organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

4,5-Bis(1H-tetra­zol-5-yl)-1H-imidazole monohydrate

aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
*Correspondence e-mail: seuwangwei@gmail.com

(Received 29 April 2009; accepted 12 May 2009; online 29 May 2009)

The title compound, C5H4N10·H2O, is composed of three five-membered rings that are essentially coplanar, the dihedral angles between the imidazole ring and the tetra­zole rings being 3.5 (2) and 3.0 (2)°. In the crystal, inter­molecular O—H⋯N, N—H⋯O and N—H⋯N hydrogen bonds lead to the formation of a three-dimensional network. An intra­molecular N—H⋯N hydrogen bond is also present.

Related literature

For the example of a zinc complex by reaction of the title compound as ligand, see: Zhao et al. (2004[Zhao, H., Ye, Q., Wu, Q., Song, Y.-M., Liu, Y.-J. & Xiong, R.-G. (2004). Z. Anorg. Allg. Chem. 630, 1367-1370.]).

[Scheme 1]

Experimental

Crystal data
  • C5H4N10·H2O

  • Mr = 222.20

  • Monoclinic, P 21 /c

  • a = 15.607 (3) Å

  • b = 3.6706 (7) Å

  • c = 18.127 (7) Å

  • β = 119.13 (2)°

  • V = 907.1 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 294 K

  • 0.08 × 0.08 × 0.03 mm

Data collection
  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.892, Tmax = 0.990

  • 7767 measured reflections

  • 1785 independent reflections

  • 1362 reflections with I > 2σ(I)

  • Rint = 0.061

Refinement
  • R[F2 > 2σ(F2)] = 0.071

  • wR(F2) = 0.201

  • S = 1.06

  • 1785 reflections

  • 153 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.60 e Å−3

  • Δρmin = −0.56 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H2W⋯N3i 0.91 (2) 2.12 (2) 3.014 (4) 169 (5)
O1W—H1W⋯N9ii 0.91 (2) 1.99 (2) 2.884 (4) 169 (5)
N2—H2A⋯O1Wi 0.86 2.41 3.188 (4) 151
N7—H7A⋯N1iii 0.86 2.10 2.799 (4) 139
N6—H6A⋯N10 0.86 1.95 2.711 (4) 146
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) [-x+1, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]; (iii) -x, -y, -z+1.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The crystal data show that in the title compound, C5H4N10 × H2O, the molecule is essentially planar with dihedral angles between imidazole and the tetrazole rings of 3.5 (2)° and 3.0 (2)°, respectively.

Intramolecular hydrogen bonds between the tetrazole rings determine the conformation of the molecule. It is also interesting to note that strong intermolecular have been found between the tetrazole and imidazole rings towards the solvent water molecules. This results in the formation of a three-dimensional network, as shown in Figure 2.

Related literature top

For the structure of a related zinc complex, see: Zhao et al. (2004).

Experimental top

NaN3 (0.975 g,15 mmol) and NH4Cl (0.587 g, 11 mmol) were added to a solution of (4,5-Dicyano)-imidazole (1.18 g,10 mmol) in DMF (25 ml) under magnetic stirring in an oil bath. The resulting mixture was heated to 90°C for 8 h until the starting material was fully consumed as shown with the help of TLC detection. The mixture was allowed to cool to room temperature and acidified to pH = 2 with 1M aqueous HCl. The resulting precipitate was collected, washed with a small amount of water and dried at 60°C for 12 h. Colorless crystals of the title compound suitable for X-ray diffraction were obtained from an ethanolic solution after one week.

