6-(1H-Tetra-zol-5-yl)-1H-indole monohydrate.

In the title compound, C(9)H(7)N(5)·H(2)O, the tetra-zole ring forms a dihedral angle of 1.82 (1)° with the mean plane of the indole fragment. In the crystal, mol-ecules are linked by inter-molecular O-H⋯N, N-H⋯O and N-H⋯N hydrogen bonds into a two-dimensional network parallel to (100). Addtional stabilization is provide by weak π-π inter-actions with a centroid-centroid distance of 3.698 (2) Å.

Related literature

For the synthesis and pharmacological activity of compounds containing indole and tetra­zole groups, see: Itoh et al. (1995 ▶); Semenov (2002 ▶). For the synthesis of 6-cyano­indole, a starting material for the title compound, see: Frederick (1949 ▶).

Experimental

Crystal data

C9H7N5·H2O

M = 203.21

Monoclinic,

a = 17.175 (3) Å

b = 4.0653 (8) Å

c = 14.421 (3) Å

β = 107.59 (3)°

V = 959.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.05 × 0.05 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.737, T max = 1.000

7430 measured reflections

1683 independent reflections

945 reflections with I > 2σ(I)

R int = 0.120

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.131

S = 1.01

1683 reflections

144 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003990/lh5195sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003990/lh5195Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H7N5·H2O	F(000) = 424
Mr = 203.21	Dx = 1.406 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2795 reflections
a = 17.175 (3) Å	θ = 3.1–27.5°
b = 4.0653 (8) Å	µ = 0.10 mm−1
c = 14.421 (3) Å	T = 293 K
β = 107.59 (3)°	Needle, colorless
V = 959.8 (3) Å3	0.20 × 0.05 × 0.05 mm
Z = 4

Rigaku Mercury2 diffractometer	1683 independent reflections
Radiation source: fine-focus sealed tube	945 reflections with I > 2σ(I)
graphite	Rint = 0.120
Detector resolution: 13.6612 pixels mm-1	θmax = 25.0°, θmin = 3.2°
CCD_Profile_fitting scans	h = −20→20
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −4→4
Tmin = 0.737, Tmax = 1.000	l = −17→17
7430 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0398P)2] where P = (Fo2 + 2Fc2)/3
1683 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
O1	0.0699 (2)	−0.0517 (10)	0.1761 (2)	0.0720 (10)
H1A	0.088 (2)	−0.161 (10)	0.132 (3)	0.095 (17)*
H1B	0.033 (3)	0.048 (11)	0.147 (3)	0.10 (2)*
N1	0.19161 (16)	−0.0016 (7)	0.5257 (2)	0.0453 (8)
N2	0.12138 (17)	−0.1708 (7)	0.5143 (2)	0.0518 (9)
N3	0.08061 (16)	−0.1971 (7)	0.4227 (2)	0.0509 (9)
N4	0.12440 (15)	−0.0389 (7)	0.37351 (19)	0.0415 (8)
H4N	0.1108	−0.0189	0.3113	0.062*
N5	0.32387 (16)	0.6304 (7)	0.21458 (19)	0.0442 (8)
H5N	0.2898	0.6026	0.1576	0.066*
C1	0.19266 (19)	0.0829 (8)	0.4367 (2)	0.0349 (8)
C2	0.25600 (18)	0.2697 (8)	0.4122 (2)	0.0325 (8)
C3	0.25007 (18)	0.3476 (8)	0.3176 (2)	0.0349 (8)
H3	0.2048	0.2852	0.2666	0.042*
C4	0.31364 (19)	0.5219 (8)	0.3008 (2)	0.0346 (8)
C5	0.3976 (2)	0.7902 (8)	0.2348 (2)	0.0436 (9)
H5	0.4185	0.8834	0.1884	0.052*
C6	0.4357 (2)	0.7929 (8)	0.3320 (2)	0.0394 (9)
H6	0.4862	0.8864	0.3636	0.047*
C7	0.38315 (18)	0.6239 (8)	0.3762 (2)	0.0339 (8)
C8	0.38770 (19)	0.5422 (8)	0.4718 (2)	0.0403 (9)
H8	0.4327	0.6052	0.5231	0.048*
C9	0.32503 (18)	0.3679 (8)	0.4894 (2)	0.0382 (9)
H9	0.3280	0.3136	0.5530	0.046*

	U11	U22	U33	U12	U13	U23
O1	0.057 (2)	0.112 (3)	0.0391 (17)	0.0266 (19)	0.0019 (15)	−0.0135 (18)
N1	0.0348 (18)	0.058 (2)	0.0385 (18)	−0.0073 (16)	0.0049 (14)	0.0043 (16)
N2	0.0431 (19)	0.069 (2)	0.040 (2)	−0.0068 (17)	0.0080 (16)	0.0037 (17)
N3	0.0424 (19)	0.064 (2)	0.045 (2)	−0.0102 (16)	0.0113 (16)	0.0047 (17)
N4	0.0327 (16)	0.056 (2)	0.0329 (16)	−0.0036 (15)	0.0047 (14)	0.0050 (15)
N5	0.0454 (18)	0.057 (2)	0.0279 (16)	0.0038 (16)	0.0071 (13)	0.0024 (14)
C1	0.032 (2)	0.037 (2)	0.032 (2)	0.0057 (16)	0.0037 (16)	−0.0009 (16)
C2	0.0322 (19)	0.034 (2)	0.0292 (19)	0.0031 (16)	0.0062 (15)	−0.0008 (15)
C3	0.0297 (18)	0.043 (2)	0.030 (2)	0.0060 (17)	0.0047 (15)	−0.0045 (16)
C4	0.038 (2)	0.040 (2)	0.0256 (19)	0.0101 (18)	0.0093 (16)	0.0014 (16)
C5	0.038 (2)	0.046 (2)	0.048 (2)	0.0017 (19)	0.0154 (18)	0.0049 (19)
C6	0.0371 (19)	0.045 (2)	0.034 (2)	−0.0005 (18)	0.0075 (17)	0.0021 (17)
C7	0.034 (2)	0.037 (2)	0.0288 (19)	0.0045 (16)	0.0072 (16)	−0.0011 (16)
C8	0.035 (2)	0.051 (2)	0.029 (2)	−0.0065 (17)	0.0010 (16)	−0.0045 (17)
C9	0.041 (2)	0.047 (2)	0.0240 (19)	−0.0011 (18)	0.0052 (16)	−0.0010 (16)

