4-(1H-Tetra-zol-5-yl)-1H-indole.

There are two mol-ecules with similar configurations in the asymmetric unit of the title compound, C(9)H(7)N(5), which are linked by inter-molecular N-H⋯N hydrogen bonds into chains with graph-set motif C(2) (2)(8) along the b axis. The indole core has the expected planar geometry in the two mol-ecules, with a maximum deviation of 0.008 (8) Å from the least-squares plane defined by the nine constituent atoms, and the dihedral angles between the indole and tetra-zole rings are similar [42.4 (2) and 42.7 (2)°].

Related literature

For the biological properties of indole and its derivatives, see: Takatoshi & Makoto (1994 ▶). For physical properties of tetra­zole, see: Itoh et al., (1995 ▶). For pharmacological properties of compounds with tetra­zole and indole rings, see: Semenov (2002 ▶). For the synthesis of 5-cyano­indole, see: Frederick (1949 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H7N5

M = 185.20

Triclinic,

a = 9.6535 (7) Å

b = 9.8444 (4) Å

c = 9.9672 (7) Å

α = 83.204 (3)°

β = 65.712 (6)°

γ = 87.627 (3)°

V = 857.28 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.30 × 0.15 × 0.15 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

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

6939 measured reflections

2990 independent reflections

2403 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.240

S = 1.02

2990 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.30 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033271/bx2301sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033271/bx2301Isup2.hkl

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

C9H7N5	Z = 4
Mr = 185.20	F(000) = 384
Triclinic, P1	Dx = 1.435 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6535 (7) Å	Cell parameters from 2795 reflections
b = 9.8444 (4) Å	θ = 3.1–27.5°
c = 9.9672 (7) Å	µ = 0.10 mm−1
α = 83.204 (3)°	T = 293 K
β = 65.712 (6)°	Prism, yellow
γ = 87.627 (3)°	0.30 × 0.15 × 0.15 mm
V = 857.28 (9) Å3

Bruker SMART 1K CCD area-detector diffractometer	2990 independent reflections
Radiation source: fine-focus sealed tube	2403 reflections with I > 2σ(I)
graphite	Rint = 0.037
Detector resolution: 13.6612 pixels mm-1	θmax = 25.0°, θmin = 3.1°
CCD_Profile_fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.737, Tmax = 1.000	l = −11→11
6939 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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.240	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.1252P)2 + 1.2926P] where P = (Fo2 + 2Fc2)/3
2990 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.1822 (4)	0.5189 (4)	0.2581 (4)	0.0371 (8)
C2	0.1565 (4)	0.5725 (4)	0.1253 (4)	0.0397 (9)
C3	0.2419 (4)	0.5213 (4)	−0.0106 (4)	0.0411 (9)
C4	0.3642 (5)	0.4250 (4)	−0.0615 (5)	0.0527 (11)
H4B	0.4128	0.3779	−0.0068	0.063*
C5	0.3934 (5)	0.4173 (5)	−0.2057 (5)	0.0574 (11)
H5B	0.4667	0.3614	−0.2667	0.069*
C6	0.2055 (5)	0.5708 (4)	−0.1327 (4)	0.0435 (9)
C7	0.0930 (5)	0.6655 (4)	−0.1257 (5)	0.0479 (10)
H7B	0.0734	0.6951	−0.2083	0.057*
C8	0.0109 (5)	0.7143 (4)	0.0100 (5)	0.0489 (10)
H8B	−0.0661	0.7774	0.0196	0.059*
C9	0.0433 (4)	0.6690 (4)	0.1319 (4)	0.0405 (9)
H9B	−0.0124	0.7042	0.2212	0.049*
C10	0.2369 (4)	0.9946 (3)	0.2932 (4)	0.0361 (8)
C11	0.3995 (4)	0.9972 (4)	0.2597 (4)	0.0369 (8)
C12	0.4597 (4)	0.9141 (4)	0.3474 (4)	0.0364 (8)
C13	0.3959 (5)	0.8222 (4)	0.4804 (4)	0.0427 (9)
H13A	0.2940	0.7979	0.5327	0.051*
C14	0.5141 (5)	0.7769 (4)	0.5158 (5)	0.0484 (10)
H14A	0.5046	0.7167	0.5984	0.058*
C15	0.6195 (4)	0.9196 (4)	0.3068 (4)	0.0400 (9)
C16	0.7170 (5)	1.0037 (4)	0.1850 (5)	0.0506 (10)
H16A	0.8210	1.0050	0.1601	0.061*
C17	0.6541 (5)	1.0853 (5)	0.1024 (5)	0.0531 (11)
H17A	0.7168	1.1432	0.0209	0.064*
C18	0.4975 (5)	1.0825 (4)	0.1391 (5)	0.0466 (10)
H18A	0.4583	1.1389	0.0816	0.056*
N1	0.1790 (4)	0.5964 (3)	0.3603 (3)	0.0386 (7)
H1A	0.1685	0.6838	0.3552	0.046*
N2	0.1950 (4)	0.5168 (3)	0.4730 (4)	0.0446 (8)
N3	0.2064 (4)	0.3928 (3)	0.4385 (4)	0.0467 (8)
N4	0.2006 (4)	0.3901 (3)	0.3040 (4)	0.0435 (8)
N5	0.3005 (4)	0.5030 (4)	−0.2493 (4)	0.0547 (9)
H5A	0.3015	0.5130	−0.3365	0.066*
N9	0.1456 (3)	0.8869 (3)	0.3328 (4)	0.0400 (8)
N8	0.0065 (4)	0.9348 (3)	0.3460 (4)	0.0469 (8)
N7	0.0106 (4)	1.0667 (3)	0.3174 (4)	0.0467 (8)
N6	0.1544 (4)	1.1054 (3)	0.2838 (4)	0.0412 (8)
H6A	0.1880	1.1883	0.2601	0.049*
N10	0.6481 (4)	0.8330 (3)	0.4119 (4)	0.0470 (8)
H10A	0.7363	0.8168	0.4121	0.056*