Refinement top

Positional parameters of all the H atoms bonded to C and N atoms were calculated geometrically with Uiso(H) = 1.2Ueq(C,N). The O—H hydrogen atoms of the water molecule were located in a difference Fourier map and refined freely with isotropic temperature factors.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Three-dimensional network of the title compound viewed along a axis.
4,5-Bis(1H-tetrazol-5-yl)-1H-imidazole monohydrate top
Crystal data top
C5H4N10·H2OF(000) = 456
Mr = 222.20Dx = 1.627 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2076 reflections
a = 15.607 (3) Åθ = 2.0–27.5°
b = 3.6706 (7) ŵ = 0.13 mm1
c = 18.127 (7) ÅT = 294 K
β = 119.13 (2)°Block, colorless
V = 907.1 (5) Å30.08 × 0.08 × 0.03 mm
Z = 4
Data collection top
Rigaku SCXmini
diffractometer
1785 independent reflections
Radiation source: fine-focus sealed tube1362 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
Detector resolution: 13.6612 pixels mm-1θmax = 26.0°, θmin = 3.6°
ω scansh = 1919
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 44
Tmin = 0.892, Tmax = 0.990l = 2222
7767 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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0998P)2 + 1.6707P]
where P = (Fo2 + 2Fc2)/3
1785 reflections(Δ/σ)max < 0.001
153 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.56 e Å3
Crystal data top
C5H4N10·H2OV = 907.1 (5) Å3
Mr = 222.20Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.607 (3) ŵ = 0.13 mm1
b = 3.6706 (7) ÅT = 294 K
c = 18.127 (7) Å0.08 × 0.08 × 0.03 mm
β = 119.13 (2)°
Data collection top
Rigaku SCXmini
diffractometer
1785 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1362 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.990Rint = 0.061
7767 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0710 restraints
wR(F2) = 0.201H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.60 e Å3
1785 reflectionsΔρmin = 0.56 e Å3
153 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
O1W0.6668 (2)1.0057 (9)0.61964 (19)0.0429 (8)
N50.4974 (2)0.4374 (9)0.67749 (19)0.0313 (8)
N60.40302 (19)0.3471 (9)0.64859 (17)0.0260 (7)
H6A0.37940.25190.67830.031*
N90.2305 (2)0.0391 (9)0.73314 (18)0.0305 (7)
N100.2612 (2)0.0904 (9)0.68015 (18)0.0267 (7)
N10.0913 (2)0.2414 (9)0.45237 (17)0.0270 (7)
N70.1017 (2)0.0035 (9)0.61097 (18)0.0302 (8)
H7A0.04200.00630.57090.036*
N80.1358 (2)0.0896 (10)0.69193 (19)0.0337 (8)
N40.5023 (2)0.5693 (9)0.61343 (19)0.0294 (7)
N20.2075 (2)0.4482 (8)0.42653 (17)0.0263 (7)
H2A0.23710.53170.40060.032*
N30.4130 (2)0.5680 (8)0.54265 (17)0.0267 (7)
C10.1142 (3)0.3667 (11)0.3940 (2)0.0314 (9)
H1A0.06880.39240.33710.038*
C50.3516 (2)0.4283 (9)0.5666 (2)0.0201 (7)
C40.1794 (2)0.1138 (9)0.6055 (2)0.0212 (7)
C20.2476 (2)0.3706 (9)0.5112 (2)0.0209 (7)
C30.1767 (2)0.2407 (9)0.5288 (2)0.0211 (7)
H1W0.698 (3)1.123 (14)0.670 (2)0.067 (16)*
H2W0.635 (3)1.117 (14)0.568 (2)0.069 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1W0.0462 (18)0.0463 (18)0.0335 (17)0.0038 (14)0.0172 (15)0.0008 (14)
N50.0211 (15)0.044 (2)0.0262 (16)0.0073 (13)0.0094 (13)0.0022 (14)
N60.0198 (14)0.0368 (17)0.0210 (14)0.0051 (13)0.0095 (12)0.0011 (12)
N90.0284 (16)0.0370 (18)0.0242 (15)0.0031 (13)0.0114 (13)0.0054 (13)
N100.0215 (14)0.0366 (17)0.0201 (14)0.0032 (13)0.0088 (12)0.0036 (13)
N10.0198 (14)0.0370 (18)0.0192 (14)0.0032 (13)0.0055 (12)0.0010 (13)
N70.0207 (15)0.0437 (19)0.0223 (15)0.0063 (13)0.0074 (12)0.0039 (13)
N80.0302 (17)0.046 (2)0.0254 (16)0.0057 (15)0.0142 (14)0.0056 (14)
N40.0236 (15)0.0361 (18)0.0273 (16)0.0066 (13)0.0114 (13)0.0014 (13)
N20.0244 (15)0.0352 (17)0.0211 (15)0.0028 (13)0.0125 (13)0.0034 (13)
