4-(1H-Tetra­zol-5-yl)-1H-indole

Ge, Y.-H.; Han, P.; Wei, P.; Ou-yang, P.-K.

doi:10.1107/S1600536810033271

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2390

https://doi.org/10.1107/S1600536810033271

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4-(1H-Tetrazol-5-yl)-1H-indole

Yu-Hua Ge,^a,^b ^* Pei Han,^b Ping Wei ^a and Ping-Kai Ou-yang ^a

^aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing, People's Republic of China, and ^bDepartment of Chemistry and Chemical Engineering, Southeast Universiy, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: geyuhua@seu.edu.cn

(Received 6 August 2010; accepted 18 August 2010; online 25 August 2010)

There are two molecules with similar configurations in the asymmetric unit of the title compound, C₉H₇N₅, which are linked by intermolecular N—H⋯N hydrogen bonds into chains with graph-set motif C₂²(8) along the b axis. The indole core has the expected planar geometry in the two molecules, 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 tetrazole 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_r = 185.20
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.076
wR(F²) = 0.240
S = 1.02
2990 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) x, y+1, z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033271/bx2301Isup2.hkl

checkCIF report

Comment top

Indole and its derivatives always possess good physiological activity, which are widely used as medicine, pesticide and organic chemical intermediates (Takatoshi & Makoto, 1994). Meanwhile, tetrazole is not only of good anticancer activities but also a kind of excellent ligands, it can coordinate all kinds of metal ions to form the complexes with significant optical activity (Itoh et al., 1995). In recent decades, there are some reports on the compounds which are synthesized by the combination of the tetrazole and indole rings, and the property study reveals that these compounds always perform unique pharmacological activities (Semenov, 2002).We report here the compound structure of 4- (1-H-tetrazol-5-yl)-1H-indole, (I). As far as we know, there are no reports on the indole connecting the tetrazole on the C atom. In the title compound C₉H₇N₅, (I) there two molecules in the asymmetric unit which are linked by one intra and intermolecular N—H···N hydrogen bond with set graph-motif C²₂(8) along b axis (Bernstein et al., 1995), Fig. 2. The indole core has the expected planar geometry. In both molecules of the symmetric unit the dihedral angles between the indole and tetrazole rings are very close similar 42.4 (2) and 42.7 (2)° so, the two crystallographically independent molecules have almost the same extended conformations and similar bond lengths and angles.

Related literature top

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 top

All chemicals used (reagent grade) were commercially available. 5-Cyanoindole is synthesized following the methods described by Frederick (Frederick, 1949). To the stirring DMF solution of NaN₃ and Triethylamine, 5-Cyanoindole was added. Then the whole mixture was heated to 120°C, 1 h later, the solution was cooled to room temperature, and DMF was distilled in vacuum. With some follow-up treatment, the crude product was recrystallized in methanol and seven days later, yellow prism crystal was obtained.

Structure description top

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).

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

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the the atom-numbering scheme.
	Fig. 2. The molecular packing of the title compound (I). Hydrogen bonds are shown as dashed lines.

4-(1H-tetrazol-5-yl)-1H-indole top

Crystal data top

C₉H₇N₅	Z = 4
M_r = 185.20	F(000) = 384
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	2990 independent reflections
Radiation source: fine-focus sealed tube	2403 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 13.6612 pixels mm^-1	θ_max = 25.0°, θ_min = 3.1°
CCD_Profile_fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
T_min = 0.737, T_max = 1.000	l = −11→11
6939 measured reflections

Refinement top

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(F_o²) + (0.1252P)² + 1.2926P] where P = (F_o² + 2F_c²)/3
2990 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₉H₇N₅	γ = 87.627 (3)°
M_r = 185.20	V = 857.28 (9) Å³
Triclinic, P1	Z = 4
a = 9.6535 (7) Å	Mo Kα radiation
b = 9.8444 (4) Å	µ = 0.10 mm⁻¹
c = 9.9672 (7) Å	T = 293 K
α = 83.204 (3)°	0.30 × 0.15 × 0.15 mm
β = 65.712 (6)°

Data collection top

Bruker SMART 1K CCD area-detector diffractometer	2990 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2403 reflections with I > 2σ(I)
T_min = 0.737, T_max = 1.000	R_int = 0.037
6939 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	0 restraints
wR(F²) = 0.240	H-atom parameters constrained
S = 1.02	Δρ_max = 0.39 e Å⁻³
2990 reflections	Δρ_min = −0.30 e Å⁻³
253 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₉H₇N₅
M_r	185.20
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.6535 (7), 9.8444 (4), 9.9672 (7)
α, β, γ (°)	83.204 (3), 65.712 (6), 87.627 (3)
V (Å³)	857.28 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART 1K CCD area-detector
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.737, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6939, 2990, 2403
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.240, 1.02
No. of reflections	2990
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.30

Computer programs: CrystalClear (Rigaku, 2005), 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
N1—H1A···N9	0.86	2.00	2.858 (4)	177.2
N6—H6A···N4ⁱ	0.86	2.10	2.899 (4)	153.6

Symmetry code: (i) x, y+1, z.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Frederick, C. U. (1949). J. Am. Chem. Soc. 71, 761–766. PubMed Web of Science Google Scholar
Itoh, F., Yukishige, K. & Wajima, M. (1995). Chem. Pharm. Bull. 43, 230–235. CrossRef CAS PubMed Web of Science Google Scholar
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Semenov, B. B. (2002). Russ. Chem. Bull. 51, 357–358. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Takatoshi, S. & Makoto, I. (1994). Bull. Chem. Soc. Jpn, 67, 3139–3141. Google Scholar

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