5-[4-(1H-Imidazol-1-yl)phen­yl]-2H-tetra­zole dihydrate

Zhang, Y.-H.; Tian, D.-M.

doi:10.1107/S1600536811019647

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1537

doi:10.1107/S1600536811019647

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5-[4-(1H-Imidazol-1-yl)phenyl]-2H-tetrazole dihydrate

Yan-Hua Zhang ^a and Da-Min Tian ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Henan University of Urban Construction, Pingdingshan, Henan, People's Republic of China
^*Correspondence e-mail: tiandamin2009@163.com

(Received 21 May 2011; accepted 24 May 2011; online 28 May 2011)

In the title compound, C₁₀H₈N₆·2H₂O, the central aromatic ring makes dihedral angles of 23.59 (15) and 16.99 (16)° with the terminal imidazole and tetrazole rings, respectively, which are themselves almost coplanar [dihedral angle = 6.61 (18)°]. Two H atoms of the two water molecules are half occupied. In the crystal packing, weak intermolecular O—H⋯N, O—H⋯O and N—H⋯N hydrogen bonds and π–π stacking interactions [centroid–centroid distances of 3.73 (4) Å between benzene rings and 3.66 (3) Å between imidazole and tetrazole rings] are observed.

Related literature

For the biological activity of imidazole derivatives, see: Reichardt et al. (1992 )

Experimental

Crystal data

C₁₀H₈N₆·2H₂O
M_r = 248.26
Triclinic, $[P \overline 1]$
a = 7.4300 (7) Å
b = 8.2285 (9) Å
c = 10.2047 (11) Å
α = 97.011 (1)°
β = 90.813 (1)°
γ = 113.449 (2)°
V = 566.74 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.38 × 0.17 × 0.16 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.960, T_max = 0.983
2913 measured reflections
1953 independent reflections
1199 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.243
S = 1.05
1953 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2D⋯N2ⁱ	0.85	2.50	3.235 (7)	146
O2—H2D⋯N3ⁱ	0.85	1.98	2.823 (7)	172
O2—H2C⋯O1ⁱⁱ	0.85	2.15	2.994 (9)	170
O2—H2A⋯O1	0.85	1.92	2.629 (9)	141
O1—H1D⋯O2ⁱⁱ	0.85	2.55	2.994 (9)	114
O1—H1D⋯O2	0.85	1.78	2.629 (9)	175
O1—H1C⋯O1ⁱⁱⁱ	0.85	1.96	2.806 (11)	175
O1—H1A⋯N1	0.85	1.99	2.790 (5)	157
N2—H2⋯N6^iv	0.86	1.90	2.758 (5)	174
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -z; (iv) x, y-1, z-1.

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019647/jh2291sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019647/jh2291Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019647/jh2291Isup3.cml

checkCIF report

Comment top

Imidazole derivatives possessing the biologically important imdidazole ring, have been studied in terms of their biological activities (Reichardt et al., 1992). Inspired by this, we focus on the studies of imidazole derivatives Recently, we have obtain a new crystal structure of imidazole derivative (1-tetrazole-4-imidazole-benzene), which is crystallized by the slow evaporation of ethonal sovlent at room temperaure.

As shown in Fig.1, the title molecule crystallizes as a neutral, with two terminal imidazole and tetrazole rings almost coplanar with the dihedral angle of 6.61 (18) °. They makes dihedral angles of 23.59 (15) ° and 16.99 (16) ° with the central aromatic ring. It is noted that there are two types of π-π stacking interactions: one occurs between parallel benzene rings with centroid-centroid distances of 3.73 (4) Å; the other occurs between the imidazole and tetrazole rings with centroid-centroid distances of 3.66 (3) Å. Thus, A wide range of hydrogen bonds (O—H···N, O—H···O and N—H···N) and π-π stacking interactions contribute to the formation of the supramolecular network.

Related literature top

For the biological activity of imidazole derivatives, see: Reichardt et al. (1992)

Experimental top

1-tetrazole-4-imidazole-benzene(0.1 g, 0.4 mmol) was dissolved in ethonal (20 ml) and the solution was left to evaporate slowly at room temperature. After a week, colourless crystals suitable for X-ray analysis were obtained.