	U11	U22	U33	U12	U13	U23
C1	0.040 (2)	0.0331 (18)	0.039 (2)	−0.0061 (15)	−0.0166 (16)	−0.0030 (15)
C2	0.044 (2)	0.0339 (18)	0.045 (2)	−0.0051 (16)	−0.0215 (18)	−0.0025 (15)
C3	0.041 (2)	0.040 (2)	0.043 (2)	−0.0047 (16)	−0.0178 (17)	−0.0036 (16)
C4	0.049 (2)	0.042 (2)	0.069 (3)	0.0052 (18)	−0.025 (2)	−0.011 (2)
C5	0.056 (3)	0.057 (3)	0.052 (3)	0.000 (2)	−0.013 (2)	−0.014 (2)
C6	0.051 (2)	0.048 (2)	0.034 (2)	−0.0138 (18)	−0.0212 (17)	0.0030 (16)
C7	0.054 (2)	0.049 (2)	0.050 (2)	−0.0084 (19)	−0.032 (2)	0.0047 (18)
C8	0.043 (2)	0.042 (2)	0.065 (3)	−0.0011 (17)	−0.027 (2)	−0.0027 (19)
C9	0.038 (2)	0.0358 (19)	0.048 (2)	0.0008 (15)	−0.0181 (17)	−0.0065 (16)
C10	0.043 (2)	0.0288 (17)	0.044 (2)	0.0036 (15)	−0.0243 (17)	−0.0075 (15)
C11	0.0369 (19)	0.0323 (18)	0.044 (2)	0.0016 (15)	−0.0188 (16)	−0.0067 (15)
C12	0.0382 (19)	0.0326 (18)	0.043 (2)	0.0034 (15)	−0.0198 (16)	−0.0081 (15)
C13	0.046 (2)	0.040 (2)	0.043 (2)	0.0027 (16)	−0.0186 (18)	−0.0048 (16)
C14	0.053 (2)	0.050 (2)	0.047 (2)	0.0083 (19)	−0.027 (2)	−0.0031 (18)
C15	0.0348 (19)	0.040 (2)	0.050 (2)	0.0055 (15)	−0.0217 (17)	−0.0128 (17)
C16	0.041 (2)	0.052 (2)	0.058 (3)	−0.0035 (18)	−0.019 (2)	−0.011 (2)
C17	0.050 (2)	0.055 (2)	0.052 (2)	−0.010 (2)	−0.019 (2)	0.0002 (19)
C18	0.051 (2)	0.040 (2)	0.051 (2)	−0.0028 (17)	−0.026 (2)	0.0036 (17)
N1	0.0492 (18)	0.0278 (15)	0.0448 (18)	0.0002 (13)	−0.0255 (15)	−0.0034 (12)
N2	0.059 (2)	0.0448 (19)	0.0367 (17)	−0.0017 (15)	−0.0272 (16)	0.0015 (14)
N3	0.058 (2)	0.0412 (18)	0.049 (2)	0.0004 (15)	−0.0331 (17)	0.0069 (14)
N4	0.051 (2)	0.0360 (17)	0.0468 (19)	0.0025 (14)	−0.0231 (16)	−0.0047 (14)
N5	0.061 (2)	0.063 (2)	0.0390 (19)	−0.0047 (18)	−0.0200 (17)	−0.0027 (16)
N9	0.0388 (17)	0.0334 (16)	0.055 (2)	0.0025 (13)	−0.0259 (15)	−0.0060 (14)
N8	0.0436 (19)	0.0404 (18)	0.065 (2)	0.0011 (14)	−0.0299 (17)	−0.0063 (16)
N7	0.0447 (19)	0.0421 (18)	0.059 (2)	0.0022 (14)	−0.0278 (17)	−0.0018 (15)
N6	0.0442 (18)	0.0301 (15)	0.056 (2)	0.0027 (13)	−0.0278 (16)	−0.0020 (13)
N10	0.0412 (18)	0.053 (2)	0.057 (2)	0.0129 (15)	−0.0305 (17)	−0.0113 (16)