O1—H1A	0.90 (4)	C2—C9	1.417 (4)
O1—H1B	0.77 (4)	C3—C4	1.383 (4)
N1—C1	1.333 (4)	C3—H3	0.9300
N1—N2	1.355 (3)	C4—C7	1.413 (4)
N2—N3	1.298 (3)	C5—C6	1.355 (4)
N3—N4	1.344 (3)	C5—H5	0.9300
N4—C1	1.344 (4)	C6—C7	1.429 (4)
N4—H4N	0.8600	C6—H6	0.9300
N5—C5	1.374 (4)	C7—C8	1.397 (4)
N5—C4	1.380 (4)	C8—C9	1.375 (4)
N5—H5N	0.8600	C8—H8	0.9300
C1—C2	1.456 (4)	C9—H9	0.9300
C2—C3	1.373 (4)
H1A—O1—H1B	106 (4)	N5—C4—C3	130.1 (3)
C1—N1—N2	106.5 (3)	N5—C4—C7	107.0 (3)
N3—N2—N1	110.6 (3)	C3—C4—C7	122.9 (3)
N2—N3—N4	106.4 (2)	C6—C5—N5	110.5 (3)
C1—N4—N3	109.3 (3)	C6—C5—H5	124.8
C1—N4—H4N	125.3	N5—C5—H5	124.8
N3—N4—H4N	125.3	C5—C6—C7	106.6 (3)
C5—N5—C4	108.7 (3)	C5—C6—H6	126.7
C5—N5—H5N	125.7	C7—C6—H6	126.7
C4—N5—H5N	125.7	C8—C7—C4	118.2 (3)
N1—C1—N4	107.2 (3)	C8—C7—C6	134.5 (3)
N1—C1—C2	126.7 (3)	C4—C7—C6	107.3 (3)
N4—C1—C2	126.2 (3)	C9—C8—C7	119.4 (3)
C3—C2—C9	120.6 (3)	C9—C8—H8	120.3
C3—C2—C1	121.7 (3)	C7—C8—H8	120.3
C9—C2—C1	117.7 (3)	C8—C9—C2	121.0 (3)
C2—C3—C4	117.8 (3)	C8—C9—H9	119.5
C2—C3—H3	121.1	C2—C9—H9	119.5
C4—C3—H3	121.1
C1—N1—N2—N3	1.0 (4)	C2—C3—C4—N5	179.7 (3)
N1—N2—N3—N4	−0.8 (4)	C2—C3—C4—C7	−0.6 (4)
N2—N3—N4—C1	0.2 (4)	C4—N5—C5—C6	−0.7 (4)
N2—N1—C1—N4	−0.9 (4)	N5—C5—C6—C7	0.1 (4)
N2—N1—C1—C2	179.6 (3)	N5—C4—C7—C8	−179.8 (3)
N3—N4—C1—N1	0.4 (4)	C3—C4—C7—C8	0.5 (5)
N3—N4—C1—C2	179.9 (3)	N5—C4—C7—C6	−0.8 (3)
N1—C1—C2—C3	−178.9 (3)	C3—C4—C7—C6	179.4 (3)
N4—C1—C2—C3	1.6 (5)	C5—C6—C7—C8	179.2 (3)
N1—C1—C2—C9	1.5 (5)	C5—C6—C7—C4	0.4 (3)
N4—C1—C2—C9	−177.9 (3)	C4—C7—C8—C9	−0.2 (5)
C9—C2—C3—C4	0.4 (5)	C6—C7—C8—C9	−178.8 (3)
C1—C2—C3—C4	−179.1 (3)	C7—C8—C9—C2	0.1 (5)
C5—N5—C4—C3	−179.4 (3)	C3—C2—C9—C8	−0.2 (5)
C5—N5—C4—C7	0.9 (3)	C1—C2—C9—C8	179.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N2i	0.90 (4)	2.07 (4)	2.957 (4)	169 (4)
O1—H1B···N3ii	0.76 (5)	2.17 (5)	2.927 (5)	172 (5)
N4—H4N···O1	0.86	1.87	2.715 (4)	169
N5—H5N···N1iii	0.86	2.17	3.019 (4)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N2i	0.90 (4)	2.07 (4)	2.957 (4)	169 (4)
O1—H1B⋯N3ii	0.76 (5)	2.17 (5)	2.927 (5)	172 (5)
N4—H4N⋯O1	0.86	1.87	2.715 (4)	169
N5—H5N⋯N1iii	0.86	2.17	3.019 (4)	171

Symmetry codes: (i) ; (ii) ; (iii) .