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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

Fig. 1. The structure of the title compound, showing the atomic numbering scheme with 30% probability displacement ellipsoids

5-[4-(1H-Imidazol-1-yl)phenyl]-2H-tetrazole dihydrate top

Crystal data top

C₁₀H₈N₆·2H₂O	Z = 2
M_r = 248.26	F(000) = 260
Triclinic, P1	D_x = 1.455 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4300 (7) Å	Cell parameters from 1702 reflections
b = 8.2285 (9) Å	θ = 2.5–25.9°
c = 10.2047 (11) Å	µ = 0.11 mm⁻¹
α = 97.011 (1)°	T = 298 K
β = 90.813 (1)°	Block, colorless
γ = 113.449 (2)°	0.38 × 0.17 × 0.16 mm
V = 566.74 (10) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1953 independent reflections
Radiation source: fine-focus sealed tube	1199 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.0°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −8→8
T_min = 0.960, T_max = 0.983	k = −9→9
2913 measured reflections	l = −11→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.075	H-atom parameters constrained
wR(F²) = 0.243	w = 1/[σ²(F_o²) + (0.1194P)² + 0.5477P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1953 reflections	Δρ_max = 0.40 e Å⁻³
164 parameters	Δρ_min = −0.51 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.13 (2)

Crystal data top

C₁₀H₈N₆·2H₂O	γ = 113.449 (2)°
M_r = 248.26	V = 566.74 (10) Å³
Triclinic, P1	Z = 2
a = 7.4300 (7) Å	Mo Kα radiation
b = 8.2285 (9) Å	µ = 0.11 mm⁻¹
c = 10.2047 (11) Å	T = 298 K
α = 97.011 (1)°	0.38 × 0.17 × 0.16 mm
β = 90.813 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	1953 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	1199 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.983	R_int = 0.024
2913 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.243	H-atom parameters constrained
S = 1.05	Δρ_max = 0.40 e Å⁻³
1953 reflections	Δρ_min = −0.51 e Å⁻³
164 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.2591 (5)	0.1994 (4)	0.1928 (3)	0.0420 (9)
N2	0.2495 (6)	0.0363 (4)	0.1481 (3)	0.0483 (10)
H2	0.2561	−0.0008	0.0665	0.058*
N3	0.2288 (6)	−0.0589 (5)	0.2440 (3)	0.0499 (10)
N4	0.2239 (6)	0.0414 (4)	0.3577 (3)	0.0457 (10)
N5	0.2568 (4)	0.7806 (4)	0.6934 (3)	0.0329 (8)
N6	0.2612 (5)	0.9372 (4)	0.8813 (3)	0.0447 (10)
O1	0.2945 (8)	0.4108 (6)	−0.0073 (4)	0.1116 (18)
H1A	0.2650	0.3229	0.0363	0.134*
H1C	0.4182	0.4705	−0.0013	0.134*	0.50
H1D	0.2401	0.4795	0.0231	0.134*	0.50
O2	0.1048 (12)	0.6070 (9)	0.0820 (6)	0.183 (3)
H2A	0.2078	0.5941	0.0576	0.220*	0.50
H2C	−0.0111	0.5894	0.0548	0.220*	0.50
H2D	0.1533	0.7067	0.1322	0.220*
C1	0.2426 (5)	0.1985 (5)	0.3235 (3)	0.0320 (9)
C2	0.2436 (5)	0.3498 (5)	0.4159 (3)	0.0304 (9)
C3	0.3121 (6)	0.5229 (5)	0.3835 (3)	0.0377 (10)
H3	0.3556	0.5438	0.2997	0.045*
C4	0.3163 (6)	0.6638 (5)	0.4737 (4)	0.0367 (10)
H4A	0.3632	0.7788	0.4508	0.044*
C5	0.2507 (5)	0.6338 (5)	0.5985 (3)	0.0296 (9)
C6	0.1766 (6)	0.4619 (5)	0.6316 (3)	0.0372 (10)
H6	0.1290	0.4413	0.7144	0.045*
C7	0.1736 (6)	0.3217 (5)	0.5418 (3)	0.0374 (10)
H7	0.1245	0.2067	0.5648	0.045*
C8	0.2597 (6)	0.7830 (6)	0.8248 (4)	0.0416 (11)
H8	0.2604	0.6911	0.8692	0.050*
C9	0.2610 (6)	1.0379 (5)	0.7849 (4)	0.0436 (11)
H9	0.2632	1.1526	0.7977	0.052*
C10	0.2571 (6)	0.9415 (5)	0.6680 (4)	0.0424 (11)
H10	0.2550	0.9768	0.5850	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.059 (2)	0.0374 (19)	0.0299 (17)	0.0204 (17)	0.0075 (15)	−0.0007 (14)
N2	0.075 (3)	0.044 (2)	0.0252 (17)	0.027 (2)	0.0086 (16)	−0.0097 (15)
N3	0.077 (3)	0.043 (2)	0.0345 (18)	0.032 (2)	0.0062 (17)	−0.0028 (16)
N4	0.070 (3)	0.0366 (19)	0.0340 (18)	0.0267 (18)	0.0090 (16)	0.0007 (15)
N5	0.0396 (19)	0.0335 (18)	0.0248 (16)	0.0156 (15)	0.0047 (13)	−0.0015 (13)
N6	0.053 (2)	0.045 (2)	0.0346 (18)	0.0218 (18)	0.0061 (15)	−0.0048 (16)
O1	0.194 (5)	0.088 (3)	0.069 (3)	0.067 (3)	0.034 (3)	0.033 (2)
O2	0.248 (9)	0.142 (6)	0.156 (6)	0.078 (6)	0.023 (6)	0.004 (5)
C1	0.035 (2)	0.036 (2)	0.0244 (18)	0.0141 (17)	0.0037 (15)	0.0017 (16)
C2	0.032 (2)	0.036 (2)	0.0239 (18)	0.0159 (17)	0.0013 (14)	−0.0017 (15)
C3	0.049 (3)	0.041 (2)	0.0230 (18)	0.0178 (19)	0.0084 (16)	0.0051 (16)
C4	0.050 (3)	0.028 (2)	0.031 (2)	0.0137 (18)	0.0091 (17)	0.0055 (16)
C5	0.033 (2)	0.031 (2)	0.0250 (18)	0.0151 (17)	0.0019 (14)	−0.0005 (15)
C6	0.050 (3)	0.039 (2)	0.0242 (18)	0.019 (2)	0.0149 (16)	0.0045 (16)
C7	0.052 (3)	0.032 (2)	0.0300 (19)	0.0187 (19)	0.0100 (17)	0.0056 (16)
C8	0.054 (3)	0.043 (2)	0.0271 (19)	0.020 (2)	0.0049 (17)	−0.0005 (17)
C9	0.057 (3)	0.036 (2)	0.040 (2)	0.023 (2)	0.0051 (19)	−0.0023 (18)
C10	0.061 (3)	0.036 (2)	0.033 (2)	0.023 (2)	0.0077 (18)	0.0022 (17)