C1—N4	1.326 (5)	C12—C15	1.427 (5)
C1—N1	1.333 (5)	C12—C13	1.430 (5)
C1—C2	1.479 (5)	C13—C14	1.370 (6)
C2—C9	1.404 (5)	C13—H13A	0.9300
C2—C3	1.407 (5)	C14—N10	1.368 (6)
C3—C6	1.428 (5)	C14—H14A	0.9300
C3—C4	1.441 (6)	C15—N10	1.382 (5)
C4—C5	1.357 (6)	C15—C16	1.390 (6)
C4—H4B	0.9300	C16—C17	1.381 (6)
C5—N5	1.369 (6)	C16—H16A	0.9300
C5—H5B	0.9300	C17—C18	1.402 (6)
C6—N5	1.376 (5)	C17—H17A	0.9300
C6—C7	1.386 (6)	C18—H18A	0.9300
C7—C8	1.388 (6)	N1—N2	1.350 (4)
C7—H7B	0.9300	N1—H1A	0.8600
C8—C9	1.396 (6)	N2—N3	1.295 (5)
C8—H8B	0.9300	N3—N4	1.369 (4)
C9—H9B	0.9300	N5—H5A	0.8600
C10—N9	1.323 (5)	N9—N8	1.364 (4)
C10—N6	1.341 (4)	N8—N7	1.295 (4)
C10—C11	1.465 (5)	N7—N6	1.347 (4)
C11—C18	1.392 (5)	N6—H6A	0.8600
C11—C12	1.406 (5)	N10—H10A	0.8600
N4—C1—N1	107.9 (3)	C14—C13—C12	106.7 (4)
N4—C1—C2	128.4 (3)	C14—C13—H13A	126.7
N1—C1—C2	123.5 (3)	C12—C13—H13A	126.7
C9—C2—C3	118.4 (4)	N10—C14—C13	110.2 (4)
C9—C2—C1	121.9 (3)	N10—C14—H14A	124.9
C3—C2—C1	119.7 (3)	C13—C14—H14A	124.9
C2—C3—C6	117.1 (4)	N10—C15—C16	130.6 (4)
C2—C3—C4	135.0 (4)	N10—C15—C12	106.8 (3)
C6—C3—C4	107.9 (4)	C16—C15—C12	122.6 (4)
C5—C4—C3	105.7 (4)	C17—C16—C15	117.7 (4)
C5—C4—H4B	127.2	C17—C16—H16A	121.2
C3—C4—H4B	127.2	C15—C16—H16A	121.2
C4—C5—N5	110.8 (4)	C16—C17—C18	121.2 (4)
C4—C5—H5B	124.6	C16—C17—H17A	119.4
N5—C5—H5B	124.6	C18—C17—H17A	119.4
N5—C6—C7	129.9 (4)	C11—C18—C17	121.4 (4)
N5—C6—C3	105.7 (4)	C11—C18—H18A	119.3
C7—C6—C3	124.4 (4)	C17—C18—H18A	119.3
C6—C7—C8	117.1 (4)	C1—N1—N2	109.6 (3)
C6—C7—H7B	121.4	C1—N1—H1A	125.2
C8—C7—H7B	121.4	N2—N1—H1A	125.2
C7—C8—C9	120.3 (4)	N3—N2—N1	105.8 (3)
C7—C8—H8B	119.8	N2—N3—N4	110.8 (3)
C9—C8—H8B	119.8	C1—N4—N3	105.9 (3)
C8—C9—C2	122.7 (4)	C5—N5—C6	109.9 (4)
C8—C9—H9B	118.7	C5—N5—H5A	125.0
C2—C9—H9B	118.7	C6—N5—H5A	125.0
N9—C10—N6	107.4 (3)	C10—N9—N8	106.6 (3)
N9—C10—C11	128.0 (3)	N7—N8—N9	110.3 (3)
N6—C10—C11	124.6 (3)	N8—N7—N6	106.3 (3)
C18—C11—C12	118.8 (3)	C10—N6—N7	109.4 (3)
