122.4 (2)C12—C13—H13B109.5
C12—C1—C6121.6 (2)H13A—C13—H13B109.5
C2—C1—C6116.0 (2)C12—C13—H13C109.5
N9—C2—N3106.6 (2)H13A—C13—H13C109.5
N9—C2—C1133.4 (3)H13B—C13—H13C109.5
N3—C2—C1120.0 (2)N7—N3—C2109.8 (2)
N10—C4—C5128.1 (2)N7—N3—C4124.7 (2)
N10—C4—N3115.8 (2)C2—N3—C4125.5 (2)
C5—C4—N3116.1 (2)N8—N7—N3105.2 (2)
C4—C5—C6123.0 (2)N7—N8—N9112.8 (2)
C4—C5—H5123.0 (16)C2—N9—N8105.7 (2)
C6—C5—H5114.0 (16)C4—N10—H10116 (2)
O11—C6—C5119.6 (2)C4—N10—H10'115 (2)
O11—C6—C1121.1 (2)H10—N10—H10'127 (3)
C5—C6—C1119.3 (2)C12—N14—H14120 (2)
N14—C12—C1119.4 (3)C12—N14—H14'114 (2)
N14—C12—C13117.0 (3)H14—N14—H14'125 (3)
C1—C12—C13123.6 (2)H1—O1—H1'105 (4)
C12—C13—H13A109.5H2—O2—H2'121 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N9i0.98 (3)2.04 (5)2.896 (4)146 (5)
O2—H2···O1ii0.98 (3)1.80 (4)2.753 (6)164 (5)
O1—H1···O110.98 (3)1.73 (4)2.703 (3)169 (6)
O1—H1···O20.98 (3)1.82 (3)2.786 (4)166 (5)
N10—H10···N8iii0.92 (3)2.09 (4)2.998 (3)174 (4)
N10—H10···O1iv0.86 (3)2.19 (3)2.886 (4)139 (3)
N14—H14···O2v0.91 (4)1.96 (4)2.845 (4)162 (3)
N14—H14···O110.92 (4)1.78 (4)2.560 (4)141 (4)
Symmetry codes: (i) x, y1, z; (ii) x+1/2, y+1/2, z+2; (iii) x+2, y1/2, z+5/2; (iv) x+2, y+1/2, z+5/2; (v) x+2, y+1/2, z+3/2.
 

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