N30.0209 (14)0.0338 (17)0.0238 (15)0.0041 (13)0.0097 (13)0.0004 (13)
C10.0250 (18)0.045 (2)0.0185 (17)0.0020 (16)0.0058 (15)0.0032 (15)
C50.0208 (16)0.0219 (16)0.0199 (16)0.0018 (13)0.0117 (14)0.0015 (13)
C40.0199 (16)0.0236 (17)0.0192 (16)0.0014 (14)0.0087 (13)0.0008 (13)
C20.0206 (16)0.0222 (17)0.0177 (16)0.0023 (13)0.0076 (13)0.0028 (13)
C30.0168 (15)0.0263 (18)0.0193 (16)0.0016 (13)0.0081 (13)0.0003 (14)
Geometric parameters (Å, º) top
O1W—H1W0.91 (2)N7—N81.339 (4)
O1W—H2W0.91 (2)N7—H7A0.8600
N5—N41.294 (4)N4—N31.359 (4)
N5—N61.343 (4)N2—C11.313 (4)
N6—C51.335 (4)N2—C21.375 (4)
N6—H6A0.8600N2—H2A0.8600
N9—N81.303 (4)N3—C51.332 (4)
N9—N101.352 (4)C1—H1A0.9300
N10—C41.336 (4)C5—C21.450 (4)
N1—C11.351 (5)C4—C31.446 (4)
N1—C31.378 (4)C2—C31.378 (5)
N7—C41.327 (4)
H1W—O1W—H2W125 (5)C5—N3—N4105.3 (3)
N4—N5—N6105.9 (3)N2—C1—N1112.6 (3)
C5—N6—N5109.3 (3)N2—C1—H1A123.7
C5—N6—H6A125.4N1—C1—H1A123.7
N5—N6—H6A125.4N3—C5—N6108.1 (3)
N8—N9—N10109.7 (3)N3—C5—C2124.8 (3)
C4—N10—N9104.4 (3)N6—C5—C2127.1 (3)
C1—N1—C3107.0 (3)N7—C4—N10111.2 (3)
C4—N7—N8105.6 (3)N7—C4—C3124.7 (3)
C4—N7—H7A127.2N10—C4—C3124.1 (3)
N8—N7—H7A127.2N2—C2—C3110.5 (3)
N9—N8—N7109.1 (3)N2—C2—C5119.4 (3)
N5—N4—N3111.4 (3)C3—C2—C5130.1 (3)
C1—N2—C2104.8 (3)C2—C3—N1105.0 (3)
C1—N2—H2A127.6C2—C3—C4133.1 (3)
C2—N2—H2A127.6N1—C3—C4121.9 (3)
N4—N5—N6—C50.3 (4)C1—N2—C2—C30.1 (4)
N8—N9—N10—C40.1 (4)C1—N2—C2—C5179.6 (3)
N10—N9—N8—N70.2 (4)N3—C5—C2—N22.9 (5)
C4—N7—N8—N90.4 (4)N6—C5—C2—N2175.6 (3)
N6—N5—N4—N30.0 (4)N3—C5—C2—C3177.6 (4)
N5—N4—N3—C50.3 (4)N6—C5—C2—C33.8 (6)
C2—N2—C1—N10.1 (4)N2—C2—C3—N10.2 (4)
C3—N1—C1—N20.2 (5)C5—C2—C3—N1179.6 (3)
N4—N3—C5—N60.5 (4)N2—C2—C3—C4178.4 (3)
N4—N3—C5—C2179.2 (3)C5—C2—C3—C41.1 (6)
N5—N6—C5—N30.5 (4)C1—N1—C3—C20.2 (4)
N5—N6—C5—C2179.2 (3)C1—N1—C3—C4178.6 (3)
N8—N7—C4—N100.5 (4)N7—C4—C3—C2178.5 (4)
N8—N7—C4—C3179.9 (3)N10—C4—C3—C21.9 (6)
N9—N10—C4—N70.3 (4)N7—C4—C3—N13.1 (5)
N9—N10—C4—C3179.9 (3)N10—C4—C3—N1176.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W···N3i0.91 (2)2.12 (2)3.014 (4)169 (5)
N2—H2A···O1Wi0.862.413.188 (4)151
O1W—H1W···N9ii0.91 (2)1.99 (2)2.884 (4)169 (5)
N7—H7A···N1iii0.862.102.799 (4)139
N6—H6A···N100.861.952.711 (4)146
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+3/2, z+3/2; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC5H4N10·H2O
Mr222.20
Crystal system, space groupMonoclinic, P21/c
Temperature (K)294
a, b, c (Å)15.607 (3), 3.6706 (7), 18.127 (7)
β (°) 119.13 (2)
V3)907.1 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.08 × 0.08 × 0.03
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.892, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
7767, 1785, 1362
Rint0.061
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.201, 1.06
No. of reflections1785
No. of parameters153
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.60, 0.56

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H2W···N3i0.91 (2)2.12 (2)3.014 (4)169 (5)
N2—H2A···O1Wi0.862.413.188 (4)151.0
O1W—H1W···N9ii0.91 (2)1.99 (2)2.884 (4)169 (5)
N7—H7A···N1iii0.862.102.799 (4)138.5
N6—H6A···N100.861.952.711 (4)146.1
Symmetry codes: (i) x+1, y+2, z+1; (ii) x+1, y+3/2, z+3/2; (iii) x, y, z+1.
 

Acknowledgements

The author is grateful to the Starter Fund of Southeast University for financial support to buy the CCD X-ray diffractometer.

References

First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhao, H., Ye, Q., Wu, Q., Song, Y.-M., Liu, Y.-J. & Xiong, R.-G. (2004). Z. Anorg. Allg. Chem. 630, 1367–1370.  Web of Science CSD CrossRef CAS Google Scholar

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