Geometric parameters (Å, º) top

N1—N2	1.337 (5)	O2—H2D	0.8501
N1—C1	1.341 (5)	C1—C2	1.465 (5)
N2—N3	1.300 (5)	C2—C3	1.393 (5)
N2—H2	0.8600	C2—C7	1.403 (5)
N3—N4	1.350 (5)	C3—C4	1.379 (5)
N4—C1	1.335 (5)	C3—H3	0.9300
N5—C8	1.338 (5)	C4—C5	1.386 (5)
N5—C10	1.379 (5)	C4—H4A	0.9300
N5—C5	1.438 (5)	C5—C6	1.385 (5)
N6—C8	1.324 (5)	C6—C7	1.375 (5)
N6—C9	1.362 (5)	C6—H6	0.9300
O1—H1A	0.8500	C7—H7	0.9300
O1—H1C	0.8500	C8—H8	0.9300
O1—H1D	0.8499	C9—C10	1.343 (5)
O2—H2A	0.8500	C9—H9	0.9300
O2—H2C	0.8500	C10—H10	0.9300

N2—N1—C1	104.1 (3)	C4—C3—H3	119.5
N3—N2—N1	111.2 (3)	C2—C3—H3	119.5
N3—N2—H2	124.4	C3—C4—C5	119.9 (3)
N1—N2—H2	124.4	C3—C4—H4A	120.1
N2—N3—N4	108.3 (3)	C5—C4—H4A	120.1
C1—N4—N3	105.4 (3)	C6—C5—C4	120.0 (3)
C8—N5—C10	107.3 (3)	C6—C5—N5	119.9 (3)
C8—N5—C5	125.3 (3)	C4—C5—N5	120.1 (3)
C10—N5—C5	127.4 (3)	C7—C6—C5	120.0 (3)
C8—N6—C9	108.6 (3)	C7—C6—H6	120.0
H1A—O1—H1C	110.2	C5—C6—H6	120.0
H1A—O1—H1D	110.2	C6—C7—C2	120.9 (4)
H1C—O1—H1D	108.5	C6—C7—H7	119.6
H2A—O2—H2C	142.7	C2—C7—H7	119.6
H2A—O2—H2D	101.7	N6—C8—N5	109.1 (3)
H2C—O2—H2D	108.1	N6—C8—H8	125.5
N4—C1—N1	111.1 (3)	N5—C8—H8	125.5
N4—C1—C2	124.6 (3)	C10—C9—N6	107.5 (4)
N1—C1—C2	124.3 (3)	C10—C9—H9	126.2
C3—C2—C7	118.1 (3)	N6—C9—H9	126.2
C3—C2—C1	122.3 (3)	C9—C10—N5	107.5 (3)
C7—C2—C1	119.6 (3)	C9—C10—H10	126.2
C4—C3—C2	121.0 (3)	N5—C10—H10	126.2