C18—C11—C10	120.0 (3)	C10—N6—H6A	125.3
C12—C11—C10	121.2 (3)	N7—N6—H6A	125.3
C11—C12—C15	118.3 (3)	C14—N10—C15	109.3 (3)
C11—C12—C13	134.6 (3)	C14—N10—H10A	125.4
C15—C12—C13	107.0 (3)	C15—N10—H10A	125.4
N4—C1—C2—C9	133.5 (4)	C12—C13—C14—N10	−1.0 (5)
N1—C1—C2—C9	−41.2 (5)	C11—C12—C15—N10	178.1 (3)
N4—C1—C2—C3	−43.3 (6)	C13—C12—C15—N10	0.4 (4)
N1—C1—C2—C3	142.1 (4)	C11—C12—C15—C16	0.2 (5)
C9—C2—C3—C6	−0.7 (5)	C13—C12—C15—C16	−177.5 (4)
C1—C2—C3—C6	176.2 (3)	N10—C15—C16—C17	−176.8 (4)
C9—C2—C3—C4	179.7 (4)	C12—C15—C16—C17	0.6 (6)
C1—C2—C3—C4	−3.4 (6)	C15—C16—C17—C18	−0.6 (6)
C2—C3—C4—C5	178.1 (4)	C12—C11—C18—C17	1.1 (6)
C6—C3—C4—C5	−1.5 (4)	C10—C11—C18—C17	−178.7 (4)
C3—C4—C5—N5	0.9 (5)	C16—C17—C18—C11	−0.2 (7)
C2—C3—C6—N5	−178.3 (3)	N4—C1—N1—N2	−0.2 (4)
C4—C3—C6—N5	1.4 (4)	C2—C1—N1—N2	175.4 (3)
C2—C3—C6—C7	0.4 (6)	C1—N1—N2—N3	−0.5 (4)
C4—C3—C6—C7	−180.0 (4)	N1—N2—N3—N4	0.9 (4)
N5—C6—C7—C8	178.0 (4)	N1—C1—N4—N3	0.8 (4)
C3—C6—C7—C8	−0.3 (6)	C2—C1—N4—N3	−174.6 (4)
C6—C7—C8—C9	0.5 (6)	N2—N3—N4—C1	−1.1 (4)
C7—C8—C9—C2	−0.9 (6)	C4—C5—N5—C6	−0.1 (5)
C3—C2—C9—C8	1.0 (5)	C7—C6—N5—C5	−179.4 (4)
C1—C2—C9—C8	−175.8 (3)	C3—C6—N5—C5	−0.8 (4)
N9—C10—C11—C18	137.4 (4)	N6—C10—N9—N8	0.5 (4)
N6—C10—C11—C18	−40.4 (5)	C11—C10—N9—N8	−177.6 (4)
N9—C10—C11—C12	−42.3 (6)	C10—N9—N8—N7	−0.6 (4)
N6—C10—C11—C12	139.8 (4)	N9—N8—N7—N6	0.5 (4)
C18—C11—C12—C15	−1.1 (5)	N9—C10—N6—N7	−0.2 (4)
C10—C11—C12—C15	178.7 (3)	C11—C10—N6—N7	178.0 (3)
C18—C11—C12—C13	175.9 (4)	N8—N7—N6—C10	−0.2 (4)
C10—C11—C12—C13	−4.3 (6)	C13—C14—N10—C15	1.3 (5)
C11—C12—C13—C14	−176.9 (4)	C16—C15—N10—C14	176.6 (4)
C15—C12—C13—C14	0.3 (4)	C12—C15—N10—C14	−1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N9	0.86	2.00	2.858 (4)	177.
N6—H6A···N4i	0.86	2.10	2.899 (4)	154.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N9	0.86	2.00	2.858 (4)	177
N6—H6A⋯N4i	0.86	2.10	2.899 (4)	154

Symmetry code: (i) .