C1—N1—N2—N3	−0.1 (5)	C8—N5—C5—C6	23.6 (6)
N1—N2—N3—N4	0.1 (5)	C10—N5—C5—C6	−155.1 (4)
N2—N3—N4—C1	0.0 (5)	C8—N5—C5—C4	−157.2 (4)
N3—N4—C1—N1	−0.1 (5)	C10—N5—C5—C4	24.1 (6)
N3—N4—C1—C2	179.5 (4)	C4—C5—C6—C7	1.9 (6)
N2—N1—C1—N4	0.1 (4)	N5—C5—C6—C7	−178.9 (3)
N2—N1—C1—C2	−179.5 (3)	C5—C6—C7—C2	−0.4 (6)
N4—C1—C2—C3	163.4 (4)	C3—C2—C7—C6	−1.4 (6)
N1—C1—C2—C3	−17.1 (6)	C1—C2—C7—C6	178.6 (4)
N4—C1—C2—C7	−16.6 (6)	C9—N6—C8—N5	−0.5 (5)
N1—C1—C2—C7	162.9 (4)	C10—N5—C8—N6	0.2 (5)
C7—C2—C3—C4	1.8 (6)	C5—N5—C8—N6	−178.7 (3)
C1—C2—C3—C4	−178.2 (3)	C8—N6—C9—C10	0.7 (5)
C2—C3—C4—C5	−0.4 (6)	N6—C9—C10—N5	−0.6 (5)
C3—C4—C5—C6	−1.5 (6)	C8—N5—C10—C9	0.3 (5)
C3—C4—C5—N5	179.3 (3)	C5—N5—C10—C9	179.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2D···N2ⁱ	0.85	2.50	3.235 (7)	146
O2—H2D···N3ⁱ	0.85	1.98	2.823 (7)	172
O2—H2C···O1ⁱⁱ	0.85	2.15	2.994 (9)	170
O2—H2A···O1	0.85	1.92	2.629 (9)	141
O1—H1D···O2ⁱⁱ	0.85	2.55	2.994 (9)	114
O1—H1D···O2	0.85	1.78	2.629 (9)	175
O1—H1C···O1ⁱⁱⁱ	0.85	1.96	2.806 (11)	175
O1—H1A···N1	0.85	1.99	2.790 (5)	157
N2—H2···N6^iv	0.86	1.90	2.758 (5)	174

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z; (iv) x, y−1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₆·2H₂O
M_r	248.26
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.4300 (7), 8.2285 (9), 10.2047 (11)
α, β, γ (°)	97.011 (1), 90.813 (1), 113.449 (2)
V (Å³)	566.74 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.38 × 0.17 × 0.16

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.960, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	2913, 1953, 1199
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.243, 1.05
No. of reflections	1953
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.51

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2D···N2ⁱ	0.85	2.50	3.235 (7)	146
O2—H2D···N3ⁱ	0.85	1.98	2.823 (7)	172
O2—H2C···O1ⁱⁱ	0.85	2.15	2.994 (9)	170
O2—H2A···O1	0.85	1.92	2.629 (9)	141
O1—H1D···O2ⁱⁱ	0.85	2.55	2.994 (9)	114
O1—H1D···O2	0.85	1.78	2.629 (9)	175
O1—H1C···O1ⁱⁱⁱ	0.85	1.96	2.806 (11)	175
O1—H1A···N1	0.85	1.99	2.790 (5)	157
N2—H2···N6^iv	0.86	1.90	2.758 (5)	174

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z; (iv) x, y−1, z−1.

Acknowledgements

The authors acknowledge Henan University of Urban Construction for supporting this work.

References

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